DE691229C - Process for the preparation of water-soluble sulfonated phosphatides - Google Patents
Process for the preparation of water-soluble sulfonated phosphatidesInfo
- Publication number
- DE691229C DE691229C DE1935C0050708 DEC0050708D DE691229C DE 691229 C DE691229 C DE 691229C DE 1935C0050708 DE1935C0050708 DE 1935C0050708 DE C0050708 D DEC0050708 D DE C0050708D DE 691229 C DE691229 C DE 691229C
- Authority
- DE
- Germany
- Prior art keywords
- parts
- weight
- phosphatides
- water
- preparation
- 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
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 4
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 5
- 238000006277 sulfonation reaction Methods 0.000 claims description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 150000001299 aldehydes Chemical class 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims 1
- 150000003871 sulfonates Chemical class 0.000 claims 1
- FWFGVMYFCODZRD-UHFFFAOYSA-N oxidanium;hydrogen sulfate Chemical compound O.OS(O)(=O)=O FWFGVMYFCODZRD-UHFFFAOYSA-N 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000008347 soybean phospholipid Substances 0.000 description 5
- PZNPLUBHRSSFHT-RRHRGVEJSA-N 1-hexadecanoyl-2-octadecanoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCCCC(=O)O[C@@H](COP([O-])(=O)OCC[N+](C)(C)C)COC(=O)CCCCCCCCCCCCCCC PZNPLUBHRSSFHT-RRHRGVEJSA-N 0.000 description 4
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 239000007859 condensation product Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- -1 aliphatic aromatic hydrocarbons Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- ALSTYHKOOCGGFT-UHFFFAOYSA-N cis-oleyl alcohol Natural products CCCCCCCCC=CCCCCCCCCO ALSTYHKOOCGGFT-UHFFFAOYSA-N 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 239000010446 mirabilite Substances 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000271 synthetic detergent Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/10—Phosphatides, e.g. lecithin
- C07F9/103—Extraction or purification by physical or chemical treatment of natural phosphatides; Preparation of compositions containing phosphatides of unknown structure
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
Description
Verfahren zur Herstellung von wasserlöslichen sulfonierten Phosphatiden In dem Patent 660 736 ist ein Verfahren zur Herstellung von wasserlöslichen sulfonierten Phosphatiden beschrieben, bei dem man pflanzliche oder tierische. Phösphatide mit mindestens 70% konzentrierter Schwefelsäure in Gegenwart :eines Lösungsmittels bei Temperaturen unter io° so lange behandelt, bis das Reaktionsgemisch wasserlöslich geworden ist. Gegebenenfalls setzt man dabei den Phosphortiden vor der Sulfonierung Fette, öle oder deren Fettsäuren in einer Menge zu, die geringer als die Phosphatidmenge ist. Die Sulfonierung kann auch in Gegenwart wasserentziehender Mittel durchgeführt werden.Process for the preparation of water-soluble sulfonated phosphatides In the patent 660 736 a process for the preparation of water-soluble sulfonated phosphatides is described, in which vegetable or animal. Phösphatide treated with at least 70% concentrated sulfuric acid in the presence of a solvent at temperatures below 10 ° until the reaction mixture has become water-soluble. If necessary, fats, oils or their fatty acids are added to the phosphorus tides before the sulfonation in an amount which is less than the amount of phosphatide. The sulfonation can also be carried out in the presence of dehydrating agents.
Es wurde. gefunden, daß man Erzeugnisse erhält, die in ihren Eigenschaften- den vorerwähnten nicht nur gleichkonunen, sondern sie in manchen Fällen sogar noch übertreffen, wenn man in Gegenwart indifferenter Lösungsmittel und bei Temperaturen unterhalb io° sulfonierte Kondensationsprodukte von Phospbatiden mit aliphatischen, aromatischen oder hydroaromatischen Alkoholen, Aldehyden, Ketonen oder aromatischen oder aliphatischaromatischen Kohlenwasserstoffen herstellt.It was. found that products are obtained which in their properties Not only are they the same as those mentioned above, but in some cases they are even more outperform when in the presence of inert solvents and at temperatures below io ° sulfonated condensation products of phosphatides with aliphatic, aromatic or hydroaromatic alcohols, aldehydes, ketones or aromatic or aliphatic aromatic hydrocarbons.
Man kann dabei :entweder derart verfahren, daß man die Phosphortide mit den genannten kondensierbaren Zusatzstoffen zunächst kondensiert und dann- die erhaltenen Kondensationsprodukte sulfoniert oder @ aber derart, daß Kondensation und Sulfonierung in einem Arbeitsgang gleichzeitig durchgeführt werden. Die Sulfonierung wird mit konzentrierter . Schwefelsäure bei Temperaturen unter io° durchgeführt. Die anzuwendenden Arbeitsbedingungen sind abhängig von den Ausgangsstoffen und von der Art und Menge der Zusatzstoffe. Die nachdem vorliegenden Verfahren erhaltenen Erzeugnisse sind was,sexlöslich und können sowohl für sich allein als auch in Mischung .mit Seifen, synthetischen Waschmitteln, Lösungsmitteln usw. angewandt werden. Die erhaltenen Erzeugnisse eignen sich besonders für die Verwendung in der Textilindustrie, aber jauch für aridere Industrien, wie z. B. für die Lederindustrie.' Beispiel i Eine Mischung von ioo Gewichtsteilen Sojalecithin (handelsüblich), 5o Teilen Butylalkohol und Zoo Teilen Trichloräthylen wirrt bei o bis 6° mit i2o Gewichtsteilen Schwefelsäuremonohydrat sulfoniert. Nach Beendigung der Reaktion wird das Sulfonat mit Eis-Glaubersalz-Lösung ausgewaschen. Das Säurewasser wird abgezogen, und man :erhält nach Neutralisation und Entfernung des Lösungsmittels ein flüssiges, in Wasser klarlösliches Erzeugnis. Beispiel- 2 Zoo Gewichtsteile Sojalecithin und 50 Gewichtsbeile Xylol werden in 400 Gewichtsteilen Trichloräthylen gelöst. In diese Lösung werden 6oo Gewichtsteile Schwefelsäuremonohydrat bei o . bis- .7°.. eingetragen. Nach Beendigung de-Reaktion wird das Sulfonat mit einer Eis - Kochsalz - Mischung ausgewaschen; neutralisiert und vom Lösungsmittel befreit:.,::. Beispiel 3 ioo Gewichtsteile Sojalecithin technisch und io Gewichtsteile einer Alkoholmischung, wie sie durch die Hydrierung von Kokosfettsäuren erhalten wird, werden in croo Gewichtsteilen Benzin gelöst. In die Lösung werden iao Gewichtsteile Schwefelsäuremonohydrat bei o bis i o' eingetragen. Das Sulfonat wird nach beendeter Reaktion mit Eis-Glaubersalz-Läsung ausgewaschen und nach Neutralisation mit Alkali vom Lösungsmittel befreit. Beispiel q. In eine Lösung von ioo Gewichtsteilen Sojalecithin, 15 Gewichtsteilen Oleinalkohol und Zoo Gewichtsteilen Tetrachlorkohlenstoff werden i2o Gewichtsteile Schwefelsäuremonohydrat bei o bis 6° eingetragen. Nach beendeter Reaktion wird das Sulfonat in üblicher Weise ausgewaschen und aufgearbeitet. Beispiel 5 i oo Gewichtsteile Lecithin und 2o Gewichtsteile Oleinalkohol werden in Zoo Gewichtsteilen Trichloräthylen gelöst. Nach Zusatz von 2 5 Gewichtsteilen Essigsäureanhxdrid werden i 5o Gewichtsteile Schwefelsäuremonohydrat bei o bis Gewichtsteile eingetragen. Das Sul--fonat wird mit Eis-Kochsalz-Lösung ausgewaschen und nach Abziehen des Säurewassers @zxeutralisiert.You can either proceed in such a way that the phosphorus tides are first condensed with the condensable additives mentioned and then the condensation products obtained are sulfonated, or else in such a way that condensation and sulfonation are carried out simultaneously in one operation. The sulfonation is concentrated with. Sulfuric acid carried out at temperatures below 10 °. The working conditions to be used depend on the raw materials and the type and amount of additives. The products obtained by the present process are what, sex-soluble and can be used both on their own and in admixture with soaps, synthetic detergents, solvents, etc. The products obtained are particularly suitable for use in the textile industry, but also for other industries, such as e.g. B. for the leather industry. ' EXAMPLE i A mixture of 100 parts by weight of soy lecithin (commercially available), 50 parts of butyl alcohol and zoo parts of trichlorethylene is sulfonated at 0 to 6 ° with 12 parts by weight of sulfuric acid monohydrate. After the reaction has ended, the sulfonate is washed out with ice-Glauber's salt solution. The acidic water is drawn off and: after neutralization and removal of the solvent, a liquid product which is clearly soluble in water is obtained. Example- 2 parts by weight of soy lecithin and 50 parts by weight of xylene are dissolved in 400 parts by weight of trichlorethylene. In this solution 600 parts by weight of sulfuric acid monohydrate at o. up to- .7 ° .. registered. After the de-reaction has ended, the sulfonate is washed out with an ice-table salt mixture; neutralized and freed from solvent:., ::. EXAMPLE 3 100 parts by weight of technical soya lecithin and 10 parts by weight of an alcohol mixture such as that obtained by the hydrogenation of coconut fatty acids are dissolved in 100 parts by weight of gasoline. In general, parts by weight of sulfuric acid monohydrate are introduced into the solution at 0 to 10 '. After the reaction has ended, the sulfonate is washed out with ice-Glauber's salt solution and freed from the solvent after neutralization with alkali. Example q. In a solution of 100 parts by weight of soy lecithin, 15 parts by weight of oleic alcohol and zoo parts by weight of carbon tetrachloride, 120 parts by weight of sulfuric acid monohydrate are introduced at 0 ° to 6 °. After the reaction has ended, the sulfonate is washed out and worked up in the usual way. EXAMPLE 5 100 parts by weight of lecithin and 20 parts by weight of oleic alcohol are dissolved in zoo parts by weight of trichlorethylene. After adding 25 parts by weight of acetic anhydride, 15 parts by weight of sulfuric acid monohydrate are introduced at 0 to 1 parts by weight. The sulphonate is washed out with an ice-saline solution and neutralized after the acidic water has been drawn off.
Beispiel 6 i 5o Gewichtsteile Sojalecithin werden mit 5o Gewichtsteilen Oleinketon 3 Stunden bei ioo° erhitzt. ioo Gewichtsteile dieses Kondensationsproduktes werden in Zoo Gewichtsteilen Trichloräthylen gelöst und bei o bis 5° mit i3o Gewichtsteilen Schwefelsäuremonohydrat sulfoniert. Die Aufarbeitung des Erzeugnisses erfolgt in üblicher Weise.Example 6 150 parts by weight of soy lecithin are combined with 50 parts by weight Oleinketone heated at 100 ° for 3 hours. 100 parts by weight of this condensation product are dissolved in zoo parts by weight of trichlorethylene and at 0 to 5 ° with 13o parts by weight Sulfonic acid monohydrate sulfonated. The product is processed in usual way.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1935C0050708 DE691229C (en) | 1935-03-03 | 1935-03-03 | Process for the preparation of water-soluble sulfonated phosphatides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1935C0050708 DE691229C (en) | 1935-03-03 | 1935-03-03 | Process for the preparation of water-soluble sulfonated phosphatides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE691229C true DE691229C (en) | 1940-05-21 |
Family
ID=7027232
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1935C0050708 Expired DE691229C (en) | 1935-03-03 | 1935-03-03 | Process for the preparation of water-soluble sulfonated phosphatides |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE691229C (en) |
-
1935
- 1935-03-03 DE DE1935C0050708 patent/DE691229C/en not_active Expired
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