76-01-7

Basic information

• Product Name: Pentachloroethane
• Synonyms: Ethane,pentachloro- (8CI,9CI); 1,1,1,2,2-Pentachloroethane; Pentachloroethane;Pentalin
• CAS NO: 76-01-7
• Molecular Formula: C₂HCl₅
• Molecular Weight: 202.28
• EINECS: 200-925-1; Annex I Index No: 602-017-00-4

Usage

General Description

Pentachloroethane is a synthetic chemical compound that is used primarily as a solvent and as an intermediate in the production of other chemicals. It is a clear, colorless liquid with a strong, sweet smell. It is highly toxic and is a known carcinogen, meaning it has the potential to cause cancer. Exposure to pentachloroethane can occur through inhalation, ingestion, or skin contact, and can lead to symptoms such as headache, dizziness, nausea, and irritability. Long-term exposure may result in more serious health effects, including damage to the liver, kidneys, and nervous system. Due to its harmful effects on human health and the environment, the use of pentachloroethane has been restricted in many countries.

InChI:InChI=1/C2HCl5/c3-1(4)2(5,6)7/h1H

Synthetic route

Trichloroethylene (79-01-6) → pentachloroethane (76-01-7)

Conditions	Yield
With chlorine at 10 - 20℃; for 11h; Inert atmosphere; Cooling with ice;	99%
With tetrachloromethane; chlorine monoxide at -20℃;
With chlorine at 0℃; im Sonnenlicht;

N,N-Dichlorobenzenesulfonamide (473-29-0) + Trichloroethylene (79-01-6) → pentachloroethane (76-01-7) + N-(2,2,2-trichloroethylidene)benzenesulfonamide (55596-11-7)

Conditions	Yield
at 85 - 90℃; Product distribution; Other temperatures, UV irradiation, presence of azoisobutyronitrile or benzoyl peroxide.;	A n/a B 97%
at 85 - 90℃; Other temperatures, UV irradiation, presence of azoisobutyronitrile or benzoyl peroxide.;	A n/a B 97%

1,1,1-trichloroethane (71-55-6) → 1,1,1,2-tetrachoroethane (630-20-6) + 1,1-Dichloroethylene (75-35-4) + pentachloroethane (76-01-7)

Conditions	Yield
With chlorine at 25℃; Irradiation;	A 92.5% B 2.4% C 5.1%
With chlorine at 25℃; Irradiation;	A 89.9% B 4.7% C 5.3%

1,1-dichloroethane (75-34-3) → 1,1,1-trichloroethane (71-55-6) + 1,1,2-trichloroethane (79-00-5) + pentachloroethane (76-01-7)

Conditions	Yield
With chlorine at 200℃; for 0.05h; Mechanism; Irradiation; other temperature;	A 83.1% B 6.3% C 0.5%
With chlorine at 200℃; for 0.05h; Irradiation;	A 83.1% B 6.3% C 0.5%

N,N-Dichlorobenzenesulfonamide (473-29-0) + Trichloroethylene (79-01-6) → benzenesulfonamide (98-10-2) + pentachloroethane (76-01-7) + N-(2,2,2-trichloroethylidene)benzenesulfonamide (55596-11-7) + N-(2,2,2-trichloro-1-benzenesulfonamidoethyl)benzenesulfonamide (85095-84-7)

Conditions	Yield
With tin(IV) chloride at 20 - 22℃; for 1080h; Product distribution; other time, temperature, Lewis acid (AlCl3);	A n/a B n/a C n/a D 81%

1,1,2,2-tetrachloroethane (79-34-5) → 1,1,2,2-tetrachloroethylene (127-18-4) + Trichloroethylene (79-01-6) + pentachloroethane (76-01-7)

Conditions	Yield
With hydrogenchloride; oxygen at 379.84℃;	A 20.8% B 64.3% C 6.1%

Trichloroethylene (79-01-6) + N,N-dichloro-benzamide (22180-78-5) → pentachloroethane (76-01-7) + N-(2,2,2-trichloro-1-hydroxyethyl)benzamide (6316-07-0) + benzamide (55-21-0) + N-(dichloroacetyl)benzamide (97065-69-5)

Conditions	Yield
With air for 11h; Heating;	A n/a B n/a C n/a D 37%

Trichloroethylene (79-01-6) + N,N-dichlorotrifluoromethylsulfonamide (54285-45-9) → pentachloroethane (76-01-7) + 1,1,1-trichloro-2,2-bis(trifluoromethanesulfonylamino)ethane + 1,1,1-trifluoro-N-(2,2,2-trichloroethylidene)methanesulfonamide (434340-53-1)

Conditions	Yield
at 20℃; for 25h;	A n/a B n/a C 35%

(2,2-dichloro-vinyl)-trimethyl-silane (18163-67-2) → Trichloroethylene (79-01-6) + pentachloroethane (76-01-7) + Trimethyl-(1,2,2,2-tetrachloro-ethyl)-silane + Chloromethyl-dimethyl-(1,2,2,2-tetrachloro-ethyl)-silane

Conditions	Yield
With chlorine for 3h; Further byproducts given;	A 5% B 2% C 30% D 33%

Trichloroethylene (79-01-6) + N,N-dichloro-benzamide (22180-78-5) → pentachloroethane (76-01-7) + N-(2,2,2-trichloro-1-hydroxyethyl)benzamide (6316-07-0) + 1,1,1-trichloro-2,2-dibenzamidoethane (81637-90-3) + benzamide (55-21-0)

Conditions	Yield
at 85 - 90℃; for 10h;	A n/a B n/a C 28% D n/a

Trichloroethylene (79-01-6) + N,N-dichloro-acetamide (21824-73-7) → acetamide (60-35-5) + pentachloroethane (76-01-7) + N-(2,2,2-trichloro-1-hydroxyethyl)-acetamide (5445-85-2) + 2,2,2-trichloro-1,1-diacetamidoethane (57646-87-4)

Conditions	Yield
at 85 - 90℃; for 10h;	A n/a B n/a C n/a D 17%

Trichloroethylene (79-01-6) → 1,1,2,2-tetrachloroethylene (127-18-4) + pentachloroethane (76-01-7)

Conditions	Yield
With chlorine at 379.84℃; Reagent/catalyst; Temperature;	A 8.1% B 11.2%

Trichloroethylene (79-01-6) + N,N-dichloro-4-chlorobenzenesulfonamide (17260-65-0) → 4-Chlorobenzenesulfonamide (98-64-6) + pentachloroethane (76-01-7) + N-(2,2,2-trichloroethylidene)-4-chlorobenzenesulfonamide (81924-15-4) + N-(2,2,2-trichloro-1-p-chlorobenzenesulfonamidoethyl)-p-chlorobenzenesulfonamide (107905-40-8)

Conditions	Yield
With tin(IV) chloride at 20 - 22℃; for 720h; Product distribution; other time, temperature, Lewis acid (AlCl3);	A n/a B n/a C n/a D 7.1%

N,N-dichloro-p-toluenesulfonamide (473-34-7) + Trichloroethylene (79-01-6) → N-(2,2,2-trichloroethyliden)-p-toluenesulfonamide (51608-61-8, 13707-44-3) + pentachloroethane (76-01-7) + N-(2,2,2-trichloro-1-p-toluenesulfonamidoethyl)-p-toluenesulfonamide (93018-67-8) + toluene-4-sulfonamide (70-55-3)

Conditions	Yield
With tin(IV) chloride at 20 - 22℃; for 1560h; Product distribution; other time, temperature, Lewis acid (AlCl3);	A n/a B n/a C 2.7% D n/a

tetrachloromethane (56-23-5) → pentachloroethane (76-01-7)

Conditions	Yield
Einw. dunkler elektrischer Entladungen;

diethyl ether (60-29-7) + hexachloroethane (67-72-1) + ethylmagnesium bromide (925-90-6) → 1,1,2,2-tetrachloroethylene (127-18-4) + 1,1,1,2-tetrachoroethane (630-20-6) + pentachloroethane (76-01-7) + 1,1,2,2-tetrachloroethane (79-34-5)

diethyl ether (60-29-7) + hexachloroethane (67-72-1) + phenylmagnesium bromide → 1,1,2,2-tetrachloroethylene (127-18-4) + 1,1,1,2-tetrachoroethane (630-20-6) + pentachloroethane (76-01-7) + 1,1,2,2-tetrachloroethane (79-34-5)

chloroethane (75-00-3) → pentachloroethane (76-01-7)

Conditions	Yield
beim Chlorieren;

chloroform (67-66-3) → pentachloroethane (76-01-7)

Conditions	Yield
Einw. dunkler elektrischer Entladungen;
Brennen eines Lichtbogens (?);
In water at 25℃; Kinetics; sonolysis; sonication;

chloroform (67-66-3) → tetrachloromethane (56-23-5) + 1,1,2,2-tetrachloroethylene (127-18-4) + pentachloroethane (76-01-7) + 1,1,2,2-tetrachloroethane (79-34-5)

Conditions	Yield
beim Durchgang des elektrischen Lichtbogens; weitere Produkten: Hexachloraethan, Hexachlorbenzol, HCl und Kohle;

1,1,1-trichloroethane (71-55-6) → 1,1,1,2-tetrachoroethane (630-20-6) + pentachloroethane (76-01-7) + hexachloroethane (67-72-1)

Conditions	Yield
Chlorierung im Sonnenlicht;

bis (2-chloroethyl) sulphide (505-60-2) → pentachloroethane (76-01-7)

Conditions	Yield
With chlorine at 1001℃;

Trichloroethylene (79-01-6) → pentachloroethane (76-01-7) + 1,1,2,2-tetrachloro-1-nitroethane (39185-89-2)

Conditions	Yield
With nitrosylchloride

2-pentachloropropionyl-benzoic acid → phthalic anhydride (85-44-9) + pentachloroethane (76-01-7)

chloral (75-87-6) → 2,2,2-trichloro-4-trichloromethyl-2λ5-[1.3.2]dioxaphosphetane + pentachloroethane (76-01-7)

Conditions	Yield
With phosphorus pentachloride

chloral (75-87-6) → pentachloroethane (76-01-7)

Conditions	Yield
With phosphorus pentachloride
With aluminium trichloride

1,2-dichloro-ethane (107-06-2) → pentachloroethane (76-01-7)

Conditions	Yield
beim Chlorieren;

diethyl ether (60-29-7) + hexachloroethane (67-72-1) + para-methylphenylmagnesium bromide (4294-57-9) → 1,1,2,2-tetrachloroethylene (127-18-4) + 1,1,1,2-tetrachoroethane (630-20-6) + pentachloroethane (76-01-7) + 1,1,2,2-tetrachloroethane (79-34-5)

diethyl ether (60-29-7) + hexachloroethane (67-72-1) + 1-naphthylmagnesiumbromide (703-55-9) → 1,1,2,2-tetrachloroethylene (127-18-4) + 1,1,1,2-tetrachoroethane (630-20-6) + pentachloroethane (76-01-7) + 1,1,2,2-tetrachloroethane (79-34-5)

1,1,2,2-tetrachloroethane (79-34-5) → pentachloroethane (76-01-7)

Conditions	Yield
With pumice stone at 700℃;
With chlorine Irradiation.UV-Licht;
With hydrogenchloride; oxygen at 349.84℃; Reagent/catalyst; Temperature;

pentachloroethane (76-01-7) → 1,1,2,2-tetrachloroethylene (127-18-4)

Conditions	Yield
With methyl diethylphosphinate at 150℃; for 10h;	75%
With chlorine at 379.84℃; Gas phase; chemoselective reaction;	33.8%
With nickel dichloride at 330℃;

pentachloroethane (76-01-7) + bis[(O-trimethylsilyl-N-diphenylphosphinimino)-4-(t-butyl)benzohydrazide]ethane → bis[N-(diphenylphosphiniminoethane)-4-t-butyl-phenyl-N',O](dichloromethyl)siliconium chloride

Conditions	Yield
In chloroform at 20℃; for 0.833333h;	46%

pentachloroethane (76-01-7) + benzaldehyde (100-52-7) → 2,2,3,3,3-pentachloro-1-phenyl-propanol (833-26-1)

Conditions	Yield
With iodobenzene; tetrabutylammonium tetrafluoroborate In N,N-dimethyl-formamide for 5.6h; Ambient temperature; electrolysis; Cd-coated cathode, Mg anode;	45%

pentachloroethane (76-01-7) → Trichloroethylene (79-01-6) + 1,1,2,2-tetrachloroethane (79-34-5)

Conditions	Yield
With hexacarbonyl molybdenum at 140℃; for 3h; further reagent Fe(CO)5;	A 42% B 23%
With iron pentacarbonyl at 140℃; for 3h; further reagent Mo(CO)6;	A 27% B 23%

pentachloroethane (76-01-7) + Diethyl allylphosphonate (1067-87-4) → (2,4,4,5,5-Pentachloro-pentyl)-phosphonic acid diethyl ester

Conditions	Yield
With 2-hydroxy-2-phenylacetophenone; iron(III) chloride In acetonitrile at 130℃;	40%

pentachloroethane (76-01-7) → phosgene (75-44-5) + Trichloroacetyl chloride (76-02-8)

Conditions	Yield
Irradiation (UV/VIS); with Cl2 sensibilized photochemical oxidn., 80 to 100°C;	A 20% B n/a

piperidine (110-89-4) + tetrachloromethane (56-23-5) + pentachloroethane (76-01-7) → 1,1,2,2-tetrachloroethylene (127-18-4)

Conditions	Yield
at 20℃;

1,2-Dichloroethylene (540-59-0) + pentachloroethane (76-01-7) → 1,1,2,3,4-pentachloro-butane (77753-24-3)

Conditions	Yield
With aluminium trichloride at 40℃; 1,1,2,3,4-pentachloro-butane, solid form;
With aluminium trichloride at 40℃; 1,1,2,3,4-pentachloro-butane, liquid form;

1,2-Dichloroethylene (540-59-0) + pentachloroethane (76-01-7) → 1,1,2,2,3,4,4-heptachloro-butane (34973-41-6)

Conditions	Yield
With aluminium trichloride at 40℃;

chloroform (67-66-3) + pentachloroethane (76-01-7) → 1,1,1,2,2,3,3-heptachloropropane (594-89-8)

Conditions	Yield
With aluminium trichloride

Upstream product

• 56-23-5 tetrachloromethane 
• 60-29-7 diethyl ether 
• 67-72-1 hexachloroethane 
• 703-55-9 1-naphthylmagnesiumbromide 
• 79-34-5 1,1,2,2-tetrachloroethane 
• 473-34-7 N,N-dichloro-p-toluenesulfonamide 
• 79-01-6 Trichloroethylene 
• 473-29-0 N,N-Dichlorobenzenesulfonamide 
• 156-60-5 trans-1,2-dichloroethylene 
• 75-34-3 1,1-dichloroethane 
• 71-55-6 1,1,1-trichloroethane 
• 354-21-2 1,1,2-trichloro-2,2-difluoroethane 
• 21824-73-7 N,N-dichloro-acetamide 
• 13698-16-3 ethyl N,N-dichlorocarbamate 

Downstream Products

• 120-12-7 anthracene 
• 519-73-3 triphenylmethane 
• 34867-75-9 1,1',2,2',6-Pentachlor-n-hexan 
• 34867-74-8 1,1,2,2,4-pentachlorobutane 
• 34867-78-2 1,1',2,2',4,6,6'-Heptachlor-n-hexan 
• 127-18-4 1,1,2,2-tetrachloroethylene 
• 67-72-1 hexachloroethane 
• 55453-82-2 1,1,2-Trichlorethanphosphonsaeuredichlorid 
• 55453-83-3 1,1,2,2-tetrachlorethanphosphonsaeuredichlorid 
• 79-34-5 1,1,2,2-tetrachloroethane 
• 79-01-6 Trichloroethylene 
• 67-63-0 isopropyl alcohol 
• 75-44-5 phosgene 
• 3170-80-7 trichloromethyl radical 

Relevant articles and documents

Photocatalytic degradation of gaseous trichloroethylene on porous titanium dioxide pellets modified with copper(II) under visible light irradiation

Porous titanium dioxide pellets modified with copper(II) ion (Cu-TiO2) were synthesized by sol-gel method with dialysis for photocatalytic degradation of gaseous trichloroethylene (TCE) under visible light (VL) irradiation. TCE was completely degraded by passing the gas stream (mole fractions of oxygen and TCE were 0.2 and 1.75 × 10?4, respectively) at the flow rate of 25 mL min?1 through 0.2 g of the Cu-TiO2 pellets (Cu content: 0.1 atom%) calcined at 200 °C. TCE was converted mainly to carbon dioxide, dichloroacetic acid (DCAA), and inorganic chlorine species. Relatively small quantities of pentachloroethane (PCA) and trichloroacetaldehyde (TCAH) were detected as products on the Cu-TiO2 surface. Comparison with porous TiO2 pellets under ultraviolet irradiation revealed that more chlorinated products and less carbon dioxide were formed on Cu-TiO2 under VL irradiation. The mineralization of TCE to carbon dioxide was calculated to be only ca. 30.0%. It is noted that DCAA, PCA and TCAH were accumulated on the surface and were extracted with ethyl acetate. The porous Cu-TiO2 pellets show promise as the photocatalyst acting under VL irradiation for converting TCE gas to chlorinated compounds which can be used in industries.

Method for comprehensive utilization of hexachloroethane

The invention relates to a comprehensive utilization method of a dichloroethane chlorination byproduct namely hexachloroethane. The comprehensive utilization method comprises the following steps: adding a hexachloroethane solution, glycerin, a hydrogenation catalyst and a chlorination catalyst into a high-pressure kettle; after feeding is finished, performing hydrodechlorination and glycerin chlorination reaction at the same time at certain temperature and under certain hydrogen pressure; after reaction is finished, maintaining the temperature for 4h, and then reducing the temperature to the room temperature; performing filtering separation to obtain the hydrogenation catalyst, layering reaction liquid to obtain a solvent layer and a glycerin layer, wherein the solvent layer contains a solvent, pentachloroethane, pentachloroethane and trichloroethane, and the glycerin layer contains the glycerin, dichloropropanol, water, the chlorination catalyst and monochlorohydrin.