Processes for converting an olefin reactant into a diol compound are disclosed, and these processes include the steps of contacting the olefin reactant and a supported chromium catalyst comprising chromium in a hexavalent oxidation state to reduce at least a portion of the supported chromium catalyst to form a reduced chromium catalyst, and hydrolyzing the reduced chromium catalyst to form a reaction product comprising the diol compound. While being contacted, the olefin reactant and the supported chromium catalyst can be irradiated with a light beam at a wavelength in the UV-visible spectrum. Optionally, these processes can further comprise a step of calcining at least a portion of the reduced chromium catalyst to regenerate the supported chromium catalyst.

The invention relates to a method for degradation of plastic materials into terephthalic acid (TPA) and/or ethylene glycol and/or other monomers that form the plastic materials.

The present disclosure provides a method of preparing a catalyst for synthesizing dimethyl ether or methylacetate from synthetic gas that includes preparing a nanosheet ferrierite zeolite (FER), and co-precipitating the nanosheet ferrierite zeolite and a precursor of a Cu—Zn—Al-based oxide (CZA) to obtain a hybrid CZA/FER catalyst.

The present disclosure provides a method of preparing a catalyst for synthesizing dimethyl ether or methylacetate from synthetic gas that includes preparing a nanosheet ferrierite zeolite (FER), and co-precipitating the nanosheet ferrierite zeolite and a precursor of a Cu—Zn—Al-based oxide (CZA) to obtain a hybrid CZA/FER catalyst.

A method for preparing the borate ester using a lithium compound includes: under the inert gas, stirring and mixing carboxylic acid and borane, and a catalyst lithium compound is added, then the borate ester is obtained with hydroboration; wherein the hydroboration is at room temperature for 10 to 80 min. After the hydroboration and is stopped by contacting air, the solvent is removed under reduced pressure, to obtain the borate esters with different substituents. The lithium compounds are n-butyl lithium, lithium aniline, p-methyl lithium aniline, o-methyl lithium aniline, 2-methoxyaniline lithium, 4-methoxyaniline lithium, 2,6-dimethylaniline lithium, and 2,6-diisopropylaniline lithium. The lithium compounds disclosed in the present invention can catalyze the boron hydrogenation reaction of carboxylic acid and borane with high activity under room temperature conditions; the amount of lithium compound is 0.1-0.9% of the molar amount of carboxylic acid.

Disclosed is a method for preparing a boric acid ester using non-catalyzed hydroboration of a carboxylic acid. The method includes: in an inert gas atmosphere, mixing pinacolborane and a carboxylic acid and stirring until uniform in a reaction flask subjected to dehydration and deoxygenation treatments, reacting for 6-12 hours to obtain the boric acid ester, then adding silica gel and methanol, and conducting a hydrolysis reaction to prepare an alcohol compound. The carboxylic acid is acetic acid, caproic acid, pentanoic acid, heptanoic acid, trimethylacetic acid, adipic acid, benzoic acid, 4-bromobenzoic acid, 4-fluorobenzoic acid, 1-naphthoic acid, 2-methoxybenzoic acid, 4-tert-butylbenzoic acid, 4-ethoxybenzoic acid, 2-bromobenzoic acid, 4-iodobenzoic acid, 3-phenylpropionic acid, diphenyl acetic acid, 2-phenylbutyric acid, indole-3-acetic acid, o-carboxyl phenylacetic acid or 2-methyl-5-bromobenzoic acid. The present invention utilizes a carboxylic acid to efficiently undergo hydroboration with borane without a catalyst for the first time.

Disclosed is a method for preparing a boric acid ester using non-catalyzed hydroboration of a carboxylic acid. The method includes: in an inert gas atmosphere, mixing pinacolborane and a carboxylic acid and stirring until uniform in a reaction flask subjected to dehydration and deoxygenation treatments, reacting for 6-12 hours to obtain the boric acid ester, then adding silica gel and methanol, and conducting a hydrolysis reaction to prepare an alcohol compound. The carboxylic acid is acetic acid, caproic acid, pentanoic acid, heptanoic acid, trimethylacetic acid, adipic acid, benzoic acid, 4-bromobenzoic acid, 4-fluorobenzoic acid, 1-naphthoic acid, 2-methoxybenzoic acid, 4-tert-butylbenzoic acid, 4-ethoxybenzoic acid, 2-bromobenzoic acid, 4-iodobenzoic acid, 3-phenylpropionic acid, diphenyl acetic acid, 2-phenylbutyric acid, indole-3-acetic acid, o-carboxyl phenylacetic acid or 2-methyl-5-bromobenzoic acid. The present invention utilizes a carboxylic acid to efficiently undergo hydroboration with borane without a catalyst for the first time.

Disclosed is a method for preparing a boric acid ester using non-catalyzed hydroboration of a carboxylic acid. The method includes: in an inert gas atmosphere, mixing pinacolborane and a carboxylic acid and stirring until uniform in a reaction flask subjected to dehydration and deoxygenation treatments, reacting for 6-12 hours to obtain the boric acid ester, then adding silica gel and methanol, and conducting a hydrolysis reaction to prepare an alcohol compound. The carboxylic acid is acetic acid, caproic acid, pentanoic acid, heptanoic acid, trimethylacetic acid, adipic acid, benzoic acid, 4-bromobenzoic acid, 4-fluorobenzoic acid, 1-naphthoic acid, 2-methoxybenzoic acid, 4-tert-butylbenzoic acid, 4-ethoxybenzoic acid, 2-bromobenzoic acid, 4-iodobenzoic acid, 3-phenylpropionic acid, diphenyl acetic acid, 2-phenylbutyric acid, indole-3-acetic acid, o-carboxyl phenylacetic acid or 2-methyl-5-bromobenzoic acid. The present invention utilizes a carboxylic acid to efficiently undergo hydroboration with borane without a catalyst for the first time.

The present invention provides a process for preparing 6-isopropenyl-3-methyl-9-decenyl acetate (5): wherein Ac represents an acetyl group, the process comprising steps of: subjecting a 2-methyl-2,6-heptadiene compound (1) having a leaving group X at position 1: wherein X represents an acyloxy group having 1 to 10 carbon atoms including the carbon atom of the carbonyl group, an alkanesulfonyloxy group having 1 to 10 carbon atoms, an arenesulfonyloxy group having 6 to 20 carbon atoms, or a halogen atom, to a nucleophilic substitution reaction with a 3-methylpentyl nucleophilic reagent (2) having a protected hydroxyl group at position 5: wherein M represents Li, MgZ.sup.1, ZnZ.sup.1, Cu, CuZ.sup.1, or CuLiZ.sup.1, wherein Z.sup.1 represents a halogen atom or a CH.sub.2CH.sub.2CH(CH.sub.3)CH.sub.2CH.sub.2OR group, and R represents a protecting group for a hydroxyl group, to form a 6-isopropenyl-3-methyl-9-decene compound (3) having a protected hydroxyl group at position 1: wherein R is as defined above; subjecting the 6-isopropenyl-3-methyl-9-decene compound (3) having the protected hydroxyl group at position 1 to a deprotection reaction to form 6-isopropenyl-3-methyl-9-decenol (4); and acetylating 6-isopropenyl-3-methyl-9-decenol (4) to form 6-isopropenyl-3-methyl-9-decenyl acetate (5).

##STR00001##

The present invention provides a process for preparing 6-isopropenyl-3-methyl-9-decenyl acetate (5): wherein Ac represents an acetyl group, the process comprising steps of: subjecting a 2-methyl-2,6-heptadiene compound (1) having a leaving group X at position 1: wherein X represents an acyloxy group having 1 to 10 carbon atoms including the carbon atom of the carbonyl group, an alkanesulfonyloxy group having 1 to 10 carbon atoms, an arenesulfonyloxy group having 6 to 20 carbon atoms, or a halogen atom, to a nucleophilic substitution reaction with a 3-methylpentyl nucleophilic reagent (2) having a protected hydroxyl group at position 5: wherein M represents Li, MgZ.sup.1, ZnZ.sup.1, Cu, CuZ.sup.1, or CuLiZ.sup.1, wherein Z.sup.1 represents a halogen atom or a CH.sub.2CH.sub.2CH(CH.sub.3)CH.sub.2CH.sub.2OR group, and R represents a protecting group for a hydroxyl group, to form a 6-isopropenyl-3-methyl-9-decene compound (3) having a protected hydroxyl group at position 1: wherein R is as defined above; subjecting the 6-isopropenyl-3-methyl-9-decene compound (3) having the protected hydroxyl group at position 1 to a deprotection reaction to form 6-isopropenyl-3-methyl-9-decenol (4); and acetylating 6-isopropenyl-3-methyl-9-decenol (4) to form 6-isopropenyl-3-methyl-9-decenyl acetate (5).

##STR00001##