CN101402570B - Method of preparing 5-methyl-5-hexenoic acid ethyl ester - Google Patents
Method of preparing 5-methyl-5-hexenoic acid ethyl ester Download PDFInfo
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- CN101402570B CN101402570B CN2008101362697A CN200810136269A CN101402570B CN 101402570 B CN101402570 B CN 101402570B CN 2008101362697 A CN2008101362697 A CN 2008101362697A CN 200810136269 A CN200810136269 A CN 200810136269A CN 101402570 B CN101402570 B CN 101402570B
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- hexenoic acid
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Abstract
The invention relates to a method for making 5-methyl-5-ethyl hexenoate. The method uses ethyl acrylate as a raw material, and the 5-methyl-5-ethyl hexenoate is obtained by addition reaction of the ethyl acrylate and isobutene under the presence of a catalyst, wherein the catalyst is anhydrous stannic chloride particularly, the feeding molar ratio of the ethyl acrylate to the isobutene is 1 to 2-3, and the catalyst accounts for 0.8 to 1.5 percent of the mass of the ethyl acrylate. The method has more than 50 percent of yield and has low cost for producing the 5-methyl-5-ethyl hexenoate.
Description
Technical field
The present invention relates to the preparation method of a kind of 5-methyl-5-hexenoic acid ethyl ester.
Background technology
In the prior art; The method a kind of commonly used that addition reaction is preparation 5-methyl-5-hexenoic acid ethyl ester takes place in ethyl propenoate and iso-butylene in the presence of catalyzer; Catalyzer is mainly aluminum chloride, zinc chloride, boron trifluoride etc.; This method yield is low, only can reach about 20%, causes product cost higher thus.
Summary of the invention
Technical problem to be solved by this invention provides the preparation method of the high 5-methyl-5-hexenoic acid ethyl ester of a kind of yield.
For solving above technical problem, the present invention takes following technical scheme:
The preparation method of a kind of 5-methyl-5-hexenoic acid ethyl ester; With the ethyl propenoate is raw material; Addition reaction takes place and generates 5-methyl-5-hexenoic acid ethyl ester in itself and iso-butylene in the presence of catalyzer, particularly, said catalyzer is an anhydrous stannic chloride; The molar ratio of ethyl propenoate and iso-butylene is 1:2～3, and catalyst levels is 0.8%～1.5% of an ethyl propenoate quality.
The molar ratio of ethyl propenoate and iso-butylene is preferably 1:2.1～2.5.
Catalyst levels is preferably 1%～1.2% of ethyl propenoate quality.
Because the technique scheme utilization, the present invention compared with prior art has advantage:
Finding through a large amount of experiments, is catalyzer when adopting anhydrous stannic chloride, and when making the relative ethyl propenoate of iso-butylene excessive greatly, this addition reaction has higher yield (more than 50%), thereby reduces the production cost of 5-methyl-5-hexenoic acid ethyl ester.
Embodiment
Below in conjunction with concrete embodiment the present invention is done further detailed explanation, but be not limited thereto embodiment.
In the 500ML four-hole boiling flask, add ethyl propenoate 50G, benzene 220G and 5.5G anhydrous stannic chloride, 10 ℃ of controlled temperature feed iso-butylene 120G, logical 24 hours; Be incubated 6 days below 20 ℃, add 13% sodium bicarbonate aqueous solution 115G then, stirred 0.5 hour, add the mixed solution of 20G36% hydrochloric acid and 80G water again, stirred 0.5 hour; Static 0.5 hour, layering divided the sub-cloud water layer, uses the 200G water washing; Divide the sub-cloud water layer, the benzene layer is put into bucket, adds the anhydrous magnesium sulfate dehydration and spends the night, and is concentrated into 50～60ML volume; Elder generation reduces pressure behind the normal pressure, puts into rectifying still rectifying then, and about 95 ℃ of still temperature the highlyest are no more than 120 ℃; About 75 ℃ of top temperature, about 100～130 ℃ of chucks are collected the fraction that just boiling, and get product 40G; Wherein, 5-methyl-5-hexenoic acid ethyl ester content >=97%, in 5-methyl-5-hexenoic acid ethyl ester, molar yield is 51.2%.
Claims (1)
1. the preparation method of 5-methyl-5-hexenoic acid ethyl ester is a raw material with the ethyl propenoate, and itself and iso-butylene addition reaction take place in the presence of catalyzer generate 5-methyl-5-hexenoic acid ethyl ester, and it is characterized in that: said method is specially: in the 500ml four-hole boiling flask, add ethyl propenoate 50G, benzene 220G and 5.5G anhydrous stannic chloride; 10 ℃ of controlled temperature feed iso-butylene 120G, and logical 24 hours, insulation below 20 ℃ 6 days; Add 13% sodium bicarbonate aqueous solution 115G then, stirred 0.5 hour, add the mixed solution of 20G 36% hydrochloric acid and 80G water again, stirred 0.5 hour; Static 0.5 hour, layering divided the sub-cloud water layer, uses the 200G water washing; Divide the sub-cloud water layer, the benzene layer is put into bucket, adds the anhydrous magnesium sulfate dehydration and spends the night, and is concentrated into 50～60ml volume; Elder generation reduces pressure behind the normal pressure, puts into rectifying still rectifying then, and 95 ℃ of still temperature the highlyest are no more than 120 ℃; 75 ℃ of top temperature, 100～130 ℃ of chucks are collected the fraction that just boiling, and get product 40G; Wherein, 5-methyl-5-hexenoic acid ethyl ester content >=97%, in 5-methyl-5-hexenoic acid ethyl ester, molar yield is 51.2%.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2008101362697A CN101402570B (en) | 2008-11-20 | 2008-11-20 | Method of preparing 5-methyl-5-hexenoic acid ethyl ester |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
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| CN2008101362697A CN101402570B (en) | 2008-11-20 | 2008-11-20 | Method of preparing 5-methyl-5-hexenoic acid ethyl ester |
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| CN101402570A CN101402570A (en) | 2009-04-08 |
| CN101402570B true CN101402570B (en) | 2012-03-07 |
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| CN2008101362697A Active CN101402570B (en) | 2008-11-20 | 2008-11-20 | Method of preparing 5-methyl-5-hexenoic acid ethyl ester |
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Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102838474A (en) * | 2012-09-25 | 2012-12-26 | 天宁香料（江苏）有限公司 | Synthesis method for trans-3-hexenoic acid |
| CN112062676B (en) * | 2019-06-11 | 2022-05-24 | 太仓市茜泾化工有限公司 | Preparation method of 5-methyl-5-hexenoic acid ethyl ester |
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2008
- 2008-11-20 CN CN2008101362697A patent/CN101402570B/en active Active
Non-Patent Citations (3)
| Title |
|---|
| Athelstan L.J. Beckwith and Graeme Moad.《Aluminium-chloride-promoted reactions of ethyl acrylate with olefins》.《Aust.J.Chem.》.1977,第30卷2733-2739. |
| Athelstan L.J. Beckwith and Graeme Moad.《Aluminium-chloride-promoted reactions of ethyl acrylate with olefins》.《Aust.J.Chem.》.1977,第30卷2733-2739. * |
| WILLIAM T . COMER AND DAVIS L. TEMPLE.《The Reaction of Cyclopentanones with Methylsulfinyl Carbanion》.《J.Org.Chem.》.1973,第38卷(第12期),2121-2125. * |
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| CN101402570A (en) | 2009-04-08 |
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