TWI398435B - 醋酸及醋酸與醋酸酐之混合物之製造 - Google Patents
醋酸及醋酸與醋酸酐之混合物之製造 Download PDFInfo
- Publication number
- TWI398435B TWI398435B TW096120444A TW96120444A TWI398435B TW I398435 B TWI398435 B TW I398435B TW 096120444 A TW096120444 A TW 096120444A TW 96120444 A TW96120444 A TW 96120444A TW I398435 B TWI398435 B TW I398435B
- Authority
- TW
- Taiwan
- Prior art keywords
- acetic anhydride
- acetic acid
- liquid
- product effluent
- evaporation
- Prior art date
Links
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic acid anhydride Natural products CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 title claims description 387
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 title claims description 331
- 239000000203 mixture Substances 0.000 title claims description 58
- 238000004519 manufacturing process Methods 0.000 title claims description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 150
- 238000001704 evaporation Methods 0.000 claims description 100
- 239000000047 product Substances 0.000 claims description 99
- 230000008020 evaporation Effects 0.000 claims description 98
- 230000006315 carbonylation Effects 0.000 claims description 80
- 238000005810 carbonylation reaction Methods 0.000 claims description 80
- 239000003054 catalyst Substances 0.000 claims description 71
- 239000007788 liquid Substances 0.000 claims description 70
- 238000006243 chemical reaction Methods 0.000 claims description 45
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 45
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 39
- 238000000034 method Methods 0.000 claims description 37
- 150000001875 compounds Chemical class 0.000 claims description 36
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 30
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 29
- 239000012263 liquid product Substances 0.000 claims description 27
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 23
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 22
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 20
- 239000007858 starting material Substances 0.000 claims description 18
- 239000011541 reaction mixture Substances 0.000 claims description 13
- 239000002994 raw material Substances 0.000 claims description 10
- 238000009835 boiling Methods 0.000 claims description 8
- 238000007670 refining Methods 0.000 claims description 7
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 239000007791 liquid phase Substances 0.000 claims description 3
- 229910052762 osmium Inorganic materials 0.000 claims description 3
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims description 3
- 229910052707 ruthenium Inorganic materials 0.000 claims description 3
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 239000005864 Sulphur Substances 0.000 claims 1
- 229910002090 carbon oxide Inorganic materials 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 239000011630 iodine Substances 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 238000004064 recycling Methods 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- 239000000463 material Substances 0.000 description 12
- -1 alkali metal salts Chemical class 0.000 description 9
- 239000012043 crude product Substances 0.000 description 8
- 239000007789 gas Substances 0.000 description 8
- HSZCZNFXUDYRKD-UHFFFAOYSA-M lithium iodide Chemical compound [Li+].[I-] HSZCZNFXUDYRKD-UHFFFAOYSA-M 0.000 description 8
- 238000000926 separation method Methods 0.000 description 8
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 7
- JTXMVXSTHSMVQF-UHFFFAOYSA-N 2-acetyloxyethyl acetate Chemical compound CC(=O)OCCOC(C)=O JTXMVXSTHSMVQF-UHFFFAOYSA-N 0.000 description 6
- 239000006227 byproduct Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 238000011084 recovery Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 4
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 150000002736 metal compounds Chemical class 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- 239000011574 phosphorus Substances 0.000 description 4
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- XZXYQEHISUMZAT-UHFFFAOYSA-N 2-[(2-hydroxy-5-methylphenyl)methyl]-4-methylphenol Chemical compound CC1=CC=C(O)C(CC=2C(=CC=C(C)C=2)O)=C1 XZXYQEHISUMZAT-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 229940107816 ammonium iodide Drugs 0.000 description 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 229910000510 noble metal Inorganic materials 0.000 description 2
- 150000002897 organic nitrogen compounds Chemical class 0.000 description 2
- LSMAIBOZUPTNBR-UHFFFAOYSA-N phosphanium;iodide Chemical compound [PH4+].[I-] LSMAIBOZUPTNBR-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 150000003304 ruthenium compounds Chemical class 0.000 description 2
- QYDJCYFTRFULIB-UHFFFAOYSA-M 1,2,4-trimethylpyridin-1-ium;iodide Chemical compound [I-].CC1=CC=[N+](C)C(C)=C1 QYDJCYFTRFULIB-UHFFFAOYSA-M 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- ARSMIBSHEYKMJT-UHFFFAOYSA-M 1,3-dimethylimidazolium iodide Chemical compound [I-].CN1C=C[N+](C)=C1 ARSMIBSHEYKMJT-UHFFFAOYSA-M 0.000 description 1
- BVUPLMFUPRCOEH-UHFFFAOYSA-M 1,3-dimethylpyridin-1-ium;iodide Chemical compound [I-].CC1=CC=C[N+](C)=C1 BVUPLMFUPRCOEH-UHFFFAOYSA-M 0.000 description 1
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 description 1
- KZNJSFHJUQDYHE-UHFFFAOYSA-N 1-methylanthracene Chemical compound C1=CC=C2C=C3C(C)=CC=CC3=CC2=C1 KZNJSFHJUQDYHE-UHFFFAOYSA-N 0.000 description 1
- QAIGYXWRIHZZAA-UHFFFAOYSA-M 1-methylpyridin-1-ium;chloride Chemical compound [Cl-].C[N+]1=CC=CC=C1 QAIGYXWRIHZZAA-UHFFFAOYSA-M 0.000 description 1
- HLNJFEXZDGURGZ-UHFFFAOYSA-M 1-methylpyridin-1-ium;iodide Chemical compound [I-].C[N+]1=CC=CC=C1 HLNJFEXZDGURGZ-UHFFFAOYSA-M 0.000 description 1
- PNYRDWUKTXFTPN-UHFFFAOYSA-M 1-methylquinolin-1-ium;iodide Chemical compound [I-].C1=CC=C2[N+](C)=CC=CC2=C1 PNYRDWUKTXFTPN-UHFFFAOYSA-M 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 229910004373 HOAc Inorganic materials 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910016859 Lanthanum iodide Inorganic materials 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910001516 alkali metal iodide Inorganic materials 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- XQPRBTXUXXVTKB-UHFFFAOYSA-M caesium iodide Chemical compound [I-].[Cs+] XQPRBTXUXXVTKB-UHFFFAOYSA-M 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- NQZFAUXPNWSLBI-UHFFFAOYSA-N carbon monoxide;ruthenium Chemical group [Ru].[Ru].[Ru].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-] NQZFAUXPNWSLBI-UHFFFAOYSA-N 0.000 description 1
- 239000000306 component Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910001505 inorganic iodide Inorganic materials 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 229910052746 lanthanum Inorganic materials 0.000 description 1
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 description 1
- KYKBXWMMXCGRBA-UHFFFAOYSA-K lanthanum(3+);triiodide Chemical compound I[La](I)I KYKBXWMMXCGRBA-UHFFFAOYSA-K 0.000 description 1
- PKAUVIXBZJUYRV-UHFFFAOYSA-N methane;hydroiodide Chemical compound C.I PKAUVIXBZJUYRV-UHFFFAOYSA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 125000001477 organic nitrogen group Chemical group 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000011027 product recovery Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 1
- 125000005497 tetraalkylphosphonium group Chemical group 0.000 description 1
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
- CCIYPTIBRAUPLQ-UHFFFAOYSA-M tetrabutylphosphanium;iodide Chemical compound [I-].CCCC[P+](CCCC)(CCCC)CCCC CCIYPTIBRAUPLQ-UHFFFAOYSA-M 0.000 description 1
- JTFPRVNRGNKAAV-UHFFFAOYSA-M tetraoctylphosphanium;iodide Chemical compound [I-].CCCCCCCC[P+](CCCCCCCC)(CCCCCCCC)CCCCCCCC JTFPRVNRGNKAAV-UHFFFAOYSA-M 0.000 description 1
- AEFPPQGZJFTXDR-UHFFFAOYSA-M tetraphenylphosphanium;iodide Chemical compound [I-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 AEFPPQGZJFTXDR-UHFFFAOYSA-M 0.000 description 1
- DXJLCRNXYNRGRA-UHFFFAOYSA-M tributyl(methyl)azanium;iodide Chemical compound [I-].CCCC[N+](C)(CCCC)CCCC DXJLCRNXYNRGRA-UHFFFAOYSA-M 0.000 description 1
- RLZMYANQLOCZOB-UHFFFAOYSA-M tributyl(methyl)phosphanium;iodide Chemical compound [I-].CCCC[P+](C)(CCCC)CCCC RLZMYANQLOCZOB-UHFFFAOYSA-M 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- 238000010977 unit operation Methods 0.000 description 1
- 239000011364 vaporized material Substances 0.000 description 1
- SJHMKWQYVBZNLZ-UHFFFAOYSA-K ytterbium(3+);trihydroxide Chemical compound [OH-].[OH-].[OH-].[Yb+3] SJHMKWQYVBZNLZ-UHFFFAOYSA-K 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/54—Preparation of carboxylic acid anhydrides
- C07C51/56—Preparation of carboxylic acid anhydrides from organic acids, their salts, their esters or their halides, e.g. by carboxylation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11/423,383 US7737298B2 (en) | 2006-06-09 | 2006-06-09 | Production of acetic acid and mixtures of acetic acid and acetic anhydride |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW200804265A TW200804265A (en) | 2008-01-16 |
| TWI398435B true TWI398435B (zh) | 2013-06-11 |
Family
ID=38564364
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW096120444A TWI398435B (zh) | 2006-06-09 | 2007-06-07 | 醋酸及醋酸與醋酸酐之混合物之製造 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US7737298B2 (enExample) |
| EP (1) | EP2029514B1 (enExample) |
| JP (1) | JP5281000B2 (enExample) |
| CN (1) | CN101466659B (enExample) |
| TW (1) | TWI398435B (enExample) |
| WO (1) | WO2007145795A2 (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101659607B (zh) * | 2008-08-29 | 2013-04-10 | 上海焦化有限公司 | 制备乙酸、乙酸酐或同时制备乙酸和乙酸酐的方法 |
| US9012683B2 (en) * | 2010-11-12 | 2015-04-21 | Eastman Chemical Company | Coproduction of acetic acid and acetic anhydride |
| US8637699B2 (en) | 2011-04-15 | 2014-01-28 | Lyondell Chemical Technology, L.P. | Process for the manufacture of acetic acid |
| US9415366B2 (en) * | 2012-12-31 | 2016-08-16 | Eastman Chemical Company | Systems and methods for processing variable acetyl streams |
| US10988432B2 (en) * | 2013-03-07 | 2021-04-27 | Ineos Acetyls Uk Limited | Process for the co-production of acetic acid and acetic anhydride |
| US9908835B2 (en) | 2015-11-13 | 2018-03-06 | Celanese International Corporation | Processes for purifying acetic and hydrating anhydride |
| US9907305B2 (en) | 2016-03-22 | 2018-03-06 | Solvay Sa | Production of disinfecting solutions |
| CN114031492B (zh) * | 2021-12-13 | 2023-08-29 | 上海簇睿低碳能源技术有限公司 | 一种采用微通道反应器合成醋酸或醋酐的工艺系统及制备方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1113655A (zh) * | 1993-08-18 | 1995-12-20 | 大世吕化学工业株式会社 | 乙酸酐或乙酸酐和乙酸的制备方法 |
Family Cites Families (47)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE364254B (enExample) | 1967-04-05 | 1974-02-18 | Monsanto Co | |
| US3772380A (en) | 1970-03-12 | 1973-11-13 | Monsanto Co | Production of carboxylic acids and esters |
| US3927078A (en) | 1972-08-21 | 1975-12-16 | Chevron Res | Methylene and oxymethylene bis-ester production |
| US4559183A (en) | 1973-09-04 | 1985-12-17 | The Halcon Sd Group, Inc. | Preparation of carboxylic acid anhydrides |
| DE2450965C2 (de) | 1974-10-26 | 1983-06-09 | Hoechst Ag, 6230 Frankfurt | Verfahren zur Herstellung von Essigsäureanhydrid |
| US4115444A (en) | 1975-03-10 | 1978-09-19 | Halcon International, Inc. | Process for preparing carboxylic acid anhydrides |
| DE2836084A1 (de) | 1978-08-17 | 1980-03-06 | Hoechst Ag | Verfahren zur herstellung von essigsaeureanhydrid |
| JPS5538369A (en) | 1978-09-01 | 1980-03-17 | Texaco Development Corp | Manufacture of carboxylic acids and their esters |
| US4252741A (en) | 1978-10-06 | 1981-02-24 | Halcon Research & Development Corp. | Carbonylation with Group VIII noble metal catalysts |
| US4358411A (en) | 1979-06-29 | 1982-11-09 | The Halcon Sd Group, Inc. | Preparation of carbonylation products |
| DE2939839A1 (de) | 1979-10-02 | 1981-04-23 | Hoechst Ag, 6000 Frankfurt | Verfahren zur herstellung von essigsaeureanhydrid |
| US4417077A (en) | 1980-10-01 | 1983-11-22 | University Of Illinois Foundation | Heterogeneous anionic transition metal catalysts |
| US4374070A (en) * | 1980-11-21 | 1983-02-15 | Eastman Kodak Company | Preparation of acetic anhydride |
| US4366259A (en) | 1981-10-29 | 1982-12-28 | Texaco, Inc. | Production of acetic acid and propionic acid and their esters |
| DE3148006A1 (de) | 1981-12-04 | 1983-06-09 | Hoechst Ag, 6230 Frankfurt | Verfahren zur herstellung von essigsaeureanhydrid und/oder essigsaeure und/oder ethylidendiacetat |
| NZ203225A (en) | 1982-02-13 | 1985-01-31 | Bp Chem Int Ltd | Coproduction of monocarboxylic acids and anhydrides |
| NZ203226A (en) | 1982-02-13 | 1985-08-30 | Bp Chemical Ltd | Production of acetic anhydride from methanol and carbon monoxide |
| ZA833528B (en) | 1982-05-22 | 1984-12-24 | Bp Chem Int Ltd | Process for the production of one or more carboxylic acid anhydrides |
| EP0109212B1 (en) | 1982-11-04 | 1987-05-27 | BP Chemicals Limited | Process for the preparation of acids |
| US4629809A (en) | 1983-07-21 | 1986-12-16 | Texaco Inc. | Process for selectively preparing acetic acid by carbonylation of methanol in the presence of a novel iodide-free catalyst system |
| GB8404136D0 (en) | 1984-02-16 | 1984-03-21 | Bp Chem Int Ltd | Carbonylation process |
| US5144068A (en) | 1984-05-03 | 1992-09-01 | Hoechst Celanese Corporation | Methanol carbonylation process |
| US5003104A (en) | 1987-03-03 | 1991-03-26 | Bp Chemicals Limited | Carbonylation process and catalyst |
| GB8807284D0 (en) | 1988-03-26 | 1988-04-27 | Bp Chem Int Ltd | Chemical process |
| GB8809027D0 (en) | 1988-04-16 | 1988-05-18 | British Petroleum Co Plc | Carbonylation of allylic alcohols |
| DE3823645C1 (enExample) * | 1988-07-13 | 1989-11-30 | Hoechst Ag | |
| US5442107A (en) | 1989-04-06 | 1995-08-15 | Bp Chemicals Limited | Preparing carboxylic acids |
| JP2839367B2 (ja) | 1989-04-06 | 1998-12-16 | ビーピー ケミカルズ リミテッド | カルボン酸類の製造方法 |
| GB9021454D0 (en) | 1990-10-03 | 1990-11-14 | Bp Chem Int Ltd | Process |
| DE69108567T2 (de) | 1990-12-20 | 1995-08-03 | Eastman Chem Co | Kontinuierliches verfahren zur herstellung von essigsäureanhydrid oder einer mischung von essigsäureanhydrid und essigsäure. |
| GB9211671D0 (en) | 1992-06-02 | 1992-07-15 | Bp Chem Int Ltd | Process |
| US5488143A (en) | 1992-06-30 | 1996-01-30 | Korea Institute Of Science And Technology | Processes for the carbonylation of methanol to form acetic acid, methyl acetate and acetic anhydride |
| GB9218346D0 (en) | 1992-08-28 | 1992-10-14 | Bp Chem Int Ltd | Process |
| US5510524A (en) | 1995-02-21 | 1996-04-23 | Bp Chemicals Limited | Process for the production of a carboxylic acid |
| US5696284A (en) | 1995-06-21 | 1997-12-09 | Bp Chemicals Limited | Process for the carbonylation of alkyl alcohols and/or reactive derivatives thereof |
| US5900505A (en) | 1997-02-04 | 1999-05-04 | Eastman Chemical Company | Heterogeneous vapor phase carbonylation process |
| GB9802027D0 (en) * | 1998-01-31 | 1998-03-25 | Bp Chem Int Ltd | Chemical process |
| EP1071647A1 (en) | 1998-04-17 | 2001-01-31 | BP Chemicals Limited | Process for the production of acetic acid and/or acetic anhydride |
| US5922911A (en) | 1998-04-24 | 1999-07-13 | Eastman Chemical Company | Process for the manufacture of acetic anhydride |
| GB9816385D0 (en) | 1998-07-29 | 1998-09-23 | Bp Chem Int Ltd | Process |
| US6211405B1 (en) | 1998-10-23 | 2001-04-03 | Celanese International Corporation | Addition of iridium to the rhodium/inorganic iodide catalyst system |
| US6452043B1 (en) | 2000-04-05 | 2002-09-17 | Eastman Chemical Company | Carbonylation of lower alkyl alcohols and their derivatives using metals supported on carbonized polysulfonated divinylbenzene-styrene copolymers |
| DE10138778A1 (de) * | 2001-08-07 | 2003-02-20 | Basf Ag | Flexibles Verfahren zur gemeinsamen Herstellung von Ameisensäure sowie einer Carbonsäure mit mindestens zwei Kohlenstoffatomen und/oder deren Derivaten |
| JP3660982B2 (ja) | 2001-11-08 | 2005-06-15 | 独立行政法人産業技術総合研究所 | カルボン酸塩の製造方法 |
| US6667418B2 (en) | 2002-04-16 | 2003-12-23 | Celanese International Corporation | Oxidation treatment of a recycle stream in production of acetic acid by methanol carbonylation |
| CN1315771C (zh) | 2002-05-06 | 2007-05-16 | 伊斯曼化学公司 | 连续羰基化工艺 |
| FR2839972B1 (fr) | 2002-05-23 | 2005-08-19 | Inst Francais Du Petrole | Procede de carbonylation des alcools utilisant un catalyseur a base de rhodium ou d'iridium dans un liquide ionique non-aqueux,avec un recyclage efficace du catalyseur |
-
2006
- 2006-06-09 US US11/423,383 patent/US7737298B2/en active Active
-
2007
- 2007-05-25 CN CN200780021487.XA patent/CN101466659B/zh active Active
- 2007-05-25 JP JP2009514302A patent/JP5281000B2/ja not_active Expired - Fee Related
- 2007-05-25 EP EP07777273.9A patent/EP2029514B1/en active Active
- 2007-05-25 WO PCT/US2007/012457 patent/WO2007145795A2/en not_active Ceased
- 2007-06-07 TW TW096120444A patent/TWI398435B/zh active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1113655A (zh) * | 1993-08-18 | 1995-12-20 | 大世吕化学工业株式会社 | 乙酸酐或乙酸酐和乙酸的制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP2029514A2 (en) | 2009-03-04 |
| WO2007145795A3 (en) | 2008-03-27 |
| JP2009539835A (ja) | 2009-11-19 |
| CN101466659A (zh) | 2009-06-24 |
| EP2029514B1 (en) | 2014-10-01 |
| US20070287862A1 (en) | 2007-12-13 |
| JP5281000B2 (ja) | 2013-09-04 |
| CN101466659B (zh) | 2013-09-25 |
| WO2007145795A2 (en) | 2007-12-21 |
| TW200804265A (en) | 2008-01-16 |
| US7737298B2 (en) | 2010-06-15 |
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