CA1081254A - Manufacture of alkylcarboxylic acids - Google Patents

Manufacture of alkylcarboxylic acids

Info

Publication number: CA1081254A
Authority: CA; Canada
Prior art keywords: rhodium; oxygen; hydroformylation; cnh2n; oxidation
Prior art date: 1976-02-06
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

Application number

CA270,377A

Other languages

English (en)

French (fr)

Inventor

Wolfgang Eisfeld

Rudolf Kummer

Walter Disteldorf

Kurt Schwirten

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

BASF SE

Original Assignee

BASF SE

Priority date (The priority date 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 date listed.)

1976-02-06

Filing date

1977-01-21

Publication date

1980-07-08

1977-01-21 Application filed by BASF SE filed Critical BASF SE

1980-07-08 Application granted granted Critical

1980-07-08 Publication of CA1081254A publication Critical patent/CA1081254A/en

Status Expired legal-status Critical Current

Links

239000002253 acid Substances 0.000 title claims abstract description 5
238000004519 manufacturing process Methods 0.000 title claims description 5
150000007513 acids Chemical class 0.000 title abstract description 4
238000007037 hydroformylation reaction Methods 0.000 claims abstract description 16
239000010948 rhodium Substances 0.000 claims abstract description 14
229910052703 rhodium Inorganic materials 0.000 claims abstract description 13
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims abstract description 13
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 12
238000000034 method Methods 0.000 claims abstract description 12
239000001301 oxygen Substances 0.000 claims abstract description 12
229910052760 oxygen Inorganic materials 0.000 claims abstract description 12
150000001336 alkenes Chemical class 0.000 claims abstract description 10
239000000203 mixture Substances 0.000 claims abstract description 9
230000003647 oxidation Effects 0.000 claims abstract description 9
238000007254 oxidation reaction Methods 0.000 claims abstract description 9
238000004821 distillation Methods 0.000 claims abstract description 7
239000003054 catalyst Substances 0.000 claims abstract description 6
229910002091 carbon monoxide Inorganic materials 0.000 claims abstract description 5
239000007789 gas Substances 0.000 claims abstract description 5
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims abstract description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 4
239000001257 hydrogen Substances 0.000 claims abstract description 4
230000001590 oxidative effect Effects 0.000 claims abstract description 4
239000011541 reaction mixture Substances 0.000 claims abstract description 3
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 2
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
150000001299 aldehydes Chemical class 0.000 abstract description 6
150000001735 carboxylic acids Chemical class 0.000 abstract description 4
238000006243 chemical reaction Methods 0.000 description 6
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 6
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 2
FXNDIJDIPNCZQJ-UHFFFAOYSA-N 2,4,4-trimethylpent-1-ene Chemical group CC(=C)CC(C)(C)C FXNDIJDIPNCZQJ-UHFFFAOYSA-N 0.000 description 2
VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
235000014113 dietary fatty acids Nutrition 0.000 description 2
229930195729 fatty acid Natural products 0.000 description 2
239000000194 fatty acid Substances 0.000 description 2
150000003284 rhodium compounds Chemical class 0.000 description 2
XYHKNCXZYYTLRG-UHFFFAOYSA-N 1h-imidazole-2-carbaldehyde Chemical compound O=CC1=NC=CN1 XYHKNCXZYYTLRG-UHFFFAOYSA-N 0.000 description 1
GWYFCOCPABKNJV-UHFFFAOYSA-M 3-Methylbutanoic acid Natural products CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 description 1
101100087530 Caenorhabditis elegans rom-1 gene Proteins 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
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 description 1
101100305983 Mus musculus Rom1 gene Proteins 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
230000002730 additional effect Effects 0.000 description 1
GWYFCOCPABKNJV-UHFFFAOYSA-N beta-methyl-butyric acid Natural products CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
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 description 1
230000006315 carbonylation Effects 0.000 description 1
238000005810 carbonylation reaction Methods 0.000 description 1
239000003795 chemical substances by application Substances 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
239000000470 constituent Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
239000000539 dimer Substances 0.000 description 1
-1 fatty acid salts Chemical class 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
239000000463 material Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
150000002842 nonanoic acids Chemical class 0.000 description 1
FIYHBCPZNHSHKU-UHFFFAOYSA-K octadecanoate rhodium(3+) Chemical compound [Rh+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O FIYHBCPZNHSHKU-UHFFFAOYSA-K 0.000 description 1
229960003903 oxygen Drugs 0.000 description 1
239000001294 propane Substances 0.000 description 1
230000036647 reaction Effects 0.000 description 1
150000003283 rhodium Chemical class 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
239000013638 trimer Substances 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
238000010626 work up procedure Methods 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)

CA270,377A 1976-02-06 1977-01-21 Manufacture of alkylcarboxylic acids Expired CA1081254A (en)

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
CA1081254A true CA1081254A (en)	1980-07-08

Family

ID=5969157

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA270,377A Expired CA1081254A (en)	1976-02-06	1977-01-21	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 (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
TWI487692B (zh) *	2012-07-13	2015-06-11	奧克昔亞公司	由２－乙基己醇製造異壬酸之製法和製品及其衍生物之製法
US9334225B2 (en)	2012-07-13	2016-05-10	Oxea Gmbh	Vinyl esters of isononanoic acid starting from 2-ethyl hexanol, methods for the production thereof and use thereof
US9434675B2 (en)	2012-07-13	2016-09-06	Oxga Gmbh	Method for producing isononanoic acid esters, starting from 2-ethyl hexanol

Families Citing this family (16)

* Cited by examiner, † Cited by third party
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
DE4427428A1 (de)	1994-08-03	1996-02-29	Basf Ag	Verfahren zur Herstellung von 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
US5728658A (en) *	1996-05-21	1998-03-17	Exxon Chemical Patents Inc	Biodegradable synthetic ester base stocks formed from branched oxo acids
CZ283697A3 (cs) *	1996-09-11	1998-04-15	Mitsubishi Chemical Corporation	Způsob přípravy roztoku komplexu rhodia a jeho použití
DE19801437A1 (de)	1998-01-16	1999-07-22	Basf Ag	Verfahren zur Herstellung von Aldehyden
DE10010771C1 (de)	2000-03-04	2001-05-03	Celanese Chem Europe Gmbh	Verfahren zur Herstellung aliphatischer Carbonsäuren aus Aldehyden
DE102007053385A1 (de) *	2007-11-09	2009-05-20	Oxea Deutschland Gmbh	Verfahren zur Herstellung von Aldehyden
DE102013020323B3 (de)	2013-12-05	2015-01-08	Oxea Gmbh	Verfahren zur Herstellung von isomeren Hexansäuren aus den bei der Herstellung von Pentanalen anfallenden Nebenströmen
DE102013020320B4 (de)	2013-12-05	2019-04-04	Oxea Gmbh	Verfahren zur Herstellung von 2-Methylbuttersäure mit einem vermindertem Gehalt an 3-Methylbuttersäure aus den bei der Herstellung von Pentansäuren anfallenden Nebenströmen
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

Family Cites Families (4)

* Cited by examiner, † Cited by third party
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 (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
TWI487692B (zh) *	2012-07-13	2015-06-11	奧克昔亞公司	由２－乙基己醇製造異壬酸之製法和製品及其衍生物之製法
US9334225B2 (en)	2012-07-13	2016-05-10	Oxea Gmbh	Vinyl esters of isononanoic acid starting from 2-ethyl hexanol, methods for the production thereof and use thereof
US9434672B2 (en)	2012-07-13	2016-09-06	Oxea Gmbh	Method for producing isononanoic acids from 2-ethyl hexanol
US9434675B2 (en)	2012-07-13	2016-09-06	Oxga Gmbh	Method for producing isononanoic acid esters, starting from 2-ethyl hexanol

Also Published As

Publication number	Publication date
DE2604545B2 (de)	1977-12-22
ES455653A1 (es)	1978-01-01
FR2340300B1 (de)	1983-08-19
ATA74277A (de)	1978-07-15
JPS5295604A (en)	1977-08-11
AT348500B (de)	1979-02-26
DE2604545C3 (de)	1978-08-17
FR2340300A1 (fr)	1977-09-02
GB1565716A (en)	1980-04-23
DE2604545A1 (de)	1977-08-18

Legal Events

Date	Code	Title	Description
1997-07-08	MKEX	Expiry

Publication	Publication Date	Title
US3772380A (en)	1973-11-13	Production of carboxylic acids and esters
US4528403A (en)	1985-07-09	Hydroformylation process for preparation of aldehydes and alcohols
US3769329A (en)	1973-10-30	Production of carboxylic acids and esters
US4277627A (en)	1981-07-07	Hydroformylation process
US6573409B1 (en)	2003-06-03	Process for the preparation of 3,3-dimethylbutanal
GB1565716A (en)	1980-04-23	Manufacture of alkylcarboxylic acids
US4072709A (en)	1978-02-07	Production of lactic acid
Pruett et al.	1982	Reactions of formic acid. 1. The iridium-catalyzed synthesis of acetic acid from methyl formate
CA1113491A (en)	1981-12-01	Manufacture of butanedicarboxylic acid esters
US5281751A (en)	1994-01-25	Synergistic production of carboxylic acids from alcohols
US3813428A (en)	1974-05-28	Production of monocarboxylic acids
US4220800A (en)	1980-09-02	Oxidative esterification process
US4256909A (en)	1981-03-17	Preparation of dimethyl butanedicarboxylates
US4619790A (en)	1986-10-28	Manufacture of higher alkylcarboxylic acids
US3944604A (en)	1976-03-16	Production of propionic acid
US4235744A (en)	1980-11-25	Carbonylation of olefinically unsaturated compounds
JPH0338256B2 (de)	1991-06-10
CA1155458A (en)	1983-10-18	Process for the selective hydroformylation of methanol to acetaldehyde
US4614816A (en)	1986-09-30	Preparation of carboxylic acids and esters thereof
CA1106857A (en)	1981-08-11	Process for the preparation of 3-(4-methyl-3- cyclohexen-1-yl) butyraldehyde
US4259520A (en)	1981-03-31	Preparation of butanedicarboxylic acid esters
Pennequin et al.	1996	Palladium catalyzed oxidative carbonylation of alkenes by methyl formate
US4386217A (en)	1983-05-31	Oxidative alkoxycarbonylation of olefins with palladium/heteropoly acid catalyst systems
US4354037A (en)	1982-10-12	Process for preparing benzenecarboxylic acids
US4794199A (en)	1988-12-27	Process for synthesis of primary amines from olefins, syngas and ammonia