Boron Ester Acidolysis for Sulfate Ester Synthesis
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Solution Overview
Problem
Current methods for producing sulfate or sulfonate esters are limited by low yields, generation of isomeric by-products, and the use of toxic chemicals like sulfur trioxide, which complicates large-scale, safe, and cost-effective production of anionic surface active agents.
Innovation Solution
A method involving the acidolysis of boron esters with sulfuric acid or sulfonic acid in the presence of solvents like dichloroethane, or without solvents, to produce monoalkyl or dialkyl sulfate esters with high purity, avoiding the use of toxic chemicals and isomeric by-products.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Productivity
If tertiary amine-sulfur trioxide complexes are used for sulfation, then sulfation reaction can proceed, but low yields and isomeric by-products are generated
Solution Approach 1:
The patent introduces boron esters as intermediary compounds in the sulfation process. Instead of directly reacting alcohols with sulfur trioxide complexes, the method first converts alcohols to boron esters, which then react with sulfur trioxide to produce sulfate esters. This intermediary step prevents direct isomerization of the alcohol substrate, thereby eliminating isomeric by-products while maintaining high reaction efficiency and yield.
2Ease of manufacture
If sulfur trioxide and its complexes are used, then sulfation reaction can be performed, but special precautions are required due to corrosiveness and humectant properties
Solution Approach 1:
Boron esters serve as protective intermediaries that mediate between the alcohol substrate and the hazardous sulfur trioxide. This intermediary approach allows the reaction to proceed under milder, safer conditions without direct contact between the corrosive sulfur trioxide and the alcohol, eliminating the need for special precautions while maintaining reaction effectiveness.
Solution Approach 2:
The boron esters are used in stoichiometric amounts and can be easily removed from the final product through simple filtration or washing steps. This disposable intermediary approach makes the process safer and more economical, as the boron-containing by-products are non-hazardous and can be disposed of without special precautions.
3Productivity
If conventional sulfation methods are used, then sulfate esters can be produced, but isolation and purification of the product is difficult
Solution Approach 1:
The boron ester intermediary enables easy separation of the sulfate ester product from the reaction mixture. The boron-containing by-products (boric acid or boron esters) are insoluble or easily removable, allowing the sulfate ester to be isolated through simple filtration or extraction steps, greatly simplifying the purification process compared to conventional methods.
Applied Scientific Principles
This section explains which scientific principles are used to turn an abstract innovation direction into a practical engineering solution.
Function Achieved in This Case
This method enables the safe, cheap, and large-scale production of alkali metal salts of monoalkyl sulfates with high yields and purity, eliminating isomeric by-products and reducing the reliance on hazardous substances.
Implementation Method 1
the acidolysis of boron esters with sulfuric acid or sulfonic acid in the presence of solvents like dichloroethane, or without solvents, to produce monoalkyl or dialkyl sulfate esters
Data Source
Figure 1
AI summary
The present invention relates to method for the production of sulfate or sulfonate esters essentially comprising the steps of adding sulfuric acid or sulfonic acid to boron acid in a medium with or without solvent (121), stirring the prepared mixture 8122), removing the precipitated boric acid (123), removing the solvent in case the solvent is used (124), producing dialkyl sulfate esters, mono alkyl sulfate esters and sulfonate esters of alkali metal salts (125), and based on the acidolysis of boron esters obtained from alcohol and boric acid with sulfuric acid or sulfonic acid.