Synthetic method of 1,9-decadiene

A synthesis method, the technology of decadiene, applied in the field of synthesis of 1,9-decadiene, can solve the problems of complex reaction conditions, high production cost, high reaction pressure, etc., and achieve good atom economy, fast reaction rate, cheap effect

Inactive Publication Date: 2016-01-20
ZHEJIANG UNIV
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  • Abstract
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  • Claims
  • Application Information

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Problems solved by technology

[0005] 1. Using the patent US20140155666 report: using unsaturated fatty acid 10-undecylenic acid as raw material, PdCl 2 (PPh 3 ) 2 As a catalyst, a decarboxylation reaction occurs, and the yield of 1,9-decadiene is only 59%, and the catalyst is expensive and the production conditions are complicated
[0006] 2. Using literature (Synthesis, 2012, 44(19): 3003-3005) report: using dodecanedioic acid as raw material, PdCl 2 (PPh 3 ) 2 As a catalyst, decarboxylation reaction occu

Method used

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  • Synthetic method of 1,9-decadiene

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Embodiment 1

[0036] Embodiment 1, a kind of synthetic method of 1,9-decadiene, carries out following steps successively:

[0037] 1), in the 250mL four-neck flask that is equipped with a thermometer, a 10cm rectification column with a condensing reflux device installed on the top, a stirring paddle, and a heating dropping funnel, add 128g (0.5mol) palmitic acid, and γ-Al 2 o 3 (about 15g) as a catalyst, the molar ratio of the two is 1:0.3. After the temperature was raised to 340° C., 1,10-decanediol was continuously fed in a dropwise manner to react. The output speed is 40g / h, and the feed rate is adjusted so that it is basically consistent with the output speed. Continuous reaction for 6 hours, feed 250g, discharge about 240g. The remaining mixed solution in the four-necked flask can continue to be used as bottom material for continuous reaction.

[0038] 2), stop the reaction, carry out normal pressure rectification on 240g of the discharged material, collect the 99±0.5°C fraction, s...

Embodiment 10

[0050] Embodiment 10, the palmitic acid (hexadecanoic acid) in embodiment 1 is changed into higher fatty acid as described in table 2, and molar weight is constant. The rest are equal to Example 1.

[0051] The yields of the obtained products are shown in Table 2 below.

[0052] Table 2

[0053] higher fatty acid

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Abstract

The invention discloses a synthetic method of 1,9-decadiene. The synthetic method comprises steps as follows: 1), higher aliphatic acid and a catalyst are uniformly stirred and mixed and then are heated to 340-360 DEG C, 1,10-decanediol is continuously dropwise fed, and continuous discharge is realized in a rectification mode; 2), a discharged material obtained in the step 1) is subjected to normal-pressure rectification, and 1,9-decadiene is obtained. The synthetic method further comprises a circular reaction in the step 3) as follows: bottom residues produced through normal-pressure rectification in the step 2) are mixed with 1,10-decanediol, a mixture replaces 1,10-decanediol in the step 1), a residual mixed solution formed after the reaction of the step 1) replaces a mixed bottom material in the step 1), and the circular reaction is performed according to the step 1). The method is adopted to synthesize 1,9-decadiene and has the characteristics of simple process, mild reaction conditions, low production cost, high reaction rate, high yield and the like.

Description

technical field [0001] The invention relates to a method for synthesizing organic compounds, in particular to a method for synthesizing 1,9-decadiene. Background technique [0002] 1,9-Decadiene, which has the formula C 10 h 18 , whose structural formula is shown in S-1, and the pure product is a colorless liquid. As an important organic intermediate, this compound is widely used in organic synthesis. [0003] [0004] At present, the synthesis methods of 1,9-decadiene mainly consist of the following types: [0005] 1. Using the patent US20140155666 report: using unsaturated fatty acid 10-undecylenic acid as raw material, PdCl 2 (PPh 3 ) 2 As a catalyst, a decarboxylation reaction occurs, and the yield of 1,9-decadiene is only 59%, and the catalyst is expensive and the production conditions are complicated. [0006] 2. Using literature (Synthesis, 2012, 44(19): 3003-3005) report: using dodecanedioic acid as raw material, PdCl 2 (PPh 3 ) 2 As a catalyst, the deca...

Claims

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Application Information

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IPC IPC(8): C07C11/12C07C1/20C07C1/213
Inventor 陈新志张恒钱超
Owner ZHEJIANG UNIV
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