DE1081873B - Process for the preparation of carbamic acid esters of sugars - Google Patents
Process for the preparation of carbamic acid esters of sugarsInfo
- Publication number
- DE1081873B DE1081873B DEF28904A DEF0028904A DE1081873B DE 1081873 B DE1081873 B DE 1081873B DE F28904 A DEF28904 A DE F28904A DE F0028904 A DEF0028904 A DE F0028904A DE 1081873 B DE1081873 B DE 1081873B
- Authority
- DE
- Germany
- Prior art keywords
- carbamic acid
- acid esters
- sugars
- preparation
- sugar
- 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
- 229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 0.000 title claims description 10
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 title claims description 10
- 238000000034 method Methods 0.000 title claims description 6
- 150000008163 sugars Chemical class 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 3
- -1 alkyl isocyanates Chemical class 0.000 claims description 5
- 239000012948 isocyanate Substances 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- QIZPVNNYFKFJAD-UHFFFAOYSA-N 1-chloro-2-prop-1-ynylbenzene Chemical compound CC#CC1=CC=CC=C1Cl QIZPVNNYFKFJAD-UHFFFAOYSA-N 0.000 description 2
- 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
- 239000003599 detergent Substances 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229940035023 sucrose monostearate Drugs 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- QWDQYHPOSSHSAW-UHFFFAOYSA-N 1-isocyanatooctadecane Chemical compound CCCCCCCCCCCCCCCCCCN=C=O QWDQYHPOSSHSAW-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose 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)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products 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 1
- MUPFEKGTMRGPLJ-RMMQSMQOSA-N Raffinose Natural products O(C[C@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O[C@@]2(CO)[C@H](O)[C@@H](O)[C@@H](CO)O2)O1)[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 MUPFEKGTMRGPLJ-RMMQSMQOSA-N 0.000 description 1
- 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 1
- 229930006000 Sucrose Natural products 0.000 description 1
- MUPFEKGTMRGPLJ-UHFFFAOYSA-N UNPD196149 Natural products OC1C(O)C(CO)OC1(CO)OC1C(O)C(O)C(O)C(COC2C(C(O)C(O)C(CO)O2)O)O1 MUPFEKGTMRGPLJ-UHFFFAOYSA-N 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
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
- 239000013530 defoamer Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- BXXLBMBLLVIOKO-UHFFFAOYSA-N octadecylcarbamic acid Chemical compound CCCCCCCCCCCCCCCCCCNC(O)=O BXXLBMBLLVIOKO-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- MUPFEKGTMRGPLJ-ZQSKZDJDSA-N raffinose 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[C@@H]2[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO)O2)O)O1 MUPFEKGTMRGPLJ-ZQSKZDJDSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229960004793 sucrose Drugs 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Saccharide Compounds (AREA)
Description
Verfahren zur Herstellung von Carbamidsäureestern von Zuckern Gegenstand des Patents 1046 010 ist ein Verfahren zur Herstellung von Carbamidsäureestern von Zuckern, das darin besteht, daß man Zucker, beispielsweise Rohrzucker, Malzzucker, Milchzucker oder Raffinose, mit Alkylisocyanaten umsetzt, die im Alkylrest mehr als 8 Kohlenstoffatome enthalten, beispielsweise mit Stearylisocyanat. Die so hergestellten Carbamidsäureester der Zucker besitzen wertvolle oberflächenaktive Eigenschaften und können als Waschmittel, als Weichmachungsmittel für Textilien sowie insbesondere als Entschäumer verwendet werden.Process for the production of carbamic acid esters of sugars The subject of patent 1 046 010 is a process for the production of carbamic acid esters of sugars, which consists in reacting sugar, for example cane sugar, malt sugar, lactose or raffinose, with alkyl isocyanates which have more than 8 in the alkyl radical Contain carbon atoms, for example with stearyl isocyanate. The sugar carbamic acid esters produced in this way have valuable surface-active properties and can be used as detergents, as softeners for textiles and, in particular, as defoamers.
Gegenstand der Erfindung ist nun eine weitere Ausbildung des Verfahrens zur Herstellung von Carbamidsäureestern von Zuckern gemäß Patent 1046 010, die darin besteht, daß man an Stelle der Zucker ihre noch reaktionsfähige Hydroxylgruppen enthaltenden Derivate, z. B. ihre Fettsäureester, mit Alkylisocyanaten umsetzt, die im Alkylrest mehr als 8 Kohlenstoffatome enthalten. Die so erhältlichen #'--arbamidsäureester der Zuckerderivate besitzen ebenfalls wertvolle oberflächenaktive Eigenschaften und können gleichfalls als Waschmittel oder als Weichmachungsmittel für Textilien sowie insbesondere als Entschäumer verwendet werden.The invention is now further embodiment of the method for the preparation of carbamic acid esters of sugars according to Patent 1,046,010, which consists in that in place of the sugar still their reactive derivatives containing hydroxyl groups such. B. reacts their fatty acid esters with alkyl isocyanates which contain more than 8 carbon atoms in the alkyl radical. The #′-arbamic acid esters of the sugar derivatives obtainable in this way also have valuable surface-active properties and can likewise be used as detergents or as softeners for textiles and, in particular, as defoamers.
Die Umsetzung der noch reaktionsfähige Hydroxylgruppen enthaltenden Zuckerderivate mit den Alkylisocyanaten erfolgt wie bei dem Verfahren des Hauptpatents zweckmäßig unter Erhitzung in indifferenten Lösungsmitteln, z. B. in Dimethylformamid. Geeignete Mengenverhältnisse der miteinander umzusetzenden Komponenten lassen sich durch Vorversuche leicht ermitteln; sollen Carbamidsäureester von Zuckerderivaten hergestellt werden, die nur einen Alkylcarbamidsäurerest enthalten, so wendet man die Zuckerderivate zweckmäßig im Überschuß an, sollen jedoch Carbamidsäureester von Zuckerderivaten hergestellt werden, die zwei oder mehr Alkylcarbamidsäurereste enthalten, so setzt man die Komponenten zweckmäßig in entsprechenden molaren Verhältnissen ein.The implementation of the still reactive hydroxyl groups Sugar derivatives with the alkyl isocyanates are carried out as in the process of the main patent expediently with heating in inert solvents, eg. B. in dimethylformamide. Suitable proportions of the components to be reacted with one another can be determined easily determined by preliminary tests; are said to be carbamic acid esters of sugar derivatives are produced which contain only one alkyl carbamic acid residue, one turns the sugar derivatives expediently in excess, but should be carbamic acid esters are made from sugar derivatives containing two or more alkyl carbamic acid residues contained, the components are expediently used in appropriate molar ratios a.
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 gleich den Carbamidsäureestern des Hauptpatents durch eine stärkere Oberflächenaktivität aus.Compared to the well-known sugar esters, which are made by converting sugars available with fatty acids or with esters from fatty acids and lower alcohols the carbamic acid esters of the invention are distinguished from the carbamic acid esters of the main patent is characterized by a stronger surface activity.
Die in dem nachfolgenden Beispiel angegebenen Teile sind Gewichtsteile. Beispiel Eine Lösung von 31 Teilen Saccharosemonostearat in 400 Teilen wasserfreiem Dimethvlformamid wird wird bei 100 bis 110° C mit 14,7 Teilen Stearyliso-. cyanat versetzt und anschließend 1 Stunde bei dieser Temperatur gerührt. Hierauf wird das Lösungsmittel entfernt. Man erhält dann den Stearylcarbamidsäuremonoester des Saccharosemonostearats in Form eines fast weißen Pulvers, das aus Alkohol umkristallisiert werden kann. Das so erhaltene Umsetzungsprodukt kann als Entschäumer verwendet werden.The parts given in the following example are parts by weight. Example A solution of 31 parts of sucrose monostearate in 400 parts of anhydrous Dimethvlformamid is at 100 to 110 ° C with 14.7 parts of stearyliso-. cyanate added and then stirred for 1 hour at this temperature. Then that will Solvent removed. The stearyl carbamic acid monoester of sucrose monostearate is then obtained in the form of an almost white powder that can be recrystallized from alcohol. The reaction product obtained in this way can be used as a defoamer.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1081873X | 1958-07-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1081873B true DE1081873B (en) | 1960-05-19 |
Family
ID=4556441
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF28904A Pending DE1081873B (en) | 1958-07-15 | 1959-07-11 | Process for the preparation of carbamic acid esters of sugars |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1081873B (en) |
-
1959
- 1959-07-11 DE DEF28904A patent/DE1081873B/en active Pending
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