C17 Alcohol Esterification for Low-Color Methacrylates

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Solution Overview

Problem

Current methods do not effectively produce (meth)acrylates from C 17 alcohol mixtures with a controlled average degree of branching, leading to high yields and purities, and result in products with low color numbers, as existing processes primarily focus on C 16, C 18, and C 20 alkyl (meth)acrylates.

Innovation Solution

A process involving the esterification of (meth)acrylic acid with a C 17 alcohol mixture using an acidic catalyst and polymerization inhibitor in the presence of a solvent forming an azeotrope with water, conducted in a reactor with a circulation evaporator, where the C 17 alcohol mixture has an average degree of branching of 3.01 to 3.5 and a solvent content of at least 95% by weight, ensuring the (meth)acrylates have a solidification point below 0 °C.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Manufacturing precision

If esterification is performed with C 17 alcohol mixtures using conventional methods, then production of (meth)acrylates is achieved, but the average degree of branching becomes excessively high (above 3.5)

Engineering Contradiction:
Improveaverage degree of branchingVSAvoidcontrol of branching degree
Core Design Contradiction:
Manufacturing precisionVSDifficulty of detecting and measuring

Solution Approach 1:

The patent applies parameter changes by strictly controlling the average degree of branching of the C 17 alcohol mixture within the range of 3.01 to 3.5. This is achieved by selecting specific alcohol mixtures with controlled iso-index values and maintaining this parameter throughout the esterification process to prevent excessive branching in the final (meth)acrylate product.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent implements preliminary action by pre-selecting and characterizing the C 17 alcohol mixture before esterification, ensuring it has the required average degree of branching (iso-index of 3.01 to 3.5). This preliminary characterization and selection of raw materials with controlled properties prevents the formation of excessively branched products during the esterification reaction.

Inventive Principle:
Principle #10Preliminary action

2Productivity

If conventional esterification processes are used, then (meth)acrylates are produced, but yields and purities are insufficient

Engineering Contradiction:
Improveyield and purityVSAvoidprocess simplicity
Core Design Contradiction:
ProductivityVSEase of manufacture

Solution Approach 1:

The patent uses an acidic catalyst as an intermediary to facilitate the esterification reaction between (meth)acrylic acid and C 17 alcohol mixture. The catalyst accelerates the reaction and improves both yield and purity of the (meth)acrylate product, making the manufacturing process more efficient while maintaining reasonable simplicity.

Inventive Principle:
Principle #24Intermediary (Mediator)

Solution Approach 2:

The patent applies extraction by removing water from the esterification reaction system, likely through azeotropic distillation or similar water removal techniques. This drives the equilibrium toward product formation, thereby improving both yield and purity of the (meth)acrylate while maintaining process simplicity.

Inventive Principle:
Principle #2Taking out (Extraction)

3Object-affected harmful factors

If existing processes are applied, then (meth)acrylates are produced, but color numbers are high

Engineering Contradiction:
Improvecolor numberVSAvoidproduct quality
Core Design Contradiction:
Object-affected harmful factorsVSProductivity

Solution Approach 1:

The patent converts the potential harm of side reactions and impurity formation during esterification into benefit by carefully controlling reaction conditions, using appropriate catalysts, and managing the process to minimize discoloration. This results in high-quality (meth)acrylates with low color numbers while maintaining good productivity.

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 process achieves high-purity, high-yield (meth)acrylates with a controlled degree of branching, resulting in products with a low solidification point and minimal color, suitable for various technical applications as monomers and comonomers for polymer production.

Implementation Method 1

in the presence of a solvent which forms an azeotrope with water, the esterification being carried out in a reactor with a circulation evaporator, the azeotrope being distilled off and condensed

Methodology Applied
Scientific EffectAzeotrope formation:

Implementation Method 2

the azeotrope being distilled off and condensed

Methodology Applied
Scientific EffectDistillation: Distillation

Implementation Method 3

the azeotrope being distilled off and condensed

Methodology Applied
Scientific EffectCondensation: Condensation

Implementation Method 4

the condensate decomposing into an aqueous and an organic phase

Methodology Applied
Scientific EffectPhase separation:

Data Source

PatentEP2504308B1Process for the production of (METH)acrylates of c17-alcohol mixtures
Publication Date: 2021.05.19 BASF SE
  • EP2504308B1 patent drawing

AI summary

The invention relates to a method for producing (meth)acrylates of C17 alcohol mixtures by means of converting (meth)acrylic acid with a C17 alcohol mixture in the presence of at least one acidic catalyst and at least one polymerization inhibitor and in the presence of a solvent forming an azeotrope with water, in which the esterification is performed in a reactor having a circulation evaporator, the azeotrope is distilled out and condensed, the condensate degrades into an aqueous and an organic phase, wherein the C17 alcohol mixture comprises an average branching level (iso index) of 2.8 to 3.7.