In one aspect, phosphine compounds comprising three adamantyl moieties (PAd.sub.3) and associated synthetic routes are described herein. Each adamantyl moiety may be the same or different. For example, each adamantyl moiety (Ad) attached to the phosphorus atom can be independently selected from the group consisting of adamantane, diamantane, triamantane and derivatives thereof. Transition metal complexes comprising PAd.sub.3 ligands are also provided for catalytic synthesis including catalytic cross-coupling reactions.

A process to produce 1-octene and 1-decene includes (a) separating a composition containing an oligomer product—which contains from 15 to 80 mol % C.sub.6 olefins, from 20 to 80 mol % C.sub.8 olefins, and from 5 to 20 mol % C.sub.10+ olefins—into a first oligomer composition containing C.sub.6 alkanes and at least 85 mol % C.sub.6 olefins (e.g., 1-hexene), a second oligomer composition containing at least 85 mol % C.sub.8 olefins (e.g., 1-octene), and a heavies stream containing C.sub.10+ olefins, then (b) contacting a metathesis catalyst system with the first oligomer composition to form a first composition comprising C.sub.10 linear internal olefins, (c) contacting the C.sub.10 linear internal olefins with an isomerization hydrofunctionalization catalyst system to form a second composition containing a functionalized alkane, (d) retro-hydrofunctionalizing the functionalized alkane to form a third composition containing 1-decene, and (e) purifying the third composition to isolate a fourth composition containing at least 90 mol % 1-decene. Processes to produce 1-hexene and 1-decene also are described, as well as related manufacturing systems.

Provided herein, in part, is a new class of sterically bulky, easily prepared N-heterocyclic carbene (NHC) ligands of Formula I, or a salt, solvate, geometric isomer, or stereoisomer thereof. The ligands are readily synthetically accessible exploiting the cost-effective, modular alkylation of anilines. The NHC ligands of the present disclosure can be used to prepare effective catalysts with transition metals, including the compound of Formula II, or a salt, solvate, geometric isomer, or stereoisomer thereof. In certain embodiments, the transition metal is Pd.

Provided is a method of generating hydrogen efficiently using a renewable resource as a raw material.

A method of producing hydrogen according to the present disclosure is a method in which hydrogen is generated from a saccharide in the presence of a solvent and the following catalyst: catalyst which contains at least one metal element selected from the metal elements in Groups 8, 9, and 10.

The catalyst is preferably a complex or salt of the metal element, and particularly preferably a complex including the at least one metal element selected from the metal elements in Groups 8, 9, and 10 and at least one ligand selected from pentamethylcyclopentadienyl, cyclopentadienyl, p-cymene, and 1,5-cyclooctadiene.

As the solvent, it is preferable to use at least one selected from an organic acid and an ionic liquid.

The saccharide may be a lignin-saccharide complex, and is preferably cellulose.

A process to produce 1-octene and 1-decene includes (a) separating a composition containing an oligomer product—which contains 15 to 80 mol % C.sub.6 olefins, 20 to 80 mol % C.sub.8 olefins, and 5 to 20 mol % C.sub.10+ olefins—into a first oligomer composition containing C.sub.6 alkanes and at least 85 mol % C.sub.6 olefins (e.g., 1-hexene), a second oligomer composition containing at least 20 mol % C.sub.8 olefins (e.g., 1-octene), and a heavies stream containing C.sub.10+ olefins, then (b) contacting a metathesis catalyst system with the first oligomer composition to form a first composition comprising C.sub.10 linear internal olefins, (c) contacting the C.sub.10 linear internal olefins with a catalytic isomerization catalyst system in the presence of photochemical irradiation to form a second composition comprising 1-decene, and (d) purifying the second composition to isolate a third composition comprising at least 90 mol % 1-decene. Processes to produce 1-hexene and 1-decene also are described, as well as related manufacturing systems and processes to produce higher carbon number normal alpha olefins from lower carbon number normal alpha olefins.

A process for the production of 4-hydroxybutyraldehyde is described. The process comprises reacting allyl alcohol with a mixture of carbon monoxide and hydrogen in the presence of methylcyclohexane as a reaction solvent and a catalyst system comprising a rhodium complex and a substituted or unsubstituted diphosphine ligand. The use of the methylcyclohexane increases the reaction rate while also giving a high yield of 4-hydroxybutyraldehyde compared to 3-hydroxy-2-methylpropionaldehyde and improving the separation of the hydroxyaldehyde products from the catalyst system.

Mixture of bisphosphites having an open and a closed outer unit and the use thereof as a catalyst mixture in hydroformylation.

Diphosphites having an open and a closed 2,4-methylated outer unit and use thereof in hydroformylation.

Described herein is a hydroformylation catalyst system and method useful for producing aldehydes from olefin substrates, without using carbon monoxide gas. The hydroformylation catalyst system includes a hydroformylation catalyst complex including a Group 9 metal complexed with a phosphine-based ligand; a syngas surrogate including formic acid and an anhydride compound, which forms carbon monoxide in situ; and hydrogen, which may derive from the syngas surrogate or not derived from the syngas surrogate. The method involves reacting the olefin substrate with a syngas surrogate in the presence of a hydroformylation catalyst complex, wherein the syngas surrogate forms carbon monoxide, and optionally hydrogen, in situ, and then isolating the aldehyde compound from a reaction mixture.

A process for the production of 4-hydroxybutyraldehyde is described. The process comprises reacting allyl alcohol with a mixture of carbon monoxide and hydrogen in the presence of methylcyclohexane as a reaction solvent and a catalyst system comprising a rhodium complex and a substituted or unsubstituted diphosphine ligand. The use of the methylcyclohexane increases the reaction rate while also giving a high yield of 4-hydroxybutyraldehyde compared to 3-hydroxy-2-methylpropionaldehyde and improving the separation of the hydroxyaldehyde products from the catalyst system.