GB723397A - Production of hydantoin and of glycine - Google Patents
Production of hydantoin and of glycineInfo
- Publication number
- GB723397A GB723397A GB29020/52A GB2902052A GB723397A GB 723397 A GB723397 A GB 723397A GB 29020/52 A GB29020/52 A GB 29020/52A GB 2902052 A GB2902052 A GB 2902052A GB 723397 A GB723397 A GB 723397A
- Authority
- GB
- United Kingdom
- Prior art keywords
- solution
- hydantoin
- formaldehyde
- glycine
- alkali metal
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/72—Two oxygen atoms, e.g. hydantoin
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A process for making hydantoin comprises introducing one molecular proportion of formaldehyde into contact with an aqueous solution containing an ammonium carbonate and an alkali metal cyanide in proportions sufficient to provide the chemical equivalent of at least two mols. of ammonia, and at least 1.5 mols. of carbonate and at least one mol. of the alkali metal p cyanide, maintained at a temperature of from -10 DEG to 30 DEG C., either by slowly adding the formaldehyde in the form of an aqueous solution at a rate such that not more than one mol. of the formaldehyde is released into contact with the dissolved salts in the solution over a period of 4 hours or more or by dissolving a proportionate amount of paraformaldehyde in the solution, then heating the solution at a temperature of from 50 DEG to 120 DEG C. to complete the reaction and form hydantoin. Glycine is prepared by boiling the aqueous reaction liquid to distil ammonia and carbon dioxide, mixing the residual aqueous liquid with an alkali metal hydroxide in amount corresponding to at least two mols. of the alkali metal hydroxide per mol. of the formaldehyde starting material, heating the alkaline solution at a temperature between 130 DEG and 250 DEG C. under pressure to hydrolyse the hydantoin and recovering glycine from the alkaline hydrolysis liquid. Starting materials mentioned include sodium or potassium cyanide and ammonium carbonate or bicarbonate. The alkaline solutions containing hydantoin and glycine are treated with cation exchange resins in hydrogen form to remove alkali metal ions before separating the desired products. Insoluble sulphonated vinyl aromatic resins and sulphonated phenol-formaldehyde resins are mentioned. In examples: hydantoin is obtained by dissolving paraformaldehyde in an aqueous solution containing sodium cyanide and ammonium bicarbonate, boiling the solution, treating it with decolourizing charcoal and a sulphonated vinyl aromatic resin in hydrogen form and concentrating and cooling the residual solution (1); reaction liquor from (1) is heated in an autoclave with sodium hydroxide and the solution is decolourized, boiled, cooled, treated with the ion exchange resin used in (1); concentrated and treated with methyl alcohol to obtain glycine (2); and formaldehyde is gradually added to an aqueous solution of ammonium carbonate and sodium cyanide, the mixture is heated under pressure, ammonia and carbon dioxide are boiled off, aqueous caustic soda is added and the solution is pumped through a heated tube to effect hydrolysis of the hydantoin. The hydrolysed solution is treated with the ion exchange resin used in (1) and concentrated and glycine is precipitated by the addition of methyl alcohol. Specifications 687,486 and 693,522 are referred to. Reference has been directed by the Comptroller to Specifications 687,486 and 693,522.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US723397XA | 1952-03-22 | 1952-03-22 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB723397A true GB723397A (en) | 1955-02-09 |
Family
ID=22106969
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB29020/52A Expired GB723397A (en) | 1952-03-22 | 1952-11-17 | Production of hydantoin and of glycine |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB723397A (en) |
-
1952
- 1952-11-17 GB GB29020/52A patent/GB723397A/en not_active Expired
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