Metathesis-Derived Alkoxylated Fatty Esters for Surfactant Performance
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Solution Overview
Problem
Alkoxylated fatty esters and their derivatives from traditional sources typically have predominantly cis-isomers and lack short-chain unsaturated fatty portions, limiting their performance in surfactant applications, while metathesis chemistry offers opportunities to generate precursors with shorter chains and mostly trans-isomers, which could enhance performance.
Innovation Solution
The development of alkoxylated fatty esters derived from metathesis-derived C10-C17 monounsaturated acids or octadecene-1,18-dioic acids, which are reacted with alkylene oxides in the presence of an insertion catalyst, resulting in products with a high proportion of trans-Δ9 unsaturation, expanding the range of available precursors and allowing for further functionalization such as sulfonation or sulfitation.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Reliability
If traditional fatty acids or esters are used to make alkoxylated fatty esters, then the manufacturing process is well-established and reliable, but the products lack short-chain unsaturated fatty portions and have predominantly cis-isomers, limiting their performance in surfactant applications
Solution Approach 1:
The patent applies parameter changes by modifying the chemical structure parameters of the starting materials through metathesis reactions. This transforms traditional C16-C22 fatty acids with cis-configuration into metathesis-derived fatty acids with shorter chains (C10-C17) and trans-configuration, thereby improving surfactant performance while maintaining manufacturing reliability
Solution Approach 2:
The patent uses metathesis chemistry as an intermediary process between traditional fat hydrolysis and final alkoxylated fatty ester production. This intermediary step introduces short-chain unsaturated fatty portions and trans-isomers into the product structure, enabling improved surfactant applications
2Adaptability or versatility
If metathesis chemistry is used to generate precursors with shorter chains and trans-isomers, then the surfactant performance is enhanced, but the manufacturing process becomes more complex
Solution Approach 1:
The patent applies preliminary action by performing metathesis reactions on the starting fatty acid or ester before the alkoxylization step. This preliminary transformation of the carbon chain structure and unsaturation configuration enables the subsequent alkoxylated fatty ester to achieve improved surfactant performance characteristics
Solution Approach 2:
The patent demonstrates universality by showing that metathesis chemistry can be applied to various natural oils and fats to consistently produce short-chain unsaturated fatty acids with trans-isomers, which then serve multiple surfactant applications. The process handles different feedstocks (triglycerides, fatty acids, fatty esters) through a unified metathesis approach
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
The resulting alkoxylated fatty esters exhibit improved physical properties and performance characteristics, enabling broader applications in cleaners, personal care products, agricultural uses, and other end uses, with enhanced trans-unsaturation levels compared to naturally sourced counterparts.
Implementation Method 1
metathesis relies on conversion of olefins into new products by rupture and reformation of carbon-carbon double bonds mediated by transition metal carbene complexes
Implementation Method 2
inserting of one or more alkylene oxide units, usually ethylene oxide (EO), between the oxygen and CH3 portions of a methoxy group of a methyl ester using mixed oxide catalysts
Data Source
AI summary
Alkoxylated fatty ester compositions are disclosed. In one aspect, the compositions comprise a reaction product of a metathesis-derived C10-C17 monounsaturated acid, octadecene-1,18-dioic acid, or their ester derivatives with one or more alkylene oxides in the presence of an insertion catalyst to give an alkoxylated fatty ester. In another aspect, the metathesis-derived C10-C17 monounsaturated acid, octadecene-1,18-dioic acid, or its ester derivative is reacted with a glycol ether or a glycol ether alkoxylate, to give an alkoxylated fatty ester. In yet another aspect, the metathesis-derived C10-C17 monounsaturated acid or octadecene-1,18-dioic acid is reacted with one or more alkylene oxides to give a fatty acid alkoxylate, followed by etherification of the fatty acid alkoxylate.