# US 9,040,760 B2 · Process for producing 2,3,3,3-tetrafluoropropene

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- Number: US 9,040,760 B2
- Document ID: US9040760B2
- Status: Granted
- Kind: B2
- Application number: 13/879,668
- Filed: 2011-10-27
- Published: 2013-08-22
- Granted: 2015-05-26
- Earliest claimed: 2010-10-27
- Assignees: Daikin Industries, Ltd.
- Applicants: Kazuhiro Takahashi; Yuzo Komatsu; Akinori Ueda
- Inventors: Kazuhiro Takahashi; Yuzo Komatsu; Akinori Ueda
- Web page: https://patentgrep.com/patent/US9040760B2

## CPC

- C07C 17/25: by splitting-off hydrogen halides from halogenated hydrocarbons
- C07C 17/087: to unsaturated halogenated hydrocarbons
- C07C 17/20: of halogen atoms by other halogen atoms
- C07C 17/206: {the other compound being HX}
- C12Q 1/686: Polymerase chain reaction [PCR]
- G01N 21/6428: {Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes" (in vivo A61B5/00; immunoassay G01N33/53)}
- G01N 21/6486: {Measuring fluorescence of biological material, e.g. DNA, RNA, cells (G01N21/6428 takes precedence)}
- G01N 2021/6439: {with indicators, stains, dyes, tags, labels, marks}
- G01N 2201/061: Sources
- Y02P 20/582: Recycling of unreacted starting or intermediate materials
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C12Q: MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS (immunoassay G01N33/53); COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
- G01N: INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES (measuring or testing apparatus or processes other than immunoassay, involving enzymes or microorganisms C12M, C12Q)
- Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS

## Abstract

This invention provides a process for producing 2,3,3,3-tetrafluoropropene, the process comprising: (1) a first reaction step of reacting hydrogen fluoride with at least one chlorine-containing compound selected from the group consisting of a chloropropane represented by Formula (1): CClX2CHClCH2Cl, wherein each X is the same or different and is CI or F, a chloropropene represented by Formula (2): CClY2CCl═CH2, wherein each Y is the same or different and is CI or F, and a chloropropene represented by Formula (3): CZ2═CClCH2Cl, wherein each Z is the same or different and is CI or F in a gas phase in the absence of a catalyst while heating; and (2) a second reaction step of reacting hydrogen fluoride with a reaction product obtained in the first reaction step in a gas phase in the presence of a fluorination catalyst while heating. According to the process of this invention, 2,3,3,3-tetrafluoropropene (HFO-1234yf) can be obtained with high selectivity, and catalyst deterioration can be suppressed.

## Claims

### Claim 1

A process for producing 2,3,3,3-tetrafluoropropene, the process comprising:
(1) a first reaction step of reacting hydrogen fluoride with at least one chlorine-containing compound selected from the group consisting of a chloropropane represented by Formula (1):
CClX2CHClCH2Cl, wherein each X is the same or different and is Cl or F, a chloropropene represented by Formula (2): CClY2CCl═CH2, wherein each Y is the same or different and is Cl or F, and a chloropropene represented by Formula (3): CZ2═CClCH2Cl, wherein each Z is the same or different and is Cl or F in a gas phase in the absence of a catalyst while heating; and
(2) a second reaction step of reacting a reaction product obtained in the first reaction step with hydrogen fluoride in a gas phase in the presence of a fluorination catalyst while heating,
wherein the second reaction step uses, as a starting material, CF3CCl═CH2 (HCFO-1233xf) and at least one chlorine-containing compound selected from the group consisting of CF2ClCHClCH2Cl (HCFC-242dc) and CF2ClCCl═CH2 (HCFO-1232xf), and
wherein the CF3CCl═CH2 (HCFO-1233xf) and the at least one chlorine-containing compound are contained in the reaction product obtained in the first reaction step.

### Claim 2 (depends on 1)

The process according to claim 1, wherein the reaction temperature in the first reaction step is 250 to 600° C., and the reaction temperature in the second reaction step is 200 to 500° C.

### Claim 3 (depends on 1)

The process according to claim 1, wherein the amount of hydrogen fluoride in the first reaction step is 1 to 100 moles per mole of the chlorine-containing compound used as a starting material, and the amount of hydrogen fluoride in the second reaction step is 1 to 50 moles per mole of the chlorine-containing compound used as a starting material in the first reaction step.

### Claim 4 (depends on 1)

The process according to claim 1, wherein the fluorination catalyst used in the second reaction step is at least one member selected from the group consisting of chromium oxides, chromium oxyfluorides, aluminium fluorides, aluminum oxyfluorides, and metal fluorides.

### Claim 5 (depends on 1)

The process according to claim 1, wherein after removing hydrogen chloride from the reaction product obtained in the first reaction step, the CF3CCl═CH2 (HCFO-1233xf) and the at least one chlorine-containing compound contained in the reaction product obtained in the first reaction step are used as a starting material in the second reaction step.

### Claim 6 (depends on 1)

The process according to claim 1, wherein after reducing the amount of hydrogen fluoride contained in the reaction product obtained in the first reaction step, the CF3CCl═CH2 (HCFO-1233xf) and the at least one chlorine-containing compound contained in the reaction product obtained in the first reaction step are used as a starting material in the second reaction step.

### Claim 7 (depends on 1)

The process according to claim 1, wherein the first reaction step is conducted in a reactor made of an alloy containing 30% or more by weight of nickel.

### Claim 8 (depends on 7)

The process according to claim 7, wherein the alloy containing 30% or more by weight of nickel is at least one member selected from the group consisting of Hastelloy, Inconel, Monel, and Incoloy.