Fluorine-containing ether compound and method of manufacturing the same, compound and method of manufacturing the same, fluorine-containing ether composition, coating liquid, and article and method of manufacturing the same

A compound expressed by the following formula (B1) or (B2):

• RfO—(Rf1O)m1—(R1)m2—CHO Formula (B1)
• OHC—(R2)m7—O—(Rf2O)m8—(R3)m9—CHO Formula (B2),
• wherein
• Rf is a fluoroalkyl group having a carbon number of from 1 to 20,
• Rf1 and Rf2 are each independently a fluoroalkylene group having a carbon number of from 1 to 6, and when there are a plurality of Rf1 or a plurality of Rf2, the plurality of Rf1 or the plurality of Rf2 may each be identical to or different from each other,
• R1, R2, and R3 are each independently an alkylene group that may have a fluorine atom,
• m1 and m8 are each independently an integer of from 0 to 210, and
• m2, m7, and m9 are each independently 0 or 1.

A method of manufacturing a fluorine-containing ether compound, the method comprising:

• reacting a compound expressed by the following formula (B1) or (B2) and a compound expressed by the following formula (C1):
• RfO—(Rf1O)m1—(R1)m2—CHO Formula (B1)
• OHC—(R2)m7—O—(Rf2O)m8—(R3)m9—CHO Formula (B2)
• (CH2═CH—)n5-Q4(—OH)n6 Formula (C1),
• wherein
• Rf is a fluoroalkyl group having a carbon number of from 1 to 20,
• Rf1 and Rf2 are each independently a fluoroalkylene group having a carbon number of from 1 to 6, and when there are a plurality of Rf1 or a plurality of Rf2, the plurality of Rf1 or the plurality of Rf2 may each be identical to or different from each other,
• R1, R2, and R3 are each independently an alkylene group that may have a fluorine atom,
• Q4 is an (n5+n6)-valent linking group,
• m1 and m8 are each independently an integer of from 0 to 210,
• m2, m7, and m9 are each independently 0 or 1,
• n5 is an integer of from 1 to 20, and
• n6 is an integer of from 1 to 10.

A method of manufacturing a compound expressed by the following formula (B1) or (B2), the method comprising:

• reacting a compound expressed by the following formula (D1) or (D2) with a silicon hydride compound in the presence of a Lewis acid compound to obtain a compound expressed by the following formula (E1) or (E2);
• eliminating Si(R16)3 from the compound expressed by the following formula (E1) or (E2) to obtain a compound expressed by the following formula (F1) or (F2);
• and
• heating the compound expressed by the following formula (F1) or (F2):
• RfO—(Rf1O)m1—(R1)m2—C(═O)OR11 Formula (D1)
• R11OC(═O)—(R2)m7—O—(Rf2O)m8—(R3)m9—C(═O)OR11 Formula (D2)
• RfO—(Rf1O)m1—(R1)m2—CH(OR12)2 Formula (E1)
• (R12O)2CH—(R2)m7—O—(R12O)m8—(R3)m9—CH(OR13)2 Formula (E2)
• RfO—(Rf1O)m1—(R1)m2—CH(OR14)2 Formula (F1)
• (R14O)2CH—(R2)m7—O—(Rf2O)m8—(R3)m9—CH(OR15)2 Formula (F2)
• RfO—(Rf1O)m1—(R1)m2—CHO Formula (B1)
• OHC—(R2)m7—O—(Rf2O)m8—(R3)m9—CHO Formula (B2),
• wherein
• Rf is a fluoroalkyl group having a carbon number of from 1 to 20,
• Rf1 and Rf2 are each independently a fluoroalkylene group having a carbon number of from 1 to 6, and when there are a plurality of Rf1 or a plurality of Rf2, the plurality of Rf1 or the plurality of Rf2 may each be identical to or different from each other,
• R1, R2, and R3 are each independently an alkylene group that may have a fluorine atom,
• R11 is an alkyl group that may have a hydrogen atom or a substituent, and when there are a plurality of R11, the plurality of R11 may be identical to or different from each other,
• R12 and R13 are each independently Si(R16)3 or R11, and at least one of the plurality of R12 and at least one of the plurality of R13 are Si(R16)3,
• R14 and R15 are each independently a hydrogen atom or R11, and at least one of the plurality of R14 and at least one of the plurality of R15 are a hydrogen atom, and
• R16 is a hydrogen atom, a halogen atom, an alkyl group, an aryl group, or an alkoxy group, and the plurality of R16 may be identical to or different from each other,
• m1 and m8 are each independently an integer of from 0 to 210, and
• m2, m7, and m9 are each independently 0 or 1.