Method for synthesizing 1,2-orthodiol through immobilized type heteropolyacid phase-transfer catalytic oxidation

Abstract

The invention discloses a method for synthesizing 1,2-orthodiol through immobilized type heteropolyacid phase-transfer catalytic oxidation. The method comprises the following steps: 1, sequentially adding an acid, terminal alkene, hydrogen peroxide and a polystyrene resin immobilized type heteropolyacid phase-transfer catalyst into a reactor, stirring, reacting a mixture liquid at 40-80 DEG C, after the reaction is accomplished, filtering and recycling the catalyst so as to obtain an epoxy mixture liquid; 2, dropwisely adding an alkali solution into the epoxy mixture liquid so as to adjust the pH value to be 10-12, keeping the temperature of 30-70 DEG C to react so as to obtain a target product mixture liquid; 3, after the reaction is accomplished, extracting the target product mixture liquid by using an ester solution, washing, drying, and distilling under reduced pressure so as to obtain 1,2-orthodiol. The 1,2-orthodiol is widely applied to production of polyesters and surfactants and can also be used as a raw material for pharmacy.

Description

technical field [0001] The invention belongs to the field of fine organic synthesis, and relates to the synthesis of 1,2-o-diol, in particular to a method for synthesizing 1,2-o-diol by using a solid-supported heteropolyacid phase transfer catalyst to catalyze the oxidation reaction of terminal alkenes . Background technique [0002] 1,2-O-diol is an important chemical raw material, which is often used to produce polyester and surfactant, and can also be used as a raw material for pharmaceuticals. Straight-chain 1,2-o-diols, especially C2-C4-o-diols, are mostly produced by hydration of epoxides under high temperature and pressure or under alkaline or acidic conditions. The existing 1,2-o-diols are synthesized The disadvantage of the method is that the production cost is relatively high and the environmental pollution is relatively serious. [0003] Members of James P. Morken et al. "J. AM. CHEM. SOC., 2009,131: 13210-13211" research group used neopentyl glycol bis-...

AI Technical Summary

Problems solved by technology

Straight-chain 1,2-o-diols, especially C2-C4-o-diols, are mostly produced by hydration of epoxides under high temperature and pressure or under alkaline or acidic conditions. The existing 1,2-o-diols are synthesized The disadvantage of the method is that the production cost is relatively high and the environmental pollution is relatively serious.

[0003] Members of James P. Morken et al. "J. AM. CHEM. SOC., 2009,131: 13210-13211" research group used neopentyl glycol bis-boronate to catalyze terminal alkenes to synthesize 1,2-o-diols. This research process is very important for Industrial production is impractical, and the catalyst is too expensive; Li Linqing et al. "Applied Chemistry, 2011, 28 (11): 1256-1262" studied the catalytic epoxidation of metal tetracarboxylic phthalocyanines to olefins, and synthesized four kinds of metal Tetracarboxylic acid phthalocyanine metal, using it as a catalyst, has carried out the research on the epoxidation of olefins with molecular oxygen as the oxygen source. In this research, the conversion rate and selectivity of 1-octene are relatively low; Venturello et al. "J Org Chem, 1988, 53: 1553-1557; J Org Chem, 1983, 48: 3831-3833 "use hydrogen peroxide as the oxidant, the by-product of this reaction is only water, the Na they used 2 WO 4 -H 3 PO 4 - Quaternary ammonium salt is used as a catalyst, and 1,2-dichloroethane must be added to form two phases with water during the reaction. Hydrogen peroxide is used as an oxygen source, and the oxidizing property is not strong enough. The yield is only 53%, which is relatively low

In the patent "CN200610050149.6" applied by Liu Min, no catalyst is used. Because terminal alkenes like 1-octene are difficult to react without a catalyst, the yield must be very low and cannot be used in industrial production.

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