CA1088563A - Production d'acides carboxyliques a partir d'olefines et de melanges d'olefines - Google Patents

Production d'acides carboxyliques a partir d'olefines et de melanges d'olefines

Info

Publication number: CA1088563A
Authority: CA; Canada
Prior art keywords: olefins; acid; olefin; mixtures; carbon atoms
Prior art date: 1977-03-24
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

CA291,269A

Other languages

English (en)

Inventor

Anatoli Onopchenko

Johann G. D. Schulz

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.)

Gulf Research and Development Co

Original Assignee

Gulf Research and Development Co

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.)

1977-03-24

Filing date

1977-11-18

Publication date

1980-10-28

1977-11-18 Application filed by Gulf Research and Development Co filed Critical Gulf Research and Development Co

1980-10-28 Application granted granted Critical

1980-10-28 Publication of CA1088563A publication Critical patent/CA1088563A/fr

Status Expired legal-status Critical Current

Links

150000001336 alkenes Chemical class 0.000 title claims abstract description 32
150000001735 carboxylic acids Chemical class 0.000 title claims abstract description 15
239000000203 mixture Substances 0.000 title claims abstract description 14
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 22
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract description 17
238000000034 method Methods 0.000 claims abstract description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 12
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims abstract description 10
229910002091 carbon monoxide Inorganic materials 0.000 claims abstract description 9
239000007795 chemical reaction product Substances 0.000 claims abstract description 4
239000002904 solvent Substances 0.000 claims abstract description 4
125000004432 carbon atom Chemical group C* 0.000 claims abstract 7
239000000047 product Substances 0.000 claims description 12
238000006243 chemical reaction Methods 0.000 claims description 8
-1 C24 olefins Chemical class 0.000 claims description 4
239000004711 α-olefin Substances 0.000 claims description 3
GQEZCXVZFLOKMC-UHFFFAOYSA-N 1-hexadecene Chemical compound CCCCCCCCCCCCCCC=C GQEZCXVZFLOKMC-UHFFFAOYSA-N 0.000 claims 2
VAMFXQBUQXONLZ-UHFFFAOYSA-N n-alpha-eicosene Natural products CCCCCCCCCCCCCCCCCCC=C VAMFXQBUQXONLZ-UHFFFAOYSA-N 0.000 claims 2
CCCMONHAUSKTEQ-UHFFFAOYSA-N octadec-1-ene Chemical compound CCCCCCCCCCCCCCCCC=C CCCMONHAUSKTEQ-UHFFFAOYSA-N 0.000 claims 2
229940106006 1-eicosene Drugs 0.000 claims 1
FIKTURVKRGQNQD-UHFFFAOYSA-N 1-eicosene Natural products CCCCCCCCCCCCCCCCCC=CC(O)=O FIKTURVKRGQNQD-UHFFFAOYSA-N 0.000 claims 1
150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 claims 1
239000002253 acid Substances 0.000 description 30
229910052799 carbon Inorganic materials 0.000 description 17
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 14
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
150000001721 carbon Chemical group 0.000 description 7
238000010626 work up procedure Methods 0.000 description 5
150000007513 acids Chemical class 0.000 description 4
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
240000002989 Euphorbia neriifolia Species 0.000 description 3
238000009835 boiling Methods 0.000 description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
230000007935 neutral effect Effects 0.000 description 3
244000007835 Cyamopsis tetragonoloba Species 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
DQSGVVGOPRWTKI-QVFAWCHISA-N atazanavir sulfate Chemical compound [H+].[H+].[O-]S([O-])(=O)=O.C([C@H](NC(=O)[C@@H](NC(=O)OC)C(C)(C)C)[C@@H](O)CN(CC=1C=CC(=CC=1)C=1N=CC=CC=1)NC(=O)[C@@H](NC(=O)OC)C(C)(C)C)C1=CC=CC=C1 DQSGVVGOPRWTKI-QVFAWCHISA-N 0.000 description 2
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
229910052753 mercury Inorganic materials 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
GGQQNYXPYWCUHG-RMTFUQJTSA-N (3e,6e)-deca-3,6-diene Chemical compound CCC\C=C\C\C=C\CC GGQQNYXPYWCUHG-RMTFUQJTSA-N 0.000 description 1
MSDLOTWEPIAJFG-FNORWQNLSA-N (E)-docos-3-ene Chemical compound CCCCCCCCCCCCCCCCCC\C=C\CC MSDLOTWEPIAJFG-FNORWQNLSA-N 0.000 description 1
SAHHVBUNBUSDIX-FYWRMAATSA-N (e)-docos-7-ene Chemical compound CCCCCCCCCCCCCC\C=C\CCCCCC SAHHVBUNBUSDIX-FYWRMAATSA-N 0.000 description 1
YITMLDIGEJSENC-HWKANZROSA-N (e)-hexadec-2-ene Chemical compound CCCCCCCCCCCCC\C=C\C YITMLDIGEJSENC-HWKANZROSA-N 0.000 description 1
IRYCVIRCWSSJOW-FYWRMAATSA-N (e)-tricos-7-ene Chemical compound CCCCCCCCCCCCCCC\C=C\CCCCCC IRYCVIRCWSSJOW-FYWRMAATSA-N 0.000 description 1
ICTHKNOBBDSFPZ-UHFFFAOYSA-N 8-methylidenepentadecane Chemical compound CCCCCCCC(=C)CCCCCCC ICTHKNOBBDSFPZ-UHFFFAOYSA-N 0.000 description 1
JSEZWBOLDGVZFR-BMRADRMJSA-N 8E-Heneicosene Chemical compound CCCCCCCCCCCC\C=C\CCCCCCC JSEZWBOLDGVZFR-BMRADRMJSA-N 0.000 description 1
ODKSFYDXXFIFQN-UHFFFAOYSA-N Arginine Chemical compound OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
241000518994 Conta Species 0.000 description 1
OPFTUNCRGUEPRZ-QLFBSQMISA-N Cyclohexane Natural products CC(=C)[C@@H]1CC[C@@](C)(C=C)[C@H](C(C)=C)C1 OPFTUNCRGUEPRZ-QLFBSQMISA-N 0.000 description 1
ZAKOWWREFLAJOT-CEFNRUSXSA-N D-alpha-tocopherylacetate Chemical compound CC(=O)OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C ZAKOWWREFLAJOT-CEFNRUSXSA-N 0.000 description 1
241000282326 Felis catus Species 0.000 description 1
YITMLDIGEJSENC-UHFFFAOYSA-N Hexadecen Natural products CCCCCCCCCCCCCC=CC YITMLDIGEJSENC-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
241000283984 Rodentia Species 0.000 description 1
229910000831 Steel Inorganic materials 0.000 description 1
LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 description 1
TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000005587 carbonate group Chemical group 0.000 description 1
230000021523 carboxylation Effects 0.000 description 1
238000006473 carboxylation reaction Methods 0.000 description 1
238000010908 decantation Methods 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
ZAFDRRSRCRBHPC-UHFFFAOYSA-N docos-4-ene Chemical compound CCCCCCCCCCCCCCCCCC=CCCC ZAFDRRSRCRBHPC-UHFFFAOYSA-N 0.000 description 1
YSOYEKWEVFGYOA-UHFFFAOYSA-N docos-8-ene Chemical compound CCCCCCCCCCCCCC=CCCCCCCC YSOYEKWEVFGYOA-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
QIZDLUWRENVVJW-UHFFFAOYSA-N hexadec-3-ene Chemical compound CCCCCCCCCCCCC=CCC QIZDLUWRENVVJW-UHFFFAOYSA-N 0.000 description 1
JZPUSPPFVAJNGY-UHFFFAOYSA-N hexadec-7-ene Chemical compound CCCCCCCCC=CCCCCCC JZPUSPPFVAJNGY-UHFFFAOYSA-N 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
ATADHKWKHYVBTJ-UHFFFAOYSA-N hydron;4-[1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol;chloride Chemical compound Cl.CNCC(O)C1=CC=C(O)C(O)=C1 ATADHKWKHYVBTJ-UHFFFAOYSA-N 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
239000010410 layer Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
JYHKRLOUMXMVLU-UHFFFAOYSA-N nonadec-6-ene Chemical compound CCCCCCCCCCCCC=CCCCCC JYHKRLOUMXMVLU-UHFFFAOYSA-N 0.000 description 1
COYUIDCASPAVQI-UHFFFAOYSA-N octadec-4-ene Chemical compound CCCCCCCCCCCCCC=CCCC COYUIDCASPAVQI-UHFFFAOYSA-N 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
238000003822 preparative gas chromatography Methods 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000000243 solution Substances 0.000 description 1
239000010959 steel Substances 0.000 description 1
OEPVTYSXFQUENG-UHFFFAOYSA-N tetracos-2-ene Chemical compound CCCCCCCCCCCCCCCCCCCCCC=CC OEPVTYSXFQUENG-UHFFFAOYSA-N 0.000 description 1
AINFQPFKWRNNSS-UHFFFAOYSA-N tetracos-4-ene Chemical compound CCCCCCCCCCCCCCCCCCCC=CCCC AINFQPFKWRNNSS-UHFFFAOYSA-N 0.000 description 1
238000004448 titration Methods 0.000 description 1
KOSQGEUUTJIEGI-UHFFFAOYSA-N tricos-3-ene Chemical compound CCCCCCCCCCCCCCCCCCCC=CCC KOSQGEUUTJIEGI-UHFFFAOYSA-N 0.000 description 1
GDBMGEJXCRMJGQ-UHFFFAOYSA-N tricos-8-ene Chemical compound CCCCCCCCCCCCCCC=CCCCCCCC GDBMGEJXCRMJGQ-UHFFFAOYSA-N 0.000 description 1
229940116269 uric acid Drugs 0.000 description 1
238000005406 washing Methods 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
- C07C51/14—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

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)
Detergent Compositions (AREA)

CA291,269A 1977-03-24 1977-11-18 Production d'acides carboxyliques a partir d'olefines et de melanges d'olefines Expired CA1088563A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US78092977A	1977-03-24	1977-03-24
US780,929		1977-03-24

Publications (1)

Publication Number	Publication Date
CA1088563A true CA1088563A (fr)	1980-10-28

Family

ID=25121126

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA291,269A Expired CA1088563A (fr)	1977-03-24	1977-11-18	Production d'acides carboxyliques a partir d'olefines et de melanges d'olefines

Country Status (4)

Country	Link
JP (1)	JPS53119815A (fr)
CA (1)	CA1088563A (fr)
DE (1)	DE2811886A1 (fr)
FR (1)	FR2384736A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA1339034C (fr) *	1988-08-22	1997-04-01	Paul A. Tremblay	Complexes de platine d'isomeres uniques d'acides neoalkyliques

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR1076357A (fr) *	1952-03-24	1954-10-26	Studien Und Verwertungs Ges M	Procédé d'obtention d'acides carboxyliques
US3842106A (en) *	1973-06-05	1974-10-15	Gulf Research Development Co	Composition containing higher fatty acids
DE2406223A1 (de) *	1974-02-09	1975-08-21	Basf Ag	Verfahren zur herstellung von carbonsaeuren

1977
- 1977-11-18 CA CA291,269A patent/CA1088563A/fr not_active Expired
- 1977-12-20 FR FR7738464A patent/FR2384736A1/fr not_active Withdrawn
1978
- 1978-03-18 DE DE19782811886 patent/DE2811886A1/de not_active Withdrawn
- 1978-03-23 JP JP3245378A patent/JPS53119815A/ja active Pending

Also Published As

Publication number	Publication date
DE2811886A1 (de)	1978-09-28
JPS53119815A (en)	1978-10-19
FR2384736A1 (fr)	1978-10-20

Legal Events

Date	Code	Title	Description
1997-10-28	MKEX	Expiry

Publication	Publication Date	Title
US2831877A (en)	1958-04-22	Production of carboxylic acids from olefins
US2564130A (en)	1951-08-14	One-step butyl alcohol process
US3053869A (en)	1962-09-11	Carboxylic acids
CA1088563A (fr)	1980-10-28	Production d'acides carboxyliques a partir d'olefines et de melanges d'olefines
US3470251A (en)	1969-09-30	Separation and purification of secondary alkyl primary amines
DE2745879A1 (de)	1978-04-13	Verfahren zur herstellung von 2,4,6-tri(3,5-ditert.butyl-4-oxybenzyl) mesitylen
EP0021373B1 (fr)	1982-07-07	Procédé de préparation de dichlorures d'acides dicarboxyliques aromatiques et leur utilisation dans la préparation de polycondensats
US3055934A (en)	1962-09-25	Preparation of esters from tertiary olefins
US3865855A (en)	1975-02-11	Process for catalytically converting fatty acids
US2362307A (en)	1944-11-07	Cyclic diethers
US2850538A (en)	1958-09-02	Preparation of synthetic glycols from conjugated aliphatic diolefins
US2450627A (en)	1948-10-05	Manufacture of tetrabasic acids
DE3873557T2 (de)	1992-12-10	Dimerisierungsverfahren fuer olefine.
EP0024492B1 (fr)	1982-05-05	Procédé de préparation de dichlorures d'acides dicarboxyliques aromatiques et leur utilisation dans la préparation de polycondensats
EP0022484B1 (fr)	1982-06-30	Procédé de préparation de dichlorures d'acides dicarboxyliques aromatiques et leur utilisation dans la préparation de polycondensats
DE2504230A1 (de)	1975-08-07	Verfahren zur herstellung von allylestern aus carbonsaeuren und allylalkoholen
US3262954A (en)	1966-07-26	Acid hydrolysis process
US2365703A (en)	1944-12-26	Alkylated cyclobutane carboxylic acid products and process for producing them
US2335691A (en)	1943-11-30	Method of preparing diolefins
US2635114A (en)	1953-04-14	Polyalkylbenzene carboxylic acid and process of preparing it
US2662086A (en)	1953-12-08	Method of preparing hydrolytic condensation product of dichlorodipropyl sulfide in aqueous hydrogen chloride and condensation product resulting therefrom
US3282993A (en)	1966-11-01	Carbonylation process
US2534074A (en)	1950-12-12	Reaction of alkyl cycloparaffins with unsaturated fatty acid
CS205045B2 (en)	1981-04-30	Process for selective production of isobutylene from mixture of hydrocarbons
US2632777A (en)	1953-03-24	Production of hydrocarbon conjunct polymers