Method of making a cross metathesis product, the method comprising at least step (X) or step (Y): (X) reacting in a cross metathesis reaction a first compound comprising a terminal olefinic group with a second compound comprising a terminal olefinic group, wherein the first and the second compound may be identical or may be different from one another; or (Y) reacting in a ring-closing metathesis reaction two terminal olefinic groups which are comprised in a third compound; wherein the reacting in step (X) or step (Y) is performed in the presence of a ruthenium carbene complex comprising a [Ru═C]-moiety and an internal olefin.

The present invention relates to the field of organic synthesis and more specifically it concerns a process for preparing compound of formula (I) by a cross metathesis reaction. Said compound of formula (I) is valuable new chemical intermediate for producing perfuming ingredients and is also part of the present invention.

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.

The present disclosure provides a method that embodies a simple and effective route to remove homogeneous catalysts from solutions wherein NMR/MRI signal amplification by reversible exchange (SABRE) or parahydrogen-induced polarization (PHIP) is performed. A method for recovering a homogeneous SABRE/PHIP catalyst for reuse is also described.

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.

The present disclosure relates to a hydrogen gas production method including: a first step of generating a mixed gas containing hydrogen and carbon dioxide from a hydrogen storage agent by dehydrogenation reaction using a catalyst in a reactor; a second step of purifying the generated mixed gas to acquire a gas having a high hydrogen concentration; a third step of separating a solution in the reactor into a solution enriched with the catalyst and a permeate using a separation membrane unit; and a fourth step of supplying the solution enriched with the catalyst to the reactor for reusing in the first step.

Catalyst systems and methods for making and using the same are disclosed. A catalyst composition is provided that includes a catalyst compound supported to form a supported catalyst system, the catalyst compound including: ##STR00001##
where each of R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7 and X are as discussed herein.

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.

Described herein is an iron(II)-phthalocyanine catalyzed C—H bond amination of alkyl azides. The catalyst is effective to produce intramolecular amination of saturated C—H bonds in moderate to excellent yields and the methods are tolerant of a wide scope of substrates. The methods described are useful for the synthesis of natural products derivatives and for the late-stage functionalization of pharmaceuticals.