Organic compounds -- part of the class 532-570 series – Organic compounds – Amino nitrogen containing
Patent
1998-11-05
2000-10-31
Barts, Samuel
Organic compounds -- part of the class 532-570 series
Organic compounds
Amino nitrogen containing
564485, C07C21300
Patent
active
061405418
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to a process for the preparation of polyalkeneamines from epoxides. The products prepared according to the invention are used in particular as fuel and lubricant additives.
Carburettors and intake systems of gasoline engines as well as injection systems for metering fuel in gasoline and diesel engines are increasingly being contaminated by impurities. The impurities are caused by dust particles from the air sucked in by the engine, uncombusted hydrocarbon residues from the combustion chamber and the crankcase vent gases passed into the carburettor.
These residues shift the air/fuel ratio during idling and in the lower part-load range so that the mixture becomes richer and the combustion more incomplete. Consequently, the proportion of uncombusted or partially combusted hydrocarbons in the exhaust gas and the gasoline consumption increase.
It is known that these disadvantages can be avoided by using fuel additives for keeping valves and carburettor or injection systems clean (cf. for example M. Rossenbeck in Katalysatoren, Tenside, Mineraloladditive, Editors J. Falbe and U. Hasserodt, page 223, G. Thieme Verlag, Stuttgart 1978). Depending on the mode of action and preferred place of action of such detergent additives, a distinction is now made between two generations. The first generation of additives was capable only of preventing the formation of deposits in the intake system but not of removing existing deposits. On the other hand, the additives of the second generation can prevent and eliminate deposits (keep-clean- and clean-up effect). This is permitted in particular by their excellent heat stability in zones of relatively high temperature, in particular in the intake valves.
The molecular structural principle of these additives of the second generation which act as detergents is based on the linkage of polar structures to generally higher molecular weight, nonpolar or oleophilic radicals. Typical members of the second generation of additives are products based on polyisobutene in the nonpolar moiety, in particular additives of the polyisobuteneamine type and of the polyisobutene amino alcohol type. Such detergents can be prepared starting from polyisobutenes, by various multistage synthesis processes.
Polyisobuteneamino alcohols are prepared by first epoxidizing polyisobutenes and then reacting the epoxide with the desired amine. Such processes catalyzed by homogeneous or heterogeneous catalysts are described, for example, in WO 92/12221, WO 92/14806, EP 0 476 485 and EP 0 539 821.
Polyisobuteneamines are obtained starting from polyisobutene, essentially by two processes.
The first process involves chlorination of the polymeric parent structure followed by nucleophilic substitution by amines or preferably ammonia. The disadvantage of this process is the use of chlorine, which results in the occurence of chlorine- or chloride-containing products, which is by no means desirable today and should if possible be avoided. For example, German Laid-Open Applications DE-OS 2,129,461 and DE-OS 2,245,918 describe the reaction of halogen-containing hydrocarbons with an amine compound in the presence of a hydrogen halide acceptor.
In the second process, the polyisobuteneamines are prepared starting from polyisobutene by hydroformylation and subsequent reductive amination. For example, EP 0 244 616 and German Patent 3,611,230 describe the carbonylation of polybutene or polyisobutene in the presence of a homogeneous catalyst, eg. cobalt octacarbonyl, and the subsequent conversion of the oxo product into the amine. The disadvantages of this process are the high level of technical complexity of the carbonylation of the reactive polyisobutene under high pressure conditions and the special measures for removing the homogeneous carbonylation catalyst.
It is an object of the present invention to provide a process for the preparation of polyalkeneamines which is simpler to carry out than the processes known to date and gives an essentially halide-free product. In particular, the novel process
REFERENCES:
patent: 3756793 (1973-09-01), Robinson
patent: 4832702 (1989-05-01), Kummer et al.
patent: 5124484 (1992-06-01), Brown et al.
patent: 5567845 (1996-10-01), Franz et al.
Blum Gerhard
Gunther Wolfgang
Melder Johann-Peter
Oppenlander Knut
Posselt Dietmar
Barts Samuel
BASF - Aktiengesellschaft
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