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Method of making alkoxylates

A compound and a technology for producing alkanes, applied in sustainable manufacturing/processing, ether preparation, organic chemistry, etc., can solve problems such as volatility instability, concentration, and non-optimal product properties of ethylene oxide

Inactive Publication Date: 2008-05-07
GRT INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Some disadvantages of this method include: (1) cost of ethylene oxide, (2) volatility and instability of ethylene oxide, and (3) cost of alcohol
Existing methods can also result in a less concentrated distribution of ethoxylation degrees than desired
In addition to contributing to non-optimal product properties, the relative volatility and lower ethoxylates of the unreacted alcohol also negatively impact the spray drying operation used to produce the product powder

Method used

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  • Method of making alkoxylates
  • Method of making alkoxylates
  • Method of making alkoxylates

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0082] An approximately 3 mL stainless steel batch reactor was filled with 0.2549 grams of electronic grade magnesia (eMgO) and 0.2543 grams of a solution of 75 wt% 2-bromododecane and 25 wt% octadecane (as internal standard). Stir with a stainless steel spatula to mix the solids and liquids, then add 0.3065 grams of ethylene glycol (EG). The reactor was sealed and agitated with a vibrating shaker for 5 minutes, then placed in a preheated oven at 225°C for 6 hours. Once cooled, the organics were extracted with ethanol and analyzed by gas chromatography and mass spectrometry to characterize and quantify the product and starting material. Analysis showed that 49% of the 2-bromododecane was converted to product. The product consisted of 56% olefins, 3% alcohols, 40% monoethoxylates and 1% ketones.

Embodiment 2

[0084] An approximately 3 mL stainless steel batch reactor was filled with 0.2531 g of copper(II) oxide (CuO) and 0.2500 g of a solution of 75 wt% 2-bromododecane and 25 wt% octadecane (as internal standard). Stir with a stainless steel spatula to mix the solids and liquids, then add 0.0976 grams of EG. The reactor was sealed and agitated with a vibrating shaker for 5 minutes, then placed in a preheated oven at 225°C for 6 hours. Once cooled, the organics were extracted with ethanol and analyzed by gas chromatography and mass spectrometry to characterize and quantify the product and starting material. Analysis showed 97% conversion of 2-bromododecane to product. The product consists of 58% olefins, 9% alcohols, 32% monoethoxylates and 1% ketones.

Embodiment 3

[0086] An approximately 3 mL stainless steel batch reactor was filled with 0.2501 g of copper(II) oxide (CuO) and 0.2538 g of a solution of 75 wt% 2-bromododecane and 25 wt% octadecane (as internal standard). Stir with a stainless steel spatula to mix the solids and liquids, then add 0.1002 grams of EG. The reactor was sealed and agitated with a vibrating shaker for 5 minutes, then placed in a preheated oven at 225°C for 3 hours. Once cooled, the organics were extracted with ethanol and analyzed by gas chromatography and mass spectrometry to characterize and quantify the product and starting material. Analysis showed that 42% of the 2-bromododecane was converted to product. The product consisted of 31% olefins, 5% alcohols, 63% monoethoxylates and 1% ketones.

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Abstract

Ethoxylates and other alkoxylates are made in an efficient manner by reacting an organic bromide with a diol in the presence of a metal oxide. An integrated process of bromide formation, alkoxylate synthesis, metal oxide regeneration, and bromine recycling is also provided.

Description

field of invention [0001] This invention relates generally to methods of making alkoxylates (hydroxylated ethers), and more particularly to the synthesis of such compounds by reacting brominated hydrocarbons with diols in the presence of metal oxides or other metal-oxygen catalyzed reactants. An integrated process using hydrocarbon feedstock and metal oxide and bromine regeneration is also disclosed. Background of the invention [0002] Alkoxylates (hydroxylated ethers) and especially ethoxylates (eg monoalkyl or aryl ethers of ethylene glycol or ethylene glycol oligomers) are important industrial compounds either directly as alkane Oxygenated compounds are used either as surfactants, detergents and other applications after sulphation to sulfate esters. Sulfated alkoxylates are preferred over (non-ethoxylated) alcohol sulfates due to reduced sensitivity to water hardness, less user irritation and higher solubility. [0003] Commercially important ethoxylates are generally ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C41/16C07C43/13
CPCC07C41/16C07C43/135C07C43/13Y02P20/10C07C43/11
Inventor M·J·威斯Z·J·A·科蒙
Owner GRT INC
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