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Method for preparing plant oil-based isocyanate

An oil-based isocyanate and vegetable oil-based technology, which is applied in the field of preparation of vegetable oil-based isocyanates, can solve the problems of decreased application value, low reactivity, high price and the like, and achieves a controllable number of NCOs, high reaction yield, and improved reactivity. Effect

Active Publication Date: 2014-04-23
秦皇岛高鹏泡沫塑料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] According to reports, figure 1 , in methods (A) and (B), AgNCO and NH 4 The reactivity of SCN and Br is low, only 50%~70% participate in the reaction; in method (C), the carbon-carbon double bond and AgNCO·I 2 The number of reactions can reach up to 3.1, and the number of isocyanate groups cannot be well designed and controlled, and the three reactions all use expensive metallic silver compounds as raw materials, resulting in a sharp decline in their application value; prepared by these three methods The -NCO (-NCS) is directly connected to the fatty acid chain of vegetable oil without a spacer, and is easily covered and entangled by the long chain of fatty acid to reduce its reactivity as a monomer for polyurethane preparation

Method used

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  • Method for preparing plant oil-based isocyanate
  • Method for preparing plant oil-based isocyanate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] (1) Add 15.00g of rapeseed oil, 11.20g of 3-mercaptopropionic acid, 0.393g of 2, 2'-diethoxyacetophenone and 30ml of dichloromethane into the reaction flask, and use 1.8mw / cm 2 UV light was irradiated for 8 hours, excess 3-mercaptopropionic acid was removed by washing with deionized water, the organic layer was dried by anhydrous magnesium sulfate, and dichloromethane was removed by rotary evaporation to obtain 16.43 g of rapeseed oil-based carboxylic acid.

[0019] (2) Add 8.00g of rapeseed oil-based carboxylic acid, 6 drops of N,N-dimethylformamide, 20ml of dichloromethane, and 20.00g of thionyl chloride into the reaction flask, and stir at 45°C for 5 hours. Rotary evaporation removed dichloromethane and thionyl chloride to obtain rapeseed oilyl chloride.

[0020] (3) Add 1.79g of sodium azide and 19.45g of deionized water into the reaction flask, place in an ice bath, add dropwise the tetrahydrofuran solution dissolved in rapeseed oilyl chloride under stirring withi...

Embodiment 2

[0026] (1) Add 15.00g of corn oil, 13.32g of 3-mercaptopropionic acid, 0.798g of 2, 2'-dimethylbenzil ketal and 30ml of dichloromethane into the reaction flask, and use 1.8mw / cm 2 UV light was irradiated for 8 hours, excess 3-mercaptopropionic acid was removed by washing with deionized water, the organic layer was dried by anhydrous magnesium sulfate, and dichloromethane was removed by rotary evaporation to obtain 16.21 g of corn oilyl carboxylic acid.

[0027] (2) Add 8.00g of corn oil-based carboxylic acid, 6 drops of N,N-dimethylformamide, 20ml of dichloromethane, and 17.80g of thionyl chloride into the reaction flask, and stir at a temperature of 50°C After 5 hours, dichloromethane and thionyl chloride were removed by rotary evaporation to obtain corn oleyl chloride.

[0028] (3) Add 1.61g of sodium azide and 17.58g of deionized water into the reaction flask, place in an ice bath, add the tetrahydrofuran solution dissolved in corn oleyl chloride dropwise under stirring wi...

Embodiment 3

[0033] (1) Add 15.00g of soybean oil, 13.32g of 3-mercaptopropionic acid, 0.798g of 2-hydroxybenzophenone and 30ml of dichloromethane into the reaction flask, and use 1.8mw / cm 2 UV light was irradiated for 8 hours, excess 3-mercaptopropionic acid was removed by washing with deionized water, the organic layer was dried by anhydrous magnesium sulfate, and dichloromethane was removed by rotary evaporation to obtain 15.92 g of soybean oleyl carboxylic acid.

[0034] (2) Add 8.00g of soybean oil-based carboxylic acid, 6 drops of N,N-dimethylformamide, 20ml of dichloromethane, and 17.80g of thionyl chloride into the reaction flask, and stir at a temperature of 50°C After 5 hours, dichloromethane and thionyl chloride were removed by rotary evaporation to obtain soybean oilyl chloride.

[0035] (3) Add 1.70g of sodium azide and 18.48g of deionized water into the reaction flask, put it in an ice bath, add the tetrahydrofuran solution dissolved in soybean oleyl chloride dropwise under s...

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Abstract

The invention relates to a medical field, and discloses a method for co-preparing plant oil-based isocyanate by a mercapto-alkene click reaction and a Curtius rearrangement reaction, comprising: (1) preparation of plant oil-based polyprotic acid, (2) preparation of plant oil-based acyl chloride, and (3) preparation of plant oil-based acid azide and isocyanate, to obtain a target product. Aiming at disadvantages of the current plant oil-based isocyanate preparation technology, the invention provides a preparation method of plant oil-based isocyanate with simpleness, easy operation, controllable NCO number and high reaction yield.

Description

technical field [0001] The invention belongs to the field of chemical industry, and in particular relates to a preparation method of vegetable oil-based isocyanate. Background technique [0002] Due to its excellent wear resistance, excellent chemical resistance, high decorative properties and wide temperature applicability, polyurethane resin has become a research hotspot in the coatings and adhesives industry in recent years. At present, the raw materials for the production of polyurethane are mainly petrochemical products. With the depletion of petroleum resources, the research on the preparation of environmentally friendly polyurethane from renewable resources has become the focus of the coating industry. Vegetable oil has become a very important renewable resource because of its low price, wide range of sources and chemical modification. Isocyanate is an important part of polyurethane. There are few studies on the preparation of isocyanate from renewable resources beca...

Claims

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Application Information

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IPC IPC(8): C07C319/20C07C323/54
Inventor 付长清申亮郑子童
Owner 秦皇岛高鹏泡沫塑料有限公司
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