The present invention relates to a new process for the preparation of Tetraconazole or one of its optically active isomers by means of the fluorination of 2-(2,4-dichlorophenyl)-3-(1H-1,2,4-triazol-1-yl)propan-1-ol.

The present invention relates to a new process for the preparation of Tetraconazole or one of its optically active isomers by means of the fluorination of 2-(2,4-dichlorophenyl)-3-(1H-1,2,4-triazol-1-yl)propan-1-ol.

A compound represented by the following formula (1).

##STR00001##

(in formula (1), R.sup.1 represents a 2n-valent group having 1 to 30 carbon atoms, R.sup.2 to R.sup.5 each independently represent an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, a thiol group or a hydroxyl group, provided that at least one R.sup.4 and/or at least one R.sup.5 represents an alkoxy group having 1 to 30 carbon atoms, m.sup.2 and m.sup.3 are each independently an integer of 0 to 8, m.sup.4 and m.sup.5 are each independently an integer of 0 to 9, provided that m.sup.4 and m.sup.5 are not 0 at the same time, n is an integer of 1 to 4, and p.sup.2 to p.sup.5 are each independently an integer of 0 to 2.)

A compound represented by the following formula (1).

##STR00001##

(in formula (1), R.sup.1 represents a 2n-valent group having 1 to 30 carbon atoms, R.sup.2 to R.sup.5 each independently represent an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, a thiol group or a hydroxyl group, provided that at least one R.sup.4 and/or at least one R.sup.5 represents an alkoxy group having 1 to 30 carbon atoms, m.sup.2 and m.sup.3 are each independently an integer of 0 to 8, m.sup.4 and m.sup.5 are each independently an integer of 0 to 9, provided that m.sup.4 and m.sup.5 are not 0 at the same time, n is an integer of 1 to 4, and p.sup.2 to p.sup.5 are each independently an integer of 0 to 2.)

A method for the processing, by separation technology, of a gas mixture (k) which is formed from a product stream (d) of a reactor (4) for synthesizing dimethyl ether from synthesis gas (b), and which contains at least dimethyl ether, carbon dioxide and at least one other component which is lower-boiling than carbon dioxide, is proposed. The gas mixture (k) is cooled at a first pressure level from a first temperature level to a second temperature level and a fraction of the gas mixture (k) that remains in gaseous form at the second temperature level is washed in an absorption column (16) with a reflux (v) predominantly containing carbon dioxide. The reflux (v) predominantly containing carbon dioxide is at least partially formed from a fraction of the gas mixture (k) which is separated in liquid form during the cooling.

A method for the processing, by separation technology, of a gas mixture (k) which is formed from a product stream (d) of a reactor (4) for synthesizing dimethyl ether from synthesis gas (b), and which contains at least dimethyl ether, carbon dioxide and at least one other component which is lower-boiling than carbon dioxide, is proposed. The gas mixture (k) is cooled at a first pressure level from a first temperature level to a second temperature level and a fraction of the gas mixture (k) that remains in gaseous form at the second temperature level is washed in an absorption column (16) with a reflux (v) predominantly containing carbon dioxide. The reflux (v) predominantly containing carbon dioxide is at least partially formed from a fraction of the gas mixture (k) which is separated in liquid form during the cooling.

There is provided a method for producing a composition containing a purified fluorine-containing ether compound.

A method for producing a composition containing a purified fluorine-containing ether compound, wherein

the fluorine-containing ether compound is represented by

CHX.sup.1X.sup.2CF.sub.2OX.sup.3general formula (1):

wherein X.sup.1 and X.sup.2 are the same or different and represent a hydrogen atom, a fluorine atom, or a trifluoromethyl group, and X.sup.3 represents an alkyl group having 1 to 6 carbon atoms and optionally containing a fluorine atom, provided that X.sup.1 and X.sup.2 are not trifluoromethyl groups at the same time, and the method includes: (A) converting, through a reaction between a fluorine-containing olefin compound represented by

CX.sup.1X.sup.2CF(CF.sub.2).sub.nOX.sup.3general formula (2):,

wherein n represents 0 or 1, and X.sup.1, X.sup.2 and X.sup.3 are the same as described above, provided that when X.sup.1 or X.sup.2 is a trifluoromethyl group, n is 0, and X.sup.1 and X.sup.2 are not trifluoromethyl groups at the same time, and a nitrogen-containing compound in the presence of the fluorine-containing ether compound represented by general formula (1), the fluorine-containing olefin compound represented by general formula (2) into an adduct of the nitrogen-containing compound and/or a fluorine-containing carboxylic acid analogue to obtain a composition containing the fluorine-containing ether compound represented by general formula (1) and the adduct of the nitrogen-containing compound and/or the fluorine-containing carboxylic acid analogue, wherein the nitrogen-containing compound is nitrogen-containing compound A having a structure in which an acyl group is bonded to a nitrogen atom and/or nitrogen-containing compound B that is a tertiary amine compound; and (B) separating the adduct of the nitrogen-containing compound and/or the fluorine-containing carboxylic acid analogue from the composition obtained in step (A) to obtain the composition containing a purified fluorine-containing ether compound.

There is provided a method for producing a composition containing a purified fluorine-containing ether compound.

A method for producing a composition containing a purified fluorine-containing ether compound, wherein

the fluorine-containing ether compound is represented by

CHX.sup.1X.sup.2CF.sub.2OX.sup.3general formula (1):

wherein X.sup.1 and X.sup.2 are the same or different and represent a hydrogen atom, a fluorine atom, or a trifluoromethyl group, and X.sup.3 represents an alkyl group having 1 to 6 carbon atoms and optionally containing a fluorine atom, provided that X.sup.1 and X.sup.2 are not trifluoromethyl groups at the same time, and the method includes: (A) converting, through a reaction between a fluorine-containing olefin compound represented by

CX.sup.1X.sup.2CF(CF.sub.2).sub.nOX.sup.3general formula (2):,

wherein n represents 0 or 1, and X.sup.1, X.sup.2 and X.sup.3 are the same as described above, provided that when X.sup.1 or X.sup.2 is a trifluoromethyl group, n is 0, and X.sup.1 and X.sup.2 are not trifluoromethyl groups at the same time, and a nitrogen-containing compound in the presence of the fluorine-containing ether compound represented by general formula (1), the fluorine-containing olefin compound represented by general formula (2) into an adduct of the nitrogen-containing compound and/or a fluorine-containing carboxylic acid analogue to obtain a composition containing the fluorine-containing ether compound represented by general formula (1) and the adduct of the nitrogen-containing compound and/or the fluorine-containing carboxylic acid analogue, wherein the nitrogen-containing compound is nitrogen-containing compound A having a structure in which an acyl group is bonded to a nitrogen atom and/or nitrogen-containing compound B that is a tertiary amine compound; and (B) separating the adduct of the nitrogen-containing compound and/or the fluorine-containing carboxylic acid analogue from the composition obtained in step (A) to obtain the composition containing a purified fluorine-containing ether compound.

A supercritical ethylene extraction process for selectively recovering a phenolic compound from bio-crude and/or bio-oil comprises providing a reactor containing bio-crude and/or bio-oil, wherein the reactor has an operating pressure, introducing an ethylene solvent at the operating pressure to the reactor, and using the ethylene solvent at the operating pressure to extract the extracted portion from the feedstock, wherein the extracted portion comprises the selected phenolic compound at a concentration equal to or greater than 70 wt % on a dry basis.

A supercritical ethylene extraction process for selectively recovering a phenolic compound from bio-crude and/or bio-oil comprises providing a reactor containing bio-crude and/or bio-oil, wherein the reactor has an operating pressure, introducing an ethylene solvent at the operating pressure to the reactor, and using the ethylene solvent at the operating pressure to extract the extracted portion from the feedstock, wherein the extracted portion comprises the selected phenolic compound at a concentration equal to or greater than 70 wt % on a dry basis.