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Abietic acid sulfur ether derivative and preparation method thereof

A technology of abietic acid thioether and abietic acid methylthiomethyl ester, which is applied in the field of abietic acid thioether derivatives and their preparation, can solve the problems of side reactions and high energy consumption, and achieve fast reaction speed, low acid value, and production high rate effect

Inactive Publication Date: 2011-01-19
GUANGXI UNIV FOR NATITIES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Therefore, the production of rosin ester often requires long-term reaction at high temperature, high energy consumption, and may cause a series of side reactions

Method used

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  • Abietic acid sulfur ether derivative and preparation method thereof
  • Abietic acid sulfur ether derivative and preparation method thereof
  • Abietic acid sulfur ether derivative and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0060] Add 2g of dehydroabietic acid (6.66mmol) and 0.0080g of catalyst potassium hydroxide to a 100mL round-bottomed flask with a reflux device, then add 10.50mL (11.45g, 146.5mmol) of dimethyl sulfoxide, and react at 215°C After 3 hours, unreacted DMSO was distilled off under reduced pressure to obtain 2.5 g of a crude product with an acid value of 6.5 mg KOH / g and a yield of 104%. Add 20mL of absolute ethanol to the crude product, stir and reflux in a magnetic heating stirrer to dissolve, add concentrated potassium hydroxide solution dropwise while stirring, adjust the pH of the solution to 9-10, and then reflux for half an hour to make potassium hydroxide and dehydrogenated arbores The acid is fully reacted, after cooling to room temperature, add distilled water to wash thoroughly, then filter with suction, add the filter cake to 0.03mol / L potassium hydroxide solution and stir at 50°C for 1-2 hours, filter with suction and wash with distilled water several times , to obtai...

Embodiment 2

[0062] Put 2g of common rosin (6.61mmol) and 0.0080g of potassium hydroxide in a 100mL round-bottomed flask with a reflux device, then add 10.50mL (11.45g, 146.5mmol) of dimethyl sulfoxide, and react at 215°C for 3 hours. Unreacted DMSO was distilled off under reduced pressure. The obtained crude product was 2.23g, and the yield was 92.9%. The acid value of the product was 6.39 mg KOH / g. The crude product was purified according to the method of Example 1 to obtain 1.42 g of the product with a yield of 59.17% and an acid value of 2.40 mg KOH / g.

Embodiment 3

[0064] Put 2g of disproportionated rosin and 0.0080g of potassium hydroxide in a 100mL round-bottomed flask with a reflux device, then add 10.50mL (11.45g, 146.5mmol) of dimethyl sulfoxide, react at 215°C for 3 hours, and distill under reduced pressure. Remove unreacted DMSO. The obtained crude product was 2.28g, and the yield was 95.0%. The acid value of the product was 5.56 mg KOH / g. The crude product was purified according to the method of Example 1 to obtain 1.46 g of the product with a yield of 60.83% and an acid value of 2.38 mg KOH / g.

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Abstract

The invention discloses an abietic acid sulfur ether derivative and a preparation method thereof. The name of the abietic acid sulfur ether derivative is abietic acid methylthio-methyl ester. The preparation method is that the abietic acid methylthio-methyl ester is prepared by directly esterifying common rosin, disproportionated rosin, dehydroabietic acid or hydrogenated rosin and dimethylsulfoxide serving as raw materials in the presence of a catalyst of potassium hydroxide. The abietic acid methylthio-methyl ester can be widely used in the fields such as coatings, printing ink, adhesives, synthetic rubber and the like. The abietic acid sulfur ether derivative has the advantages of: utilization of a new method for generating the abietic acid methylthio-methyl ester by directly performing an reaction on the common rosin, the disproportionated rosin, the dehydroabietic acid or the hydrogenated rosin and the dimethylsulfoxide in the presence of the catalyst of the potassium hydroxide, lower reaction temperature than a common esterification reaction, higher reaction speed, high yield, low product acid value and high stability, so the abietic acid sulfur ether derivative can be used as a plasticizer instead of abietate or applied in the industries such as coatings, printing ink and the like.

Description

technical field [0001] The invention relates to an abietic acid sulfide derivative and a preparation method thereof. Background technique [0002] The main component of rosin is diterpene resin acid C 19 h 29 COOH, the content is about 90%. Due to its large acid value, easy crystallization, it is difficult to be directly applied, and in practical applications, it is usually necessary to reduce its acid value through esterification and other reactions. However, due to the large steric hindrance effect in rosin molecules, the difficulty of esterification is higher than that of fatty acids ("Rosin Chemistry and Its Application", Ren Tianrui, Li Yonghong, Chemical Industry Press, 2006, 41-45). Therefore, the production of rosin ester often requires long-term reaction at high temperature, which consumes a lot of energy and may cause a series of side reactions. Therefore, it is of great application value to find a method of modifying rosin at a lower temperature. Contents of...

Claims

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Application Information

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IPC IPC(8): C07C323/12C07C319/14
Inventor 姚兴东汪影石展望雷福厚
Owner GUANGXI UNIV FOR NATITIES
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