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Method for preparing di-tert-butyl dicarbonate

A technology of di-tert-butyl ester and dicarbonic acid, which is applied in the field of amino acid protective agent preparation, can solve the problems of difficult industrial production, complex process operation, expensive use, etc., and achieve low production cost, high catalytic reaction yield and stable product quality Effect

Active Publication Date: 2014-02-12
GENCHEM & GENPHARM CHANGZHOU CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the method guides the yield to reach 76-89%, it uses an expensive crown ether catalyst, and the added water-soluble solvent tert-butanol and THF need to be washed with a lot of water to wash away from the organic phase
The process operation is complex, the amount of waste water is large, and industrial production is difficult

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] The preparation method of di-tert-butyl dicarbonate consists of the following steps:

[0029] Sodium tert-butoxide and n-hexane are put into the reactor, under N 2 Under gas protection, the temperature was raised to dissolve completely, then stirred and cooled to 5°C, and after passing carbon dioxide into the reaction kettle to saturation, a three-way catalyst was added to the reaction liquid, and the temperature in the reaction kettle was controlled within the range of -12°C. After 0.5 hours, put solid phosgene into the reactor in 10 batches, and then react for 3 hours after the input is completed. After the reaction is completed, add water to wash, evaporate the n-hexane solvent under normal pressure, and obtain the crude product of di-tert-butyl dicarbonate. The following crystallization is carried out, and after the crystallization is sufficient, the mother liquor is centrifuged to obtain the required di-tert-butyl dicarbonate;

[0030] The weight ratio of describe...

Embodiment 2

[0039] The preparation method of di-tert-butyl dicarbonate consists of the following steps:

[0040] Sodium tert-butoxide and n-hexane are put into the reactor, under N 2 Under gas protection, the temperature was raised to dissolve completely, then stirred and cooled to 10°C, and after passing carbon dioxide into the reaction kettle to saturation, a three-way catalyst was added to the reaction liquid, and the temperature in the reaction kettle was controlled within the range of 0°C, every 0.5 Hours, put solid phosgene into the reactor in 10 batches, and then react for 3 hours after the input is completed. After the reaction is completed, add water to wash, evaporate the n-hexane solvent under normal pressure, and obtain the crude product of di-tert-butyl dicarbonate. Carry out crystallization, after the crystallization is sufficient, centrifuge and separate the mother liquor to obtain the required di-tert-butyl dicarbonate;

[0041] The weight ratio of described sodium tert-b...

Embodiment 3

[0050] The preparation method of di-tert-butyl dicarbonate consists of the following steps:

[0051] Sodium tert-butoxide and n-hexane are put into the reactor, under N 2 Under gas protection, heat up to dissolve completely, then stir and cool to 15°C, and after passing carbon dioxide into the reaction kettle to saturation, add a three-way catalyst to the reaction solution, control the temperature in the reaction kettle within the range of 20°C, and every 0.5 hours, put solid phosgene into the reaction kettle in 10 batches, and then react for 3 hours after the input is completed. Carry out crystallization, after the crystallization is sufficient, centrifuge and separate the mother liquor to obtain the required di-tert-butyl dicarbonate;

[0052] The weight ratio of described sodium tert-butoxide to normal hexane is 1: 7;

[0053]The weight ratio of described solid phosgene to sodium tert-butoxide is 0.57: 1.0;

[0054] The weight ratio of the amount of water added and sodiu...

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Abstract

The invention discloses a method for preparing di-tert-butyl dicarbonate. The method comprises the steps of: adding sodium tert-butoxide and normal hexane in a reaction kettle, heating until the sodium tert-butoxide and the normal hexane resolve completely under the protection of N2, stirring and cooling to 0 to 50 DEG C; after introducing carbon dioxide into the reaction kettle until satiation, adding a three way catalyst into the liquid reactant; controlling the internal temperature of the reaction kettle to a range from minus 12 DEG C to 20 DEG C; adding solid carbonyl chloride into the reaction kettle for 10 times every 0.5 hour, and reacting for 3 hours after adding is finished; after reacting, adding water and washing, and vaporizing the normal hexane solvent off under normal pressure to obtain a crude product of di-tert-butyl dicarbonate; and crystallizing at the temperature of below 0 DEG C, and centrifugalizing the mother liquid after crystallizing is finished completely so as to obtain the required di-tert-butyl dicarbonate.

Description

technical field [0001] The invention relates to the technical field of preparation of amino acid protecting agents, in particular to a preparation method of di-tert-butyl dicarbonate. Background technique [0002] Di-tert-butyl dicarbonate (hereinafter referred to as DiBoc) is an important amino acid protective agent and plays an important role in peptide synthesis. DiBoc has the advantages of low price, good reactivity, and simple post-treatment. The by-products of the reaction are carbon dioxide and tert-butanol, which will not cause new pollution. Therefore, it is widely used in the synthesis of amino acids, proteins, and peptides. [0003] The industrial preparation of DiBoc guided by the literature mainly adopts the sodium alkoxide method. Its reaction formula is as follows: [0004] Japanese patent JP flat 4-356445 discloses a kind of synthetic method of DiBoc, adopts sodium butoxide as raw material, n-hexane is solvent, introduces CO 2 Finally, add 1,4-diazocycloo...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C69/96C07C68/04
CPCY02P20/141
Inventor 王玉琴詹玉俊
Owner GENCHEM & GENPHARM CHANGZHOU CO LTD
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