US1976997A - Method of separating optically active glutamic acid without racemization - Google Patents
Method of separating optically active glutamic acid without racemization Download PDFInfo
- Publication number
- US1976997A US1976997A US664840A US66484033A US1976997A US 1976997 A US1976997 A US 1976997A US 664840 A US664840 A US 664840A US 66484033 A US66484033 A US 66484033A US 1976997 A US1976997 A US 1976997A
- Authority
- US
- United States
- Prior art keywords
- glutamic acid
- racemization
- acid
- optically active
- rotatory
- 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 - Lifetime
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
Definitions
- the optical rotatory glutamic acid which is inevitably racemized with ordinary alkaline matter, is separated without reducing its rotatory power in the least and glutamic acid is crystallized as a big crystal, so that it can be separated from the mother liquor and washed and refined with ease.
- a glycocoll alkyl derivative v such as betaine or sarcosine
- Example IL-II 11.7 grams of powdered betaine' solutionoi sulphuric acid salt of dextro-rotatory'glutamic-acid consisting of 14.7 grams of dextro-rotatory glutamic acid and 66 c. c. of 1.5 normal solution of sulphuric acid, it is dissolved to a clear solution and the crystal oi dextro-rotatory glutamic acid will be produced pretty soon. .When the crystal is collected by 76 filtration and washed with water, substantially the same result as above is obtained.
- a method of recovering optically active dextro-rotatory glutamic acid from its mineral acid 80 salts without racemizatio comprising neutralizingthe combined mineral acid of said salts with an alkyl derivative of glycocoll.
- a method 01 recovering optically active dextro-rotatory glutamic acid from its mineral acid salts without racemization, comprising neutraliz- 1 ing the combined mineral acid of said salts with betaine.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Patent ed a. 16, 1934 UNITED STATES PATENT OFFICE 1.916.997 METHOD OF SEPABATHVG 0 PT! CALLY ACTIVE GLUT IMIZATION Sciao Kanao, Azabn Kn,
to Kabushiki Kaisha C ACID WITHOUT RAGE- Tokyo, Japan, assignor Suzuki Shoten, Tokyo,
Japan, incorporation oi Japan No Drawing. Application April 664,840. In Japan April 12,1932 3 Claims. (Cl. 260-118) great seasoning power by preventing the racemization of glutamic acid.
If'alkali hydroxide or alkali carbonate is used in separating glutamic acidfrom glutamic acid hydrochloride or other mineral acid salt ofglu- 'tamic acid, it is. inevitable that glutamic acid should be partly racemized. This'tendency may be somewhat lessened by the employment of ammonia, but even then the racemization to some extent is unavoidable. According to thisinvengo tion, by using a glycocoll alkyl derivative vsuch as betaine or sarcosine as a neutralizer, the optical rotatory glutamic acid, which is inevitably racemized with ordinary alkaline matter, is separated without reducing its rotatory power in the least and glutamic acid is crystallized as a big crystal, so that it can be separated from the mother liquor and washed and refined with ease.
Laevo-rotatory glutamic acid a far weakerv taste than the dextro-rotatory acid. Therefore, the racemization reduces the value of dextrorotatory'glutamic acid considerably when utilized as a seasoning, so it is a matter of great significance to separate dextro-rotatory glutamic acid without racemization. Emmple-'I;l83.5 grams of dextro-rotatory glutamic acid hydrochloride was dissolved in A 0.6 litre of water and then the solution was mixed with 117' grams of betaino by a stirrer, the crystal of betaine vanished immediately and the o I,
' is added to crystal of dextro-rotatory glutamic acid was formed. After cooling, it was filtered and then washed with water. 7 Thus, it was possible to obtain 140 grams of the product having the melt-" ing point -201.5-202 C. and the specific rotatory power (solution of hydrochloric acid). The mother liquorvconsisting of betaine hydrochloride, betaine may be recovered by the proper treatment.
Example IL-II 11.7 grams of powdered betaine' solutionoi sulphuric acid salt of dextro-rotatory'glutamic-acid consisting of 14.7 grams of dextro-rotatory glutamic acid and 66 c. c. of 1.5 normal solution of sulphuric acid, it is dissolved to a clear solution and the crystal oi dextro-rotatory glutamic acid will be produced pretty soon. .When the crystal is collected by 76 filtration and washed with water, substantially the same result as above is obtained.
I claim: I
1. A method of recovering optically active dextro-rotatory glutamic acid from its mineral acid 80 salts without racemizatio comprising neutralizingthe combined mineral acid of said salts with an alkyl derivative of glycocoll.
2. A method 01 recovering optically active dextro-rotatory glutamic acid from its mineral acid salts without racemization, comprising neutraliz- 1 ing the combined mineral acid of said salts with betaine.
3. A method of recovering optically active dextro-rotatory glutamic acid from its mineral acid salts without racemization, comprising neutralizing the combined mineral acid oi saidsalts with sarcosine; I
SEIZO KANAO.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1976997X | 1932-04-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US1976997A true US1976997A (en) | 1934-10-16 |
Family
ID=16378881
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US664840A Expired - Lifetime US1976997A (en) | 1932-04-12 | 1933-04-06 | Method of separating optically active glutamic acid without racemization |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US1976997A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3413326A (en) * | 1956-10-03 | 1968-11-26 | Gaba Ag | Addition compounds of amino acids and hydrofluoric acid or soluble fluorides,and method of preparing the same |
-
1933
- 1933-04-06 US US664840A patent/US1976997A/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3413326A (en) * | 1956-10-03 | 1968-11-26 | Gaba Ag | Addition compounds of amino acids and hydrofluoric acid or soluble fluorides,and method of preparing the same |
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