Organic compounds -- part of the class 532-570 series – Organic compounds – Amino nitrogen containing
Patent
1990-09-06
1992-04-07
Raymond, Richard L.
Organic compounds -- part of the class 532-570 series
Organic compounds
Amino nitrogen containing
5253338, 525379, C07C20926
Patent
active
051030616
DESCRIPTION:
BRIEF SUMMARY
This invention relates to a process for producing hydrocarbyl amines suitable for use as lube oil or gasoline additives.
Methods of producing nitrogen derivatives having long chain hydrocarbyl chains are well known. For instance GB-A-1172818 (Monsanto) describes a process for producing Schiff's bases by oxidising a polyolefin with ozone in the presence of an alcohol followed by conversion of the oxidation product to a carbonyl compound and reaction of the carbonyl compound after separation thereof from the ozonolysis products with an amine results in a Schiffs base.
This necessary separation and/or purification of the carbonyl compound from the ozonolysis products prior to reaction with an amine would appear to make the process commercially non-viable.
An alternative method is that described in EP-A-244616 (BASF AG) where a polybutene is subjected to a hydroformylation reaction and the resultant mixture of oxo products is subjected to either (a) a Mannich reaction or (b) a hydroamination reaction.
This reaction has the disadvantage that the hydroformylation product has a mixture of long chain aldehydes, ketones and long chain alcohols. Such a mixture of products, especially the presence of long chain alcohols, which are not separated prior to the Mannich reaction or hydroamination, give a complicated mixture of products.
Moreover, the long chain alcohols may have a deterimental effect on the aminated end product when used eg. as lube oil additives or gasoline additives.
It has now been found that the problems associated with such prior art process can be mitigated by (a) avoiding the separation steps of the GB-A-1172818 and also the hydroformylation step of E-A-244616.
Accordingly, the present invention is a process for producing long chain alkyl amines from polyolefins, said process comprising reacting ozone in the presence of a solvent, isolation of the carbonyl compounds formed therein with a primary hydrocarbyl amines to form an imine, hydrogenation catalyst, and formed in step (c).
The polyolefin which is ozonolysed is suitably a polymer of a C.sub.2 -C.sub.4 olefin or a copolymer thereof and has a molecular weight in the region of 330-2000, preferably from 500 to 1500. Of these, polybutenes, especially those containing significant proportions of polyisobutene i.e. Hyvis, Napvis and Ultravis (all Registered Trade Marks, ex BP Chemicals) are preferred.
The ozonolysis of the polyolefin in step (a) above is suitably carried out by bubbling ozone in the gaseous phase, with or without an additional diluent, through a solution of the polyolefin in a solvent. Examples of solvents that may be used include alcohols and hydrocarbons, preferably aliphatic, straight chain alcohols which have 1-12 carbon atoms in the chain. In the case of alcohols, these preferably have 1-4 carbon atoms in the chain.
The ozonolysis temperature is suitably from -70.degree. to +50.degree. C., preferably -30.degree. to +30 .degree. C., and most preferably from -10.degree. to +30 .degree. C. The reaction is exothermic and hence care should be taken to ensure that the reaction temperature does not exceed 50.degree. C., if necessary by cooling.
The solvent is suitably present in the reaction mixture in a weight ratio of 1:1 to 10:1 with respect to the polyolefin reactant.
For this reaction it is essential to ensure that the proportion of ozone to olefin reacted at a given temperature and pressure are such that no explosive mixtures are formed. The explosive limits for the various reaction conditions are well known to those skilled in the art.
The ozonolysis products from step (a) are contacted with a primary amine in step (b). For this step the ozonolysis products are used directly, i.e. without any prior separation step, for reaction with the primary amine. Prior to contact of the ozonolysis products with the primary amine, it is preferable to (i) remove any excess ozone therein by sparging an inert gas eg. nitrogen therethrough and (ii) to wash the ozonolysis products with water in order to remove any lower boiling fractions such as e
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Blackborow John R.
Peretti Regis
BP Chemicals Limited
Rand Scott C.
Raymond Richard L.
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