Etherification Process Using Excess Alkene for Lubricant Base Stocks

Solution Overview

Problem

Existing processes for preparing ethers as lubricant base stocks often generate corrosive intermediates and face challenges with low yield and energy-intensive distillation due to the use of stoichiometric or excess alcohol, making it difficult to achieve desirable viscosity profiles and low volatility.

Innovation Solution

A process involving the reaction of an alcohol with an alkene in the presence of an acidic ion-exchange resin or aluminosilicate catalyst, where the alkene is in molar excess, to produce ethers with improved yield and reduced residual alcohol, facilitating easier isolation and incorporation into lubricant compositions.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If excess alcohol is used to push conversion closer to 100%, then ether yield is improved, but energy-intensive distillation is required to remove residual alcohol

Engineering Contradiction:

Improveether yieldVSAvoiddistillation energy

Core Design Contradiction:

ProductivityVSUse of energy by stationary object

Solution Approach 1:

The patent inverts the conventional approach by using excess alkene instead of excess alcohol. This reversal eliminates the need for energy-intensive distillation to remove residual alcohol, as the alkene can be easily removed by decantation or filtration after the etherification reaction.

Inventive Principle:

Principle #13The other way round (Inversion)

Solution Approach 2:

The patent changes the molar ratio parameter from excess alcohol to excess alkene. This parameter change fundamentally alters the separation requirements, allowing for simpler and less energy-intensive product isolation while maintaining high ether conversion yields.

Inventive Principle:

Principle #35Parameter changes

2Ease of manufacture

If stoichiometric or excess alcohol is used, then etherification proceeds, but residual alcohol remains requiring energy-intensive distillation

Engineering Contradiction:

Improveetherification processVSAvoiddistillation energy

Core Design Contradiction:

Ease of manufactureVSUse of energy by stationary object

Solution Approach 1:

The patent inverts the conventional approach by using excess alkene instead of excess alcohol. This reversal eliminates the need for energy-intensive distillation to remove residual alcohol, as the alkene can be easily removed by decantation or filtration after the etherification reaction.

Inventive Principle:

Principle #13The other way round (Inversion)

3Productivity

If alcohol is used in excess to improve conversion, then ether yield increases, but isolation becomes more difficult due to similar boiling points

Engineering Contradiction:

Improveether yieldVSAvoidisolation difficulty

Core Design Contradiction:

ProductivityVSEase of manufacture

Solution Approach 1:

The patent inverts the conventional approach by using excess alkene instead of excess alcohol. This reversal eliminates the need for energy-intensive distillation to remove residual alcohol, as the alkene can be easily removed by decantation or filtration after the etherification reaction.

Inventive Principle:

Principle #13The other way round (Inversion)

4Productivity

If known etherification processes are used, then ethers are produced, but corrosive halogenated or sulfonate ester intermediates are generated

Engineering Contradiction:

Improveether productionVSAvoidcorrosive intermediates

Core Design Contradiction:

ProductivityVSObject-generated harmful factors

Solution Approach 1:

The patent eliminates the use of corrosive halogenated or sulfonate ester intermediates by employing a direct etherification process between alcohol and alkene. This approach converts a harmful chemical pathway into a benign one, producing only water as a byproduct and avoiding corrosive intermediate compounds entirely.

Inventive Principle:

Principle #22Blessing in disguise (Convert harm into benefit)

Solution Approach 2:

The patent changes the reaction pathway by using acid catalysis with excess alkene instead of conventional methods involving halogenated or sulfonate ester intermediates. This parameter change in the reaction mechanism eliminates the formation of harmful corrosive intermediates while maintaining high ether production efficiency.

Inventive Principle:

Principle #35Parameter changes

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 approach enhances the conversion of alcohol to ether, reduces residual alcohol, and allows for the production of ethers with improved viscosity profiles and low volatility, suitable for use as lubricant base stocks, while avoiding the formation of corrosive intermediates and energy-intensive distillation.

Implementation Method 1

the reaction of an alcohol and alkene in the presence of an acidic ion-exchange resin etherification catalyst and/or an acidic aluminosilicate etherification catalyst

Methodology Applied

Scientific EffectCatalysis: Catalysis

Data Source

PatentEP3583195B1Etherification process, process for preparing a lubricant composition and process for lubricating a surface

Publication Date: 2023.12.20 BRITISH PETROLEUM CO PLC

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AI summary

The present invention relates to an etherification process for preparing ethers, particularly unsymmetrical ethers, suitable for use as base stocks for lubricant compositions. In one aspect, the present invention provides a process for preparing an ether for use as a lubricating base stock, said process comprising contacting an alcohol with an alkene in the presence of an acidic ion-exchange resin etherification catalyst and/or an aluminosilicate etherification catalyst, wherein: i) the alcohol comprises a C8+ aliphatic hydrocarbyl group; ii) the alkene comprises a tertiary olefinic carbon atom; and iii) the alkene is present in molar excess relative to the alcohol.