NL8303419A - Werkwijze ter bereiding van beta-digesubstitueerde monocarbonzuren afkomstig van acyclische of cyclische koolwaterstoffen. - Google Patents
Werkwijze ter bereiding van beta-digesubstitueerde monocarbonzuren afkomstig van acyclische of cyclische koolwaterstoffen. Download PDFInfo
- Publication number
- NL8303419A NL8303419A NL8303419A NL8303419A NL8303419A NL 8303419 A NL8303419 A NL 8303419A NL 8303419 A NL8303419 A NL 8303419A NL 8303419 A NL8303419 A NL 8303419A NL 8303419 A NL8303419 A NL 8303419A
- Authority
- NL
- Netherlands
- Prior art keywords
- process according
- group
- carbon atoms
- general formula
- hydrocarbon
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims description 22
- 229930195733 hydrocarbon Natural products 0.000 title claims description 21
- 150000002430 hydrocarbons Chemical class 0.000 title claims description 17
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 150000007513 acids Chemical class 0.000 title description 5
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 18
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 150000001336 alkenes Chemical class 0.000 claims description 11
- 239000004215 Carbon black (E152) Substances 0.000 claims description 10
- 125000002950 monocyclic group Chemical group 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 8
- 150000001721 carbon Chemical group 0.000 claims description 6
- 125000002619 bicyclic group Chemical group 0.000 claims description 5
- 150000004820 halides Chemical class 0.000 claims description 5
- 150000002763 monocarboxylic acids Chemical class 0.000 claims description 5
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 5
- 239000002841 Lewis acid Substances 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- 125000000524 functional group Chemical group 0.000 claims description 4
- 150000007517 lewis acids Chemical class 0.000 claims description 4
- 239000003208 petroleum Substances 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 10
- 150000001735 carboxylic acids Chemical class 0.000 description 10
- 239000000203 mixture Substances 0.000 description 9
- -1 bicyclic hydrocarbons Chemical class 0.000 description 8
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N methyl pentane Natural products CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 125000002015 acyclic group Chemical group 0.000 description 5
- NBRKLOOSMBRFMH-UHFFFAOYSA-N tert-butyl chloride Chemical compound CC(C)(C)Cl NBRKLOOSMBRFMH-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 4
- 239000000061 acid fraction Substances 0.000 description 4
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 4
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 4
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 4
- MLMQPDHYNJCQAO-UHFFFAOYSA-N 3,3-dimethylbutyric acid Chemical compound CC(C)(C)CC(O)=O MLMQPDHYNJCQAO-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000012429 reaction media Substances 0.000 description 3
- 150000003509 tertiary alcohols Chemical class 0.000 description 3
- LTBPRPATSZONGJ-UHFFFAOYSA-N 2-(1-methylcyclohexyl)acetic acid Chemical compound OC(=O)CC1(C)CCCCC1 LTBPRPATSZONGJ-UHFFFAOYSA-N 0.000 description 2
- RXGNLXFTAIDOBZ-UHFFFAOYSA-N 3,3-dimethylhexanoic acid Chemical compound CCCC(C)(C)CC(O)=O RXGNLXFTAIDOBZ-UHFFFAOYSA-N 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000001282 iso-butane Substances 0.000 description 2
- 235000013847 iso-butane Nutrition 0.000 description 2
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 2
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methylcyclopentane Chemical compound CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- VTBOTOBFGSVRMA-UHFFFAOYSA-N 1-Methylcyclohexanol Chemical compound CC1(O)CCCCC1 VTBOTOBFGSVRMA-UHFFFAOYSA-N 0.000 description 1
- SQCZQTSHSZLZIQ-UHFFFAOYSA-N 1-chloropentane Chemical compound CCCCCCl SQCZQTSHSZLZIQ-UHFFFAOYSA-N 0.000 description 1
- NHCREQREVZBOCH-UHFFFAOYSA-N 1-methyl-1,2,3,4,4a,5,6,7,8,8a-decahydronaphthalene Chemical class C1CCCC2C(C)CCCC21 NHCREQREVZBOCH-UHFFFAOYSA-N 0.000 description 1
- FIPKSKMDTAQBDJ-UHFFFAOYSA-N 1-methyl-2,3-dihydro-1h-indene Chemical class C1=CC=C2C(C)CCC2=C1 FIPKSKMDTAQBDJ-UHFFFAOYSA-N 0.000 description 1
- CAKWRXVKWGUISE-UHFFFAOYSA-N 1-methylcyclopentan-1-ol Chemical compound CC1(O)CCCC1 CAKWRXVKWGUISE-UHFFFAOYSA-N 0.000 description 1
- AOPDRZXCEAKHHW-UHFFFAOYSA-N 1-pentoxypentane Chemical compound CCCCCOCCCCC AOPDRZXCEAKHHW-UHFFFAOYSA-N 0.000 description 1
- ZHQAIBYWBFMHHQ-UHFFFAOYSA-N 2-(1-methylcyclopentyl)acetic acid Chemical compound OC(=O)CC1(C)CCCC1 ZHQAIBYWBFMHHQ-UHFFFAOYSA-N 0.000 description 1
- UTENGZNBNPABQE-UHFFFAOYSA-N 2-[3-(carboxymethyl)-1-adamantyl]acetic acid Chemical compound C1C(C2)CC3CC1(CC(=O)O)CC2(CC(O)=O)C3 UTENGZNBNPABQE-UHFFFAOYSA-N 0.000 description 1
- YHQXBTXEYZIYOV-UHFFFAOYSA-N 3-methylbut-1-ene Chemical compound CC(C)C=C YHQXBTXEYZIYOV-UHFFFAOYSA-N 0.000 description 1
- PCWGTDULNUVNBN-UHFFFAOYSA-N 4-methylpentan-1-ol Chemical compound CC(C)CCCO PCWGTDULNUVNBN-UHFFFAOYSA-N 0.000 description 1
- YVHAIVPPUIZFBA-UHFFFAOYSA-N Cyclopentylacetic acid Chemical compound OC(=O)CC1CCCC1 YVHAIVPPUIZFBA-UHFFFAOYSA-N 0.000 description 1
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- UPURPFNAFBQPON-UHFFFAOYSA-N beta,beta-dimethyl valeric acid Chemical compound CCC(C)(C)CC(O)=O UPURPFNAFBQPON-UHFFFAOYSA-N 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000008246 gaseous mixture Substances 0.000 description 1
- RYPKRALMXUUNKS-UHFFFAOYSA-N hex-2-ene Chemical class CCCC=CC RYPKRALMXUUNKS-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000001308 synthesis method 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/093—Preparation of carboxylic acids or their salts, halides or anhydrides by hydrolysis of —CX3 groups, X being halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8216907 | 1982-10-08 | ||
| FR8216907A FR2534249B1 (fr) | 1982-10-08 | 1982-10-08 | Procede de preparation d'acides monocarboxyliques disubstitues en b derivant d'hydrocarbures acycliques ou cycliques |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL8303419A true NL8303419A (nl) | 1984-05-01 |
Family
ID=9278108
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8303419A NL8303419A (nl) | 1982-10-08 | 1983-10-05 | Werkwijze ter bereiding van beta-digesubstitueerde monocarbonzuren afkomstig van acyclische of cyclische koolwaterstoffen. |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4536594A (es) |
| JP (1) | JPS5988441A (es) |
| BE (1) | BE897933A (es) |
| CA (1) | CA1202642A (es) |
| DE (1) | DE3336572A1 (es) |
| ES (1) | ES526289A0 (es) |
| FR (1) | FR2534249B1 (es) |
| GB (1) | GB2132191B (es) |
| IT (1) | IT1163949B (es) |
| NL (1) | NL8303419A (es) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6677481B2 (en) | 2001-07-09 | 2004-01-13 | Exxonmobil Chemical Patents Inc. | Cracking of neo-C9 and neo-C13 carboxylic acids to either pivalic acid or methyl pivalate |
| US6686501B2 (en) * | 2002-02-05 | 2004-02-03 | Bayer Corporation | Processes for preparing 3.3-dimethylbutyric acid |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2370494A (en) * | 1942-11-09 | 1945-02-27 | Universal Oil Prod Co | Manufacture of alkanoic acids |
| US3308155A (en) * | 1963-02-25 | 1967-03-07 | Continental Oil Co | Preparation of 3, 3-disubstituted carboxylic acids |
| FR1489989A (fr) * | 1965-08-21 | 1967-07-28 | Huels Chemische Werke Ag | Procédé de préparation d'acides acétiques substitués par des restes alcoyliques |
| US3637821A (en) * | 1965-08-21 | 1972-01-25 | Huels Chemische Werke Ag | Process for the production of substituted acetic acids |
-
1982
- 1982-10-08 FR FR8216907A patent/FR2534249B1/fr not_active Expired
-
1983
- 1983-10-05 NL NL8303419A patent/NL8303419A/nl not_active Application Discontinuation
- 1983-10-06 IT IT23161/83A patent/IT1163949B/it active
- 1983-10-06 BE BE0/211656A patent/BE897933A/fr not_active IP Right Cessation
- 1983-10-06 ES ES526289A patent/ES526289A0/es active Granted
- 1983-10-07 CA CA000438641A patent/CA1202642A/fr not_active Expired
- 1983-10-07 GB GB08326837A patent/GB2132191B/en not_active Expired
- 1983-10-07 JP JP58187153A patent/JPS5988441A/ja active Pending
- 1983-10-07 DE DE19833336572 patent/DE3336572A1/de not_active Withdrawn
- 1983-10-07 US US06/540,118 patent/US4536594A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| GB2132191A (en) | 1984-07-04 |
| ES8405753A1 (es) | 1984-06-16 |
| GB2132191B (en) | 1987-06-24 |
| IT1163949B (it) | 1987-04-08 |
| IT8323161A0 (it) | 1983-10-06 |
| BE897933A (fr) | 1984-01-30 |
| DE3336572A1 (de) | 1984-04-12 |
| JPS5988441A (ja) | 1984-05-22 |
| ES526289A0 (es) | 1984-06-16 |
| FR2534249A1 (fr) | 1984-04-13 |
| US4536594A (en) | 1985-08-20 |
| CA1202642A (fr) | 1986-04-01 |
| GB8326837D0 (en) | 1983-11-09 |
| FR2534249B1 (fr) | 1986-04-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A85 | Still pending on 85-01-01 | ||
| BV | The patent application has lapsed |