Uracil Compound Methylation Using Methyl Chloride at Industrial Scale

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Solution Overview

Problem

Existing methods for synthesizing isoxazoline-containing uracil compounds using iodomethane are hindered by its high toxicity, volatility, high cost, environmental pollution, and the complexity of iodine recovery, making large-scale production challenging and requiring column chromatography for purification, which is difficult to implement industrially.

Innovation Solution

A methylation reaction using methyl chloride in a closed container with alkali, a catalyst, and an organic solvent at controlled pressure and temperature to produce isoxazoline-containing uracil compounds, avoiding iodomethane and column chromatography.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If iodomethane is used for methylation, then the reaction can proceed effectively, but the process becomes hazardous due to high toxicity and volatility

Engineering Contradiction:

Improvereaction effectivenessVSAvoidtoxicity and volatility

Core Design Contradiction:

ReliabilityVSObject-affected harmful factors

Solution Approach 1:

The patent replaces expensive, hazardous iodomethane with cheaper, safer methyl chloride. Although methyl chloride requires higher reaction temperature and pressure, it eliminates the severe toxicity and volatility issues of iodomethane, making the process safer and more cost-effective for industrial application

Inventive Principle:

Principle #27Cheap short-living objects (Disposable)

Solution Approach 2:

The patent changes the reaction parameters from ambient conditions (used with iodomethane) to elevated temperature (80-140°C) and pressure (0.5-2.0 MPa) to enable the use of methyl chloride, which has lower reactivity but much safer handling characteristics

Inventive Principle:

Principle #35Parameter changes

2Reliability

If iodomethane is used for methylation, then the reaction proceeds well, but the production cost increases significantly

Engineering Contradiction:

Improvereaction effectivenessVSAvoidproduction cost

Core Design Contradiction:

ReliabilityVSQuantity of substance

Solution Approach 1:

The patent substitutes expensive iodomethane with inexpensive methyl chloride, directly reducing raw material costs. The lower cost of methyl chloride makes large-scale production economically viable while maintaining acceptable reaction effectiveness through optimized conditions

Inventive Principle:

Principle #27Cheap short-living objects (Disposable)

3Reliability

If iodomethane is used for methylation, then the reaction works, but environmental pollution increases due to iodine-containing waste water

Engineering Contradiction:

Improvereaction effectivenessVSAvoidenvironmental pollution

Core Design Contradiction:

ReliabilityVSObject-generated harmful factors

Solution Approach 1:

The patent replaces iodomethane with methyl chloride, eliminating iodine-containing waste streams. Methyl chloride produces simpler, more easily treatable waste products, significantly reducing environmental pollution and simplifying waste water treatment requirements

Inventive Principle:

Principle #27Cheap short-living objects (Disposable)

4Manufacturing precision

If column chromatography is used for purification, then high-content product is obtained, but the process becomes difficult to implement industrially

Engineering Contradiction:

Improveproduct contentVSAvoidindustrial implementability

Core Design Contradiction:

Manufacturing precisionVSEase of manufacture

Solution Approach 1:

The patent performs preliminary optimization of reaction conditions (temperature, pressure, catalyst, solvent system) to maximize product selectivity and minimize by-products during the methylation step itself. This preliminary action reduces the need for complex post-reaction purification, enabling direct industrial production of high-content 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 reduces the use of hazardous chemicals, lowers production costs, and enables the production of high-content isoxazoline-containing uracil compounds suitable for industrial use without the need for additional purification steps.

Implementation Method 1

an isoxazoline-containing uracil compound shown by formula I is prepared by a methylation reaction of a compound shown by formula II with methyl chloride in a closed container in the presence of alkali, a catalyst and an organic solvent

Methodology Applied

Scientific EffectMethylation reaction: Chemical Bonding

Data Source

PatentUS12503462B2Method for preparing isoxazoline-containing uracil compound through methylation

Publication Date: 2025.12.23 JIANGSU YANGNONG CHEM CO LTD

AI summary

A method for preparing an isoxazoline-containing uracil compound involves methylation. An isoxazoline-containing uracil compound shown by formula I is prepared by a methylation reaction between a compound shown by formula II and methyl chloride in a closed container in the presence of alkali, a catalyst and an organic solvent; and a reaction equation is as follows: