Sarcosine Preparation via Schiff Base Hydrogenation

Solution Overview

Problem

Current methods for producing sodium sarcosinate and its derivatives, such as creatine, face issues with the use of highly toxic chemicals, low yield, high production costs, and environmental concerns, including the generation of corrosive by-products and complex purification processes.

Innovation Solution

A novel preparation method involving the reaction of glyoxylic acid or glyoxylate with an amine to form a Schiff base, followed by hydrogenation and pH adjustment, which eliminates the need for toxic raw materials and simplifies the process, resulting in higher yields and reduced environmental impact.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Ease of manufacture

If the chloroacetic acid method is used to prepare sodium sarcosinate, then the reaction can proceed under relatively simple conditions, but the yield is low (only about 50%) and the process generates highly corrosive hydrogen chloride gas requiring expensive acid-resistant equipment

Engineering Contradiction:
Core Design Contradiction:
Ease of manufactureVSProductivity

Solution Approach 1:

The invention changes the reaction parameters by using different reactants (formaldehyde instead of chloroacetic acid) and adjusting pH conditions to achieve both high yield and simple operation. The new method operates at pH 7-10 with formaldehyde and sodium hydroxide, eliminating the need for pressurized conditions while achieving over 90% yield

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention converts the harmful chloroacetic acid method that produces corrosive HCl gas into a beneficial formaldehyde-based method that produces no corrosive by-products. The new approach uses readily available formaldehyde and sodium hydroxide to generate sodium sarcosinate directly, turning a harmful process into a clean one

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

2Ease of manufacture

If the chloroacetic acid method is used to prepare sodium sarcosinate, then the reaction can proceed under relatively simple conditions, but expensive acid-resistant equipment is required due to corrosive hydrogen chloride gas production

Engineering Contradiction:
Core Design Contradiction:
Ease of manufactureVSDevice complexity

Solution Approach 1:

The invention eliminates the harmful HCl gas production by using formaldehyde instead of chloroacetic acid as the reactant. This conversion removes the need for expensive acid-resistant equipment while maintaining simple reaction conditions, achieving both cost-effectiveness and operational simplicity

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

3Adaptability or versatility

If the hydroxyacetonitrile method is used to prepare sodium sarcosinate, then the process can be carried out with common chemicals, but the yield is low and highly toxic hydrocyanic acid must be handled requiring special safety measures

Engineering Contradiction:
Core Design Contradiction:
Adaptability or versatilityVSProductivity

Solution Approach 1:

The invention converts the toxic hydrocyanic acid method into a safe formaldehyde-based process. By using formaldehyde and sodium hydroxide instead of hydrocyanic acid, the method eliminates toxicity while maintaining raw material availability and achieving high yield through direct reductive amination

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

4Adaptability or versatility

If the hydroxyacetonitrile method is used to prepare sodium sarcosinate, then the process can be carried out with common chemicals, but the yield is low (similar to other conventional methods)

Engineering Contradiction:
Core Design Contradiction:
Adaptability or versatilityVSProductivity

Solution Approach 1:

The invention optimizes reaction parameters by controlling pH at 7-10 and using excess formaldehyde to drive the reductive amination reaction to completion. These parameter changes achieve over 90% yield while using readily available formaldehyde and sodium hydroxide as reactants

Inventive Principle:
Principle #35Parameter changes

5Ease of manufacture

If conventional methods are used to prepare sodium sarcosinate, then the process can be established, but complex purification processes are required to remove by-products and debittering agents

Engineering Contradiction:
Core Design Contradiction:
Ease of manufactureVSDevice complexity

Solution Approach 1:

The invention eliminates the need for complex purification and debittering processes by using formaldehyde instead of chloroacetic acid. The reaction produces minimal by-products that can be removed by simple filtration and washing, eliminating the need for debittering agents like sodium thiosulfate and complex purification steps

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

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 a safer, more efficient, and cost-effective production of sodium sarcosinate and its derivatives, with improved product quality and reduced environmental pollution, making it suitable for industrial-scale production.

Implementation Method 1

reacting a solution of glyoxylic acid or a glyoxylate with an amine solution to prepare a Schiff base solution

Methodology Applied
Scientific EffectCondensation reaction:

Implementation Method 2

subjecting the prepared Schiff base solution to a hydrogenation reaction under the condition of a catalyst

Methodology Applied
Scientific EffectHydrogenation: Hydrogenation

Data Source

PatentUS20240351976A1Novel preparation method for sarcosine and derivatives thereof
Publication Date: 2024.10.24
  • US20240351976A1 patent drawing
  • US20240351976A1 patent drawing
  • US20240351976A1 patent drawing

AI summary

The present invention relates to a preparation method for a sarcosinate including: step 1, reacting a solution of glyoxylic acid or a glyoxylate with an amine solution to prepare a Schiff base solution; step 2, subjecting the prepared Schiff base solution to a hydrogenation reaction under the condition of a catalyst; and step 3, adjusting a pH value of a solution obtained after the hydrogenation reaction to be alkaline to obtain the sarcosinate. Wherein the pH value of the solution obtained after the hydrogenation reaction in the step 3 is adjusted to be acidic to obtain sarcosine. Wherein a sarcosinate solution obtained in the step 3 is reacted with cyanamide to prepare a sarcosine derivative. A novel preparation method for sarcosine and derivatives thereof in the present invention solves the problem of using highly toxic chemicals as raw materials in the existing production process of sarcosine or sarcosine derivatives such as creatine, while the new process is simpler and more efficient, has lower production cost, and is of great significance.