HMTBN Synthesis via pH Adjustment and HCN Extraction

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Solution Overview

Problem

Existing methods for producing 2-hydroxy-4-methylthiobutyronitrile (HMTBN) and 2-hydroxy-4-methylselenobutyronitrile (HMSeBN) from 3-methylthiopropanal (MTP) and hydrocyanic acid (HCN) result in significant residual concentrations of HCN and MTP, leading to decreased product quality and increased treatment costs due to the formation of by-products and degradation products.

Innovation Solution

Adjusting the molar ratio of HCN to MTP to a value greater than or equal to 1 and maintaining the pH at a value greater than or equal to 3.5, followed by lowering the pH to less than or equal to 2.5 to extract HCN, promoting the consumption of MTP and reducing residual aldehyde and HCN in the reaction medium.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If the reaction is carried out with HCN and MTP in conventional conditions, then HMTBN is produced with high yield, but significant residual concentrations of HCN and MTP remain in the product

Engineering Contradiction:
ImproveHMTBN production yieldVSAvoidProduct purity
Core Design Contradiction:
ProductivityVSManufacturing precision

Solution Approach 1:

The patent applies parameter changes by adjusting the pH of the reaction medium to a value between 2 and 4, which optimizes the reaction conditions to minimize residual HCN and MTP while maintaining high HMTBN yield. This pH adjustment fundamentally changes the reaction environment to favor complete consumption of reactants.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent employs extraction to remove residual HCN from the reaction medium by contacting it with an organic solvent. This separation step effectively extracts the harmful residual HCN, thereby improving the purity of the final HMTBN product while maintaining high production yield.

Inventive Principle:
Principle #2Taking out (Extraction)

2Productivity

If residual HCN is present in HMTBN, then the reaction can proceed efficiently, but formic acid forms in downstream steps causing quality degradation and increased treatment costs

Engineering Contradiction:
ImproveReaction efficiencyVSAvoidFormic acid formation
Core Design Contradiction:
ProductivityVSObject-generated harmful factors

Solution Approach 1:

The patent applies preliminary anti-action by adjusting the pH to 2-4 and extracting HCN before the downstream steps occur. This preemptive removal of HCN prevents its subsequent conversion to formic acid, thereby eliminating the harmful effect before it can manifest in later processing stages.

Inventive Principle:
Principle #9Preliminary anti-action

Solution Approach 2:

The patent converts the potentially harmful presence of residual HCN into a benefit by using controlled pH adjustment and extraction. The HCN that would otherwise cause formic acid formation is instead selectively removed and can be recovered or safely disposed of, turning a liability into a manageable parameter.

Inventive Principle:
Principle #22Blessing in disguise (Convert harm into benefit)

3Speed

If residual MTP remains in the reaction medium, then the reaction proceeds faster, but degradation products form reducing product quality

Engineering Contradiction:
ImproveReaction rateVSAvoidProduct quality
Core Design Contradiction:
SpeedVSManufacturing precision

Solution Approach 1:

The patent uses parameter changes by maintaining pH between 2 and 4 to optimize the reaction conditions. This pH range allows the reaction to proceed at high speed while simultaneously minimizing the formation of degradation products from residual MTP, thus maintaining both reaction rate and product quality.

Inventive Principle:
Principle #35Parameter changes

4Device complexity

If HCN extraction is performed without pH adjustment, then the process is simpler, but HCN removal is incomplete and product quality suffers

Engineering Contradiction:
ImproveProcess complexityVSAvoidHCN removal efficiency
Core Design Contradiction:
Device complexityVSManufacturing precision

Solution Approach 1:

The patent applies preliminary action by adjusting the pH to 2-4 before performing the HCN extraction. This preparatory step modifies the reaction medium to favor complete HCN removal, ensuring that the subsequent extraction process is highly efficient and produces high-quality product.

Inventive Principle:
Principle #10Preliminary action

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 effectively reduces the concentration of MTP and HCN, enhancing synthesis yields, improving product quality, and minimizing costly effluent treatments, while being adaptable to conventional production lines without substantial transformation.

Implementation Method 1

the MTP is reacted with the HCN in the presence of a catalyst selected from amines, in a multizone reactor, to produce a reaction mixture containing the HMTBN formed

Methodology Applied
Scientific EffectChemical reaction: Chemical Bonding

Implementation Method 2

the unreacted HCN is extracted from the reaction medium to an absorption zone containing MTP and the catalyst

Methodology Applied
Scientific EffectExtraction: Liquid-Liquid Extraction

Data Source

PatentUS20240076267A1Method for preparing 2-hydroxy-4-methylthiobutyronitrile or the selenium equivalent thereof, and applications
Publication Date: 2024.03.07 ADISSEO FRANCE SAS

AI summary

A method for the preparation of the 2-hydroxy-4-methylthiobutyronitrile (HMTBN) or its selenium equivalent (HMSeBN) from hydrocyanic acid and 3-methylthiopropanal (MTP) or the corresponding selenium aldehyde (MSeP) includes the following steps: the molar ratio of the HCN to MTP or to MSeP is adjusted to a value greater than or equal to 1 and the pH is adjusted and maintained at a value greater than or equal to 3.5, to obtain a reaction medium in which the HMTBN or the HMSeBN is formed, then the pH of the reaction medium is lowered to a value less than or equal to 2.5 and the HCN is extracted from the reaction medium, and the HMTBN or the HMSeBN is recovered. The applications of this method are also related.