Described herein are compositions composed of frustrated Lewis pairs impregnated in porous materials such as, for example, metal-organic frameworks, and their uses thereof. These compositions may allow new applications of frustrated Lewis pairs in catalysis by sequestering and protecting the frustrated Lewis pair within the nanospace of the porous material. Also provided are methods of hydrogenating an organic compound having at least one unsaturated functional group comprising using the compositions described herein.

A neutral or cationic mononuclear ruthenium divalent complex represented by formula (1) can actualize exceptional catalytic activity in at least one reaction among a hydrosilylation reaction, hydrogenation reaction, and carbonyl compound reduction reaction. ##STR00001##
(In the formula, R.sup.1-R.sup.6 each independently represent a hydrogen atom or an alkyl group, aryl group, aralkyl group, organooxy group, monoorganoamino group, diorganoamino group, monoorganophosphino group, diorganophosphino group, monoorganosilyl group, diorganosilyl group, triorganosilyl group, or organothio group optionally substituted by X; at least one pair comprising any of R.sup.1-R.sup.3 and any of R.sup.4-R.sup.6 together represents a crosslinkable substituent; X represents a halogen atom, organooxy group, monoorganoamino group, diorganoamino group, or organothio group; L each independently represent a two-electron ligand other than CO and thiourea ligands; two L may bond to each other; and m represents an integer of 3 or 4.)

A neutral or cationic mononuclear ruthenium divalent complex represented by formula (1) can actualize exceptional catalytic activity in at least one reaction among a hydrosilylation reaction, hydrogenation reaction, and carbonyl compound reduction reaction. ##STR00001##
(In the formula, R.sup.1-R.sup.6 each independently represent a hydrogen atom or an alkyl group, aryl group, aralkyl group, organooxy group, monoorganoamino group, diorganoamino group, monoorganophosphino group, diorganophosphino group, monoorganosilyl group, diorganosilyl group, triorganosilyl group, or organothio group optionally substituted by X; at least one pair comprising any of R.sup.1-R.sup.3 and any of R.sup.4-R.sup.6 together represents a crosslinkable substituent; X represents a halogen atom, organooxy group, monoorganoamino group, diorganoamino group, or organothio group; L each independently represent a two-electron ligand other than CO and thiourea ligands; two L may bond to each other; and m represents an integer of 3 or 4.)

The present invention relates to a method for regenerating a hydrogenation catalyst for a phthalate compound. More specifically, the present invention regenerates a hydrogenation catalyst for a phthalate compound by using an alcohol, and thereby provides a method for regenerating a hydrogenation catalyst for a phthalate compound that is capable of continuously hydrogenating a phthalate compound without replacing a catalyst in a catalytic reactor, and is also capable of improving operational stability and the lifetime of a catalyst and increasing economic efficiency.

The present invention relates to a method for regenerating a hydrogenation catalyst for a phthalate compound. More specifically, the present invention regenerates a hydrogenation catalyst for a phthalate compound by using an alcohol, and thereby provides a method for regenerating a hydrogenation catalyst for a phthalate compound that is capable of continuously hydrogenating a phthalate compound without replacing a catalyst in a catalytic reactor, and is also capable of improving operational stability and the lifetime of a catalyst and increasing economic efficiency.

A process for producing vinyl esters of carboxylic acids, especially vinyl esters of ketocarboxylic acids, which can be -ketocarboxylic acids or -ketocarboxylic acids. The vinyl esters of the carboxylic acids in their vinyl group can have hydrogen and have preferably deuterium in their vinyl group. The vinyl esters can be hydrogenated with para-hydrogen and the spin of the para-hydrogen can be transferred to the carbonyl carbon atom of the carboxyl group, which carbonyl-carbon atom is a .sup.13C, followed by hydrolysis of the ester group, producing carboxylic acids, especially ketocarboxylic acids having a hyperpolarized .sup.13C in the carbonyl carbon atom of the carboxyl group.

A process for producing vinyl esters of carboxylic acids, especially vinyl esters of ketocarboxylic acids, which can be -ketocarboxylic acids or -ketocarboxylic acids. The vinyl esters of the carboxylic acids in their vinyl group can have hydrogen and have preferably deuterium in their vinyl group. The vinyl esters can be hydrogenated with para-hydrogen and the spin of the para-hydrogen can be transferred to the carbonyl carbon atom of the carboxyl group, which carbonyl-carbon atom is a .sup.13C, followed by hydrolysis of the ester group, producing carboxylic acids, especially ketocarboxylic acids having a hyperpolarized .sup.13C in the carbonyl carbon atom of the carboxyl group.

This invention describes processes to make products by cross metathesis of functionalized or non-functionalized olefins with poly-branched poly-olefins such as terpenes (e.g., farnesene(s), -farnesene, -farnesene, -myrcene, etc.) and compositions made by such methods. More particularly, the present invention relates to methods of making (i) cross metathesis products by a cross metathesis reaction between at least one hydrovinylated olefinic substrate and at least one hydrovinylated cross metathesis substrate in the presence of at least one olefin metathesis catalyst; (ii) cross metathesis products by a cross metathesis reaction between at least one hydrovinylated olefinic substrate and at least one cross metathesis substrate in the presence of at least one olefin metathesis catalyst; and (iii) cross metathesis products by a cross metathesis reaction between at least one olefinic substrate and at least one hydrovinylated cross metathesis substrate in the presence of at least one olefin metathesis catalyst; as well as compositions made by such methods.

This invention describes processes to make products by cross metathesis of functionalized or non-functionalized olefins with poly-branched poly-olefins such as terpenes (e.g., farnesene(s), -farnesene, -farnesene, -myrcene, etc.) and compositions made by such methods. More particularly, the present invention relates to methods of making (i) cross metathesis products by a cross metathesis reaction between at least one hydrovinylated olefinic substrate and at least one hydrovinylated cross metathesis substrate in the presence of at least one olefin metathesis catalyst; (ii) cross metathesis products by a cross metathesis reaction between at least one hydrovinylated olefinic substrate and at least one cross metathesis substrate in the presence of at least one olefin metathesis catalyst; and (iii) cross metathesis products by a cross metathesis reaction between at least one olefinic substrate and at least one hydrovinylated cross metathesis substrate in the presence of at least one olefin metathesis catalyst; as well as compositions made by such methods.

An object of the present invention is to provide a method for hydrogenating a biodiesel fuel for producing a biodiesel fuel having an excellent oxidation stability and cold flow property. The present invention serves to produce a biodiesel fuel excellent in oxidation stability, by hydrogenating a biodiesel fuel with oxygen present in the reaction system in the presence of a catalyst containing at least one type of noble metal selected from metals of Groups 8 to 10 in the periodic table.