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Process for preparing an alkoxylated alcohol or phenol

A technology for alkoxylation of alcohols and alkylene oxides, which is applied in the fields of ether preparation, alkylene oxide preparation of ethers, organic chemistry, etc., and can solve the problem of no alkoxylation of secondary or tertiary alcohols

Inactive Publication Date: 2007-10-10
SHELL INT RES MAATSCHAPPIJ BV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are no examples of alkoxylated secondary or tertiary alcohols in this application

Method used

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  • Process for preparing an alkoxylated alcohol or phenol
  • Process for preparing an alkoxylated alcohol or phenol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0059] Example 1 - Ethoxylated secondary alcohol 2-undecanol

[0060]To a "Teflon" bottle equipped with a magnetic stir bar and immersed in a (water) cooling bath was added 2-undecanol (58 mmol, 10 g), boric acid (50 mg) and hydrogen fluoride (50 mg). Ethylene oxide was added in the gas phase at atmospheric pressure at such a flow that the temperature did not exceed 50°C. After about 3 hours, 15.8 g of ethylene oxide (358 mmol) were consumed, which corresponds to a degree of ethoxylation of 6.2 based on the amount introduced, and the product was then treated with about 50 mg of diethanolamine. The yield of ethoxylated 2-undecanol was 0.316 kg EO / g HF.

[0061] Measurements of average moles of ethylene oxide per mole of 2-undecanol, ethoxylate distribution and residual free alcohol were performed using high performance liquid chromatography (HPLC). The technique for these measurements involves the derivatization of ethoxylated alcohols with 4-nitrobenzoyl chloride. The produ...

Embodiment 2

[0063] Ethoxylated secondary alcohol 2-undecanol

[0064] The ethoxylation of 2-undecanol was carried out using the method of Example 1, except that the reaction temperature was maintained at 70°C. Measurements of average moles of ethylene oxide per mole of 2-undecanol, ethoxylate distribution and residual free alcohol were performed using the same technique as used in Example 1. The results are shown in Table 1 below.

Embodiment 3

[0066] Ethoxylated secondary alcohol 2-undecanol

[0067] The ethoxylation of 2-undecanol was carried out using the method of Example 1, except that the reaction temperature was maintained at 130°C. Measurements of average moles of ethylene oxide per mole of 2-undecanol, ethoxylate distribution and residual free alcohol were performed using the same technique as used in Example 1. The results are shown in Table 1 below.

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Abstract

Process for preparing an alkoxylated alcohol comprising reacting a starting monohydroxy alcohol selected from secondary alcohols, tertiary alcohols and mixtures thereof with an alkylene oxide in the presence of hydrogen fluoride and a boron-containing compound comprising at least one B-O bond. The alcohol may also be a primary monohydroxy alcohol when the boron containing compound is boric acid or boric acid anhydride or a mixture thereof, or may be a primary mono hydroxy alcohol, except a C14 / C15 alcohol when reacted with ethylene oxide in the presence of HF and trimethyl borate. A phenol may be alkoxylated in the same way instead of the mono-hydroxyalcohol.

Description

technical field [0001] The present invention relates to a process for the preparation of alkoxylated alcohols or phenols. Background technique [0002] Preparation, for example, as nonionic surfactants, wetting and emulsifying agents, by the addition reaction (alkoxylation) of alkylene oxides (epoxides) with organic compounds having one or more active hydrogen atoms , solvents and chemical intermediates in a variety of products. For example, particular mention may be made of alkanol ethoxylates and alkyl-substituted phenol ethoxylates prepared by reaction of ethylene oxide with aliphatic alcohols or substituted phenols having 6 to 30 carbon atoms. Such ethoxylates and to a lesser extent the corresponding propoxylates and compounds containing mixed oxyethylene and oxypropylene groups are widely used as nonionic detergent components in industrial cleaning formulations for industrial and domestic use. [0003] The following formula sets forth a schematic diagram of the prepar...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C41/03C07C43/11C08G65/28
CPCC08G65/269C08G65/2654C07C41/03C08G65/2684C07C43/11C07C43/13C08G65/26
Inventor J·H·H·缪尔斯W·C·沃赫夫-范维耶克A·范佐恩
Owner SHELL INT RES MAATSCHAPPIJ BV
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