Glycerin as a Renewable Feedstock for Epichlorohydrin Production. The GTE Process

Abstract

A significant improvement in a process to produce epichlorohydrin through the use of glycerin as renewable feedstock is presented. The glycerin to epichlorohydrin (GTE) process proceeds in two chemical steps. In the first step, glycerin is hydrochlorinated with hydrogen chloride gas at elevated temperature and pressure to a mixture of 1,3-DCH (1,3-dichlorohydrin, 1,3-dichloropropan-2-ol) and 2,3-DCH (2,3-dichlorohydrin, 2,3-dichloropropan-1-ol), using a carboxylic acid catalyst. In the second step, the mixture of dichlorohydrins is converted to epichlorohydrin with a base. This solventless process represents an economically and environmentally advantageous, atom-efficient process to an existing commodity chemical that can employ a renewable resource for its primary feedstock.

Novel Dehalogenase Mechanism for 2,3-Dichloro-1-Propanol Utilization in Pseudomonas putida Strain MC4

“…For routine measurements, the enzyme activity was measured by following the reduction of potassium ferricyanide, K 3 Fe(CN) 6 , at 420 nm in a 1-ml reaction mixture consisting of 50 mM Tris-SO 4 , pH 8.0, 5 mM DCP, and 1 mM potassium ferricyanide (extinction coefficient, 1 mM…”

“…The classical epichlorohydrin manufacturing process proceeds via hydrochlorination of allylchloride, which yields both 2,3-dichloro-1-propanol and 1,3-dichloro-2-propanol (30). Because of the increasing availability of glycerol as a side product from biodiesel synthesis, this classical process is being replaced with the use of glycerol as a renewable feedstock for epichlorohydrin manufacture, again via chlorination to the same dichloropropanols or via 1-chloro-2,3-propanediol (6). Epichlorohydrin itself as well as the production intermediates 2,3-dichloropropanol (DCP) and 1,3-dichloropropanol are mutagenic, genotoxic, and carcinogenic, and therefore their release and the possibility of human exposure are of significant concern (38).…”

The glycerol biorefinery: a purpose for Brazilian biodiesel production

“…In this process, glycerol reacts with HCl, yielding a mixture of 1,2-dichloro-3-propanol and 1,3-dichloro-2-propanol, which is treated with NaOH resulting in epichlorohydrin. The Dow Chemical Co. and Spolchemie (Czech Republic) have also developed processes to convert glycerin to epichlorohydrin [23,34,35,[43][44][45]. Figure 6 shows some products and their intermediates obtained by biotechnological pathway of glycerol (glycerin) conversion.…”

Changes in the composition of wastewater as a result of dehydrochlorination of 1,3-dichloropropan-2-ol under different process conditions

“…Because of increasing restrictions aimed at the protection of natural environment, more economical and environment friendly methods have been introduced. The latest method, competitive to the traditional technology based on chlorine and propylene, is the one based on glycerol 1 . The process of dichlorohydrins dehydrochlorination in glycerol method is signifi cantly different from the traditional chlorine process.…”