The invention relates to a method for production of oxymethylene ether of the general formula CH.sub.3O—(CH.sub.2O).sub.m—CH.sub.3 in a liquid phase process, wherein 1≤m≤10. In a catalytic reaction, molecular oxygen or an oxygen-containing oxidant and methanol, formaldehyde, and/or methyl formate are used as reactants in a solution and are converted by means of a vanadium-oxygen compound or a salt thereof as catalyst in the solution which vanadium-oxygen compound contains vanadium in the oxidation stage +IV or +V. The catalyst reduced during the catalytic reaction is restored to its starting state by oxidation by means of the molecular oxygen or the oxygen-containing oxidant.

The invention relates to a method for production of oxymethylene ether of the general formula CH.sub.3O—(CH.sub.2O).sub.m—CH.sub.3 in a liquid phase process, wherein 1≤m≤10. In a catalytic reaction, molecular oxygen or an oxygen-containing oxidant and methanol, formaldehyde, and/or methyl formate are used as reactants in a solution and are converted by means of a vanadium-oxygen compound or a salt thereof as catalyst in the solution which vanadium-oxygen compound contains vanadium in the oxidation stage +IV or +V. The catalyst reduced during the catalytic reaction is restored to its starting state by oxidation by means of the molecular oxygen or the oxygen-containing oxidant.

The present invention relates to a method for producing polyoxymethylene dimethyl ether by introducing a formaldehyde source and at least one compound of the formula (I)

H.sub.3C—O—R  (I) where R is H or —(CH.sub.2O).sub.x—CH.sub.3 with x being 0 or 1
as reactants into a reactive distillation unit and reacting them to give polyoxymethylene dimethyl ether, wherein the method produces polyoxymethylene dimethyl ether exclusively in the reactive distillation unit.

The present invention relates to a method for producing polyoxymethylene dimethyl ether by introducing a formaldehyde source and at least one compound of the formula (I)

H.sub.3C—O—R  (I) where R is H or —(CH.sub.2O).sub.x—CH.sub.3 with x being 0 or 1
as reactants into a reactive distillation unit and reacting them to give polyoxymethylene dimethyl ether, wherein the method produces polyoxymethylene dimethyl ether exclusively in the reactive distillation unit.

This disclosure relates generally to cannabinoid derivatives, pharmaceutical compositions comprising them, and methods of using the cannabinoid derivatives.

The present invention relates to a 6-hydroxy-3-hexenyl alkoxymethyl ether compound of the following general formula (1): HOCH.sub.2CH.sub.2CH═CHCH.sub.2CH.sub.2OCH.sub.2OCH.sub.2R′ (1), R.sup.1 representing a hydrogen atom, an n-alkyl group having 1 to 9 carbon atoms, or a phenyl group; and also relates to a process for preparing a 3,13-octadecadien-1-ol compound of the following formula (6): CH.sub.3(CH.sub.2).sub.3CH═CH(CH.sub.2).sub.8CH═CHCH.sub.2CH.sub.2OH (6) from the 6-hydroxy-3-hexenyl alkoxymethyl ether compound (1).

The present invention relates to a 6-hydroxy-3-hexenyl alkoxymethyl ether compound of the following general formula (1): HOCH.sub.2CH.sub.2CH═CHCH.sub.2CH.sub.2OCH.sub.2OCH.sub.2R′ (1), R.sup.1 representing a hydrogen atom, an n-alkyl group having 1 to 9 carbon atoms, or a phenyl group; and also relates to a process for preparing a 3,13-octadecadien-1-ol compound of the following formula (6): CH.sub.3(CH.sub.2).sub.3CH═CH(CH.sub.2).sub.8CH═CHCH.sub.2CH.sub.2OH (6) from the 6-hydroxy-3-hexenyl alkoxymethyl ether compound (1).

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.

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 process by which the raw material, a gas comprising mainly hydrogen, carbon monoxide and carbon dioxide, is introduced into a first reactor together with a catalyst, in which one or more reactions take place that produce methanol or dimethyl ether or both, which are then introduced into a second reactor adding oxygen and a catalyst and producing formaldehyde and a minority of dimethyl ether, and where there may be an excess of water, such water being extracted from the process and the remaining products being introduced into the third reactor with, optionally, an additive, and such raw material is exposed to catalysts and under an atmosphere at medium temperature and pressure, in order to produce three or four groups of chemical reactions that, after extracting most of the water that is generated as a residue during the process, produces as a result a liquid multifunctional product that can be used as a solvent, a foaming agent or an oxygenated fuel; said product, normally a fluid, comprises polyoxymethylene dimethyl ethers with molecular formula CH3O(CH2O)nCH3 wherein n has a value between 1 and 7.