Method for preparation of thiocarbonates

A monothiocarbonate, carbocyclic technology, applied in organic chemistry and other directions, can solve problems such as performance problems, low availability of thiocarbonates, and low availability

Pending Publication Date: 2021-09-07
BASF SE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Many of these approaches involve the use of raw materials with low availability, high cost, or questionable performance
In addition, the resulting yields and selectivities, especially the selectivity of structural isomers, are not yet sufficient for industrial-scale production
Consequently, the availability of thiocarbonates in industrial quantities is low, even though thiocarbonates are highly interesting as intermediates in chemical syntheses

Method used

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  • Method for preparation of thiocarbonates
  • Method for preparation of thiocarbonates
  • Method for preparation of thiocarbonates

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0179] GC analysis: Agilent Technologies 7890 A Network GC System

[0180] Column: DB1 (Agilent) 30m, Film thickness 1μm;

[0181] Carrier gas He; flow rate 1.0mL / min; split ratio: 50:1

[0182] T program: 50-300°C, heating rate 10°C / min; 30min isothermal

[0183] Temperature (injection system) 250°C

[0184] Preparation of 2-chloroethyl chloroformate, process step b)

[0185]

[0186] The synthesis was performed in a 1 L stirred tank reactor equipped with two condensers (-30°C and -78°C (dry ice)), phosgene dip tube, thermometer and dropping funnel. Phosgene (46.0 g, 0.5 mol) was introduced into the empty reactor at a temperature of 10°C until phosgene reflux was observed. Then 2-chloroethanol (161 g, 2.00 mol) was added via dropping funnel over 2 hours. The internal temperature recorded during this time can vary within 10-14 °C. Additional phosgene (404 g, 4.0 mol) was added simultaneously during the addition of 2-chloroethanol to ensure phosgene reflux throughout...

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Abstract

Provided is a process for the preparation of a compound with at least one five-membered cyclic monothiocarbonate group, wherein a) a compound C1 with at least one halohydrin group is used as starting material, b) the compound C1 is reacted with phosgene or an alkyl chloroformate to give an adduct C2, and c) the adduct C2 is reacted with a compound comprising anionic sulfur to obtain the compound with at least one five-membered cyclic monothiocarbonate group.

Description

[0001] The object of the invention is a process for the preparation of compounds having at least one 5-membered cyclic monothiocarbonate group, wherein [0002] a) using a compound C1 having at least one halohydrin group as starting material, [0003] b) reacting compound C1 with phosgene or alkyl chloroformate to give adduct C2, and [0004] c) reacting the adduct C2 with a compound comprising anionic sulfur to obtain the compound having at least one 5-membered cyclic monothiocarbonate group. [0005] Background of the invention [0006] Cyclic monothiocarbonates are useful starting materials for the synthesis of compounds. However, to date, cyclic monothiocarbonates have not been used in any industrial process on a large scale. [0007] Different methods for the synthesis of cyclic monothiocarbonates are described in the prior art. [0008] According to the method disclosed in US 3349100, alkylene monothiocarbonates are obtained by reacting epoxides with carbonyl sulphide....

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D327/04
CPCC07D327/04
Inventor P·鲁道夫I·蒂埃尔T·M·武姆J·H·特莱斯J-D·阿恩特
Owner BASF SE
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