GB1565716A - Manufacture of alkylcarboxylic acids - Google Patents
Manufacture of alkylcarboxylic acids Download PDFInfo
- Publication number
- GB1565716A GB1565716A GB4610/77A GB461077A GB1565716A GB 1565716 A GB1565716 A GB 1565716A GB 4610/77 A GB4610/77 A GB 4610/77A GB 461077 A GB461077 A GB 461077A GB 1565716 A GB1565716 A GB 1565716A
- Authority
- GB
- United Kingdom
- Prior art keywords
- rhodium
- hydroformylation
- oxygen
- mixture
- oxidation
- 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
Links
- 239000002253 acid Substances 0.000 title claims description 10
- 238000004519 manufacturing process Methods 0.000 title claims description 9
- 150000007513 acids Chemical class 0.000 title claims description 6
- 238000007037 hydroformylation reaction Methods 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 27
- 239000010948 rhodium Substances 0.000 claims description 23
- 150000001336 alkenes Chemical class 0.000 claims description 22
- 229910052703 rhodium Inorganic materials 0.000 claims description 21
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 21
- 230000003647 oxidation Effects 0.000 claims description 18
- 238000007254 oxidation reaction Methods 0.000 claims description 18
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 17
- 239000001301 oxygen Substances 0.000 claims description 17
- 229910052760 oxygen Inorganic materials 0.000 claims description 17
- 238000004821 distillation Methods 0.000 claims description 15
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 13
- 150000001299 aldehydes Chemical class 0.000 claims description 8
- 150000001735 carboxylic acids Chemical class 0.000 claims description 8
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 8
- 239000000194 fatty acid Substances 0.000 claims description 8
- 229930195729 fatty acid Natural products 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 7
- 239000003054 catalyst Substances 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 230000001590 oxidative effect Effects 0.000 claims description 7
- 239000011541 reaction mixture Substances 0.000 claims description 7
- 239000007789 gas Substances 0.000 claims description 6
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 5
- 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 claims description 4
- FXNDIJDIPNCZQJ-UHFFFAOYSA-N 2,4,4-trimethylpent-1-ene Chemical group CC(=C)CC(C)(C)C FXNDIJDIPNCZQJ-UHFFFAOYSA-N 0.000 claims description 4
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 4
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 4
- 150000001298 alcohols Chemical class 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- -1 fatty acid salts Chemical class 0.000 claims description 4
- 150000004665 fatty acids Chemical class 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 150000003283 rhodium Chemical class 0.000 claims description 4
- 125000000383 tetramethylene group Chemical class [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 3
- 239000013638 trimer Substances 0.000 claims description 3
- XYHKNCXZYYTLRG-UHFFFAOYSA-N 1h-imidazole-2-carbaldehyde Chemical compound O=CC1=NC=CN1 XYHKNCXZYYTLRG-UHFFFAOYSA-N 0.000 claims description 2
- NNOAPAKAIIYKJW-UHFFFAOYSA-N 2-methylprop-1-ene 2,4,4-trimethylpent-1-ene Chemical compound CC(C)=C.CC(C)=C.CC(=C)CC(C)(C)C NNOAPAKAIIYKJW-UHFFFAOYSA-N 0.000 claims description 2
- GWYFCOCPABKNJV-UHFFFAOYSA-M 3-Methylbutanoic acid Natural products CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 claims description 2
- 238000010521 absorption reaction Methods 0.000 claims description 2
- GWYFCOCPABKNJV-UHFFFAOYSA-N beta-methyl-butyric acid Natural products CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- GGRQQHADVSXBQN-FGSKAQBVSA-N carbon monoxide;(z)-4-hydroxypent-3-en-2-one;rhodium Chemical compound [Rh].[O+]#[C-].[O+]#[C-].C\C(O)=C\C(C)=O GGRQQHADVSXBQN-FGSKAQBVSA-N 0.000 claims description 2
- 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 claims description 2
- 239000000470 constituent Substances 0.000 claims description 2
- 238000007796 conventional method Methods 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 150000002842 nonanoic acids Chemical class 0.000 claims description 2
- FIYHBCPZNHSHKU-UHFFFAOYSA-K octadecanoate rhodium(3+) Chemical compound [Rh+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O FIYHBCPZNHSHKU-UHFFFAOYSA-K 0.000 claims description 2
- 239000007800 oxidant agent Substances 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 238000010626 work up procedure Methods 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000005810 carbonylation reaction Methods 0.000 description 2
- 150000003284 rhodium compounds Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000006315 carbonylation Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- AMFIJXSMYBKJQV-UHFFFAOYSA-L cobalt(2+);octadecanoate Chemical compound [Co+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O AMFIJXSMYBKJQV-UHFFFAOYSA-L 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09F—NATURAL RESINS; FRENCH POLISH; DRYING-OILS; OIL DRYING AGENTS, i.e. SICCATIVES; TURPENTINE
- C09F9/00—Compounds to be used as driers, i.e. siccatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
- C07C45/50—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide by oxo-reactions
-
- 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
- C07C51/14—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction with carbon monoxide on a carbon-to-carbon unsaturated bond in organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
- C07C51/23—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of oxygen-containing groups to carboxyl groups
- C07C51/235—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of oxygen-containing groups to carboxyl groups of —CHO groups or primary alcohol groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2604545A DE2604545C3 (de) | 1976-02-06 | 1976-02-06 | Verfahren zur Herstellung von Alkylcarbonsäuren |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1565716A true GB1565716A (en) | 1980-04-23 |
Family
ID=5969157
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4610/77A Expired GB1565716A (en) | 1976-02-06 | 1977-02-04 | Manufacture of alkylcarboxylic acids |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS5295604A (de) |
| AT (1) | AT348500B (de) |
| CA (1) | CA1081254A (de) |
| DE (1) | DE2604545C3 (de) |
| ES (1) | ES455653A1 (de) |
| FR (1) | FR2340300A1 (de) |
| GB (1) | GB1565716A (de) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997044416A1 (en) * | 1996-05-21 | 1997-11-27 | Exxon Chemical Patents Inc. | Biodegradable synthetic ester base stocks formed from branched oxo acids |
| US5696297A (en) * | 1994-08-03 | 1997-12-09 | Basf Aktiengesellschaft | Preparation of aldehydes |
| US5936130A (en) * | 1996-09-11 | 1999-08-10 | Mitsubishi Chemical Corporation | Process for preparing a rhodium complex solution and process for producing an aldehyde |
| WO2001066504A2 (de) * | 2000-03-04 | 2001-09-13 | Celanese Chemicals Europe Gmbh | Verfahren zur herstellung aliphatischer carbonsäuren aus aldehyden |
| CN104411675A (zh) * | 2012-07-13 | 2015-03-11 | Oxea有限责任公司 | 由2-乙烯己醇起始制备的异壬酸乙烯酯、其生产方法及其用途 |
| US9517995B2 (en) | 2013-12-05 | 2016-12-13 | Oxea Gmbh | Method for producing isomeric hexanoic acids from the subsidiary flows arising during the production of pentanals |
| US9896406B2 (en) | 2013-12-05 | 2018-02-20 | Oxea Gmbh | Method for producing 2-methylbutyric acid having a reduced content of 3-methylbutyric acid from the secondary flows arising in the production of pentanoic acids |
| CN111470962A (zh) * | 2020-04-28 | 2020-07-31 | 浙江师范大学 | 一种由混合异构辛烯制备异壬酸的方法 |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4273936A (en) * | 1979-09-28 | 1981-06-16 | Union Carbide Corporation | Rhodium-catalyzed oxidation process for producing carboxylic acids |
| US4343950A (en) * | 1980-06-16 | 1982-08-10 | Union Carbide Corporation | Rhodium-catalyzed oxidation process for producing carboxylic acids |
| DE4316180A1 (de) * | 1992-09-16 | 1994-11-17 | Basf Ag | Verfahren zur Herstellung von Aldehyden |
| DE4408950A1 (de) * | 1994-03-16 | 1995-09-21 | Basf Ag | Verfahren zur Herstellung von Alkoholen und/oder Aldehyden |
| DE4440801A1 (de) * | 1994-11-17 | 1996-05-23 | Basf Ag | Verfahren zur Herstellung von Aldehyden |
| DE19603201A1 (de) * | 1996-01-30 | 1997-07-31 | Basf Ag | Verfahren zur Herstellung von Aldehyden durch Hydroformylierung von Olefinen |
| DE19605435A1 (de) | 1996-02-14 | 1997-08-21 | Basf Ag | Verfahren zur Herstellung von Aldehyden durch Hydroformylierung mit einem Rhodiumkatalysator und Wiedergewinnung des Rhodiumkatalysators durch Extraktion |
| DE19801437A1 (de) | 1998-01-16 | 1999-07-22 | Basf Ag | Verfahren zur Herstellung von Aldehyden |
| DE102007053385A1 (de) * | 2007-11-09 | 2009-05-20 | Oxea Deutschland Gmbh | Verfahren zur Herstellung von Aldehyden |
| DE102012013968A1 (de) | 2012-07-13 | 2014-04-03 | Oxea Gmbh | Carbonsäureester der Isononansäure ausgehend von 2-Ethylhexanol, Verfahren zu ihrer Herstellung sowie ihre Verwendung |
| DE102012013969B4 (de) * | 2012-07-13 | 2017-09-14 | Oxea Gmbh | Verfahren zur Herstellung eines Gemisches stellungsisomerer aliphatischer Isononansäuren ausgehend von 2-Ethylhexanol |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE887644C (de) * | 1943-07-21 | 1953-08-24 | Chemische Verwertungsgesellsch | Verfahren zur Herstellung von Carbonsaeuren |
| FR1018307A (fr) * | 1949-02-19 | 1953-01-06 | Anglo Iranian Oil Co Ltd | Procédé de production et de transformation de composés organiques oxygénés |
| US2779808A (en) * | 1954-03-31 | 1957-01-29 | Gulf Research Development Co | Oxidation of aldehydes |
| US3555098A (en) * | 1967-12-13 | 1971-01-12 | Union Oil Co | Hydroformylation |
-
1976
- 1976-02-06 DE DE2604545A patent/DE2604545C3/de not_active Expired
-
1977
- 1977-01-21 CA CA270,377A patent/CA1081254A/en not_active Expired
- 1977-02-03 FR FR7702986A patent/FR2340300A1/fr active Granted
- 1977-02-04 AT AT74277A patent/AT348500B/de not_active IP Right Cessation
- 1977-02-04 GB GB4610/77A patent/GB1565716A/en not_active Expired
- 1977-02-04 ES ES455653A patent/ES455653A1/es not_active Expired
- 1977-02-07 JP JP1171277A patent/JPS5295604A/ja active Pending
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5696297A (en) * | 1994-08-03 | 1997-12-09 | Basf Aktiengesellschaft | Preparation of aldehydes |
| WO1997044416A1 (en) * | 1996-05-21 | 1997-11-27 | Exxon Chemical Patents Inc. | Biodegradable synthetic ester base stocks formed from branched oxo acids |
| US5936130A (en) * | 1996-09-11 | 1999-08-10 | Mitsubishi Chemical Corporation | Process for preparing a rhodium complex solution and process for producing an aldehyde |
| WO2001066504A2 (de) * | 2000-03-04 | 2001-09-13 | Celanese Chemicals Europe Gmbh | Verfahren zur herstellung aliphatischer carbonsäuren aus aldehyden |
| WO2001066504A3 (de) * | 2000-03-04 | 2002-02-21 | Celanese Chem Europe Gmbh | Verfahren zur herstellung aliphatischer carbonsäuren aus aldehyden |
| US6800783B2 (en) | 2000-03-04 | 2004-10-05 | Celanese Chemicals Europe Gmbh | Method for the synthesis of aliphatic carboxylic acids from aldehydes |
| CN104411675A (zh) * | 2012-07-13 | 2015-03-11 | Oxea有限责任公司 | 由2-乙烯己醇起始制备的异壬酸乙烯酯、其生产方法及其用途 |
| CN104411675B (zh) * | 2012-07-13 | 2016-10-12 | Oxea有限责任公司 | 由2-乙烯己醇起始制备的异壬酸乙烯酯、其生产方法及其用途 |
| US9517995B2 (en) | 2013-12-05 | 2016-12-13 | Oxea Gmbh | Method for producing isomeric hexanoic acids from the subsidiary flows arising during the production of pentanals |
| US9896406B2 (en) | 2013-12-05 | 2018-02-20 | Oxea Gmbh | Method for producing 2-methylbutyric acid having a reduced content of 3-methylbutyric acid from the secondary flows arising in the production of pentanoic acids |
| CN111470962A (zh) * | 2020-04-28 | 2020-07-31 | 浙江师范大学 | 一种由混合异构辛烯制备异壬酸的方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2340300B1 (de) | 1983-08-19 |
| DE2604545C3 (de) | 1978-08-17 |
| DE2604545B2 (de) | 1977-12-22 |
| FR2340300A1 (fr) | 1977-09-02 |
| ES455653A1 (es) | 1978-01-01 |
| DE2604545A1 (de) | 1977-08-18 |
| CA1081254A (en) | 1980-07-08 |
| AT348500B (de) | 1979-02-26 |
| JPS5295604A (en) | 1977-08-11 |
| ATA74277A (de) | 1978-07-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |