Quaternized Fatty Amines from Metathesis-Derived Acids
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Solution Overview
Problem
Traditional sources of fatty acids and esters for making quaternized fatty amines and their derivatives primarily contain predominantly cis isomers and lack short-chain unsaturated fatty portions, limiting their performance and versatility in surfactant applications, while metathesis chemistry offers opportunities to generate precursors with shorter chains and mostly trans isomers.
Innovation Solution
The development of quaternary ammonium, betaine, and sulfobetaine compositions derived from metathesis-derived C10-C17 monounsaturated acids or their ester derivatives, which can be used to create a variety of downstream compositions with improved performance characteristics, including increased trans unsaturation for enhanced physical properties.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Adaptability or versatility
If traditional fatty acids and esters are used for making quaternized fatty amines, then the production process is well-established and reliable, but the products lack short-chain unsaturated fatty portions and predominantly contain cis isomers, limiting their performance and versatility in surfactant applications
Solution Approach 1:
The invention changes the chemical parameters of the starting materials by using metathesis-derived fatty acids and esters with different chain lengths and trans unsaturation compared to traditional cis-isomer-rich feedstocks. This parameter change enables the production of quaternized fatty amines with improved surfactant performance and versatility while maintaining a practical manufacturing process
Solution Approach 2:
The invention introduces metathesis chemistry as an intermediary process that transforms traditional fatty acids and esters into modified precursors with desirable properties (shorter chains, trans unsaturation). This intermediary step enables the subsequent amine formation and quaternization to produce superior surfactants without requiring complete process redesign
2Reliability
If metathesis chemistry is used to generate precursors with shorter chains and trans isomers, then the physical properties and performance characteristics are improved, but the manufacturing process becomes more complex
Solution Approach 1:
The invention performs the metathesis reaction as a preliminary action before amine formation and quaternization. This preliminary modification of the fatty acid/ester precursors establishes the desired chain length and trans unsaturation early in the process, ensuring improved physical properties and performance characteristics in the final product while allowing subsequent steps to proceed with modified but manageable complexity
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
These compositions exhibit improved physical properties and expanded utility in cleaners, personal care products, agricultural uses, and oilfield applications, offering greater latitude in formulation and performance compared to traditional derivatives.
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
Data Source
AI summary
Quaternary ammonium, betaine, or sulfobetaine compositions derived from fatty amines, wherein the fatty amine is made by reducing the amide reaction product of of a metathesis-derived C10-C17 monounsaturated acid, octadecene-1,18-dioic acid, or their ester derivatives and a secondary amine, are disclosed. Quaternary ammonium, betaine, or sulfobetaine compositions derived from fatty amidoamines, wherein the amidoamine is made by reacting of a metathesis-derived C10-C17 monounsaturated acid, octadecene-1,18-dioic acid, or their ester derivatives and an aminoalkyl- substituted tertiary amine, are also disclosed. The quaternized compositions are advantageously sulfonated or sulfitated. In one aspect, the ester derivative of the C10- C17 monounsaturated acid or octadecene-1,18-dioic acid is a lower alkyl ester. In other aspects, the ester derivative is a modified triglyceride made by self-metathesis of a natural oil or an unsaturated triglyceride made by cross-metathesis of a natural oil with an olefin. The quaternary ammonium, betaine, and sulfobetaine compositions and their sulfonated or sulfitated derivatives are valuable for a wide variety of end uses, including cleaners, fabric treatment, hair conditioning, personal care (liquid cleansing products, conditioning bars, oral care products), antimicrobial compositions, agricultural uses, and oil field applications.