Esteramines from Metathesis-Modified Natural Oils
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Solution Overview
Problem
Esteramines and their derivatives made from traditional sources 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 for improved performance.
Innovation Solution
The development of esteramines comprising reaction products of metathesis-derived C10-C17 monounsaturated acids or octadecene-1,18-dioic acid with tertiary alkanolamines, which can be further quaternized, sulfonated, alkoxylated, sulfated, or sulfitated to create derivatives with enhanced properties for various applications.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Reliability
If traditional hydrolysis or transesterification of triglycerides is used to make esteramines, then the process is simple and well-established, but the products have predominantly cis-isomers and lack short-chain unsaturated fatty portions, limiting performance in surfactant applications
Solution Approach 1:
The patent applies parameter changes by modifying the chemical structure parameters of the fatty acid chains through metathesis reactions. Specifically, it transforms traditional C16-C22 chains into shorter C10-C17 chains and converts cis-isomers to trans-isomers, thereby improving surfactant performance while managing manufacturing complexity through controlled chemical transformation
Solution Approach 2:
The patent employs preliminary action by performing metathesis reactions on natural oils before esterification with alkanolamines. This pre-modification of the fatty acid feedstock ensures that the resulting esteramines possess the desired short-chain and trans-isomer characteristics, avoiding the need for complex post-synthesis modifications
2Reliability
If metathesis chemistry is used to generate precursors with shorter chains and trans-isomers, then surfactant performance is improved, but the manufacturing process becomes more complex
Solution Approach 1:
The patent uses metathesis catalysts as intermediaries to facilitate the transformation of natural oils into modified feedstocks. These catalysts enable the complex metathesis reactions to proceed efficiently, acting as mediators that simplify the overall process while achieving the desired molecular structure modifications for improved surfactant performance
Solution Approach 2:
The patent applies segmentation by breaking down the complex metathesis process into manageable stages: (1) self-metathesis of natural oils to produce C18 diesters, (2) cross-metathesis with α-olefins to generate shorter-chain unsaturated esters, and (3) subsequent esterification with alkanolamines. This staged approach reduces process complexity while maintaining performance benefits
3Productivity
If natural oils with C16-C22 fatty acid chains are used, then the feedstock is economical and readily available, but the resulting esteramines lack short-chain unsaturated portions needed for enhanced performance
Solution Approach 1:
The patent transforms the chain length parameter of fatty acids from traditional C16-C22 to shorter C10-C17 ranges through metathesis reactions. This parameter change maintains economic efficiency by using abundant natural oils as starting materials while achieving the short-chain structure necessary for enhanced surfactant performance
Solution Approach 2:
The patent discards the excess carbon atoms from longer fatty acid chains through metathesis reactions that cleave and recombine carbon-carbon double bonds. The shorter-chain products (C10-C17 unsaturated esters) are recovered as valuable intermediates for esteramine synthesis, converting what would be waste into useful materials while maintaining economic efficiency
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 esteramines and derivatives exhibit improved physical properties and expanded end-use applications, including cleaners, personal care products, and agricultural uses, due to their modified unsaturation and trans-isomer content, offering improved performance and flexibility in formulation.
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
Metathesis effectively isomerizes the cis-double bond of methyl oleate to give an equilibrium mixture of cis- and trans-isomers in both the 'unconverted' starting material and the metathesis products, with the trans-isomers predominating
Implementation Method 3
Cross-metathesis of unsaturated fatty esters with olefins generates new olefins and new unsaturated esters that can have reduced chain length and that may be difficult to make otherwise
Data Source
AI summary
Esteramine compositions and their derivatives are disclosed. The esteramines comprise a reaction product of a metathesis-derived C10-C17 monounsaturated acid, octadecene-1,18-dioic acid, or their ester derivatives with a tertiary alkanolamine. Derivatives made by quaternizing, sulfonating, alkoxylating, sulfating, and/or sulfitating the esteramines are also disclosed. 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 esteramines and 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.