A process for producing renewable distillate-range hydrocarbons is provided. The process includes dehydrating a renewable C2-C6 alcohol feedstock to produce an olefin, oligomerizing the olefin the presence of a halometallate ionic liquid catalyst to produce an oligomer product and hydrogenating the oligomer product or fractions thereof to produce saturated distillate-range hydrocarbons.

Provided are a method for efficiently producing an asymmetric conjugated diyne from an inexpensive and safe alternative compound to hydroxylamine hydrochloride and a method for producing a Z,Z-conjugated diene compound from the asymmetric conjugated diyne compound thus obtained. More specifically, provided is a method for producing an asymmetric conjugated diyne compound comprising a step of subjecting a terminal alkyne compound (1): HC≡C—Z.sup.1—Y.sup.1 to a coupling reaction with an alkynyl halide (2): Y.sup.2—Z.sup.2—C≡C—X by using sodium borohydride in water and an organic solvent in the presence of a copper catalyst and a base to obtain the asymmetric conjugated diyne compound (3): Y.sup.2—Z.sup.2—C≡C—C≡C—Z.sup.1—Y.sup.1. In addition, provided is a method for producing a Z,Z-conjugated diene compound by reducing the resulting asymmetric conjugated diyne compound, or the like.

A method of implementing organic synthesis reactions uses a composition containing a metal catalyst originating from a calcined plant. The plants can be from the Brassicaceae, Sapotaceae and Convolvulaceae family, and the metal catalyst contains metal in the M(II) form such as zinc, nickel, manganese, lead, cadmium, calcium, magnesium or copper. Examples of the organic synthesis reactions include halogenations, electrophilic reactions, cycloadditions, transesterification reactions and coupling reactions, among others.

The present invention provides a process to prepare a composite ionic liquid, the process at least comprising the steps: (a) mixing an ammonium salt and a solid aluminium salt to obtain a first mixture; (b) stirring under heating the first mixture of step (a); (c) adding to the first mixture of step (b) one or more solid metal salts to obtain a second mixture, wherein the metal salts are selected from halides, sulfates, or nitrates of aluminium, gallium, copper, iron, zinc, nickel, cobalt, molybdenum and platinum; (d) stirring under heating the second mixture of step (c); (e) adding to the second mixture of step (d) a hydrocarbon to obtain a third mixture; (f) stirring under heating the third mixture of step (e) until the solids of the aluminium salt of step (a), and the solids of the metal salts of step (c) disappear and the mixture is converted into a composite ionic liquid; and (g) cooling the composite ionic liquid of step (f).

The present invention provides a method for selectively functionalizing alkanes through a sequential biocatalytic dehydrogenation followed by isomerization-hydrofunctionalization reaction.

A process for producing renewable distillate-range hydrocarbons is provided. The process includes dehydrating a renewable C2-C6 alcohol feedstock to produce an olefin, oligomerizing the olefin the presence of a halometallate ionic liquid catalyst to produce an oligomer product and hydrogenating the oligomer product or fractions thereof to produce saturated distillate-range hydrocarbons.

A method of implementing organic synthesis reactions uses a composition containing a metal catalyst originating from a calcined plant. The plants can be from the Brassicaceae, Sapotaceae and Convolvulaceae family, and the metal catalyst contains metal in the M(II) form such as zinc, nickel, manganese, lead, cadmium, calcium, magnesium or copper. Examples of the organic synthesis reactions include halogenations, electrophilic reactions, cycloadditions, transesterification reactions and coupling reactions, among others.

The present disclosure provides methods to produce para-xylene, toluene, and other compounds from renewable sources (e.g., cellulose, hemicellulose, starch, sugar) and ethylene in the presence of a catalyst. For example, cellulose and/or hemicellulose may be converted into 2,5-dimethylfuran (DMF), which may be converted into para-xylene by cycloaddition of ethylene to DMF. Para-xylene can then be oxidized to form terephthalic acid.

Described herein are methods of oxidative coupling of aryl boron reagents with sp.sup.3-carbon nucleophiles, and ambient decarboxylative arylation of malonate half-esters via oxidative catalysis.

The present invention discloses a process for preparing perhydrofluorene or alkyl-substituted perhydrofluorene, comprising the steps of: (1) reacting a phenolic compound or an aromatic hydrocarbon compound or an aromatic ketone compound or an aromatic ether compound with a benzyl compound to carry out an alkylation reaction in the presence of a first catalyst, thereby to produce substituted or unsubstituted diphenyl methane, wherein the first catalyst is an acidic catalyst; and (2) reacting the substituted or unsubstituted diphenyl methane with hydrogen gas to carry out an hydrogenation reaction or a hydrodeoxygenation reaction, thereby to produce perhydrofluorene or alkyl-substituted perhydrofluorene, wherein the second catalyst is a physical mixture of a metal catalyst and an acidic catalyst or a metal catalyst loaded on an acidic catalyst.