75-00-3 Usage
Overview
Chloroethane (also known as ethyl chloride) is a chemical compound with chemical formula C2H5Cl, and has been widely used in producing tetraethyllead, a gasoline additive. It is a colorless, flammable gas or refrigerated liquid with a faintly sweet odor.
Ethyl chloride is used in the production of ethyl cellulose, use as a solvent, refrigerant, and topical anesthetic, in the manufacture of dyes, chemicals, and pharmaceuticals, and as a medication to alleviate pain associated with insect burns and stings.[1]
In the past, ethyl chloride was used in the production of tetraethyl lead, an anti-knock additive to leaded gasoline. Government-mandated reduction in the amount of lead additives used in gasoline in the United States and a shift to the use of unleaded gasoline has caused a drastic reduction in the amount of ethyl chloride required for the production of tetraethyl lead.[1]
Chemical Properties
Different sources of media describe the Chemical Properties of 75-00-3 differently. You can refer to the following data:
1. Ethyl chloride is a colorless gas with an ethereal odor[1,6]. Ethyl chloride has an odor threshold of 4.2 parts per million (ppm)[7]. Ethyl chloride is slightly soluble in water[1].
The chemical formula for ethyl chloride is C2H5Cl, and it has a molecular weight of 64.52 g/mol[1,3]. The vapor pressure for ethyl chloride is 1,008 mm Hg at 20°C, and the log octanol/water partition; coefficient (log Kow) is 1.43; coefficient (log Kow) is 1.43.[1]
2. colourless gas
3. Ethyl chloride is a colorless gas or liquid
(below 12℃) with a pungent, ethereal odor and a burning
taste. Shipped as a liquefied compressed gas.
Production
The dominant process for production of ethyl chloride in the USA involves the addition of anhydrous hydrogen chloride to ethylene in the presence of an aluminium chloride catalyst. The hydrochlorination is a liquidphase reaction, carried out at about 40°C. Reacted products are fed into a flash evaporator column, where ethyl chloride is separated from less volatile compounds and then purified by fractionation. Hydrochlorination of ethanol has not been used for US ethyl chloride production since 1980, and chlorination of ethane (catalytically, electrolytically, thermallyor photochemically) has not been used at any production facility in the USA since 1974. Ethyl chloride is also obtained as a by-product from the production of vinyl chloride[1] or chlorofluorocarbon, although this method accounts for only a small amount.
Application
Ethyl chloride is used in the manufacture of tetraethyllead and as an alkylating agent in the production of ethylcellulose (which is used in paper coatings, printing inks, films, adhesives and moulded plastics), ethylhydroxyethylcellulose, and some pharmaceuticals and as a foam-blowing agent in the manufacture of polystyrene. It is used as a local anaesthetic because of its rapid cooling effect as it vaporizes[1]. Historical and minor uses Include use in organic synthesis, as an alkylating agent in the production of aluminium alkyls and other metal alkyls and as a solvent for phosphorus, sulfur, fats, oils, resins and waxes.
Source and exposure
Sources of possible ethyl chloride exposure include the inhalation of contaminated air and ingestion of contaminated drinking water at very low levels. The general population can be exposed to ethyl chloride by skin contact with consumer products that contain ethyl chloride such as solvents and refrigerants. Occupational exposure by inhalation or dermal contact with ethyl chloride can occur in industries such as medical and health services; automotive dealers and service stations; wholesale trade, electric, gas, and sanitary services; machinery (except electrical) and special trade contractors; fabricated metal productions; printing and publishing; painting; rubber and plastic products; and food.[1]?Although chemists use tests such as gas chromatography to measure ethyl chloride in blood, milk, or urine, no commonly used medical tests are available to determine whether or not a person has been exposed to ethyl chloride.[1]
Toxicity
Acute Effects
Acute inhalation exposure to high levels of ethyl chloride in humans has resulted in temporary feelings of drunkenness, dizziness, lack of muscle coordination and unconsciousness. Accidental death has resulted from its former medical use as an anesthetic during major surgery.[1,2] Tests involving acute exposure of animals in rats and mice have shown ethyl chloride to have low toxicity from inhalation exposure.[3]
Chronic Effects
Neurological symptoms including ataxia, tremors, speech difficulties, slowed reflexes, involuntary eye movement, and hallucinations, and liver effects were reported in individuals who purposely inhaled very high concentrations of ethyl chloride for a few months.[4]
Some animal studies indicate effects on the lungs, liver, kidneys, and heart due to ethyl chloride exposure via inhalation.[1] The Reference Concentration (RFC) for ethyl chloride is 10 milligrams per cubic meter (mg/m3) based on delayed fetal ossification in mice. The RFC is an estimate (with uncertainty spanning perhaps an order of magnitude) of a continuous inhalation exposure to the human population (including sensitive subgroups), which is likely to be without appreciable risk of deleterious noncancer effects during a lifetime. It is not a direct esimator of risk but rather a reference point to gauge the potential effects. At exposures increasingly greater than the RFC, the potential for adverse health effects increases. Lifetime exposure above the RFC does not imply that an adverse health effect would necessarily occur.[4]
EPA has medium confidence in the study on which the RFC is based because, although the study is well conducted, it does not establish a firm concentration-response relationship with an adverse effect and was not performed at levels eliciting maternal toxicity; medium confidence in the database due to the lack of a multigenerational reproductive study and a developmental study in a second species; and, consequently, medium confidence in the RFC.[4]?EPA has not established a Reference Dose (RfD) for ethyl chloride.[4] Reproductive/Developmental Effects
No studies were located regarding reproductive or developmental effects following ethyl chloride inhalation exposure in humans.
Several animal studies found no reproductive effects caused by ethyl chloride exposure. An animal study reported a decrease in uterine weights, while another study reported minimal evidence of fetotoxicity (increase in centers of unossified bones of the skull) from inhalation exposure to ethyl chloride.[1]
Cancer Risk
There are no human cancer data available for ethyl chloride. A 2-year bioassay performed by the NTP indicated that inhaled ethyl chloride is carcinogenic in female mice and may be carcinogenic in rats. Female mice experienced a significant increase in the incidence of uterine tumors and hepatocellular tumors, but the data on male mice were considered inadequate because of a low survival rate. Benign and malignant epithelial neoplasms of the skin, and three uncommon malignant astorcyomas of the brain, were reported in male and female rats, respectively.[5] EPA has not classified ethyl chloride for carcinogenicity.[4]
References
Agency for Toxic Substances and Disease Registry (ATSDR). Toxicological Profile for Ethyl chloride (Update).Public Health Service, U.S. Department of Health and Human Services, Atlanta, GA. 1998.
U.S. Department of Health and Human Services. Hazardous Substances Data Bank (HSDB, online database). National Toxicology Information Program, National Library of Medicine, Bethesda, MD. 1993.
U.S. Department of Health and Human Services. Registry of Toxic Effects of Chemical Substances (RTECS, online database). National Toxicology Information Program, National Library of Medicine, Bethesda, MD. 1993.
U.S. Environmental Protection Agency. Integrated Risk Information System (IRIS) on Ethyl Chloride. National Center for Environmental Assessment, Office of Research and Development, Washington, DC. 1999.
National Toxicology Program. Toxicology and Carcinogenesis Studies of Ethyl chloride (Ethyl Chloride) (CAS No. 75-00-3) in F344/N Rats and B6C3F1 Mice (Inhalation Studies). TR No. 346. U.S. Department of Health and Human Services, Public Health Service, National Institutes of Health, Bethesda, MD. 1989.
The Merck Index. An Encyclopedia of Chemicals, Drugs, and Biologicals. 11th ed. Ed. S. Budavari. Merck and Co. Inc., Rahway, NJ. 1989.
J.E. Amoore and E. Hautala. Odor as an aid to chemical safety: Odor thresholds compared with threshold limit values and volatilities for 214 industrial chemicals in air and water dilution. Journal of Applied Toxicology, 3(6):272-290. 1983.
Physical properties
Clear, colorless gas or liquid with a pungent or faint, sweetish ether-like odor. When spilled, ethyl
chloride evaporates quickly. Odor threshold concentration is 4.2 ppm (quoted, Amoore and
Hautala, 1983).
Uses
Different sources of media describe the Uses of 75-00-3 differently. You can refer to the following data:
1. Ethyl chloride is used as a refrigerant, as asolvent, in the manufacture of tetraethyl lead,and as an alkylating agent. It is also used asa topical anesthetic.
2. Ethyl chloride is used as synthetic gums and thickeners in the lacquer and plastics industries. Ethyl chloride is also used in the Friedel-Crafts alkylation of benzene and other aromatics. Additional uses include solvent, refrigerant, heat-transfer medium, aerosol propellant and anesthetic.
3. Chloroethane is a useful reactant in organic synthesis.
4. Refrigerant, solvent, alkylating agent, starting point in the manufacture of tetraethyl lead: US 1907701 (1933).
Definition
Different sources of media describe the Definition of 75-00-3 differently. You can refer to the following data:
1. A highly reactive manmade volatile organic com-
pound that is highly reactive in the atmosphere. It
readily reacts with oxidizing agents to release the
chlorine atoms which, circulate and cause tropo-
spheric ozone to decompose.
2. A gaseous compound
made by the addition of hydrogen
chloride to ethene. It is used as a refrigerant
and a local anesthetic.
Indications
Chlorethane (ethyl chloride) is a highly flammable liquid that acts as a topical vapocoolant
to control pain associated with minor surgical procedures.When applied as
a spray, the product produces freezing of superficial tissues to ?20?C, which results
in insensitivity of peripheral nerve endings and local anesthesia that is maintained
up to 1 minute. Other coolant sprays can be used with the same effect.
Production Methods
Ethyl Chloride can be synthesized by treatment of ethyl alcohol with HCl, cleavage of diethylether with HCl in the presence of a catalyst (ZnCl2), chlorination of ethane or hydrochlorination of ethylene. The latter is the choice of industry. The reaction is carried out at 125 °F and 125 psi in the presence of AlCl3, which is dissolved in ethyl chloride.
General Description
A clear colorless gas with a pungent odor. Flash point -58°F. Boiling point 54°F. Less dense than water and insoluble in water. Vapors are heavier than air. Under prolonged exposure to fire or heat the containers may rupture violently and rocket.Ethyl chloride is used as a solvent for oils,resins,and waxes. It is used in medicine and as an intermediate in synthesis.
Air & Water Reactions
Highly flammable. Insoluble in water.
Reactivity Profile
CHLOROETHANE is heat sensitive. CHLOROETHANE will hydrolyze in the presence of alkalis and water. CHLOROETHANE reacts with water or steam to produce toxic and corrosive fumes. CHLOROETHANE can also react vigorously with oxidizing materials. The vapor forms highly flammable mixtures with air. A mixture of CHLOROETHANE with potassium is shock-sensitive. Contact with chemically active metals such as Na, K, Ca, powdered Al, Zn and Mg may result in violent reactions.
Hazard
Highly flammable, severe fire and explosion risk; flammable limits in air 3.8–15.4%. Irritant
to eyes. Questionable carcinogen.
Health Hazard
Different sources of media describe the Health Hazard of 75-00-3 differently. You can refer to the following data:
1. Vapor causes drunkenness, anesthesia, possible lung injury. Liquid may cause frostbite on eyes and skin.
2. Exposure to high levels of ethyl chloride cancause stupor, eye irritation, incoordination,abdominal cramps, anesthetic effects, cardiacarrest, and unconsciousness. No toxic effectswere noted at a concentration of 10,000 ppm.A 45-minute exposure to a 4% concentrationof ethyl chloride in air was lethal to guineapigs. A brief exposure for 5 to 10 minutes toa concentration of 10% of the gas was notfatal to the test animals but caused kidneyand liver damage. In humans narcotic effectsmay occur after a few inhalations of 5–10%concentrations of the gas. Irritant effectson the eyes, skin, and respiratory tract aremild. Skin contact with the liquid can causefrostbite due to cooling by rapid evaporation.LC50 value, inhalation (rats): 60,000 ppm/2 hr.
Safety Profile
Suspected carcinogen
with experimental carcinogenic and
neoplastigenic data. Mildly toxic by
inhalation. An irritant to sh, eyes, and mucous membranes. The liquid is harmful
to the eyes and can cause some irritation. In
the case of guinea pigs, the symptoms
attending exposure are similar to those
caused by methyl chloride, except that the
signs of lung irritation are not as
pronounced. It gives some warning of its
presence because it is irritating, but it is
possible to tolerate exposure to it until one
becomes unconscious. It is the least toxic
of all the chlorinated hydrocarbons. It can
cause narcosis, although the effects are
usually transient.
A very dangerous fire hazard when
exposed to heat or flame; can react
vigorously with oxidizing materials. Severe
explosion hazard when exposed to flame.
Reacts with water or steam to produce toxic
and corrosive fumes. Incompatible with
potassium. To fight fire, use carbon dioxide.
When heated to decomposition it emits
toxic fumes of phosgene and Cl-. See also
CHLORINATED HYDROCARBONS,
ALIPHATIC.
Potential Exposure
Ethyl chloride is used as an ethylating
agent in the manufacture of tetraethyl lead, dyes, drugs,
and ethyl cellulose; as a pharmaceutical, solvent; alkylating
agent; as a refrigerant and as a local anesthetic (freezing).
Carcinogenicity
The EPA has not made a
carcinogenicity assessment as yet. However, the State of
California reviewed the carcinogenicity information.
CalEPA, using the NTP study, developed a cancer
potency estimate of 4.7E-3 per mg/kg/day and defined a No
Significance Risk Level (NSRL) of 1 50 μg/day.
Increased cancer of the uterus of female mice has been
produced by exposure to 15,000 ppm, but lower concentrations
have not been studied. Rats and mice were exposed to 0
or 15,000 ppm of ethyl chloride in an NTP 2-year study with
mixed results. Results in male rats were considered
equivocal based on a combined total of five skin tumors
versus none in the control male rats. Likewise, female rats’
results were considered equivocal because three astrocytomas
were found versus none in the female control rats. The
male mouse group had such poor survival that it was deemed
an inadequate study although combined alveolar/bronchiolar
adenomas and carcinomas were reported (10/48 versus 5/50
in the control male rats). Female mice exposed to 15,000 ppm
had clear evidence of an effect, for 43/50 mice had endometrial
uterine carcinomas versus 0/49 in the female control
mice. In addition, there was a suggestion of an increase in
combined hepatocellular adenomas and carcinomas in the
female mice (8/48 exposed versus 3/49 control). There is
clear evidence for carcinogenicity in female B6C3F1 mice
and equivocal evidence in male and female F344/N rats (high
incidence of uterine carcinomas.)
Environmental fate
Photolytic. The rate constant for the reaction of chloroethane and OH radicals in the atmosphere
at 300 K is 2.3 x 10-11 cm3/molecule?sec (Hendry and Kenley, 1979). At 296 K, a photooxidation
rate constant of 3.9 x 10-13 cm3/molecule?sec was reported (Howard and Evenson, 1976). The
estimated tropospheric lifetime is 14.6 d (Nimitz and Skaggs, 1992).
Chemical/Physical. Under laboratory conditions, chloroethane hydrolyzed to ethanol (Smith and
Dragun, 1984). An estimated hydrolysis half-life in water at 25 °C and pH 7 is 38 d, with ethanol
and HCl being the expected end-products (Mabey and Mill, 1978). Based on a measured
hydrolysis rate constant of 5.1 x 10-7 at 25 °C and pH 7, the half-life is 2.6 yr (Jeffers and Wolfe,
1996).
In air, formyl chloride is the initial photooxidation product (U.S. EPA, 1985). In the presence of
water, formyl chloride hydrolyzes to HCl and carbon monoxide (Morrison and Boyd, 1971).
Burns with a smoky, greenish flame releasing hydrogen chloride (Windholz et al., 1983).
In the laboratory, the evaporation half-life of chloroethane (1 mg/L) from water at 25 °C using a
shallow-pitch propeller stirrer at 200 rpm at an average depth of 6.5 cm was 23.1 min (Dilling,
1977).
At influent concentrations of 1.0, 0.1, and 0.01 mg/L, the GAC adsorption capacities at pH 5.3
were 0.59, 0.07, and 0.007 mg/g, respectively (Dobbs and Cohen, 1980).
Solubility in water
Soluble in ethanol, ether (U.S. EPA, 1985); miscible with chlorinated hydrocarbons such as
chloroform, carbon tetrachloride, and tetrachloroethane.
Shipping
UN1037 Ethyl chloride, Hazard Class: 2.1;
Labels: 2.1-Flammable gas. Cylinders must be transported
in a secure upright position, in a well-ventilated truck.
Protect cylinder and labels from physical damage. The
owner of the compressed gas cylinder is the only entity
allowed by federal law (49CFR) to transport and refill
them. It is a violation of transportation regulations to refill
compressed gas cylinders without the express written permission of the owner.
Purification Methods
Pass ethyl chloride through absorption towers containing, successively, conc H2SO4, NaOH pellets, P2O5 on glass wool, or soda-lime, CaCl2, P2O5. Condensed it into a flask containing CaH2 and fractionally distil it. It has also been purified by illumination in the presence of bromine at 0o using a 1000W lamp, followed by washing, drying and distilling. [Beilstein 1 IV 124.]
Incompatibilities
Flammable gas. Slow reaction with
water; forms hydrogen chloride gas. Contact with moisture
(water, steam) forms hydrochloric acid and/or fumes of
hydrogen chloride. May accumulate static electrical
charges, and may cause ignition of its vapors. May form
explosive mixture with air. Contact with chemically active
metals: aluminum, lithium, magnesium, sodium, potassium,
zinc may cause fire and explosions. Attacks some plastics
and rubber.
Waste Disposal
Return refillable compressed
gas cylinders to supplier. Incineration, preferably after mixing with another combustible fuel. Care must be exercised
to assure complete combustion to prevent the formation of
phosgene. An acid scrubber is necessary to remove the halo
acids produced.
Check Digit Verification of cas no
The CAS Registry Mumber 75-00-3 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 7 and 5 respectively; the second part has 2 digits, 0 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 75-00:
(4*7)+(3*5)+(2*0)+(1*0)=43
43 % 10 = 3
So 75-00-3 is a valid CAS Registry Number.
InChI:InChI=1/C2H5Cl/c1-2-3/h2H2,1H3
75-00-3Relevant articles and documents
-
Kilpi
, p. 427 (1914)
-
Kinetics of the Liquid-Phase Hydrochlorination of Ethanol
Makhin,Dmitriev,Zanaveskin
, p. 553 - 556 (2018)
The results of a study on the kinetics of the liquid-phase hydrochlorination of ethanol with hydrogen chloride are presented. The form of the rate equation, the preexponential factor, the activation energy, and the empirical coefficients that characterize the effect of chloride anion hydration on the reaction rate of ethanol hydrochlorination were determined. The rates of hydrochlorination of monohydric alcohols and polyols were compared based on the examples of methanol, ethanol, 1,2-propylene glycol, and glycerol.
Electrophilic addition reaction of ethene with hydrogen chloride on cold molecular films: Evidence of ethyl cationic intermediate
Lee, Poong-Ryul,Lee, Chang-Woo,Kim, Joon-Ki,Moon, Eui-Seong,Kang, Heon
, p. 938 - 944 (2011)
We studied the initial-stage mechanism of the electrophilic addition reaction of ethene with HCl by examining the interactions between ethene and HCl on water-ice and frozen molecular films at temperatures of 80-140 K. Cs + reactive ion scattering (RIS) and low-energy sputtering (LES) techniques were used to probe the reaction intermediates that were kinetically trapped on the surface, in conjunction with temperature-programmed desorption (TPD) mass spectrometry to monitor the desorbing species. The reaction initially produced the π complex of HCl and ethene at temperatures below about 93 K and an "ethyl cationic species" at temperatures below about 100 K. The ethyl cationic species was formed via direct proton transfer from the HCl molecule to ethene with the assistance of water solvation, rather than via the interaction of hydronium ions and ethene. At high temperatures, this species dissociated into ethene and hydronium and chloride ions. The reaction did not, however, complete the final transition state on the ice surface to produce ethyl chloride. The observation gives evidence that the electrophilic addition reaction of ethene occurs through an ethyl-like intermediate with an ionic character. A cold ice surface can halt a reaction at an intermediate stage. An ethyl cationic intermediate is kinetically trapped on the ice surface in the course of the electrophilic addition reaction of ethene with hydrogen chloride, as revealed by reactive ion scattering and thermal desorption mass spectrometry.
Halogen-Dependent Surface Confinement Governs Selective Alkane Functionalization to Olefins
Zichittella, Guido,Scharfe, Matthias,Puértolas, Bego?a,Paunovi?, Vladimir,Hemberger, Patrick,Bodi, Andras,Szentmiklósi, László,López, Núria,Pérez-Ramírez, Javier
supporting information, p. 5877 - 5881 (2019/02/20)
The product distribution in direct alkane functionalization by oxyhalogenation strongly depends on the halogen of choice. We demonstrate that the superior selectivity to olefins over an iron phosphate catalyst in oxychlorination is the consequence of a surface-confined reaction. By contrast, in oxybromination alkane activation follows a gas-phase radical-chain mechanism and yields a mixture of alkyl bromide, cracking, and combustion products. Surface-coverage analysis of the catalyst and identification of gas-phase radicals in operando mode are correlated to the catalytic performance by a multi-technique approach, which combines kinetic studies with advanced characterization techniques such as prompt-gamma activation analysis and photoelectron photoion coincidence spectroscopy. Rationalization of gas-phase and surface contributions by density functional theory reveals that the molecular level effects of chlorine are pivotal in determining the stark selectivity differences. These results provide strategies for unraveling detailed mechanisms within complex reaction networks.
PROCESS AND INTERMEDIATE FOR THE MANUFACTURE OF DIFLUOROACETYL CHLORIDE
-
Page/Page column 14; 15, (2019/03/17)
The present invention concerns a process and intermediates for the manufacture of difluoro acetyl chloride. The invention further concerns a process for the manufacture of an agrochemically or pharmaceutically active compound, which comprises the process and intermediate for the manufacture of difluoro acetyl chloride for the manufacture of difluoro acetyl chloride or its intermediate.
