PIDA Monomer Synthesis via Organometallic Catalysis

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Solution Overview

Problem

Current methods for synthesizing phenylindane dicarboxylic acid (PIDA) monomers are limited by rigorous reaction conditions, such as the use of propylene gas and high temperature, and lack chemo-selectivity, restricting large-scale production due to low yields and selectivity.

Innovation Solution

A method involving reacting an alkylstyrene under specific conditions to produce phenylindane, followed by further reaction to obtain PIDA monomers, which allows for improved yield and selectivity with less rigorous conditions, enabling scalable production.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Manufacturing precision

If traditional synthesis methods using propylene gas, high pressure, and high temperature are employed, then PIDA monomer can be produced, but the reaction conditions are rigorous and chemo-selectivity is poor, restricting large-scale production

Engineering Contradiction:
Improvechemo-selectivityVSAvoidreaction condition complexity
Core Design Contradiction:
Manufacturing precisionVSEase of manufacture

Solution Approach 1:

The patent changes the reaction parameters from traditional high temperature and high pressure conditions to milder conditions using organometallic catalysts. Specifically, it employs catalysts such as palladium, platinum, or rhodium complexes with ligands like phosphines or N-heterocyclic carbenes, allowing the reaction to proceed at lower temperatures and pressures while achieving high chemo-selectivity and yield.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent introduces organometallic catalysts as intermediaries to mediate the reaction between alkylstyrene and carbon monoxide. These catalysts facilitate the carbonylation reaction by providing a controlled pathway that enhances chemo-selectivity, preventing side reactions that occur in traditional methods without such catalytic intermediaries.

Inventive Principle:
Principle #24Intermediary (Mediator)

2Productivity

If traditional synthesis methods are used, then PIDA can be produced, but yields are low and selectivity is poor, restricting scalability

Engineering Contradiction:
Improveyield and selectivityVSAvoidscalability
Core Design Contradiction:
ProductivityVSQuantity of substance

Solution Approach 1:

The patent optimizes reaction parameters including temperature, pressure, and catalyst concentration to achieve high yields and selectivity. By conducting the reaction at moderate temperatures (50-150°C) and pressures (1-10 atm) with optimized catalyst loading, the method achieves yields exceeding 90% with high selectivity, enabling scalable production.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent replaces the traditional mechanical/thermal approach (high temperature and pressure) with a chemical catalytic approach using organometallic complexes. This substitution allows for milder reaction conditions while achieving superior productivity through enhanced reaction efficiency and selectivity catalyzed by the metal complexes.

Inventive Principle:
Principle #28Mechanics substitution (Replace mechanical system)

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 method provides high yield and selectivity for PIDA monomers, facilitating the production of cost-effective, transparent, and melt-stable polymer compositions suitable for environmentally friendly alternatives to polycarbonates and polyesters.

Implementation Method 1

reacting an alkylstyrene under first reaction conditions effective to provide a first reaction product comprising at least one phenylindane; and reacting the first reaction product under second reaction conditions effective to provide a second reaction product comprising at least one phenylindane dicarboxylic acid (PIDA) monomer

Methodology Applied
Scientific EffectChemical reaction: Chemical Bonding

Data Source

PatentUS9238609B2Dicarboxylic acid monomers and methods of making and using the same
Publication Date: 2016.01.19 SHPP GLOBAL TECH BV
  • US9238609B2 patent drawing
  • US9238609B2 patent drawing
  • US9238609B2 patent drawing

AI summary

Disclosed herein are phenylindane dicarboxylic acid (PIDA) monomers, polymer compositions comprising the PIDA monomers, and methods of preparing PIDA monomers. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present disclosure.