DE1046010B - Process for the preparation of carbamic acid esters of sugars - Google Patents
Process for the preparation of carbamic acid esters of sugarsInfo
- Publication number
- DE1046010B DE1046010B DEF23597A DEF0023597A DE1046010B DE 1046010 B DE1046010 B DE 1046010B DE F23597 A DEF23597 A DE F23597A DE F0023597 A DEF0023597 A DE F0023597A DE 1046010 B DE1046010 B DE 1046010B
- Authority
- DE
- Germany
- Prior art keywords
- sugars
- carbamic acid
- acid esters
- preparation
- parts
- 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.)
- Pending
Links
- 235000000346 sugar Nutrition 0.000 title claims description 16
- 150000008163 sugars Chemical class 0.000 title claims description 10
- 229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 0.000 title claims description 6
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 4
- -1 alkyl isocyanates Chemical class 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 239000012948 isocyanate Substances 0.000 claims description 3
- 150000001913 cyanates Chemical class 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- 229930006000 Sucrose Natural products 0.000 description 8
- 229960004793 sucrose Drugs 0.000 description 8
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 7
- 239000005720 sucrose Substances 0.000 description 7
- QWDQYHPOSSHSAW-UHFFFAOYSA-N 1-isocyanatooctadecane Chemical compound CCCCCCCCCCCCCCCCCCN=C=O QWDQYHPOSSHSAW-UHFFFAOYSA-N 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 239000003599 detergent Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- GUBGYTABKSRVRQ-PICCSMPSSA-N D-Maltose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- 239000013530 defoamer Substances 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
- 239000000047 product Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 241000220317 Rosa Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- BXXLBMBLLVIOKO-UHFFFAOYSA-N octadecylcarbamic acid Chemical compound CCCCCCCCCCCCCCCCCCNC(O)=O BXXLBMBLLVIOKO-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/12—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by acids having the group -X-C(=X)-X-, or halides thereof, in which each X means nitrogen, oxygen, sulfur, selenium or tellurium, e.g. carbonic acid, carbamic acid
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D19/00—Degasification of liquids
- B01D19/02—Foam dispersion or prevention
- B01D19/04—Foam dispersion or prevention by addition of chemical substances
- B01D19/0404—Foam dispersion or prevention by addition of chemical substances characterised by the nature of the chemical substance
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/66—Non-ionic compounds
- C11D1/662—Carbohydrates or derivatives
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/0005—Other compounding ingredients characterised by their effect
- C11D3/001—Softening compositions
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Wood Science & Technology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Toxicology (AREA)
- General Chemical & Material Sciences (AREA)
- Dispersion Chemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Saccharide Compounds (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
DEUTSCHESGERMAN
Die Erfindung betrifft ein Verfahren zur Herstellung von Carbamidsäureestern von Zuckern; das Verfahren besteht darin, daß man die Zucker mit Alkylisocyanaten umsetzt, die im Alkylrest mehr als 8 Kohlenstoffatome enthalten. Die so hergestellten Carbamidsäureester der Zucker besitzen wertvolle oberflächenaktive Eigenschaften und können als Waschmittel sowie insbesondere als Entschäumer verwendet werden.The invention relates to a process for the preparation of carbamic acid esters of sugars; the The process consists in reacting the sugars with alkyl isocyanates which are more than in the alkyl radical Contains 8 carbon atoms. The sugar carbamic acid esters produced in this way are valuable surface-active properties and can be used as detergents and especially as defoamers be used.
Als Zucker seien beispielsweise Rohrzucker, Malzzucker, Milchzucker und Riffmose genannt. Geeignete Alkylisocyanate, die im Alkylrest mehr als 8 Kohlenstoffatome enthalten, sind vor allem Verbindungen vom Typ des Stearylisocyanats.Cane sugar, malt sugar, milk sugar and reef rose can be mentioned as sugars, for example. Suitable Alkyl isocyanates which contain more than 8 carbon atoms in the alkyl radical are primarily compounds of the stearyl isocyanate type.
Die Umsetzung der Zucker mit den Alkylisocya- *5 naten erfolgt zweckmäßig unter Erhitzen in indifferenten Lösungsmitteln, z. B. in Dimethylformamid. Geeignete Mengenverhältnisse der miteinander umzusetzenden Komponenten lassen sich durch Vorversuche leicht ermitteln; sollen Zuckerester hergestellt werden, die nur einen Alkylcarbamidsäurerest enthalten, so wendet man die Zucker zweckmäßig im Überschuß an; sollen jedoch Zuckerester hergestellt werden, die zwei oder mehr Alkylcarbamidsäurereste enthalten, so setzt man die Komponenten zweckmäßig in molaren Verhältnissen ein.The implementation of the sugars with the Alkylisocya- * 5 naten is expediently carried out with heating in inert solvents, eg. B. in dimethylformamide. Suitable proportions of the components to be reacted with one another can be determined by preliminary tests easily determine; if sugar esters are to be produced that contain only one alkyl carbamic acid residue, so it is expedient to use the sugars in excess; however, sugar esters are supposed to be produced which contain two or more alkyl carbamic acid residues, the components are expediently set in molar proportions.
Gegenüber den bekannten Zuckerestern, die durch Umsetzung von Zuckern mit Fettsäuren bzw. mit Estern aus Fettsäuren und niederen Alkoholen erhältlich sind, zeichnen sich die Carbamidsäureester der Erfindung durch eine stärkere Oberflächenaktivität aus.Compared to the well-known sugar esters, which are made by reacting sugars with fatty acids or with Esters from fatty acids and lower alcohols are available, the carbamic acid esters stand out of the invention by a stronger surface activity.
Die in den nachfolgenden Beispielen angegebenen Teile sind Gewichtsteile.The parts given in the following examples are parts by weight.
35 Teile Saccharose werden in 30O1 Teilen wasserfreiem Dimethylformamid gelöst und mit 60 Teilen Stearylisocyanat 1 bis 2 Stunden unter Rühren auf etwa 100° C erhitzt. Dann wird das Lösungsmittel im Vakuum abdestilliert. Man erhält den Saccharosestearylcarbamidsäurediester in theoretischer Ausbeute in Form eines sehr schwachen gelblichgefärbten Produktes, das sich als Entschäumer verwenden läßt.35 parts of sucrose are dissolved in 30O 1 part of anhydrous dimethylformamide and heated to about 100 ° C. with 60 parts of stearyl isocyanate for 1 to 2 hours while stirring. Then the solvent is distilled off in vacuo. The sucrose stearylcarbamic acid diester is obtained in theoretical yield in the form of a very weak yellowish-colored product which can be used as a defoamer.
45 Beispiel 245 Example 2
35 Teile Saccharose werden in 300 Teilen wasserfreiem Dimethylformamid gelöst und mit 89 Teilen Stearylisocyanat 1 bis 2 Stunden auf etwa 100° C erhitzt. Nach dem Abdestillieren des Lösungsmittels im Vakuum erhält man den Saceharosestearylcarbamidsäuretriester in theoretischer Ausbeute in Form eines schwach gelblichgefärbten Produktes, das als Entschäumer verwendet werden kann.35 parts of sucrose are anhydrous in 300 parts Dissolved dimethylformamide and heated to about 100 ° C. with 89 parts of stearyl isocyanate for 1 to 2 hours. After the solvent has been distilled off in vacuo, the Saceharose stearylcarbamic acid triester is obtained in theoretical yield in the form of a pale yellowish product that acts as a defoamer can be used.
Verfahren zur Herstellung von Carbamidsäureestern von ZuckernProcess for the preparation of carbamic acid esters of sugars
Anmelder:Applicant:
Farbenfabriken Bayer Aktiengesellschaft, Leverkusen-BayerwerkPaint factories Bayer Aktiengesellschaft, Leverkusen-Bayerwerk
Dr. Georg Matthaeus, Leverkusen,Dr. Georg Matthaeus, Leverkusen,
und Dr. Mathieu Quaedvlieg, Leverkusen-Bayerwerk, sind als Erfinder genannt wordenand Dr. Mathieu Quaedvlieg, Leverkusen-Bayerwerk, have been named as inventors
150 Teile Saccharose werden in 500 Teilen wasserfreiem Dimethylformamid gelöst und mit 30 Teilen Stearylisocyanat 1 bis 2 Stunden unter Rühren auf etwa 100° C erhitzt. Dann wird das Dimethylformamid im Vakuum abdestilliert. In dem verbleibenden Rückstand befindet sich außer dem überschüssigen Zucker der Saccharosestearylcarbamidsäuremonoester neben geringen Anteilen an höheren Estern. Das so erhaltene Umsetzungsprodukt kann unmittelbar als Waschmittel benutzt werden.150 parts of sucrose are dissolved in 500 parts of anhydrous dimethylformamide and mixed with 30 parts Stearyl isocyanate heated to about 100 ° C. for 1 to 2 hours with stirring. Then the dimethylformamide distilled off in vacuo. In the remaining residue there is also the excess Sugar of the sucrose stearylcarbamic acid monoester in addition to small proportions of higher esters. That so reaction product obtained can be used directly as a detergent.
Eine Lösung von 500! Teilen Saccharose in 1300 Teilen wasserfreiem Dimethylformamid wird bei 100° C innerhalb einer Stunde mit 59 Teilen Stearylisocyanat versetzt. Nachdem die Lösung noch etwa 1 Stunde unter Rühren auf etwa 100° C erhitzt worden ist, wird sie filtriert, und das Dimethylformamid wird im Vakuum abdestilliert. In dem Rückstand befindet sich dann außer dem überschüssigen Zucker der Saccharosestearyloarbamidsäuremonoester, der als Waschmittel oder als Weichmachungsmitel für Textilien benutzt werden kann.One solution out of 500 ! Parts of sucrose in 1300 parts of anhydrous dimethylformamide are mixed with 59 parts of stearyl isocyanate at 100 ° C. over the course of one hour. After the solution has been heated to about 100 ° C. for about 1 hour while stirring, it is filtered and the dimethylformamide is distilled off in vacuo. In addition to the excess sugar, the residue contains the sucrose stearyloarbamic acid monoester, which can be used as a detergent or as a softener for textiles.
Claims (1)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF23597A DE1046010B (en) | 1957-07-26 | 1957-07-26 | Process for the preparation of carbamic acid esters of sugars |
| CH6178158A CH373370A (en) | 1957-07-26 | 1958-07-15 | Process for the preparation of carbamic acid esters of sugars |
| GB2377658A GB827358A (en) | 1957-07-26 | 1958-07-23 | Carbamide esters of sugars |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF23597A DE1046010B (en) | 1957-07-26 | 1957-07-26 | Process for the preparation of carbamic acid esters of sugars |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1046010B true DE1046010B (en) | 1958-12-11 |
Family
ID=7090908
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF23597A Pending DE1046010B (en) | 1957-07-26 | 1957-07-26 | Process for the preparation of carbamic acid esters of sugars |
Country Status (3)
| Country | Link |
|---|---|
| CH (1) | CH373370A (en) |
| DE (1) | DE1046010B (en) |
| GB (1) | GB827358A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1151500B (en) | 1957-08-05 | 1963-07-18 | Akad Wissenschaften Ddr | Process for the preparation of nonionic, surface-active monocarbamic acid esters of aliphatic polyhydroxy compounds |
-
1957
- 1957-07-26 DE DEF23597A patent/DE1046010B/en active Pending
-
1958
- 1958-07-15 CH CH6178158A patent/CH373370A/en unknown
- 1958-07-23 GB GB2377658A patent/GB827358A/en not_active Expired
Non-Patent Citations (1)
| Title |
|---|
| None * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1151500B (en) | 1957-08-05 | 1963-07-18 | Akad Wissenschaften Ddr | Process for the preparation of nonionic, surface-active monocarbamic acid esters of aliphatic polyhydroxy compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| GB827358A (en) | 1960-02-03 |
| CH373370A (en) | 1963-11-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0150769B1 (en) | Process for the production of polyisocyanates with a biuret structure | |
| EP0157088B1 (en) | Process for the preparation of polyisocyanates having a biuret structure | |
| EP0459125A1 (en) | Process for the preparation of diols containing perfluoroalkylrests and polyurethanes. | |
| DE1046010B (en) | Process for the preparation of carbamic acid esters of sugars | |
| DE883902C (en) | Process for the manufacture of cyclic urethanes | |
| DE2705053A1 (en) | PROCESS FOR THE PREPARATION OF POLYCARBAMOYL SULFONATES FROM POLYISOCYANATE, THE PRODUCTS CONTAINED THEREOF AND THEIR USE FOR THE TREATMENT OF FIBER MATERIALS | |
| DE1081873B (en) | Process for the preparation of carbamic acid esters of sugars | |
| US3086010A (en) | Carbamide esters of sugars | |
| DE1132118B (en) | Process for the preparation of bis (chloromethyl) carbamic acid chloride | |
| DE1127344B (en) | Process for the preparation of N-aryl-N'-hydroxyureas | |
| DE1668005A1 (en) | Isopropenylphenyl isocyanates and process for their preparation | |
| DE1138040B (en) | Removal of hydrolyzable chlorine and reduction of acidity from / or. of organic isocyanates | |
| CH453332A (en) | Process for the preparation of carbamic acid esters | |
| DE573192C (en) | Process for the preparation of detergents, wetting agents and dispersants | |
| DE1028565B (en) | Process for the production of vitamin A acetate | |
| DE845520C (en) | Process for the preparation of quaternary ammonium compounds | |
| DE950466C (en) | Process for the preparation of acylaminocarboxylic acid esters | |
| DE1277851B (en) | Process for the preparation of 2-chlorocarbonylphenyl isocyanates | |
| DE946710C (en) | Process for the preparation of N-disubstituted sulfamic acid chlorides | |
| DE1099523B (en) | Process for the preparation of acyl derivatives of citric acid esters | |
| AT239252B (en) | Process for the partial or complete carbamylation of dihydric alcohols or of their partially O-substituted derivatives | |
| AT222100B (en) | Process for the production of new acidic esters | |
| AT212305B (en) | Process for the preparation of new carboxylic acid esters of 4, 6-dinitro-2-sec. butylphenols | |
| DE1158499B (en) | Process for the production of isonitriles | |
| DE925045C (en) | Process for the production of water-soluble sulfuric acid esters of cellulose |