Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1990-09-04
1992-09-01
Morris, Patricia L.
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
548353, C07D23326, A61K 750, C11D 328
Patent
active
051440407
DESCRIPTION:
BRIEF SUMMARY
The invention relates to a process for the preparation of 1-(acylaminoalkyl)-2-imidazolines substituted in the 2 position of the general formula I ##STR2## in which
R is an alkylene radical of the formula --CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 CH.sub.2 --, --CH(CH.sub.3)CH.sub.2 -- or --CH(CH.sub.3)CH.sub.2 CH.sub.2 -- and R.sup.1 is a fatty acid radical of 7 to 25 C atoms.
Compounds of the formula I where R is ethylene and trimethylene are known and are required in particular for the preparation of the corresponding quaternized imidazolinium salts (cf. Kirk-Othmer, Encyclopedia of Chemical Technology, Third Edition, Volume 19, (1982), page 527), which in turn are important industrial surfactants. They are used in particular in the cosmetics and body care sector because they are mild and gentle to the skin. Compounds of the formula I where R is ethylene or trimethylene are also used in considerable amounts as components in the formulation of detergents and anti-corrosives.
To prepare the compounds of the formula I where R is ethylene and trimethylene, it is known to react a fatty acid of the general formula II of the formula III CH.sub.2 CH.sub.2 --). For complete conversion a stoichiometric molar ratio of fatty acid to dialkylenetriamine of 2.0:1 is necessary.
To prepare a compound of the formula I, for example by the typical Example 2 of the French patent specification 1,582,293, a mixture of behenic acid and diethylenetriamine is heated in a molar ratio of 2:1 in xylene in a nitrogen atmosphere under reduced pressure at 90.degree. to 100.degree. C. for 15 hours and, at the same time, the water of the reaction formed is distilled off azeotropically. The xylene is then distilled off under reduced pressure. Carrying out the reaction in xylene and the need to recover the xylene is complicated and makes the process more expensive, in particular as a result of the necessary work-up of the xylene-containing aqueous distillates formed.
For preparing compounds of the formula I where R is ethylene and trimethylene, it is also already known to react the fatty acid of the formula II and the dialkylenetriamine of formula III where R is ethylene and trimethylene without using a solvent. The difficulties of preparing compounds of the formula I by reacting fatty acids of the formula II with dialkylenetriamine of the formula III are in part due to the fact the reaction proceeds in two steps, in which first the dialkylenetriamine is acylated by the fatty acid and this intermediate is then converted to the compound of the formula I with ring closure, and due to the requirement that for an industrially useful process for the preparation of the compounds of the formula I, the yield of the compounds of the formula I must be high and only negligible amounts of the starting compounds and of possible acylation intermediates of the formulae IV to X ##STR3## and of other imidazoline compounds, for example those of the general formula XI ##STR4## must be present in the product obtained In the case where R is ethylene, the abovementioned formulae IV and V and VIII and IX are identical to one another.
The investigations by Raymond G Bistline, James W. Hampson and Warner M. Linfield in JAOCS, Vol. 60, No. 4, (April 1983), pages 823 to 828, in particular page 826, have disclosed that in the reaction of a fatty acid of the formula II with diethylenetriamine at a temperature of 90.degree. C. first a gelatinous amine soap is formed by salt formation, which upon heating to 130.degree. C. gives the acylation product of the abovementioned formula VI, from which then with further fatty acid upon heating at 150.degree. C. for 6 hours an intermediate of the abovementioned formula VIII is predominantly formed. This intermediate can then be converted by heating at 150.degree. C. under a reduced pressure of 0.2 mm Hg to the desired imidazoline of the formula I. At a total cyclization time of 8 hours, yields of 95% of the desired imidazoline of the general formula I are obtained in this process on a laboratory scale. Bistline et al. recommend
REFERENCES:
patent: 4709045 (1987-11-01), Kubo et al.
Chemical Abstracts, vol. 111, entry 7402b, 1989.
Eckhardt Georg-Wolfgang
Keil Karl-Heinz
Schrod Manfred
Cassella Aktiengesellschaft
Miltenberger Lenora
Morris Patricia L.
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