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Preparation and separation method of high-purity p-acrylic pimaric acid

A technology of acrylopimaric acid and a separation method, which is applied in the separation/purification of carboxylic acid compounds, preparation of carboxylate, preparation of organic compounds, etc., can solve the problems of complicated operation, product separation and characterization, and high cost, and achieves good repeatability. Effect

Active Publication Date: 2016-07-27
南昌市龙然实业有限公司
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  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Cao Qifeng et al. (Cao Qifeng, Zhu Changchun, Song Wensheng, et al. Synthesis of acrylic acid modified rosin. China Adhesives, 2007,16(12):26-28) synthesized acrylic acid modified rosin, but only discussed acrylic modified rosin The acid value and softening point of rosin did not give the GC content of APA under optimized conditions, and did not separate and characterize the specific structure of the product; Lin Mingtao et al. (Lin Mingtao, Wang Jifu, Liu Yupeng, et al. Research. Applied Chemical Industry, 2012,41(5):802-806) has studied in detail the reaction of each resin acid in the reaction process of rosin resin acid and acrylic acid Diels-Alder. In the process of addition, even if acrylic acid is excessive, abietic acid Type resin acid also can not participate in reaction fully, and unreacted resin acid and abietic acid content have accounted for 2% and 7% respectively, and deduced by theory that the ratio of the substance amount of para-position product and meta-position product is 4:1, However, no specific separation and analysis of the two isomers
The results of the propylene pimaric acid obtained by the above method are not ideal, or the usage of the solvent is large, the cost is high, or it has to be separated by repeated recrystallization, the operation is cumbersome, and the separation effect is not good.

Method used

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preparation example Construction

[0018] A method for separating and preparing p-propylenepimaric acid, using rosin and acrylic acid as raw materials, and preparing acrylic acid-modified rosin through Diels-Alder reaction under microwave-assisted conditions. Using acrylic acid-modified rosin or its purified product, acrylic pimaric acid, as raw materials, using benzene and ethyl acetate as developing agents, continuously adding developing agents to a cyclodextrin-modified silica gel chromatography column with a particle size of 0.044-0.075 mm, from Collect p-propylenepimaric acid from the fractionated eluate obtained. The specific column chromatography processing steps are as follows:

[0019] Cyclodextrin-modified silica gel: 1) Weigh 7g of TLC silica gel and put it into a 250mL flask, add 35mL of benzene, 40mL of thionyl chloride, reflux for 10h under stirring, filter after the reaction, and put the product at 90 ℃ into a vacuum drying oven to dry, after drying a white powder. 2) Weigh 9g of hydroxypropyl-...

Embodiment 1

[0025] Add 10g of rosin and 2.4g of acrylic acid into the flask, place it in a microwave reaction workstation, and prepare acrylic acid-modified rosin under the conditions of microwave power 300W, reaction temperature 230°C, and reaction time 90min. Using this acrylic acid-modified rosin as a raw material, using benzene and ethyl acetate as a developer with a volume ratio of 5:1, passing through a 0.044-0.075mm cyclodextrin-modified silica gel column, and concentrating the extract to dryness to obtain p-propylene Pimaric acid. The yield of isolated p-propylenepimaric acid was 35.4%, and the GC content of p-propylenepimaric acid obtained by column chromatography was 85.6%.

Embodiment 2

[0027] Add 10g of rosin and 4.8g of acrylic acid into the flask, place it in a microwave reaction workstation, and prepare acrylic acid-modified rosin under the conditions of microwave power 400W, reaction temperature 200°C, and reaction time 110min. Using this acrylic acid-modified rosin as raw material, using benzene and ethyl acetate volume ratio of 8:1 as the developer, passing through a 0.044-0.075mm cyclodextrin-modified silica gel column, and concentrating the extract to dryness to obtain p-propylene Pimaric acid. The yield of p-propylenepimaric acid obtained by separation was 29.7%, and the GC content of p-propylenepimaric acid obtained by column chromatography was 85.6%.

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Abstract

The invention relates to a preparation and separation method of high-purity p-acrylic pimaric acid and discloses a preparation and separation method of p-acrylic pimaric acid. The preparation and separation method comprises steps as follows: 1) rosin and acrylic acid are taken as raw materials and subjected to a Diels-Alder reaction under the microwave-assisted condition, and acrylic acid modified rosin is obtained; 2) acrylic pimaric acid is obtained through purification; 3) a p-acrylic pimaric acid product is prepared from the acrylic acid modified rosin or acrylic pimaric acid serving as a raw material through cyclodextrin modified silica gel column chromatography with benzene and ethyl acetate in different volume ratios as developing solvents and has the purity higher than 95%. The method is simple, convenient, efficient and high in repeatability, the obtained p-acrylic pimaric acid has high purity and can be used as a high-purity chemical material or an intermediate, and additional utilization values of rosin can be effectively increased.

Description

technical field [0001] The invention relates to a preparation method of rosin derivative propylene pimaric acid, in particular to a product with p-propylene pimaric acid (para-propylene pimaric acid) with a purity greater than 95% and a preparation method thereof. Background technique [0002] Rosin is an important renewable resource in my country, and its output and export volume have always ranked first in the world, but there are relatively few intensively processed products. Therefore, the development of high value-added products of rosin is of great significance to my country's rosin industry. The main component of rosin is resin acid, which usually contains a carboxyl functional group. Through chemical modification, the carboxyl group of resin acid can undergo various structural changes to form a variety of rosin-based derivative chemicals. Propylenepimaric acid is the modified product of rosin, contains two carboxyl functional groups, can prepare multiple novel rosin...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C51/47C07C51/353C07C61/29
CPCC07C51/353C07C51/47C07C61/29
Inventor 卢言菊赵振东陈玉湘古研王婧徐士超毕良武李冬梅
Owner 南昌市龙然实业有限公司
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