Acrylpimaric acid diallyl ester and microwave-assisted synthesis method thereof

A technology of diallyl acrylopimarate and sodium acrylopimarate, which is applied in the product and preparation field of diallyl pimalate, can solve the problems that the hardness and other properties of the polymer product cannot meet the application requirements, the operation is cumbersome, and the reaction Long time and other problems, to achieve the effect of short reaction time, good purity and simple post-processing

Inactive Publication Date: 2016-03-16
INST OF CHEM IND OF FOREST PROD CHINESE ACAD OF FORESTRY
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  • Abstract
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  • Application Information

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Problems solved by technology

Wang Jifu, et al. Allyl maleopimarate was synthesized by the method of acyl chloride and then esterification, and the structure and performance of the product were characterized and determined. The obtained product can undergo polymerization reaction when heated above the melting point, and can be used as epoxy resin and non-toxic Saturated resin prepolymer, but the method of esterification after acyl chloride is used, the operation is cumbersome and the reaction time is long
Lu Yanju et al. (YanjuLu, ZhendongZhao, YanGu, et al. Synthesis of rosinally lester and its UV-curing characteristics [J]. PolymerJournal, 2011, 43: 869-873) synthesized allyl resinate and studied its UV curing properties, the synthesized product itself can be Free radical polymerization occurs, and the degree of polymerization can reach 27, but the generated polymer is a long-chain product, and the hardness and other properties of the polymerized product cannot meet the application requirements
[0005] The present invention uses microwave-assisted-phase transfer catalysis combined technology to rapidly synthesize propylene pimarate diallyl ester with two polymerization functionalities and its technical method has not been reported in the literature

Method used

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  • Acrylpimaric acid diallyl ester and microwave-assisted synthesis method thereof
  • Acrylpimaric acid diallyl ester and microwave-assisted synthesis method thereof
  • Acrylpimaric acid diallyl ester and microwave-assisted synthesis method thereof

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[0029] A kind of propylene pimarate diallyl product and microwave-assisted synthesis method thereof, its synthetic method comprises the steps: in the presence of propylene pimarate sodium and chloropropene in the presence of a quaternary ammonium salt catalyst and a polymerization inhibitor, with a strong polar organic solvent As a reaction medium, react for 10-120 minutes under the conditions of microwave power of 300-800W and microwave temperature of 40-90°C. After the reaction is complete, remove NaCl by filtration, add a certain amount of organic solvent for extraction, pour into a separatory funnel and shake well, let stand to separate layers, take the organic solvent layer, wash with distilled water until neutral, and remove the organic solvent by rotary evaporation to obtain a viscous liquid for the product. The product, propylenepimarate diallyl, is an isomer, and its main components are p-propylenepimarate diallyl and m-propylenepimarate diallyl, with a GC content exc...

Embodiment 1～16

[0046] In a 100mL three-necked microwave special flask, add allyl chloride and sodium propylene pimarate in a certain ratio of substances, add a certain amount of hexadecyltrimethylammonium bromide, and use 0.2% hydroquinone as a polymerization inhibitor. 25mL of N,N-dimethylformamide as a solvent, a certain volume of allyl chloride, magnetically stirred, condensed and refluxed, heated to a specific temperature to react for a period of time, filtered to remove the generated NaCl after the reaction, and the filtrate was extracted 3 times with n-hexane , 50mL each time, combined, washed with water until neutral, dried over anhydrous sodium sulfate, and removed n-hexane by rotary evaporation to obtain the product. Weigh the quality of the product obtained and calculate the yield. The results of Examples 1 to 16 are summarized in Table 1.

[0047] The influence of each factor of table 1 on the synthesis of diallyl propylene pimarate

[0048]

[0049]

Embodiment 17

[0051] In a 100mL three-necked microwave special flask, add allyl chloride and propylene pimarate at a ratio of 5:1, add 4% tetrabutylammonium bromide as a catalyst, and 0.3% phenothiazine as a polymerization inhibitor, 25mL N,N-dimethylformamide was used as a solvent, magnetically stirred, condensed and refluxed, heated to 55°C under the condition of microwave power of 400W and reacted for 90min. , 50 mL each time, combined, washed with water until neutral, dried over anhydrous sodium sulfate, and removed n-hexane by rotary evaporation to obtain the product with a yield of 72.7%.

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Abstract

The invention discloses acrylpimaric acid diallyl ester and a microwave-assisted synthesis method thereof. The method comprises steps as follows: rosin and acrylic acid react, a modified product is prepared, then acrylpimaric acid sodium salt is prepared and has a microwave-assisted synthesis reaction with chloropropene in the presence of a quaternary ammonium salt catalyst and a polymerization inhibitor at a certain temperature for a period of time, NaCl is filtered and removed after the reaction, a certain quantity of an organic solvent is added for extraction, an obtained solution is poured into a separating funnel, is shaken up and then is left to stand for layering, an organic solvent layer is taken and washed with distilled water to be neutral, the organic solvent is removed through rotary evaporation, and a sticky liquid, namely a product, is obtained. The product yield is high, the purity is good, the yield can be up to 92.2%, and the GC content is 98.6%. N, N-dimethylformamide or dimethyl sulfoxide is taken as a reaction medium for the reaction. With the adoption of microwave heating, the radiation energy is high, the efficiency is high, the reaction time is short, the operation is simple and convenient, the product is easy to separate, the product yield is high, and the purity is good.

Description

technical field [0001] The invention relates to a product and a preparation method of diallyl propylene pimarate, and mainly relates to an innovative product diallyl propylene pimarate and a process method for preparing it using microwave-assisted synthesis technology. Background technique [0002] Rosin is an important renewable resource product in my country and one of the important chemical raw materials. It is usually used for high value-added utilization after deep processing. Acrylic acid modification is one of the important methods for the deep processing and utilization of rosin. The acrylic rosin produced by it is further chemically modified to form a polymeric monomer with a terminal double bond structure, which can not only retain the skeleton structure of rosin to the greatest extent, but also increase the number of active functional group terminals. The double bond structure is conducive to the synthesis of polymer materials with different degrees of polymerizat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/11C07C69/753
CPCC07C67/11C07C69/753
Inventor 卢言菊赵振东陈玉湘古研王婧徐士超毕良武李冬梅
Owner INST OF CHEM IND OF FOREST PROD CHINESE ACAD OF FORESTRY
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