Chloromethane
Overview
 
Chloromethane, also called methyl chloride, R-40 or HCC 40, is a chemical compound
Chemical compound
A chemical compound is a pure chemical substance consisting of two or more different chemical elements that can be separated into simpler substances by chemical reactions. Chemical compounds have a unique and defined chemical structure; they consist of a fixed ratio of atoms that are held together...

 of the group of organic compound
Organic compound
An organic compound is any member of a large class of gaseous, liquid, or solid chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of carbon-containing compounds such as carbides, carbonates, simple oxides of carbon, and cyanides, as well as the...

s called haloalkane
Haloalkane
The haloalkanes are a group of chemical compounds derived from alkanes containing one or more halogens. They are a subset of the general class of halocarbons, although the distinction is not often made. Haloalkanes are widely used commercially and, consequently, are known under many chemical and...

s. It was once widely used as a refrigerant
Refrigeration
Refrigeration is a process in which work is done to move heat from one location to another. This work is traditionally done by mechanical work, but can also be done by magnetism, laser or other means...

. It is a colorless extremely flammable gas with a minorly sweet odor, which is, however, detected at possibly toxic levels. Due to concerns about its toxicity, it is no longer present in consumer products.
Chloromethane was first synthesized by the French chemists Jean-Baptiste Dumas
Jean-Baptiste Dumas
Jean Baptiste André Dumas was a French chemist, best known for his works on organic analysis and synthesis, as well as the determination of atomic weights and molecular weights by measuring vapor densities...

 and Eugene Peligot in 1835 by boiling a mixture of methanol
Methanol
Methanol, also known as methyl alcohol, wood alcohol, wood naphtha or wood spirits, is a chemical with the formula CH3OH . It is the simplest alcohol, and is a light, volatile, colorless, flammable liquid with a distinctive odor very similar to, but slightly sweeter than, ethanol...

, sulfuric acid
Sulfuric acid
Sulfuric acid is a strong mineral acid with the molecular formula . Its historical name is oil of vitriol. Pure sulfuric acid is a highly corrosive, colorless, viscous liquid. The salts of sulfuric acid are called sulfates...

, and sodium chloride
Sodium chloride
Sodium chloride, also known as salt, common salt, table salt or halite, is an inorganic compound with the formula NaCl. Sodium chloride is the salt most responsible for the salinity of the ocean and of the extracellular fluid of many multicellular organisms...

.
Encyclopedia
Chloromethane, also called methyl chloride, R-40 or HCC 40, is a chemical compound
Chemical compound
A chemical compound is a pure chemical substance consisting of two or more different chemical elements that can be separated into simpler substances by chemical reactions. Chemical compounds have a unique and defined chemical structure; they consist of a fixed ratio of atoms that are held together...

 of the group of organic compound
Organic compound
An organic compound is any member of a large class of gaseous, liquid, or solid chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of carbon-containing compounds such as carbides, carbonates, simple oxides of carbon, and cyanides, as well as the...

s called haloalkane
Haloalkane
The haloalkanes are a group of chemical compounds derived from alkanes containing one or more halogens. They are a subset of the general class of halocarbons, although the distinction is not often made. Haloalkanes are widely used commercially and, consequently, are known under many chemical and...

s. It was once widely used as a refrigerant
Refrigeration
Refrigeration is a process in which work is done to move heat from one location to another. This work is traditionally done by mechanical work, but can also be done by magnetism, laser or other means...

. It is a colorless extremely flammable gas with a minorly sweet odor, which is, however, detected at possibly toxic levels. Due to concerns about its toxicity, it is no longer present in consumer products.
Chloromethane was first synthesized by the French chemists Jean-Baptiste Dumas
Jean-Baptiste Dumas
Jean Baptiste André Dumas was a French chemist, best known for his works on organic analysis and synthesis, as well as the determination of atomic weights and molecular weights by measuring vapor densities...

 and Eugene Peligot in 1835 by boiling a mixture of methanol
Methanol
Methanol, also known as methyl alcohol, wood alcohol, wood naphtha or wood spirits, is a chemical with the formula CH3OH . It is the simplest alcohol, and is a light, volatile, colorless, flammable liquid with a distinctive odor very similar to, but slightly sweeter than, ethanol...

, sulfuric acid
Sulfuric acid
Sulfuric acid is a strong mineral acid with the molecular formula . Its historical name is oil of vitriol. Pure sulfuric acid is a highly corrosive, colorless, viscous liquid. The salts of sulfuric acid are called sulfates...

, and sodium chloride
Sodium chloride
Sodium chloride, also known as salt, common salt, table salt or halite, is an inorganic compound with the formula NaCl. Sodium chloride is the salt most responsible for the salinity of the ocean and of the extracellular fluid of many multicellular organisms...

. This method is similar to that used today.

Occurrence

Chloromethane is the most abundant organohalogen – anthropogenic or natural – in the atmosphere.

Marine

Laboratory cultures of marine phytoplankton (Phaeodactylum tricornutum, Phaeocystis sp., Thalassiosira weissflogii, Chaetoceros calcitrans, Isochrysis sp., Porphyridium sp., Synechococcus sp., Tetraselmis sp., Prorocentrum sp., and Emiliana huxleyi) produce CH3Cl, but in relatively insignificant amounts. An extensive study of 30 species of polar macroalgae revealed the release of
significant amounts of CH3Cl in only Gigartina skottsbergii and Gymnogongrus antarcticus.

Biogenesis

The salt marsh
Salt marsh
A salt marsh is an environment in the upper coastal intertidal zone between land and salt water or brackish water, it is dominated by dense stands of halophytic plants such as herbs, grasses, or low shrubs. These plants are terrestrial in origin and are essential to the stability of the salt marsh...

 plant Batis maritima contains the enzyme methyl chloride transferase
Transferase
In biochemistry, a transferase is an enzyme that catalyzes the transfer of a functional group from one molecule to another . For example, an enzyme that catalyzed this reaction would be a transferase:In this example, A would be the donor, and B would be the acceptor...

 that catalyzes the synthesis of CH3Cl from S-adenosine-L-methionine and chloride. This protein has been purified and expressed in E. coli, and seems to be present in other organisms such as white rot fungi (Phellinus pomaceus), red algae (Endocladia muricata), and the ice plant (Mesembryanthemum crystallium), each of which is a known CH3Cl producer.

Production

Large amounts of chloromethane are produced naturally in the ocean
Ocean
An ocean is a major body of saline water, and a principal component of the hydrosphere. Approximately 71% of the Earth's surface is covered by ocean, a continuous body of water that is customarily divided into several principal oceans and smaller seas.More than half of this area is over 3,000...

s by the action of sunlight on biomass
Biomass
Biomass, as a renewable energy source, is biological material from living, or recently living organisms. As an energy source, biomass can either be used directly, or converted into other energy products such as biofuel....

 and chlorine
Chlorine
Chlorine is the chemical element with atomic number 17 and symbol Cl. It is the second lightest halogen, found in the periodic table in group 17. The element forms diatomic molecules under standard conditions, called dichlorine...

 in sea foam. However, all chloromethane that is used in industry is produced synthetically.

Most chloromethane is prepared by reacting methanol
Methanol
Methanol, also known as methyl alcohol, wood alcohol, wood naphtha or wood spirits, is a chemical with the formula CH3OH . It is the simplest alcohol, and is a light, volatile, colorless, flammable liquid with a distinctive odor very similar to, but slightly sweeter than, ethanol...

 with hydrogen chloride
Hydrochloric acid
Hydrochloric acid is a solution of hydrogen chloride in water, that is a highly corrosive, strong mineral acid with many industrial uses. It is found naturally in gastric acid....

, according to the chemical equation
Chemical equation
A chemical equation is the symbolic representation of a chemical reaction where the reactant entities are given on the left hand side and the product entities on the right hand side. The coefficients next to the symbols and formulae of entities are the absolute values of the stoichiometric numbers...


CH3OH
Methanol
Methanol, also known as methyl alcohol, wood alcohol, wood naphtha or wood spirits, is a chemical with the formula CH3OH . It is the simplest alcohol, and is a light, volatile, colorless, flammable liquid with a distinctive odor very similar to, but slightly sweeter than, ethanol...

 + HCl
Hydrochloric acid
Hydrochloric acid is a solution of hydrogen chloride in water, that is a highly corrosive, strong mineral acid with many industrial uses. It is found naturally in gastric acid....

 → CH3Cl + H2O
Water
Water is a chemical substance with the chemical formula H2O. A water molecule contains one oxygen and two hydrogen atoms connected by covalent bonds. Water is a liquid at ambient conditions, but it often co-exists on Earth with its solid state, ice, and gaseous state . Water also exists in a...



This can be carried out either by bubbling hydrogen chloride gas through boiling methanol with or without a zinc chloride
Zinc chloride
Zinc chloride is the name of chemical compound with the formula ZnCl2 and its hydrates. Zinc chlorides, of which nine crystalline forms are known, are colorless or white, and are highly soluble in water. ZnCl2 itself is hygroscopic and even deliquescent. Samples should therefore be protected from...

 catalyst, or by passing combined methanol and hydrogen chloride vapors over an alumina catalyst at 350 °C.

A smaller amount of chloromethane is produced by heating a mixture of methane
Methane
Methane is a chemical compound with the chemical formula . It is the simplest alkane, the principal component of natural gas, and probably the most abundant organic compound on earth. The relative abundance of methane makes it an attractive fuel...

 and chlorine
Chlorine
Chlorine is the chemical element with atomic number 17 and symbol Cl. It is the second lightest halogen, found in the periodic table in group 17. The element forms diatomic molecules under standard conditions, called dichlorine...

 to over 400 °C. However, this method also results in more highly chlorinated compounds such as methylene chloride and chloroform
Chloroform
Chloroform is an organic compound with formula CHCl3. It is one of the four chloromethanes. The colorless, sweet-smelling, dense liquid is a trihalomethane, and is considered somewhat hazardous...

 and is usually only used when these other products are also desired.

Further reaction of chloromethane with chlorine
Chlorine
Chlorine is the chemical element with atomic number 17 and symbol Cl. It is the second lightest halogen, found in the periodic table in group 17. The element forms diatomic molecules under standard conditions, called dichlorine...

 can produce dichloromethane
Dichloromethane
Dichloromethane is an organic compound with the formula CH2Cl2. This colorless, volatile liquid with a moderately sweet aroma is widely used as a solvent. Although it is not miscible with water, it is miscible with many organic solvents...

, trichloromethane (known as chloroform) and tetrachloromethane (also known as carbon tetrachloride).

Uses

Chloromethane was a widely used refrigerant
Refrigerant
A refrigerant is a substance used in a heat cycle usually including, for enhanced efficiency, a reversible phase change from a liquid to a gas. Traditionally, fluorocarbons, especially chlorofluorocarbons, were used as refrigerants, but they are being phased out because of their ozone depletion...

, but its use has been discontinued due to its toxicity and flammability. Chloromethane was also once used for producing lead-based gasoline additives (tetramethyllead).

The most important use of chloromethane today is as a chemical intermediate in the production of silicone
Silicone
Silicones are inert, synthetic compounds with a variety of forms and uses. Typically heat-resistant and rubber-like, they are used in sealants, adhesives, lubricants, medical applications , cookware, and insulation....

 polymers. Smaller quantities are used as a solvent in the manufacture of butyl rubber
Butyl rubber
Butyl rubber is a synthetic rubber, a copolymer of isobutylene with isoprene. The abbreviation IIR stands for Isobutylene Isoprene Rubber. Polyisobutylene, also known as "PIB" or polyisobutene, n, is the homopolymer of isobutylene, or 2-methyl-1-propene, on which butyl rubber is based...

 and in petroleum refining.

Chloromethane is employed as a methylating
Methylation
In the chemical sciences, methylation denotes the addition of a methyl group to a substrate or the substitution of an atom or group by a methyl group. Methylation is a form of alkylation with, to be specific, a methyl group, rather than a larger carbon chain, replacing a hydrogen atom...

 and chlorinating agent in organic chemistry
Organic chemistry
Organic chemistry is a subdiscipline within chemistry involving the scientific study of the structure, properties, composition, reactions, and preparation of carbon-based compounds, hydrocarbons, and their derivatives...

. It is also used in a variety of other fields: as an extractant for grease
Petroleum
Petroleum or crude oil is a naturally occurring, flammable liquid consisting of a complex mixture of hydrocarbons of various molecular weights and other liquid organic compounds, that are found in geologic formations beneath the Earth's surface. Petroleum is recovered mostly through oil drilling...

s, oil
Oil
An oil is any substance that is liquid at ambient temperatures and does not mix with water but may mix with other oils and organic solvents. This general definition includes vegetable oils, volatile essential oils, petrochemical oils, and synthetic oils....

s and resin
Resin
Resin in the most specific use of the term is a hydrocarbon secretion of many plants, particularly coniferous trees. Resins are valued for their chemical properties and associated uses, such as the production of varnishes, adhesives, and food glazing agents; as an important source of raw materials...

s, as a propellant
Propellant
A propellant is a material that produces pressurized gas that:* can be directed through a nozzle, thereby producing thrust ;...

 and blowing agent
Blowing agent
A blowing agent is a substance which is capable of producing a cellular structure via a foaming process in a variety of materials that undergo hardening or phase transition, such as polymers, plastics, and metals. They are typically applied when the blown material is in a liquid stage...

 in polystyrene
Polystyrene
Polystyrene ) also known as Thermocole, abbreviated following ISO Standard PS, is an aromatic polymer made from the monomer styrene, a liquid hydrocarbon that is manufactured from petroleum by the chemical industry...

 foam production, as a local anesthetic
Local anesthetic
A local anesthetic is a drug that causes reversible local anesthesia, generally for the aim of having local analgesic effect, that is, inducing absence of pain sensation, although other local senses are often affected as well...

, as an intermediate in drug manufacturing, as a catalyst carrier in low-temperature polymerization
Polymerization
In polymer chemistry, polymerization is a process of reacting monomer molecules together in a chemical reaction to form three-dimensional networks or polymer chains...

, as a fluid for thermometric and thermostatic equipment, and as a herbicide
Herbicide
Herbicides, also commonly known as weedkillers, are pesticides used to kill unwanted plants. Selective herbicides kill specific targets while leaving the desired crop relatively unharmed. Some of these act by interfering with the growth of the weed and are often synthetic "imitations" of plant...

.

Safety

Inhalation of chloromethane gas produces central nervous system
Central nervous system
The central nervous system is the part of the nervous system that integrates the information that it receives from, and coordinates the activity of, all parts of the bodies of bilaterian animals—that is, all multicellular animals except sponges and radially symmetric animals such as jellyfish...

 effects similar to drug intoxication. Victims may feel drowsy, dizzy, or confused and have difficulty breathing, with gasping and choking, walking or speaking. At higher concentrations, paralysis
Paralysis
Paralysis is loss of muscle function for one or more muscles. Paralysis can be accompanied by a loss of feeling in the affected area if there is sensory damage as well as motor. A study conducted by the Christopher & Dana Reeve Foundation, suggests that about 1 in 50 people have been diagnosed...

, seizure
Seizure
An epileptic seizure, occasionally referred to as a fit, is defined as a transient symptom of "abnormal excessive or synchronous neuronal activity in the brain". The outward effect can be as dramatic as a wild thrashing movement or as mild as a brief loss of awareness...

s, and coma
Coma
In medicine, a coma is a state of unconsciousness, lasting more than 6 hours in which a person cannot be awakened, fails to respond normally to painful stimuli, light or sound, lacks a normal sleep-wake cycle and does not initiate voluntary actions. A person in a state of coma is described as...

 may result.

In case of ingestion nausea and vomiting may result. Skin contact when in the form of a refrigerated liquid may result in frostbite
Frostbite
Frostbite is the medical condition where localized damage is caused to skin and other tissues due to extreme cold. Frostbite is most likely to happen in body parts farthest from the heart and those with large exposed areas...

. Contact with eyes may result in dim vision, widely dilated pupils that react slowly to changes in light.

Chronic exposure to chloromethane has been linked to birth defects in mice. In humans, exposure to chloromethane during pregnancy
Pregnancy
Pregnancy refers to the fertilization and development of one or more offspring, known as a fetus or embryo, in a woman's uterus. In a pregnancy, there can be multiple gestations, as in the case of twins or triplets...

 may cause the fetus' lower spinal column, pelvis, and legs to form incorrectly, but this has not been conclusively demonstrated.

In 1997, a re-investigation of Boston's
Boston
Boston is the capital of and largest city in Massachusetts, and is one of the oldest cities in the United States. The largest city in New England, Boston is regarded as the unofficial "Capital of New England" for its economic and cultural impact on the entire New England region. The city proper had...

 Cocoanut Grove
Cocoanut Grove fire
The Cocoanut Grove was Boston's premier nightclub during the post-Prohibition 1930s and 40s. On November 28, 1942, occurred the scene of what remains the deadliest nightclub fire, killing 492 people and injuring hundreds more...

nightclub fire in 1942 cited a chloromethane leak from a refrigerator as a major cause of that disaster.

External links

The source of this article is wikipedia, the free encyclopedia.  The text of this article is licensed under the GFDL.
 
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