Method for separating perfluoro(poly)ether-group-containing alcohol compounds

A method for chromatographically separating a mixture comprising:

• a perfluoro(poly)ether group-containing nonalcohol compound represented by the following formula (1),
• a perfluoro(poly)ether group-containing monoalcohol compound represented by the following formula (2), and
• a perfluoro(poly)ether group-containing dialcohol compound represented by the following formula (3):
• A-Pf-A (1)
• A-Pf-Z (2)
• Z-Pf-Z (3)
• wherein
• Pf represents a divalent perfluoropolyether group,
• A each independently represents an R1— group, an R1—O— group, an R2O—CH2—R3— group, or an R2O—CH2—R3—O— group,
• R1 each independently represents an alkyl group,
• R2 each independently represents an alkyl group,
• R3 each independently represents a divalent organic group containing 1 to 4 carbon atoms,
• Z each independently represents an —R5—CH2OH group or an —O—R5—CH2OH group, and
• R5 each independently represents a bond or a divalent organic group containing 1 to 4 carbon atoms,
• the method comprising:
• (i) adsorbing the mixture onto a stationary phase,
• (ii) eluting the perfluoro(poly)ether group-containing nonalcohol compound represented by formula (1) by a mobile phase selected from nonpolar solvents and low-polarity solvents to separate the perfluoro(poly)ether group-containing nonalcohol compound represented by formula (1) from the perfluoro(poly)ether group-containing monoalcohol compound represented by formula (2) and the perfluoro(poly)ether group-containing dialcohol compound represented by formula (3),
• (iii) eluting the perfluoro(poly)ether group-containing monoalcohol compound represented by formula (2) by one mobile phase of a single solvent in a liquid state selected from the group consisting of hydrochlorofluorocarbons, hydrofluoroethers, fluorine-containing ester solvents, and fluorine-containing aromatic solvents to separate the perfluoro(poly)ether group-containing monoalcohol compound represented by formula (2) from the perfluoro(poly)ether group-containing dialcohol compound represented by formula (3), and
• (iv) increasing a temperature of the stationary phase to elute the perfluoro(poly)ether group-containing dialcohol compound represented by formula (3) by one mobile phase of a single solvent in a liquid state selected from the group consisting of hydrofluorocarbons, hydrochlorofluorocarbons, hydrofluoroethers, fluorine-containing ester solvents, and fluorine-containing aromatic solvents.

A method for producing a perfluoro(poly)ether group-containing monoalcohol compound represented by the following formula (2):

• A-Pf-Z (2)
• wherein
• Pf represents a divalent perfluoropolyether group,
• A each independently represents an R1— group, an R1—O— group, an R2O—CH2—R3— group, or an R2O—CH2—R3—O— group,
• R1 each independently represents an alkyl group,
• R2 each independently represents an alkyl group,
• R3 each independently represents a divalent organic group containing 1 to 4 carbon atoms,
• Z each independently represents an —R5—CH2OH group or an —O—R5—CH2OH group, and
• R5 each independently represents a bond or a divalent organic group containing 1 to 4 carbon atoms,
• the method comprising:
• adsorbing a mixture comprising the perfluoro(poly)ether group-containing monoalcohol compound represented by formula (2) and a perfluoro(poly)ether group-containing dialcohol compound represented by the following formula (3):
• Z-Pf-Z (3)
• wherein Pf, A, and Z are as defined above onto a stationary phase by using the same solvent as a solvent used as a mobile phase described below, and eluting the perfluoro(poly)ether group-containing monoalcohol compound represented by formula (2) from the mixture, by using one mobile phase of a single solvent in a liquid state selected from the group consisting of hydrochlorofluorocarbons, hydrofluoroethers, fluorine-containing ester solvents, and fluorine-containing aromatic solvents in chromatography using a stationary phase to purify the perfluoro(poly)ether group-containing monoalcohol compound represented by formula (2).

A method for producing a perfluoro(poly)ether group-containing dialcohol compound represented by the following formula (3):

• Z-Pf-Z (3)
• wherein
• Pf represents a divalent perfluoropolyether group,
• R1 each independently represents an alkyl group,
• R2 each independently represents an alkyl group,
• R3 each independently represents a divalent organic group containing 1 to 4 carbon atoms,
• Z each independently represents an —R5—CH2OH group or an —O—R5—CH2OH group, and
• R5 each independently represents a bond or a divalent organic group containing 1 to 4 carbon atoms,
• the method comprising:
• eluting a perfluoro(poly)ether group-containing monoalcohol compound represented by the following formula (2):
• A-Pf-Z (2)
• wherein
• Pf, and Z are as defined above, and
• A each independently represents an R1— group, an R1—O— group, an R2O—CH2—R3— group, or an R2O—CH2—R3—O— group,
• from a mixture comprising the perfluoro(poly)ether group-containing dialcohol compound represented by formula (3) and the perfluoro(poly)ether group-containing monoalcohol compound represented by formula (2) by using one mobile phase of a single solvent in a liquid state selected from the group consisting of hydrochlorofluorocarbons, hydrofluoroethers, fluorine-containing ester solvents, and fluorine-containing aromatic solvents in chromatography using a stationary phase, and then increasing a column temperature to elute the perfluoro(poly)ether group-containing dialcohol compound represented by formula (3) by using one mobile phase of a single solvent in a liquid state selected from the group consisting of hydrofluorocarbons, hydrochlorofluorocarbons, hydrofluoroethers, fluorine-containing ester solvents, and fluorine-containing aromatic solvents.