The present disclosure relates to a catalyst system comprising i) (a) an N.sup.2-phosphinyl bicyclic amidine chromium salt or (b) a chromium salt and an N.sup.2-phosphinyl bicyclic amidine and ii) an organoaluminum compound. The present disclosure also relate to a process comprising: a) contacting i) ethylene; ii) a catalyst system comprising (a) an N.sup.2-phosphinyl bicyclic amidine chromium salt complex or (b) a chromium salt and an N.sup.2-phosphinyl bicyclic amidine; ii) an organoaluminum compound, and iii) optionally an organic reaction medium; and b) forming an oligomer product in a reaction zone.

The present disclosure relates to a catalyst system comprising i) (a) a bicyclic 2-[(phosphinyl)aminyl] cyclic imine chromium salt or (b) a chromium salt and a bicyclic 2-[(phosphinyl)aminyl] cyclic imine and ii) an organoaluminum compound. The present disclosure also relates to a process comprising: a) contacting i) ethylene; ii) a catalyst system comprising (a) a 2-[(phosphinyl)aminyl] cyclic imine chromium salt complex or (b) a chromium salt and a bicyclic 2-[(phosphinyl)aminyl] cyclic imine; ii) an organoaluminum compound, and iii) optionally an organic reaction medium; and b) forming an oligomer product in a reaction zone.

The present invention describes a method which outlines a process for conversion of CBD to a Δ.sup.9-tetrahydrocannabinol (Δ.sup.9-THC) compound or derivative thereof involving treating a naturally produced CBD intermediate compound with an organoaluminum-based Lewis acid catalyst, under conditions effective to produce the Δ.sup.9-tetrahydrocannabinol compound or derivative thereof at a relatively high concentration. The source of the CBD is from industrial hemp having less than 0.3% Δ.sup.9-THC and extracting and purifying a CBD distillate or isolate or a combination thereof. This procedure will produce Δ.sup.9-THC that is essentially free from any other cannabinoids other than some trace amounts of the initial CBD starting material, or about 95% Δ.sup.9-THC and 2-4% CBD. Another aspect of the present invention relates to a process for further purification and enrichment of the Δ.sup.9-THC using distillation and collecting an essentially pure fraction of Δ.sup.9-THC using additional distillation or enrichment form of purification. Included are methods and processes to scale the reaction from the lab to large scale manufacturing. Included are methods for adding a molecule marker to authenticate high purity Δ.sup.9-THC products. Formulations and uses for pharmaceuticals, nutraceuticals, food products, and topicals are also provided.

The invention relates to a process for preparing a carboxylic ester by reacting an aldehyde in the presence of an aluminum alkoxide, wherein the aluminum alkoxide is obtained either by reacting an aluminum hydride with an aldehyde or by reacting a different aluminum alkoxide with a carboxylic ester.

Catalyst systems for tetramerizing ethylene to form 1-octene may include a catalyst which may include a chromium compound coordinated with a ligand and a co-catalyst which may include an organoaluminum compound. The ligand may have a chemical structure according to Chemical Structure (I), wherein R.sub.5 is a (C.sub.1-C.sub.15) alkyl group, a (C.sub.3-C.sub.15) cyclohydrocarbyl group, a (C.sub.3-C.sub.15) cycloheterohydrocarbyl group, or a (C.sub.1-C.sub.15) aryl group, and R.sub.A, R.sub.B, R.sub.C, R.sub.D, R.sub.E, R.sub.F, R.sub.G, R.sub.H, R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.6, R.sub.7, R.sub.8, and R.sub.9 are independently chosen from a hydrogen atom, a (C.sub.1-C.sub.50) hydrocarbyl group, or a (C.sub.1-C.sub.50) heterohydrocarbyl group.

The present disclosure relates to a ligand compound, a catalyst system for oligomerization, and a method for olefin oligomerization using the same. The catalyst system for oligomerization using the ligand compound according to the present disclosure has excellent catalytic activity, exhibits high selectivity to 1-hexene and 1-octene, and greatly reduces the production of the by-products, thereby enabling efficient preparation of alpha-olefin.

The present disclosure relates to a catalyst system comprising i) (a) an N.sup.2-phosphinyl bicyclic amidine chromium salt or (b) a chromium salt and an N.sup.2-phosphinyl bicyclic amidine and ii) an organoaluminum compound. The present disclosure also relate to a process comprising: a) contacting i) ethylene; ii) a catalyst system comprising (a) an N.sup.2-phosphinyl bicyclic amidine chromium salt complex or (b) a chromium salt and an N.sup.2-phosphinyl bicyclic amidine; ii) an organoaluminum compound, and iii) optionally an organic reaction medium; and b) forming an oligomer product in a reaction zone.

Methods of preparing oligomers of an olefin are provided. The methods can include providing a composition that includes an alkylaluminum compound, a chromium compound, and a hydrocarbon solvent. The hydrocarbon solvent can include n-undecane, a C8-C11 alkane compound having one branch, or a mixture thereof. The methods can further include contacting an olefin with the composition to form oligomers of the olefin. The olefin can include ethylene, and the oligomers of the olefin can include 1-hexene.

A method of precipitating polymer and deactivated organometallic catalyst in an olefin oligomerization reaction is provided. The method includes providing an effluent stream from an olefin oligomerization reaction. The effluent stream can include a polymer and an organometallic catalyst. The method can further include introducing sorbent particles into the effluent stream. The sorbent particles can include a deactivating agent. The deactivating agent can be water, an alcohol, an amine, an amino alcohol, or a combination thereof. At least about 10% of the sorbent particles can have a particle size in a range from 10 μm and 60 μm. The method can further include cooling the effluent stream, thereby precipitating polymer and deactivated organometallic catalyst from the effluent stream to provide a precipitate that includes sorbent, polymer, and deactivated catalyst.

Catalyst compositions and processes for the oligomerization of ethylene to 1-octene are described. The catalyst composition includes a triamino bisphospino (NPNPN) ligand system with specific phosphorous and nitrogen ligands. The terminal nitrogen atoms include linear alkyl hydrocarbons that differ in the number of carbon atoms by 3.