Functionalized cyclopentene-derived oligomer mixtures, their preparation and their use

A process for preparing functionalized cyclopentene-derived oligomer mixtures by a single stage or multistage functionalization of at least some of the ethylenic double bonds present in an oligomer mixture of the formula I, R1R2C=[=CH-(CH2)3-CH=]n=CR3R4, where n is an integer from 1 to 15, and R1, R2,R3 and R4 are, independently of one another, hydrogen or straight-chain or branched C1-C15-alkyl, wherein the oligomer mixtures used for the functionalization are obtainable by a metathesis reaction of a hydrocarbon mixture comprising acyclic and cyclic olefins, and wherein said hydrocarbon mixture is a C5-hydrocarbon mixture with a total cyclopentene content of at least 5% by weight and a proportion of pentene isomers in the acyclic monoolefins of at least 70% by weight, and wherein the oligomer mixtures of formula I are subjected to a hydroformylation with carbon monoxide and hydrogen in the presence of a hydroformylation catalyst at a temperature in the range from 50 to 150 DEG C and a pressure of 10 to 650 bar, to obtain a hydroformylated oligomer mixture and where appropriate, further functionalizations, selected from: - reaction in the presence of an oxidizing agent, selected from atmospheric oxygen and combinations of aqueous hydrogen peroxide solutions with a carboxylic acid to obtain a cyclopentene-derived oligomer mixture with carboxy functionalities, - reaction with hydrogen in the presence of a Rancy nickel hydrogenation catalyst, at a temperature in the range from 80 to 150 DEG C and a pressure of 50 to 350 bar to obtain a cyclopentene-derived oligomer mixture with hydroxyl functionalities, - reaction with ammonia, or a primary or secondary amine in the presence of an amination catalyst and of hydrogen, wherein the catalyst has, in the non-reduced oxide form, a content of from 20 to 75% by weight of nickel oxide, 10 to 75% by weight of rinkonium dioxide, 5 to 50% by weight of copper oxide, optionally up to 5% by weight of molyb denium oxide and optionally up to 10% by weight of manganese oxide, and wherein the reductive animation is carried out at from 150 to 230 DEG C, under a pressure of from 150 to 250 bar.