The present invention relates to a transition metal complex having a PNNP4 ligand, which is easy to manufacture and handle and is relatively inexpensively available, and a method for manufacturing the same, as well as a method using this transition metal complex as a catalyst for hydrogenation reduction of ketones, esters and amides to manufacture corresponding alcohols, aldehydes, hemiacetals and hemiaminals, a method using this transition metal complex as a catalyst for oxidation of alcohols, hemiacetals and hemiaminals to manufacture corresponding carbonyl compounds, and a method using this transition metal complex as a catalyst for dehydrogenation condensation between alcohols and amines to manufacture alkylamines.

The present invention relates to a transition metal complex having a PNNP4 ligand, which is easy to manufacture and handle and is relatively inexpensively available, and a method for manufacturing the same, as well as a method using this transition metal complex as a catalyst for hydrogenation reduction of ketones, esters and amides to manufacture corresponding alcohols, aldehydes, hemiacetals and hemiaminals, a method using this transition metal complex as a catalyst for oxidation of alcohols, hemiacetals and hemiaminals to manufacture corresponding carbonyl compounds, and a method using this transition metal complex as a catalyst for dehydrogenation condensation between alcohols and amines to manufacture alkylamines.

The present invention provides a process for preparing 2-(1,5,5-trimethyl-2-cyclopentenyl)ethyl acetate of the following formula (3), wherein Ac represents an acetyl group, the process comprising: subjecting a haloacetaldehyde alkyl 3,4,4-trimethyl-2-cyclopentenyl acetal compound of the following general formula (1), wherein R represents a linear or branched alkyl group having 1 to 4 carbon atoms, and Y represents a halogen atom, to a dehydrohalogenation reaction in the presence of a base, followed by a rearrangement reaction to obtain a (1,5,5-trimethyl-2-cyclopentenyl)acetate compound of the following general formula (2), wherein R is as defined above, and subjecting the alkoxycarbonylmethyl group (i.e., —CH.sub.2C(═O)OR) of the (1,5,5-trimethyl-2-cyclopentenyl)acetate compound (2) to a multi-step conversion to be converted into a 2-acetoxyethyl group (i.e., —CH.sub.2CH.sub.2OAc) to obtain 2-(1,5,5-trimethyl-2-cyclopentenyl)ethyl acetate (3).

##STR00001##

The present invention provides a process for preparing 2-(1,5,5-trimethyl-2-cyclopentenyl)ethyl acetate of the following formula (3), wherein Ac represents an acetyl group, the process comprising: subjecting a haloacetaldehyde alkyl 3,4,4-trimethyl-2-cyclopentenyl acetal compound of the following general formula (1), wherein R represents a linear or branched alkyl group having 1 to 4 carbon atoms, and Y represents a halogen atom, to a dehydrohalogenation reaction in the presence of a base, followed by a rearrangement reaction to obtain a (1,5,5-trimethyl-2-cyclopentenyl)acetate compound of the following general formula (2), wherein R is as defined above, and subjecting the alkoxycarbonylmethyl group (i.e., —CH.sub.2C(═O)OR) of the (1,5,5-trimethyl-2-cyclopentenyl)acetate compound (2) to a multi-step conversion to be converted into a 2-acetoxyethyl group (i.e., —CH.sub.2CH.sub.2OAc) to obtain 2-(1,5,5-trimethyl-2-cyclopentenyl)ethyl acetate (3).

##STR00001##

The present invention provides a process for preparing a (1,2-dimethyl-3-methylenecyclopentyl)acetate compound of the following general formula (3), wherein R represents a linear or branched alkyl group having 1 to 4 carbon atoms, the process comprising subjecting a haloacetaldehyde alkyl 2,3-dimethyl-2-cyclopentenyl acetal compound of the following general formula (1), wherein R is as defined above, and Y represents a halogen atom, to a dehydrohalogenation reaction in the presence of a base, followed by a rearrangement reaction to obtain a (1,2-dimethyl-2-cyclopentenyl)acetate compound of the following general formula (2), wherein R is as defined above, and subjecting the (1,2-dimethyl-2-cyclopentenyl)acetate compound (2) to an epoxidation reaction, followed by an isomerization reaction and then a methylenation reaction to obtain the (1,2-dimethyl-3-methylenecyclopentyl)acetate compound of the following general formula (3). The present invention also provides a process for preparing (1,2-dimethyl-3-methylenecyclopentyl)acetaldehyde of the following formula (4), the process comprising the aforesaid process for preparing the (1,2-dimethyl-3-methylenecyclopentyl)acetate compound (3), and converting an alkoxycarbonylmethyl group (i.e., —CH.sub.2C(═O)OR) of the (1,2-dimethyl-3-methylenecyclopentyl)acetate compound (3) to a formylmethyl group (i.e., —CH.sub.2CHO) to obtain (1,2-dimethyl-3-methylenecyclopentyl)acetaldehyde (4).

##STR00001##

The present invention provides a process for preparing a (1,2-dimethyl-3-methylenecyclopentyl)acetate compound of the following general formula (3), wherein R represents a linear or branched alkyl group having 1 to 4 carbon atoms, the process comprising subjecting a haloacetaldehyde alkyl 2,3-dimethyl-2-cyclopentenyl acetal compound of the following general formula (1), wherein R is as defined above, and Y represents a halogen atom, to a dehydrohalogenation reaction in the presence of a base, followed by a rearrangement reaction to obtain a (1,2-dimethyl-2-cyclopentenyl)acetate compound of the following general formula (2), wherein R is as defined above, and subjecting the (1,2-dimethyl-2-cyclopentenyl)acetate compound (2) to an epoxidation reaction, followed by an isomerization reaction and then a methylenation reaction to obtain the (1,2-dimethyl-3-methylenecyclopentyl)acetate compound of the following general formula (3). The present invention also provides a process for preparing (1,2-dimethyl-3-methylenecyclopentyl)acetaldehyde of the following formula (4), the process comprising the aforesaid process for preparing the (1,2-dimethyl-3-methylenecyclopentyl)acetate compound (3), and converting an alkoxycarbonylmethyl group (i.e., —CH.sub.2C(═O)OR) of the (1,2-dimethyl-3-methylenecyclopentyl)acetate compound (3) to a formylmethyl group (i.e., —CH.sub.2CHO) to obtain (1,2-dimethyl-3-methylenecyclopentyl)acetaldehyde (4).

##STR00001##

The present invention relates to a process for preparing a process for preparing a (2-cyclopentenyl)acetate ester compound of the following general formula (2): wherein R represents a linear or branched alkyl group having 1 to 4 carbon atoms, Y represents a halogen atom, and X.sub.1 to X.sub.7 represent, independently of each other, a hydrogen atom or a methyl group, with the proviso that one to three among X.sub.1 to X.sub.7 represent a methyl group and the remaining represent a hydrogen atom, the process comprising: subjecting a haloacetaldehyde alkyl 2-cyclopentenyl acetal compound of the following general formula (1): wherein R is as defined above, X.sub.1 to X.sub.7 are as selected in the general formula (2), respectively, and Y represents a halogen atom, to a dehydrohalogenation reaction in the presence of a base, followed by a rearrangement reaction to form the (2-cyclopentenyl)acetate ester compound (2) and a process for preparing a (2-cyclopentenyl)acetic acid compound of the following general formula (3): wherein X.sub.1 to X.sub.7 are as selected in the general formula (1), respectively, the process comprising hydrolyzing the (2-cyclopentenyl)acetate ester compound (2) to form the (2-cyclopentenyl)acetic acid compound (3). The present invention relates also to the novel compound, haloacetaldehyde alkyl 2-cyclopentenyl acetal compound (1).

##STR00001##

The present invention relates to a process for preparing a process for preparing a (2-cyclopentenyl)acetate ester compound of the following general formula (2): wherein R represents a linear or branched alkyl group having 1 to 4 carbon atoms, Y represents a halogen atom, and X.sub.1 to X.sub.7 represent, independently of each other, a hydrogen atom or a methyl group, with the proviso that one to three among X.sub.1 to X.sub.7 represent a methyl group and the remaining represent a hydrogen atom, the process comprising: subjecting a haloacetaldehyde alkyl 2-cyclopentenyl acetal compound of the following general formula (1): wherein R is as defined above, X.sub.1 to X.sub.7 are as selected in the general formula (2), respectively, and Y represents a halogen atom, to a dehydrohalogenation reaction in the presence of a base, followed by a rearrangement reaction to form the (2-cyclopentenyl)acetate ester compound (2) and a process for preparing a (2-cyclopentenyl)acetic acid compound of the following general formula (3): wherein X.sub.1 to X.sub.7 are as selected in the general formula (1), respectively, the process comprising hydrolyzing the (2-cyclopentenyl)acetate ester compound (2) to form the (2-cyclopentenyl)acetic acid compound (3). The present invention relates also to the novel compound, haloacetaldehyde alkyl 2-cyclopentenyl acetal compound (1).

##STR00001##

The invention provides (meth)acrylic oligomers prepared from C1-C20 alkyl and C5-C20 cycloalkyl (meth)acrylates, wherein said oligomers have a Mn of about 300 g/mole to about 3,000 g/mole; a Mw of about 700 g/mole to about 6,000 g/mole; a Mz of about 900 g/mole to about 10,000 g/mole. The oligomers may have a Yellowness Index, according to ASTM E313 of less than 2. The oligomers of the invention are useful as tackifiers in adhesive compositions, but also are believed to be useful also in general polymer modification as plasticizers, leveling agents, viscosity reducers (i.e., rheology modifiers), and for increasing solids content in solvent-borne applications of all types with little detrimental impact on viscosity. The invention also provides adhesive compositions and laminate articles coated on at least one side with the adhesive compositions of the invention.

The invention provides (meth)acrylic oligomers prepared from C1-C20 alkyl and C5-C20 cycloalkyl (meth)acrylates, wherein said oligomers have a Mn of about 300 g/mole to about 3,000 g/mole; a Mw of about 700 g/mole to about 6,000 g/mole; a Mz of about 900 g/mole to about 10,000 g/mole. The oligomers may have a Yellowness Index, according to ASTM E313 of less than 2. The oligomers of the invention are useful as tackifiers in adhesive compositions, but also are believed to be useful also in general polymer modification as plasticizers, leveling agents, viscosity reducers (i.e., rheology modifiers), and for increasing solids content in solvent-borne applications of all types with little detrimental impact on viscosity. The invention also provides adhesive compositions and laminate articles coated on at least one side with the adhesive compositions of the invention.