Barium sulfonate catalyst and application thereof in synthesis of D,L-P-hydroxyphenyl hydantoin

A technology of p-hydroxyphenylhydantoin and catalysts, which is applied in the field of catalysts and its applications, can solve the problems of difficult reuse of catalysts and low purity, and achieve the effects of fast synthesis rate, low reaction temperature, and lower reaction temperature

Active Publication Date: 2014-12-03
LULIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the purity of the D,L-p-hydroxyphenylhydantoin product obtained from the reaction is relatively low, and about 5% of racemic p-hydroxyphenylglycine that is difficult to resolve is mixed in the product; in addition, the catalyst is difficult to reuse

Method used

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  • Barium sulfonate catalyst and application thereof in synthesis of D,L-P-hydroxyphenyl hydantoin
  • Barium sulfonate catalyst and application thereof in synthesis of D,L-P-hydroxyphenyl hydantoin
  • Barium sulfonate catalyst and application thereof in synthesis of D,L-P-hydroxyphenyl hydantoin

Examples

Experimental program
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Effect test

Embodiment 1

[0032] Add sodium p-toluenesulfonate and barium chloride into the ultrasonic reactor, control the initial concentration of sodium p-toluenesulfonate to 0.1 mol / liter, perform ultrasonic reaction at room temperature, control the temperature of the system by circulating condensed water, and react under 400W for 3 hours, and the reaction obtained Put the material into a centrifuge tank, centrifuge to remove the lower layer of sediment, suspend the sediment in water, adjust the apparent concentration to 0.1 mol / liter, stir, age, centrifuge, and dry at low temperature to obtain the catalyst 1 product.

[0033] Chemical reaction formula such as figure 1 As shown, catalyst 1 product yield 89.2%, molecular formula C 14 h 14 o 6 S 2 Ba 1 , white spherical particles, particle size 0.1 ± 0.02 microns, insoluble in water, phenol, elemental analysis: C 35.03%, H 2.92%, O 20.06%.

Embodiment 2

[0035] Add sodium dodecylbenzenesulfonate and barium chloride into an ultrasonic reactor, add water to adjust the initial concentration of sodium dodecylbenzenesulfonate to 0.1 mol / liter, ultrasonically react at 20°C, and control the temperature of the system by circulating condensed water , reacted under 400W ultrasonic conditions for 3 hours, put the reaction product into a centrifuge tank, centrifuge to remove the lower layer of sediment, suspend the sediment in water, adjust the apparent concentration to 0.1 mol / liter, stir and age, then centrifuge, The product of catalyst 2 was obtained by drying at low temperature, and the yield was calculated by weighing.

[0036] Catalyst 2 product yield 86.7%, molecular formula C 36 h 58 o 6 S 2 Ba 1 , white spherical particles, particle size 0.098 ± 0.003 microns, insoluble in water and phenol, elemental analysis: C 54.82%, H 7.48%, O 12.22%.

Embodiment 3

[0038] Put sodium cetyl sulfonate and barium chloride into an ultrasonic reactor, add water to adjust the initial concentration of sodium cetyl sulfonate to 0.1 mol / liter, ultrasonically react, circulate condensed water, control the system temperature, and react for 3 hours Finally, put the reaction product into a centrifuge tank, centrifuge to remove the lower layer of sediment, suspend the sediment in water, adjust the apparent concentration to 0.1 mol / liter, stir and age, centrifuge, and dry at low temperature to obtain the catalyst 3 product, which is weighed and Calculate the yield.

[0039] Catalyst 3 product yield 76.74%, molecular formula C 32 h 66 o 6 S 2 Ba 1, white spherical particles, particle size 0.088 ± 0.013 microns, insoluble in water and phenol, elemental analysis: C 51.16%, H 8.92%, O 12.88%.

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Abstract

The invention discloses a barium sulfonate catalyst and application thereof in synthesis of D,L-P-hydroxyphenyl hydantoin, belonging to the technical field of catalysts. The barium sulfonate catalyst disclosed by the invention is prepared by comprising the following steps: mixing organic zwitter-ion sodium sulfonate with barium chloride, adding into an ultrasonic reaction kettle, reacting at 400 W for 3 h, centrifuging to collect precipitation after reacting, suspending the precipitation in water, adjusting the concentration to 0.1 mol/L, stirring, ageing, centrifuging, and drying at low temperature. The barium sulfonate catalyst disclosed by the invention is steady in granularity, low in corrosivity to reaction equipment, easy to recycle and reusable, and therefore, the yield of D,L-P-hydroxyphenyl hydantoin can be obviously increased.

Description

technical field [0001] The invention belongs to the technical field of catalyst and its application, and relates to a barium sulfonate catalyst and its application in synthesizing D,L-p-hydroxyphenylhydantoin. Background technique [0002] D, L-p-hydroxyphenylhydantoin is white powder, slightly soluble in water, aliased as 5-p-hydroxyphenylhydantoin, molecular formula is C 9 h 8 N 2 o 3 , the relative molecular weight is 192.17. D, L-p-hydroxyphenylhydantoin is an intermediate for the production of D-p-hydroxyphenylglycine, an important pharmaceutical intermediate for the production of amoxicillin, cephalosporins, etc. The side chain is used to produce broad-spectrum antibacterial and convenient-to-use antibiotic drugs such as amoxicillin. [0003] In the early 1990s, the demand for D,L-p-hydroxyphenylhydantoin was small, but with the development of the world's pharmaceutical industry and the increasing demand for chiral drugs in the market, its usage is also gradually ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J31/02C07D233/78
Inventor 乔元彪郭彩珍付文强胡雪梅贺莹褚盼盼秦永其
Owner LULIANG UNIV
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