Method of preparing benzyl alcohols by decarbonylation of formic acid esters

Claim 3

A method according to claim 1 wherein the formic acid ester to be decarbonylated is a formic acid ester of the general formula ##STR2## which are mono- or polysubstituted on the benzene ring and in which the substituents are as follows: Y is halogen or alkyl and n is 0 to 5; W is --CH 2 --O--CHO and a is 0 to 5; Z is hydroxy and/or alkoxy and/or phenoxy and b is 0 to 3; A is nitrile and c is 0 to 2; and a+b+n+c=1 to 5.

Claim 4

A method according to claim 2 wherein a+b+n+c=1 to 3.

Claim 5

A method according to claim 2 wherein Y is chloro or bromo or a C 1 -C 8 alkyl group and n is 0 to 2.

Claim 6

A method according to claim 2 wherein W is --CH 2 --O--CHO and a is 0 to 2.

Claim 7

A method according to claim 2 wherein Z is hydroxy or methoxy or phenoxy and b is 0 to 2.

Claim 8

A method according to claim 2 wherein A is a nitrile group and c is 0 to 2.

Claim 9

A method according to claim 1 wherein the formic acid ester is a mono- or disubstituted benzyl formiate, the substituents on the phenyl ring being of the group consisting of halogen, alkyl, alkoxy, phenoxy or formoxymethyl, the substituents being the same or different from one another when the phenyl ring is disubstituted.

Claim 10

A method according to claim 1 wherein the catalyst has the formula Me R.sub.m II wherein Me represents a metal of Group I to Group III of the Periodic System, m represents 1 to 3, and R has any of the following meanings: (a) --OR 1 where R 1 represents a linear or branched alkyl moiety having 1 to 8 carbon atoms or an aryl moiety or an aralkyl moiety; (b) an alkyl moiety having 1 to 8 carbon atoms or an aryl moiety or an aralkyl moiety or an amino group or hydrogen; (c) --OR 2 OH where R 2 is a linear or branched alkylene moiety having 2 to 8 carbon atoms or an o-, m- or p-xylylene moiety or an o-, m- or p-phenylene moiety or a naphthylene moiety; (d) where Me is an alkali metal, R is --OR 2 OMe where R 2 is a linear or branched alkylene moiety having 2 to 8 carbon atoms or an o-, m- or p-xylylene moiety or an o-, m- or p-phenylene moiety or a naphthylene moiety.

Claim 11

A method according to claim 9 wherein R has the meaning --OR 1 where R 1 is a linear or branched alkylene moiety having 1 to 4 carbon atoms or phenyl or a phenyl C 1 -C 8 alkyl moiety.

Claim 12

A method according to claim 9 wherein R is an alkyl moiety of 1 to 4 carbon atoms, phenyl, a phenyl C 1 -C 8 alkyl moiety, an amino group or hydrogen.

Claim 13

A method according to claim 9 wherein R has the meaning --OR 2 OH where R 2 is a linear or branched alkylene moiety of 2 to 4 carbon atoms, an o-, m- or p-xylylene moiety, an o-, m- or p-phenylene moiety or a naphthylene moiety.

Claim 14

A method according to claim 9 wherein Me is an alkali metal and R has the meaning --OR 2 OMe where R 2 is a linear or branched alkylene moiety of 2 to 4 carbon atoms, an o-, m- or p-xylylene moiety, an o-, m- or p-phenylene moiety or a naphthylene moiety.

Claim 15

A method according to claim 9 wherein the decarbonylation catalyst is a lithium-, sodium-, potassium-, magnesium- or calcium-methylate, -ethylate, -tertiary butylate, -benzylate, -xylylene glycolate or -phenolate.

Claim 16

A process according to claim 9 wherein the decarbonylation catalyst is a lithium-, sodium-, potassium-, calcium-, or aluminim-hydride.

Claim 17

A process according to claim 9 wherein the decarbonylation catalyst is a lithium-, sodium- or potassium-butyl, -phenyl or -naphthyl.

Claim 18

A process according to claim 1 wherein the decarbonylation catalyst is a Grignard compound.

Claim 19

A process according to claim 1 wherein the decarbonylation catalyst is an alkali metal.

Claim 20

A process according to claim 18 wherein said alkali metal is sodium or potassium.

Claim 21

A process according to claim 1 wherein the decarbonylation catalyst is present in an amount of 0.01 to 10 weight percent, based upon the amount of formiate to be decarbonylated.

Claim 22

A process according to claim 20 wherein said decarbonylation catalyst is present in an amount of 0.05 to 5 weight percent, with respect to the formiate to be decarbonylated.

Claim 23

A process according to claim 1 wherein the decarbonylation is carried out at a temperature of 20° to 250° C.

Claim 24

A process according to claim 22 wherein decarbonylation is performed at a temperature of 30° to 220° C.

Claim 25

A process according to claim 1 wherein the formiate is decarbonylated in a heterogeneous reaction mixture in the absence of a solvent.

Claim 26

A process according to claim 1 wherein the formiate is decarbonylated in the presence of an inert reaction medium and in the presence of a solvent.

Claim 27

A process according to claim 1, wherein the decarbonylation is carried out in the melt and carbon monoxide is withdrawn from the reaction mixture.

Claim 28

A process according to claim 1, wherein the decarbonylation is carried out in the presence of a tertiary alcohol and carbon monoxide is withdrawn from the reaction mixture.

Claim 29

A process according to claim 1, wherein the decarbonylation is carried out at a temperature of 20° to 250° C.

Claim 30

A process according to claim 28, wherein the decarbonylation is carried out at a temperature of 30° to 220° C.

Claim 31

A process according to claim 1, wherein said solvent is p-xylylene glycol.

Claim 32

A process according to claim 1, wherein said solvent is m-xylylene glycol.

Claim 33

A process according to claim 1, wherein the process is carried out in the presence of an alcohol corresponding to the formic acid ester reactant.