Green Chemistry p. 6444 - 6454 (2020)
Update date:2022-08-16
Topics:
Carraher, Jack M.
Carter, Prerana
Cochran, Eric W.
Forrester, Michael J.
Pfennig, Toni
Rao, Radhika G.
Shanks, Brent H.
Tessonnier, Jean-Philippe
The quest for green plastics calls for new routes to aromatic monomers using biomass as a feedstock. Suitable feedstock molecules and conversion pathways have already been identified for several commodity aromatics through retrosynthetic analysis. However, this approach suffers from some limitations as it targets a single molecule at a time. A more impactful approach would be to target bioprivileged molecules that are intermediates to an array of commodity and specialty chemicals along with novel compounds. Muconic acid (MA) has recently been identified as a bioprivileged intermediate as it gives access to valuable aliphatic and cyclic diacid monomers including terephthalic acid (TPA), 1,4-cyclohexanedicarboxylic acid (CHDA), and novel monounsaturated 1,4-cyclohexenedicarboxylic acids (CH1DA, CH2DA). However, accessing these cyclic monomers from MA requires to first isomerize biologically-produced cis,cis-MA to Diels-Alder active trans,trans-MA. A major impediment in this isomerization is the irreversible ring closing of MA to produce lactones. Herein, we demonstrate a green solvent-mediated isomerization using dimethyl sulfoxide and water. The mechanistic understanding achieved here elucidates the role of low concentrations of water in reducing the acidity of the system, thereby preventing the formation of lactones and improving the selectivity to trans,trans-MA from less than 5% to over 85%. Finally, a Diels-Alder reaction with trans,trans-MA is demonstrated with ethylene. The monounsaturated cyclic diacid obtained through this reaction (CH1DA) can be converted in a single step into TPA and CHDA, or can be directly copolymerized with adipic acid and hexamethylenediamine to tailor the thermal and mechanical properties of conventional Nylon 6,6.
View MoreSHANDONG ZHANHUA YONGHAO PHARMACEUTICAL TECH.CO.,LTD
Contact:+86-576-88685096
Address:GENGJU VILLAGE NORTH ONE KILOMETER,ZHANHUA DISTRICT,BINZHOU CITY,SHANDONG PROVINCE,CHINA.
Quzhou Ruiyuan chemical Co., Ltd
Contact:+86-570-3039321/3039361/3039308
Address:18# Huayang Road,Quzhou High-tech Industrial Park, Zhejiang China.
Contact:86-536-8866010
Address:NO.4455 EAST FUSHOU ST. WEIFANG DEVELOPMENT ZONE, SHANDONG, CHINA
Contact:+86-021-6989-5597
Address:No.80 Yichuan Rd., Putuo District,Shanghai,P.R.China
Guangxi Shanyun Biochemical Science and Technology Co., Ltd
Contact:+86-0772--6828887
Address:#2 Industrial Park of Luzhai County, Liuzhou, Guangxi, China
Doi:10.1016/j.apcata.2018.12.004
(2019)Doi:10.1007/s00044-019-02422-5
(2019)Doi:10.1002/adsc.200600254
(2006)Doi:10.1016/S0040-4039(01)93768-2
(1989)Doi:10.1007/s11172-008-0205-6
(2008)Doi:10.1055/s-0036-1588668
(2017)