An efficient route towards R-2-phenoxypropionic acid synthesis for biotransformative production of R-2-(4-hydroxyphenoxy)propionic acid  

作　　者：Haiyan Zhou Yizuo Li Rui Jiang Xianlin Wang Yuanshan Wang Yaping Xue Yuguo Zheng 

机构地区：[1]Key Laboratory ofBioorganic Synthesis of Zhejiang Province,College of Biotechnology and Bioengineering,Zhejiang University of Technology,Hangzhou 310014,China [2]Engineering Research Center of Bioconversion and Biopurification of Ministry of Education,Zhejiang University of Technology,Hangzhou 310014,China [3]The National and Local Joint Engineering Research Center for Biomanufacturing of Chiral Chemicals,Zhejiang University of Technology,Hangzhou 310014,China

出　　处：《Chinese Journal of Chemical Engineering》2021年第4期315-323,共9页中国化学工程学报（英文版）

基　　金：Haiyan Zhou,E-mail addresses:[e-mail];E-mail addresses:[e-mail];E-mail addresses:[e-mail](Y.Xue),[e-mail](Y.Zheng)。

摘　　要：R2(4hydroxyphenoxy)propionic acid(RHPPA)is a key intermediate for the synthesis of classic herbicides with high selectivity against grassy weed.The main route for RHPPA biosynthesis is to hydroxylate the substrate R2phenoxypropionic acid(RPPA)at C4 position with microbes.In order to provide sufficient RPPA for the industrial production of RHPPA,an effective RPPA synthesis method was established and optimized in this work.The synthesis process mainly consisted of two steps:(1)synthesis of S2chloropropionic acid from Lalanine via diazotization and chlorination reactions;and(2)synthesis of RPPA from S2chloropropionic acid and phenol via etherification reaction.The optimal reaction conditions were as follows:HCl:NaNO_(2):KI:LAla=2.0:1.2:0.7:1.0(in molar),125℃reflux for 1.5 h,with KI as catalyst,and KI:S2chloropropionic acid:phenol=0.075:1.2:1.0(in molar).Under these conditions,an improved molar conversion rate(74.9%,calculated in phenol)was achieved.After extraction using anionic exchange resin Amberlite IRA400(CI),RPPA product with a purity of 95.08%was obtained.The purified RPPA was identified and evaluated in the application of the biotransformative production of RHPPA.The results indicated that the synthesized RPPA supported the RHPPA biosynthesis with a comparable yield as that of the standard RPPA.The RPPA synthesis method provided herein exhibited the advantages of low price and easy availability of raw materials,less toxicity of reagents,simple manipulations,and low equipment/instrument requirements.

关 键 词：R-2-phenoxypropionic acid R-2-(4-hydroxyphenoxy)propionic acid BIOSYNTHESIS S-2-chloropropionic acid 

分 类 号：TQ457.2[化学工程—农药化工]