Chemical Engineering - Industrial Organic Chemistry

The Beginning of the end

Complete course

The Beginning of the END – Industrial Organic Chemistry Andrea Locaspi – The Beginning of the End: Industrial Organic Chemistry ii FOR AN ELECTRONIC FI LE ON WORD: FOR -E-WO RD ................................ ................................ ................................ ... 1 L1 – PRODUCING THE P RODUCTS: PRODUCTION LINES ................................ ................................ .............................. 2 L2 – RAW MATERIALS ................................ ................................ ................................ ................................ ................. 4 Chemical vs energy sector: Shaolin showdown ................................ ................................ ................................ .......... 4 Where are the raws? ................................ ................................ ................................ ................................ .................. 4 A bit of history ................................ ................................ ................................ ................................ ............................ 4 OIL ................................ ................................ ................................ ................................ ................................ ................... 4 Composition ................................ ................................ ................................ ................................ ............................... 4 Classification ................................ ................................ ................................ ................................ .............................. 5 Advantages ................................ ................................ ................................ ................................ ................................ 5 Applications and uses ................................ ................................ ................................ ................................ ................. 6 NATURAL GAS ................................ ................................ ................................ ................................ ................................ .... 6 Composition ................................ ................................ ................................ ................................ ............................... 6 Sources ................................ ................................ ................................ ................................ ................................ ....... 7 Treatment and purification ................................ ................................ ................................ ................................ ........ 7 Transport and Storage ................................ ................................ ................................ ................................ ............... 8 Usage ................................ ................................ ................................ ................................ ................................ ......... 8 COAL ................................ ................................ ................................ ................................ ................................ ................ 8 Composition ................................ ................................ ................................ ................................ ............................... 9 Pre -treatment, transportation and storage ................................ ................................ ................................ ............... 9 Uses ................................ ................................ ................................ ................................ ................................ ............ 9 Carbonization/coking ................................ ................................ ................................ ................................ ................................ 9 Direct Liquefaction ................................ ................................ ................................ ................................ ................................ ..10 Gasification ................................ ................................ ................................ ................................ ................................ ............. 10 Indirect liquefaction ................................ ................................ ................................ ................................ ................................ 10 BIOMASS ................................ ................................ ................................ ................................ ................................ ......... 11 L3 – CH 3OH: METHANOL PRODUCT ION ................................ ................................ ................................ ...................... 12 GENERAL INFORMATION (11713) ................................ ................................ ................................ ................................ ........ 12 Properties ................................ ................................ ................................ ................................ ................................ . 12 History, uses and future ................................ ................................ ................................ ................................ ........... 12 METHANOL SYNTHESIS ................................ ................................ ................................ ................................ ....................... 13 Reaction pathways ................................ ................................ ................................ ................................ ................... 13 Thermodynamics ................................ ................................ ................................ ................................ ...................... 14 Catalysts ................................ ................................ ................................ ................................ ................................ ... 14 BASF catalyst ................................ ................................ ................................ ................................ ................................ ........... 14 ICI catalyst ................................ ................................ ................................ ................................ ................................ ............... 14 Kinetics ................................ ................................ ................................ ................................ ................................ ..... 15 BASF catalyst ................................ ................................ ................................ ................................ ................................ ........... 15 Copper catalyst ................................ ................................ ................................ ................................ ................................ ....... 15 Reactor Design and Development ................................ ................................ ................................ ............................ 15 1. Multiple adiabatic reactors ................................ ................................ ................................ ................................ ....... 15 2. Quench reactors ................................ ................................ ................................ ................................ ....................... 16 3. Tube -cooled react ors ................................ ................................ ................................ ................................ ................ 16 4. Multitubular reactors ................................ ................................ ................................ ................................ ............... 16 5. Steam -raising reactor ................................ ................................ ................................ ................................ ............... 16 Process Technology ................................ ................................ ................................ ................................ .................. 17 Syngas production ................................ ................................ ................................ ................................ ................................ ...17 MeOH from natural ga s (PFD) ................................ ................................ ................................ ................................ ................. 18 ICI process ................................ ................................ ................................ ................................ ................................ ............... 18 Lurgi Megamethanol technology ................................ ................................ ................................ ................................ ............ 18 Slurry -phase process. ................................ ................................ ................................ ................................ .............................. 19 Other technologies ................................ ................................ ................................ ................................ ................................ ..19 TOPSOE ................................ ................................ ................................ ................................ ................................ .............. 19 LINDE ................................ ................................ ................................ ................................ ................................ .................. 19 Andrea Locaspi – The Beginning of the End: Industrial Organic Chemistry iii This is the future: power, precision, prestige (https://www.youtube.com/watch?v=dZq48HsjXi4) ................................ ...... 19 L4 – CH 2O: FORMALDEHYDE FABR ICATION ................................ ................................ ................................ ................ 20 GENERAL INFORMATION (8152) ................................ ................................ ................................ ................................ .......... 20 Properties ................................ ................................ ................................ ................................ ................................ . 20 Production and usage ................................ ................................ ................................ ................................ .............. 20 RAW MATERIALS ................................ ................................ ................................ ................................ ............................... 20 SILVER CATALYST PROCESS ................................ ................................ ................................ ................................ .................. 21 Thermodynamics ................................ ................................ ................................ ................................ ...................... 21 Better safe than sorry ................................ ................................ ................................ ................................ .............. 21 Catalyst ................................ ................................ ................................ ................................ ................................ .... 22 Process technology ................................ ................................ ................................ ................................ ................... 22 BASF process, complete conversion of methanol ................................ ................................ ................................ ................... 22 Incomplete methanol conversion process ................................ ................................ ................................ .............................. 23 FORMOX PROCESS ................................ ................................ ................................ ................................ ............................. 23 The catalyst ................................ ................................ ................................ ................................ .............................. 23 Redox Kinetics ................................ ................................ ................................ ................................ .......................... 24 Reactor and process ................................ ................................ ................................ ................................ ................. 24 The reactor. ................................ ................................ ................................ ................................ ................................ ............. 25 COMPARISON ................................ ................................ ................................ ................................ ................................ ... 25 L5 – CH 3COOH: ACETIC ACID PR OCESS ................................ ................................ ................................ ....................... 26 GENE RAL INFORMATION (77) ................................ ................................ ................................ ................................ .............. 26 Properties ................................ ................................ ................................ ................................ ................................ . 26 Main uses ................................ ................................ ................................ ................................ ................................ . 26 History channel and the production ................................ ................................ ................................ ......................... 26 Breakfast (a short break or breaking the fastening?) - Homogeneous Catalytic Process ................................ ......... 27 ACETALDEHYDE OXIDATIO N ................................ ................................ ................................ ................................ ................. 27 The reactions ................................ ................................ ................................ ................................ ............................ 27 Process scheme ................................ ................................ ................................ ................................ ........................ 28 CARBONYLATION OF METH ANO L ................................ ................................ ................................ ................................ ........... 29 Cobalt – the BASF process ................................ ................................ ................................ ................................ ........ 29 Catalyst activation ................................ ................................ ................................ ................................ ................................ ...29 The catalytic cycle ................................ ................................ ................................ ................................ ................................ ...29 The process ................................ ................................ ................................ ................................ ................................ ............. 29 Rhodium – The Monsanto Process ................................ ................................ ................................ ........................... 30 The catalytic cycle ................................ ................................ ................................ ................................ ................................ ...30 The process ................................ ................................ ................................ ................................ ................................ ............. 31 Rhodium again – the CELANE SE process ................................ ................................ ................................ .................. 31 Iridium – the Cativa (BP) process ................................ ................................ ................................ ............................. 31 The catalytic cycle ................................ ................................ ................................ ................................ ................................ ...31 The process ................................ ................................ ................................ ................................ ................................ ............. 31 Sum up ................................ ................................ ................................ ................................ ................................ ..... 31 L9 – FISCHER -TROPSCH SYNTHESIS ................................ ................................ ................................ ............................ 33 GENERAL INFORMATION ................................ ................................ ................................ ................................ ..................... 33 A bit of hysteria history ................................ ................................ ................................ ................................ ............ 33 XtL processes ................................ ................................ ................................ ................................ ............................ 33 THE CHEMICAL SIDE OF THE MOON ................................ ................................ ................................ ................................ ........ 33 The chemistry ................................ ................................ ................................ ................................ ........................... 33 The catalyst ................................ ................................ ................................ ................................ .............................. 34 Iron based catalyst ................................ ................................ ................................ ................................ ................................ ..34 Cobalt based catalysts ................................ ................................ ................................ ................................ ............................. 34 The Mechanism ................................ ................................ ................................ ................................ ........................ 35 Carbide theory ................................ ................................ ................................ ................................ ................................ ........ 35 Oxymethylene theory ................................ ................................ ................................ ................................ ............................. 35 Andrea Locaspi – The Beginning of the End: Industrial Organic Chemistry iv Operating conditions ................................ ................................ ................................ ................................ ................ 35 Under Temperature ................................ ................................ ................................ ................................ ................................ 35 Under Pressure ................................ ................................ ................................ ................................ ................................ ....... 36 Under H 2/CO ratio ................................ ................................ ................................ ................................ ................................ ...36 Under Spatial velocity ................................ ................................ ................................ ................................ ............................. 36 The AS( D)F Anderson -Schulz -Flory Distribution: a quantitative approach ................................ ............................... 36 The Schulz -Flory distribution ................................ ................................ ................................ ................................ ................... 36 Theory vs reality ................................ ................................ ................................ ................................ ................................ ...... 37 Kinetic modelling ................................ ................................ ................................ ................................ ...................... 38 Simplified models ................................ ................................ ................................ ................................ ................................ ....38 An example: Sarup -Wojchiechowski model (SW) ................................ ................................ ................................ .............. 39 Detailed models ................................ ................................ ................................ ................................ ................................ ...... 39 THE ENGINEERING SIDE OF THE MOON ................................ ................................ ................................ ................................ ... 39 Multitubular Fixed -Bed Reactors: MTFBR ................................ ................................ ................................ ................ 41 Shell technology ................................ ................................ ................................ ................................ ................................ ...... 41 Slurry Bubble Column R eactors: SBCR ................................ ................................ ................................ ...................... 42 Circulating fluidized bed ................................ ................................ ................................ ................................ ........... 42 Compact reactors ................................ ................................ ................................ ................................ ..................... 42 L6,L7,L8 - REFINERY PROCESSES ................................ ................................ ................................ ................................ .43 L6 – CRACKING THE CRACKE R (12991) ................................ ................................ ................................ ................................ .. 43 Thermal cracking ................................ ................................ ................................ ................................ ...................... 44 The reaction mechanism ................................ ................................ ................................ ................................ ......................... 44 The processes ................................ ................................ ................................ ................................ ................................ .......... 44 Visbreaking ................................ ................................ ................................ ................................ .............................. 44 Coking ................................ ................................ ................................ ................................ ................................ ...... 45 Delayed coking ................................ ................................ ................................ ................................ ................................ ........ 45 Flexi -coking ................................ ................................ ................................ ................................ ................................ ............. 45 Catalytic Cracking ................................ ................................ ................................ ................................ .................... 46 The good, the catalyst and the mechanism ................................ ................................ ................................ ............................ 46 Deep Web Catalysis – the zeolites ................................ ................................ ................................ ................................ .......... 46 To zeolite or not to zeolite ................................ ................................ ................................ ................................ ................. 47 Zeolites’ beauty: the selectivity ................................ ................................ ................................ ................................ .......... 47 Zeolites product ion ................................ ................................ ................................ ................................ ............................ 47 Back to the catalytic cracking ................................ ................................ ................................ ................................ ............. 47 Operating conditions ................................ ................................ ................................ ................................ ............................... 47 FCC - The Fluidize d Catalytic Cracking ................................ ................................ ................................ ................................ ..... 48 L7 – CATALYTIC REFORMING ................................ ................................ ................................ ................................ ............... 49 Thermodynamics and reaction mechanism ................................ ................................ ................................ ............. 49 The cat has a list - the cat -a-lyst ................................ ................................ ................................ .............................. 50 The trials processes ................................ ................................ ................................ ................................ .................. 51 Semi -regenerative reforming ................................ ................................ ................................ ................................ .................. 51 The reactors ................................ ................................ ................................ ................................ ................................ ....... 51 Continuously -regenerative reforming ................................ ................................ ................................ ................................ ..... 52 Fully-regenerative reforming ................................ ................................ ................................ ................................ .................. 52 L8- HYDROTREATING ................................ ................................ ................................ ................................ .......................... 53 Hydrodesulphurization and HDX ................................ ................................ ................................ .............................. 53 The catalyst, the mechanism and the operative conditions ................................ ................................ ................................ ...53 Plant configuration ................................ ................................ ................................ ................................ ................................ ..54 The reactor ................................ ................................ ................................ ................................ ................................ .............. 54 Trickle bed reactors ................................ ................................ ................................ ................................ ............................ 54 Slurry reactors ................................ ................................ ................................ ................................ ................................ ....55 Ebullating bed reactor ................................ ................................ ................................ ................................ ........................ 55 Hydrocracking ................................ ................................ ................................ ................................ .......................... 55 Standard plant configuration ................................ ................................ ................................ ................................ .................. 56 HYCON process (Shell) ................................ ................................ ................................ ................................ ............................ 56 EST -ENI slurry technology ................................ ................................ ................................ ................................ ....................... 56 Andrea Locaspi – The Beginning of the End: Industrial Organic Chemistry v L10 - STEAM CRACKING ................................ ................................ ................................ ................................ ............. 57 LET’S STUDY THE REACTION ................................ ................................ ................................ ................................ ................. 57 Thermodynamics ................................ ................................ ................................ ................................ ...................... 57 Operating conditions ................................ ................................ ................................ ................................ ................ 57 Cracking severity and Feedstock ................................ ................................ ................................ .............................. 58 Reaction mechanism ................................ ................................ ................................ ................................ ................ 58 Kinetics ................................ ................................ ................................ ................................ ................................ ..... 59 LET’S STUDY THE PROCESS ................................ ................................ ................................ ................................ ................... 59 The Reactor ................................ ................................ ................................ ................................ .............................. 59 The quench ................................ ................................ ................................ ................................ ............................... 60 Coking – a big problem ................................ ................................ ................................ ................................ ............ 60 Process configur ations ................................ ................................ ................................ ................................ ............. 61 LET’S STUDY THE ALTERNATIVE PATHS TO OBTAIN LOWER ALKANES ................................ ................................ ............................. 61 Selective dehydrogenation of light alkenes ................................ ................................ ................................ ............................ 61 Metathesis of alkanes ................................ ................................ ................................ ................................ ............................ 62 Fischer -Tropsch ................................ ................................ ................................ ................................ ................................ ....... 62 Methanol to Olefins (MtO) ................................ ................................ ................................ ................................ ...................... 62 Oxidative Coupling of Methane ................................ ................................ ................................ ................................ .............. 63 Oxidative Dehydrogenation or Partial Oxidation of Hydrocarbons ................................ ................................ ......................... 63 Bioethanol dehydration ................................ ................................ ................................ ................................ .......................... 63 L11 – FRACTIONATION OF LIGHT HYDROCARBON MIXTURES ................................ ................................ .................... 64 GENERAL INFORMATION ................................ ................................ ................................ ................................ ..................... 64 Distillation: separating the problems without solving them ................................ ................................ .................... 64 THE OPERATING COLUMNS ................................ ................................ ................................ ................................ .................. 65 Demethanizer: separation of H 2 and CH 4 from the other hydrocarbons ................................ ................................ .. 65 C2 fraction: ethane -ethylene separation ................................ ................................ ................................ .................. 65 C3 fraction: propane – propylene separation ................................ ................................ ................................ ........... 65 C4 fractionation: mixture separation ................................ ................................ ................................ ........................ 66 Distillation is unfeasible ................................ ................................ ................................ ................................ .......................... 66 Extractive/azeotropic distillation ................................ ................................ ................................ ................................ ............ 66 Buta diene separation. ................................ ................................ ................................ ................................ ............................. 66 Philips Process ................................ ................................ ................................ ................................ ................................ ....66 Shell Process ................................ ................................ ................................ ................................ ................................ ....... 67 Union Carbide Process ................................ ................................ ................................ ................................ ....................... 67 Alternatives to rectification and Exxon Process. ................................ ................................ ................................ ................ 67 Isobutene separation ................................ ................................ ................................ ................................ .............................. 67 Huls process ................................ ................................ ................................ ................................ ................................ ....... 67 L12 – CH 3CHO: ACETALDEHYDE MA KING ................................ ................................ ................................ ................... 68 GENERAL INFORMATION ................................ ................................ ................................ ................................ ..................... 68 Physical Propertie s ................................ ................................ ................................ ................................ ................... 68 Chemical Properties ................................ ................................ ................................ ................................ ................. 68 Uses and Production ................................ ................................ ................................ ................................ ................ 68 THE NOT ANY MORE COMP ETITIVE PROCESSES AS A GAL -GAME ................................ ................................ ................................ ... 69 Ethanol route, the first love ................................ ................................ ................................ ................................ ...... 69 Dehydrogenation ................................ ................................ ................................ ................................ ................................ ....69 Oxidative dehydrogenation ................................ ................................ ................................ ................................ ..................... 69 Veba -Chemie process. ................................ ................................ ................................ ................................ ........................ 69 Acetylene route, t he explosive childhood friend ................................ ................................ ................................ ...... 69 C1 route, the loli ................................ ................................ ................................ ................................ ....................... 70 • from syngas ................................ ................................ ................................ ................................ ................................ ...70 • From methanol ................................ ................................ ................................ ................................ .............................. 70 Hydrocarbons route, th e stalking route ................................ ................................ ................................ ................... 70 THE WAFER WACKER PROCESS ................................ ................................ ................................ ................................ ............ 70 The Mechanism ................................ ................................ ................................ ................................ ........................ 70 Andrea Locaspi – The Beginning of the End: Industrial Organic Chemistry vi The Thermodynamics ................................ ................................ ................................ ................................ .............................. 71 The kinetics ................................ ................................ ................................ ................................ ................................ ............. 71 Processing the process ................................ ................................ ................................ ................................ ............. 71 One -stage process. ................................ ................................ ................................ ................................ ................................ ..71 Two -stages process. ................................ ................................ ................................ ................................ ................................ 72 1v2 me noob: the comparison ................................ ................................ ................................ ................................ ................ 72 L13 – C2H4O: ETHYLENE OXIDE (OXIRANE) AWAKENING ................................ ................................ ............................ 73 PHYSICAL AND CHEMICAL PROPERTIES ................................ ................................ ................................ ................................ ... 73 Safety issues ................................ ................................ ................................ ................................ ............................. 73 Yesterday is history, tomorrow is a mystery: the chlorohydrin process ................................ ................................ ... 73 BUT TODAY IS A GIFT , THAT IS WHY IT IS C ALLED PRESENT : DIRECT ETHYLENE OXIDA TION ................................ ................................ . 74 The catalyst ................................ ................................ ................................ ................................ .............................. 74 Applied mechanics mechanism ................................ ................................ ................................ ................................ 74 Mechanism with a maximum theoretical selectivity ................................ ................................ ................................ .............. 74 Mechanism without a maximum theoretical selectivity ................................ ................................ ................................ ......... 74 Operating Conditions ................................ ................................ ................................ ................................ ............... 74 Process Engineering ................................ ................................ ................................ ................................ ................. 75 Reactor engineering. ................................ ................................ ................................ ................................ ............................... 75 Oxygen -gineering ................................ ................................ ................................ ................................ ................................ ....75 Air -gineering ................................ ................................ ................................ ................................ ................................ ........... 76 L13 STILL – CH 3-C2H4O: PROPYLENE OXIDE’S COMING TO THE WORLD ................................ ................................ ...... 77 GENERAL INFORMATION ................................ ................................ ................................ ................................ ..................... 77 Physical propertie s ................................ ................................ ................................ ................................ ................... 77 Chemical properties and industrial uses ................................ ................................ ................................ .................. 77 INDUSTRIAL PRODUCTION ................................ ................................ ................................ ................................ .................... 77 Chlorohydrin Process ................................ ................................ ................................ ................................ ................ 77 Hydroperoxides pro cess ................................ ................................ ................................ ................................ ........... 78 L14 – CH 2CHCL: VINYL CHLORIDE MONOMER BIRTH ................................ ................................ ................................ ..79 GENERAL INFORMATION ................................ ................................ ................................ ................................ ..................... 79 Physical and Chemical Properties ................................ ................................ ................................ ............................. 79 Hysteria history, uses and a bit of acetylene ................................ ................................ ................................ ............ 79 The bit of acetylene. ................................ ................................ ................................ ................................ ............................... 79 Another bit but of ethylene. ................................ ................................ ................................ ................................ ................... 79 BALANCED VCM PROCESS ................................ ................................ ................................ ................................ .................. 79 1: Direct Chlorination of Ethylene ................................ ................................ ................................ ............................ 80 2: Thermal cracking of EDC ................................ ................................ ................................ ................................ ...... 80 3: Oxychlorination of ethylene ................................ ................................ ................................ ................................ . 81 Air -base d processes ................................ ................................ ................................ ................................ ................................ 81 The reactor. ................................ ................................ ................................ ................................ ................................ ........ 81 The process configuration. ................................ ................................ ................................ ................................ ................. 82 Oxygen -based processes ................................ ................................ ................................ ................................ ......................... 82 The reactor. ................................ ................................ ................................ ................................ ................................ ........ 82 The process configuration. ................................ ................................ ................................ ................................ ................. 82 L15 – STYRENE’S CREA TION ................................ ................................ ................................ ................................ ....... 83 GENERAL INFORMATION ................................ ................................ ................................ ................................ ..................... 83 ETHYL -BENZENE PROD UCTION ................................ ................................ ................................ ................................ .............. 83 The reaction ................................ ................................ ................................ ................................ ............................. 83 Monsanto -Lummus process: Alkylation with Non -Zeolite Lewis Acid catalysts ................................ ....................... 83 Catalytic catalysts. ................................ ................................ ................................ ................................ ................................ ...83 Process configuration. ................................ ................................ ................................ ................................ ............................. 84 Mobil -Badger process: Vapour -Phase Alkylation over Zeolites ................................ ................................ ................ 84 The catalysing catalyst. ................................ ................................ ................................ ................................ ........................... 84 Andrea Locaspi – The Beginning of the End: Industrial Organic Chemistry vii Process configuration. ................................ ................................ ................................ ................................ ............................. 84 Mobil -Badger process II: The Vengeance of the Liquid -Phase brother ................................ ................................ .... 85 CATALYTIC DEHYDROGENA TION OF ETHYLBENZENE ................................ ................................ ................................ ................... 85 Bits of thermodynamics ................................ ................................ ................................ ................................ ........... 85 Pieces of catalysis ................................ ................................ ................................ ................................ ..................... 85 Crumbles of plant configuration: the Monsanto process ................................ ................................ ......................... 86 The reactor. ................................ ................................ ................................ ................................ ................................ ............. 86 Overall plant. ................................ ................................ ................................ ................................ ................................ ........... 86 L16 – HOW TO: THE BL UE -EYED ULTIMATE DRA GON (POLYMERIZATION REACTIONS) ................................ .............. 87 THE ATTACK ................................ ................................ ................................ ................................ ................................ ..... 87 THE POLYMERIZATION CA RD MECHANISM ................................ ................................ ................................ ............................... 87 Chain growth ................................ ................................ ................................ ................................ ................................ ........... 87 • cationic or anionic poly merization ................................ ................................ ................................ ........................... 87 • radical polymerization, ................................ ................................ ................................ ................................ ............. 87 • coordination polymerization, ................................ ................................ ................................ ................................ ...88 THE ULTIMATE DRAGON A ND OTHER FUSION CARD S ................................ ................................ ................................ .................. 88 Polyethylene ................................ ................................ ................................ ................................ ............................. 88 LDPE production ................................ ................................ ................................ ................................ ................................ ...... 88 Reactor. ................................ ................................ ................................ ................................ ................................ .............. 88 Process configuration. ................................ ................................ ................................ ................................ ........................ 88 HDPE and LLDPE production ................................ ................................ ................................ ................................ ................... 89 Polystyrenes ................................ ................................ ................................ ................................ ............................. 89 Polystyrene and HIPS ................................ ................................ ................................ ................................ .............................. 90 GPPS plants. ................................ ................................ ................................ ................................ ................................ ....... 90 HIPS plants. ................................ ................................ ................................ ................................ ................................ ........ 90 Expanded Polystyrene EPS ................................ ................................ ................................ ................................ ...................... 90 EPS’s suspension polymerization processes ................................ ................................ ................................ ....................... 91 In the case of HIPS ................................ ................................ ................................ ................................ .............................. 91 Poly -Vinyl Chloride ................................ ................................ ................................ ................................ ................... 91 Suspension processes ................................ ................................ ................................ ................................ ............................. 91 The reactor. ................................ ................................ ................................ ................................ ................................ ........ 91 The rest of the process. ................................ ................................ ................................ ................................ ...................... 92 Emulsion processes ................................ ................................ ................................ ................................ ................................ .92 Wiki -how: the proces s (Smith -Ewart theory). ................................ ................................ ................................ .................... 92 The plant (probably even too detailed). ................................ ................................ ................................ ............................. 92 L17 – MA, MA -SELF AN D I: MALEIC ANHYDRID E ................................ ................................ ................................ ........ 93 It’s a wide world (11265) ................................ ................................ ................................ ................................ .......... 93 It’s a usele ss capitalistic world: the properties ................................ ................................ ................................ ........ 93 INDUSTRIAL PRODUCTION ................................ ................................ ................................ ................................ .................... 93 Benzene through the snow ................................ ................................ ................................ ................................ ....... 93 General thermodynamic considerations ................................ ................................ ................................ ................................ .93 Ge neral catalytic considerations ................................ ................................ ................................ ................................ ............. 93 General plant considerations ................................ ................................ ................................ ................................ .................. 93 General reactoristic considerations. ................................ ................................ ................................ ................................ ..93 General separation considerations. ................................ ................................ ................................ ................................ ...94 In a C-four open sleigh ................................ ................................ ................................ ................................ ............. 94 The catalyst, the mechanism and the unknown ................................ ................................ ................................ ..................... 94 The catalyst. ................................ ................................ ................................ ................................ ................................ ....... 94 The mechanism. ................................ ................................ ................................ ................................ ................................ .94 Back to the future catal yst. ................................ ................................ ................................ ................................ ................ 95 Through our degree we go, processing all the way ................................ ................................ ................................ ................. 95 Fix you – coldplant. ................................ ................................ ................................ ................................ ............................ 95 Fluidize you. ................................ ................................ ................................ ................................ ................................ ....... 95 Transport you. ................................ ................................ ................................ ................................ ................................ ....96 The ALMA mater process vs Benzene. ................................ ................................ ................................ ............................... 96 Andrea Locaspi – The Beginning of the End: Industrial Organic Chemistry viii L18 –PAAA PA PA PAA PA PAAA PAAAA: PHTHA LIC ANHYDRIDE ................................ ................................ ............... 97 Some Physical and Chemical properties (14438) ................................ ................................ ................................ ..... 97 PRODI ’S PROUD PRODUCTION – O-XYLENE OXIDATION ................................ ................................ ................................ .............. 97 Short thermodynamic considerations ................................ ................................ ................................ ...................... 97 Somewhat longer considerations on catalysis ................................ ................................ ................................ ......... 97 Some exceedingly flammable process considerations ................................ ................................ ............................. 98 Reactors ................................ ................................ ................................ ................................ ................................ .................. 98 Process scheme ................................ ................................ ................................ ................................ ................................ ....... 98 L19 – YOUTUBE TUTORI AL ON THE BTX FRACTI ON ................................ ................................ ................................ .... 99 BTX VS ALIPHATIC COMPOU NDS : THE LIQUID -LIQUID DIVORCE ................................ ................................ ................................ ... 99 The not so secret lover: Mrs. Solvent ................................ ................................ ................................ ....................... 99 Some juridical processes to carry the divorce (2139) ................................ ................................ ............................. 100 UDEX process ................................ ................................ ................................ ................................ ................................ ........ 100 Sulfolane process ................................ ................................ ................................ ................................ ................................ ..100 Other processes ................................ ................................ ................................ ................................ ................................ ....100 • Snamprogetti (formex, right) ................................ ................................ ................................ ................................ ..100 • Distapex (Lurgi, left) ................................ ................................ ................................ ................................ ............... 100 BTX: HOW TO SPLIT THE CHILDREN (20633) ................................ ................................ ................................ ........................ 101 Benzene and Toluene ................................ ................................ ................................ ................................ ............................ 101 O-xylene ................................ ................................ ................................ ................................ ................................ ................ 101 Ethylbenzene ................................ ................................ ................................ ................................ ................................ ......... 101 The final bosses: para a nd meta xylene ................................ ................................ ................................ ................. 101 Fractional crystallization – Krupp -Koppers process ................................ ................................ ................................ .............. 101 Equilibrium diagram. ................................ ................................ ................................ ................................ ........................ 101 Simplified process scheme. ................................ ................................ ................................ ................................ .............. 102 Phillips process. ................................ ................................ ................................ ................................ ................................ 102 Fractional Adsorptio n – Parex process ................................ ................................ ................................ ................................ ..102 The physical principle. ................................ ................................ ................................ ................................ ...................... 102 The thin line between madness and brilliance: the Parex process ................................ ................................ .................. 103 THIS IS THE END, ................................ ................................ ................................ ................................ ...................... 105 BEAUTIFUL FRIEND. ................................ ................................ ................................ ................................ ................. 105 THIS IS THE END, ................................ ................................ ................................ ................................ ...................... 105 MY ONLY FRIEND, ................................ ................................ ................................ ................................ .................... 105 THE END. ................................ ................................ ................................ .............................