JPS6366302B2 - - Google Patents
Info
- Publication number
- JPS6366302B2 JPS6366302B2 JP55139132A JP13913280A JPS6366302B2 JP S6366302 B2 JPS6366302 B2 JP S6366302B2 JP 55139132 A JP55139132 A JP 55139132A JP 13913280 A JP13913280 A JP 13913280A JP S6366302 B2 JPS6366302 B2 JP S6366302B2
- Authority
- JP
- Japan
- Prior art keywords
- aluminum oxide
- carboxylic acid
- general formula
- unsaturated carboxylic
- formula
- 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
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 3
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims description 2
- 101150065749 Churc1 gene Proteins 0.000 claims description 2
- 102100038239 Protein Churchill Human genes 0.000 claims description 2
- 125000003262 carboxylic acid ester group Chemical class [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 150000001733 carboxylic acid esters Chemical class 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- -1 octadienoic acid ester Chemical class 0.000 description 3
- CIVIWCVVOFNUST-VFABXPAXSA-N Bombycol Natural products C(CCCCCCCC\C=C\C=CCCC)O CIVIWCVVOFNUST-VFABXPAXSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- OPCRGEVPIBLWAY-QNRZBPGKSA-N ethyl (2E,4Z)-deca-2,4-dienoate Chemical compound CCCCC\C=C/C=C/C(=O)OCC OPCRGEVPIBLWAY-QNRZBPGKSA-N 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- AWYPKJNGSOHXSR-UHFFFAOYSA-N CCCCCC=C=CCC(=O)OC Chemical compound CCCCCC=C=CCC(=O)OC AWYPKJNGSOHXSR-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- 238000000023 Kugelrohr distillation Methods 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000000877 Sex Attractant Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 239000003146 anticoagulant agent Substances 0.000 description 1
- 229960004676 antithrombotic agent Drugs 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- CIVIWCVVOFNUST-SCFJQAPRSA-N bombykol Chemical compound CCC\C=C/C=C/CCCCCCCCCO CIVIWCVVOFNUST-SCFJQAPRSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- KTQKFMPNYQEGLJ-UHFFFAOYSA-N ethyl deca-3,4-dienoate Chemical compound CCCCCC=C=CCC(=O)OCC KTQKFMPNYQEGLJ-UHFFFAOYSA-N 0.000 description 1
- XQILWIDABNBQOJ-UHFFFAOYSA-N ethyl hepta-2,4-dienoate Chemical compound CCOC(=O)C=CC=CCC XQILWIDABNBQOJ-UHFFFAOYSA-N 0.000 description 1
- QZHSXYRWSDHKJD-UHFFFAOYSA-N ethyl hepta-3,4-dienoate Chemical compound CCOC(=O)CC=C=CCC QZHSXYRWSDHKJD-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- GWNVDXQDILPJIG-NXOLIXFESA-N leukotriene C4 Chemical compound CCCCC\C=C/C\C=C/C=C/C=C/[C@H]([C@@H](O)CCCC(O)=O)SC[C@@H](C(=O)NCC(O)=O)NC(=O)CC[C@H](N)C(O)=O GWNVDXQDILPJIG-NXOLIXFESA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- WBVDAGWICYRIQQ-RCWDKCQFSA-N methyl (2E,4Z)-tetradeca-2,4-dienoate Chemical compound CCCCCCCCC\C=C/C=C/C(=O)OC WBVDAGWICYRIQQ-RCWDKCQFSA-N 0.000 description 1
- USOOLPVJOOLOKK-QNRZBPGKSA-N methyl (2e,4z)-undeca-2,4-dienoate Chemical compound CCCCCC\C=C/C=C/C(=O)OC USOOLPVJOOLOKK-QNRZBPGKSA-N 0.000 description 1
- GFJPZNNUBIFIFW-UHFFFAOYSA-N methyl tetradeca-3,4-dienoate Chemical compound CCCCCCCCCC=C=CCC(=O)OC GFJPZNNUBIFIFW-UHFFFAOYSA-N 0.000 description 1
- DOGOUGFZFAYSIB-UHFFFAOYSA-N methyl undeca-3,4-dienoate Chemical compound CCCCCCC=C=CCC(=O)OC DOGOUGFZFAYSIB-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical class OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 1
- JXJIQCXXJGRKRJ-KOOBJXAQSA-N pseudoionone Chemical compound CC(C)=CCC\C(C)=C\C=C\C(C)=O JXJIQCXXJGRKRJ-KOOBJXAQSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 239000008096 xylene Substances 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
- 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 |
|---|---|---|---|
| JP55139132A JPS5764643A (en) | 1980-10-03 | 1980-10-03 | Production of unsaturated carboxylic ester |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP55139132A JPS5764643A (en) | 1980-10-03 | 1980-10-03 | Production of unsaturated carboxylic ester |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5764643A JPS5764643A (en) | 1982-04-19 |
| JPS6366302B2 true JPS6366302B2 (fr) | 1988-12-20 |
Family
ID=15238267
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP55139132A Granted JPS5764643A (en) | 1980-10-03 | 1980-10-03 | Production of unsaturated carboxylic ester |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5764643A (fr) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0580807U (ja) * | 1992-04-08 | 1993-11-02 | セイレイ工業株式会社 | 分割タイヤ |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU604660B2 (en) * | 1985-12-17 | 1991-01-03 | Wellcome Foundation Limited, The | Pesticidal compounds |
-
1980
- 1980-10-03 JP JP55139132A patent/JPS5764643A/ja active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0580807U (ja) * | 1992-04-08 | 1993-11-02 | セイレイ工業株式会社 | 分割タイヤ |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5764643A (en) | 1982-04-19 |
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