Method for synthesizing 1,9-decadiene

A synthesis method and technology of decadiene are applied in the field of preparation of organic compound 1,9-decadiene, can solve the problems of expensive catalyst, complex reaction conditions, large amount of catalyst, etc., and achieve good industrial application value and product purity The effect of high and high utilization rate of raw materials

Inactive Publication Date: 2019-06-14
ZHEJIANG UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] 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
[0005] 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 occurs above 190 ° C, and the yield of 1,9-decadiene is only 55%. Like the above method, the production cost is high and the reaction conditions are complicated
This method uses a large amount of catalyst, resulting in solid waste, and the reaction temperature is relatively high (temperature is 340-360°C)
CN 105254464 adopts the raw material 1,10-decanediol to be continuously fed and continuously discharged in the form of rectification, and the yield can only reach 87%, but the operation is cumbersome

Method used

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  • Method for synthesizing 1,9-decadiene
  • Method for synthesizing 1,9-decadiene
  • Method for synthesizing 1,9-decadiene

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

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

[0037] (1), after mixing 34.8g (0.2mol) 1,10-decanediol, 48.0g (0.8mol, 4eq) glacial acetic acid and 3.5g ferric chloride, place it in a 250mL reaction flask as a reaction solution, and heat up to 120°C, carry out esterification reaction and distill water, collect water through collection bottle 1;

[0038] (2) After 3 hours of esterification reaction, no more water will come out, continue to heat up to 350°C, steam the mixture of 1,9-decadiene and acetic acid, continue to discharge for 8 hours (that is, the reaction time is 8 hours), and pass through the collection bottle 2. Collect the mixed solution of 1,9-decadiene and acetic acid;

[0039] (3), remove the acetic acid (117°C) from the discharge (1,9-decadiene and acetic acid mixture) obtained in step (2) under normal pressure, then carry out vacuum distillation, collect 68±0.5°C (20Torr ) fraction to obtain 22.1g...

Embodiment 2

[0043] Embodiment 2, a kind of synthetic method of 1,9-decadiene, carry out following steps successively:

[0044] 1) Mix 34.8g (0.2mol) of 1,10-decanediol, 59.2g (0.8mol, 4eq) of propionic acid and 3.5g of copper sulfate and place it in a 250mL reaction flask as a reaction solution, heat up to 140°C, Carry out esterification reaction and steam out water, collect water by collecting bottle 1;

[0045] (2) After 4 hours of esterification until no more water comes out, continue to heat up to 340°C, steam the mixture of 1,9-decadiene and propionic acid, continue discharging for 8 hours, and collect 1,9- A mixture of decadiene and acetic acid;

[0046] (3) Distill propionic acid (141°C) from the output obtained in step (2) under normal pressure, and then conduct vacuum distillation to collect fractions at 68±0.5°C (20 Torr) to obtain 1,9-decadiene product 21.5 g (purity is 99.2%), yield is 78%;

[0047] (4), cyclic reaction:

[0048] After the step (2) is completed, the solid-...

Embodiment 3

[0050]Embodiment 3, a kind of synthetic method of 1,9-decadiene, carries out following steps successively:

[0051] (1), after mixing 34.8g (0.2mol) 1,10-decanediol, 73.2g (0.6mol, 3eq) benzoic acid and 3.5g ferric chloride, place it in a 250mL reaction flask as a reaction solution, and heat up to 180°C, carry out esterification reaction and distill out water, and collect water through collection bottle 1;

[0052] (2) After 3 hours of esterification until no more water comes out, continue to heat up to 330°C, steam the mixture of 1,9-decadiene and benzoic acid, continue to discharge for 8 hours, and collect 1,9- A mixture of decadiene and acetic acid;

[0053] (3), the discharge obtained in step (2) is subjected to vacuum distillation, and the fraction at 68±0.5°C (20 Torr) is collected, and the still liquid is a benzoic acid solution to obtain 22.6g of 1,9-decadiene product (purity is 99.3 %), the yield is 82%;

[0054] (4), cyclic reaction:

[0055] After the step (2) i...

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Abstract

The invention discloses a method for synthesizing 1,9-decadiene. The method sequentially comprises the following steps: adding carboxylic acid and 1,10-decadienol into a reaction container, heating the container until the 1,10-decadienol is dissolved, adding a catalyst, carrying out an esterification reaction at 120-200 DEG C, and collecting water evaporated in the esterification reaction; continuously heating the container to 300-350 DEG C after no water is produced in the esterification reaction, carrying out a reaction for 5-8 h, and evaporating and collecting a mixed solution of 1,9-decadiene and carboxylic acid; and respectively post-processing the mixed of 1,9-decadiene and carboxylic acid to obtain carboxylic acid and 1,9-decadiene respectively. The method for preparing 1,9-decadiene is efficient, economical and green, and meets industrial production requirements.

Description

technical field [0001] The invention belongs to the field of chemical industry, and in particular relates to a preparation method of organic compound 1,9-decadiene. Background technique [0002] 1,9-Decadiene is an important fine chemical intermediate, its structural formula is It is widely used in organic synthesis. [0003] At present, the synthesis process of 1,9-decadiene mainly includes the following types: [0004] 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. [0005] 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 decarboxylation reaction occurs above 190°C, and the yield of 1,9-decadiene is only 55%. Like the above m...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C1/213C07C11/12
Inventor 陈新志毛崇智钱超
Owner ZHEJIANG UNIV
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