Bifunctional Norbornane Compound Production via Low-Pressure Hydroformylation
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Solution Overview
Problem
Existing methods for producing bifunctional compounds with a norbornane skeleton require high-pressure conditions and are economically inefficient, as they necessitate expensive equipment and catalyst recycling, limiting their industrial applicability and cost-effectiveness.
Innovation Solution
A method involving a hydroformylation reaction of a monoolefin with carbon monoxide and hydrogen in the presence of a rhodium compound and an organic phosphorous compound, under pressures of 1 to 12 MPa, followed by a Diels-Alder reaction and subsequent hydrogenation, to produce a bifunctional compound with a norbornane skeleton, which can be isolated through distillation and used as an adhesive or resin raw material.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Quantity of substance
If hydroformylation is performed under high-pressure conditions (20-25 MPa) as described in Patent Document 2, then the production of tricyclodecane dicarbaldehyde is achieved, but expensive high-pressure resistant equipment is required and economic efficiency deteriorates
Solution Approach 1:
The patent applies parameter changes by reducing the reaction pressure from 20-25 MPa to 1-12 MPa, thereby eliminating the need for expensive high-pressure resistant equipment while maintaining productive production of tricyclodecane dicarbaldehyde
Solution Approach 2:
The patent employs a cheap rhodium catalyst system that does not require complex recycling equipment, accepting lower catalyst longevity in exchange for eliminating expensive high-pressure equipment and simplifying the overall manufacturing system
2Productivity
If hydroformylation is performed at reaction pressure of at least 9 MPa as described in Patent Documents 3 and 4, then high yield of tricyclodecane dicarbaldehyde is achieved, but the method requires high-pressure equipment and economic efficiency deteriorates
Solution Approach 1:
The patent changes the pressure parameter from at least 9 MPa to 1-12 MPa, achieving high yield productivity without requiring expensive high-pressure equipment, thereby improving economic efficiency
3Quantity of substance
If catalyst recycling equipment is installed as described in Patent Document 5, then rhodium complex catalyst cost is reduced, but device complexity and equipment costs increase
Solution Approach 1:
The patent uses a cheap rhodium catalyst system that can be used without complex recycling equipment, accepting lower catalyst recovery in exchange for eliminating expensive recycling infrastructure
Solution Approach 2:
The patent extracts the requirement for catalyst recycling equipment from the system, simplifying the overall device complexity while managing catalyst cost through alternative means
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 allows for the production of a novel bifunctional compound with a norbornane skeleton that exhibits excellent characteristics as an adhesive or resin raw material, while reducing the need for high-pressure equipment and minimizing catalyst costs, thereby enhancing economic efficiency and industrial practicability.
Implementation Method 1
a method involving a hydroformylation reaction of a monoolefin with carbon monoxide and hydrogen in the presence of a rhodium compound and an organic phosphorous compound
Implementation Method 2
in the presence of a rhodium compound and an organic phosphorous compound
Implementation Method 3
followed by a Diels-Alder reaction
Implementation Method 4
and subsequent hydrogenation
Implementation Method 5
which can be isolated through distillation
Data Source
AI summary
A process for producing a polycarbonate resin by reacting raw materials of a bifunctional compound and diphenyl carbonate, where the bifunctional compound is an isomer mixture of:a 2,6-derivative of a bifunctional compound of formula (3-a):anda 2,7-derivative of a bifunctional compound of formula (3-b):where R2 in formulae (3-a) and (3-b) is, independently, H, CH3 or C2H5,and where the mixing ratio between the 2,6-derivative and the 2,7-derivative is 30:70 to 70:30.