Method for synthesizing allantoin

A synthesis method and technology for allantoin, applied in the direction of organic chemistry, etc., can solve the problems of difficult control, high cost, complicated operation and the like

Active Publication Date: 2012-08-01
BEIJING SUNPU BIOCHEM TECH
View PDF4 Cites 14 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Li Guiyun and Ma Jiangquan disclosed in "Synthesis and Characterization of Allantoin" ("Journal of Jiangsu Institute of Petrochemical Technology") that the yield of allantoin was 59.3% with nitric acid and sulfuric acid mixed acid as catalyst, and its raw material glyoxylic acid was made of Produced by nitric acid oxidation method, allantoin is directly produced without purification, and the product will be affected by residual glyoxal, by-product oxalic acid and by-products of various reactions, and the quality will decrease
Lei Hong et al. disclosed the synthesis of allantoin by using inorganic acids such as sulfuric acid, hydrochloric acid and nitric acid as catalysts in the "Summary of Allantoin Production Process and Market" ("Proceedings of the 21st Technical Exchange Conference of the National Medium Nitrogen Information Collaboration Group"). The yield is between 52% and 58%; Chinese Patent Publication No. CN1528749A, published on September 15, 2004, the name of the invention is "New Technology for Allantoin Synthesis", and the application discloses the use of metal catalysts to catalyze the synthesis of Allantoin yield can only reach 56%
In addition, there are many reports on the synthesis of allantoin with solid acid as a catalyst, but the yield is mostly below 60%. Only Shi Gaofeng et al. Heteropoly acid [H 3 PW 12 o 40 · x H 2 O] as a catalyst, the yield can reach 68.6%, but the amount of urea is too much; Fu Xinling et al. in 2007 "SO 4 2- /TiO 2 Synthesis of Allantoin Catalyzed by Solid Superacids" ("The 11th Academic Conference on Catalysis") 4 2- /TiO 2 The highest yield of allantoin catalyzed by solid superacid is only 57.35%, and the production of solid acid is difficult and costly, so it is not suitable for industrial production
In addition, the Chinese Patent Publication No. CN1765888A, published on May 3, 2006, is an invention titled "A Synthetic Proc

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Method for synthesizing allantoin
  • Method for synthesizing allantoin
  • Method for synthesizing allantoin

Examples

Experimental program
Comparison scheme
Effect test

Example Embodiment

[0108] Example 1

[0109] (1) Preparation of ionic liquid:

[0110] Put 850g of 1,4-butane sultone in a 2L three-necked flask, and gradually add 410g of N-methylimidazole dropwise at 25°C. The dropwise addition is completed within 30 minutes, and the reaction solution is heated to 40°C, stirred for 12 hours, and filtered to obtain The white solid was placed in 1.6L of toluene and stirred for 15 minutes, filtered with suction, and the obtained crude product was placed in a vacuum drying oven (90°C, dried at 0.01Mpa to constant weight); 919g of the intermediate was obtained. Take 584g of the white powdery solid obtained above, put it into a 2L three-neck flask, add 1.1L of methanol to dissolve, slowly add 265g of sulfuric acid (mass fraction 98%) dropwise, keep the temperature at 80°C after the dropwise addition, and react for 6h. After the reaction finished, the excess moisture was evaporated by the reaction solution with a rotary evaporator, and the obtained [(CH 2 ) 4 SO ...

Example Embodiment

[0113] Example 2

[0114] After drying the ionic liquid collected in the reaction of Example 1, add 2.0 L of methanol, and heat to reflux for 2 hours. After the reflux is completed, cool and filter to obtain the filtrate that is concentrated and separate the methanol (it can be used for the next time) to obtain the ionic liquid that can be reused once. Liquid A1, add glyoxylic acid aqueous solution and urea, the molar ratio of glyoxylic acid to urea is 1:4.2, heat the reaction solution to 68°C, react for 6.5h, stop heating, cool to 15°C, filter to obtain a white solid, Wash the solid with 1L of deionized water, wash three times (1L each time), combine the washing liquid and filtrate, concentrate and remove the water to obtain the ionic liquid for repeated use, and dry it in a vacuum drying oven for later use. The white solid obtained by the reaction is the product Allantoin was taken out and dried in an oven at 100°C, weighed, and the calculated yield was 75.06%, which was mar...

Example Embodiment

[0117] Example 3

[0118] (1) Preparation of ionic liquid:

[0119] Put 850g of 1,4-butane sultone in a 2L three-necked flask, gradually add 395g of pyridine dropwise at 25°C, and the dropwise addition is completed within 30min, heat the reaction solution to 40°C, stir for 12h, and filter to obtain a white solid. It was placed in 1.6L toluene and stirred for 15min, filtered with suction, and the obtained crude product was placed in a vacuum drying oven (90°C, dried at 0.01Mpa to constant weight) to obtain 896g of intermediate; take the white powder obtained above Add 578g of solids into a 2L three-neck flask, add 1.1L of deionized water to dissolve, slowly add 265g of sulfuric acid (mass fraction 98%) dropwise, keep the temperature at 80°C after the dropwise addition, and react for 6h. The excess water was evaporated with a rotary evaporator to obtain [(CH 2 ) 4 SO 3 HPy][HSO 4 ], it was placed in a vacuum drying oven (90°C, 0.01Mpa, dried to constant weight), and 650g wa...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

No PUM Login to view more

Abstract

The invention relates to a method for synthesizing allantoin. The allantoin is synthesized by taking acid ionic liquid as a catalyst and glyoxylic acid and urea as raw materials. A process is simple, raw materials are bulk chemical raw materials, yield is high, the method is easy to industrially popularize, the yield of allantoin is stable and can reach over 68 percent, and the acid ionic liquid used as the catalyst can be repeatedly used for more than 5 times; and the process is pollution-free and environment-friendly, and has a good ecological effect and social and economic benefits. Through assay determination, the content of the obtained allantoin product is in the range required by the United States Pharmacopeia (USP29), and other indexes of the obtained allantoin product also meet the USP 29.

Description

technical field [0001] The invention relates to a method for synthesizing allantoin. Background technique [0002] Allantoin (allantoin), the chemical name is 1-ureidodiaziridine-2,4-dione, which belongs to imidazole heterocyclic compound, usually exists in the form of white crystal or crystalline powder, odorless and tasteless . [0003] Allantoin widely exists in nature, such as allantoic fluid, fetal urine, human and mammalian embryos and excreta, and tobacco, wheat grains, and sugar beets also contain allantoin. However, the amount of natural allantoin is limited, the extraction process is complicated, and the yield is extremely low, so most of the current commercial allantoin is artificially synthesized. [0004] In medicine, allantoin is a drug with multiple functions. It can be used directly or as an additive. Allantoin can treat various skin diseases, such as psoriasis, dermatitis, dry skin, etc., and can promote skin Cell and tissue growth, rapid wound healing an...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
IPC IPC(8): C07D233/88
Inventor 胡文静潘咏梅
Owner BEIJING SUNPU BIOCHEM TECH
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products