Dehydrolinalyl Acetate Production Without Catalyst
Find Innovative SolutionsGenerate Solutions
Solution Overview
Problem
Current processes for producing dehydrolinalyl acetate (DLA) through acetylation of dehydrolinalool (DLL) result in significant amounts of side products, which is undesirable for flavor and fragrance applications.
Innovation Solution
The production of DLA is achieved by reacting DLL with acetic anhydride in the absence of a catalyst at normal pressure and elevated temperatures, with a molar ratio of 1.1:1 to 5:1, typically without a solvent, and with a reaction time of 2 to 20 hours.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Productivity
If p-toluene sulfonic acid catalyst is used for acetylation of DLL, then the reaction proceeds efficiently, but significant amounts of side products are formed
Solution Approach 1:
The patent removes the catalyst (p-toluene sulfonic acid) from the reaction system entirely, performing the acetylation of dehydrolinalool without any catalytic assistance. This extraction of the harmful element (catalyst that causes side reactions) eliminates the formation of unwanted side products while still achieving the desired acetylation reaction through direct heating at elevated temperatures.
Solution Approach 2:
The patent changes the reaction parameters by using elevated temperatures (reflux conditions) without catalyst, altering the reaction pathway to favor the desired acetylation product while avoiding the side reactions that occur with catalytic conditions. This parameter change transforms the reaction conditions from catalyst-dependent to temperature-driven selectivity.
2Productivity
If microreactor under 30 bar pressure is used for acetylation, then DLA is produced, but the process requires high pressure equipment and complex conditions
Solution Approach 1:
The patent employs standard laboratory or industrial reaction equipment that operates at atmospheric pressure, replacing the need for expensive and complex high-pressure microreactor systems. The reaction proceeds efficiently under simple reflux conditions using conventional glassware or steel reactors, eliminating the need for specialized high-pressure equipment.
3Speed
If catalyst is used for acetylation reaction, then reaction rate is improved, but selectivity decreases and side products increase
Solution Approach 1:
The patent removes the catalyst from the reaction system, eliminating the source of poor selectivity and side product formation. The reaction proceeds without catalytic assistance, achieving both acceptable reaction rates through thermal activation and high selectivity for the desired dehydrolinalyl acetate product.
Solution Approach 2:
The patent changes the reaction conditions by using elevated temperature without catalyst, shifting the reaction mechanism from catalyst-mediated to thermally-driven acetylation. This parameter change maintains reasonable reaction kinetics while dramatically improving selectivity by avoiding the catalytic pathways that lead to side products.
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 significantly reduces the formation of side products, achieving excellent selectivity and yield of DLA, which can be used in flavor and fragrance applications or further processed into linalylacetate.
Implementation Method 1
The production of DLA is achieved by reacting DLL with acetic anhydride... by acetylation
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 more than 50°C, preferably more than 80°C, more preferably more than 100°C
Implementation Method 3
At the end of the reaction, the remaining acetate anhydride and the acetic acid (product of the process) is removed from the reaction solution. This is usually done by distillation (normal pressure or at a reduced pressure).
Data Source
AI summary
The present invention is related to a novel and improved process for the production of dehydrolinalyl acetate (DLA), which lUPAC name is acetic acid 1 -ethynyl-1,5- dimethyl-hex-4-enyl ester, starting from dehydrolinalool (DLL), which lUPAC name is 3,7-dimethyloct-6-en-1 -yn-3-ol, by acetylation.