CN1616406A - Method for synthesizing L-menthol glycol carbonic ester - Google Patents
Method for synthesizing L-menthol glycol carbonic ester Download PDFInfo
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- CN1616406A CN1616406A CN 200310108627 CN200310108627A CN1616406A CN 1616406 A CN1616406 A CN 1616406A CN 200310108627 CN200310108627 CN 200310108627 CN 200310108627 A CN200310108627 A CN 200310108627A CN 1616406 A CN1616406 A CN 1616406A
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- Prior art keywords
- menthol
- reaction
- mentha camphor
- carbonic ester
- catalyzer
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Abstract
The present invention discloses a kind of L-menthol glycol carbonic ester synthesizing process. In the first step, menthol and ethyl chloroformate are reacted at 60 deg.c for 9-11 hr in the presence of catalyst pyridine or triethylamine to prepare to prepare L-menthol ethanol carbonic ester. In the second step, L-menthol ethanol carbonic ester and glycol produce alcohol exchange reaction of 10-15 hr to obtain L-menthol glycol carbonic ester at 125 deg.c and in the presence of catalyst MCM-41-TBD or HIGH-TDB. The present invention has the advantages of no use and production of phosgene and the catalyst MCM-41-TBD or HIGH-TDB used in the second step with high catalytic activity and capable of being reused.
Description
Technical field:
The present invention relates to be applied to the synthetic method of the L-mentha camphor ethylene carbonate of food and daily chemical products.
Background technology:
L-mentha camphor ethylene carbonate is a nature-identical, is characterized in being applicable to food and daily chemical products producing the refrigerant effect that the people is suited on the skin or on the human body mucous membrane.The synthetic way that adopts uses phosgene maybe can produce the material of phosgene in reaction process at present, and phosgene is all had relatively high expectations at transportation, storage, production unit, the cost height, and also acquisition is the L-mentha camphor ethylene carbonate of low yield.
Summary of the invention:
The present invention is directed to the shortcoming of prior art, a kind of synthetic method of improved L-mentha camphor ethylene carbonate is provided, obtained cheaply, the L-mentha camphor ethylene carbonate of higher yield.
The synthetic method of L-mentha camphor ethylene carbonate of the present invention is: at first synthetic L-mentha camphor ethanol carbonic ether, under the condition of reflux temperature and catalyzer, make L-mentha camphor ethanol carbonic ether with menthol and Vinyl chloroformate reaction, temperature of reaction is about 60 ℃, reaction times is 9～11 hours, and the catalyzer that reacts used is pyridine, triethylamine; Synthetic then L-mentha camphor ethylene carbonate: under the condition of high temperature and catalyzer, carry out pure permutoid reaction with L-mentha camphor ethanol carbonic ether and ethylene glycol, obtain L-mentha camphor ethylene carbonate, the catalyzer that reacts used is MCM-41-TBD, HI-TDB, temperature of reaction is about 125 ℃, and the reaction times is 15 hours.Its reaction is as follows:
The invention has the advantages that: avoid using phosgene maybe can produce the material of phosgene in reaction process, use can reuse and catalyzer efficiently, the efficiency of pcr product height.
Embodiment:
Further specify enforcement of the present invention below: the preparation of L-mentha camphor ethanol carbonic ether: the chloroform that in the 1000ml three-necked round bottom flask of agitator, dropping funnel, interior thermometer is housed, adds 250ml, 108.5 gram (1mol) Vinyl chloroformate, 78 gram (0.5mol) menthols, open and stir, Dropwise 5 5.5 gram (0.5mol) triethylamines under the room temperature, dropwised in about 1 hour, and in about 60 ℃, be incubated 8-10 hour again.Stop to stir, use dilute hydrochloric acid and water washing respectively, reclaim solvent then, underpressure distillation gets product 103 grams, content 98%, theoretical yield 90% again.
The preparation of L-mentha camphor ethylene carbonate: in the 500ml three-necked round bottom flask of agitator, dropping funnel, interior thermometer is housed, add 62 gram (1mol) ethylene glycol, 229 gram (1mol) L-mentha camphor ethanol carbonic ethers, 10 gram MCM-41-TBD, open and stir, reaction is 15 hours in about 125 ℃.Stop to stir, reaction mixture filters, and the solid that obtains washs with ether, obtains the catalyzer that can reuse.The filtered liquid underpressure distillation gets product 207.4 grams, content 98%, theoretical yield 85%.
Claims (1)
1. the synthetic method of a L-mentha camphor ethylene carbonate, it is characterized in that: the method for at first synthetic L-mentha camphor ethanol carbonic ether, under the condition of reflux temperature and catalyzer, make L-mentha camphor ethanol carbonic ether with menthol and Vinyl chloroformate reaction, temperature of reaction is about 60 ℃, reaction times is 9～11 hours, and the catalyzer that reacts used is pyridine, triethylamine; Synthetic then L-mentha camphor ethylene carbonate: under the condition of high temperature and catalyzer, carry out pure permutoid reaction with L-mentha camphor ethanol carbonic ether and ethylene glycol, obtain L-mentha camphor ethylene carbonate, the catalyzer that reacts used is MCM-41-TBD, HI-TDB, temperature of reaction is about 125 ℃, and the reaction times is 15 hours.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200310108627 CN1616406A (en) | 2003-11-14 | 2003-11-14 | Method for synthesizing L-menthol glycol carbonic ester |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200310108627 CN1616406A (en) | 2003-11-14 | 2003-11-14 | Method for synthesizing L-menthol glycol carbonic ester |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1616406A true CN1616406A (en) | 2005-05-18 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 200310108627 Pending CN1616406A (en) | 2003-11-14 | 2003-11-14 | Method for synthesizing L-menthol glycol carbonic ester |
Country Status (1)
| Country | Link |
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| CN (1) | CN1616406A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102153475A (en) * | 2011-01-27 | 2011-08-17 | 台州市尔康药业有限公司 | Preparation method for mint derivatives |
| CN103524349A (en) * | 2013-10-19 | 2014-01-22 | 山东大学 | CA-4 carbonate derivatives, and preparation method, pharmaceutical composition and medical application thereof |
| CN113979864A (en) * | 2021-11-12 | 2022-01-28 | 云南中烟工业有限责任公司 | One-pot synthesis method of novel menthol carbonate cooling agent and application of novel menthol carbonate cooling agent in cigarettes |
-
2003
- 2003-11-14 CN CN 200310108627 patent/CN1616406A/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102153475A (en) * | 2011-01-27 | 2011-08-17 | 台州市尔康药业有限公司 | Preparation method for mint derivatives |
| CN103524349A (en) * | 2013-10-19 | 2014-01-22 | 山东大学 | CA-4 carbonate derivatives, and preparation method, pharmaceutical composition and medical application thereof |
| CN103524349B (en) * | 2013-10-19 | 2015-09-09 | 山东大学 | CA-4 carbonates derivative, its preparation method, pharmaceutical composition and medicinal use |
| CN113979864A (en) * | 2021-11-12 | 2022-01-28 | 云南中烟工业有限责任公司 | One-pot synthesis method of novel menthol carbonate cooling agent and application of novel menthol carbonate cooling agent in cigarettes |
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| WD01 | Invention patent application deemed withdrawn after publication |