Renewable Alkylbenzene Production from Triglycerides

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Solution Overview

Problem

Current processes for producing linear alkylbenzenes for detergents rely on fossil fuels, which are unsustainable and environmentally detrimental, and do not effectively utilize renewable sources like vegetable and animal oils, which have desirable n-paraffin ranges.

Innovation Solution

A process involving the deoxygenation of triglycerides from natural oils to produce high-linearity C9 to C14 paraffins, followed by selective cracking and dehydrogenation to form alkylbenzenes, using catalysts like Ru/ZrO2 to maximize yield and minimize branched isomers, and then alkylation with benzene to produce linear alkylbenzenes.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Ease of manufacture

If alkylbenzenes are produced from kerosene refined from crude oil, then the production process is established and scalable, but the process relies on fossil fuels which are unsustainable and environmentally detrimental

Engineering Contradiction:
ImprovemanufacturabilityVSAvoidenvironmental impact
Core Design Contradiction:
Ease of manufactureVSObject-affected harmful factors

Solution Approach 1:

The patent changes the fundamental feedstock parameter from fossil fuel-based kerosene to renewable triglyceride-based feedstocks. This parameter change transforms the environmental impact while maintaining the ability to produce alkylbenzenes through modified process conditions and catalysts that work with the renewable feedstock composition

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent introduces an intermediary conversion process that transforms triglycerides into alkylbenzenes through multiple steps including deoxygenation, hydrocracking, and alkylation. This intermediary pathway enables the use of renewable sources while achieving the desired alkylbenzene products that can replace traditional fossil fuel-based production

Inventive Principle:
Principle #24Intermediary (Mediator)

2Object-affected harmful factors

If triglycerides from natural oils are used as feedstock, then renewable and sustainable production is achieved, but the feedstock contains unwanted components and requires complex processing

Engineering Contradiction:
Improveenvironmental impactVSAvoidprocess complexity
Core Design Contradiction:
Object-affected harmful factorsVSDevice complexity

Solution Approach 1:

The patent segments the complex triglyceride molecule into useful components through sequential processing steps: first deoxygenation to remove oxygen-containing groups, then hydrocracking to break down the carbon chain, and finally alkylation to form the desired alkylbenzene. This segmentation approach manages complexity by handling one transformation at a time

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The patent employs parameter changes in the form of different catalysts and reaction conditions for each processing step. By adjusting parameters such as temperature, pressure, and catalyst type at each stage, the process efficiently converts triglycerides into alkylbenzenes while managing the complexity through optimized conditions

Inventive Principle:
Principle #35Parameter changes

3Manufacturing precision

If the alkyl carbon number is in the range of 9 to 14, then the alkylbenzenes meet detergent industry specifications, but the feedstock contains higher carbon numbers (nC16 to nC18) that need conversion

Engineering Contradiction:
Improveproduct specification complianceVSAvoidconversion efficiency
Core Design Contradiction:
Manufacturing precisionVSProductivity

Solution Approach 1:

The patent uses parameter changes in the form of controlled hydrocracking conditions and catalyst selection to convert the carbon chain length from C16-C18 to the desired C9-C14 range. By adjusting reaction parameters, the process achieves the required product specification while maintaining reasonable conversion efficiency

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent applies local quality control by selectively converting specific portions of the triglyceride molecule. Through controlled hydrocracking, only the excess carbon chains are removed while preserving the core structure that will form the desired alkylbenzene product, thereby achieving specification compliance without wasting material

Inventive Principle:
Principle #3Local quality

4Object-affected harmful factors

If deoxygenation is performed to convert triglycerides to paraffins, then renewable feedstock is utilized, but the process produces branched isomers instead of linear paraffins

Engineering Contradiction:
Improveenvironmental impactVSAvoidproduct linearity
Core Design Contradiction:
Object-affected harmful factorsVSManufacturing precision

Solution Approach 1:

The patent uses parameter changes in the form of specific catalysts and reaction conditions during the hydrocracking step to control the branching of paraffin chains. By adjusting these parameters, the process minimizes branched isomer formation and maximizes linear paraffin production, achieving the required product linearity while maintaining renewable feedstock utilization

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent replaces non-selective thermal cracking with catalytic hydrocracking using specifically designed catalysts. This substitution allows for controlled breaking of carbon chains with minimal branching, achieving linear paraffins that would not form through conventional thermal methods alone

Inventive Principle:
Principle #28Mechanics substitution (Replace mechanical system)

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 process achieves a high yield of linear alkylbenzenes with greater than 90% linearity, utilizing renewable sources and reducing environmental impact by minimizing fossil fuel dependence, while maintaining biodegradability and effectiveness as detergent surfactants.

Implementation Method 1

deoxygenating a triglyceride which produces 60 wt. % or more of normal paraffins having less than 16 carbon atoms after hydrogenation

Methodology Applied
Scientific EffectHydrogenation: Hydrogenation

Implementation Method 2

linear selective cracking the C14+ stream in a separate linear selective cracking unit under linear selective cracking conditions in the presence of a linear selective cracking catalyst

Methodology Applied
Scientific EffectCatalysis: Catalysis

Implementation Method 3

dehydrogenating the decontaminated stream to provide a dehydrogenated stream comprising mono-olefins, di-olefins, and aromatics

Methodology Applied
Scientific EffectDehydrogenation:

Implementation Method 4

alkylating benzene with the mono-olefins under alkylation conditions to provide an alkylation effluent comprising alkylbenzenes and benzene

Methodology Applied
Scientific EffectAlkylation:

Data Source

PatentUS20240400472A1Process for producing renewable alkylbenzene products
Publication Date: 2024.12.05 UOP LLC
  • US20240400472A1 patent drawing
  • US20240400472A1 patent drawing
  • US20240400472A1 patent drawing

AI summary

Process for producing alkylbenzenes from triglycerides, in particular triglycerides having 60% or more of alkyl chains having less than 16 carbon atoms are described. The process include a linear selective cracking process to crack C14+ chains into C9 to C14 chains which are useful for making linear alkylbenzene for use in detergents.