Transesterification of Phosphates with Dianhydrohexitols
Find Innovative SolutionsGenerate Solutions
Solution Overview
Problem
Current methods for producing halogen-free flame retardants like isosorbide bis(diphenyl phosphate) face challenges such as the need for handling and separation of solid by-products, use of solvents, and reactivity issues with chlorine phosphates, which limit industrial scalability and efficiency.
Innovation Solution
A process involving the transesterification of phosphates or thiophosphates with 1,4:3,6-dianhydrohexitols in the presence of catalytic amounts of bases or Lewis acids, eliminating the need for solvent use and reducing corrosion concerns, allowing for higher yields and easier implementation.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Ease of manufacture
If triethylamine is used as a base catalyst in the reaction, then the reaction can proceed, but triethylammonium hydrochloride solid by-product is formed requiring handling and separation
Solution Approach 1:
The patent removes the problematic solid by-product formation by extracting the chloride component from the reaction system. Instead of using chlorophosphates that release HCl, the invention uses phosphates that do not generate acidic by-products, thereby eliminating the need to handle and separate triethylammonium hydrochloride solid
Solution Approach 2:
The patent introduces a different reaction mechanism using phosphates as intermediaries instead of chlorophosphates. This intermediary approach allows the transesterification to proceed without generating the problematic solid by-product, solving both the reaction feasibility and by-product handling issues
2Ease of manufacture
If toluene is used as a solvent, then the reaction can proceed, but the space-time yield is reduced
Solution Approach 1:
The patent removes the solvent from the reaction system entirely. By using phosphates that do not require solvent mediation for the transesterification reaction, the invention achieves solvent-free conditions that maximize space-time yield while maintaining reaction feasibility
Solution Approach 2:
The reaction system becomes self-sufficient by eliminating the need for external solvent. The phosphate reactants and catalyst system work together in a solvent-free environment, allowing the reaction to proceed efficiently without reducing space-time yield
3Speed
If diaryl chlorophosphate is used, then the reaction proceeds rapidly, but chloride corrosion requires expensive corrosion-resistant materials
Solution Approach 1:
The patent converts the harmful chloride release issue into a beneficial feature by using phosphates that do not release chloride. This eliminates the corrosion problem entirely, allowing the use of ordinary equipment materials instead of expensive corrosion-resistant alloys, while still achieving rapid reaction through catalytic activation
Solution Approach 2:
The patent changes the chemical parameters of the reactant from chlorophosphate to phosphate, fundamentally altering the reaction mechanism to eliminate chloride release. This parameter change maintains reaction efficiency through catalysis while eliminating the corrosion issue that required expensive materials
4Stability of the object's composition
If the reaction is carried out in the absence of moisture, then diaryl chlorophosphate stability is maintained, but the process becomes more complex and yield is reduced due to hydrolysis
Solution Approach 1:
The patent converts the moisture sensitivity issue into a beneficial feature by using phosphates that are inherently stable in the presence of moisture. Instead of requiring strict exclusion of water, the reaction system welcomes moisture-tolerant conditions, eliminating hydrolysis losses and simplifying the process while maintaining high yields
Solution Approach 2:
The patent changes the chemical parameter of the reactant from moisture-sensitive chlorophosphate to moisture-stable phosphate. This fundamental parameter change allows the reaction to proceed under relaxed moisture conditions, eliminating the need for complex moisture exclusion measures and preventing yield reduction from hydrolysis
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 enhances the production of sugar phosphates or thiophosphates, offering improved space-time yields, reduced material requirements, and simplified industrial implementation, while maintaining effective flame retardant properties.
Implementation Method 1
by transesterification of at least one phosphate or thiophosphate of the formula (I) with at least one 1,4:3,6-dianhydrohexitol of the formula (III) in the presence of at least one catalyst from the group of bases and Lewis acids
Data Source
AI summary
The invention relates to processes for the production of a sugar phosphate or thiophosphate by transesterification of at least one phosphate or thiophosphate of formula (I) with at least one sugar in the presence of at least one catalyst from the group of bases and Lewis acids, wherein the substituents X and R in formula (I) have the following meaning: X is equal to or different from O or S; R is equal to or different from a straight-chain or branched C1-C16 alkyl group, a straight-chain or branched C2-C16 alkenyl group, C3-C10 cycloalkyl, C6-C10 aryl, benzyl or two substituents R together with the O atoms to which they are bonded and the P atom form a ring, wherein the substituents R are unsubstituted or substituted by one or more residues OH, C1-C4 alkyl, CF3, C3-C7 cycloalkyl, C1-C4 alkoxy, C1-C4 alkenyl, C6-C10 aryl, CN.