422-56-0

Basic information

• Product Name: 3,3-Dichloro-1,1,1,2,2-pentafluoropropane
• Synonyms: HCFC-225CA;DICHLOROPENTAFLUOROPROPANE;1,1-DICHLORO-2,2,3,3,3-PENTAFLUOROPROPANE;3,3-DICHLORO-1,1,1,2,2-PENTAFLUOROPROPANE;1,1,1,2,2-pentafluoro-3,3-dichloropropane;1,1-Dichlor-2,2,3,3,3-pentafluorpropan;1,1-Dichloro-2,2,3,3,3-pentafluoropropane(HCFC-225ca);Propane,3,3-dichloro-1,1,1,2,2-pentafluoro-
• CAS NO: 422-56-0
• Molecular Formula: C₃HCl₂F₅
• Molecular Weight: 202.94
• EINECS: 207-016-9
• Product Categories: refrigerants
• Mol File: 422-56-0.mol
• Article Data: 5

Chemical Properties

• Melting Point: -94°C
• Boiling Point: 51°C
• Flash Point: °C
• Appearance: /
• Density: 1.55
• Refractive Index: 1.3248
• CAS DataBase Reference: 3,3-Dichloro-1,1,1,2,2-pentafluoropropane(CAS DataBase Reference)
• NIST Chemistry Reference: 3,3-Dichloro-1,1,1,2,2-pentafluoropropane(422-56-0)
• EPA Substance Registry System: 3,3-Dichloro-1,1,1,2,2-pentafluoropropane(422-56-0)

Safety Data

• Hazard Codes: Xi
• Statements: 20/21/22-59
• Safety Statements: 23-36/37/39
• RIDADR: 3082
• Hazardous Substances Data: 422-56-0(Hazardous Substances Data)

Usage

General Description

Colorless odorless liquid. Nonflammable.

Air & Water Reactions

Slightly soluble in water.

Reactivity Profile

3,3-Dichloro-1,1,1,2,2-pentafluoropropane is chemically inert in many situations, but can react violently with strong reducing agents such as the very active metals and the active metals. They suffer oxidation with strong oxidizing agents and under extremes of temperature. Strong bases may release toxic gases.

InChI:InChI=1/C3HCl2F5/c4-1(5)2(6,7)3(8,9)10/h1H

Synthetic route

1,1,3-trichloro-2,2,3,3-tetrafluoropropane (422-54-8) → 3-chloro-1,1,1,2,2,3-hexafluoropropane (422-57-1) + 1-chloro-1,1,2,2,3,3-hexafluoropropane (422-55-9) + 3,3-dichloro-1,1,1,2,2-pentafluoropropane (422-56-0) + 1,3-dichloro-1,1,2,2,3-pentafluoropropane (507-55-1)

Conditions	Yield
With hydrogen fluoride; chromium(III) oxide at 280℃;	A 3% B 16% C 5% D 44%

Chlorodifluoromethane (75-45-6) + Chlorotrifluoroethylene (79-38-9) → 3,3-dichloro-1,1,1,2,2-pentafluoropropane (422-56-0) + 1,3-dichloro-1,1,2,2,3-pentafluoropropane (507-55-1) + 1,1,3-trichloro-2,2,3,3-tetrafluoropropane (422-54-8) + 1,1,2-trichloro-2,3,3,3-tetrafluoropropane (422-47-9)

Conditions	Yield
With aluminium trichloride at 0 - 10℃; for 10h; Further byproducts given;	A 0.6% B 12.4% C 30.5% D 12.5%

3-chloro-1,1,1,2,2-pentafluoropropane (422-02-6) → 3,3-dichloro-1,1,1,2,2-pentafluoropropane (422-56-0)

Conditions	Yield
With water; chlorine Irradiation.mit UV-Licht;

3-chloro-1,1,1,2,2-pentafluoropropane (422-02-6) → 3,3-dichloro-1,1,1,2,2-pentafluoropropane (422-56-0) + 1,1,1-trichloro-2,2,3,3,3-pentafluoropropane (4259-43-2)

Conditions	Yield
With chlorine at 250℃;

3-chloro-1,1,1,2,2-pentafluoro-3-iodo-propane (422-58-2) → 3,3-dichloro-1,1,1,2,2-pentafluoropropane (422-56-0)

Conditions	Yield
With chlorine Irradiation;

3-chloro-1,1,1,2,2-pentafluoro-3-iodo-propane (422-58-2) + chlorine (7782-50-5) → 3,3-dichloro-1,1,1,2,2-pentafluoropropane (422-56-0)

Conditions	Yield
im UV-Licht;

1,1,1-trichloro-2,2,3,3,3-pentafluoropropane (4259-43-2) → 3-chloro-1,1,1,2,2-pentafluoropropane (422-02-6) + 2,2,3-trichloro-1,1,1,3,3-pentafluoropropane (1599-41-3) + 2,3,3,3-tetrafluoro-propene (754-12-1) + 3,3-dichloro-1,1,1,2,2-pentafluoropropane (422-56-0) + perfluoropropyl chloride (422-86-6) + 1,1,1,2-tetrafluoropropane (421-48-7) + 1-chloro-1,1,2,2,3-pentafluoropropane (677-55-4) + C2F5CH=CClC2F5 + 3,4-dichlorodecafluorohex-3-ene (162763-52-2) + 1,1,1,2,2-pentafluoropropane (1814-88-6)

Conditions	Yield
With hydrogen fluoride; hydrogen; fluorided Pd on Al2O3 at 350℃; Product distribution / selectivity;

...Expand

1,1,1-trichloro-2,2,3,3,3-pentafluoropropane (4259-43-2) → 3-chloro-1,1,1,2,2-pentafluoropropane (422-02-6) + 2,2,3-trichloro-1,1,1,3,3-pentafluoropropane (1599-41-3) + 1,1,1-trifluoropropane (421-07-8) + 3,3-dichloro-1,1,1,2,2-pentafluoropropane (422-56-0) + perfluoropropyl chloride (422-86-6) + 1,1,1,2-tetrafluoropropane (421-48-7) + 1-chloro-1,1,2,2,3-pentafluoropropane (677-55-4) + 1,1,1,2,2-pentafluoropropane (1814-88-6)

Conditions	Yield
With hydrogen; fluorided platinum on aluminum oxide at 250℃; Product distribution / selectivity;

...Expand

1,1,1-trichloro-2,2,3,3,3-pentafluoropropane (4259-43-2) → 3-chloro-1,1,1,2,2-pentafluoropropane (422-02-6) + 2,2,3-trichloro-1,1,1,3,3-pentafluoropropane (1599-41-3) + 2,3,3,3-tetrafluoro-propene (754-12-1) + 3,3-dichloro-1,1,1,2,2-pentafluoropropane (422-56-0) + perfluoropropyl chloride (422-86-6) + 1-chloro-1,1,2,2,3-pentafluoropropane (677-55-4) + C2F5CH=CClC2F5 + 3,4-dichlorodecafluorohex-3-ene (162763-52-2) + 1,1,1,2,2-pentafluoropropane (1814-88-6)

Conditions	Yield
With hydrogen fluoride; hydrogen; fluorided Pd on Al2O3 at 350℃; Product distribution / selectivity;

...Expand

1,3-dichloro-1,1,2,2,3-pentafluoropropane (507-55-1) → 3,3-dichloro-1,1,1,2,2-pentafluoropropane (422-56-0) + 2,2-dichloro-1,1,1,3,3-pentafluoropropane (128903-21-9)

Conditions	Yield
aluminum (III) chloride; trichlorofluoromethane at 0 - 50℃; Product distribution / selectivity;

1,3-dichloro-1,1,2,2,3-pentafluoropropane (507-55-1) → 1-chloro-1,1,2,2,3,3-hexafluoropropane (422-55-9) + 3,3-dichloro-1,1,1,2,2-pentafluoropropane (422-56-0) + 1,1,2-trichloro-2,3,3,3-tetrafluoropropane (422-47-9) + 2,2-dichloro-1,1,1,3,3-pentafluoropropane (128903-21-9)

Conditions	Yield
partially fluorinated aluminum oxide at 300℃; for 10.0056h; Product distribution / selectivity; Inert atmosphere;

1,3-dichloro-1,1,2,2,3-pentafluoropropane (507-55-1) + 2,2-dichloro-1,1,1,3,3-pentafluoropropane (128903-21-9) → 1-chloro-1,1,2,2,3,3-hexafluoropropane (422-55-9) + 3,3-dichloro-1,1,1,2,2-pentafluoropropane (422-56-0) + 1,1,2-trichloro-2,3,3,3-tetrafluoropropane (422-47-9)

Conditions	Yield
partially fluorinated aluminum oxide at 300℃; for 10.0056h; Inert atmosphere;

1,3-dichloro-1,1,2,2,3-pentafluoropropane (507-55-1) + 2,2-dichloro-1,1,1,3,3-pentafluoropropane (128903-21-9) → 3,3-dichloro-1,1,1,2,2-pentafluoropropane (422-56-0)

Conditions	Yield
partially fluorinated aluminum oxide at 230℃; for 10.0056h; Product distribution / selectivity; Inert atmosphere;

1,3-dichloro-1,1,2,2,3-pentafluoropropane (507-55-1) → 3,3-dichloro-1,1,1,2,2-pentafluoropropane (422-56-0)

Conditions	Yield
With aluminum oxide at 250 - 400℃; for 4h; Reagent/catalyst; Inert atmosphere;

3,3-dichloro-1,1,1,2,2-pentafluoropropane (422-56-0) → 2,2,3,3,3-pentafluoropropionyl chloride (422-59-3)

Conditions	Yield
In chlorine	99%

4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane (5754-34-7) + 3,3-dichloro-1,1,1,2,2-pentafluoropropane (422-56-0) + 1,3-dichloro-1,1,2,2,3-pentafluoropropane (507-55-1) + perfluoro-2,5-dimethyl-3,6-dioxanonanoyl fluoride (2641-34-1) → C16H13O6F17

Conditions	Yield
With sodium fluoride at 20℃; for 20h;	67%

3,3-dichloro-1,1,1,2,2-pentafluoropropane (422-56-0) → 2,3,3,3-tetrafluoro-propene (754-12-1)

Conditions	Yield
With methane; oxygen; nickel at 675℃; under 1277.21 Torr; Product distribution / selectivity;	19%
With methylene chloride; oxygen; nickel at 675℃; under 1277.21 Torr; Product distribution / selectivity;	19%

3,3-dichloro-1,1,1,2,2-pentafluoropropane (422-56-0) + 1,3-dichloro-1,1,2,2,3-pentafluoropropane (507-55-1) → 1,1,1,2-tetrafluoropropane (421-48-7) + 1,1,1,2,2-pentafluoropropane (1814-88-6)

Conditions	Yield
With hydrogen; potassium acetate; palladium 10% on activated carbon In ethanol at 65℃; under 7757.43 Torr; for 16h; Product distribution / selectivity;

3,3-dichloro-1,1,1,2,2-pentafluoropropane (422-56-0) + 1,3-dichloro-1,1,2,2,3-pentafluoropropane (507-55-1) → 2,3,3,3-tetrafluoro-propene (754-12-1) + 1,1,1,2-tetrafluoropropane (421-48-7) + 1,1,1,2,2-pentafluoropropane (1814-88-6)

Conditions	Yield
With hydrogen; potassium acetate; palladium 10% on activated carbon In ethanol at 120℃; under 7757.43 Torr; for 16h; Product distribution / selectivity;

3,3-dichloro-1,1,1,2,2-pentafluoropropane (422-56-0) + 1,3-dichloro-1,1,2,2,3-pentafluoropropane (507-55-1) → 3-chloro-1,1,1,2,2-pentafluoropropane (422-02-6) + 2,3,3,3-tetrafluoro-propene (754-12-1)

Conditions	Yield
With hydrogen; potassium acetate; palladium 10% on activated carbon In ethanol at 40 - 45℃; under 7757.43 Torr; for 16h; Product distribution / selectivity;

3,3-dichloro-1,1,1,2,2-pentafluoropropane (422-56-0) + 1,3-dichloro-1,1,2,2,3-pentafluoropropane (507-55-1) → 3-chloro-1,1,1,2,2-pentafluoropropane (422-02-6) + 1,1,1,2,2-pentafluoropropane (1814-88-6)

Conditions	Yield
With ammonium formate; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 98 - 100℃; under 10343.2 Torr; for 22h; Product distribution / selectivity;
With hydrogen; 1% Pd/C at 80 - 145℃; under 760.051 - 1520.1 Torr; Product distribution / selectivity; Gas phase;

3,3-dichloro-1,1,1,2,2-pentafluoropropane (422-56-0) → 3-chloro-1,1,1,2,2-pentafluoropropane (422-02-6) + 2,3,3,3-tetrafluoro-propene (754-12-1) + 1,1,1,2,2-pentafluoropropane (1814-88-6)

Conditions	Yield
With hydrogen; acid treated activated carbon at 350 - 500℃; Product distribution / selectivity; Gas phase;

3,3-dichloro-1,1,1,2,2-pentafluoropropane (422-56-0) + 1,3-dichloro-1,1,2,2,3-pentafluoropropane (507-55-1) → 1,1-dichloro-1,2,2,3,3-pentafluoropropane (13474-88-9)

Conditions	Yield
With SbCl5; SbF3 In chloroform

3,3-dichloro-1,1,1,2,2-pentafluoropropane (422-56-0) + 1,3-dichloro-1,1,2,2,3-pentafluoropropane (507-55-1) → 3-chloro-1,1,1,2,2-pentafluoropropane (422-02-6) + 1,1,1-trifluoropropane (421-07-8) + 2,3,3,3-tetrafluoro-propene (754-12-1) + 1,1,1,2-tetrafluoropropane (421-48-7) + 1-chloro-1,1,2,2,3-pentafluoropropane (677-55-4) + 1,1,1,2,2-pentafluoropropane (1814-88-6) + 1,1,2,2,3-pentafluoropropane (679-86-7) + 1-chloro-1,2,2,3,3-pentafluoropropane (679-99-2)

Conditions	Yield
With hydrogen; fluorided Pd/Al2O3 at 300 - 350℃; Product distribution / selectivity;

...Expand

3-chloro-1,1,1,2,2-pentafluoropropane (422-02-6) + 3,3-dichloro-1,1,1,2,2-pentafluoropropane (422-56-0) → 1,1-dichloro-2,3,3,3-tetrafluoro-1-propene (2804-55-9) + cis-1,3-dichloro-1,2,3,3-tetrafluoro-1-propene (111512-50-6) + trans-1,3-dichloro-1,2,3,3-tetrafluoro-1-propene (111512-61-9)

Conditions	Yield
25weight percent chromium (III) chloride on carbon treated with HF at 300-425C at 350℃; under 760.051 Torr; for 0.00833333h;

3,3-dichloro-1,1,1,2,2-pentafluoropropane (422-56-0) → 1,1-dichloro-2,3,3,3-tetrafluoro-1-propene (2804-55-9)

Conditions	Yield
25weight percent chromium (III) chloride on carbon treated with HF at 300-425C at 350℃; under 760.051 Torr; for 0.00833333h;
With potassium hydroxide; tetrabutylammomium bromide In water at 0 - 45℃;
With potassium hydroxide; tetrabutylammomium bromide In water at 0 - 45℃; for 1h;

3,3-dichloro-1,1,1,2,2-pentafluoropropane (422-56-0) + 1-chloro-2,3,3,3-tetrafluoropropane (151771-09-4) → 2,3,3,3-tetrafluoro-propene (754-12-1) + 1,1-dichloro-2,3,3,3-tetrafluoro-1-propene (2804-55-9)

Conditions	Yield
With potassium hydroxide; tetrabutylammomium bromide In water at 0 - 10℃; for 20h; Product distribution / selectivity;

Upstream product

• 422-02-6 3-chloro-1,1,1,2,2-pentafluoropropane 
• 422-54-8 1,1,3-trichloro-2,2,3,3-tetrafluoropropane 
• 422-58-2 3-chloro-1,1,1,2,2-pentafluoro-3-iodo-propane 
• 7782-50-5 chlorine 
• 507-55-1 1,3-dichloro-1,1,2,2,3-pentafluoropropane 
• 128903-21-9 2,2-dichloro-1,1,1,3,3-pentafluoropropane 
• 4259-43-2 1,1,1-trichloro-2,2,3,3,3-pentafluoropropane 
• 75-45-6 Chlorodifluoromethane 
• 79-38-9 Chlorotrifluoroethylene 

Downstream Products

• 13474-88-9 1,1-dichloro-1,2,2,3,3-pentafluoropropane 
• 422-02-6 3-chloro-1,1,1,2,2-pentafluoropropane 
• 421-07-8 1,1,1-trifluoropropane 
• 754-12-1 2,3,3,3-tetrafluoro-propene 
• 421-48-7 1,1,1,2-tetrafluoropropane 
• 677-55-4 1-chloro-1,1,2,2,3-pentafluoropropane 
• 1814-88-6 1,1,1,2,2-pentafluoropropane 
• 679-86-7 1,1,2,2,3-pentafluoropropane 
• 679-99-2 1-chloro-1,2,2,3,3-pentafluoropropane 
• 422-59-3 2,2,3,3,3-pentafluoropropionyl chloride 

Relevant articles and documents

METHOD FOR ISOMERIZING ORGANIC COMPOUND, AND METHOD FOR PRODUCING ISOMER OF ORGANIC COMPOUND

A useful evaluation method which enables highly efficient production of a partially fluorinated alumina having good catalytic activities is discovered, and a method for isomerizing an organic compound whereby it becomes possible to improve a conversion rate in the desired isomerization reaction is provided. The method for isomerizing an organic compound comprises a step of selecting an alumina so that the acid amount calculated from the amount of ammonia desorbed at a desorption temperature of at least 300° C. by temperature-programmed desorption of ammonia is at least 0.10 mmol/g and at most 0.25 mmol/g; a step of fluorinating the selected alumina by a fluorinating agent to produce a partially fluorinated alumina; and a step of isomerizing, by using the obtained partially fluorinated alumina, an organic compound having at least two carbon atoms wherein to at least one of the adjacent carbon atoms, at least one fluorine atom is bonded and to the other, at least one chlorine atom or hydrogen atom is bonded.

METHOD FOR PRODUCING 1, 1-DICHLORO-2,2,3,3,3-PENTAFLUOROPROPANE

To provide a method for producing 1,1-dichloro-2,2,3,3,3-pentafluoropropane (HCFC-225ca) at a high content ratio, which is useful as e.g. a starting material to obtain 1,1-dichloro-2,3,3,3-tetrafluoropropene (R1214ya). The method comprises subjecting a starting material comprising one isomer or a mixture of at least two isomers of dichloropentafluoropropane (HCFC-225) and having a HCFC-225ca content of less than 60 mol%, to an isomerization reaction in the presence of a Lewis acid catalyst or a metal oxide catalyst so as to increase the HCFC-225ca content in the product to be higher than the content in the starting material.

19F nuclear magnetic resonance studies of halogenated propanes

The relationship between 19F chemical shifts in halogenated propanes and their structures are elucidated using MNDO calculations to determine the population of rotamers.The pairs of atom gauche to a fluorine atom and van der Waals interaction between the two terminal substituents are responsible for the 19F chemical shifts.The differences among chemical shifts in diastereomers are also discussed in terms of the conformation of molecule.