Title of Invention

METHOD FOR PRODUCING MACROCYCLIC KETONES

Abstract

The present invention relates to a novel thermo-isomerization method for rapidly and simply producing macrocyclic ketones of the formula la or lb. The macrocyclic ketones are prepared in the gas phase at temperatures above 500°C rapidly and in a simple manner from alcohols of the formula IIa and IIb directly with a high yield. In the formulae la, lb, Ila and lib, Rl - R5, and n have the meanings given in the description.

Full Text

Claims (for India) 1. A method for producing macrocyclic ketones of the fornnula la, or lb comprising the steps: (a) converting at 100oC - 300oC into the gas phase a compound of formula lla or formula lib and (b) heating the compound of formula lla or formula lIb, converted into the gas phase under (a), to temperatures of from 500oC to 700oC, and (c) if R6 is a trialkylsilyl group, hydrolysis of the trialkylsilyl ether resulting under (b) into the corresponding ketone of the formula la or lb. A method according to claim 1, wherein R1, R2 and R3 are independently hydrogen or methyl and at least one of R1, R2 and R3 is methyl A method according to claim 1, characterized in that the compound formula lla or the compound of formula lib is dissolved in an inert solvent prior to be converted into the gas phase. A method according to claim 1, characterized in that the compound of formula lla or the compound of formula lib is converted into the gas phase continuously. A method according to claim 1, characterized in that the compound of formula lla or the compound of formula lib is converted into the gas phase at 120oC - 250oC. A method according to claim 1, characterized in that an inert gas is added to the gas phase of (a). A method according to claim 1, characterized in that the heating temperature of (b) is from 500oC to 670oC. A compound selected from the group consisting of 2-methylcyclotetradecanone, 3-methylcycloheptadecanone, 5-methylcycloheptadecanone, 3-methylcycloheptadecanone, 4-ethylcyclotetradecanone, and 3,4-dimethylcyclotetra decanone. A method for producing a compound of formula lla or a compound of formula lib R1, R2 and R3 are independently hydrogen, or a C1 to C6alkyI group, and R1 and R2 or R2 and R3 form together with the carbon atom(s) to which they are attached a ring; R4 is hydrogen, a linear or branched C1 to C4 alkyl group; n is an integer of 7 to 14; and R5 is hydrogen ,a trialkylsilyl group, or an alkali metal cation; comprising the step of (a) precomplexation of a macrocyclic ketone with an anhydrous Lewis acid at temperatures of from 0oC to 40°C, and (b) subsequent addition of organometallic alkylene compounds onto the precomplexed macrocyclic ketones under Grignard conditions, A compound selected of 1-vinyl-1-cycloundecanol, 1-vinyl-1-cyclotridecanol, 1-vinyl-1-cyclotetradecanol, 1 -vinyM -cyclopentadecanol, (syn/anti)-2-methyl-1 -vinyl-1 -cydododecanol, (syn/anti)-2-ethyl-1-vinyl-1-cyclododecanol, (syn/anti)-3-methyl-1"Vinyl-1-cyclopentadecanol, (E/Z)-1-(1-propen-1-yl)cyclododecanoL (E/Z)-1-(1-propenyl)cyclo tridecanol, (E/Z)-1 -(1 -propenyl)cyclotetradecanol, (E/Z)-1 -(1 -propen-1 -yl)cyclopentadecanol, 1-(1-methylethenyl) cydoundecanol, 1-(2-methyl-1-propenyl)cyclododecanol, (E/Z)-1-(2-buten--2-yl)cyclododecanol, (E/Z)-1-(trimethylsilyloxy)-1-(1-propenyl)cyclododecanol), and (E/Z)-2"methyl-1-(1-propen-1-yl)cyclododecanol. A compound selected of 1-ethynylcyclotridecanol and 1-(1-propynyl)cyclododecanol. 12. A method for producing macrocyclic ketones substantially as herein described and exemplified. 13. A compound substantially as herein described and exemplified.

Documents:

1294-chenp-2003 abstract original.pdf

1294-chenp-2003 claims granted.pdf

1294-chenp-2003-abstract.pdf

1294-chenp-2003-claims.pdf

1294-chenp-2003-correspondnece-others.pdf

1294-chenp-2003-correspondnece-po.pdf

1294-chenp-2003-description(complete).pdf

1294-chenp-2003-form 1.pdf

1294-chenp-2003-form 18.pdf

1294-chenp-2003-form 3.pdf

1294-chenp-2003-form 5.pdf

1294-chenp-2003-pct.pdf