Novel method for catalytically synthesizing benzyl salicylate via solid-liquid phase transfer

A technology of benzyl salicylate and solid-liquid phase, applied in chemical instruments and methods, preparation of organic compounds, catalytic reactions, etc., can solve the problems of high cost and high cost of benzyl alcohol, and achieve low cost, high reaction conversion rate and The effect of high selectivity and high product purity

Active Publication Date: 2015-04-29
江西省隆南药化有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The first is a traditional synthesis method using salicylic acid and benzyl alcohol as raw materials, but the cost of benzyl alcohol is relatively high; the second is the transesterification method of methyl salicylate and benzyl alcohol, and the product yield is about 82%. , the cost is also higher; the third is a liquid-liquid phase transfer catalytic reaction with salicylic acid, alkaline water and benzyl halide as raw materials, but because benzyl halide is easy to hydrolyze in high-temperature aqueous solution, the product yield is only about 83%

Method used

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  • Novel method for catalytically synthesizing benzyl salicylate via solid-liquid phase transfer

Examples

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Effect test

Embodiment 1

[0022] A new method for the synthesis of benzyl salicylate by solid-liquid phase transfer catalysis: Take 84.05g (525mmol) of sodium salicylate, 63.3g (500mmol) of benzyl chloride, crown ether (25mmol) and sodium iodide (3mmol), and add three mouthfuls In a bottom flask, react at 140℃ for 3h. After the reaction is complete, add water to separate the reaction liquid, separate the organic layer, wash the organic layer with distilled water, and then use NaHCO with a concentration of 5% by mass. 3 Wash twice with aqueous solution and then twice with distilled water. After dehydration and vacuum distillation, the fractions at 164-165°C / 730Pa are collected to obtain the benzyl salicylate product. The product is a colorless and transparent liquid with white needle-like crystals at low temperatures. Detected by gas chromatography, the product purity is 99.37%, and the product yield is 92.72%. The conversion rate of benzyl chloride was 98.62%, and the reaction selectivity was 94.02%.

Embodiment 2

[0024] A new method for the synthesis of benzyl salicylate by solid-liquid phase transfer catalysis: Take 96.1g (600mmol) of sodium salicylate, 63.3g (500mmol) of benzyl chloride, PEG-600 (25mmol) and potassium iodide (3mmol), add three round bottoms In the flask, react for 4 hours at a temperature of 145℃. After the reaction is completed, add water to separate the reaction liquid, separate the organic layer, wash the organic layer with distilled water, and then use NaHCO with a concentration of 5% by mass. 3 Wash twice with aqueous solution and then twice with distilled water. After dehydration and vacuum distillation, the fractions at 164-165°C / 730Pa are collected to obtain the benzyl salicylate product. The product is a colorless and transparent liquid with white needle-like crystals at low temperatures. Detected by gas chromatography, the product purity is 99.78%, and the product yield is 95.27%. The conversion rate of benzyl chloride was 98.91%, and the reaction selectivit...

Embodiment 3

[0026] A new method for the synthesis of benzyl salicylate by solid-liquid phase transfer catalysis: 315.05g (1.97mol) of sodium salicylate, 237.98g (1.88mmol) of benzyl chloride, PEG-2000 (94mmol) and potassium chloride (11.27mmol) , Put it into a three-necked round-bottom flask, react for 4h at a temperature of 145℃, after the reaction is complete, add water to separate the reaction liquid, separate the organic layer, wash the organic layer with distilled water, and then use 5% by mass NaHCO 3 Wash twice with aqueous solution and then twice with distilled water. After dehydration and vacuum distillation, the fractions at 164-165°C / 730Pa are collected to obtain the benzyl salicylate product. The product is a colorless and transparent liquid with white needle-like crystals at low temperatures. Detected by gas chromatography, the product purity is 99.40%, and the product yield is 94.13%. The conversion rate of benzyl chloride was 98.82%, and the reaction selectivity was 95.25%....

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Abstract

The invention relates to a novel method for catalytically synthesizing benzyl salicylate via solid-liquid phase transfer. The method comprises the following steps: adding salicylate, benzyl chloride, a catalyst A and a catalyst B in a reaction vessel for reaction at 80-200 DEG C for 2-20 h; after reaction, adding water to layer the reaction solution; separating the organic layer; carrying out washing, dehydration and reduced pressure distillation on the organic layer in sequence; collecting the fraction at 164-165 DEG C / 725-735 Pa to obtain the product, wherein the catalyst A is one or the combination of more than two of crown ether, a crown ether derivative and PEG200-6000 and the catalyst B is alkali metal haloid salt. The synthesis method provided by the invention has the advantages of being simple in process, low in energy consumption, less in pollution and high in yield and according with the international spice standard in the aspect of product quality.

Description

Technical field [0001] The invention relates to the field of organic synthesis, in particular to a new method for the synthesis of benzyl salicylate by solid-liquid phase transfer catalysis. Background technique [0002] Benzyl salicylate, also known as benzyl salicylate, has an ambergris and amber aroma. It is often used as a diluent, mixture and fixative for floral and non-floral fragrances. It is widely used in the fragrance industry. ; At the same time it is a cosmetic additive, used in sunscreen cosmetics, can protect the skin from UV damage; it can also be used as a modifier of pesticides and plastics, and as an intermediate of pharmaceutical products. [0003] Currently, there are three main methods for the synthesis of benzyl salicylate. The first is the traditional synthesis method using salicylic acid and benzyl alcohol as raw materials, but the cost of benzyl alcohol is relatively high; the second is the transesterification method of methyl salicylate and benzyl alcohol...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/84C07C67/10
CPCB01J31/26B01J2231/40C07C67/11C07C67/54C07C67/58C07C69/84
Inventor 肖国强陈康庆
Owner 江西省隆南药化有限公司
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