Production method for composition containing 1,2-dichloro-3,3,3-trifluoropropene (HCFO-1223xd) and/or 1,1,2-trichloro-3,3,3-trifluoropropene (CFO-1213xa)

Patent metadata

Field	Value
Publication number	US-9902670-B2
Application number	US-201515307956-A
Country	US
Kind code	B2
Filing date	May 14, 2015
Priority date	May 16, 2014
Publication date	Feb 27, 2018
Grant date	Feb 27, 2018

Abstract

The present invention provides a method that produces a composition containing 1223xd and/or 1213xa by a gas-phase reaction, and that achieves production efficiency higher than known methods. The present invention provides a method for producing a composition containing at least one fluorine-containing olefin selected from 1,2-dichloro-3,3,3-trifluoropropene (HCFO-1223xd) and 1,1,2-trichloro-3,3,3-trifluoropropene (CFO-1213xa), the method comprising subjecting at least one starting compound selected from a chlorine-containing alkane represented by Formula (1-1): CF 3 CHXCHX 2 , wherein each X is independently H or Cl, with the proviso that at least one X represents Cl, and a chlorine-containing alkene represented by Formula (1-2): CF 3 CX═CX 2 , wherein each X is independently H or Cl, with the proviso that at least one X represents Cl, to a gas-phase oxychlorination reaction in a temperature range of 380° C. or lower in the presence of oxidative gas and hydrogen chloride gas.

First claim

The invention claimed is:

1. A method for producing a composition containing at least one fluorine-containing olefin selected from 1,2-dichloro-3,3,3-trifluoropropene (HCFO-1223xd) and 1,1,2-trichloro-3,3,3-trifluoropropene (CFO-1213xa),
the method comprising
subjecting at least one starting compound selected from a chlorine-containing alkane of the following Formula (1-1): CF 3 CHXCHX 2 , wherein each X is independently H or Cl, with the proviso that at least one X represents Cl, and a chlorine-containing alkene of the following Formula (1-2): CF 3 CX=CX 2 , wherein each X is independently H or Cl, with the proviso that at least one X represents Cl,

to a gas-phase oxychlorination reaction in a temperature range of 380° C. or lower in the presence of oxygen gas and hydrogen chloride gas.

2. The production method according to claim 1 , wherein the starting compound is at least one member selected from the group consisting of 2,3-dichloro-1,1,1-trifluoropropane (HCFC-243 db), 3,3-dichloro-1,1,1-trifluoropropane (HCFC-243fa), 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf), and 1-chloro-3,3,3-trifluoropropene (HCFO-1233zd).

3. The production method according to claim 1 , wherein the starting compound is 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf).

4. The production method according to claim 1 ,
the method comprising
subjecting at least one starting compound precursor selected from a chlorine-containing alkane of the following Formula (2-1): CY 3 CHXCHX 2 , wherein each X is independently H or Cl, with the proviso that at least two X's represent Cl, and each Y is independently F or Cl, and

a chlorine-containing alkene of the following Formula (2-2): CX 3 CX=CX 2 , wherein each X is independently H or Cl, with the proviso that at least two X's represent Cl, to a gas-phase fluorination reaction using hydrogen fluoride to convert the precursor into the starting compound; and
subjecting the starting compound obtained by the conversion to a gas-phase oxychlorination reaction in a temperature range of 380° C. or lower in the presence of oxygen gas and hydrogen chloride gas to obtain the composition.

5. The production method according to claim 4 , wherein the starting compound precursor is at least one member selected from the group consisting of
1,1,1,3,3-pentachloropropane (HCC-240fa), 1,1,1,3-tetrachloropropane (HCC-250fb), 1 , 1 , 2 , 3 -tetrachloro-1-fluoropropane (HCFC-241db), 1,2,3-trichloro-1,1-difluoropropane (HCFC-242dc), 1,1,3,3-tetrachloro-1-fluoropropane (HCFC-241fa), 1,3,3-trichloro-1,1-difluoropropane (HCFC-242fa), 1,1,2,3-tetrachloropropene (HCO-1230xa), 2,3,3,3-tetrachloropropene (HCO-1230xf), and 1,1,3,3-tetrachloropropene (HCO-1230za).

6. The production method according to claim 1 ,
the method comprising
a step of generating hydrogen chloride gas by subjecting a part of the starting compound to a gas-phase fluorination reaction using hydrogen fluoride,

wherein the generated hydrogen chloride gas is used as part or all of the hydrogen chloride gas used in the gas-phase oxychlorination reaction.

7. The production method according to claim 4 , wherein part or all of the hydrogen chloride gas used in the gas-phase oxychlorination reaction is hydrogen chloride gas generated when the starting compound precursor is subjected to a gas-phase fluorination reaction using hydrogen fluoride.

8. The production method according to claim 1 ,
the method comprising
a step of separating a high-boiling-point fraction having a boiling point of 30° C. or higher at atmospheric pressure and containing at least one of HCFO-1223xd and CFO-1213xa from the composition.

9. The production method according to claim 1 , the method comprising:
a step of separating a high-boiling-point fraction having a boiling point of 30° C. or higher at atmospheric pressure and containing at least one of HCFO-1223xd and CFO-1213xa from the composition; and
a step of recycling a part or all of compounds from the residue after separation, contain three carbon atoms, and have a boiling point lower than that of HCFO-1223xd, into the gas-phase oxychlorination reaction.

10. The production method according to claim 1 , wherein the oxygen gas is used at the time of the gas-phase oxychlorination reaction in an amount of 3equivalents or less, relative to total organic substances.

11. The production method according to claim 1 , wherein the gas-phase oxychlorination reaction is performed in a temperature range of 300 to 380° C.

12. The production method according to claim 1 , wherein the gas-phase oxychlorination reaction is performed using a catalyst containing at least one member selected from the group consisting of chromium, copper, tin, ruthenium, vanadium, niobium, molybdenum, rhodium, antimony, osmium, manganese, cobalt, and platinum.

13. The production method according to claim 12 , wherein the catalyst is supported on at least one carrier selected from the group consisting of chromia, alumina, zirconia, titania, chromium fluoride, and aluminium fluoride.

Assignees

• Daikin Ind Ltd

Inventors

• Karube Daisuke
• Ohkubo Shun
• Takakuwa Tatsuya

Classifications

• C07C17/06 Primary

  combined with replacement of hydrogen atoms by halogens · CPC title

• C07C17/25

  by splitting-off hydrogen halides from halogenated hydrocarbons · CPC title

• Y02P20/582

  Recycling of unreacted starting or intermediate materials · CPC title

• B01J23/26

  Chromium · CPC title

• C07C19/10

  and chlorine · CPC title