Multi-functional Compounds from Unsaturated Organo-nitriles
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Solution Overview
Problem
There is a need for new uses and applications for unsaturated organo-nitriles, which are by-products of commercial processes, as existing technologies do not effectively utilize these materials.
Innovation Solution
A two-stage process is developed to convert unsaturated organo-nitriles into novel multi-functional compounds, which can serve as cross-linking agents, chelating agents, curatives, and components in coating systems, particularly in the formation of polyamides.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Adaptability or versatility
If unsaturated organo-nitriles are used as by-products of commercial processes, then existing technologies do not effectively utilize these materials, but converting them to multi-functional compounds creates new valuable applications
Solution Approach 1:
The patent converts unsaturated organo-nitriles, which are currently wasted by-products from adiponitrile production, into valuable multi-functional compounds through a two-stage chemical process. These compounds serve as cross-linking agents, chelating agents, curatives, and coating system components, transforming a harmful waste stream into a beneficial resource with multiple industrial applications.
Solution Approach 2:
The resulting multi-functional compounds can be applied across multiple industrial sectors including polyamide formation, coating systems, and as cross-linking agents. The compounds possess multiple functional groups (amide, acid, amine, guanamine, heterocyclic) that enable diverse chemical reactions and applications, making them universally useful across different manufacturing processes.
2Adaptability or versatility
If a two-stage process is used to convert unsaturated organo-nitriles to multi-functional compounds, then new applications are created, but the process complexity increases
Solution Approach 1:
The conversion process is divided into two distinct stages: (1) conversion of unsaturated organo-nitriles to hydroxy-aminonitriles, and (2) functionalization of hydroxy-aminonitriles to multi-functional compounds. This segmentation allows each stage to be optimized independently and facilitates easier process control and scaling compared to a single complex one-step process.
Solution Approach 2:
Hydroxy-aminonitriles serve as an intermediate compound that bridges the starting material (unsaturated organo-nitrile) and the final multi-functional compounds. This intermediate facilitates the transformation by providing reactive functional groups that enable subsequent reactions to form the diverse array of useful compounds including amides, acids, amines, and heterocyclic structures.
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 multi-functional compounds demonstrate utility in various applications, enhancing the value and utilization of unsaturated organo-nitriles, which were previously underutilized.
Implementation Method 1
feeding an unsaturated organonitrile, a hydroxy-amine, and optionally, a solvent to a first reaction zone... to obtain a hydroxy-aminonitrile of the molecular structure [II]
Implementation Method 2
maintaining the reaction conditions in the second reaction zone for time sufficient for functionalizing the hydroxy-aminonitrile of the molecular structure [II] to obtain a composition of matter of the molecular structure [I]... terminal functional group selected from the group consisting of amide [—CONH2], acid [—COOH], amine [—CH2—NH2], guanamine [—(C3N3)—(NH2)2], organic heterocyclic [—CHN4]
Data Source
AI summary
A new composition of matter has the molecular structure [I]: Formula (I) wherein R1 is an alkyl, cycloalkyl, aralkyl group having ≥1 to ≤10 carbon atoms; R2 is selected from the group consisting of an aliphatic C1-C10 group, an unsaturated C1-C10 chain, C4-C9 group with a cyclic portion and C4-C10 group with an aromatic portion, and combinations thereof; R3 is selected from the group consisting of hydrogen, an aliphatic C1-C10 group, an unsaturated C2-C10 chain, a C4-C10 group with a cyclic portion, C4-C10 group with an aromatic portion, and combinations thereof; and R4 is a terminal functional group selected from the group consisting of amide [—CONH2], acid [—COOH], amine [—CH2—NH2], guanamine [—(C3N3)—(NH2)2], organic heterocyclic [—CHN4], and combinations thereof; and wherein said composition of matter of the molecular structure [I] excludes 2-[(3-amino-1-ethylpropyl)amino]ethanol.