Biphase Alcohol Synthesis via Phase-Transfer Catalysis
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Solution Overview
Problem
The existing process for producing 3-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)-1-propyl alcohol, an intermediate for insecticides, is complex due to its multi-step nature.
Innovation Solution
A process involving the reaction of a phenol with a haloalcohol in a biphase system composed of a water-immiscible organic solvent and an aqueous alkali metal hydroxide solution, in the presence of a phase-transfer catalyst, to efficiently produce the alcohol compound with fewer steps.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Ease of manufacture
If a multi-step process is used to produce the alcohol compound, then the production can be performed with conventional methods, but the process becomes complicated and less efficient
Solution Approach 1:
The patent combines multiple reaction steps into a single step by using a biphase system with phase-transfer catalyst. The phenol and haloalcohol react in one operation to directly form the alcohol compound, eliminating the need for separate intermediate steps (such as forming and hydrolyzing ester intermediates in the conventional process). This merging of steps directly reduces process complexity while maintaining production efficiency.
Solution Approach 2:
The patent changes the reaction parameters by introducing a biphase system composed of water-immiscible organic solvent and aqueous alkali metal hydroxide solution, with phase-transfer catalyst. This parameter change enables the reaction to proceed under new conditions that allow direct formation of the alcohol compound, simplifying the process while maintaining or improving productivity.
2Productivity
If multiple steps are used to produce the alcohol compound, then conventional methods can be applied, but the number of steps increases and time is lost
Solution Approach 1:
The patent merges multiple sequential steps into a single reaction operation. The conventional process requires separate steps for forming intermediate compounds and subsequent hydrolysis, whereas the invention achieves the same transformation in one step using the biphase system with phase-transfer catalyst, thereby eliminating time loss associated with multiple sequential operations.
Solution Approach 2:
The patent enables continuous useful action by performing the transformation in a single uninterrupted reaction step. The biphase system allows the reaction to proceed continuously from reactants to product without the interruptions and waiting periods inherent in multi-step processes, thereby reducing total process time and improving productivity.
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 efficient production of the alcohol compound with higher yields and simplified steps, making it a more effective process for producing an intermediate useful in insecticide synthesis.
Implementation Method 1
reacting a phenol represented by the formula (1) with a haloalcohol represented by the formula (2) in a biphase system composed of a water-immiscible organic solvent and an aqueous alkali metal hydroxide solution in the presence of a phase-transfer catalyst
Data Source
AI summary
A process for the production of an alcohol compound represented by the formula (3):wherein X1, X2, X3, X4, Z, R and n are as defined below, comprising reacting a phenol represented by the formula (1):wherein X1, X2, X3 and X4 independently represent a hydrogen atom, a halogen atom or an alkyl group having 1 to 3 carbon atoms; Z represents an oxygen atom or a sulfur atom; and R represents a halogen-substituted alkenyl group, with a haloalcohol represented by the formula (2):wherein Y represents a chlorine atom or a bromine atom; and n represents an integer of 2 or 3, in a biphase system composed of a water-immiscible organic solvent and an aqueous alkali metal hydroxide solution in the presence of a phase-transfer catalyst.