JPS5697250A - Preparation of acetylenecarboxylic ester - Google Patents
Preparation of acetylenecarboxylic esterInfo
- Publication number
- JPS5697250A JPS5697250A JP17248479A JP17248479A JPS5697250A JP S5697250 A JPS5697250 A JP S5697250A JP 17248479 A JP17248479 A JP 17248479A JP 17248479 A JP17248479 A JP 17248479A JP S5697250 A JPS5697250 A JP S5697250A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- acetylenic
- alcohol
- ester
- palladium
- 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.)
- Granted
Links
- -1 acetylenecarboxylic ester Chemical class 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 abstract 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 abstract 1
- 239000003905 agrochemical Substances 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 238000007083 alkoxycarbonylation reaction Methods 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- LLCSWKVOHICRDD-UHFFFAOYSA-N buta-1,3-diyne Chemical group C#CC#C LLCSWKVOHICRDD-UHFFFAOYSA-N 0.000 abstract 1
- 239000006227 byproduct Substances 0.000 abstract 1
- 229910002091 carbon monoxide Inorganic materials 0.000 abstract 1
- 150000007942 carboxylates Chemical class 0.000 abstract 1
- 150000001733 carboxylic acid esters Chemical class 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- JFGWPXKGINUNDH-UHFFFAOYSA-N methyl 3-phenylprop-2-ynoate Chemical compound COC(=O)C#CC1=CC=CC=C1 JFGWPXKGINUNDH-UHFFFAOYSA-N 0.000 abstract 1
- 239000007800 oxidant agent Substances 0.000 abstract 1
- 150000002941 palladium compounds Chemical class 0.000 abstract 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 abstract 1
- 239000002304 perfume Substances 0.000 abstract 1
- 239000001632 sodium acetate Substances 0.000 abstract 1
- 235000017281 sodium acetate Nutrition 0.000 abstract 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
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
PURPOSE: To obtain the titled compound which is an intermediate for perfumes, agricultural chemicals and medicines directly, by reacting a terminal acetylenic compound with an alcohol and CO in the presence of a catalyst.
CONSTITUTION: A terminal acetylenic compound is alkoxycarbonylated with an alcohol and carbon monoxide in the presence of a catalyst consisting of a palladium compound -oxidizing agent, e.g. palladium chloride -copper chloride, essentially to give an acetylenic carboxylic ester, e.g. methyl phenylacetylenecarboxylate. The reaction proceeds as shown in the reaction formulas, and the alkoxycarbonylation is carried out without the reduction of the acetylenic bond. An alkali carboxylate, e.g. sodium acetate, is preferably used to collect the hydrochloric acid and prevent the formation of diacetylene as a by-product.
COPYRIGHT: (C)1981,JPO&Japio
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17248479A JPS5697250A (en) | 1979-12-29 | 1979-12-29 | Preparation of acetylenecarboxylic ester |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17248479A JPS5697250A (en) | 1979-12-29 | 1979-12-29 | Preparation of acetylenecarboxylic ester |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5697250A true JPS5697250A (en) | 1981-08-05 |
| JPS6244539B2 JPS6244539B2 (en) | 1987-09-21 |
Family
ID=15942836
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP17248479A Granted JPS5697250A (en) | 1979-12-29 | 1979-12-29 | Preparation of acetylenecarboxylic ester |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5697250A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998046555A1 (en) * | 1997-04-15 | 1998-10-22 | Basf Aktiengesellschaft | Method for producing 2-alkynoic acid esters |
| WO2015182682A1 (en) * | 2014-05-29 | 2015-12-03 | 塩野義製薬株式会社 | Method for producing alkynyl ketone derivative |
| CN106964390A (en) * | 2017-02-24 | 2017-07-21 | 北京神雾环境能源科技集团股份有限公司 | Benzene catalyst processed and its production and use |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63200928U (en) * | 1987-06-16 | 1988-12-23 | ||
| JPH02143900U (en) * | 1989-05-09 | 1990-12-06 |
-
1979
- 1979-12-29 JP JP17248479A patent/JPS5697250A/en active Granted
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998046555A1 (en) * | 1997-04-15 | 1998-10-22 | Basf Aktiengesellschaft | Method for producing 2-alkynoic acid esters |
| US6153786A (en) * | 1997-04-15 | 2000-11-28 | Basf Aktiengesellschaft | Method for producing 2-alkynoic acid esters |
| WO2015182682A1 (en) * | 2014-05-29 | 2015-12-03 | 塩野義製薬株式会社 | Method for producing alkynyl ketone derivative |
| JPWO2015182682A1 (en) * | 2014-05-29 | 2017-04-20 | 塩野義製薬株式会社 | Process for producing alkynyl ketone derivative |
| US9951051B2 (en) | 2014-05-29 | 2018-04-24 | Shionogi & Co., Ltd. | Process for producing alkynylketone derivative |
| CN106964390A (en) * | 2017-02-24 | 2017-07-21 | 北京神雾环境能源科技集团股份有限公司 | Benzene catalyst processed and its production and use |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6244539B2 (en) | 1987-09-21 |
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