The present invention provides a carboxylic acid ester compound represented by formula (1) that is useful as a fragrance component or as a formulated fragrance material,

##STR00001##

wherein R.sup.1 is —COOR, wherein R is an alkyl group having 1 to 4 carbon atoms.

The present invention provides a carboxylic acid ester compound represented by formula (1) that is useful as a fragrance component or as a formulated fragrance material,

##STR00001##

wherein R.sup.1 is —COOR, wherein R is an alkyl group having 1 to 4 carbon atoms.

The present invention provides a method for producing a bifunctional compound having a norbornane skeleton, the method comprising a step of hydroformylating a compound having an olefin with carbon monoxide and hydrogen, wherein the molar ratio of the carbon monoxide to the hydrogen during the reaction is 55/45 or more and 95/5 or less in the hydroformylating step.

The present invention provides a method for producing a bifunctional compound having a norbornane skeleton, the method comprising a step of hydroformylating a compound having an olefin with carbon monoxide and hydrogen, wherein the molar ratio of the carbon monoxide to the hydrogen during the reaction is 55/45 or more and 95/5 or less in the hydroformylating step.

Process for the alkoxycarbonylation of trivinylcyclohexane.

The invention relates to triesters of cyclohexanetripropionic acid, preparation thereof and use thereof as plasticizers for polymers.

The invention relates to triesters of cyclohexanetripropionic acid, preparation thereof and use thereof as plasticizers for polymers.

The invention relates to a process comprising the following process steps: a) introducing a first alcohol, the first alcohol having 2 to 30 carbon atoms; b) adding a phosphine ligand and a compound which comprises Pd, or adding a complex comprising Pd and a phosphine ligand; c) adding a second alcohol; d) supplying CO; e) heating the reaction mixture, the first alcohol reacting with CO and the second alcohol to form an ester;
where the phosphine ligand is a compound of formula (I) ##STR00001##
where m and n are each independently 0 or 1; R.sup.1, R.sup.2, R.sup.3, R.sup.4 are each independently selected from —(C.sub.1-C.sub.12)-alkyl, —(C.sub.3-C.sub.12)-cycloalkyl, —(C.sub.3-C.sub.12)-heterocycloalkyl, —(C.sub.6-C.sub.20)-aryl, —(C.sub.3-C.sub.20)-heteroaryl; at least one of the R.sup.1, R.sup.2, R.sup.3, R.sup.4 radicals is a —(C.sub.3-C.sub.20)-heteroaryl radical; and R.sup.1, R.sup.2, R.sup.3, R.sup.4, if they are —(C.sub.1-C.sub.12)-alkyl, —(C.sub.3-C.sub.12)-cycloalkyl, —(C.sub.3-C.sub.12)-heterocycloalkyl, —(C.sub.6-C.sub.20)-aryl or —(C.sub.3-C.sub.20)-heteroaryl, may each independently be substituted by one or more substituents selected from —(C.sub.1-C.sub.12)-alkyl, —(C.sub.3-C.sub.12)-cycloalkyl, —(C.sub.3-C.sub.12)-heterocycloalkyl, —O—(C.sub.1-C.sub.12)-alkyl, —O—(C.sub.1-C.sub.12)-alkyl-(C.sub.6-C.sub.20)-aryl, —O—(C.sub.3-C.sub.12)-cycloalkyl, —S—(C.sub.1-C.sub.12)-alkyl, —S—(C.sub.3-C.sub.12)-cycloalkyl, —COO—(C.sub.1-C.sub.12)-alkyl, —COO—(C.sub.3-C.sub.12)-cycloalkyl, —CONH—(C.sub.1-C.sub.12)-alkyl, —CONH—(C.sub.3-C.sub.12)-cycloalkyl, —CO—(C.sub.1-C.sub.12)-alkyl, —CO—(C.sub.3-C.sub.12)-cycloalkyl, —N—[(C.sub.1-C.sub.12)-alkyl].sub.2, —(C.sub.6-C.sub.20)-aryl, —(C.sub.6-C.sub.20)-aryl-(C.sub.1-C.sub.12)-alkyl, —(C.sub.6-C.sub.20)-aryl-O—(C.sub.1-C.sub.12)-alkyl, —(C.sub.3-C.sub.20)-heteroaryl, —(C.sub.3-C.sub.20)-heteroaryl-(C.sub.1-C.sub.12)-alkyl, —(C.sub.3-C.sub.20)-heteroaryl-O—(C.sub.1-C.sub.12)-alkyl, —COOH, —OH, —SO.sub.3H, —NH.sub.2, halogen.

The invention relates to a process comprising the following process steps: a) introducing a first alcohol, the first alcohol having 2 to 30 carbon atoms; b) adding a phosphine ligand and a compound which comprises Pd, or adding a complex comprising Pd and a phosphine ligand; c) adding a second alcohol; d) supplying CO; e) heating the reaction mixture, the first alcohol reacting with CO and the second alcohol to form an ester;
where the phosphine ligand is a compound of formula (I) ##STR00001##
where m and n are each independently 0 or 1; R.sup.1, R.sup.2, R.sup.3, R.sup.4 are each independently selected from —(C.sub.1-C.sub.12)-alkyl, —(C.sub.3-C.sub.12)-cycloalkyl, —(C.sub.3-C.sub.12)-heterocycloalkyl, —(C.sub.6-C.sub.20)-aryl, —(C.sub.3-C.sub.20)-heteroaryl; at least one of the R.sup.1, R.sup.2, R.sup.3, R.sup.4 radicals is a —(C.sub.3-C.sub.20)-heteroaryl radical; and R.sup.1, R.sup.2, R.sup.3, R.sup.4, if they are —(C.sub.1-C.sub.12)-alkyl, —(C.sub.3-C.sub.12)-cycloalkyl, —(C.sub.3-C.sub.12)-heterocycloalkyl, —(C.sub.6-C.sub.20)-aryl or —(C.sub.3-C.sub.20)-heteroaryl, may each independently be substituted by one or more substituents selected from —(C.sub.1-C.sub.12)-alkyl, —(C.sub.3-C.sub.12)-cycloalkyl, —(C.sub.3-C.sub.12)-heterocycloalkyl, —O—(C.sub.1-C.sub.12)-alkyl, —O—(C.sub.1-C.sub.12)-alkyl-(C.sub.6-C.sub.20)-aryl, —O—(C.sub.3-C.sub.12)-cycloalkyl, —S—(C.sub.1-C.sub.12)-alkyl, —S—(C.sub.3-C.sub.12)-cycloalkyl, —COO—(C.sub.1-C.sub.12)-alkyl, —COO—(C.sub.3-C.sub.12)-cycloalkyl, —CONH—(C.sub.1-C.sub.12)-alkyl, —CONH—(C.sub.3-C.sub.12)-cycloalkyl, —CO—(C.sub.1-C.sub.12)-alkyl, —CO—(C.sub.3-C.sub.12)-cycloalkyl, —N—[(C.sub.1-C.sub.12)-alkyl].sub.2, —(C.sub.6-C.sub.20)-aryl, —(C.sub.6-C.sub.20)-aryl-(C.sub.1-C.sub.12)-alkyl, —(C.sub.6-C.sub.20)-aryl-O—(C.sub.1-C.sub.12)-alkyl, —(C.sub.3-C.sub.20)-heteroaryl, —(C.sub.3-C.sub.20)-heteroaryl-(C.sub.1-C.sub.12)-alkyl, —(C.sub.3-C.sub.20)-heteroaryl-O—(C.sub.1-C.sub.12)-alkyl, —COOH, —OH, —SO.sub.3H, —NH.sub.2, halogen.

The invention relates to a process for preparing carboxylic acids or salts thereof by hydrolysis or saponification of an ester, which is obtained by alkoxycarbonylation of a C2 to C20 hydrocarbon having at least one multiple bond, preferably having at least one olefinic double bond, in which the homogeneous catalyst system used is separated from the product mixture by means of membrane separation. In a development of the present invention, the ester thus formed is converted into another ester by transesterification and then hydrolyzed or saponified.