ES2846182T3 - Procesos para producir un producto de ácido acético con bajo contenido de acetato de butilo - Google Patents
Procesos para producir un producto de ácido acético con bajo contenido de acetato de butilo Download PDFInfo
- Publication number
- ES2846182T3 ES2846182T3 ES15778587T ES15778587T ES2846182T3 ES 2846182 T3 ES2846182 T3 ES 2846182T3 ES 15778587 T ES15778587 T ES 15778587T ES 15778587 T ES15778587 T ES 15778587T ES 2846182 T3 ES2846182 T3 ES 2846182T3
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- weight
- acetic acid
- equal
- stream
- ppm
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 85
- 230000008569 process Effects 0.000 title claims abstract description 77
- GRFKUEDWLAGOJX-UHFFFAOYSA-N acetic acid;butyl acetate Chemical compound CC(O)=O.CCCCOC(C)=O GRFKUEDWLAGOJX-UHFFFAOYSA-N 0.000 title description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 732
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims abstract description 170
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 156
- 239000012429 reaction media Substances 0.000 claims abstract description 138
- 229910052751 metal Inorganic materials 0.000 claims abstract description 92
- 239000002184 metal Substances 0.000 claims abstract description 92
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 77
- 239000003054 catalyst Substances 0.000 claims abstract description 72
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims abstract description 71
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims abstract description 71
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims abstract description 69
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims abstract description 60
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims abstract description 60
- HSZCZNFXUDYRKD-UHFFFAOYSA-M lithium iodide Chemical compound [Li+].[I-] HSZCZNFXUDYRKD-UHFFFAOYSA-M 0.000 claims abstract description 57
- 239000010948 rhodium Substances 0.000 claims abstract description 54
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims abstract description 54
- 229910052703 rhodium Inorganic materials 0.000 claims abstract description 53
- 238000005810 carbonylation reaction Methods 0.000 claims abstract description 52
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 52
- 239000001257 hydrogen Substances 0.000 claims abstract description 52
- 230000036961 partial effect Effects 0.000 claims abstract description 48
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 47
- 230000006315 carbonylation Effects 0.000 claims abstract description 46
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims abstract description 44
- 238000006243 chemical reaction Methods 0.000 claims abstract description 40
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims abstract description 37
- 229910002091 carbon monoxide Inorganic materials 0.000 claims abstract description 37
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 48
- 239000007791 liquid phase Substances 0.000 claims description 48
- 239000007788 liquid Substances 0.000 claims description 32
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 31
- 238000005260 corrosion Methods 0.000 claims description 28
- 230000007797 corrosion Effects 0.000 claims description 28
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 25
- 239000003456 ion exchange resin Substances 0.000 claims description 25
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 25
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 21
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 19
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 18
- 229910052744 lithium Inorganic materials 0.000 claims description 16
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 14
- 229910052759 nickel Inorganic materials 0.000 claims description 13
- 229910052742 iron Inorganic materials 0.000 claims description 11
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 10
- 229910052804 chromium Inorganic materials 0.000 claims description 10
- 239000011651 chromium Substances 0.000 claims description 10
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 claims description 10
- 229910052753 mercury Inorganic materials 0.000 claims description 10
- 229910052709 silver Inorganic materials 0.000 claims description 10
- 239000004332 silver Substances 0.000 claims description 10
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 9
- 229910052750 molybdenum Inorganic materials 0.000 claims description 9
- 229910052763 palladium Inorganic materials 0.000 claims description 9
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 8
- 239000011733 molybdenum Substances 0.000 claims description 8
- 239000000047 product Substances 0.000 description 176
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 47
- 238000004821 distillation Methods 0.000 description 47
- 150000002739 metals Chemical class 0.000 description 34
- 238000009835 boiling Methods 0.000 description 29
- 239000012535 impurity Substances 0.000 description 26
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 24
- 235000019260 propionic acid Nutrition 0.000 description 24
- 239000000203 mixture Substances 0.000 description 23
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 23
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 22
- 229910000043 hydrogen iodide Inorganic materials 0.000 description 19
- 239000012071 phase Substances 0.000 description 19
- XIXADJRWDQXREU-UHFFFAOYSA-M lithium acetate Chemical compound [Li+].CC([O-])=O XIXADJRWDQXREU-UHFFFAOYSA-M 0.000 description 17
- 239000011347 resin Substances 0.000 description 17
- 229920005989 resin Polymers 0.000 description 17
- 238000001035 drying Methods 0.000 description 15
- 150000004694 iodide salts Chemical class 0.000 description 15
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 11
- 239000006227 byproduct Substances 0.000 description 11
- 150000001768 cations Chemical class 0.000 description 11
- -1 halide salt Chemical class 0.000 description 11
- 238000000605 extraction Methods 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 10
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 9
- 239000007789 gas Substances 0.000 description 9
- 238000000746 purification Methods 0.000 description 9
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 238000001704 evaporation Methods 0.000 description 8
- 230000008020 evaporation Effects 0.000 description 8
- 229940006461 iodide ion Drugs 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 150000002642 lithium compounds Chemical class 0.000 description 7
- 238000000926 separation method Methods 0.000 description 7
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 150000001351 alkyl iodides Chemical class 0.000 description 6
- 229910045601 alloy Inorganic materials 0.000 description 6
- 239000000956 alloy Substances 0.000 description 6
- 150000004820 halides Chemical class 0.000 description 6
- 230000008901 benefit Effects 0.000 description 5
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 description 5
- MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 150000002431 hydrogen Chemical class 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 4
- 239000012295 chemical reaction liquid Substances 0.000 description 4
- 239000000356 contaminant Substances 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- 238000005882 aldol condensation reaction Methods 0.000 description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 239000001569 carbon dioxide Substances 0.000 description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- 230000015556 catabolic process Effects 0.000 description 3
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- 238000006731 degradation reaction Methods 0.000 description 3
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- 239000010935 stainless steel Substances 0.000 description 3
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- 239000002699 waste material Substances 0.000 description 3
- IQGZCSXWIRBTRW-ZZXKWVIFSA-N (2E)-2-ethyl-2-butenal Chemical compound CC\C(=C/C)C=O IQGZCSXWIRBTRW-ZZXKWVIFSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000001350 alkyl halides Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
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- 230000002051 biphasic effect Effects 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 229940023913 cation exchange resins Drugs 0.000 description 2
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- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 229940071870 hydroiodic acid Drugs 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 229910001511 metal iodide Inorganic materials 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
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- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- 229910052726 zirconium Inorganic materials 0.000 description 2
- ANOOTOPTCJRUPK-UHFFFAOYSA-N 1-iodohexane Chemical compound CCCCCCI ANOOTOPTCJRUPK-UHFFFAOYSA-N 0.000 description 1
- BLXSFCHWMBESKV-UHFFFAOYSA-N 1-iodopentane Chemical compound CCCCCI BLXSFCHWMBESKV-UHFFFAOYSA-N 0.000 description 1
- UNNGUFMVYQJGTD-UHFFFAOYSA-N 2-Ethylbutanal Chemical compound CCC(CC)C=O UNNGUFMVYQJGTD-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 229910000838 Al alloy Inorganic materials 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229910000640 Fe alloy Inorganic materials 0.000 description 1
- 229910004373 HOAc Inorganic materials 0.000 description 1
- 229910013594 LiOAc Inorganic materials 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910001069 Ti alloy Inorganic materials 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 238000002479 acid--base titration Methods 0.000 description 1
- 238000010669 acid-base reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910001516 alkali metal iodide Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001347 alkyl bromides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000001502 aryl halides Chemical class 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- KMGBZBJJOKUPIA-UHFFFAOYSA-N butyl iodide Chemical compound CCCCI KMGBZBJJOKUPIA-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000005341 cation exchange Methods 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
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- 230000003247 decreasing effect Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
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- 238000005869 desulfonation reaction Methods 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 229910000856 hastalloy Inorganic materials 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 229910001026 inconel Inorganic materials 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical class [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- IAQLJCYTGRMXMA-UHFFFAOYSA-M lithium;acetate;dihydrate Chemical compound [Li+].O.O.CC([O-])=O IAQLJCYTGRMXMA-UHFFFAOYSA-M 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 239000003863 metallic catalyst Substances 0.000 description 1
- 238000005272 metallurgy Methods 0.000 description 1
- VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 description 1
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 description 1
- PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 1
- 150000002892 organic cations Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000006464 oxidative addition reaction Methods 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 238000003918 potentiometric titration Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
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- 230000000717 retained effect Effects 0.000 description 1
- 150000003304 ruthenium compounds Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
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- 238000011105 stabilization Methods 0.000 description 1
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- 229910052719 titanium Inorganic materials 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/10—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction with carbon monoxide
- C07C51/12—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction with carbon monoxide on an oxygen-containing group in organic compounds, e.g. alcohols
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
- B01J23/46—Ruthenium, rhodium, osmium or iridium
- B01J23/464—Rhodium
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
- C07C51/44—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation by distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/50—Use of additives, e.g. for stabilisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
- C07C53/08—Acetic acid
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Crystallography & Structural Chemistry (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201462079991P | 2014-11-14 | 2014-11-14 | |
| US14/694,932 US9260369B1 (en) | 2014-11-14 | 2015-04-23 | Processes for producing acetic acid product having low butyl acetate content |
| PCT/US2015/053843 WO2016076972A1 (en) | 2014-11-14 | 2015-10-02 | Processes for producing an acetic acid product having low butyl acetate content |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2846182T3 true ES2846182T3 (es) | 2021-07-28 |
Family
ID=55275322
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES15778587T Active ES2846182T3 (es) | 2014-11-14 | 2015-10-02 | Procesos para producir un producto de ácido acético con bajo contenido de acetato de butilo |
Country Status (12)
| Country | Link |
|---|---|
| US (4) | US9260369B1 (enExample) |
| EP (1) | EP3218344B1 (enExample) |
| JP (3) | JP2016094384A (enExample) |
| KR (1) | KR102465082B1 (enExample) |
| CN (2) | CN116143604A (enExample) |
| ES (1) | ES2846182T3 (enExample) |
| MX (1) | MX380593B (enExample) |
| MY (1) | MY181881A (enExample) |
| RS (1) | RS61473B1 (enExample) |
| SA (1) | SA517381516B1 (enExample) |
| SG (1) | SG11201703427QA (enExample) |
| WO (1) | WO2016076972A1 (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9260369B1 (en) | 2014-11-14 | 2016-02-16 | Celanese International Corporation | Processes for producing acetic acid product having low butyl acetate content |
| US9540304B2 (en) | 2014-11-14 | 2017-01-10 | Celanese International Corporation | Processes for producing an acetic acid product having low butyl acetate content |
| ES2772775T3 (es) | 2017-01-18 | 2020-07-08 | Daicel Corp | Método de producción de ácido acético |
| US10457622B2 (en) | 2017-03-08 | 2019-10-29 | Daicel Corporation | Method for producing acetic acid |
| WO2018163448A1 (ja) * | 2017-03-08 | 2018-09-13 | 株式会社ダイセル | 酢酸の製造方法 |
| EP3398930B1 (en) | 2017-03-22 | 2019-11-20 | Daicel Corporation | Method for producing acetic acid |
| JP6588657B1 (ja) * | 2018-05-02 | 2019-10-09 | 株式会社ダイセル | 酢酸の製造方法 |
| WO2019229857A1 (ja) * | 2018-05-29 | 2019-12-05 | 株式会社ダイセル | 酢酸の製造方法 |
| CN110325503B (zh) * | 2018-05-29 | 2023-05-02 | 株式会社大赛璐 | 乙酸的制备方法 |
Family Cites Families (62)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3769329A (en) | 1970-03-12 | 1973-10-30 | Monsanto Co | Production of carboxylic acids and esters |
| FR2496644A1 (fr) | 1980-12-24 | 1982-06-25 | Rhone Poulenc Ind | Procede de preparation de l'anhydride acetique |
| US4733006A (en) | 1980-12-29 | 1988-03-22 | Monsanto Company | Carbonylation process with an alkali metal acetate as catalyst stabilizer |
| US4792620A (en) * | 1983-10-14 | 1988-12-20 | Bp Chemicals Limited | Carbonylation catalysts |
| US5001259A (en) | 1984-05-03 | 1991-03-19 | Hoechst Celanese Corporation | Methanol carbonylation process |
| US5026908A (en) | 1984-05-03 | 1991-06-25 | Hoechst Celanese Corporation | Methanol carbonylation process |
| US5144068A (en) | 1984-05-03 | 1992-09-01 | Hoechst Celanese Corporation | Methanol carbonylation process |
| US4615806B1 (en) | 1985-03-07 | 1994-05-03 | Hoechst Co American | Removal of iodide compounds from non-aqueous organic media |
| JPH0487284A (ja) | 1990-07-30 | 1992-03-19 | Mitsubishi Electric Corp | 避雷器切離し装置 |
| AU8790391A (en) | 1990-11-19 | 1992-05-21 | Hoechst Celanese Corporation | Removal of carbonyl impurities from a carbonylation process stream |
| CA2093752C (en) | 1992-04-15 | 1999-06-15 | David W. Studer | Integrated process for oxygenated acetyl compounds from synthesis gas via dimethyl ether |
| GB9211671D0 (en) | 1992-06-02 | 1992-07-15 | Bp Chem Int Ltd | Process |
| US5672743A (en) | 1993-09-10 | 1997-09-30 | Bp Chemicals Limited | Process for the production of acetic acid |
| JP3377555B2 (ja) | 1993-05-31 | 2003-02-17 | ダイセル化学工業株式会社 | カルボニル化反応生成物に含有されるヨウ素化合物の除去方法 |
| JP3244351B2 (ja) | 1993-07-08 | 2002-01-07 | ダイセル化学工業株式会社 | 高純度酢酸の製造方法 |
| TW283702B (enExample) | 1993-07-08 | 1996-08-21 | Daicel Chem | |
| JP3244350B2 (ja) | 1993-07-08 | 2002-01-07 | ダイセル化学工業株式会社 | 高純度酢酸の製造方法 |
| JP3581725B2 (ja) * | 1994-06-30 | 2004-10-27 | ダイセル化学工業株式会社 | アセトアルデヒドとヨウ化メチルの分離方法 |
| US5625095A (en) * | 1994-06-15 | 1997-04-29 | Daicel Chemical Industries, Ltd. | Process for producing high purity acetic acid |
| JP3244385B2 (ja) * | 1994-06-15 | 2002-01-07 | ダイセル化学工業株式会社 | 高純度酢酸の製造方法 |
| US5696284A (en) | 1995-06-21 | 1997-12-09 | Bp Chemicals Limited | Process for the carbonylation of alkyl alcohols and/or reactive derivatives thereof |
| US5783731A (en) | 1995-09-11 | 1998-07-21 | Hoechst Celanese Corporation | Removal of carbonyl impurities from a carbonylation process stream |
| IN189249B (enExample) | 1995-10-27 | 2003-01-18 | Hoechst Celanese Corp | |
| US6339171B1 (en) | 1996-10-18 | 2002-01-15 | Celanese International Corporation | Removal or reduction of permanganate reducing compounds and alkyl iodides from a carbonylation process stream |
| IN192600B (enExample) | 1996-10-18 | 2004-05-08 | Hoechst Celanese Corp | |
| GB9625335D0 (en) | 1996-12-05 | 1997-01-22 | Bp Chem Int Ltd | Process |
| GB9626428D0 (en) | 1996-12-19 | 1997-02-05 | Bp Chem Int Ltd | Process |
| GB9626429D0 (en) | 1996-12-19 | 1997-02-05 | Bp Chem Int Ltd | Process |
| GB9626317D0 (en) | 1996-12-19 | 1997-02-05 | Bp Chem Int Ltd | Process |
| SG65716A1 (en) | 1996-12-30 | 1999-06-22 | Chiyoda Chem Eng Construct Co | Process for the production of carbonyl compound |
| JPH10231267A (ja) | 1997-02-19 | 1998-09-02 | Chiyoda Corp | 有機カルボン酸の製造方法 |
| JPH10237009A (ja) | 1997-02-28 | 1998-09-08 | Mitsubishi Gas Chem Co Inc | ギ酸メチルからの酢酸の製造方法 |
| CN1295551A (zh) | 1998-03-31 | 2001-05-16 | 哈尔多·托普森公司 | 生产乙酸的方法 |
| US6211405B1 (en) | 1998-10-23 | 2001-04-03 | Celanese International Corporation | Addition of iridium to the rhodium/inorganic iodide catalyst system |
| US6303813B1 (en) * | 1999-08-31 | 2001-10-16 | Celanese International Corporation | Rhodium/inorganic iodide catalyst system for methanol carbonylation process with improved impurity profile |
| US6225498B1 (en) | 2000-03-24 | 2001-05-01 | Celanese International Corporation | Method of removing organic iodides from organic media |
| US6657078B2 (en) * | 2001-02-07 | 2003-12-02 | Celanese International Corporation | Low energy carbonylation process |
| JP2004131389A (ja) | 2002-10-08 | 2004-04-30 | Daicel Chem Ind Ltd | カルボン酸の製造方法及び製造システム |
| US7005541B2 (en) | 2002-12-23 | 2006-02-28 | Celanese International Corporation | Low water methanol carbonylation process for high acetic acid production and for water balance control |
| US7223886B2 (en) | 2004-03-02 | 2007-05-29 | Celanese International Corporation | Removal of permanganate reducing compounds from methanol carbonylation process stream |
| US7223883B2 (en) | 2004-03-02 | 2007-05-29 | Celanese International Corporation | Removal of permanganate reducing compounds from methanol carbonylation process stream |
| JP4526381B2 (ja) | 2004-12-27 | 2010-08-18 | ダイセル化学工業株式会社 | 酢酸の製造方法 |
| US7855306B2 (en) | 2005-04-28 | 2010-12-21 | Celanese International Corporation | Process for the production of acetic acid |
| US7989659B2 (en) | 2007-05-17 | 2011-08-02 | Celanese International Corporation | Method and apparatus for making acetic acid with improved light ends column productivity |
| WO2008153708A2 (en) * | 2007-05-21 | 2008-12-18 | Celanese International Corporation | Reaction product of rhodium-catalyzed methanol carbonylation |
| US8062482B2 (en) | 2007-10-30 | 2011-11-22 | Celanese International Corporation | Acetaldehyde removal from methyl acetate by distillation at elevated pressure |
| MX2010011850A (es) | 2008-04-29 | 2010-11-30 | Celanese Int Corp | Sistema de carbonilacion de metanol que tiene un absorbedor con multiples opciones de disolvente. |
| US7884237B2 (en) | 2008-11-07 | 2011-02-08 | Celanese International Corp. | Methanol carbonylation with improved aldehyde removal |
| WO2011146446A1 (en) | 2010-05-18 | 2011-11-24 | Celanese International Corporation | Process for purifying acetic acid streams by removing permanganate reducing compounds |
| US8957248B2 (en) | 2010-07-26 | 2015-02-17 | Daicel Corporation | Process for producing acetic acid |
| ES2702766T3 (es) | 2010-10-06 | 2019-03-05 | Daicel Corp | Proceso de producción de ácido acético |
| WO2012081417A1 (ja) | 2010-12-15 | 2012-06-21 | 株式会社ダイセル | 酢酸の製造方法 |
| WO2012081416A1 (ja) | 2010-12-15 | 2012-06-21 | 株式会社ダイセル | 酢酸の製造方法 |
| MY161174A (en) | 2010-12-15 | 2017-04-14 | Daicel Corp | Process for producing acetic acid |
| MX338850B (es) | 2010-12-24 | 2016-05-02 | Daicel Corp | Procedimiento para producir acido acetico. |
| TWI547477B (zh) | 2012-03-14 | 2016-09-01 | 大賽璐股份有限公司 | 醋酸之製造方法 |
| US9193657B2 (en) | 2012-08-17 | 2015-11-24 | Celanese International Corporation | Catalyst stability in carbonylation processes |
| JP6291420B2 (ja) | 2012-12-21 | 2018-03-14 | 株式会社ダイセル | 酢酸の製造方法 |
| AR094541A1 (es) | 2013-01-25 | 2015-08-12 | Daicel Corp | Procedimiento para producir ácido carboxílico |
| US9260369B1 (en) | 2014-11-14 | 2016-02-16 | Celanese International Corporation | Processes for producing acetic acid product having low butyl acetate content |
| EP3219699B1 (en) | 2015-09-29 | 2020-04-15 | Daicel Corporation | Method of producing acetic acid |
| CN108368018B (zh) | 2016-03-01 | 2022-01-21 | 株式会社大赛璐 | 乙酸制造方法 |
-
2015
- 2015-04-23 US US14/694,932 patent/US9260369B1/en active Active
- 2015-05-19 JP JP2015101746A patent/JP2016094384A/ja active Pending
- 2015-10-02 RS RS20210221A patent/RS61473B1/sr unknown
- 2015-10-02 SG SG11201703427QA patent/SG11201703427QA/en unknown
- 2015-10-02 WO PCT/US2015/053843 patent/WO2016076972A1/en not_active Ceased
- 2015-10-02 CN CN202310216130.8A patent/CN116143604A/zh active Pending
- 2015-10-02 ES ES15778587T patent/ES2846182T3/es active Active
- 2015-10-02 KR KR1020177016368A patent/KR102465082B1/ko active Active
- 2015-10-02 CN CN201580068310.XA patent/CN107108433A/zh active Pending
- 2015-10-02 MX MX2017006297A patent/MX380593B/es unknown
- 2015-10-02 MY MYPI2017701673A patent/MY181881A/en unknown
- 2015-10-02 EP EP15778587.4A patent/EP3218344B1/en active Active
-
2016
- 2016-02-12 US US15/042,588 patent/US9776942B2/en active Active
-
2017
- 2017-05-11 SA SA517381516A patent/SA517381516B1/ar unknown
- 2017-07-19 JP JP2017140229A patent/JP7108385B2/ja active Active
- 2017-08-25 US US15/686,356 patent/US10173955B2/en active Active
-
2018
- 2018-12-04 US US16/209,355 patent/US11014867B2/en active Active
-
2022
- 2022-05-17 JP JP2022080674A patent/JP2022110086A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| EP3218344B1 (en) | 2020-11-25 |
| US20190119190A1 (en) | 2019-04-25 |
| CN107108433A (zh) | 2017-08-29 |
| EP3218344A1 (en) | 2017-09-20 |
| US9260369B1 (en) | 2016-02-16 |
| US20160159721A1 (en) | 2016-06-09 |
| MY181881A (en) | 2021-01-12 |
| CN116143604A (zh) | 2023-05-23 |
| US20170349522A1 (en) | 2017-12-07 |
| SG11201703427QA (en) | 2017-05-30 |
| JP2018030831A (ja) | 2018-03-01 |
| US10173955B2 (en) | 2019-01-08 |
| SA517381516B1 (ar) | 2021-11-24 |
| RS61473B1 (sr) | 2021-03-31 |
| KR102465082B1 (ko) | 2022-11-09 |
| MX2017006297A (es) | 2017-08-21 |
| MX380593B (es) | 2025-03-12 |
| US9776942B2 (en) | 2017-10-03 |
| JP7108385B2 (ja) | 2022-07-28 |
| JP2022110086A (ja) | 2022-07-28 |
| US11014867B2 (en) | 2021-05-25 |
| JP2016094384A (ja) | 2016-05-26 |
| WO2016076972A1 (en) | 2016-05-19 |
| KR20170083617A (ko) | 2017-07-18 |
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