The present invention encompasses a catalyst composition that includes a heterogeneous oligomerization catalyst including a metal-organic framework, the metal-organic framework including a plurality of first metal ions coordinated to one or more ligands, wherein each of the one or more ligands has only one N-heterocyclic aromatic group. The present invention further includes a method of oligomerization that comprises contacting one or more olefins with the heterogeneous oligomerization catalyst to form one or more oligomers, wherein the heterogeneous catalyst comprises the said metal-organic framework and an optional support.

This invention relates generally to olefin metathesis catalysts, to the preparation of such compounds, compositions comprising such compounds, methods of using such compounds, and the use of such compounds in the metathesis of olefins and in the synthesis of related olefin metathesis catalysts. The invention has utility in the fields of catalysis, organic synthesis, polymer chemistry, and in industrial applications such as oil and gas, fine chemicals and pharmaceuticals.

Disclosed is catalyst composition, a process for preparing the catalyst composition, and a use of the catalyst composition. The catalyst composition comprises 1 wt % to 4 wt % of free azacarbene, 1 wt % to 2 wt % of azacarbene iron, 15 wt % to 30 wt % of a phase transfer catalyst, 1 wt % to 5 wt % of a hydrogen donor, 5 wt % to 10 wt % of phosphoric acid, 0.5 wt % to 1 wt % of emulsifier, with the rest being solvent. This disclosure also provides a process for preparing the catalyst composition, comprising: mixing the free azacarbene and the azacarbene iron with the solvent according to a ratio, then adding and mixing the phase transfer catalyst and the hydrogen donor, then adding and mixing the phosphoric acid and the emulsifier to obtain the catalyst composition. The beneficial effect of this disclosure is: only less azacarbene iron and free azacarbene are needed to achieve rapid and efficient viscosity reduction of heavy oil.

Provided herein are methods of producing polymers from furan and optionally diol compounds, using an organocatalyst. A polymer composition comprising a polymer prepared by the method is contemplated. Provided herein are also polymer compositions, such as poly(alkylene-2,5-furandicarboxylate). In some embodiments, polymer compositions have any one of the characteristics discussed herein, or any combinations thereof.

Described are methods for preparing a deuterated aldehyde using N-heterocyclic carbene catalysts in a solvent comprising D.sub.2O. The methods may be used to convert a wide variety of aldehydes (e.g., aryl, alkyl, or alkenyl aldehydes) to C-1 deuterated aldehydes under mild reaction conditions without functionality manipulation.

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.

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.

Disclosed herein are methods for synthesizing fatty olefin metathesis products of high Z-isomeric purity from olefin feedstocks of low Z-isomeric purity. The methods include contacting a contacting an olefin metathesis reaction partner, such as acylated alkenol or an alkenal acetal, with an internal olefin in the presence of a Z-selective metathesis catalyst to form the fatty olefin metathesis product. In various embodiments, the fatty olefin metathesis products are insect pheromones. Pheromone compositions and methods of using them are also described.

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.

Compound of formula 4 or formula 5 ##STR00001##
wherein
L is a neutral ligand, preferably a nitrogen-containing heterocyclic carbene (NHC) such as carbene containing at least two nitrogen atoms, a cyclic aminoalkyl carbene (CAAC) or a bicyclic aminoalkyl carbene (BICAAC);
R.sup.1, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9, R.sup.10 and R.sup.11 are, independently, H, unbranched or branched C.sub.1-20 alkyl, C.sub.5-9 cycloalkyl, unbranched or branched C.sub.1-20 alkoxy, optionally bearing one or more halogen atoms, respectively; or aryl, optionally substituted with one or more of unbranched or branched C.sub.1-20 alkyl, C.sub.5-9 cycloalkyl, unbranched or branched C.sub.1-20 alkoxy, aryl, aryloxy, unbranched or branched C.sub.1-20 alkylcarbonyl, arylcarbonyl, unbranched or branched C.sub.1-20 alkoxycarbonyl, aryloxycarbonyl, heteroaryl, carboxyl, cyano, nitro, amido, aminosulfonyl, N-heteroarylsulfonyl, unbranched or branched C.sub.1-20 alkylsulfonyl, arylsulfonyl, unbranched or branched C.sub.1-20 alkylsulfinyl, arylsulfinyl, unbranched or branched C.sub.1-20 alkylthio, arylthio, sulfonamide, halogen or N(R.sup.y)(R.sup.z), wherein R.sup.y and R.sup.z are independently selected from H and C.sub.1-20 alkyl:
R.sup.2 is H, unbranched or branched C.sub.1-20 alkyl.