10436-39-2

Basic information

• Product Name: Tetrachloropropene
• Synonyms: Tetrachloropropene;1,1,2,3-Tetrachloropropene;1,1,2,3-tetrachloro-1-propen;1,1,2,3-tetrachloro-1-propene;1,1,2,3-tetrachloro-propen;2,3,3-trichloroallyl chloride;1,1,2,3-Tetrachloroprop-1-ene
• CAS NO: 10436-39-2
• Molecular Formula: C₃H₂Cl₄
• Molecular Weight: 179.85998
• EINECS: 233-920-8
• Mol File: 10436-39-2.mol
• Article Data: 27

Chemical Properties

• Boiling Point: 141.38°C (rough estimate)
• Flash Point: 62.3°C
• Appearance: /
• Density: 1.5500
• Vapor Pressure: 1.66mmHg at 25°C
• Refractive Index: 1.5121 (estimate)
• Storage Temp.: Refrigerator
• Solubility: Chloroform, Methanol (Slightly)
• CAS DataBase Reference: Tetrachloropropene(CAS DataBase Reference)
• NIST Chemistry Reference: Tetrachloropropene(10436-39-2)
• EPA Substance Registry System: Tetrachloropropene(10436-39-2)

Safety Data

• Hazardous Substances Data: 10436-39-2(Hazardous Substances Data)

Usage

Uses

1,1,2,3-Tetrachloropropene is used in producing 2,3,3,3-Tetrachloropropene. 2,3,3,3-Tetrachloropropene may be useful as heat transfer compns., aerosol propellants, foaming agents, blowing agents, solvents, cleaning agents, carrier fluids, displacement drying agents, buffing abrasion agents, polymn.

InChI:InChI=1/C3H2Cl4/c4-1-2(5)3(6)7/h1H2

Synthetic route

1,1,2,2,3-pentachloropropane (16714-68-4) → 1,1,2,3-Tetrachloropropene (10436-39-2)

Conditions	Yield
With sodium hydroxide; cetylpyridinium bromide at 130℃; for 2h;	97%
With potassium hydroxide
With sodium hydroxide

1,1,1,2,2,3-hexachloropropane (24425-97-6) → 1,1,2,3-Tetrachloropropene (10436-39-2)

Conditions	Yield
With hydrogenchloride; zinc In 1,4-dioxane; water at 45℃; for 49h; Autoclave; Inert atmosphere;	90%

1,1,1,3-tetrachloropropane (1070-78-6) → 1,1,1,2,3-pentachloro-propane (21700-31-2) + 3,3-dichloroallyl chloride (2567-14-8) + 1,1,2,3-Tetrachloropropene (10436-39-2)

Conditions	Yield
With iron(III) chloride; chlorine at 82℃; under 1277.21 Torr; for 15.33h; Product distribution / selectivity;	A 82.9% B 3.4% C 8.1%

1,1,1,2,3-pentachloro-propane (21700-31-2) → 1,1,2,3-Tetrachloropropene (10436-39-2) + 2,3,3,3-tetrachloropropene (16500-91-7)

Conditions	Yield
With potassium hydroxide at 0℃;
With potassium hydroxide; Aliquat 336 In water at 80℃; for 3h;
With potassium hydroxide; Aliquat 336 In water at 80℃; for 3h;
With potassium hydroxide; Aliquat 336 In water at 8℃; for 3h;

2,3,3,3-tetrachloropropene (16500-91-7) → 1,1,2,3-Tetrachloropropene (10436-39-2)

Conditions	Yield
at 180℃;
With aluminium trichloride at 0℃;
With antimonypentachloride
at 150 - 180℃;

methanol (67-56-1) + 2,3,3-trichloro-2-propen-1-ol (3266-39-5) → methyl 2-chloroacrylate (80-63-7) + 1,1,2,3-Tetrachloropropene (10436-39-2)

Conditions	Yield
With sulfuric acid; water 1) 105 deg C, 4 h, 2) 30 min; Yield given. Multistep reaction. Yields of byproduct given;

1,1,1,2,3-pentachloro-propane (21700-31-2) → 3,3,3-trichloro-1-propene (2233-00-3) + 1,1,2,3-Tetrachloropropene (10436-39-2)

Conditions	Yield
at 400℃; under 750.075 Torr; for 0.0130556h; Inert atmosphere;

1,1,1,2,3-pentachloro-propane (21700-31-2) → 2,3-dichloro-3,3-difluoroprop-1-ene (2252-87-1) + 1,1,2,3-Tetrachloropropene (10436-39-2) + 1,1,2,3-tetrachloro-1-fluoro-propane (666-27-3)

Conditions	Yield
With hydrogen fluoride at 290℃; under 750.075 Torr; for 3h; Inert atmosphere; tubular reactor;

prop-1-yne (74-99-7) → 1,1,2,3-Tetrachloropropene (10436-39-2) + 2,3,3,3-tetrachloropropene (16500-91-7)

Conditions	Yield
Stage #1: prop-1-yne With chlorine at 60 - 80℃; Stage #2: With chlorine; dibenzoyl peroxide at 40 - 50℃; Stage #3: With sodium hydroxide at 40 - 50℃;

chloroform (67-66-3) + 1,1-Dichloroethylene (75-35-4) → 1,1,2,3-Tetrachloropropene (10436-39-2)

Conditions	Yield
at 100 - 450℃; under 1018.63 Torr; Temperature; Reagent/catalyst; Pressure; Inert atmosphere;	8.1 %Spectr.

1,1,1,2,3-pentachloro-propane (21700-31-2) → 2-chloro-1,1,1-trifluoropropene (2730-62-3) + 1,1,1-trifluoropropylene (677-21-4) + 1,1,2,3-Tetrachloropropene (10436-39-2) + 2,3,3,3-tetrachloropropene (16500-91-7) + 2,3,3-trichloro-3-fluoro-propene (421-42-1)

Conditions	Yield
With hydrogen fluoride at 350℃; under 750.075 Torr; Temperature;	A 77 %Chromat. B 11 %Chromat. C 42.7 %Spectr. D 22.3 %Spectr. E 6.6 %Spectr.

1,1,1,2,3-pentachloro-propane (21700-31-2) → 2-chloro-1,1,1-trifluoropropene (2730-62-3) + 1,1,1-trifluoropropylene (677-21-4) + 1,1,2,3-Tetrachloropropene (10436-39-2) + 2,3,3-trichloro-3-fluoro-propene (421-42-1) + 1,1,2,3-tetrachloro-1-fluoro-propane (666-27-3)

Conditions	Yield
With hydrogen fluoride at 275℃; under 750.075 Torr;	A 80 %Chromat. B 13 %Chromat. C 53.3 %Spectr. D 6.9 %Spectr. E 6.9 %Spectr.

1,1,2,3-Tetrachloropropene (10436-39-2) + hexamethylenetetramine (100-97-0) → N-β,γ,γ-trichloroallylhexamethylenetetramine chloride

Conditions	Yield
In chloroform at 60℃; for 12h;	99.6%

piperazine (110-85-0) + 1,1,2,3-Tetrachloropropene (10436-39-2) → N,N'-bis(1,2,2-trichloroallyl)piperazine (137554-28-0)

Conditions	Yield
In isopropyl alcohol at 90 - 95℃; for 4h;	86.8%

1,3-dioxolane-4-methanol (5464-28-8) + 1,1,2,3-Tetrachloropropene (10436-39-2) → 4-(2,3,3-Trichloro-allyloxymethyl)-[1,3]dioxolane (127719-54-4)

Conditions	Yield
With potassium hydroxide; 18-crown-6 ether for 4h; Ambient temperature;	80%

1,1,2,3-Tetrachloropropene (10436-39-2) + dithiobenzoic acid triethylammonium salt (42967-74-8) → dithiobenzoic acid β,γ,γ-trichloroallyl ester (154424-51-8)

Conditions	Yield
In acetone	78%

1,1,2,3-Tetrachloropropene (10436-39-2) → 2-chloro-1,1,1-trifluoropropene (2730-62-3)

Conditions	Yield
With hydrogen fluoride; antimonypentachloride; chlorine; 1-ethyl-3-methyl-1H-imidazol-3-ium chloride In 1,1,2-trichloro-2,2-difluoroethane at 132.1℃; under 6000.6 Torr; Product distribution / selectivity;	72.6%
With hydrogen fluoride; diisopropylamine; chromium(III) oxide at 200 - 300℃; under 760.051 Torr; for 0.000569444 - 0.00277778h; Product distribution / selectivity;
With methoxyhydroquinone; hydrogen fluoride; chromium(III) oxide at 243 - 254℃; under 760.051 Torr; for 66.75h; Product distribution / selectivity;

aminoethylpiperazine (140-31-8) + 1,1,2,3-Tetrachloropropene (10436-39-2) → N-(1,1,2-trichloroallyl)-N'-(β-1,2,2-trichloroallylaminoethyl)piperazine (137554-29-1)

Conditions	Yield
In isopropyl alcohol Heating;	70%

1,1,2,3-Tetrachloropropene (10436-39-2) + sodium thiophenolate (930-69-8) → phenyl-(2,3,3-trichloro-allyl)-sulfide (38491-40-6)

Conditions	Yield
In N,N-dimethyl-formamide	70%

1,1,2,3-Tetrachloropropene (10436-39-2) + 1,5-diamino-3-azapentane (111-40-0) → N,N'-bis(1,2,3-trichloroallyl)diethylenetriamine (137554-22-4)

Conditions	Yield
In isopropyl alcohol Heating;	65%

1,1,2,3-Tetrachloropropene (10436-39-2) → 1,1,1,2,3-pentafluoropropane (431-31-2)

Conditions	Yield
With hydrogen fluoride; antimonypentachloride at 150℃; under 47821.8 Torr; for 8h; Product distribution / selectivity;	59%

1,1,2,3-Tetrachloropropene (10436-39-2) → 2-chloro-1,1,1-trifluoropropene (2730-62-3) + 2-chloro-1,1,1,2-tetrafluoropropane (421-73-8) + 1,1,1,2,3-pentafluoropropane (431-31-2) + 2,3-dichloro-1,1,1-trifluoropropane (338-75-0) + 1-chloro-2,3,3,3-tetrafluoropropane (151771-09-4) + 2-chloro-1,1,1,3-tetrafluoropropane (117970-90-8)

Conditions	Yield
With hydrogen fluoride; antimonypentachloride at 100 - 125℃; under 33082.7 - 39185.2 Torr; for 12h; Product distribution / selectivity;	A n/a B n/a C 53% D n/a E n/a F n/a

p-cresol (106-44-5) + 1,1,2,3-Tetrachloropropene (10436-39-2) → 4-methyl-2-(2,3,3-trichloro-2-propenyl)phenol (106119-06-6)

Conditions	Yield
	31%

1,1,2,3-Tetrachloropropene (10436-39-2) → 2-chloro-1,1,1-trifluoropropene (2730-62-3) + 2-chloro-2,3,3-trifluoro-butane (374-06-1)

Conditions	Yield
With hydrogen fluoride; antimonypentachloride; chlorine; 1-ethyl-3-methyl-1H-imidazol-3-ium chloride In 1,1,2-trichloro-2,2-difluoroethane at 133.2℃; under 6000.6 Torr; Product distribution / selectivity;	A 25.5% B 6.6%

1,1,2,3-Tetrachloropropene (10436-39-2) + sodium methylate (124-41-4) → methyl-(2,3,3-trichloro-allyl)-ether (63578-64-3)

Conditions	Yield
With methanol

1,1,2,3-Tetrachloropropene (10436-39-2) → tetrachloromethane (56-23-5) + hexachloroethane (67-72-1)

Conditions	Yield
With chlorine at 400℃; under 36775.4 Torr;

1,1,2,3-Tetrachloropropene (10436-39-2) → 3-bromo-1,1,2-trichloro-propene (6066-14-4)

Conditions	Yield
With acetone; sodium bromide
With hydrogen bromide; iron(III) chloride

1,1,2,3-Tetrachloropropene (10436-39-2) → 1,1,2-trichloropropene (21400-25-9)

Conditions	Yield
With tetrahydrofuran; lithium aluminium tetrahydride
With ethanol; zinc

1,1,2,3-Tetrachloropropene (10436-39-2) → 1,1,1,2,2,3-hexachloropropane (24425-97-6)

Conditions	Yield
With chlorine Irradiation.mit UV-Licht;

1,1,2,3-Tetrachloropropene (10436-39-2) → 2,3,3-trichloro-2-propen-1-ol (3266-39-5)

Conditions	Yield
With sodium carbonate

1,1,2,3-Tetrachloropropene (10436-39-2) → 1,1,2-trichloro-3-phenyl-propene (17078-21-6)

Conditions	Yield
With aluminium trichloride; benzene

1,1,2,3-Tetrachloropropene (10436-39-2) + diethylamine (109-89-7) → diethyl-(2,3,3-trichloro-allyl)-amine (118378-57-7)

Conditions	Yield
With methanol

morpholine (110-91-8) + 1,1,2,3-Tetrachloropropene (10436-39-2) → 4-(2,3,3-trichloro-allyl)-morpholine (15111-02-1)

Conditions	Yield
In methanol Heating;

1,1,2,3-Tetrachloropropene (10436-39-2) + sodium ethanolate (141-52-6) → 1,1,2-trichloro-3-ethoxy-propene (15111-07-6)

Conditions	Yield
With phenol In ethanol

1,1,2,3-Tetrachloropropene (10436-39-2) + sodium thiocyanide (540-72-7) → 2,3,3-Trichlor-allyl-thiocyanat (3266-21-5)

Conditions	Yield
In ethanol

1,1,2,3-Tetrachloropropene (10436-39-2) + sodium diethylmalonate (996-82-7) → Bis(β.γ.γ-trichlorallylmalonic Acid)-Diethyl Ester (31000-94-9)

Conditions	Yield
In ethanol

1,1,2,3-Tetrachloropropene (10436-39-2) + sodium diethylmalonate (996-82-7) → β.γ.γ-Trichlorallylmalonic Acid-Diethyl Ester (31000-93-8)

Conditions	Yield
In ethanol

Upstream product

• 1600-37-9 1,1,2,3,3-pentachloro-1-propene 
• 1888-71-7 perchloropropene 
• 1070-78-6 1,1,1,3-tetrachloropropane 
• 21700-31-2 1,1,1,2,3-pentachloro-propane 
• 74-99-7 prop-1-yne 
• 24425-97-6 1,1,1,2,2,3-hexachloropropane 
• 16714-68-4 1,1,2,2,3-pentachloropropane 
• 67-66-3 chloroform 
• 75-35-4 1,1-Dichloroethylene 
• 127-18-4 1,1,2,2-tetrachloroethylene 
• 74-87-3 methylene chloride 
• 16500-91-7 2,3,3,3-tetrachloropropene 
• 10035-10-6 hydrogen bromide 
• 94-36-0 dibenzoyl peroxide 

Downstream Products

• 17078-22-7 1,1,2-Trichlor-3-(2,4,6-trimethyl-phenyl)-propen 
• 17078-21-6 1,1,2-trichloro-3-phenyl-propene 
• 2730-62-3 2-chloro-1,1,1-trifluoropropene 
• 2252-87-1 2,3-dichloro-3,3-difluoroprop-1-ene 
• 374-06-1 2-chloro-2,3,3-trifluoro-butane 
• 421-73-8 2-chloro-1,1,1,2-tetrafluoropropane 
• 431-31-2 1,1,1,2,3-pentafluoropropane 
• 338-75-0 2,3-dichloro-1,1,1-trifluoropropane 
• 151771-09-4 1-chloro-2,3,3,3-tetrafluoropropane 
• 117970-90-8 2-chloro-1,3,3,3-tetrafluoropropane 
• 754-12-1 2,3,3,3-tetrafluoro-propene 
• 1814-88-6 1,1,1,2,2-pentafluoropropane 
• 431-27-6 1,2-dichloro-3,3,3-trifluoropropene 
• 154424-51-8 dithiobenzoic acid β,γ,γ-trichloroallyl ester 

Relevant articles and documents

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PROCESSES FOR PREPARING PENTACHLOROPROPANE AND TETRACHLOROPROPENE FROM DICHLOROPROPENE

A processes for preparing 1,1,2,3-tetrachloropropene, 2,3,3,3-tetrachloropropene, or a mixture thereof from 1,3-dichloropropene. The process may include a two successive chlorination and dehydrochlorination reactions. In a first chlorination reaction 1,3-dichloropropene is reacted with a chlorination agent to form a first chlorination reaction product including 1,1,2,3-tetrachloropropane. This first chlorination reaction product is reacted with a dehydrochlorination reagent in a first dehydrochlorination reaction to form a first dehydrochlorination reaction product including a trichloropropene. The trichloropropene containing reaction product is reacted with a chlorination agent in a second chlorination reaction to form a second chlorination reaction product including at least one of 1,1,1,2,3-pentachloropropane or 1,1,2,2,3-pentachloropropane. This reaction product is reacted with a dehydrochlorination reagent in a second dehydrochlorination reaction to form a second dehydrochlorination reaction product having 1,1,2,3-tetrachloropropene or a 2,3,3,3-tetrachloropropene.

METHOD FOR PRODUCING 2-CHLORO-3,3,3-TRIFLUOROPROPENE

The invention relates to a method for producing 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf) from at least one compound A selected from the group consisting of halopropane of formulae CX3CHClCH2X or CX3CFClCH3, or halopropenes of formula CQX2CCNCH2 and CX2═CClCH2X where X independently represents a fluorine or chlorine atom, characterised in that it comprises bringing said at least one compound A into contact with HF in a gaseous phase in the presence of a fluorination catalyst AlF3 or fluorine-bearing alumina in order to form a gaseous flow B comprising 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf) et 3,3,3-trifluoropropene (HFO-1243zf).

Preparation method of 1,1,2,3-tetrachloropropene

The invention discloses a preparation method of 1,1,2,3-tetrachloropropene. The method comprises the steps of (1) reacting trichloromethane, 1,2-dichloroethylene and a first catalyst, cooling to room temperature after reaction is completed, adding water, carrying out vacuum rectification to obtain 1,1,2,3,3-pentachloropropane; (2) carrying out gas-phase catalytic dehydrochlorination reaction on the 1,1,2,3,3-pentachloropropane under the action of a second catalyst to obtain 1,2,3,3-tetrachloropropene; (3) carrying out gas-phase catalytic addition reaction on hydrogen chloride and the 1,2,3,3-tetrachloropropene under the action of a third catalyst to obtain 1,1,2,2,3-pentachloropropane; and (4) carrying out gas-phase catalytic dehydrochlorination reaction on the 1,1,2,2,3-pentachloropropane under the action of a fourth catalyst, collecting a reaction product and carrying out vacuum rectification to obtain the 1,1,2,3-tetrachloropropene. The preparation method is simple in process, available in raw materials, low in cost, high in yield, green and environment-friendly and is especially suitable for industrial production.