JPH0129181B2 - - Google Patents
Info
- Publication number
- JPH0129181B2 JPH0129181B2 JP57194000A JP19400082A JPH0129181B2 JP H0129181 B2 JPH0129181 B2 JP H0129181B2 JP 57194000 A JP57194000 A JP 57194000A JP 19400082 A JP19400082 A JP 19400082A JP H0129181 B2 JPH0129181 B2 JP H0129181B2
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- parts
- temperature
- unsaturated carbonyl
- hours
- 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
- 238000006243 chemical reaction Methods 0.000 claims description 37
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 13
- 239000003054 catalyst Substances 0.000 claims description 13
- -1 methylene compound Chemical class 0.000 claims description 13
- 238000004519 manufacturing process Methods 0.000 claims description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 10
- 238000003756 stirring Methods 0.000 description 7
- ILHZVKAXFCDFMT-UHFFFAOYSA-N 2-pentylcyclopent-2-en-1-one Chemical compound CCCCCC1=CCCC1=O ILHZVKAXFCDFMT-UHFFFAOYSA-N 0.000 description 6
- BEPAFCGSDWSTEL-UHFFFAOYSA-N dimethyl malonate Chemical compound COC(=O)CC(=O)OC BEPAFCGSDWSTEL-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 4
- 238000006845 Michael addition reaction Methods 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 2
- ZIXLDMFVRPABBX-UHFFFAOYSA-N 2-methylcyclopentan-1-one Chemical compound CC1CCCC1=O ZIXLDMFVRPABBX-UHFFFAOYSA-N 0.000 description 2
- BZKFMUIJRXWWQK-UHFFFAOYSA-N Cyclopentenone Chemical compound O=C1CCC=C1 BZKFMUIJRXWWQK-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 150000001733 carboxylic acid esters Chemical class 0.000 description 2
- ROZSFNKSMIZYLM-UHFFFAOYSA-N dimethyl 2-(3-oxo-2-pentylcyclopentyl)propanedioate Chemical compound CCCCCC1C(C(C(=O)OC)C(=O)OC)CCC1=O ROZSFNKSMIZYLM-UHFFFAOYSA-N 0.000 description 2
- MCVVUJPXSBQTRZ-ONEGZZNKSA-N methyl (e)-but-2-enoate Chemical compound COC(=O)\C=C\C MCVVUJPXSBQTRZ-ONEGZZNKSA-N 0.000 description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- IXAAKMCYKNWBRQ-UHFFFAOYSA-N 2-heptylcyclopent-2-en-1-one Chemical compound CCCCCCCC1=CCCC1=O IXAAKMCYKNWBRQ-UHFFFAOYSA-N 0.000 description 1
- VGECIEOJXLMWGO-UHFFFAOYSA-N 2-hexylcyclopent-2-en-1-one Chemical compound CCCCCCC1=CCCC1=O VGECIEOJXLMWGO-UHFFFAOYSA-N 0.000 description 1
- LFSAPCRASZRSKS-UHFFFAOYSA-N 2-methylcyclohexan-1-one Chemical compound CC1CCCCC1=O LFSAPCRASZRSKS-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical class C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- JHZPNBKZPAWCJD-UHFFFAOYSA-N ethyl 2-oxocyclopentane-1-carboxylate Chemical compound CCOC(=O)C1CCCC1=O JHZPNBKZPAWCJD-UHFFFAOYSA-N 0.000 description 1
- KKCYIFRLBUWHKG-UHFFFAOYSA-N ethyl 2h-chromene-2-carboxylate Chemical compound C1=CC=C2C=CC(C(=O)OCC)OC2=C1 KKCYIFRLBUWHKG-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- VQKIKHHXFHNXJT-UHFFFAOYSA-N hept-4-en-2-one Chemical compound CCC=CCC(C)=O VQKIKHHXFHNXJT-UHFFFAOYSA-N 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- FOBAEHIPCFVYAR-UHFFFAOYSA-N non-4-en-2-one Chemical compound CCCCC=CCC(C)=O FOBAEHIPCFVYAR-UHFFFAOYSA-N 0.000 description 1
- OMKNAWLMVVVCLD-UHFFFAOYSA-N oct-4-en-2-one Chemical compound CCCC=CCC(C)=O OMKNAWLMVVVCLD-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- RXJAOXZWWQADKO-UHFFFAOYSA-N trimethyl 2-methylpropane-1,1,3-tricarboxylate Chemical compound COC(=O)CC(C)C(C(=O)OC)C(=O)OC RXJAOXZWWQADKO-UHFFFAOYSA-N 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 |
|---|---|---|---|
| JP57194000A JPS5984843A (ja) | 1982-11-05 | 1982-11-05 | マイケル付加体の製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57194000A JPS5984843A (ja) | 1982-11-05 | 1982-11-05 | マイケル付加体の製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5984843A JPS5984843A (ja) | 1984-05-16 |
| JPH0129181B2 true JPH0129181B2 (de) | 1989-06-08 |
Family
ID=16317301
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57194000A Granted JPS5984843A (ja) | 1982-11-05 | 1982-11-05 | マイケル付加体の製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5984843A (de) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5347043A (en) * | 1993-12-20 | 1994-09-13 | Albemarle Corporation | Process for preparing Michael addition products |
| JP4781048B2 (ja) * | 2005-08-30 | 2011-09-28 | 日本曹達株式会社 | ジ置換β−ケトエステル類の製造方法 |
| JP4888766B2 (ja) * | 2006-07-11 | 2012-02-29 | 日東電工株式会社 | 多官能化合物の製造方法 |
-
1982
- 1982-11-05 JP JP57194000A patent/JPS5984843A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5984843A (ja) | 1984-05-16 |
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