Process for the preparation of N-alkanoyl-polyhydroxyalkylamines

Details Process for the preparation of N-alkanoyl-polyhydroxyalkylamines Process for the preparation of N-alkanoyl-polyhydroxyalkylamines

1995-04-24

1996-07-23

Dees, Jos e G.

Organic compounds -- part of the class 532-570 series

Organic compounds

Fatty compounds having an acid moiety which contains the...

554 66, 554 68, C07C23100

Patent

active

055391346

DESCRIPTION:

BRIEF SUMMARY
THIS APPLICATION IS A 371 OF PCT1/EP93/02852.



BACKGROUND OF THE INVENTION

1. Field of the Invention
The present invention relates to an improved process for the preparation of N-alkanoyl-polyhydroxyalkylamines by the reaction of polyhydroxyalkylamines with alkyl carboxylates in the presence of a basic catalyst.
2. Discussion of the Background
N-alkanoyl-polyhydroxyalkylamines, which are mainly used as surface-active agents in detergent and cleaner formulations, have been known in the art for many years and are frequently prepared from the aforementioned starting materials.
Thus U.S. Pat. No. 2,703,798 (1) teaches the reaction of N-monoalkylglucamines with aliphatic esters of fatty acids at temperatures of from 140.degree. to 230.degree. C.; in this method, the components are placed together in the reaction vessel before the reaction is started by heating.
EP-A 285,768 (2) reveals that the reaction of fatty acids or fatty acid esters with optionally N-substituted polyhydroxyalkylamines can be carried out in the melt, optionally in the presence of alkaline catalysts; a typical example is the preparation of N-methyl coconut fatty acid glucamide from the methyl ester of coconut fatty acid and N-methylglucamine by adding sodium methylate and heating the two components to 135.degree. C.
WO 92/06,071 (3) relates to a process for the manufacture of surface-active linear glucamides from N-alkylglucamines and fatty acid esters in which certain phase-transfer catalysts are added; first of all, a two-phase mixture is prepared by heating and intermixing the two components, and the reaction is then started by the addition of the catalyst and is subsequently carried out at temperatures of from 120.degree. to 200.degree. C.
WO 92/06,073 (4) reveals that it is possible to prepare polyhydroxy fatty acid amides from N-alkyl-polyhydroxyamines and fatty acid esters in a hydroxyl group-containing or alkoxylated solvent such as methanol, propylene glycol or an ethoxylated alcohol in the presence of a basic catalyst at temperatures of from 40.degree. to 100.degree. C.
A disadvantage of the prior art processes is that the product obtained usually contains a high proportion of starting material and by-products; this particularly applies to the processes disclosed in (1) to (3). When use is made of organic solvents as described in (4) these must be removed from the reaction mixture, on completion of the reaction, in an uneconomical manner, ie, by distillation; in addition to the extra energy costs incurred by separation there may also ensue environmental problems connected with the purification or disposal of these solvents.
Another disadvantage of the prior art processes is frequently the tendency of the reaction mixture to form lumps or to stick to the walls of the reactor, which makes it more difficult to maintain the reaction conditions and thus to reproduce the properties of the product and also entails problems concerning cleaning of the reactor.
It is thus an object of the present invention to overcome the above drawbacks of the prior art.


DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

Accordingly, we have found a process for the preparation of N-alkanoyl-polyhydroxyalklamines of the general formula I ##STR3## in which z stands for the polyhydroxyalkyl radical of a monosaccharide or oligosaccharide, ##STR4## in which R.sup.3 denotes a C.sub.1 -C.sub.4 alkyl radical, in the presence of a basic catalyst, wherein reaction temperature, and the amine II is metered in in the form of a melt while the reaction proceeds, whilst alcohol R.sup.3 --OH formed is continuously removed by distillation, 110.degree. C., and when these organic solvents assume the function of dispersing agents.
The process of the invention is carried out in accordance with proviso (a) as follows: the total amount of the ester IIl is placed in a reactor and is heated to the temperature required for the reaction. Thereafter the amine II is metered in portionwise or preferably continuously at such a rate that the temperature in the reactor remains constan

REFERENCES:
patent: 5338487 (1994-08-01), Conner et al.

Affiliated with

Also associated with

Rating

Process for the preparation of N-alkanoyl-polyhydroxyalkylamines does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Process for the preparation of N-alkanoyl-polyhydroxyalkylamines, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Process for the preparation of N-alkanoyl-polyhydroxyalkylamines will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-714314