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Method for preparing cinnamyl cinnamate

A technology of cinnamyl cinnamate and cinnamic acid, applied in the chemical field, can solve the problems of high cost, many by-products, and low yield of cinnamic acid, and achieve stable and reliable product quality, low production cost, and easy method Effect

Inactive Publication Date: 2008-08-13
湖北远成赛创科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Prepare cinnamyl cinnamate at present and have following several methods: 1, adopt hot caustic alkali solution to process natural styrax balsam, Peru balsam to extract cinnamyl cinnamate, this method produces and prepares cinnamyl cinnamate cost is higher, and raw material is hard to find, The process is complex and pollutes the environment seriously; 2. The cinnamyl cinnamate is prepared by transesterification of cinnamyl alcohol and ethyl cinnamate. Although the cinnamate obtained by this method will not touch the side chain double bond, the reaction must be carried out under high pressure. 3. Prepare cinnamoyl chloride by the reaction of cinnamic acid and thionyl chloride, and then react with cinnamyl alcohol in the presence of pyridine to synthesize cinnamyl cinnamate
Although the process of this synthesis method is relatively simple, the consumption of solvent is large, the by-products are many, the yield is low, the product is difficult to purify, and the solvent used is expensive, which is not cost-effective from an economic point of view.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0009] Dissolve 0.67mol cinnamic acid in 0.80mol thionyl chloride and stir evenly. At this time, the reaction temperature is -4 or -2 or 4 or 8°C, then slowly raise the temperature to 30 or 32 or 36 or 38 or 40°C, and keep warm for 2 After 1 hour, continue to heat up to 60 or 62 or 66 or 70 ℃ for 3 hours, complete, cool down to 20-30 ℃, recover unreacted thionyl chloride at normal pressure to 70 or 80 or 90 or 100 ℃. Then evacuate to -0.098Mpa, collect the distillates at a temperature controlled at 130-134°C to obtain 102g of cinnamoyl chloride finished product, with a yield of 91.4%. The product purity reaches 98.5%.

[0010] Take 0.6mol of cinnamyl alcohol, weigh the solvent according to the mass ratio of cinnamyl alcohol to N,N-dimethylaniline as 1:5, stir and heat up to 30 or 35 or 40 or 45 or 50°C, slowly add cinnamoyl chloride dropwise 99.9g, the dropwise addition time is about 3-5 hours, and the stirring reaction is continued for 3 hours. After completion, reduce the ...

Embodiment 2

[0012] Dissolve 0.67mol cinnamic acid in 1.34mol thionyl chloride and stir evenly. At this time, the reaction temperature is -5 or 7 or 12 or 17°C, and then the temperature is slowly raised to 30 or 31 or 33 or 39 or 40°C. After one hour, continue to heat up to 60 or 61 or 64 to 69 or 70 DEG C and react for 3 hours, complete, normal pressure reclaims unreacted thionyl chloride to 70 or 80 or 90 or 100 DEG C. Then evacuate to -0.090Mpa, collect and control the fraction at 178-181°C to obtain 108g of cinnamoyl chloride finished product, with a yield of 96.8%. The product purity reaches 98.5%.

[0013] Take 0.6mol of cinnamyl alcohol, weigh the solvent according to the mass ratio of cinnamyl alcohol to N,N-dimethylaniline as 1:5, stir and heat up to 30 or 33 or 37 or 41 or 47 or 50°C, slowly add Cinnamoyl chloride 68g, dropwise adding time is about 3 or 3.5 or 4 or 4.5 or 5 hours, continue to stir and react for 3 hours. Complete, reduce the pressure to -0.07Mpa and recover the ...

Embodiment 3

[0015] Dissolve 0.67mol of cinnamic acid in 0.80mol of thionyl chloride and stir evenly. At this time, the reaction temperature is -2 or 5 or 18 or 28 or 35°C, then slowly raise the temperature to 30 or 35 or 37 or 40°C, and keep the temperature for 2 hours Afterwards, continue to heat up to 60 or 63 or 68 or 70°C for 3 hours to react. After completion, cool down to 20-30°C, recover unreacted thionyl chloride at normal pressure to 70 or 80 or 90 or 100°C, and then evacuate to -0.1Mpa, the collected temperature was controlled at 125-127°C to obtain 103g of cinnamoyl chloride finished product, and the yield reached 92.3%. The product purity reaches 98.5%.

[0016] Take 0.6 mol of cinnamyl alcohol, weigh the solvent according to the mass ratio of cinnamyl alcohol to N,N-dimethylaniline as 1:5, stir and raise the temperature to 30 or 32 or 38 or 42 or 46 or 50°C, slowly drop Cinnamoyl chloride 50g, dropwise about 3 or 3.5 or 4 or 4.5 or 5 hours, continue stirring for 3 hours. Fi...

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PUM

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Abstract

The invention discloses a method for prepaing cinnamates, comprising steps of: A. heating materials of cinnamic acid and thionyl chloride to prepare rough cinnamoyl chloride, recoverying non-reacted thionyl chloride under atmospheric pressure, and air extracting to collect cinnamoyl chloride products; B. the cinnamoyl chloride products of the step A and cinnamyl alcohol materials are performed with heat preservation reaction and synthesis in the presence of an organic solvent to obatin rough cinnamates, recoverying the residual wastes of solvent by reduction and re-crystallizing the residual wastes by using methanol or ethanol to obtain cinnamate products. The method of the invention is simple, convenient in operation, low in material cost and high in yield. The method also has no pollution, and is very suitable for industrial production. The yield of producing cinnamates can reach 81.2%.

Description

technical field [0001] The invention belongs to the field of chemistry, and it is mainly used as a fixative in carnation, hyacinth, tuberose, succulent, sandalwood, white orchid, lily of the valley, magnolia and other daily essences, and can also be used in small amounts for fruit fragrances. Type food flavor. This patent more specifically relates to a preparation method of cinnamyl cinnamate. Background technique [0002] The chemical name of cinnamyl cinnamate is phenylpropenyl acrylate, which is an important fine chemical intermediate widely used in the production of medicines, spices and other products. Prepare cinnamyl cinnamate at present and have following several methods: 1, adopt hot caustic alkali solution to process natural styrax balsam, Peru balsam to extract cinnamyl cinnamate, this method produces and prepares cinnamyl cinnamate cost is higher, and raw material is hard to find, The process is complex and pollutes the environment ...

Claims

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Application Information

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IPC IPC(8): C07C69/618C07C67/08
Inventor 叶传发朱如慧余苗苗阮令飞华好好
Owner 湖北远成赛创科技有限公司
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