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Farnesyl acetone and preparation method thereof

A technology of farnesyl acetone and farnesene, which is applied to the preparation of carbon-based compounds, carboxylic acid esters, chemical instruments and methods, etc., can solve the problems of low efficiency, cumbersome post-processing, not enough economical and environmental protection, and meet the reaction conditions Gentle, low-cost effect

Pending Publication Date: 2020-12-01
WUHAN HESHENG TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The traditional synthesis process mainly uses formaldehyde, acetone, etc. as raw materials to gradually extend the carbon chain. The disadvantage of this method is that it is not economical and environmentally friendly, and the efficiency is low.
CN105384615 describes the synthesis of farnesyl acetone with tertiary nerolidol under acid catalysis. The post-treatment of this method is relatively cumbersome and needs to be separated by distillation, and the yield is about 88%.

Method used

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  • Farnesyl acetone and preparation method thereof
  • Farnesyl acetone and preparation method thereof
  • Farnesyl acetone and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] Embodiment 1 provides a kind of using α-farnesene as raw material, prepares the method for farnesyl acetone, and this method comprises:

[0058] First, rhodium catalyzes the preparation of farnesyl acetonate, including: α-farnesene (10.3g, 98%) is placed in a 500ml reactor, and 100mL of ethanol, 20mL of deionized water, and triphenylphosphine are added to the system. Sodium trimetasulfonate (600mg) and bis(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate (50mg) were added to ethyl acetoacetate and heated to 100°C, and refluxed for 10h. Static layered filtration, the reaction solution was concentrated under reduced pressure, extracted with ethyl acetate, concentrated by distillation under reduced pressure to obtain 16.52 g of farnesylacetonate, and the yield of farnesylacetonate was determined by the above-mentioned gas chromatography to be 98.20%.

[0059] Wherein, the output of farnesyl acetonate is calculated and obtained by the following method:

[0060] The ...

Embodiment 2

[0066] Embodiment 2 provides a kind of method that takes α-farnesene as raw material to prepare farnesyl acetonate, in the process of preparing farnesyl acetonate with α-farnesene as raw material, utilize respectively in embodiment 2 and The different rhodium catalysts of embodiment 1 prepare farnesyl acetonate, and other used reaction conditions and raw materials are all identical with embodiment 1, and its experimental result is as shown in table 1 below.

[0067] The impact of different rhodium metal catalysts on the reaction of table 1

[0068]

[0069] It can be seen from the above experimental groups that the yield of farnesyl acetonate is at least 97% or more, and some even reach more than 98% by using different rhodium metal catalysts to prepare farnesyl acetonate.

Embodiment 3

[0071] Embodiment 3 provides a kind of method for preparing farnesyl acetonate with α-farnesene as raw material, in the process of preparing farnesyl acetonate with α-farnesene as raw material, studied respectively in embodiment 3 Catalyzed reaction at different temperatures was used to prepare farnesyl acetonate. Other reaction conditions and raw materials used were the same as in Example 1. The experimental results are shown in Table 2.

[0072] The impact of table 2 different temperatures on farnesyl acetonate output

[0073] Numbering Reaction temperature (°C) Yield of farnesyl acetonate (%) Experimental group 1 80 95.31 Experimental group 2 90 97.56 Experimental group 3 100 98.87 Experimental group 4 110 97.35 Experimental group 5 120 97.10

[0074] From the results of the above examples, it can be seen that in the process of preparing farnesylacetonate from α-farnesene, the yield of farnesylacetonate obtained is slight...

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Abstract

The invention relates to the field of chemical synthesis, in particular to farnesyl acetone and a preparation method thereof. The method comprises the following steps: carrying out a first contact reaction on alpha-farnesene, acetoacetate, an organic phosphine ligand and a metal catalyst to obtain farnesyl acetone ester; and carrying out a second contact reaction on the farnesyl acetone ester andwater or a metal salt aqueous solution to obtain farnesyl acetone. The farnesyl acetone prepared by the method is high in yield and purity, and the yield and the purity are both 98% or above.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and relates to a farnesylacetone and a preparation method thereof, in particular to a method for efficiently producing farnesylacetone by using α-farnesene as a substrate. Background technique [0002] In recent years, the demand for vitamin E has been increasing. Isophytol is an important raw material for the synthesis of vitamin E and vitamin K. The demand for farnesyl acetone, an intermediate of isophytol, is also increasing year by year. Farnesylacetone can be synthesized according to different starting substrates. The traditional synthesis process mainly uses formaldehyde, acetone, etc. as raw materials to gradually extend the carbon chain. The disadvantage of this method is that it is not economical and environmentally friendly, and its efficiency is low. CN105384615 describes the synthesis of farnesylacetone by using tertiary nerolidol under acid catalysis. The post-treatment of this met...

Claims

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Application Information

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IPC IPC(8): C07C45/65C07C49/203
CPCC07C45/65C07C67/343C07C49/203C07C69/738
Inventor 黄敏坚
Owner WUHAN HESHENG TECH CO LTD
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