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Pages in category "Chloroalkanes"
The following 29 pages are in this category, out of 29 total, this list may not reflect recent changes (learn more).
|Wikimedia Commons has media related to Chloroalkanes.|
The following 29 pages are in this category, out of 29 total, this list may not reflect recent changes (learn more).
1. Carbon tetrachloride – Carbon tetrachloride, also known by many other names is an organic compound with the chemical formula CCl4. It was formerly used in fire extinguishers, as a precursor to refrigerants. It is a liquid with a sweet smell that can be detected at low levels. It has practically no flammability at lower temperatures, in 1992, production in the U. S. /Europe/Japan was estimated at 720,000 tonnes. In the carbon tetrachloride molecule, four chlorine atoms are positioned symmetrically as corners in a tetrahedral configuration joined to a carbon atom by single covalent bonds. Because of this geometry, CCl4 is non-polar. Methane gas has the structure, making carbon tetrachloride a halomethane. As a solvent, it is suited to dissolving other non-polar compounds, fats. It is somewhat volatile, giving off vapors with a characteristic of other chlorinated solvents. Solid tetrachloromethane has two polymorphs, crystalline II below −47.5 °C and crystalline I above −47.5 °C. At −47.3 °C it has monoclinic crystal structure with space group C2/c, with a specific gravity greater than 1, carbon tetrachloride will be present as a dense nonaqueous phase liquid if sufficient quantities are spilled in the environment. In organic chemistry, carbon tetrachloride serves as a source of chlorine in the Appel reaction, prior to the Montreal Protocol, large quantities of carbon tetrachloride were used to produce the chlorofluorocarbon refrigerants R-11 and R-12. However, these play a role in ozone depletion and have been phased out. Carbon tetrachloride is used to manufacture less destructive refrigerants. Carbon tetrachloride has also used in the detection of neutrinos. It once was a popular solvent in chemistry, but, because of its adverse health effects. It is sometimes useful as a solvent for infrared spectroscopy, because there are no significant absorption bands >1600 cm−1, because carbon tetrachloride does not have any hydrogen atoms, it was historically used in proton NMR spectroscopy. In addition to being toxic, its power is low
2. Chlorinated paraffins – Chlorinated paraffins are complex mixtures of polychlorinated n-alkanes. The chlorination degree of CPs can vary between 30 and 70 wt%, CPs are subdivided according to their carbon chain length into short chain CPs, medium chain CPs and long chain CPs. Depending on chain length and chlorine content, CPs are colorless or yellowish liquids or solids, Chlorinated paraffins are synthesized by reaction of chlorine gas with unbranched paraffin fractions at a temperature of 80–100 °C. The radical substitution may be promoted by UV-light, cxH + y Cl2 → CxHCly + y HCl When the desired degree of chlorination is achieved, residues of hydrochloric acid and chlorine are blown off with nitrogen. Epoxidized vegetable oil, glycidyl ether or organophosphorous compounds may be added to the product for improved stability at high temperatures. Commercial products have been classified as substances of unknown or variable composition, CPs are complex mixtures of chlorinated n-alkanes containing thousands of homologues and isomers which are not completely separated by standard analytical methods. Production of CPs for industrial use started in the 1930s, short chain CPs are classified as persistent and their physical properties imply a high potential for bioaccumulation. Furthermore, SCCPs are classified as toxic to organisms, and carcinogenic to rats. SCCPs were categorised in group 2B as possibly carcinogenic to humans from the International Agency for Research on Cancer, a global ban on SCCPs is being considered under the Stockholm Convention on Persistent Organic Pollutants. De Boer J. El-Sayed Ali T. Fiedler H. Legler J. Muir D. C, nikiforov V. A. Tomy G. T. Tsunemi, K. The handbook of environmental chemistry 10, Chlorinated paraffins, ISBN 978-3-642-10760-3 Brooke, DM, Crookes, MJ, Merckel, MD. Environmental risk assessment, long-chain chlorinated paraffins, Bristol, UK, IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. ISBN9241571810 Lassen, Carsten et al, survey of short-chain and medium-chain paraffins, Copenhagen, Danish Ministry of Environment, Environmental Protection Agency Tomy, Gregg T. et al. Chlorinated paraffins, A review of analysis and environmental occurrence, cherrie, J. W. Semple, S. Dermal Exposure to Metalworking Fluids and Medium-Chain Chlorinated Paraffin. European Union Risk assessment report Vol.4, Alkanes, C10-13, chloro, Luxembourg, European Union Risk assessment report Vol.81, Alkanes, C10-13, chloro, Luxembourg, Office for Official Publications of the European Community European Chemicals Bureau. European Union Risk assessment report Vol.58, Alkanes, C14-17, chloro, Part I-Environment, Luxembourg, European Union Risk assessment report, Alkanes, C14-17, chloro, Addendum to the final report of the risk assessment - Environment part. Luxembourg, Office for Official Publications of the European Community European Commission, analysis of short-chain chlorinated paraffins, A discussion paper. Short Chain Chlorinated Paraffins - Proposal for identification of a substance as a CMR, PBT, vPvB or a substance of an equivalent level of concern
3. Chloroethane – It is a colorless, flammable gas or refrigerated liquid with a faintly sweet odor. Some chloroethane is generated as a byproduct of polyvinyl chloride production, should demand for chloroethane continue to fall to the point where making it for its own sake is not economical, this may become the leading source of the chemical. Beginning in 1922 and continuing through most of the 20th century, the use of chloroethane was to produce tetraethyllead. TEL has been or is being phased out in most of the world. It also reacts with metal to give ethylaluminium sesquichloride, a precursor to polymers. Like other chlorinated hydrocarbons, chloroethane has been used as a refrigerant, an aerosol propellant, an anesthetic. For a time it was used as a chemical in the aluminium chloride catalyzed process to produce ethylbenzene. At present though, it is not widely used in any of these roles, the only remaining industrially important use of chloroethane is in treating cellulose to make ethylcellulose, a thickening agent and binder in paints, cosmetics, and similar products. Chloroethane is supplied as a liquid in a spray bottle propelled by its own vapor pressure and it acts as a mild topical anesthetic by its chilling effect when sprayed on skin, such as when removing splinters in a clinical setting. The heat absorbed by the liquid on tissues produces a deep and rapid chill. The vapor is flammable and narcotic, which requires care, similar to poppers, ethyl chloride is used as an inhalant during sexual activity, primarily by gay men. A small amount of the substance is placed on the tooth using a cotton wad. Chloroethanes low boiling point creates a chilling effect. If the tooth is still alive this should be sensed by the patient as mild discomfort that subsides when the wad is removed, monochloroethane is the least toxic of the chloroethanes. Like other chlorinated hydrocarbons, it is a nervous system depressant. People breathing its vapors at less than 1% concentration in air usually experience no symptoms, at concentrations of 3% to 5%, victims usually exhibit symptoms similar to those of alcohol intoxication. If exposed to higher than 6% to 8% victims often exhibit shallow breathing, loss of consciousnesses. They can be aroused with physical contact or loud noise, at this point removal from the area of exposure is advised to restore consciousness
4. Chloroform – Chloroform, or trichloromethane, is an organic compound with formula CHCl3. It is a colorless, sweet-smelling, dense liquid that is produced on a scale as a precursor to PTFE. It is also a precursor to various refrigerants and it is one of the four chloromethanes and a trihalomethane. The molecule adopts tetrahedral molecular geometry with C3v symmetry, the total global flux of chloroform through the environment is approximately 7005660000000000000♠660000 tonnes per year, and about 90% of emissions are natural in origin. Many kinds of seaweed produce chloroform, and fungi are believed to produce chloroform in soil and its half-life in air ranges from 55 to 620 days. Biodegradation in water and soil is slow, chloroform does not significantly bioaccumulate in aquatic organisms. Justus von Liebig carried out the cleavage of chloral. Eugène Soubeiran obtained the compound by the action of chlorine bleach on both ethanol and acetone, in 1834, French chemist Jean-Baptiste Dumas determined chloroforms empirical formula and named it. In 1835, Dumas prepared the substance by the cleavage of trichloroacetic acid. Regnault prepared chloroform by chlorination of chloromethane, in 1842 Dr Robert Mortimer Glover in London discovered the anaesthetic qualities of chloroform on laboratory animals. In 1847, Scottish obstetrician James Y. Simpson was the first to demonstrate the properties of chloroform on humans. By the 1850s, chloroform was being produced on a basis by using the Liebig procedure. Today, chloroform — along with dichloromethane — is prepared exclusively, in industry, chloroform is produced by heating a mixture of chlorine and either chloromethane or methane. CDCl3 is a solvent used in NMR spectroscopy. Deuterochloroform is produced by the reaction, the reaction of acetone with sodium hypochlorite or calcium hypochlorite. The haloform process is now obsolete for the production of ordinary chloroform, deuterochloroform can also be prepared by the reaction of sodium deuteroxide with chloral hydrate, or from ordinary chloroform. The haloform reaction can also occur inadvertently in domestic settings, bleaching with hypochlorite generates halogenated compounds in side reactions, chloroform is the main byproduct. Chlorodifluoromethane is then converted into tetrafluoroethylene, the precursor to Teflon
5. Dichlorobutane – Dichlorobutane is a chloroalkane with the molecular formula C4H8Cl2. There are many substances encompassed under this general name and they are obtained by common synthesis methods for chloroalkanes. Dichlorobutane isomers are further utilized in industrial and laboratory organic syntheses. Of most note is 1, 4-dichlorobutane, which can be used, among others, as with most chloroalkanes, dichlorobutanes are irritants and quite flammable
6. 1,1-Dichloroethane – It is a colorless oily liquid with a chloroform-like odor. It is not easily soluble in water, but miscible with most organic solvents, large volumes of 1, 1-dichloroethane are manufactured, with annual production exceeding 1 million pounds in the United States. It is mainly used as a feedstock in chemical synthesis, chiefly of 1,1, 1-trichloroethane. It is also used as a solvent for plastics, oils and fats, as a degreaser, as a fumigant in insecticide sprays, in fire extinguishers. It is used in manufacturing of high-vacuum resistant rubber and for extraction of temperature-sensitive substances, thermal cracking at 400–500 °C and 10 MPa yields vinyl chloride. In the past,1, 1-dichloroethane was used as a surgical inhalational anesthetic, in the atmosphere,1, 1-dichloroethane decomposes with half-life of 62 days, chiefly by reaction of photolytically produced hydroxyl radicals. Dichloroethane and Dichloroethene on members. optushome. com. au ATSDR - Toxic Substances Portal CDC - NIOSH Pocket Guide to Chemical Hazards
7. 1,2-Dichloroethane – The chemical compound 1, 2-dichloroethane commonly known as ethylene dichloride, is a chlorinated hydrocarbon. It is a liquid with a chloroform-like odour.1, 2-Dichloroethane is also used generally as an intermediate for other organic chemical compounds. It forms azeotropes with many solvents, including water and other chlorocarbons. Although the Gezelschap in practice did not do much in-depth scientific research, they, part of that acknowledgement is that 1, 2-dichloroethane was called Dutch oil in old chemistry. Nearly 20 million tons of 1, 2-dichloroethane are produced in the United States, Western Europe, production is primarily achieved through the iron chloride-catalysed reaction of ethene and chlorine. Approximately 80% of the production of 1, 2-dichloroethane is used in the production of vinyl chloride monomer with hydrogen chloride as a byproduct. VCM is the precursor to polyvinyl chloride, cl−CH2−CH2−Cl → H2C=CH−Cl + HCl The hydrogen chloride can be re-used in the production of more 1, 2-dichloroethane via the oxychlorination route described above. As a good polar solvent,1, 2-dichloroethane could be used as degreaser and paint remover but is now banned from use due to its toxicity. As a useful building block reagent, it is used as an intermediate in the production of organic compounds such as ethylenediamine. In the laboratory it is used as a source of chlorine, with elimination of ethene. Via several steps,1, 2-dichloroethane is a precursor to 1,1, 1-trichloroethane, historically,1, 2-dichloroethane was used as an anti-knock additive in leaded fuels to scavenge lead from cylinders and valves preventing buildup. 1, 2-Dichloroethane is toxic, highly flammable, and possibly carcinogenic and its high solubility and 50-year half-life in anoxic aquifers make it a perennial pollutant and health risk that is very expensive to treat conventionally, requiring a method of bioremediation. Substitutes are recommended and will vary according to application, dioxolane and toluene are possible substitutes as solvents. Dichloroethane is unstable in the presence of metal and, when moist, with zinc
8. Dichloromethane – Dichloromethane is an organic compound with the formula CH2Cl2. This colorless, volatile liquid with a sweet aroma is widely used as a solvent. Although it is not miscible with water, it is miscible with organic solvents. One of the most well-known applications of dichloromethane is in the drinking bird heat engine, natural sources of dichloromethane include oceanic sources, macroalgae, wetlands, and volcanoes. However, the majority of dichloromethane in the environment is the result of industrial emissions, DCM is produced by treating either chloromethane or methane with chlorine gas at 400–500 °C. At these temperatures, both methane and chloromethane undergo a series of reactions producing progressively more chlorinated products, in this way, an estimated 400,000 tons were produced in the US, Europe, and Japan in 1993. These compounds are separated by distillation, DCM was first prepared in 1839 by the French chemist Henri Victor Regnault, who isolated it from a mixture of chloromethane and chlorine that had been exposed to sunlight. DCMs volatility and ability to dissolve a wide range of organic compounds makes it a useful solvent for chemical processes. It is widely used as a paint stripper and a degreaser, in the food industry, it has been used to decaffeinate coffee and tea as well as to prepare extracts of hops and other flavorings. Its volatility has led to its use as an aerosol spray propellant, the chemical compounds low boiling point allows the chemical to function in a heat engine that can extract mechanical energy from small temperature differences. An example of a DCM heat engine is the drinking bird, the toy works at room temperature. For example, it is used to seal the casing of electric meters, often sold as a main component of plastic welding adhesives, it is also used extensively by model building hobbyists for joining plastic components together. It is commonly referred to as Di-clo and it is used in the garment printing industry for removal of heat-sealed garment transfers, and its volatility is exploited in novelty items, bubble lights and jukebox displays. DCM is the least toxic of the simple chlorohydrocarbons, but it is not without health risks and it can also be absorbed through the skin. More severe consequences can include suffocation, loss of consciousness, coma, DCM is also metabolized by the body to carbon monoxide potentially leading to carbon monoxide poisoning. Acute exposure by inhalation has resulted in optic neuropathy and hepatitis, prolonged skin contact can result in DCM dissolving some of the fatty tissues in skin, resulting in skin irritation or chemical burns. It may be carcinogenic, as it has linked to cancer of the lungs, liver. Other animal studies showed breast cancer and salivary gland cancer, research is not yet clear as to what levels may be carcinogenic
9. 1,2-Dichloropropane – 1, 2-Dichloropropane is an organic compound classified as a chlorocarbon. It is a colorless, flammable liquid with a sweet odor and it is obtained as a byproduct of the production of epichlorohydrin, which is produced on a large scale. 1, 2-Dichloropropane is an intermediate in the production of perchloroethylene, thus, there is reasonable evidence that 1, 2-dichloropropane may be a carcinogen. Data from animal studies show tumor growth in the liver and mammary glands, further animal studies involving inhalation toxicity data has caused the National Institute for Occupational Safety and Health to classify 1, 2-dichloropropane as a carcinogen and IDLH
10. Hexachloroethane – Hexachloroethane, also known as perchloroethane, C2Cl6, is a white crystalline solid at room temperature with a camphor-like odor. It has been used by the military in smoke compositions, such as base-eject smoke munitions, Hexachloroethane is a byproduct of many industrial chlorination processes. It is currently being manufactured directly in India, the overall reaction is shown below. C2H6 +6 Cl2 → C2Cl6 +6 HCl Hexachloroethane has been used in the formulation of extreme pressure lubricants and it has also been used as a chain transfer agent in the emulsion polymerization of propylene tetrafluoroethylene copolymer. Smoke grenades, called hexachloroethane smoke or HC smoke, utilize a mixture containing roughly equal parts of HCE and zinc oxide and these smokes are toxic, which is attributed to the production of zinc chloride. Hexachloroethane has been used manufacture degassing pellets to remove hydrogen gas bubbles from molten aluminum in aluminum foundries and this use, as well as similar uses in magnesium, is being phased out in the European Union. It was phased out as early as 1999 in the United States, hexachlorethane is not particularly toxic when taken orally, but is considered to be quite toxic by skin adsorption. The primary effect is depression of the nervous system. The IDLH is given as 300 ppm and the OSHA PEL is 1 ppm and it is reasonably anticipated to be a carcinogen
11. Isopropyl chloride – Isopropyl chloride is a colorless, flammable chemical compound. It has the chemical formula C3H7Cl and is prepared by refluxing isopropyl alcohol with concentrated hydrochloric acid, to compare, its structural isomer, 1-chloropropane, is instead an example of a primary haloalkane, as the chlorine-bound carbon atom has only one C-C bond. As a laboratory reactant, heating 2-chloropropane with alcoholic potassium hydroxide will yield propene by a dehydrohalogenation reaction, however, reacting with potassium hydroxide would compete with an SN2 nucleophilic substitution reaction because OH−-ion is a strong, sterically unhindered nucleophile. Because of this, potassium tert-butoxide is one example of a reagent to use
12. 1,1,2,2-Tetrachloroethane – 1,1,2, 2-Tetrachloroethane is a chlorinated derivative of ethane. It has the highest solvent power of any chlorinated hydrocarbon, as a refrigerant, it is used under the name R-130. It was once used as a solvent and as an intermediate in the industrial production of trichloroethylene, tetrachloroethylene. However,1,1,2, 2-tetrachloroethane is no longer used much in the United States due to concerns about its toxicity, chronic inhalation exposure in humans results in jaundice and an enlarged liver, headaches, tremors, dizziness, numbness, and drowsiness. The U. S. Environmental Protection Agency has classified it as a Group C possible human carcinogen, for occupational exposure limits, the Occupational Safety and Health Administration has set a permissible exposure limit for dermal exposures at 5 ppm over an eight-hour time-weighted average. The National Institute for Occupational Safety and Health has a more protective recommended exposure limit for dermal exposures at 1 ppm over an eight-hour time-weighted average
13. 1,1,1-Trichloroethane – The organic compound 1,1, 1-trichloroethane, also known as methyl chloroform, is a chloroalkane. This colourless, sweet-smelling liquid was once produced industrially in large quantities for use as a solvent and it is regulated by the Montreal Protocol as an ozone-depleting substance and its use is being rapidly phased out. 1,1, 1-Trichloroethane was first reported by Henri Victor Regnault in 1840, industrially, it is usually produced in a two-step process from vinyl chloride. The major side-product is the related compound 1,1, 2-trichloroethane, from which the 1,1, stabilizers comprise up to 8% of the formulation, including acid scavengers and complexants. The Montreal Protocol targeted 1,1, 1-trichloroethane as one of those responsible for ozone depletion. Since then, its manufacture and use has been phased out throughout most of the world,1,1, 1-trichloroethane is generally considered a non-polar solvent. Owing to the polarizability of the chlorine atoms, it is a superior solvent for organic compounds that do not dissolve well in hydrocarbons such as hexane. It is an excellent solvent for organic materials and also one of the least toxic of the chlorinated hydrocarbons. 1,1, 1-trichloroethane is also used as an insecticidal fumigant and it was also the standard cleaner for photographic film. Other commonly available solvents damage emulsion, and thus are not suitable for this application, the standard replacement, Forane 141 is much less effective, and tends to leave a residue. 1,1, 1-trichloroethane was used as a thinner in correction fluid products such as liquid paper, many of its applications previously used carbon tetrachloride. In turn,1,1, 1-trichloroethane itself is now being replaced by other solvents in the laboratory, fatal poisonings and illnesses linked to intentional inhalation of trichloroethane have been reported. Studies on laboratory animals have shown that 1,1, 1-trichloroethane is not retained in the body for long periods of time, however, chronic exposure has been linked to abnormalities in the liver, kidneys, and heart. Pregnant women should avoid exposure, as the compound has been linked to birth defects in laboratory animals
14. 1,1,2-Trichloroethane – 1,1, 2-Trichloroethane, or 1,1, 2-TCA, is an organochloride solvent with the molecular formula C2H3Cl3. It is a colourless, sweet-smelling liquid that does not dissolve in water and it is an isomer of 1,1, 1-trichloroethane. It is used as a solvent and as an intermediate in the synthesis of 1,1,1, 2-TCA is a central nervous system depressant and inhalation of vapors may cause dizziness, drowsiness, headache, nausea, shortness of breath, unconsciousness, or cancer. Trichloroethane may be harmful by inhalation, ingestion and skin contact and it is a respiratory and eye irritant. It is considered to be a potential occupational carcinogen
15. 1,2,3-Trichloropropane – 1,2, 3-Trichloropropane is a chemical compound that was an impurity in 1, 3-dichloropropene fumigants manufactured by Shell Chemical Company and Dow Chemical Company. Exposure by inhalation, skin contact, or ingestion can be harmful to health,1,2, 3-Trichloropropane can be produced via the chlorination of propylene. TCP also may be produced as a byproduct of processes used to produce chemicals such as dichloropropene, propylene chlorohydrin, propylene oxide, dichlorohydrin. Historically, TCP has been used as a paint or varnish remover, a cleaning and degreasing agent and it is also used as a chemical intermediate in the process of making chemicals, such as hexafluoropropylene and polysulfides, and as an industrial solvent. Solvent 1,2, 3-TCP had purportedly been used in the past as a solvent for paint and varnish removal, as a cleaning and degreasing agent, no current information is available to indicate that it continues to be used for these purposes. Soil fumigants Pre-1980s, agricultural use of chloropropane-containing soil fumigants for use as pesticides and nematicides was prevalent in the United States. D-D was first marketed in 1943, but is no longer available in the United States, and has replaced with Telone II. Telone II reportedly contains as much as 99 percent 1, 3-dichloropropene and up to 0.17 percent by weight 1,2, over 2 million pounds of pesticides containing 1, 3-dichloropropene were used in California alone in 1978. Telone II is still used for vegetables, field crops, fruit and nut trees, grapes, nursery crops, aircraft fuel tank sealers Another documented use of 1,2, 3-TCP was as a “branching” or curing agent in polysulfide polymers. Polysulfide polymers have been used as the “standard sealant for virtually all aircraft fuel tanks, also, “one of the first large-scale applications of the liquid polysulfides was as a binder for rocket fuel, ” from 1946 until 1958. Chemical intermediates By the early 1980s, approximately 95 percent of chloropropanes were being used as chemical intermediates, Chemical intermediates are industrial chemicals that are used as the starting point to produce other chemicals. 1,2, 3-TCP is currently used as an intermediate in the production of polysulfone liquid polymers, the synthesis of hexafluoropropylene, polysulfides are used as catalyst sulfidation agents and in the formulation of lubricant additives created for use in high-pressure environments or applications. Manufacturers 1,2, 3-TCP is manufactured as a product in the United States. Humans can be exposed to TCP by inhaling its fumes or through skin contact, TCP is recognized in California as a human carcinogen, and extensive animal studies have shown that it causes cancer. Short term exposure to TCP can cause throat and eye irritation, long term exposure can affect body weight and kidney function. In a drinking water project proposed by the United States Environmental Protection Agency, CDPH is working to establish legally enforceable Maximum Contaminant Level which is set as close to the PHG as is technically and economically feasible. The state of Alaska has promulgated standards establishing cleanup levels for 1,2, 3-trichloropropane contamination in soils, the state of California considers 1,2, 3-trichloropropane to be an unregulated contaminant that should be monitored. The state of Colorado has also promulgated a groundwater standard although there is no drinking water standard, although there is not much regulation on this substance, it has proved that TCP is a carcinogen in laboratory mice, and most likely a human carcinogen as well