JPH0352452B2 - - Google Patents
Info
- Publication number
- JPH0352452B2 JPH0352452B2 JP57163034A JP16303482A JPH0352452B2 JP H0352452 B2 JPH0352452 B2 JP H0352452B2 JP 57163034 A JP57163034 A JP 57163034A JP 16303482 A JP16303482 A JP 16303482A JP H0352452 B2 JPH0352452 B2 JP H0352452B2
- Authority
- JP
- Japan
- Prior art keywords
- methanol
- methyl acetate
- reaction
- mixture
- carbon monoxide
- 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 claims description 80
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 66
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 65
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 26
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 25
- 239000000203 mixture Substances 0.000 claims description 20
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 19
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 18
- 238000004519 manufacturing process Methods 0.000 claims description 14
- 239000007789 gas Substances 0.000 claims description 12
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 11
- 229910052804 chromium Inorganic materials 0.000 claims description 11
- 239000011651 chromium Substances 0.000 claims description 11
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 9
- 150000003003 phosphines Chemical class 0.000 claims description 9
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 8
- 150000002497 iodine compounds Chemical class 0.000 claims description 8
- 229910052703 rhodium Inorganic materials 0.000 claims description 7
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 239000010948 rhodium Substances 0.000 claims description 5
- 239000007791 liquid phase Substances 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 23
- 239000011541 reaction mixture Substances 0.000 description 10
- 239000003054 catalyst Substances 0.000 description 9
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 7
- QZJVWTNHFOMVHX-UHFFFAOYSA-N methanol;methyl acetate Chemical compound OC.COC(C)=O QZJVWTNHFOMVHX-UHFFFAOYSA-N 0.000 description 5
- 239000004372 Polyvinyl alcohol Substances 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 229920002451 polyvinyl alcohol Polymers 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 238000005810 carbonylation reaction Methods 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 3
- TYLYVJBCMQFRCB-UHFFFAOYSA-K trichlororhodium;trihydrate Chemical compound O.O.O.[Cl-].[Cl-].[Cl-].[Rh+3] TYLYVJBCMQFRCB-UHFFFAOYSA-K 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LEKJTGQWLAUGQA-UHFFFAOYSA-N acetyl iodide Chemical compound CC(I)=O LEKJTGQWLAUGQA-UHFFFAOYSA-N 0.000 description 2
- HSZCZNFXUDYRKD-UHFFFAOYSA-M lithium iodide Chemical compound [Li+].[I-] HSZCZNFXUDYRKD-UHFFFAOYSA-M 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 238000006140 methanolysis reaction Methods 0.000 description 2
- 229920002689 polyvinyl acetate Polymers 0.000 description 2
- 239000011118 polyvinyl acetate Substances 0.000 description 2
- 150000003284 rhodium compounds Chemical class 0.000 description 2
- YWWDBCBWQNCYNR-UHFFFAOYSA-N trimethylphosphine Chemical compound CP(C)C YWWDBCBWQNCYNR-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- MBVAQOHBPXKYMF-LNTINUHCSA-N (z)-4-hydroxypent-3-en-2-one;rhodium Chemical compound [Rh].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O MBVAQOHBPXKYMF-LNTINUHCSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- LVGLLYVYRZMJIN-UHFFFAOYSA-N carbon monoxide;rhodium Chemical group [Rh].[Rh].[Rh].[Rh].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-] LVGLLYVYRZMJIN-UHFFFAOYSA-N 0.000 description 1
- 230000006315 carbonylation Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001845 chromium compounds Chemical class 0.000 description 1
- WYYQVWLEPYFFLP-UHFFFAOYSA-K chromium(3+);triacetate Chemical compound [Cr+3].CC([O-])=O.CC([O-])=O.CC([O-])=O WYYQVWLEPYFFLP-UHFFFAOYSA-K 0.000 description 1
- PPUZYFWVBLIDMP-UHFFFAOYSA-K chromium(3+);triiodide Chemical compound I[Cr](I)I PPUZYFWVBLIDMP-UHFFFAOYSA-K 0.000 description 1
- ORICWOYODJGJMY-UHFFFAOYSA-N dibutyl(phenyl)phosphane Chemical compound CCCCP(CCCC)C1=CC=CC=C1 ORICWOYODJGJMY-UHFFFAOYSA-N 0.000 description 1
- AAXGWYDSLJUQLN-UHFFFAOYSA-N diphenyl(propyl)phosphane Chemical compound C=1C=CC=CC=1P(CCC)C1=CC=CC=C1 AAXGWYDSLJUQLN-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000895 extractive distillation Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- SJLOMQIUPFZJAN-UHFFFAOYSA-N oxorhodium Chemical compound [Rh]=O SJLOMQIUPFZJAN-UHFFFAOYSA-N 0.000 description 1
- 150000004714 phosphonium salts Chemical group 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229910003450 rhodium oxide Inorganic materials 0.000 description 1
- SVOOVMQUISJERI-UHFFFAOYSA-K rhodium(3+);triacetate Chemical compound [Rh+3].CC([O-])=O.CC([O-])=O.CC([O-])=O SVOOVMQUISJERI-UHFFFAOYSA-K 0.000 description 1
- SONJTKJMTWTJCT-UHFFFAOYSA-K rhodium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Rh+3] SONJTKJMTWTJCT-UHFFFAOYSA-K 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1
- 150000004684 trihydrates Chemical class 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57163034A JPS5953440A (ja) | 1982-09-17 | 1982-09-17 | 無水酢酸と酢酸の同時的製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57163034A JPS5953440A (ja) | 1982-09-17 | 1982-09-17 | 無水酢酸と酢酸の同時的製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5953440A JPS5953440A (ja) | 1984-03-28 |
| JPH0352452B2 true JPH0352452B2 (uk) | 1991-08-12 |
Family
ID=15765923
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57163034A Granted JPS5953440A (ja) | 1982-09-17 | 1982-09-17 | 無水酢酸と酢酸の同時的製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5953440A (uk) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US7115772B2 (en) * | 2002-01-11 | 2006-10-03 | Celanese International Corporation | Integrated process for producing carbonylation acetic acid, acetic anhydride, or coproduction of each from a methyl acetate by-product stream |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5111705A (ja) * | 1974-07-17 | 1976-01-30 | Showa Denko Kk | Sakusangoseiyohannosochi |
| JPS5699437A (en) * | 1979-12-26 | 1981-08-10 | Halcon International Inc | Manufacture of acetic anhydride |
| JPS56142234A (en) * | 1980-04-09 | 1981-11-06 | Daicel Chem Ind Ltd | Production of acetic anhydride |
| JPS5877840A (ja) * | 1981-11-04 | 1983-05-11 | Mitsubishi Gas Chem Co Inc | 無水酢酸の製造方法 |
| JPS58164539A (ja) * | 1982-02-13 | 1983-09-29 | ビ−ピ−・ケミカルズ・リミテツド | カルボン酸および酸無水物の同時製造方法 |
-
1982
- 1982-09-17 JP JP57163034A patent/JPS5953440A/ja active Granted
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5111705A (ja) * | 1974-07-17 | 1976-01-30 | Showa Denko Kk | Sakusangoseiyohannosochi |
| JPS5699437A (en) * | 1979-12-26 | 1981-08-10 | Halcon International Inc | Manufacture of acetic anhydride |
| JPS56142234A (en) * | 1980-04-09 | 1981-11-06 | Daicel Chem Ind Ltd | Production of acetic anhydride |
| JPS5877840A (ja) * | 1981-11-04 | 1983-05-11 | Mitsubishi Gas Chem Co Inc | 無水酢酸の製造方法 |
| JPS58164539A (ja) * | 1982-02-13 | 1983-09-29 | ビ−ピ−・ケミカルズ・リミテツド | カルボン酸および酸無水物の同時製造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5953440A (ja) | 1984-03-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3772380A (en) | Production of carboxylic acids and esters | |
| US3769329A (en) | Production of carboxylic acids and esters | |
| JP2842444B2 (ja) | 含窒素塩基の蟻酸塩の製造方法 | |
| US4306091A (en) | Process for the preparation of acetaldehyde | |
| US4356320A (en) | Preparation of carboxylic acids | |
| JPS6344135B2 (uk) | ||
| US4134912A (en) | Process for preparing carboxylic acids | |
| US4360406A (en) | Process for the preparation of tertiary butyl alcohol | |
| JPH10509695A (ja) | イリジウム存在下のカルボニル化によるカルボン酸類又はそのエステル類の製造 | |
| EP1099680A2 (en) | Process for the production of acetic acid | |
| EP0048046B1 (en) | Method for the manufacture of ethylidene diacetate | |
| JPH0352452B2 (uk) | ||
| EP0937025B1 (en) | Manufacture of adipic acid | |
| US4323697A (en) | Process for preparing ethylidene diacetate | |
| US4483804A (en) | Preparation of carboxylic acid anhydrides | |
| EP0077116B1 (en) | Preparation of alkylidene diesters | |
| US4408080A (en) | Process for producing acetaldehyde | |
| US5189214A (en) | Production of acetic acid | |
| JPH04230241A (ja) | α−ヒドロキシエステルの合成法 | |
| JPS58121226A (ja) | エチレン・グリコ−ル及び低級１価アルコ−ルの製造方法 | |
| JP3756537B2 (ja) | ジメチルデカンジアールおよびその製造方法 | |
| JPS59157053A (ja) | モノエステルの製造法 | |
| JP2016510058A (ja) | プロセス | |
| JPH05140024A (ja) | 酢酸の製造法 | |
| JPS609734B2 (ja) | エチレングリコ−ルの製造法 |