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Method for co-producing 1,9-decadiene and 9-decen-1-alcohol in fixed bed reactor

A fixed-bed reactor, decadiene technology, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve the problems of difficult industrial production, expensive catalysts, complex reaction conditions, etc., and achieve convenient post-processing. , Avoid the use of expensive catalysts, the effect of high product purity

Active Publication Date: 2021-10-22
宁波永顺精细化工有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] 1. Patent US20140155666 reports: using unsaturated fatty acid 10-undecylenic acid as raw material, PdCl2(PPh3)2 as catalyst, decarboxylation reaction occurs, the yield of 1,9-decadiene is only 59%, and the catalyst is expensive, Complex production conditions
[0007] 2. Literature (Synthesis, 2012, 44(19): 3003-3005) reports: using dodecanedioic acid as raw material, PdCl2(PPh3)2 as catalyst, decarboxylation reaction occurs above 190°C, 1,9-decadiene Yield is only 55%, same as above-mentioned method, production cost is high, and reaction condition is complicated
LiAlH 4 As a reducing agent, it is expensive and difficult to realize industrial production

Method used

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  • Method for co-producing 1,9-decadiene and 9-decen-1-alcohol in fixed bed reactor
  • Method for co-producing 1,9-decadiene and 9-decen-1-alcohol in fixed bed reactor
  • Method for co-producing 1,9-decadiene and 9-decen-1-alcohol in fixed bed reactor

Examples

Experimental program
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Effect test

example 1

[0047] Example 1, a reaction device, such as figure 1 As shown, it includes a dripping device 1, a connecting pipe 2, a fixed bed reactor 3 and a collection container 4 connected in sequence from top to bottom;

[0048] The collection container 4 is provided with a spherical condensation pipe 41, and the effect of the spherical condensation pipe 41 is to condense the discharge of gas discharged from the bottom of the fixed bed reactor 3; the fixed bed reactor 3 is heated in parallel with electric coils, and the fixed bed reactor 3 is provided There is a thermocouple 31, and this thermocouple 31 is used to display the temperature in the fixed-bed reactor 3 in real time. The purpose of controlling the temperature in the fixed-bed reactor 3 is to realize the pyrolysis reaction of the esterification intermediate product.

[0049] A filler is arranged in the fixed bed reactor 3, and the filler is a glass Raschig ring filler with a particle size of 3±0.5mm.

[0050] The esterified...

Embodiment 1-1

[0061] Example 1-1, a fixed bed reactor mainly produces 1,9-decadiene and by-products 9-decen-1-ol, the following steps are carried out in sequence:

[0062] 1) Mix 34.8g (0.2mol) of 1,10-decanediol and 70.4g (0.8mol, 4eq) of isobutyric acid to form a reaction solution, put it in a 250mL reaction bottle, and raise the temperature to 150°C for esterification. The water evaporated from the esterification reaction is discharged in real time; after 4 hours of the esterification reaction, no more water is produced, and the temperature is raised to 200°C to evaporate the isobutyric acid, and the evaporated isobutyric acid is recovered; when the isobutyric acid is no longer evaporated , the temperature was lowered to room temperature to obtain an esterification intermediate;

[0063] 2), put the esterified intermediate product into the dripping device 1, and the esterified intermediate product is added dropwise (about 15g / h dropping speed) through the connecting pipe 2 and then added...

Embodiment 1-2～ Embodiment 1-6

[0068] Example 1-2~Example 1-6, a fixed bed reactor mainly produces 1,9-decadiene and a by-product 9-decen-1-ol method, changing the reaction of the esterification intermediate product in the fixed bed The reaction space velocity in device 3, the reaction temperature in fixed-bed reactor 3, all the other are equal to embodiment 1-1; Reaction parameter and obtained result are described in following table 1.

[0069] Table 1. Main production of 1,9-decadiene and by-product of 9-decen-1-ol

[0070]

[0071]

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Abstract

The invention discloses a method for co-producing 1,9-decadiene and 9-decene-1-alcohol in a fixed-bed reactor, which comprises the following steps in sequence: esterifying 1,10-decanediol and isobutyric acid reaction to obtain an esterification intermediate product; the esterification intermediate product enters the fixed bed reactor (3) in the form of dropwise to carry out the ester pyrolysis reaction, and adds an aqueous alkali solution to the collected reaction product, mixes it uniformly, and then leaves it to stand for stratification , to obtain an aqueous phase and an organic phase respectively, take the organic phase and carry out vacuum distillation to obtain 1,9-decadiene; mix the still liquid obtained by the above-mentioned vacuum distillation with the water phase, and heat up to reflux for hydrolysis reaction; hydrolysis The post-reaction product is post-treated to obtain by-product 9-decen-1-alcohol. By adopting the method of the present invention, the product ratio of 1,9-decadiene and 9-decene-1-alcohol can be selectively obtained by controlling the temperature of the reactor and the reaction space velocity.

Description

technical field [0001] The invention belongs to the field of chemical industry, and in particular relates to a method for synthesizing 1,9-decadiene and co-producing 9-decen-1-ol in a fixed-bed reactor. Background technique [0002] The structural formulas of 1,9-decadiene and 9-decen-1-ol are as follows: [0003] [0004] 1,9-Decadiene is an important fine chemical intermediate and is widely used in organic synthesis. [0005] At present, the synthesis process of 1,9-decadiene mainly includes the following types: [0006] 1. Patent US20140155666 reports: using unsaturated fatty acid 10-undecylenic acid as raw material, PdCl2(PPh3)2 as catalyst, decarboxylation reaction occurs, the yield of 1,9-decadiene is only 59%, and the catalyst is expensive, Production conditions are complex. [0007] 2. Literature (Synthesis, 2012, 44(19): 3003-3005) reports: using dodecanedioic acid as raw material, PdCl2(PPh3)2 as catalyst, decarboxylation reaction occurs above 190°C, 1,9-deca...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C29/09C07C33/025C07C1/213C07C11/12
CPCC07C1/213C07C29/095C07C67/08C07C67/297C07C33/025C07C11/12C07C69/28
Inventor 张小莲毛崇智韦隆武陈新发
Owner 宁波永顺精细化工有限公司
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