AMPS Production via Isobutylene Impurity Control

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Solution Overview

Problem

Current production methods for 2-acrylamido-2-methylpropane sulfonic acid involve complex and burdensome purification steps, often requiring difficult-to-handle solvents and resulting in low yields and impurities that affect polymerization and molecular weight, with impurities like butene and butadiene in isobutylene not being adequately considered.

Innovation Solution

A process involving co-reaction of acrylonitrile, fuming sulfuric acid, and isobutylene with controlled butene and butadiene content less than 1000 ppm, where acrylonitrile acts as both solvent and reagent, allowing for high purity 2-acrylamido-2-methylpropane sulfonic acid production through controlled reaction conditions and subsequent separation and drying, enabling high purity without complex purification steps.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Manufacturing precision

If complex purification methods (recrystallization from water or acetic acid) are used to obtain high purity 2-acrylamido-2-methylpropane sulfonic acid, then product purity is improved, but process complexity and operational burden increase significantly

Engineering Contradiction:
Improveproduct purityVSAvoidprocess complexity
Core Design Contradiction:
Manufacturing precisionVSDevice complexity

Solution Approach 1:

The invention performs preliminary action by strictly controlling the purity of isobutylene feedstock before the reaction occurs. By ensuring isobutylene contains less than 100 ppm of butene and butadiene impurities at the start of the process, the subsequent reaction inherently produces high purity AMPS without requiring complex purification steps. This prevents impurity formation rather than requiring elaborate removal procedures.

Inventive Principle:
Principle #10Preliminary action

Solution Approach 2:

The invention takes out the complex purification steps (recrystallization from water or acetic acid with multiple dissolution/cooling cycles) from the process entirely. By using pure isobutylene feedstock, the reaction directly yields high purity product that can be separated by simple filtration and drying, eliminating the need for burdensome extraction and recrystallization operations.

Inventive Principle:
Principle #2Taking out (Extraction)

2Manufacturing precision

If recrystallization from water is used to purify 2-acrylamido-2-methylpropane sulfonic acid, then product purity is improved, but yield decreases due to high water solubility

Engineering Contradiction:
Improveproduct purityVSAvoidyield
Core Design Contradiction:
Manufacturing precisionVSProductivity

Solution Approach 1:

The invention performs preliminary action by controlling impurity levels in the isobutylene feedstock before reaction. This prevents the formation of impurities that would otherwise require removal through lossy purification steps, thereby maintaining both high purity and high yield without the need for water recrystallization.

Inventive Principle:
Principle #10Preliminary action

Solution Approach 2:

The invention converts the potential harm of impurity formation into a benefit by using ultra-pure isobutylene feedstock. The strict purity requirements for the starting material act as a blessing in disguise, preventing impurity formation and eliminating the need for yield-reducing purification steps, thus achieving both high purity and high yield simultaneously.

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

3Manufacturing precision

If multiple dissolution and cooling steps are used for purification, then product purity is improved, but processing time and operational burden increase

Engineering Contradiction:
Improveproduct purityVSAvoidprocessing time
Core Design Contradiction:
Manufacturing precisionVSLoss of time

Solution Approach 1:

The invention performs preliminary action by ensuring isobutylene feedstock has less than 100 ppm of butene and butadiene impurities before the reaction. This preliminary purity control prevents impurity formation during reaction, eliminating the need for multiple time-consuming dissolution and cooling purification steps.

Inventive Principle:
Principle #10Preliminary action

Solution Approach 2:

The invention takes out the multiple dissolution and cooling purification steps from the process entirely. By controlling feedstock purity upfront, the process achieves high purity product through simple reaction, filtration, and drying operations, saving significant processing time and operational effort.

Inventive Principle:
Principle #2Taking out (Extraction)

4Productivity

If acrylonitrile is used in excess as reaction solvent, then reaction efficiency is improved, but product separation and purification become more difficult

Engineering Contradiction:
Improvereaction efficiencyVSAvoidseparation complexity
Core Design Contradiction:
ProductivityVSDevice complexity

Solution Approach 1:

The invention performs preliminary action by controlling isobutylene feedstock purity to less than 100 ppm impurities. This prevents impurity formation that would complicate separation, allowing the use of excess acrylonitrile as solvent for reaction efficiency while maintaining simple product separation through filtration and drying.

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

The process achieves high purity 2-acrylamido-2-methylpropane sulfonic acid with greater than 99% purity and simplifies the production by controlling isobutylene impurities, reducing the need for burdensome purification methods and improving polymerization outcomes.

Implementation Method 1

co-reacting acrylonitrile, fuming sulfuric acid and isobutylene

Methodology Applied
Scientific EffectChemical reaction: Chemical Bonding

Implementation Method 2

the reaction product takes the form of crystals suspended in the reaction solvent

Methodology Applied
Scientific EffectCrystallization: Crystallisation

Implementation Method 3

2-Acrylamido-2-methylpropane sulfonic acid is subsequently separated from the acrylonitrile, generally by filtration

Methodology Applied
Scientific EffectFiltration: Filter (physical)

Implementation Method 4

can later be purified by several known methods

Methodology Applied
Scientific EffectDrying: Evaporation

Data Source

PatentUS10662149B2Method for producing the 2-acrylamido-2-methylpropane sulfonic acid monomer and polymer comprising said monomer
Publication Date: 2020.05.26 S P C M SA
  • US10662149B2 patent drawing

AI summary

The invention relates to a method for producing 2-acrylamido-2-methylpropane sulfonic acid. Said method consists in reacting together acrylonitrile, fuming sulfuric acid and isobutylene. It is characterized in that the isobutylene contains less than 1000 ppm of butadiene and less than 1000 ppm of butene.