3,7-Dimethyl-1-octen-3-ol Synthesis via Solvent-Free Ethynylation
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Solution Overview
Problem
Existing processes for producing 3,7-dimethyl-1-octen-3-ol (DMOE) are economically inefficient, require expensive catalysts, and result in low yields due to the use of stoichiometric amounts of ethynylation agents and solvents, which can impact flavor and fragrance applications.
Innovation Solution
A process involving the hydrogenation of 6-methyl-5-hepten-2-on to 6-methyl-2-heptanone using a palladium-containing catalyst, followed by reaction with acetylene in the presence of ammonia and potassium hydroxide without organic solvents, and subsequent hydrogenation of 3,7-dimethyl-1-octin-3-ol using a palladium catalyst on various carriers, including calcium carbonate, aluminum oxide, and silica, without organic solvents.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Ease of manufacture
If existing processes use stoichiometric amounts of ethynylation agents and solvents, then the reaction can proceed, but the manufacturing cost increases and product quality deteriorates
Solution Approach 1:
The patent removes organic solvents from the reaction system entirely, performing ethynylation and hydrogenation in neat conditions or with minimal water-soluble solvents. This extraction of harmful solvent components eliminates their negative impact on product quality while reducing manufacturing costs associated with solvent purchase, handling, and disposal.
Solution Approach 2:
The patent changes the physical state and composition parameters of the reaction medium by eliminating organic solvents and using alternative conditions (neat reactions or aqueous systems). This parameter change reduces both cost and harmful effects simultaneously by modifying the fundamental reaction environment rather than working within traditional solvent-based constraints.
2Productivity
If expensive catalysts like Pt are used for hydrogenation, then reaction efficiency improves, but manufacturing cost increases
Solution Approach 1:
The patent employs less expensive catalyst systems that can be used effectively for the required reaction duration without needing the premium performance of platinum. By accepting catalysts with shorter effective lifetimes or lower intrinsic activity, the process achieves cost reduction while maintaining sufficient productivity through optimized reaction conditions and catalyst loading.
Solution Approach 2:
The patent modifies catalyst-related parameters including metal type, support material, catalyst loading, and reaction conditions (temperature, pressure, solvent environment) to achieve effective hydrogenation without requiring expensive platinum catalysts. These parameter changes enable the use of more economical catalyst systems that maintain adequate productivity.
3Reliability
If stoichiometric amounts of ethynylation agents are used, then complete reaction occurs, but material waste increases
Solution Approach 1:
The patent changes the reaction parameters including stoichiometry, temperature, pressure, and catalyst system to improve reaction efficiency and selectivity. By optimizing these parameters, the process achieves high conversion and selectivity with better atom economy, reducing material waste while ensuring reliable reaction completion.
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 selectivity (>90%) and conversion (>95%) without the need for expensive catalysts or solvents, making it economically viable for industrial production and preserving the quality of the final product for fragrance applications.
Implementation Method 1
hydrogenation of 6-methyl-5-hepten-2-on to 6-methyl-2-heptanone using a palladium-containing catalyst
Implementation Method 2
in the presence of hydrogen and a palladium containing catalyst on a carrier
Implementation Method 3
hydrogenation of 3,7-dimethyl-1-octin-3-ol to 3,7-dimethyl-1-octen-3-ol in the presence of hydrogen and a palladium containing catalyst on a carrier
Implementation Method 4
with the proviso that the catalyst additionally contains lead when the carrier is calcium carbonate
Data Source
AI summary
The present invention is directed to a process for the manufacture of 3,7-dimethyl-1-octen-3-ol comprising the following steps:a) hydrogenation of 6-methyl-5-hepten-2-on to 6-methyl-2-heptanon in the presence of hydrogen and a palladium containing catalyst on a carrier selected from the group consisting of carbon, calcium carbonate and aluminum oxide.b) reaction of 6-methyl-2-heptanon with acetylene to 3,7-dimethyl-1-octin-3-ol in the presence of ammonia and potassium hydroxide and in the absence of any additional organic solvent;c) hydrogenation of 3,7-dimethyl-1-octin-3-ol to 3,7-dimethyl-1-octen-3-ol in the presence of hydrogen and a palladium containing catalyst on a carrier selected from the group consisting of calcium carbonate, aluminum oxide, silica, porous glass, carbon or graphite, and barium sulphate, with the proviso that the catalyst additionally contains lead when the carrier is calcium carbonate.The present invention is further directed to a process for the manufacture of isophytol and vitamin E, where a thus produced 3,7-dimethyl-1-octen-3-ol is used as starting material.