DE60020128T2 - Rhodium/anorganisches iodid katalysatorsystem für das verfahren zur methanolcarbonylierung mit verbessertem verunreinigungsprofil - Google Patents
Rhodium/anorganisches iodid katalysatorsystem für das verfahren zur methanolcarbonylierung mit verbessertem verunreinigungsprofil Download PDFInfo
- Publication number
- DE60020128T2 DE60020128T2 DE60020128T DE60020128T DE60020128T2 DE 60020128 T2 DE60020128 T2 DE 60020128T2 DE 60020128 T DE60020128 T DE 60020128T DE 60020128 T DE60020128 T DE 60020128T DE 60020128 T2 DE60020128 T2 DE 60020128T2
- Authority
- DE
- Germany
- Prior art keywords
- rhodium
- hydrogen
- concentration
- iodide
- reaction
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 title claims description 78
- 238000005810 carbonylation reaction Methods 0.000 title claims description 60
- 238000000034 method Methods 0.000 title claims description 59
- 230000006315 carbonylation Effects 0.000 title claims description 51
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 title claims description 42
- 229910052703 rhodium Inorganic materials 0.000 title claims description 41
- 239000010948 rhodium Substances 0.000 title claims description 41
- 239000003054 catalyst Substances 0.000 title claims description 36
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 95
- 229910052739 hydrogen Inorganic materials 0.000 claims description 66
- 239000001257 hydrogen Substances 0.000 claims description 66
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 64
- 238000006243 chemical reaction Methods 0.000 claims description 38
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 37
- 229910001868 water Inorganic materials 0.000 claims description 37
- 239000012429 reaction media Substances 0.000 claims description 31
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 29
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 29
- 230000008569 process Effects 0.000 claims description 23
- 150000003839 salts Chemical class 0.000 claims description 22
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 18
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 18
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 18
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 14
- 229910052751 metal Inorganic materials 0.000 claims description 9
- 239000002184 metal Substances 0.000 claims description 9
- HSZCZNFXUDYRKD-UHFFFAOYSA-M lithium iodide Chemical compound [Li+].[I-] HSZCZNFXUDYRKD-UHFFFAOYSA-M 0.000 claims description 8
- 239000003381 stabilizer Substances 0.000 claims description 7
- 159000000021 acetate salts Chemical class 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
- 229910052700 potassium Inorganic materials 0.000 claims description 3
- 239000011591 potassium Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 239000011734 sodium Substances 0.000 claims description 3
- XIXADJRWDQXREU-UHFFFAOYSA-M lithium acetate Chemical compound [Li+].CC([O-])=O XIXADJRWDQXREU-UHFFFAOYSA-M 0.000 claims description 2
- 150000002739 metals Chemical class 0.000 claims description 2
- 150000004714 phosphonium salts Chemical class 0.000 claims description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 2
- 229940107816 ammonium iodide Drugs 0.000 claims 1
- LSMAIBOZUPTNBR-UHFFFAOYSA-N phosphanium;iodide Chemical compound [PH4+].[I-] LSMAIBOZUPTNBR-UHFFFAOYSA-N 0.000 claims 1
- 125000001453 quaternary ammonium group Chemical group 0.000 claims 1
- 229960000583 acetic acid Drugs 0.000 description 30
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical class CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 23
- 239000012535 impurity Substances 0.000 description 21
- 239000000047 product Substances 0.000 description 20
- 230000015572 biosynthetic process Effects 0.000 description 12
- 238000004519 manufacturing process Methods 0.000 description 11
- -1 amine compound Chemical class 0.000 description 10
- 239000006227 byproduct Substances 0.000 description 10
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 description 10
- MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 description 10
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 8
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 150000002367 halogens Chemical class 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- IQGZCSXWIRBTRW-ZZXKWVIFSA-N (2E)-2-ethyl-2-butenal Chemical compound CC\C(=C/C)C=O IQGZCSXWIRBTRW-ZZXKWVIFSA-N 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- 229910052736 halogen Inorganic materials 0.000 description 6
- 230000006872 improvement Effects 0.000 description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
- 150000001768 cations Chemical class 0.000 description 5
- 229940006461 iodide ion Drugs 0.000 description 4
- 238000011027 product recovery Methods 0.000 description 4
- 230000006641 stabilisation Effects 0.000 description 4
- 238000011105 stabilization Methods 0.000 description 4
- ANOOTOPTCJRUPK-UHFFFAOYSA-N 1-iodohexane Chemical compound CCCCCCI ANOOTOPTCJRUPK-UHFFFAOYSA-N 0.000 description 3
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ICJVSPOCMLQAJM-UHFFFAOYSA-N acetic acid;iodomethane Chemical compound IC.CC(O)=O ICJVSPOCMLQAJM-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 3
- 230000004941 influx Effects 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- HSJKGGMUJITCBW-UHFFFAOYSA-N 3-hydroxybutanal Chemical compound CC(O)CC=O HSJKGGMUJITCBW-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical class N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 238000005882 aldol condensation reaction Methods 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 150000004694 iodide salts Chemical group 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 150000002892 organic cations Chemical class 0.000 description 2
- 150000002923 oximes Chemical class 0.000 description 2
- 230000037361 pathway Effects 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical class [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical class [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001298 alcohols 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
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000001502 aryl halides Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- KMGBZBJJOKUPIA-UHFFFAOYSA-N butyl iodide Chemical compound CCCCI KMGBZBJJOKUPIA-UHFFFAOYSA-N 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 150000001767 cationic compounds Chemical class 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000011143 downstream manufacturing Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910001411 inorganic cation Inorganic materials 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 229910052757 nitrogen Chemical class 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 239000011049 pearl Substances 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Chemical class 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 150000003283 rhodium Chemical class 0.000 description 1
- 150000003284 rhodium compounds Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (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 |
|---|---|---|---|
| US09/386,708 US6303813B1 (en) | 1999-08-31 | 1999-08-31 | Rhodium/inorganic iodide catalyst system for methanol carbonylation process with improved impurity profile |
| US386708 | 1999-08-31 | ||
| PCT/US2000/021562 WO2001016070A1 (en) | 1999-08-31 | 2000-08-07 | Rhodium/inorganic iodide catalyst system for methanol carbonylation process with improved impurity profile |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60020128D1 DE60020128D1 (de) | 2005-06-16 |
| DE60020128T2 true DE60020128T2 (de) | 2006-02-23 |
Family
ID=23526710
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60020128T Expired - Lifetime DE60020128T2 (de) | 1999-08-31 | 2000-08-07 | Rhodium/anorganisches iodid katalysatorsystem für das verfahren zur methanolcarbonylierung mit verbessertem verunreinigungsprofil |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US6303813B1 (enExample) |
| EP (1) | EP1208073B1 (enExample) |
| JP (1) | JP4994549B2 (enExample) |
| KR (1) | KR100651455B1 (enExample) |
| CN (1) | CN1185198C (enExample) |
| AR (1) | AR025310A1 (enExample) |
| AT (1) | ATE295342T1 (enExample) |
| AU (1) | AU775283B2 (enExample) |
| BR (1) | BR0013463A (enExample) |
| CA (1) | CA2381420C (enExample) |
| CZ (1) | CZ2002753A3 (enExample) |
| DE (1) | DE60020128T2 (enExample) |
| ES (1) | ES2240139T3 (enExample) |
| MX (1) | MXPA02002255A (enExample) |
| MY (1) | MY131985A (enExample) |
| NO (1) | NO327989B1 (enExample) |
| NZ (1) | NZ517677A (enExample) |
| PL (1) | PL199388B1 (enExample) |
| RS (1) | RS50170B (enExample) |
| RU (1) | RU2240305C2 (enExample) |
| TR (1) | TR200200545T2 (enExample) |
| TW (1) | TW506964B (enExample) |
| UA (1) | UA70385C2 (enExample) |
| WO (1) | WO2001016070A1 (enExample) |
| ZA (1) | ZA200200935B (enExample) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US7820855B2 (en) | 2008-04-29 | 2010-10-26 | Celanese International Corporation | Method and apparatus for carbonylating methanol with acetic acid enriched flash stream |
| US8785684B2 (en) | 2010-06-14 | 2014-07-22 | Celanese International Corporation | Methanol carbonylation process with rhodium catalyst, an iodide salt and a metallic co-catalyst selected from transition metals, indium, strontium, barium, zinc, tin and heteropoly acids |
| US8835681B2 (en) | 2010-06-14 | 2014-09-16 | Celanese International Corporation | Methanol carbonylation process with rhodium catalyst and a lanthanide metal co-catalyst |
| CN103038206B (zh) | 2010-06-14 | 2016-10-05 | 塞拉尼斯国际公司 | 羰基化方法 |
| MX340954B (es) | 2010-12-15 | 2016-07-29 | Daicel Corp | Procedimiento para producir acido acetico. |
| MY161203A (en) | 2010-12-15 | 2017-04-14 | Daicel Corp | Process for producing acetic acid |
| US8916727B2 (en) | 2011-12-16 | 2014-12-23 | Celanese International Corporation | Production of acetic acid with enhanced catalyst stability |
| TWI547477B (zh) | 2012-03-14 | 2016-09-01 | 大賽璐股份有限公司 | 醋酸之製造方法 |
| US9409846B2 (en) | 2013-03-15 | 2016-08-09 | Celanese International Corporation | Process for separating product gas using carbonylation processes |
| US9540304B2 (en) * | 2014-11-14 | 2017-01-10 | Celanese International Corporation | Processes for producing an acetic acid product having low butyl acetate content |
| EP3218347B1 (en) | 2014-11-14 | 2020-04-29 | Celanese International Corporation | Processes for producing acetic acid from a reaction medium having low ethyl iodide content |
| US9302969B1 (en) * | 2014-11-14 | 2016-04-05 | Celanese International Corporation | Processes for producing acetic acid by introducing a lithium compound |
| JP6738330B2 (ja) * | 2014-11-14 | 2020-08-12 | セラニーズ・インターナショナル・コーポレーション | 鉄の除去による酢酸収量の改良法 |
| US9260369B1 (en) | 2014-11-14 | 2016-02-16 | Celanese International Corporation | Processes for producing acetic acid product having low butyl acetate content |
| US9340481B1 (en) | 2014-11-14 | 2016-05-17 | Celanese International Corporation | Process for flashing a reaction medium comprising lithium acetate |
| US9540303B2 (en) | 2015-04-01 | 2017-01-10 | Celanese International Corporation | Processes for producing acetic acid |
| US9416088B1 (en) | 2015-10-02 | 2016-08-16 | Celanese International Corporation | Process to produce acetic acid with recycle of water |
| US9957216B2 (en) | 2015-11-13 | 2018-05-01 | Celanese International Corporation | Processes for producing acetic acid |
| BR112019017835A2 (pt) * | 2017-03-08 | 2020-04-14 | Daicel Corp | método para produzir ácido acético |
| US10550058B2 (en) | 2017-03-08 | 2020-02-04 | Daicel Corporation | Method for producing acetic acid |
| SG11201908724VA (en) | 2017-03-22 | 2019-10-30 | Daicel Corp | Method for producing acetic acid |
| CN107141213A (zh) * | 2017-05-24 | 2017-09-08 | 北京三聚环保新材料股份有限公司 | 一种甲醇羰基化合成醋酸的方法 |
| JP6626987B1 (ja) * | 2018-05-29 | 2019-12-25 | 株式会社ダイセル | 酢酸の製造方法 |
| CN116217369A (zh) * | 2022-12-30 | 2023-06-06 | 江苏索普化工股份有限公司 | 一种提高甲醇低压羰基合成醋酸中三碘化铑溶解度的方法 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3769329A (en) | 1970-03-12 | 1973-10-30 | Monsanto Co | Production of carboxylic acids and esters |
| US5144068A (en) | 1984-05-03 | 1992-09-01 | Hoechst Celanese Corporation | Methanol carbonylation process |
| US5026908A (en) | 1984-05-03 | 1991-06-25 | Hoechst Celanese Corporation | Methanol carbonylation process |
| US5001259A (en) | 1984-05-03 | 1991-03-19 | Hoechst Celanese Corporation | Methanol carbonylation process |
| CA1299195C (en) | 1986-06-16 | 1992-04-21 | G. Paull Torrence | Addition of hydrogen to carbon monoxide feed gas in producing acetic acid by carbonylation of methanol |
| JP3500150B2 (ja) * | 1993-08-18 | 2004-02-23 | ダイセル化学工業株式会社 | 無水酢酸又は無水酢酸及び酢酸の製造方法 |
| FR2711365B1 (fr) * | 1993-10-19 | 1995-12-15 | Rhone Poulenc Chimie | Procédé d'hydroxycarbonylation du butadiène. |
| SG44317A1 (en) | 1994-06-15 | 1997-12-19 | Daicel Chem | Process for producing high purity acetic acid |
| GB9503382D0 (en) * | 1995-02-21 | 1995-04-12 | Bp Chem Int Ltd | Process |
| IN192600B (enExample) | 1996-10-18 | 2004-05-08 | Hoechst Celanese Corp | |
| JPH10231267A (ja) * | 1997-02-19 | 1998-09-02 | Chiyoda Corp | 有機カルボン酸の製造方法 |
| GB9712601D0 (en) * | 1997-06-16 | 1997-08-20 | Bp Chem Int Ltd | Chemical process |
| GB9816564D0 (en) * | 1998-07-31 | 1998-09-30 | Bp Chem Int Ltd | Process |
-
1999
- 1999-08-31 US US09/386,708 patent/US6303813B1/en not_active Expired - Lifetime
-
2000
- 2000-07-08 UA UA2002021703A patent/UA70385C2/uk unknown
- 2000-08-07 KR KR1020027002419A patent/KR100651455B1/ko not_active Expired - Fee Related
- 2000-08-07 BR BR0013463-5A patent/BR0013463A/pt not_active Application Discontinuation
- 2000-08-07 ES ES00952611T patent/ES2240139T3/es not_active Expired - Lifetime
- 2000-08-07 PL PL353356A patent/PL199388B1/pl not_active IP Right Cessation
- 2000-08-07 TR TR2002/00545T patent/TR200200545T2/xx unknown
- 2000-08-07 DE DE60020128T patent/DE60020128T2/de not_active Expired - Lifetime
- 2000-08-07 AU AU65277/00A patent/AU775283B2/en not_active Ceased
- 2000-08-07 NZ NZ517677A patent/NZ517677A/en not_active IP Right Cessation
- 2000-08-07 AT AT00952611T patent/ATE295342T1/de active
- 2000-08-07 CZ CZ2002753A patent/CZ2002753A3/cs unknown
- 2000-08-07 CN CNB008122628A patent/CN1185198C/zh not_active Expired - Fee Related
- 2000-08-07 MX MXPA02002255A patent/MXPA02002255A/es active IP Right Grant
- 2000-08-07 RS YUP-115/02A patent/RS50170B/sr unknown
- 2000-08-07 CA CA002381420A patent/CA2381420C/en not_active Expired - Fee Related
- 2000-08-07 RU RU2002107997/04A patent/RU2240305C2/ru not_active IP Right Cessation
- 2000-08-07 JP JP2001519640A patent/JP4994549B2/ja not_active Expired - Lifetime
- 2000-08-07 WO PCT/US2000/021562 patent/WO2001016070A1/en not_active Ceased
- 2000-08-07 EP EP00952611A patent/EP1208073B1/en not_active Expired - Lifetime
- 2000-08-17 AR ARP000104257A patent/AR025310A1/es active IP Right Grant
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- 2000-08-29 MY MYPI20003980A patent/MY131985A/en unknown
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