Branched C10 Mercaptan Composition and Purification

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Solution Overview

Problem

The high cost and complexity of purifying individual mercaptans due to numerous purification steps required, while many applications can utilize mercaptan mixtures, necessitate the development of cost-effective mercaptan compositions and methods for preparing such mixtures.

Innovation Solution

A composition comprising at least 25 wt.% branched C10 mercaptans and 5 wt.% branched C20 sulfides, produced by reacting hydrogen sulfide with branched C10 monoolefins in the presence of an initiating agent, such as UV radiation, to yield a crude composition with 50 wt.% or more branched C10 mercaptans and 10 wt.% or more branched C20 sulfides, which can be further processed to remove impurities and achieve specific weight percentages of mercaptans and sulfides.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Manufacturing precision

If individual mercaptans are purified through numerous purification steps, then purity of individual mercaptan compounds is improved, but production cost and process complexity increase

Engineering Contradiction:
Improvepurity of individual mercaptan compoundsVSAvoidprocess complexity
Core Design Contradiction:
Manufacturing precisionVSDevice complexity

Solution Approach 1:

The patent segments the purification process by separating mercaptans from sulfides through distillation based on boiling point differences, then further separating individual mercaptan isomers through fractional distillation. This segmentation approach allows systematic purification without requiring complex simultaneous separation methods.

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The patent extracts sulfide impurities from the mercaptan mixture through selective reaction with base, forming water-soluble sulfide salts that can be removed by aqueous washing. This extraction step eliminates the need for complex chromatographic separation of sulfides from mercaptans.

Inventive Principle:
Principle #2Taking out (Extraction)

2Manufacturing precision

If individual mercaptans are purified through numerous purification steps, then purity of individual mercaptan compounds is improved, but production cost increases

Engineering Contradiction:
Improvepurity of individual mercaptan compoundsVSAvoidproduction cost
Core Design Contradiction:
Manufacturing precisionVSEase of manufacture

Solution Approach 1:

The patent combines multiple purification operations into an integrated process flow: distillation to separate mercaptans from sulfides, followed by base washing to remove remaining sulfides, and fractional distillation to separate individual mercaptan isomers. This combined approach reduces overall production cost compared to using multiple independent purification methods.

Inventive Principle:
Principle #5Merging (Combining)

Solution Approach 2:

The patent utilizes boiling point parameter differences to separate mercaptans from sulfides and to separate individual mercaptan isomers. By controlling distillation temperature and pressure parameters, the process achieves high purity separation without requiring expensive advanced separation technologies.

Inventive Principle:
Principle #35Parameter changes

3Ease of manufacture

If mercaptan mixtures are produced directly from reaction products, then production cost and process simplicity are improved, but purity and controlled composition of the mixture may be compromised

Engineering Contradiction:
Improveproduction cost and process simplicityVSAvoidpurity and controlled composition
Core Design Contradiction:
Ease of manufactureVSManufacturing precision

Solution Approach 1:

The patent performs preliminary distillation to separate the crude reaction products into fractions containing mercaptans, sulfides, and unreacted starting materials. This preliminary action creates a cleaner feedstock for subsequent purification steps, improving both cost-effectiveness and final purity.

Inventive Principle:
Principle #10Preliminary action

Solution Approach 2:

The patent employs analytical methods such as gas chromatography to monitor the composition of the mercaptan mixture at various stages of purification. This feedback allows adjustment of process parameters to achieve the desired composition and purity, ensuring product specifications are met while maintaining cost-effectiveness.

Inventive Principle:
Principle #23Feedback

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 reduces production costs and simplifies the process of obtaining mercaptan compositions suitable for various applications by achieving high yields of branched C10 mercaptans and C20 sulfides with controlled impurity levels, enhancing the efficiency and cost-effectiveness of mercaptan production.

Implementation Method 1

reacting hydrogen sulfide with branched C10 monoolefins in the presence of an initiating agent, such as UV radiation

Methodology Applied
Scientific EffectUV radiation initiation: Photopolymerisation

Data Source

PatentEP3397615B1Mixed decyl mercaptans compositions and methods of making same
Publication Date: 2021.08.18 CHEVRON PHILLIPS CHEMICAL COMPANY LP
  • EP3397615B1 patent drawingFigure 1
  • EP3397615B1 patent drawingFigure 2
  • EP3397615B1 patent drawingFigure 3

AI summary

Compositions comprising branched C10 mercaptans selected from the group consisting of 5-methyl-1-mercapto-nonane, 3-propyl-1-mercapto-heptane, 4-ethyl-1-mercapto-octane, 2-butyl-1-mercapto-hexane, 5-methyl-2-mercapto-nonane, 3-propyl-2-mercapto-heptane, 4-ethyl-2-mercapto-octane, 5-methyl-5-mercapto-nonane, and combinations thereof.