US 6,720,303 B2 · Macrocyclic musk composition, organoleptic uses thereof and process for preparing same

Abstract

Described are mixtures consisting essentially of oxomacrocyclic compounds containing greater than about 40 weight % Δ3-cyclotetradecen-1-one and greater than about 40 weight % cyclotetradecanone and less than about 5 weight %, of Δ2-cyclo-tetradecen-1-one, perfumery uses thereof and chemo-selective catalytic hydrogen process for preparing same by hydrogenating mixtures containing significant concentrations, greater than 15 weight %, of Δ2-cyclotetradecen-1-one. The oxocarbocyclic compound-containing mixtures have advantageous musk aroma imparting, augmenting and enhancing perfumery properties causing the mixtures to be useful in perfume compositions, perfumed articles and perfumed polymers, including particles and fibers produced therefrom.

Claims15

Dependent claims

A macrocyclic musk composition of matter consisting essentially of:

(a) from about 40 up to about 60 weight % of cyclotetradecanone;
(b) from about 40 up to about 60 weight % of Δ3-cyclotetradecen-1-one;
(c) less than 5 weight % of Δ2-cyclotetradecen-1-one, the weight ratio of cyclotetradecanone:Δ3-cyclotetradecen-1-one being from about 6:4 down to about 4:6.

A process for preparing a macrocyclic musk composition comprising the steps of:

(a) admixing a cyclotetradecenone reactant mixture comprising greater than 45% by weight of Δ3-cyclotetradecen-1-one and greater than 15% by weight of Δ2-cyclotetradecen-1-one with a hydrogenation reaction solvent to form a solvent-reactant mixture with the weight ratio of solvent:cyclotetradecenone reactant mixture being from 20:70 up to 70:20;
(b) treating the resulting solvent-reactant mixture with hydrogen in the presence of a chemo-selective hydrogenation catalyst in a concentration of from about 0.1% up to about 0.5% by weight of the reaction mixture, at a temperature in the range of from about 15° C. up to about 35° C. and at a pressure of from about 0 psig up to about 100 psig thus forming a hydrogenated product reaction mass, whereby a composition comprising, on a solvent-free basis, greater than 40% by weight of cyclotetradecanone, greater than 40% by weight of Δ3-cyclotetradecen-1-one and less than 5% by weight of Δ2-cyclotetradecen-1-one is produced;
and
(c) recovering the resulting macrocyclic musk composition from the hydrogenated product reaction mass.

1 more element

Dependencies are inferred from the claim text.

Macrocyclic musk composition, organoleptic uses thereof and process for preparing same

Life of this patent

Macrocyclic musk composition, organoleptic uses thereof and process for preparing same

Life of this patent

Abstract

Claims15