Process for the preparation of aromatic dicarboxylic acids and aromatic hydrocarbons
AssigneeBayer Aktiengesellschaft
InventorsRichard Weider, Thomas Scholl
Life of this patent
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Abstract
Aromatic dicarboxylic acids of the formula ##STR1## in which R.sup.1, R.sup.2, m, n, and X have the meaning mentioned in the description, can be prepared from the bisphenols, on which they are based, of the formula ##STR2## if the bisphenols are first reacted to give the bissulphonates, the sulphonate groups are removed catalytically with H.sub.2 and the hydrocarbons obtained in this way are doubly acylated in a known manner and the acyl groups are oxidized to the carboxyl groups. Many of the aromatic dicarboxylic acids which can be prepared in this way are new.
Claims16
A process for the preparation of an aromatic dicarboxylic acid of the formula
- in which
- X denotes a single bond, C.sub.1 -C.sub.12 -alkylene, C.sub.5 -C.sub.15 -cycloalkylene, oxygen, sulphur,
- or the group ##STR20## R.sub.1 and R.sub.2, independently of one another denote straight-chain or branched C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy and
- m and n, independently of one another, represent integers from 0 to 4,
- wherein
- a) a bisphenol of the formula ##STR21## in which R.sub.1, R.sub.2, m, n and X have the meaning mentioned,
- is reacted with a sulphonic acid derivative of the formula
- R.sub.3 --SO.sub.2 --R.sub.4
- in which
- R.sub.3 represents straight-chain or branched C.sub.1 -C.sub.12 -alkyl, C.sub.3 -C.sub.8 -cycloalkyl, C.sub.6 -C.sub.12 -aryl or C.sub.7 -C.sub.10 -aralkyl and
- R.sub.4 is OH, Cl, Br or O-O.sub.2 S-R.sub.3,
- to give a bissulphonate of the formula ##STR22## in which R.sub.1, R.sub.2, R.sub.3, m, n and X have the meaning mentioned,
- b) the bissulphonate obtained is hydrogenated in dissolved form at an H.sub.2 pressure of 1 to 100 bar on a support-containing or support-free hydrogenation catalyst in an amount of from 0.5 to 10 g of hydrogenation-active component per mole of bissulphonate to give the corresponding hydrocarbon of the formula ##STR23## in which R.sub.1, R.sub.2, x, m and n have the meaning mentioned, and
- c) the hydrocarbon obtained is doubly acylated and the acyl groups are oxidized to carboxyl groups.
An aromatic dicarboxylic acid of the formula ##STR25## in which X denotes a moiety selected from the group consisting of the formulae ##STR26## and the group ##STR27## R.sub.1 and R.sub.2, independently of one another, denote straight-chain or branched C.sub.1 -C.sub.4 -alkyl and
- q and r, independently of one another, represent integers from 0 to 4, a dichloride or a di-C.sub.1 -C.sub.4 -alkyl ester of the dicarboxylic acid.
An aromatic dicarboxylic acid selected from the group consisting of 2,2-bis-(3,5-dimethyl-4-carboxyphenyl)-propane, 1,1-bis-(4-carboxyphenyl)-cyclohexane, 1,1-bis-(4-carboxyphenyl)-3-methyl-cyclohexane and 1,1-bis-(4-carboxyphenyl)-3,5,5-trimethyl-cyclohexane.
A process for the preparation of an aromatic hydrocarbon of the formula ##STR28## in which X denotes a single bond, C.sub.1 -C.sub.12 -alkylene, C.sub.5 -C.sub.15 -cycloalkylene, oxygen, sulphur,
- or the group ##STR29## R.sub.1 and R.sub.2, independently of one another, denote straight-chain or branched C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy and
- m and n, independently of one another, represent integers from 0 to 4, characterized in that
- a) a bisphenol of the formula ##STR30## in which R.sub.1, R.sub.2, m, n and X have the meaning mentioned, is reacted with the sulphonic acid derivative of the formula
- R.sub.3 --SO.sub.2 --R.sub.4,
- in which
- R.sub.3 represents straight-chain or branched C.sub.1 -C.sub.12 -alkyl, C.sub.3 -C.sub.8 -cycloalkyl, C.sub.6 -C.sub.12 -aryl or C.sub.7 -C.sub.10 -aralkyl and
- R.sub.4 is OH, Cl, Br or O-O.sub.2 S-R.sub.3,
- to give a bissulphonate of the formula ##STR31## in which R.sub.1, R.sub.2, R.sub.3, m, n and X have the meaning mentioned, and
- b) the bissulphonate obtained is hydrogenated in dissolved form at an H.sub.2 pressure of 1 to 100 bar on a support-containing or support-free hydrogenation catalyst in an amount of from 0.5 to 10 g of hydrogenation-active component per mole of bissulphonate.
An aromatic hydrocarbon of the formula ##STR32## in which X denotes or ##STR33## R.sub.1 and R.sub.2, independently of one another, denote straight-chain or branched C.sub.1 -C.sub.4 -alkyl and
- q and r, independently of one another, represent integers from 0 to 4.
The aromatic hydrocarbon 1,1-diphenyl-3,5,5-trimethylcyclohexane.
Dependencies are inferred from the claim text.