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US 6,586,626 B2Granted
Process for producing a fluorine-containing compound by liquid phase fluorination
AssigneeAsahi Glass Company, Limited
InventorsTakashi Okazoe, Kunio Watanabe, Shin Tatematsu, Hidenobu Murofushi
Life of this patent
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Abstract
The invention provides a process for producing a fluorine-containing compound from an inexpensive material. Namely, Compound I such as RACH2OH is reacted with Compound II such as XCORB to form Compound III such as RACH2OCORB, followed by fluorination in a liquid phase to form Compound IV such as RAFCF2OCORBF, which is converted to Compound V such as RAFCOF and/or Compound VI such as RBFCOF. RA is an alkyl group or the like, RB is a perhalogenoalkyl group or the like, RAF and RBF are fluorinated RA and RB, and X is halogen.
Claims24
A process for producing a fluorine-containing compound, which comprises:
- reacting compound (I) with compound (II) to form compound (III) having a fluorine content ranging from 30-76% by wt;
- fluorinating compound (III) in a liquid phase to form compound (IV);
- and
- converting compound (IV) to compound (V), compound (VI) or a combination of compounds (V) and (VI):
- RA—E1 (I)
- RB—E2 (II)
- RA—E-RB (III)
- RAF—EF-RBF (IV)
- RAF—EF1 (V)
- RBF—EF2 (VI)
- wherein
- RA, RB:
- each independently is a monovalent saturated hydrocarbon group, a halogeno monovalent saturated hydrocarbon group, a hetero atom-containing monovalent saturated hydrocarbon group, a halogeno (hetero atom-containing monovalent saturated hydrocarbon) group, or a monovalent organic group (RH) which can be converted to RHF by a fluorination reaction in a liquid phase,
- RHF:
- a group having at least one hydrogen atom in a group selected from the group consisting of a monovalent saturated hydrocarbon group, a partially halogeno monovalent saturated hydrocarbon group, a hetero atom-containing monovalent saturated hydrocarbon group, and a partially halogeno (hetero atom-containing monovalent saturated hydrocarbon) group, substituted by a fluorine atom;
- RAF, RBF:
- RAF is a group corresponding to RA, and RBF is a group corresponding to RB;
- and in the instance where each of RA and RB is a monovalent saturated hydrocarbon group, a halogeno monovalent saturated hydrocarbon group, a hetero atom-containing monovalent saturated hydrocarbon group, or a halogeno (hetero atom-containing monovalent saturated hydrocarbon) group, RAF and RBF are the same groups as RA and RB, respectively, or are RA and RB groups each substituted by at least one fluorine atom, and in the case where RA and RB are monovalent organic groups (RH), RAF and RBF are RHF, respectively;
- E1, E2:
- reactive groups which are mutually reactive to form a bivalent connecting group (E);
- E:
- a bivalent connecting group formed by the reaction of E1 and E2;
- EF:
- the same group as E, or a group in which E is fluorinated, provided that at least one of RAF, RBF and EF, is not the same group as the corresponding RA, RB and E, respectively;
- EF1, EF2:
- each independently is a group formed by dissociation of EF.
23 more elements
A compound of one of the following formulas:
- CF3(CF3CF2CF2O)CFCOOCH2CH(OCH2CH2CH3)CH3,
- CF3CF2COOCH2CH2CHClCH2Cl,
- CF2ClCFClCF2COOCH2CH2CHClCH2Cl,
- CF2ClCF2CFClCOOCH2CH2CHClCH2Cl,
- CF3(CF3CF2CF2O)CFCOOCH2CH(OCH2CH2CHClCH2Cl)CH3,
- CF3(CF3CF2CF2O)CFCOOCH2CH(OCH2Cy)CH3,
- CF3(CF3CF2CF2O)CFCOOCH2CH(OCH2Ph)CH3,
- CF3(CF3CF2CF2O)CFCOOCH2CH(O(CH2)9CH3)CH3,
- CF3(CF3CF2CF2O)CFCOO(CH2)3OCH2Ph,
- CF3(CF3CF2CF2O)CFCOO(CH2)3OCH2CH═CH2,
- wherein Cy is a cyclohexyl group and Ph is a phenyl group.
8 more elements
A compound of one of the following formulas:
- CF3(CF3CF2CF2O)CFCOOCF2CF(OCF2CF2CF3)CF3,
- CF3CF2COOCF2CF2CFClCF2Cl,
- CF2ClCFClCF2COOCF2CF2CFClCF2Cl,
- CF2ClCF2CFClCOOCF2CF2CFClCF2Cl,
- CF3(CF3CF2CF2O)CFCOOCF2CF(OCF2CF2CFClCF2Cl)CF3,
- CF3(CF3CF2CF2O)CFCOOCF2CF(OCF2CyF)CF3,
- CF3(CF3CF2CF2O)CFCOOCF2CF(O(CF2)9CF3)CF3,
- CF3(CF3CF2CF2O)CFCOO(CF2)3OCF2CyF,
- CF3(CF3CF2CF2O)CFCOO(CF2)3OCF2CF2CF3,
- wherein CyF is a perfluorocyclohexyl group.
7 more elements
A compound of one of the following formulas:
- FCOCF(O(CF2)9CF3)CF3
- FCO(CF2)2OCF2CYF.
A process for producing a fluorine-containing compound, which comprises:
- reacting compound (I) of the formula RA—E1 having a fluorine content of less than 10 wt %, wherein RA is a monovalent C1-20 saturated hydrocarbon group, a halogeno monovalent C1-20 saturated hydrocarbon group, a oxygen atom-containing monovalent C1-8 saturated hydrocarbon group bonded to a C1-20 saturated hydrocarbon group , a halogeno (oxygen atom-containing monovalent saturated hydrocarbon) group, or a monovalent organic group (RH) which can be converted to RHF by the substitution of fluorine for at least one hydrogen atom in RA and E1 is —CH2OH, with compound (II) having the formula RB—E2, wherein RB independently is as defined for RA and E2 is —COX or —SO2X, thereby forming compound (III) having the formula RA—E—RB which has a fluorine content ranging from 30-76% by wt, wherein RA and RB are as defined above and E is —COOCH2— or —SO2OCH2—;
- fluorinating compound (III) in a liquid phase to form compound (IV) of the formula RAF—EF-RBF, wherein RAF and RBF represent RA and RB respectively which are substituted by fluorine in the fluorination reaction and EF is the same as E as defined above or fluorinated E, provided that at least one of RAF, RBF and EF is not the same group as the corresponding RA, RB and E respectively;
- and
- converting compound (IV) to compound (V) having the formula RAF—EF1, wherein RAF is as defined above and EF1 is formed by the dissociation of EF, or to a compound (VI) having the formula RBF—EF2, wherein RBF is as defined above and EF2 is formed by the dissociation of EF, or to both compound (V) and compound (VI).
1 more element
A process for producing a fluorine-containing compound, which comprises:
- reacting a compound (I) of a formula selected from the group consisting of CH3(CH3CH2CH2O)CHCH2OH, CH3(CH2ClCHClCH2CH2O)CHCH2OH, CH3(BrCH2CH2O)CHCH2OH, CH3[CH2ClCHClCH2CH(CH3)O]CHCH2OH, CH3CH2CH2OH, CH2═CHCH2OH, CH2ClCHClCH2CH2OH, CH2ClCH2OH, CH2BrCH2OH CyCH2OCH(CH3)CH2OH, PhCH2OCH(CH3)CH2OH, CH3(CH2)9OCH(CH3)CH2OH PhCH2O(CH2)2CH2OH, CH2═CHCH2O(CH2)2CH2OH, CH3CH2CH2OCH2CH(CH3)OH, CF2ClCFClCH2CH2OH,
- wherein Cy is cyclohexyl and Ph is phenyl, with a compound (II) of a formula selected from the group consisting of CF2CF2COF, CF2ClCFClCF2COF, CF2ClCF2CFClCOF, CF3(CF3CF2CF2O)CFCOF;
- CF3(CF2ClCFClCF2CF2O)CFCOF, CClF2COF, CF3(CF2BrCF2O)CFCOF, CF3[CF2ClCFClCF2CF(CF3)O]CFCOF, CF3CF2CF2OCF(CF3)CF2OCF(CF3)COF, CF3(CH3CH2CH2O)CFCOF, CH2ClCHClCH2COCl,
- thereby forming an ester intermediate (III);
- fluorinating ester intermediate (III) in a liquid phase to form a more extensively fluorinated compound (IV);
- and
- decomposing compound (IV) thermally or in the presence of an electrophile or a nucleophile, thereby forming a fluorinated compound (V) or fluorinated compound (VI) or both.
4 more elements
Dependencies are inferred from the claim text.