Optimization of synthesis processes of 2-(4-bromomethylphenyl)propionic acid

被引：0
|
作者：
Zhang Z.-M. [1 ]
Ye X.-Q. [1 ]
Gong H. [2 ]
Ruan S.-X. [1 ]
Qian C. [1 ]
Chen X.-Z. [1 ]
机构：
[1] Zhejiang Provincial Key Laboratory of Advanced Chemical Engineering Manufacture Technology, College of Chemical and Biological Engineering, Zhejiang University, Hangzhou
[2] Zhejiang Amino-Chem Co., Ltd., Shaoxing
来源：
Gao Xiao Hua Xue Gong Cheng Xue Bao/Journal of Chemical Engineering of Chinese Universities | 2019年 / 33卷 / 02期
关键词：
2-(4-bromomethylphenyl)propionic acid; 2-phenylpropionic acid; Bromomethylation; Gas phase cycling; Reaction-extraction;
D O I：
10.3969/j.issn.1003-9015.2019.02.021
中图分类号：
学科分类号：
摘要：
The synthesis process of 2-(4-bromomethylphenyl) propionic acid (BMPPA) was optimized by gas cycle and reaction-extraction, which solved the problems of large waste acid amounts and re-usage difficulty of traditional processes. In the gas-liquid-liquid reaction system, BMPPA was produced by the reaction of 2-phenylpropionic acid (PPA) with polyformaldehyde (PFA),which was catalyzed by zinc bromide (ZnBr2) in aqueous phase. BMPPA was extracted with organic phase. The gas phase was forced to circulate with the incoming hydrogen bromide gas to maintain hydrogen bromide concentration in the system, which also promoted mass transfer. The product was precipitated by organic phase cooling crystallization after reaction. The bulk liquor and aqueous phase were recycled. The optimized process conditions are as follows: molar ratio of ZnBr2:HBr:PFA:PPA is 0.5:2.5:1.5:1 and reaction at 80 ℃ for 8 hours with extractant of n-heptane. The yield of BMPPA is 86.7% after purification and the purity is 98%. This yield is stable even with water and organic phases are reused. Comparing with traditional processes, the waste acid emission is reduced by 80%. © 2019, Editorial Board of "Journal of Chemical Engineering of Chinese Universities". All right reserved.
引用
收藏
页码：418 / 424
页数：6
相关论文
共 17 条
  • [1] Lanza F.L., Codispoti J.R., Nelson E.B., An endoscopic comparison of gastroduodenal injury with over-the-counter doses of ketoprofen and acetaminophen, American Journal of Gastroenterology, 93, 7, pp. 1051-1054, (1998)
  • [2] Pirkle W.H., Liu Y., Design, synthesis, resolution, determination of absolute configuration, and evaluation of a chiral naproxen selector, Journal of Organic Chemistry, 59, 23, pp. 6911-6916, (1994)
  • [3] Willy Z., Thurnen S., Process of making 6-chloro-α-methyl-carbazole-2-acetic acid
  • [4] Terada A., Wachi K., Misaka E., Substituted phenylacetic acid derivatives and process for the preparation thereof
  • [5] Ma X.L., Study on synthesis of 2-(4-bromomethyl) phenylpropionic acid, (2015)
  • [6] Brenna E., Crotti M., Gatti F.G., Et al., Enantioselective synthesis of (R)-2-arylpropanenitriles catalysed by ene-reductases in aqueous media and in biphasic ionic liquid-water systems, Chemcatchem, 6, 8, pp. 2425-2431, (2014)
  • [7] Thiyagarajan S., Gunanathan C., Thiyaga R.S., Et al., Facile ruthenium(II)-catalyzed α-alkylation of arylmethyl nitriles using alcohols enabled by metal-ligand cooperation, Acs Catalysis, 7, 8, pp. 5483-5490, (2017)
  • [8] Dang T.T., Seayad A.M., A convenient ruthenium-catalysed α-methylation of carbonyl compounds using methanol, Advanced Synthesis & Catalysis, 358, 21, pp. 3373-3380, (2016)
  • [9] Xu X.L., He K.L., Lu X., Et al., Study on the synthesis of nonsteroidal anti-inflammatory drug loxoprofen sodium, Chinese Journal of Medicinal Chemistry, 24, 5, pp. 380-383, (2014)
  • [10] Feng J., Pan H.L., Yu Y.K., Et al., Study on the new synthetic process of loxoprofen sodium, Chemical Reagent, 38, 1, pp. 88-90, (2016)
12