2,2'-Bis(Carboxymethoxy)-1,1'-Binaphthyl Salt Filtration

Resolve Bottlenecks,
Find Innovative Solutions
Generate Solutions

Solution Overview

Problem

Existing methods for producing 2,2'-bis(carboxymethoxy)-1,1'-binaphthyl result in decreased yield and purity due to the reaction of the carboxylic acid with alcohol after hydrolysis, leading to ester formation and the need for distilling off the reaction solvent under reduced pressure, which generates waste and increases costs.

Innovation Solution

A production method involving a separation step to isolate the metal salt of 2,2'-bis(carboxymethoxy)-1,1'-binaphthyl through solid-liquid separation, followed by filtration and removal of the mother liquor, without distilling off the reaction solvent under reduced pressure.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Manufacturing precision

If the reaction solvent containing ester-derived alcohol is distilled off from the reaction system under reduced pressure after hydrolysis reaction, then the purity of the target is improved, but the productivity is worsened and waste is generated

Engineering Contradiction:
Improvepurity of targetVSAvoidproduction efficiency
Core Design Contradiction:
Manufacturing precisionVSProductivity

Solution Approach 1:

The invention extracts and removes the ester-derived alcohol from the reaction system through distillation before acidification. By taking out the harmful alcohol component early in the process, the subsequent acidification step can proceed without causing esterification side reactions, thereby achieving high purity target product without requiring additional purification steps that would reduce productivity

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The invention performs the distillation of ester-derived alcohol as a preliminary action before the acidification step. By removing the alcohol beforehand, the system prevents the formation of ester side products during acidification, eliminating the need for later purification operations and maintaining high production efficiency

Inventive Principle:
Principle #10Preliminary action

2Manufacturing precision

If the reaction solvent is distilled off under reduced pressure, then the purity is improved, but the loss of substance increases due to solvent waste

Engineering Contradiction:
Improvepurity of targetVSAvoidsolvent waste
Core Design Contradiction:
Manufacturing precisionVSLoss of substance

Solution Approach 1:

The invention implements a solvent recovery system where the distilled-off reaction solvent containing ester-derived alcohol is collected and reused in subsequent reactions. This approach eliminates waste generation while maintaining the purity benefits of the distillation step, as the recovered solvent can be used again in the esterification reaction without significant loss of effectiveness

Inventive Principle:
Principle #34Discarding and recovering

3Manufacturing precision

If the reaction solvent is distilled off under reduced pressure, then the purity is improved, but the device complexity and operational complexity increase

Engineering Contradiction:
Improvepurity of targetVSAvoidprocess complexity
Core Design Contradiction:
Manufacturing precisionVSDevice complexity

Solution Approach 1:

The invention combines the distillation step with the existing reaction setup by using the same reaction vessel for both esterification and subsequent distillation operations. By merging these operations into a single equipment system, the patent avoids adding complex additional apparatus while still achieving the necessary solvent removal for high purity product

Inventive Principle:
Principle #5Merging (Combining)

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 achieves high-purity 2,2'-bis(carboxymethoxy)-1,1'-binaphthyl with reduced solvent use, minimizing waste generation and lowering production costs while maintaining high yield.

Implementation Method 1

hydrolysis of a diester obtained by the reaction

Methodology Applied
Scientific EffectHydrolysis: Hydrolysis

Implementation Method 2

separation step of separating a metal salt of 2,2'-bis(carboxymethoxy)-1,1'-binaphthyl from a reaction mixture by solid-liquid separation, the separation step comprising filtration of the metal salt

Methodology Applied
Scientific EffectFiltration: Filter (physical)

Data Source

PatentEP4067331B1Preparation method for 2,2'-bis(carboxymethoxy)-1,1'-binaphthyl
Publication Date: 2025.10.29 HONSHU CHEM INDAL
  • EP4067331B1 patent drawing
  • EP4067331B1 patent drawing
  • EP4067331B1 patent drawing

AI summary

An object is to provide a production method that can provide highly pure 2,2'-bis(carboxymethoxy)-1,1'-binaphthyl with good production efficiency. As a solution, a method for producing 2,2'-bis(carboxymethoxy)-1,1'-binaphthyl represented by formula (3) includes a separation step of separating a metal salt of 2,2'-bis(carboxymethoxy)-1,1'-binaphthyl, the metal salt being represented by formula (2), from a reaction mixture by solid-liquid separation. In the method, a 2,2'-bis(alkoxycarbonylmethoxy)-1,1'-binaphthyl represented by formula (1) is used as a starting material.