Combined synthesis of a nitrile-ester/acid and of a diester/diacid

摘要

A method for the combined synthesis of a mono-unsaturated nitrile-ester(acid) and of a bi-functional carbonyl compound, wherein it includes a step including the cross metathesis mc1 of an unsaturated fatty acid/ester compound with an unsaturated nitrile compound, in which mc1 is performed with partial conversion such as to obtain and recover, separately, at least the following products: a mono-unsaturated nitrile-ester/acid and a symmetrical compound, diester or diacid respectively including a double bond located in the middle of the molecular chain of compound, and subsequently a step including the oxidation cleavage cp2 of the double bond of compound, such as to form a single type of carbonyl compound having formula R2-(CH2)n-COR′, in which R′ is H or OH, depending on the operating conditions selected for the oxidation cleavage cp2. Also, the production of monomers for the polymer industry.

主权项

1. A process for the conjugate synthesis of a monounsaturated nitrile ester (acid) and of a difunctional carbonyl compound (V), of formula R2—(CH2)n—COR′ in which R′ is H or OH, from the same unsaturated fatty compound (I) comprising at least one ester or acid function, respectively, of formula:
R1—CH═CH—[(CH2)q—CH═CH]p—(CH2)n—R2   (I) in which R1 is H or an alkyl radical comprising from 1 to 4 carbon atoms, R2 is an ester or acid function and n, p and q are integers such that 3≦n≦13; 0≦p≦3; 0≦q≦1, wherein the process comprises: a step of cross metathesis cm1 of compound (I) with an unsaturated nitrile compound (II) chosen from: acrylonitrile, fumaronitrile, 2-butenenitrile, 1-butenenitrile, 2-pentenenitrile, 3-pentenenitrile, 4-pentenenitrile and 1-pentenenitrile, in which cm1 is brought to partial conversion so as to obtain, and to recover separately, at least the following products: a monounsaturated acid (ester)-nitrile (Ill) and a symmetrical compound (IV), respectively a diester or diacid comprising a double bond located in the middle of the molecular chain of compound (IV) of formula R2—(CH2)n—HC═CH—(CH2)n—R2 resulting from the homometathesis of compound (I), and then a step of oxidative cleavage cl2 of the double bond respectively of the diester or diacid compound (IV), so as to form a single type of carbonyl compound (V) of formula R2—(CH2)n —COR′ in which R′ is H or OH, depending on the operating conditions chosen for the oxidative cleavage cl2, in which the cross metathesis step is performed to a degree of conversion in the range from 30% to 90%.