Method for preparing p-toluenesulfonyl isocyanate with carbonyl fluoride

A technology of toluenesulfonyl isocyanate and carbonyl fluoride method, applied in the preparation of sulfonic acid amide, organic chemistry, etc., can solve problems such as side reactions, production risks, and difficulty in product separation and purification, and achieve high yield and reduce pollution.

Inactive Publication Date: 2016-08-10
BEIJING YUJI SCI & TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In addition, the solubility of phosgene in the solvent is limited, and it is difficult to measure in use. It often requires a large amount of phosgene and prolonging the reaction time to ensure that the reaction is fully carried out. This not only easily causes side reactions, increases the consumption and cost of phosgene, but also It brings difficul...

Method used

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  • Method for preparing p-toluenesulfonyl isocyanate with carbonyl fluoride
  • Method for preparing p-toluenesulfonyl isocyanate with carbonyl fluoride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Add 25.6g (0.15mol) of p-toluenesulfonamide and 50ml of toluene into a 150ml stainless steel reaction kettle with stirring, fill in 28.0g of carbonyl fluoride, close the system, and react at 80°C for 3 hours, recover excess carbonyl after the reaction is completed Fluorine, then increase the reaction temperature to 140°C under normal pressure, react for 2 hours, and distill off the solvent toluene at the same time, the reaction is completed in 2 hours, and the crude product p-toluenesulfonyl isocyanate is 26.9g, the purity is 94.2%, and the reaction yield is 85.9%.

Embodiment 2

[0035] Add 25.6g (0.15mol) of p-toluenesulfonamide and 75ml of toluene into a 150ml stainless steel reactor with stirring, fill in 40.8g of carbonyl fluoride, close the system, react at 80°C for 3 hours, recover excess carbonyl after the reaction is completed Fluorine, then raise the reaction temperature to 140°C under normal pressure, react for 2 hours, and distill off the solvent toluene at the same time, finally get 28.0 g of p-toluenesulfonyl isocyanate as a crude product, with a purity of 95.6% and a reaction yield of 90.7%.

Embodiment 3

[0037] Add 25.6g (0.15mol) p-toluenesulfonamide and 50ml xylene into a 150ml stainless steel reactor with stirring, fill in 29.9g carbonyl fluoride, close the system, react at 80°C for 3 hours, and recover excess carbon after the reaction is completed Acyl fluoride, then increase the reaction temperature to 140°C under normal pressure, react for 2 hours, and distill off the solvent xylene at the same time to finally obtain 29.6 g of p-toluenesulfonyl isocyanate as a crude product with a purity of 95.0% and a reaction yield of 95.3%.

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Abstract

The invention discloses a method for preparing p-toluenesulfonyl isocyanate with carbonyl fluoride. The method includes the following steps that firstly, under pressure, toluene sulfonamide and carbonyl fluoride react in a liquid phase to generate a fluorine-containing intermediate; secondly, at normal pressure, the one-molecule HF production target product p-toluenesulfonyl isocyanate is removed from the fluorine-containing intermediate at high temperature. In the reaction process, catalyst catalysis is not needed, excessive carbonyl fluoride and solvents used in reaction can be recycled and reused, and HF generated due to reaction can be sold as commodities after being absorbed. The method is mainly used for preparation of p-toluenesulfonyl isocyanate.

Description

technical field [0001] The invention belongs to the technical field of organic compounds, and in particular relates to a synthesis method for preparing p-toluenesulfonyl isocyanate (PTSI) by directly reacting p-toluenesulfonamide (PTSA) with carbonyl fluoride instead of phosgene. Background technique [0002] p-Toluenesulfonyl isocyanate is a low viscosity, highly reactive monoisocyanate. It can react with water to generate carbon dioxide and p-toluenesulfonamide, which generally does not react with alkyl isocyanate or aryl isocyanate and can be dissolved in common solvents, so p-toluenesulfonyl isocyanate can be used in one-component or two-component The water remover in the component polyurethane paint can be added in any process of polyurethane paint production before packaging, such as dispersion, grinding, and paint mixing. In addition, p-toluenesulfonyl isocyanate has a variety of reactivity, and can be used as a desiccant for organic solvents, photoactivation and dim...

Claims

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Application Information

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IPC IPC(8): C07C303/36C07C311/53C07C311/65
CPCC07C303/36C07C311/53C07C311/65
Inventor 周晓猛李喆庆飞要杨会娥赵升权恒道
Owner BEIJING YUJI SCI & TECH
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