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Process for the production of polyols based on natural oils

A polyol and natural oil technology, which is applied in the reaction preparation of ester groups and hydroxyl groups, organic chemistry, etc., can solve the problems of undocumented preparation of modified castor oil and the like

Inactive Publication Date: 2007-06-06
BAYER MATERIALSCIENCE AG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the preparation of modified castor oil is not described

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] 604 g of soybean oil (Aldrich) were mixed with 76.4 g of formic acid under inert gas at room temperature and heated to 40°C with stirring. 157.2 g of hydrogen peroxide (30% in water) was added with stirring over 55 min while maintaining the temperature at 40-50°C. When the hydrogen peroxide addition was complete, the batch was heated to 70°C for 1 hour and then to 110°C for 8.5 hours. The ethylene oxide oxygen content was 0.01%. After removal of water and unreacted formic acid by distillation, the product was heated under vacuum at 110°C for 3 hours. Yield: 665g.

[0059] Intermediates obtained in this way have the following properties:

[0060] OH value: 171mg KOH / g

[0061] Acid value: 10.9mg KOH / g

[0062] Viscosity at 25°C: 1240mPas

[0063] 132 mg of DMC catalyst was added to 500 g of intermediate in a 10 liter laboratory autoclave. After the reaction mixture had been cured at 130°C with stirring at 450 rpm with nitrogen for ⏃ hours, the catalyst was activat...

Embodiment 2

[0069] To 600.2 g of soybean oil (Aldrich) was added 152 g of formic acid dropwise at room temperature under inert gas. The mixture was heated to 40°C with stirring. 312.5 g of hydrogen peroxide (30% in water) was added with stirring over 1.5 hours while maintaining the temperature at 40°C to 50°C. When the hydrogen peroxide addition was complete, the batch was heated to 70°C, and once the exothermic phase disappeared (temperature rose to 100°C), it was held at reflux temperature (104°C) for 4 hours. The ethylene oxide oxygen content was 0.01%. After removal of water and unreacted formic acid by distillation, the product was heated under vacuum at 110°C for 3 hours. Yield: 665g.

[0070] Intermediates obtained in this way have the following properties:

[0071] OH value: 226.3mg KOH / g

[0072] Acid value: 8.5mg KOH / g

[0073] Viscosity at 25°C: 21710mPas

[0074] 161 mg of DMC catalyst was added to 500 g of intermediate in a 10 liter laboratory autoclave. After the rea...

Embodiment 3

[0080] To 1005.6 g of soybean oil (Rübelmann) was added 127 g of formic acid under inert gas at room temperature. The mixture was heated to 40°C with stirring. 262.0 g of hydrogen peroxide (30% in water) was added with stirring over 1.25 hours while maintaining the temperature at 40 to 50°C. When the hydrogen peroxide addition was complete, the batch was heated to 70°C for 1 hour and then held at 106°C (reflux) for 7 hours. The ethylene oxide oxygen content was 0.05%. After removal of water and unreacted formic acid by distillation, the product was heated under vacuum at 110°C for 3 hours. Yield: 1028g.

[0081] Intermediates obtained in this way have the following properties:

[0082] OH value: 157.2mg KOH / g

[0083] Acid value: 7.25mg KOH / g

[0084] Viscosity at 25°C: 1170mPas

[0085] 268 mg of DMC catalyst was added to 971.2 g of intermediate in a 10 liter laboratory autoclave. After the reaction mixture had been cured at 130°C with stirring at 450 rpm with nitroge...

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Abstract

The present invention relates to a process for the production of polyols based on natural unsaturated oils. The process for the production of polyols based on natural oils comprises: a) oxidizing unsaturated triglycerides with peroxycarboxylic acids or hydrogen peroxide, catalyzed by carboxylic acids, at temperatures from about 20.degree.C to about 90.degree.C, wherein the molar ratio of hydrogen peroxide to the oxidizable double bond equivalents is from about 0.2 to about 1.5 and the molar ratio of catalytically active carboxylic acid to oxidizable double bond equivalents is from about 0.2 to about 1.1, b) converting the epoxide groups formed to alcohol groups in situ by raising the temperature to from about 90 to about 130.degree.C, if necessary after addition of further polyols, c) freeing products produced in a) and b) from volatile constituents in vacuo at temperatures of from about 60 to about 130.degree.C and d) alkoxylating the products obtained in a) to c) with alkylene oxides to form polyether polyols. The present invention provides a simple process allowing unmodified unsaturated fatty acid triglycerides to be converted into alkylene oxide adducts.

Description

technical field [0001] The present invention relates to a process for the production of polyols based on natural unsaturated oils. Background of the Invention [0002] Polyols based on stable raw materials such as fatty acid triglycerides, sugars, glycerol and dimerized fatty alcohols have been widely used as raw materials for the preparation of polyurethane materials. The application of such components will further increase in the future, as products from renewable sources are given positive evaluations in environmental reviews, and the availability of petrochemical-based raw materials will decline in the long term. Fatty acid triglycerides are mostly obtained from stable raw materials, and thus are a main component of an economical polyurethane raw material and the like. One disadvantage is the lack of fatty acid triglycerides that have introduced the active hydrogen atoms necessary to react with isocyanates. In this regard, the main exception is castor oil, while the ra...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/03C07C69/675C08H99/00
CPCC08G65/2609C08G65/2696C08G63/672C08G63/16C08G59/32C08G18/08C08G18/16C08G18/00C08G18/28
Inventor K·洛伦茨
Owner BAYER MATERIALSCIENCE AG
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