To provide a process for producing a desired perfluorinated product at a high yield in a fluorination reaction of a partially fluorinated ester. A perfluorinated compound (4) is obtained by fluorinating in a liquid phase a compound (3) (wherein the fluorine content is at least 30 mass %) obtained by reacting a compound (1) and a compound (2), wherein the compound (1) is HOCH.sub.2—R.sup.A—CH.sub.2OH, the compound (2) is X.sup.1C(═O)—C(R.sup.B)(R.sup.C)(R.sup.D), R.sup.A is a bivalent saturated hydrocarbon group or the like which has no hetero atom such as an etheric oxygen atom, X.sup.1 is a halogen atom, and —C(R.sup.B)(R.sup.C)(R.sup.D) is a branched group.

To provide a process for producing a desired perfluorinated product at a high yield in a fluorination reaction of a partially fluorinated ester. A perfluorinated compound (4) is obtained by fluorinating in a liquid phase a compound (3) (wherein the fluorine content is at least 30 mass %) obtained by reacting a compound (1) and a compound (2), wherein the compound (1) is HOCH.sub.2—R.sup.A—CH.sub.2OH, the compound (2) is X.sup.1C(═O)—C(R.sup.B)(R.sup.C)(R.sup.D), R.sup.A is a bivalent saturated hydrocarbon group or the like which has no hetero atom such as an etheric oxygen atom, X.sup.1 is a halogen atom, and —C(R.sup.B)(R.sup.C)(R.sup.D) is a branched group.

A hydrofluoroolefin compound represented by the following general formula (II): Formula (II) where Rf is a linear, branched, or cyclic perfluoroalkyl group having 1-6 carbon atoms, and optionally comprises at least one catenated heteroatom selected from nitrogen or oxygen; n is 0 or 1; X is Cl or Br; with the following proviso: when Rf is CF3, then n is 1.

A hydrofluoroolefin compound represented by the following general formula (II): Formula (II) where Rf is a linear, branched, or cyclic perfluoroalkyl group having 1-6 carbon atoms, and optionally comprises at least one catenated heteroatom selected from nitrogen or oxygen; n is 0 or 1; X is Cl or Br; with the following proviso: when Rf is CF3, then n is 1.

Methods of modifying the rate of systemic absorption of a drug administered to a subject by a pulmonary route, the method comprising covalently conjugating a hydrophilic polymer to a drug, wherein the drug has a half-life of elimination from the lung of less than about 180 minutes, to form a drug-polymer conjugate, wherein the drug-polymer conjugate has a net hydrophilic character and a weight average molecular weight of from about 50 to about 20,000 Daltons, and wherein the half-life of elimination from the lung of the drug-polymer conjugate is at least about 1.5-fold greater than the half-life of elimination from the lung of the drug, wherein the half-life of elimination from the lung is measured by bronchoalveolar lavage followed by assaying residual lung material.

Methods of modifying the rate of systemic absorption of a drug administered to a subject by a pulmonary route, the method comprising covalently conjugating a hydrophilic polymer to a drug, wherein the drug has a half-life of elimination from the lung of less than about 180 minutes, to form a drug-polymer conjugate, wherein the drug-polymer conjugate has a net hydrophilic character and a weight average molecular weight of from about 50 to about 20,000 Daltons, and wherein the half-life of elimination from the lung of the drug-polymer conjugate is at least about 1.5-fold greater than the half-life of elimination from the lung of the drug, wherein the half-life of elimination from the lung is measured by bronchoalveolar lavage followed by assaying residual lung material.

The invention relates to a new industrial process for manufacturing of perfluoro(methylvinylether) (PFMVE), and of 1,1,2,2-tetrafluoro-1-(trifluoromethoxy)ethane (TFTFME) (E 227), involving reactions in liquid phase and performing reactions, for example, in a (closed) column reactor or in a microreactor, respectively. The invention also relates to a new industrial process for manufacturing of perfluoro(methyl vinyl ether) (PFMVE) by HF-elimination from the compound 1,1,2,2-tetrafluoro-1-(trifluoromethoxy)ethane (TFTFME) (E 227). The invention also relates to a new industrial process for manufacturing of the compound 1,1,2,2-tetrafluoro-1-(trifluoromethoxy)ethane (TFTFME) (E 227) by selective fluorination of the compound HFE-254 (1,1,2,2-tetrafluoro-1-(methoxy)ethane), i.e., perfluorination of only the CH.sub.3O-group (i.e., methoxy-group) of the compound HFE-254 is selectively fluorinated to a CF.sub.3O-group (i.e., trifluoromethoxy-group).

The invention relates to a new industrial process for manufacturing of perfluoro(methylvinylether) (PFMVE), and of 1,1,2,2-tetrafluoro-1-(trifluoromethoxy)ethane (TFTFME) (E 227), involving reactions in liquid phase and performing reactions, for example, in a (closed) column reactor or in a microreactor, respectively. The invention also relates to a new industrial process for manufacturing of perfluoro(methyl vinyl ether) (PFMVE) by HF-elimination from the compound 1,1,2,2-tetrafluoro-1-(trifluoromethoxy)ethane (TFTFME) (E 227). The invention also relates to a new industrial process for manufacturing of the compound 1,1,2,2-tetrafluoro-1-(trifluoromethoxy)ethane (TFTFME) (E 227) by selective fluorination of the compound HFE-254 (1,1,2,2-tetrafluoro-1-(methoxy)ethane), i.e., perfluorination of only the CH.sub.3O-group (i.e., methoxy-group) of the compound HFE-254 is selectively fluorinated to a CF.sub.3O-group (i.e., trifluoromethoxy-group).

The invention relates to a new industrial process for manufacturing of perfluoro(methylvinylether) (PFMVE), and of 2-fluoro-1,2-dichloro-trifluoro-methoxyethylene (FCTFE), involving reactions in liquid phase and performing reactions in a microreactor. The invention also relates to a new industrial process for manufacturing of perfluoro(methyl vinyl ether) (PFMVE) by fluorination, i.e., perfluorination, of 2-fluoro-1,2-dichloro-trifluoromethoxy-ethylene (FCTFE) with HF (hydrogen fluoride) in the presence of a Lewis acid catalyst, again performing the reaction in liquid phase, and preferably in a microreactor.

The invention relates to a new industrial process for manufacturing of perfluoro(methylvinylether) (PFMVE), and of 2-fluoro-1,2-dichloro-trifluoro-methoxyethylene (FCTFE), involving reactions in liquid phase and performing reactions in a microreactor. The invention also relates to a new industrial process for manufacturing of perfluoro(methyl vinyl ether) (PFMVE) by fluorination, i.e., perfluorination, of 2-fluoro-1,2-dichloro-trifluoromethoxy-ethylene (FCTFE) with HF (hydrogen fluoride) in the presence of a Lewis acid catalyst, again performing the reaction in liquid phase, and preferably in a microreactor.