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A kind of synthetic method of double bond capping compound

A synthesis method and compound technology, which is applied in the field of synthesis of double-bond-terminated compounds, can solve problems affecting reaction speed and product performance, low reaction conversion rate, and increased synthesis cost, so as to achieve simple and controllable synthesis process and high product yield High, short production cycle effect

Active Publication Date: 2022-04-22
WANHUA CHEM GRP CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in the process of alkoxide reaction, the alkali metallization reagent used will destroy the double bond of the raw material polyether at high temperature, and in the preparation of high-quality polyether modified silicone, it involves the end-capped unsaturated In the hydrosilylation reaction of polyether and hydrogen-containing silicone oil, the higher the double bond content of the polyether, the faster the reaction speed, and the better the performance of the prepared silicone; During the hydrogen addition reaction, it not only introduces the end-capped polyether impurities whose double bonds are destroyed, but also affects the reaction speed and product performance.
[0009] The common point of the above two types of methods is that both adopt the mode of equilibrium reaction to introduce double bonds to the substrate of a certain group. The disadvantage of adopting the mode of equilibrium reaction is that it has strong reversibility, and the reaction conversion rate of most of the reactions is low. The actual end-capping rate of the product is low (directly leading to the decline and instability of product quality) or requires more energy consumption to achieve the required end-capping rate, thereby increasing the synthesis cost

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] The substrate of this embodiment is ethylenediamine.

[0038] The following steps are adopted to prepare the double bond-terminated compound:

[0039] 1) In a three-necked 1000ml flask with stirring, thermometer and nitrogen atmosphere, first 120g ethylenediamine (substrate) is added in the reaction vessel;

[0040] Add 576g (the molar ratio of the active hydrogen in the substrate is 1:1) isobutane oxide (IBO), and carry out tertiary alcohol capping at a reaction temperature of 100°C and a reaction pressure of 0.15MPa for 1h; the theoretical hydroxyl value of the product is 644.83 mgKOH / g, the measured value of the hydroxyl value of the tertiary alcohol-capped product obtained in this step is 644.8 mgKOH / g, basically achieving in-situ conversion.

[0041] 2) The intermediate (tertiary alcohol end-capped product) prepared by step 1) was treated with 0.5h -1 The mass space velocity passes through a fixed bed with a reaction temperature of 80°C (filled with a solid heter...

Embodiment 2

[0046] The substrate of this example is trimethylolpropane.

[0047] The following steps are adopted to prepare the double bond-terminated compound:

[0048] 1) In a three-necked 1000ml flask with stirring, thermometer and nitrogen atmosphere, earlier 268g trimethylolpropane (substrate) is added in the reaction vessel, add 0.536g (0.2% of the substrate quality) sodium methylate, Contact at a reaction temperature of 120°C and a pressure of -0.097MPa for 2 hours, and dehydrate under reduced pressure;

[0049] Add 648g (molar ratio of IBO to active hydrogen in the substrate: 1.5:1) isobutane oxide (IBO), and carry out tertiary alcohol capping at a reaction temperature of 150°C and a reaction pressure of 0.2MPa for 10h;

[0050] The theoretical hydroxyl value of the product is 500.89 mgKOH / g, and the measured hydroxyl value of the tertiary alcohol-capped product obtained in this step is 501 mgKOH / g, basically achieving in-situ transformation.

[0051] 2) The intermediate (tertia...

Embodiment 3

[0055] The substrate of this example is ethanolamine.

[0056] The following steps are adopted to prepare the double bond-terminated compound:

[0057] 1) In a three-necked 1000ml flask with stirring, thermometer and nitrogen atmosphere, first 184g ethanolamine (substrate) is added in the reaction vessel, add 0.18g (0.1% of the substrate quality) sodium hydroxide, at reaction temperature 100°C, contact at -0.1MPa for 3 hours, dehydration under reduced pressure;

[0058] Add 345.6g (the molar ratio of IBO to active hydrogen in the substrate is 1.2:1) isobutane oxide (IBO), and carry out tertiary alcohol capping at a reaction temperature of 125°C and a reaction pressure of 0.4MPa for 7h;

[0059] The theoretical hydroxyl value of the product is 578.35 mgKOH / g, and the measured hydroxyl value of the tertiary alcohol-capped product obtained in this step is 578.4 mgKOH / g, basically achieving in-situ conversion.

[0060] 2) The intermediate (tertiary alcohol end-capped product) pr...

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Abstract

The present invention provides a kind of synthetic method of double-bond-terminated compound, and described synthetic method comprises the following steps: 1) take the compound that has active hydrogen-containing group on primary carbon and / or secondary carbon position as substrate, the substrate tertiary alcohol end-capped product; 2) the tertiary alcohol end-capped product undergoes intramolecular dehydration under the action of a Lewis acid catalyst to obtain a double-bond end-capped product . The synthesis method of the invention can increase the double-bond end-capping rate, and the synthesis process is simple and controllable, and is environmentally friendly.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a synthesis method of a double-bond-terminated compound. Background technique [0002] The double-bond-terminated compound can be used in the synthesis and application fields of unsaturated polyester, unsaturated polyether, polyether amine and their modification, graft epoxidation, etc. For example, advanced organic reaction intermediates for carbon chain growth, polyurethane foaming silicone oil, double bond end-capping modification of surfactant fatty alcohol, fluorine-silicon modified polymer precursors, etc. Its application fields such as: can be used to prepare pharmaceutical intermediates, epoxy resin, epoxy resin / polyurethane / polyacrylate and other polymer alloys, or IPN, photocurable resin, modified resin (silicon modified, fluorine modified, etc. ) and grafted surfactants, etc. [0003] The synthesis method of double bond end-capping is applied to pharmaceutical interm...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C209/68C07C211/21C07C41/18C07C43/15C07C213/08C07C215/08
CPCC07C209/68C07C213/04C07C41/03C07C41/18C07C213/08C07C211/21C07C215/14C07C43/135C07C43/15C07C43/13C07C215/08C07C215/12
Inventor 叶天陈海波信勇刘运海鞠昌迅王竞辉张琴花刘斌黎源
Owner WANHUA CHEM GRP CO LTD