CN103588642A - Synthetic method for mint benzoate - Google Patents
Synthetic method for mint benzoate Download PDFInfo
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- CN103588642A CN103588642A CN201210294449.4A CN201210294449A CN103588642A CN 103588642 A CN103588642 A CN 103588642A CN 201210294449 A CN201210294449 A CN 201210294449A CN 103588642 A CN103588642 A CN 103588642A
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- China
- Prior art keywords
- phenylformic acid
- menthol
- synthetic method
- solution
- benzoate
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention discloses a synthetic method for mint benzoate. The method comprises the following steps: adding menthol and benzoic acid according to a mol ratio of 1: 0.8-1.6 and adding the catalyst para-toluenesulfonic acid accounting for 1 to 4% of the weight of menthol and benzoic acid; carrying out heating reflux at a temperature of 95 to 102 DEG C, beginning timing when reflux appears and allowing a reaction to last for 2 to 10 h; after completion of the reaction, successively subjecting a cooled solution to washing with deionized water, washing with a sodium carbonate solution and liquid separation; carrying out drying by using anhydrous magnesium carbonate and removing magnesium sulfate through filtration after drying so as to obtain a clear light-yellow solution; and subjecting the solution to normal pressure distillation, removing cyclohexane through steaming at a temperature of 81 DEG C, subjecting a crude mint benzoate product to reduced pressure distillation and collecting a fraction obtained at 263 to 271 DEG C (5.8 kPa) as a product. According to the invention, para-toluenesulfonic acid is a good catalyst for synthesis of mint benzoate, and the synthetic method has the advantages of a high practical application value, high yield of mint benzoate and simple synthesis process.
Description
Technical field
The invention belongs to organic chemical synthesis field, be specifically related to a kind of synthetic method of phenylformic acid menthyl ester.
Background technology
Phenylformic acid menthyl ester is the light yellow transparent liquid with refrigerant peppermint taste, and it is a kind of important compound, as fixative, is applied to allocate daily chemical essence.Being mainly used in industry, daily chemical industry, is a kind of senior spices that needs focus development, has a extensive future.Conventionally esterification under sulfuric acid catalysis, there is environmental pollution and heavy corrosion in above-mentioned reaction, some troublesome poerations, cost is higher.In order to overcome above deficiency, once someone attempted to find different catalysts and catalyzed and synthesized isoamyl benzoate.Tosic acid is as a kind of strong organic acid, and side reaction is less than sulfuric acid, cheap and easy to get.
Summary of the invention
The invention provides a kind of method of P-toluene sulphonc acid menthyl ester.
According to amount of substance than menthol: phenylformic acid=1:0.8～1.6 add menthol and phenylformic acid, catalyzer tosic acid consumption is 1～4% of menthol and phenylformic acid weight, reflux at 95～102 ℃, start to have timing while refluxing, reaction 2～10h, Deng reaction finish after, cooling rear solution is used respectively to deionized water wash, sodium carbonate solution washing, separatory, anhydrous magnesium carbonate is dry, elimination sal epsom after dry, obtain clarifying yellow solution, solution is carried out to air distillation, in the time of 81 ℃, boil off hexanaphthene, the thick product of phenylformic acid menthyl ester is carried out to underpressure distillation, the cut of collecting 263～271 ℃ (5.8kPa) is product.
Preferably menthol and phenylformic acid amount of substance are than being 1:1.4.
Preferred catalyst tosic acid consumption is 3% of menthol and phenylformic acid weight.
Preferred back flow reaction 8h at 95～102 ℃.
Compare with the synthetic method of traditional phenylformic acid menthyl ester, tosic acid is the good catalysis chaste tree of synthesizing benzoic acids menthyl ester, has higher actual application value, and ester yield is higher, and the synthesis technique of experiment is simple.
Embodiment
Below in conjunction with embodiment, the synthetic method of phenylformic acid menthyl ester of the present invention is described in detail, thereby so that advantages and features of the invention can be easier to be it will be appreciated by those skilled in the art that, protection scope of the present invention is made to more explicit defining.
The raw material reagent that the present invention is used: phenylformic acid, menthol, tosic acid is analytical pure.
Embodiment 1
Agitator is being housed, temperature is taken into account in the 1000mL there-necked flask with the reflux condensing tube of water trap, the menthol that adds 156g, the Catalyzed by p-Toluenesulfonic Acid agent of the phenylformic acid of 97.6g and 2.5g, reflux is controlled temperature in 95～102 ℃, start to have timing while refluxing, reaction 10h, Deng reaction finish after, cooling rear solution is used respectively to deionized water wash, sodium carbonate solution washing, separatory, anhydrous magnesium carbonate is dry, elimination sal epsom after dry, obtain clarifying yellow solution, solution is carried out to air distillation, in the time of 81 ℃, boil off hexanaphthene, the thick product of phenylformic acid menthyl ester is carried out to underpressure distillation, the cut of collecting 263～271 ℃ (5.8kPa) is product, productive rate 65.3%.
Embodiment 2
Agitator is being housed, temperature is taken into account in the 1000mL there-necked flask with the reflux condensing tube of water trap, the menthol that adds 156g, the Catalyzed by p-Toluenesulfonic Acid agent of the phenylformic acid of 195.2g and 14g, reflux is controlled temperature in 95～102 ℃, start to have timing while refluxing, reaction 2h, Deng reaction finish after, cooling rear solution is used respectively to deionized water wash, sodium carbonate solution washing, separatory, anhydrous magnesium carbonate is dry, elimination sal epsom after dry, obtain clarifying yellow solution, solution is carried out to air distillation, in the time of 81 ℃, boil off hexanaphthene, the thick product of phenylformic acid menthyl ester is carried out to underpressure distillation, the cut of collecting 263～271 ℃ (5.8kPa) is product, productive rate 72.6%.
Embodiment 3
Agitator is being housed, temperature is taken into account in the 1000mL there-necked flask with the reflux condensing tube of water trap, the menthol that adds 156g, the Catalyzed by p-Toluenesulfonic Acid agent of the phenylformic acid of 170.8g and 9.8g, reflux is controlled temperature in 95～102 ℃, start to have timing while refluxing, reaction 8h, Deng reaction finish after, cooling rear solution is used respectively to deionized water wash, sodium carbonate solution washing, separatory, anhydrous magnesium carbonate is dry, elimination sal epsom after dry, obtain clarifying yellow solution, solution is carried out to air distillation, in the time of 81 ℃, boil off hexanaphthene, the thick product of phenylformic acid menthyl ester is carried out to underpressure distillation, the cut of collecting 263～271 ℃ (5.8kPa) is product, productive rate 80.2%.
Compare with the synthetic method of traditional phenylformic acid menthyl ester, tosic acid is the good catalysis chaste tree of synthesizing benzoic acids menthyl ester, has higher actual application value, and ester yield is higher, and the synthesis technique of experiment is simple.
Claims (4)
1. a synthetic method for phenylformic acid menthyl ester, it comprises the following steps:
According to amount of substance than menthol: phenylformic acid=1:0.8～1.6 add menthol and phenylformic acid, catalyzer tosic acid consumption is 1～4% of menthol and phenylformic acid weight, reflux at 95～102 ℃, start to have timing while refluxing, reaction 2～10h, Deng reaction finish after, cooling rear solution is used respectively to deionized water wash, sodium carbonate solution washing, separatory, anhydrous magnesium carbonate is dry, elimination sal epsom after dry, obtain clarifying yellow solution, solution is carried out to air distillation, in the time of 81 ℃, boil off hexanaphthene, the thick product of phenylformic acid menthyl ester is carried out to underpressure distillation, the cut of collecting 263～271 ℃ (5.8kPa) is product.
2. the synthetic method of phenylformic acid menthyl ester according to claim 1, is characterized in that: menthol and phenylformic acid amount of substance are than being 1:1.4.
3. the synthetic method of phenylformic acid menthyl ester according to claim 1, is characterized in that: catalyzer tosic acid consumption is 3% of menthol and phenylformic acid weight.
4. the synthetic method of phenylformic acid menthyl ester according to claim 1, is characterized in that: back flow reaction 8h at 95～102 ℃.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201210294449.4A CN103588642A (en) | 2012-08-17 | 2012-08-17 | Synthetic method for mint benzoate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201210294449.4A CN103588642A (en) | 2012-08-17 | 2012-08-17 | Synthetic method for mint benzoate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN103588642A true CN103588642A (en) | 2014-02-19 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201210294449.4A Withdrawn CN103588642A (en) | 2012-08-17 | 2012-08-17 | Synthetic method for mint benzoate |
Country Status (1)
| Country | Link |
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| CN (1) | CN103588642A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111892483A (en) * | 2020-08-03 | 2020-11-06 | 万香科技股份有限公司 | Method for resolving D, L-menthol |
| CN112409182A (en) * | 2020-11-30 | 2021-02-26 | 安徽丰乐香料有限责任公司 | Synthesis, purification and separation method of menthyl lactate |
-
2012
- 2012-08-17 CN CN201210294449.4A patent/CN103588642A/en not_active Withdrawn
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111892483A (en) * | 2020-08-03 | 2020-11-06 | 万香科技股份有限公司 | Method for resolving D, L-menthol |
| CN111892483B (en) * | 2020-08-03 | 2022-11-04 | 万香科技股份有限公司 | Method for resolving D, L-menthol |
| CN112409182A (en) * | 2020-11-30 | 2021-02-26 | 安徽丰乐香料有限责任公司 | Synthesis, purification and separation method of menthyl lactate |
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| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C04 | Withdrawal of patent application after publication (patent law 2001) | ||
| WW01 | Invention patent application withdrawn after publication |
Application publication date: 20140219 |