JPS6113698B2 - - Google Patents
Info
- Publication number
- JPS6113698B2 JPS6113698B2 JP57032537A JP3253782A JPS6113698B2 JP S6113698 B2 JPS6113698 B2 JP S6113698B2 JP 57032537 A JP57032537 A JP 57032537A JP 3253782 A JP3253782 A JP 3253782A JP S6113698 B2 JPS6113698 B2 JP S6113698B2
- Authority
- JP
- Japan
- Prior art keywords
- compound
- reaction
- group
- carried out
- nmr spectrum
- 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
- -1 acetylene compound Chemical class 0.000 claims description 16
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 8
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 7
- 239000010948 rhodium Substances 0.000 claims description 7
- 150000002576 ketones Chemical class 0.000 claims description 6
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 3
- 229910052703 rhodium Inorganic materials 0.000 claims description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 150000003284 rhodium compounds Chemical class 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 19
- 150000001875 compounds Chemical class 0.000 description 12
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 12
- 238000001819 mass spectrum Methods 0.000 description 10
- 230000000704 physical effect Effects 0.000 description 10
- 238000000921 elemental analysis Methods 0.000 description 7
- 239000013078 crystal Substances 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- JBFFAKAIUSEHAZ-MDZDMXLPSA-N (e)-2-methyl-1-phenylpent-1-en-3-one Chemical compound CCC(=O)C(\C)=C\C1=CC=CC=C1 JBFFAKAIUSEHAZ-MDZDMXLPSA-N 0.000 description 4
- UEXCJVNBTNXOEH-UHFFFAOYSA-N Ethynylbenzene Chemical group C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- JRXXLCKWQFKACW-UHFFFAOYSA-N biphenylacetylene Chemical group C1=CC=CC=C1C#CC1=CC=CC=C1 JRXXLCKWQFKACW-UHFFFAOYSA-N 0.000 description 4
- QVJOMQRREBIZOD-BQYQJAHWSA-N (e)-non-4-en-3-one Chemical compound CCCC\C=C\C(=O)CC QVJOMQRREBIZOD-BQYQJAHWSA-N 0.000 description 3
- CGHIBGNXEGJPQZ-UHFFFAOYSA-N 1-hexyne Chemical compound CCCCC#C CGHIBGNXEGJPQZ-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000005810 carbonylation reaction Methods 0.000 description 3
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- NJUYLHPEDBAUHE-UHFFFAOYSA-N methyl 2-benzylidene-3-oxopentanoate Chemical compound CCC(=O)C(C(=O)OC)=CC1=CC=CC=C1 NJUYLHPEDBAUHE-UHFFFAOYSA-N 0.000 description 3
- LYPLHWAXONFYCV-UHFFFAOYSA-N methyl 3-methyl-4-oxohex-2-enoate Chemical compound CCC(=O)C(C)=CC(=O)OC LYPLHWAXONFYCV-UHFFFAOYSA-N 0.000 description 3
- LVGUHATVVHIJET-CMDGGOBGSA-N (e)-1-phenylpent-1-en-3-one Chemical compound CCC(=O)\C=C\C1=CC=CC=C1 LVGUHATVVHIJET-CMDGGOBGSA-N 0.000 description 2
- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- KDKYADYSIPSCCQ-UHFFFAOYSA-N but-1-yne Chemical compound CCC#C KDKYADYSIPSCCQ-UHFFFAOYSA-N 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- LJKYONHSGXPCFY-UHFFFAOYSA-N C(CC)C(COC)CCOC Chemical compound C(CC)C(COC)CCOC LJKYONHSGXPCFY-UHFFFAOYSA-N 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- FXCLIEYDXXVEAI-UHFFFAOYSA-N benzene;dichloromethane Chemical compound ClCCl.C1=CC=CC=C1 FXCLIEYDXXVEAI-UHFFFAOYSA-N 0.000 description 1
- SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- JFGWPXKGINUNDH-UHFFFAOYSA-N methyl 3-phenylprop-2-ynoate Chemical compound COC(=O)C#CC1=CC=CC=C1 JFGWPXKGINUNDH-UHFFFAOYSA-N 0.000 description 1
- UJQCANQILFWSDJ-UHFFFAOYSA-N methyl but-2-ynoate Chemical compound COC(=O)C#CC UJQCANQILFWSDJ-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N methyl monoether Natural products COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- GHUURDQYRGVEHX-UHFFFAOYSA-N prop-1-ynylbenzene Chemical compound CC#CC1=CC=CC=C1 GHUURDQYRGVEHX-UHFFFAOYSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 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 |
|---|---|---|---|
| JP57032537A JPS58150533A (ja) | 1982-03-02 | 1982-03-02 | α，β−不飽和ケトンの製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57032537A JPS58150533A (ja) | 1982-03-02 | 1982-03-02 | α，β−不飽和ケトンの製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58150533A JPS58150533A (ja) | 1983-09-07 |
| JPS6113698B2 true JPS6113698B2 (de) | 1986-04-15 |
Family
ID=12361683
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57032537A Granted JPS58150533A (ja) | 1982-03-02 | 1982-03-02 | α，β−不飽和ケトンの製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58150533A (de) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8706767D0 (en) * | 1987-03-21 | 1987-04-23 | Bp Chem Int Ltd | Chemical process |
-
1982
- 1982-03-02 JP JP57032537A patent/JPS58150533A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS58150533A (ja) | 1983-09-07 |
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