Chemistry of hydrocarbon compounds – Unsaturated compound synthesis – By addition of entire unsaturated molecules – e.g.,...
Patent
1995-11-16
1998-09-22
Bell, Mark L.
Chemistry of hydrocarbon compounds
Unsaturated compound synthesis
By addition of entire unsaturated molecules, e.g.,...
585527, 585530, 585532, C07C 202
Patent
active
058116192
DESCRIPTION:
BRIEF SUMMARY
BACKGROUND OF THE INVENTION
The subject-matter of the present invention is a method of production of improved purity light alpha defines by oligomerisation of ethylene by means of a specific catalyst (as described in French patent application no. 92/08658 of 9 Jul. 1992) of the Ziegler type, then destruction of said catalyst by injection of an amine followed by vapourisation of the effluent obtained.
More precisely, said catalyst is obtained by mixture: X is an atom of chlorine or bromide, Y is a radical selected from the group formed by RO.sup.- alkoxys, R.sub.2 N.sup.- aminos, and RCOO.sup.- carboxylates, where R is a hydrocarbyl radical having 1 to 30 carbon atoms, x and y can have whole values from 0 to 4 and z equals 0 or 0.5, the sum of x+y being equal to 4, ')C(OR.sub.1)(OR.sub.2) in which R.sub.1 ' and R.sub.2 ' are constituted by one atom of hydrogen or a hydrocarbyl radical having 1 to 30 carbon atoms, and R.sub.1 and R.sub.2 are hydrocarbon radicals having 1 to 30 carbon atoms, which R" is a hydrocarbyl radical having 1 to 6 carbon atoms, X is an atom of chlorine or bromine, and n is a number between 1 and 2.
This catalyst is thus obtained by mixture of a zirconium compound, such as for example zirconium tetrachloride, with an organic compound selected from the class of acetals and ketals, resulting from the condensation of an aldehyde or of a ketone with a monoalcohol or a polyalcohol, such as for example 2,2-bis(2-ethylhexyloxy)-propane, and with a chlorinated or brominated compound of aluminium hydrocarbyl, such as for example aluminiumethylsesquichloride.
The method according to the present invention proposes a specific method for destruction of the oligomerisation catalyst described hereinabove.
In an industrial implementation of a method of homogeneous catalysis, in addition to the management of the reaction itself, there is the problem of the separation and isolation of products from the raw reaction mixture, and in particular of the catalyst, which is totally soluble in the reaction mixture.
In the case of the ethylene oligomerisation reaction, two methods can be utilised to this end: precipitation and filtration or centrifuging, or by two-phase extraction, for example through water, 1-hexene, 1-octene, 1-decene and higher oligomers, which leaves the catalyst in the bottom of the distillation, still soluble, but concentrated in a fraction of heavy oligomers, as well as the polymer possibly produced as a secondary product.
Nevertheless, whatever the method used, it has been observed that in practice either the treatment with an aqueous phase or the prolonged contact between the oligomers and the catalyst in the reboilers of the distillation columns causes secondary reactions such as chlorination which are detrimental to the quality of the products. It is therefore desirable to destroy the activity of the catalyst beforehand, which can most often be carried out by addition of a base.
Thus the destruction of zirconium based ethylene oligomerisation catalysts by the addition of an anti-polymerisation reaction agent and of an amine at the end of the reaction has been described in U.S. Pat. No. 4,396,788, U.S. Pat. No. 4,434,312, U.S. Pat. No. 4,442,309 and U.S. Pat. No. 4,486,615 with the object of preventing the formation of connected secondary products, and in the case of EP 241 596 of preventing the formation of chlorinated by-products. The use of an aqueous solution of soda or ammonia together with or without the addition of an amine is mentioned in the patents described hereinabove as well as in EP 328 728 and JP03 103 406.
In EP 320 571, the product of the oligomerisation reaction is subjected to an operation separating the residual ethylene (called flashing), said operation being accompanied by precipitation of the polymer. The polymer is crushed and the mixture obtained is admixed with an amine so as to de-activate the catalyst. Distillation allows the olefinic compounds to be retrieved.
The decomposition of the ternary catalyst constituted by a mixture of a zirconium compound with a
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Commereuc Dominique
Glaize Yves
Hugues Francois
Saussine Lucien
Bell Mark L.
Hailey Patricia L.
Institut Francais du Pe'trole
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