DE967313C - Process for making water-insoluble or sparingly soluble organic compounds such as hydrocarbons or their oxygen-, nitrogen- or sulfur-containing compounds - Google Patents
Process for making water-insoluble or sparingly soluble organic compounds such as hydrocarbons or their oxygen-, nitrogen- or sulfur-containing compoundsInfo
- Publication number
- DE967313C DE967313C DEI4560A DEI0004560A DE967313C DE 967313 C DE967313 C DE 967313C DE I4560 A DEI4560 A DE I4560A DE I0004560 A DEI0004560 A DE I0004560A DE 967313 C DE967313 C DE 967313C
- Authority
- DE
- Germany
- Prior art keywords
- organic compounds
- insoluble
- hydrocarbons
- sparingly soluble
- sulfur
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K35/00—Medicinal preparations containing materials or reaction products thereof with undetermined constitution
- A61K35/02—Medicinal preparations containing materials or reaction products thereof with undetermined constitution from inanimate materials
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
Description
Verfahren zum Wasserlöslichmachen von in Wasser unlöslichen oder schwerlöslichen organischen Verbindungen wie Kohlenwasserstoffen oder deren sauerstoff-, stickstoff-oder schwefelhaltigen Abkömmlingen Die Erfindung betrifft ein Verfahren zum Wasserlöslichmachen von in Wasser unlöslichen oder schwerlöslichen organischen Verbindungen, wie Kohlenwasserstoffen oder deren sauerstoff-, stickstoff- oder schwefelhaltigen Abkömmlingen.Process for making water-insoluble or sparingly soluble in water organic compounds such as hydrocarbons or their oxygen, nitrogen or sulfur-containing derivatives The invention relates to a water solubilization method of organic compounds that are insoluble or sparingly soluble in water, such as hydrocarbons or their oxygen-, nitrogen- or sulfur-containing derivatives.
Man hat bereits vor langer Zeit vorgeschlagen, mit den damals bekannten schwarzbraunen Produkten einer üblichen Sulfonierung von Schieferölen, Harzölen od. dgl. schwer wasserlösliche organische Verbindungen, wie Phenole und Kohlenwasserstoffe, in klare wäßrige Lösung zu bringen, um deren Anwendungsmöglichkeiten zu erhöhen (deutsche Patentschriften 76 I33 und 80 260). It was proposed a long time ago, with the ones known at the time black-brown products of a common sulfonation of shale oils, resin oils or the like poorly water-soluble organic compounds, such as phenols and hydrocarbons, to bring in clear aqueous solution in order to increase their application possibilities (German patents 76 I33 and 80 260).
Eine für die Praxis ausreichende Löslichmachung wurde aber nur dann beobachtet, wenn aus den Lösungsvermittlern die sogenannten Sulfone, die sich bei der Sulfonierung der Ausgangsprodukte als wasserunlösliche Körper neben den wasserlöslichen Sulfonsäuren bilden, vorher entfernt wurden. Solubilization sufficient for practical use was only then achieved observed when from the solubilizers the so-called sulfones, which are at the sulfonation of the starting products as water-insoluble bodies in addition to the water-soluble ones Form sulfonic acids, have been removed beforehand.
Es zeigte sich nun überraschenderweise, daß hellfarbige Sulfonierungprodukte, wie sie durch schonende Sulfonierung nach den Vorschriften der deutschen Patentschrift 624 317, hergestellt werden, im Gegensatz zu den bisherigen Erfahrungen mit den schwarzbraunen Sulfonierungsprodukten dann die besten Eigenschaften als Lösungsvermittler für in Wasser unlösliche bzw. schwerlösliche Verbindungen, wie Kohlenwasserstoffe oder deren sauerstoff-, stickstoff- oder schwefelreichen Verbindungen, aufweisen, wenn die Sulfone nicht vorher extrahiert werden. Das Lösungsvermögen dieser hellfarbigen Verbindungen ist gegenüber den bekannten schwarzbraunen Sulfonierungsprodukten stark erhöht, wobei auch die hellfarbigen Sulfonsäuren allein bereits eine wesentliche Steigerung der Löslichmachung gegenüber den schwarzbraunen Sulfonierungsprodukten bewirken. Das erfindungsgemäße Verfahren eignet sich insbesondere für die Löslichmachung von Fettsäuren. It has now been found, surprisingly, that light-colored sulfonation products, such as by gentle sulfonation according to the regulations of the German patent 624 317, in contrast to previous experience with the black-brown sulfonation products then the best properties as a solubilizer for compounds that are insoluble or sparingly soluble in water, such as hydrocarbons or their oxygen, nitrogen or sulfur-rich Compounds, if the sulfones are not previously extracted. The ability to solve this light-colored compound is opposite to the known black-brown sulfonation products greatly increased, with the light-colored sulfonic acids alone already being an essential one Increase in solubilization compared to the black-brown sulfonation products cause. The process according to the invention is particularly suitable for solubilization of fatty acids.
Die Vorteile des neuen Verfahrens ergeben sich aus folgenden Vergleichsversuchen: Es wurden wäßrige Lösungen hergestellt, die jeweils einen Trockenrückstand von 250/0 der zu vergleichenden Sulfonierungsprodukte enthielten. The advantages of the new process result from the following comparative tests: Aqueous solutions were prepared, each with a dry residue of 250/0 of the sulfonation products to be compared.
In klare wäßrige Lösung gebracht wurde ein Fettsäuregemisch von Caprylsäure und Undecylensäure im Verhältnis 1 : 1, von dem folgende Mengen in Prozentzahlen gelöst werden konnten: Beispiel I Durch ein schwarzbraunes Sulfonierungsprodukt aus Seefelder Schieferöl: 20/0, durch das gleiche Produkt nach Entfernung der Sulfone: 7,50/0, durch ein hellfarbiges Sulfonierungsprodukt aus Seefelder Schieferöl (nach den Vorschriften der deutschen Patentschrift 624317 hergestellt): I50/o, durch das gleiche Produkt nach Entfernung der Sulfone: I2°/o.A fatty acid mixture of caprylic acid was brought into a clear aqueous solution and undecylenic acid in a ratio of 1: 1, of which the following amounts are in percentages could be solved: Example I By a black-brown sulfonation product from Seefeld shale oil: 20/0, by the same product after removal of the sulfones: 7.50 / 0, through a light-colored sulfonation product from Seefeld shale oil (after the regulations of the German patent 624317): I50 / o, by the same product after removal of the sulfones: 12%.
Beispiel 2 Durch ein schwarzbraunes Sulfonierungsprodukt eines Jura-Schieferöls ist keine klare Lösung erhältlich, durch das gleiche Produkt nach Entfernung der Sulfone sind 2°/o-, und durch ein hellfarbiges Sulfonierungsprodukt aus Jura-Schieferöl, hergestellt nach den Vorschriften der deutschen Patentschrift 624317 sind IS"O/o klar löslich. Example 2 By a black-brown sulfonation product of a Jura shale oil no clear solution is obtainable by the same product after removal of the Sulphones are 2%, and due to a light-colored sulphonation product from Jura shale oil, manufactured according to the regulations of the German patent specification 624317 are IS "O / o clearly soluble.
Beispiel 3 Als weiteres Beispiel für das erfindungsgemäße Verfahren wird Cumarin genannt. Die Löslichkeit von Cumarin ist sehr gering. Es löst sich in kaltem Wasser nur zu etwa 0,250/0. Die Versuchsverhältnisse wurden wie Beispiel I und 2 gewählt. Example 3 As a further example of the method according to the invention is called coumarin. The solubility of coumarin is very low. It dissolves in cold water only about 0.250 / 0. The experimental conditions were as in example I and 2 chosen.
Es wurden folgende Mengen in Prozentzahlen gelöst: Durch ein schwarzbraunes Sulfonierungsprodukt aus Seefelder Schieferöl nach Entfernung der Sulfone: unter 20/o; durch ein hellfarbiges Sulfonierungsprodukt aus Seefelder Schieferöl, nach den Vorschriften der deutschen Patentschrift 624 317 hergestellt, 60/o. The following amounts were dissolved in percentages: By a black-brown Sulphonation product from Seefeld shale oil after removal of the sulphones: under 20 / o; by a light-colored sulfonation product made from Seefeld shale oil the regulations of the German patent 624 317 produced, 60 / o.
Claims (2)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEI4560A DE967313C (en) | 1951-08-29 | 1951-08-29 | Process for making water-insoluble or sparingly soluble organic compounds such as hydrocarbons or their oxygen-, nitrogen- or sulfur-containing compounds |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEI4560A DE967313C (en) | 1951-08-29 | 1951-08-29 | Process for making water-insoluble or sparingly soluble organic compounds such as hydrocarbons or their oxygen-, nitrogen- or sulfur-containing compounds |
Publications (1)
Publication Number | Publication Date |
---|---|
DE967313C true DE967313C (en) | 1957-10-31 |
Family
ID=7184807
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DEI4560A Expired DE967313C (en) | 1951-08-29 | 1951-08-29 | Process for making water-insoluble or sparingly soluble organic compounds such as hydrocarbons or their oxygen-, nitrogen- or sulfur-containing compounds |
Country Status (1)
Country | Link |
---|---|
DE (1) | DE967313C (en) |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE76133C (en) * | Dr. O. HELMERS in Hamburg, Bohnenstr. 21 | Process for solubilizing phenols, hydrocarbons, etc. in water | ||
DE536912C (en) * | 1927-06-01 | 1931-10-28 | Bataafsche Petroleum | Process for the production and / or stabilization of dispersions of substances which are insoluble or difficult to dissolve in water |
DE614227C (en) * | 1927-01-30 | 1935-06-06 | Oranienburger Chem Fab Akt Ges | Process for the production of high molecular weight water-soluble sulfonation products |
DE624317C (en) * | 1933-01-12 | 1936-01-23 | Erich Wernicke Dr | Process for the production of sulfur-rich, light-colored sulfonation products from sulfur-rich mineral oils, tea oils or shale oils |
DE691534C (en) * | 1935-05-26 | 1940-05-29 | Hydrierwerke Akt Ges Deutsche | Process for the preparation of disinfecting aqueous solutions of phenol, its homologues and derivatives |
-
1951
- 1951-08-29 DE DEI4560A patent/DE967313C/en not_active Expired
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE76133C (en) * | Dr. O. HELMERS in Hamburg, Bohnenstr. 21 | Process for solubilizing phenols, hydrocarbons, etc. in water | ||
DE614227C (en) * | 1927-01-30 | 1935-06-06 | Oranienburger Chem Fab Akt Ges | Process for the production of high molecular weight water-soluble sulfonation products |
DE536912C (en) * | 1927-06-01 | 1931-10-28 | Bataafsche Petroleum | Process for the production and / or stabilization of dispersions of substances which are insoluble or difficult to dissolve in water |
DE624317C (en) * | 1933-01-12 | 1936-01-23 | Erich Wernicke Dr | Process for the production of sulfur-rich, light-colored sulfonation products from sulfur-rich mineral oils, tea oils or shale oils |
DE691534C (en) * | 1935-05-26 | 1940-05-29 | Hydrierwerke Akt Ges Deutsche | Process for the preparation of disinfecting aqueous solutions of phenol, its homologues and derivatives |
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