DE1265738C2 - PROCESS FOR THE PRODUCTION OF CARBAMIC ACID ESTERS OF ALIPHATIC POLYHYDROXY COMPOUNDS - Google Patents

Description

FEDERAL REPUBLIC OF GERMANY Int. CL;

COTc- US / 06

GERMAN

PATENT OFFICE

PATENT LETTERING

Detitsche Kl .: 12 ο -17/01

number

File number:

Registration date:

Display day:

Issue date:

P 12 65 738.4-42 (D 49251)

January 31, 1966

April 11, 1968

4th January 1973

The patent specification differs from the patent specification

The invention UcUiHt a further training of the Process / for the production of carbarnineal esters aliphatic polyhydroxy compounds according to patent

IO Ό CM

In the main patent, carbamic acid esters are aliphatic through polyhydroxy compounds l'msct / en of aliphatic polyhydroxy compounds with alkali metal and higher molecular alkyl halides. especially chlorides and bromides, prepared by reacting with aliphatic Hydroxyl groups in the molecule, especially sugars, polyhydroxy compounds with three to fifteen and their derivatives, in the presence of dimethyltormamide as a solvent and triethylamine as a catalyst at temperatures of 60 to 153 ° C performs.

These carbamic esters of the general formula R NH - CO - OR ₁ , in which R _{1 is} an aliphatic polyhydroxy group and R is an aliphatic radical, show a decreasing solubility as the number of carbon atoms in the aliphatic radical R increases.

It has now been found that carbamic acid esters of aliphatic polyhydroxy compounds can be used with greater solubility can be obtained by the process of the main patent application if you have the Implementation instead of with alkyl halides with halogen fatty acid esters and optionally the Carboxylic ester group of the product obtained saponified in the usual way.

Suitable Halogenfettsäureester are "bromo-caprylsäuremethylester, · χ - bromo-myristate, <·> - bromoundecanoate, 11 - Bromstearinsäuremethylester or mixtures thereof.

The implementation takes place according to the following equation

Hal R, -CO-OR + KNCO <HO-R ₁ - * R ₁ O-Ut-NH-R ₅ -CO-OR: KHaI

where R is a low molecular weight alkyl radical, R _{1 is} an aliphatic polyhydroxy group, R _{2 is} a higher molecular weight straight-chain or branched alkyl radical and Hal is a halogen atom, preferably a bromine or chlorine atom.

The carbamic acid esters obtained can be converted to the corresponding carbamic acid esters in a customary manner are saponified, which can be used as wetting and cleaning agents, as they are very good Have surface and washing-active properties.

Process for the production of
Carbamic acid esters more aliphatic
Polyhydroxy compounds

Addition to the patent: 1 250 808

The main patent started on

February 3, 1965

Patented for:

German Academy of Sciences in Berlin, X 1199 Berlin-Adlershof, Rudower Chaussee 5

Named as sponsor:
Dipl.-Chem. Dr. Werner Gerhardt,
X 1199 Berlin-Adlershof

The following examples illustrate the process of the invention.

example 1

200 g (0.6 mol) of dried sucrose are dissolved in anhydrous dimethylformamide, 50 g (0.6 mol) of potassium cyanate are added and g (0.5 mol) of methyl bromocaprylate are slowly run in at about 75.degree . When the reaction has ended (recognizable by the KBr which has precipitated out), the mixture is stirred at the same temperature for 1 hour. It is allowed to cool, the separated salts (KBr) are filtered off and the dimethylformamide is stripped off as completely as possible under reduced pressure. 371 g of N- [1-carbomethoxyheptylj-sucrose urethane (mixture of isomers) are obtained. This is taken up in 1 liter of water and the solution is extracted twice with a mixture of butanol and hexane. After distilling off the butanol-hexane mixture in vacuo and drying, 246 g (90 ° / ₀ of theory) of colorless N- [1-Carbomethoxyheptyl] -sacchäföseurethan (mixture of isomers) that softens by recrystallization from acetone at 102 to 106 ⁰ C. .

The potassium salt of N-II-carboxyheptyl-sucrose urethane is obtained by saponification with aqueous potassium hydroxide solution (Isomer mixture) obtained in quantitative yield as a white powder. It can be recrystallized Clean again from alcohol.

Ö e i s ρ i c I 2

200 g of sucrose with 50 g of potassium cyanate and 167.5 g of ethyl bromomyrisylate are cntsprc-

accordingly to Example 1 implemented and worked up

This gives 254 g (78% of theory) of N- [1-carb Sthoxytridecyll-saccharoseurethan (mixture of isomers) from the softening point 104 to 110 ⁰ C.

The saponification with aqueous sodium hydroxide solution results the sodium salt of N- [1-carboxytridecyl] sucrose urethane (Mixture of isomers) in quantitative yield. It can be recrystallized from alcohol to clean.

Claims (1)

Claim: Further development of the process for the preparation of Carbanünäureestern sdiphatic polyhydroxy compounds by reacting aliphatic polyhydroxy compounds with three to fifteen hydroxyl groups in the molecule, especially sugar and their derivatives, with alkali metal cyanates and higher molecular weight alkyl halides, especially chlorides and bromides, in the presence of dimethylformamide as the solvent and of triethylamine as Catalyst at tempe-. arturen 60-153 ^Q C according to Patent 1,250,808, characterized in that one carries out the reaction takes with alkyl halides with Halogenfettsäureestern saponified and optionally the Carbo'nsäureestergruppe of the product obtained in the conventional manner.