Dehydrolinalyl Acetate Production Catalyst Selectivity

Resolve Bottlenecks,
Find Innovative SolutionsGenerate Solutions

Solution Overview

Problem

Current methods for producing dehydrolinalyl acetate (DLA) through catalytic acetylation of dehydrolinalool (DLL) result in significant amounts of side products, which reduces the efficiency and yield of the process.

Innovation Solution

The use of specific catalysts, such as scandium or zinc trifluoromethanesulfonate, in the acetylation of DLL with acetic anhydride at elevated temperatures and normal pressures, with minimal catalyst amounts and without solvents, significantly reduces the formation of side products and enhances selectivity and yield.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If p-toluene sulfonic acid is used as catalyst for acetylation of DLL, then the reaction proceeds, but significant amounts of side products are formed

Engineering Contradiction:

Improvereaction efficiencyVSAvoidselectivity

Core Design Contradiction:

ProductivityVSManufacturing precision

Solution Approach 1:

The patent changes the chemical parameters of the catalyst system by replacing p-toluene sulfonic acid with alternative catalysts (scandium trifluoromethanesulfonate, zinc trifluoromethanesulfonate, or boron trifluoride etherate). This parameter change in catalyst identity and properties resolves the contradiction by achieving both acceptable reaction progression and significantly improved selectivity, reducing side product formation while maintaining productivity.

Inventive Principle:

Principle #35Parameter changes

2Ease of manufacture

If conventional catalysts are used for acetylation, then the process is simple, but side product formation reduces yield

Engineering Contradiction:

Improveprocess simplicityVSAvoidside product loss

Core Design Contradiction:

Ease of manufactureVSLoss of substance

Solution Approach 1:

The patent modifies the catalyst parameter from conventional organic-soluble acid catalysts to specific metal-based catalysts (scandium, zinc, or boron compounds). This parameter change maintains process simplicity while dramatically reducing side product formation and material loss, achieving both ease of manufacture and improved yield through the same catalytic system.

Inventive Principle:

Principle #35Parameter changes

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 approach results in a process with lower side product formation, achieving high selectivity and yield, as demonstrated by examples showing high conversion and yield rates with scandium and zinc trifluoromethanesulfonate catalysts, while other tested catalysts fail to replicate these results.

Implementation Method 1

The use of specific catalysts, such as scandium or zinc trifluoromethanesulfonate, in the acetylation of DLL with acetic anhydride

Methodology Applied

Scientific EffectCatalysis: Catalysis

Implementation Method 2

The process according to the present invention is usually carried out at elevated temperatures. Preferably the process according to the present invention is carried out at a temperature of 30 - 70 °C

Methodology Applied

Scientific EffectHeating: Heating

Data Source

PatentEP2994449B1Process of production of dehydrolinalyl acetate (i)

Publication Date: 2017.06.21 DSM IP ASSETS BV

AI summary

The present invention is related to a novel and improved process for the production of dehydrolinalyl acetate (DLA), which IUPAC name is acetic acid 1-ethynyl-1,5- dimethyl-hex-4-enyl ester, starting from dehydrolinalool (DLL), which IUPAC name is 3,7-dimethyloct-6-en-1-yn-3-ol, by catalytic acetylation.