US1381057A - Process for the production of a crystallized ester of the stearoricinate-diiodid - Google Patents
Process for the production of a crystallized ester of the stearoricinate-diiodid Download PDFInfo
- Publication number
- US1381057A US1381057A US395138A US39513820A US1381057A US 1381057 A US1381057 A US 1381057A US 395138 A US395138 A US 395138A US 39513820 A US39513820 A US 39513820A US 1381057 A US1381057 A US 1381057A
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- US
- United States
- Prior art keywords
- diiodid
- ester
- stearo
- crystallized
- production
- 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
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/62—Halogen-containing esters
- C07C69/65—Halogen-containing esters of unsaturated acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/732—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids of unsaturated hydroxy carboxylic acids
Definitions
- the ester may be produced in two processes:
- Iodin is addedto the ethyl ester of the stearo-ricinate according to the methods coming into consideration.
- the ethyl ester is to be used for therapeutic purposes.
- Example 1 100 parts of stearo-ricinate are dissolved under very "Weak heating in about 250 parts of 75% acetic acid and the calculated quantity of iodin is added to the solution at once. The solution is then st1rred at ordinary temperature until all the iodin is dissolved. The resulting mass soon solidifies to a crystalline pulp. The same volume of water is added and the quantity of excessive iodin which may be present is taken away by sulfurous acid. The nearly or quite white stearo-ricinate-diiodid ob tained is sucked oil and washed with water. The preparation after being once crystallized is perfectly clean. It will be dissolved in excessive pure alcohol, whereupon the.
- Example 2 125 g. iodin are admitted in a concentrated solution of 100 g. of stearoricinate-ethyl-ester in glacial acetic acid. After stirring for 1 or 2 hours under a low heat all the iodin is solved. The dark brown colored solution after a longer stay is precipitated with water and the separated heavy oil is washed with water. When cooling it solidifies rapidly and is crystallized out of spirit or ligroin.
- a crystalline ester of stearo-rieinatediiodid havin valuable therapeutic quali- %eing the ethylester of steamricinate-diiodid.
Description
.aasnoer.
FRIEDRICH BOEDECKER, F BRITZ, NEAR BERLIN, PRUSSIA, GERMANY.
PROC$S FOR THE PRODUCTION OF A CRYSTALLIZED ESTER OF THE STEARO- RICINATE-DIIODID.
No Drawing.
To all whom it may concem:
Be it known that I, FRIEDRICH Bononoxnn, a citizen of the Free State of Prussia, in the German Republic, residing at Britz, near Berlin, in the Free State ,of Prussia, Germany, have invented Improvements in Processes for the Production of a Crystallized Ester of Stearo-Ricinate-Diiodid; and I do hereby declare the following to'be a full, clear, and exact description of the same.
From the esters of the stearo-ricinatediiodid up to now only methyl ester has been produced as a Weak yellow colored oil (see reports of the Deutsohe C'hemis'ciw Gesellschaft 46 page 2004:). It has now been found that the ethyl ester can easily be produced in solid crystallized form which could not be foreseen with regard to the properties of the methyl ester mentioned above. 7
The ester may be produced in two processes:
(1) lodin is added to the stearo-ricinate CH (CH .CI-IOHJCH C :C (CH YLCO H, which is known as octadecin 9 OL (12) acid (1) according to the Geneva nomenclature and the acid produced is reduced to ethyl ester.
According to the process of Arnaud and Posternack iodin in lacial acetic acid can easily be added to the acid of the series C H O This reaction may also be transferred to the stearo-ricinate, the hydroxyl series of the stearo-ricinate however causes diiferent by-reactions (see reports of the Deutsahe Uhemische Gesellschaft 46 page 2091). On the one hand dark colored products are obtained while on the other hand the stearo-ricinate is subjected to acetylening, whereby the stearo-ricinate-diiodid obtained is always greatly polluted by oily admixtures. These by-reactions are said to be prevented by iodizing (Z. 0.) "during hours at ordinary temperature or a temperature of The reception of the iodin is quantitative, the diiodid obtained however is in this case also polluted with dark colored dirty products which substantiall reduce the output of pure crystallized dilodid as well as the constancy of the raw-diiodid with regard to solvents. The injurious influence of the glacial acetic acid will be seen in a far higher degree if endeavors are made to work on large scale according to the said process.
Specification of Letters Patent.
Patented June 7, 1921..
Application filed July 9, 1920. Serial No. 395,138.
It has now been found that the acetylening produced by the excessive glacial acetic acid at the usual temperature and the combmed disturbing by-products may be prevented by iodizing in aqueous acetic-acid. After removing some of the excessive iodin SOlld nearly colorless diiodid is obtained by crystalllzing of the resulting mass and preclpitatlng of the mother-lye. This diiodid may easil be crystallized and according'to thiee usua methods transferred into ethyl es r.
(2) Iodin is addedto the ethyl ester of the stearo-ricinate according to the methods coming into consideration.
The ethyl ester is to be used for therapeutic purposes.
Example 1: 100 parts of stearo-ricinate are dissolved under very "Weak heating in about 250 parts of 75% acetic acid and the calculated quantity of iodin is added to the solution at once. The solution is then st1rred at ordinary temperature until all the iodin is dissolved. The resulting mass soon solidifies to a crystalline pulp. The same volume of water is added and the quantity of excessive iodin which may be present is taken away by sulfurous acid. The nearly or quite white stearo-ricinate-diiodid ob tained is sucked oil and washed with water. The preparation after being once crystallized is perfectly clean. It will be dissolved in excessive pure alcohol, whereupon the. solution is saturated in the cold with hydrochloric acid-gas and the resulting mixture left to itself for several hours. Then the ester is precipitated with water and after drying crystallized out of low boiling benzin. The ester is in this way obtained in the form of colorless well formed needles which melt at a temperature of 31. The new combination is insoluble in water, easil soluble however in nearly all organic sol vents.
Example 2: 125 g. iodin are admitted in a concentrated solution of 100 g. of stearoricinate-ethyl-ester in glacial acetic acid. After stirring for 1 or 2 hours under a low heat all the iodin is solved. The dark brown colored solution after a longer stay is precipitated with water and the separated heavy oil is washed with water. When cooling it solidifies rapidly and is crystallized out of spirit or ligroin.
Having now described and ascertained the ties, the ester nature of my invention and the manner in which the same is to be perfolmed I now declare what I claim and desire to secure by Letters Patent of the United States:
1. A crystalline ester of stearo-rieinatediiodid havin valuable therapeutic quali- %eing the ethylester of steamricinate-diiodid.
2. A process for the production of a crys- 10 talline ester characterized in this that first amps? iodin in the presence of aqueous acetic-acid is added to the stearo ricinate and the latter then transferred to the ethyl-ester.
In, testimony whereof I have signed my name to this specification in the presence of 15 two subscribin Witnesses.
DR. FRI DRIC'I-I BOEDEOKER Witnesses:
FRANZ SOHROENBERLEY, ERNST BASGH.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US395138A US1381057A (en) | 1920-07-09 | 1920-07-09 | Process for the production of a crystallized ester of the stearoricinate-diiodid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US395138A US1381057A (en) | 1920-07-09 | 1920-07-09 | Process for the production of a crystallized ester of the stearoricinate-diiodid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US1381057A true US1381057A (en) | 1921-06-07 |
Family
ID=23561852
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US395138A Expired - Lifetime US1381057A (en) | 1920-07-09 | 1920-07-09 | Process for the production of a crystallized ester of the stearoricinate-diiodid |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US1381057A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5959130A (en) * | 1996-07-02 | 1999-09-28 | Finetex, Inc. | Castor based benzoate esters |
-
1920
- 1920-07-09 US US395138A patent/US1381057A/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5959130A (en) * | 1996-07-02 | 1999-09-28 | Finetex, Inc. | Castor based benzoate esters |
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