Methyl Chloride
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Chloromethane, also called methyl chloride, Refrigerant-40, R-40 or HCC 40, is an
organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...
with the chemical formula . One of the
haloalkane The haloalkanes (also known as halogenoalkanes or alkyl halides) are alkanes containing one or more halogen substituents. They are a subset of the general class of halocarbons, although the distinction is not often made. Haloalkanes are widely us ...
s, it is a colorless, odorless, flammable gas. Methyl chloride is a crucial
reagent In chemistry, a reagent ( ) or analytical reagent is a substance or compound added to a system to cause a chemical reaction, or test if one occurs. The terms ''reactant'' and ''reagent'' are often used interchangeably, but reactant specifies a ...
in industrial chemistry, although it is rarely present in consumer products, and was formerly utilized as a
refrigerant A refrigerant is a working fluid used in the heat pump and refrigeration cycle, refrigeration cycle of air conditioning systems and heat pumps where in most cases they undergo a repeated phase transition from a liquid to a gas and back again. Ref ...
.


Occurrence

Chloromethane is an abundant
organohalogen Halocarbon compounds are chemicals in which one or more carbon atoms are linked by covalent bonds with one or more halogen atoms (fluorine, chlorine, bromine or iodine – ) resulting in the formation of organofluorine compounds, organochlori ...
, anthropogenic or natural, in the atmosphere.


Marine

Laboratory cultures of marine
phytoplankton Phytoplankton () are the autotrophic (self-feeding) components of the plankton community and a key part of ocean and freshwater ecosystems. The name comes from the Greek words (), meaning 'plant', and (), meaning 'wanderer' or 'drifter'. Ph ...
(''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 A salt marsh or saltmarsh, also known as a coastal salt marsh or a tidal marsh, is a coastal ecosystem in the upper coastal intertidal zone between land and open saltwater or brackish water that is regularly flooded by the tides. It is dominated ...
plant ''Batis maritima'' contains the enzyme
methyl chloride transferase Methyl halide transferase (, ''MCT'', methyl chloride transferase, ''S-adenosyl-L-methionine:halide/bisulfide methyltransferase'', ''AtHOL1'', ''AtHOL2'', ''AtHOL3'', ''HMT'', ''S-adenosyl-L-methionine: halide ion methyltransferase'', ''SAM:halide ...
that catalyzes the synthesis of CH3Cl from S-adenosine-L-methionine and chloride. This protein has been purified and expressed in ''
E. coli ''Escherichia coli'' (),Wells, J. C. (2000) Longman Pronunciation Dictionary. Harlow ngland Pearson Education Ltd. also known as ''E. coli'' (), is a Gram-negative, facultative anaerobic, rod-shaped, coliform bacterium of the genus ''Escher ...
'', and seems to be present in other organisms such as white rot fungi (''
Phellinus pomaceus ''Phellinus pomaceus'' is a plant pathogen particularly common on ''Prunus ''Prunus'' is a genus of trees and shrubs, which includes (among many others) the fruits plums, cherries, peaches, nectarines, apricots, and almonds. Native to t ...
''), red algae ('' Endocladia muricata''), and the ice plant (''
Mesembryanthemum crystallinum ''Mesembryanthemum crystallinum'' is a prostrate succulent plant native to Africa, Sinai and southern Europe, and naturalized in the New World. The plant is covered with large, glistening bladder cells or water vesicles, reflected in its common n ...
''), each of which is a known CH3Cl producer.


Sugarcane and the emission of methyl chloride

In the sugarcane industry, the organic waste is usually burned in the power
cogeneration Cogeneration or combined heat and power (CHP) is the use of a heat engine or power station to generate electricity and useful heat at the same time. Cogeneration is a more efficient use of fuel or heat, because otherwise- wasted heat from elect ...
process. When contaminated by chloride, this waste burns, releasing methyl chloride in the atmosphere.


Interstellar detections

Chloromethane has been detected in the low-mass Class 0 protostellar binary, IRAS 16293–2422, using the
Atacama Large Millimeter Array The Atacama Large Millimeter/submillimeter Array (ALMA) is an astronomical interferometer of 66 radio telescopes in the Atacama Desert of northern Chile, which observe electromagnetic radiation at millimeter and submillimeter wavelengths. The a ...
(ALMA). It was also detected in the comet
67P/Churyumov–Gerasimenko 67P/Churyumov–Gerasimenko (abbreviated as 67P or 67P/C–G) is a Jupiter-family comet, originally from the Kuiper belt, with a current orbital period of 6.45 years, a rotation period of approximately 12.4 hours and a maximum velocity of . Chu ...
(67P/C-G) using the Rosetta Orbiter Spectrometer for Ion and Neutral Analysis (ROSINA) instrument on the
Rosetta Rosetta or Rashid (; ar, رشيد ' ; french: Rosette  ; cop, ϯⲣⲁϣⲓⲧ ''ti-Rashit'', Ancient Greek: Βολβιτίνη ''Bolbitinē'') is a port city of the Nile Delta, east of Alexandria, in Egypt's Beheira governorate. The Ro ...
spacecraft. The detections reveal that chloromethane can be formed in star-forming regions before planets or life is formed.


Production

Chloromethane was first synthesized by the French chemists
Jean-Baptiste Dumas Jean Baptiste André Dumas (14 July 180010 April 1884) was a French chemist, best known for his works on organic analysis and synthesis, as well as the determination of atomic weights (relative atomic masses) and molecular weights by measuring v ...
and
Eugene Peligot Eugene may refer to: People and fictional characters * Eugene (given name), including a list of people and fictional characters with the given name * Eugene (actress) (born 1981), Kim Yoo-jin, South Korean actress and former member of the sin ...
in 1835 by boiling a mixture of
methanol Methanol (also called methyl alcohol and wood spirit, amongst other names) is an organic chemical and the simplest aliphatic alcohol, with the formula C H3 O H (a methyl group linked to a hydroxyl group, often abbreviated as MeOH). It is a ...
,
sulfuric acid Sulfuric acid (American spelling and the preferred IUPAC name) or sulphuric acid ( Commonwealth spelling), known in antiquity as oil of vitriol, is a mineral acid composed of the elements sulfur, oxygen and hydrogen, with the molecular formu ...
, and
sodium chloride Sodium chloride , commonly known as salt (although sea salt also contains other chemical salts), is an ionic compound with the chemical formula NaCl, representing a 1:1 ratio of sodium and chloride ions. With molar masses of 22.99 and 35.45 g ...
. This method is the forerunner for that used today but uses
hydrogen chloride The compound hydrogen chloride has the chemical formula and as such is a hydrogen halide. At room temperature, it is a colourless gas, which forms white fumes of hydrochloric acid upon contact with atmospheric water vapor. Hydrogen chloride ga ...
instead of sulfuric acid and sodium chloride. Chloromethane is produced commercially by treating
methanol Methanol (also called methyl alcohol and wood spirit, amongst other names) is an organic chemical and the simplest aliphatic alcohol, with the formula C H3 O H (a methyl group linked to a hydroxyl group, often abbreviated as MeOH). It is a ...
with
hydrochloric acid Hydrochloric acid, also known as muriatic acid, is an aqueous solution of hydrogen chloride. It is a colorless solution with a distinctive pungent smell. It is classified as a strong acid Acid strength is the tendency of an acid, symbol ...
or hydrogen chloride, according to the
chemical equation A chemical equation is the symbolic representation of a chemical reaction in the form of symbols and chemical formulas. The reactant entities are given on the left-hand side and the product entities on the right-hand side with a plus sign between ...
: : CH3OH + HCl → CH3Cl + H2O A smaller amount of chloromethane is produced by treating a mixture of
methane Methane ( , ) is a chemical compound with the chemical formula (one carbon atom bonded to four hydrogen atoms). It is a group-14 hydride, the simplest alkane, and the main constituent of natural gas. The relative abundance of methane on Eart ...
with
chlorine Chlorine is a chemical element with the Symbol (chemistry), symbol Cl and atomic number 17. The second-lightest of the halogens, it appears between fluorine and bromine in the periodic table and its properties are mostly intermediate betwee ...
at elevated temperatures. This method, however, also produces more highly chlorinated compounds such as
dichloromethane Dichloromethane (DCM or methylene chloride, methylene bichloride) is an organochlorine compound with the formula . This colorless, volatile liquid with a chloroform-like, sweet odour is widely used as a solvent. Although it is not miscible with ...
,
chloroform Chloroform, or trichloromethane, is an organic compound with chemical formula, formula Carbon, CHydrogen, HChlorine, Cl3 and a common organic solvent. It is a colorless, strong-smelling, dense liquid produced on a large scale as a precursor to ...
, and
carbon tetrachloride Carbon tetrachloride, also known by many other names (such as tetrachloromethane, also IUPAC nomenclature of inorganic chemistry, recognised by the IUPAC, carbon tet in the cleaning industry, Halon-104 in firefighting, and Refrigerant-10 in HVAC ...
. For this reason, methane chlorination is usually only practiced when these other products are also desired. This chlorination method also cogenerates hydrogen chloride, which poses a disposal problem.


Dispersion in the environment

Most of the methyl chloride present in the environment ends up being released to the
atmosphere An atmosphere () is a layer of gas or layers of gases that envelop a planet, and is held in place by the gravity of the planetary body. A planet retains an atmosphere when the gravity is great and the temperature of the atmosphere is low. A s ...
. After being released into the air, the atmospheric lifetime of this substance is about 10 months with multiple natural sinks, such as ocean, transport to the stratosphere, soil, etc. On the other hand, when the methyl chloride emitted is released to water, it will be rapidly lost by
volatilization Volatilization is the process whereby a dissolved sample is vaporised. In atomic spectroscopy this is usually a two-step process. The analyte is turned into small droplets in a nebuliser which are entrained in a gas flow which is in turn volatilis ...
. The alf-lifeof this substance in terms of volatilization in the river, lagoon and lake is 2.1 h, 25 h and 18 days, respectively. The amount of methyl chloride in the
stratosphere The stratosphere () is the second layer of the atmosphere of the Earth, located above the troposphere and below the mesosphere. The stratosphere is an atmospheric layer composed of stratified temperature layers, with the warm layers of air ...
is estimated to be 2 x 106 tonnes per year, representing 20-25% of the total amount of chlorine that is emitted to the stratosphere annually.


Uses

Large scale use of chloromethane is for the production of
dimethyldichlorosilane Dimethyldichlorosilane is a tetrahedral, organosilicon compound with the formula Si(CH3)2Cl2. At room temperature it is a colorless liquid that readily reacts with water to form both linear and cyclic Si-O chains. Dimethyldichlorosilane is made ...
and related
organosilicon compound Organosilicon compounds are organometallic compounds containing carbon–silicon chemical bond, bonds. Organosilicon chemistry is the corresponding science of their preparation and properties. Most organosilicon compounds are similar to the ordin ...
s. These compounds arise via the direct process. The relevant reactions are (Me = CH3): :x MeCl + Si → Me3SiCl, Me2SiCl2, MeSiCl3, Me4Si2Cl2, ...
Dimethyldichlorosilane Dimethyldichlorosilane is a tetrahedral, organosilicon compound with the formula Si(CH3)2Cl2. At room temperature it is a colorless liquid that readily reacts with water to form both linear and cyclic Si-O chains. Dimethyldichlorosilane is made ...
(Me2SiCl2) is of particular value as a precursor to
silicone A silicone or polysiloxane is a polymer made up of siloxane (−R2Si−O−SiR2−, where R = organic group). They are typically colorless oils or rubber-like substances. Silicones are used in sealants, adhesives, lubricants, medicine, cooking ...
s, but
trimethylsilyl chloride Trimethylsilyl chloride, also known as chlorotrimethylsilane is an organosilicon compound ( silyl halide), with the formula (CH3)3SiCl, often abbreviated Me3SiCl or TMSCl. It is a colourless volatile liquid that is stable in the absence of water. ...
(Me3SiCl) and
methyltrichlorosilane Methyltrichlorosilane, also known as trichloromethylsilane, is a monomer and organosilicon compound with the formula CH3SiCl3. It is a colorless liquid with a sharp odor similar to that of hydrochloric acid. As methyltrichlorosilane is a reacti ...
(MeSiCl3) are also valuable. Smaller quantities are used as a solvent in the manufacture of
butyl rubber Butyl rubber, sometimes just called "butyl", 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, (C4H8)n, is the ho ...
and in
petroleum refining An oil refinery or petroleum refinery is an industrial processes, industrial process Factory, plant where petroleum (crude oil) is transformed and refining, refined into useful products such as gasoline (petrol), diesel fuel, asphalt, asphalt ...
. Chloromethane is employed as a methylating and chlorinating agent, e.g. the production of
methylcellulose Methyl cellulose (or methylcellulose) is a compound derived from cellulose. It is sold under a variety of trade names and is used as a thickener and emulsifier in various food and cosmetic products, and also as a bulk-forming laxative. Like cellu ...
. It is also used in a variety of other fields: as an extractant for greases,
oil An oil is any nonpolar chemical substance that is composed primarily of hydrocarbons and is hydrophobic (does not mix with water) & lipophilic (mixes with other oils). Oils are usually flammable and surface active. Most oils are unsaturated ...
s, and
resin In polymer chemistry and materials science, resin is a solid or highly viscous substance of plant or synthetic origin that is typically convertible into polymers. Resins are usually mixtures of organic compounds. This article focuses on natu ...
s, as a
propellant A propellant (or propellent) is a mass that is expelled or expanded in such a way as to create a thrust or other motive force in accordance with Newton's third law of motion, and "propel" a vehicle, projectile, or fluid payload. In vehicles, the e ...
and
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 wh ...
in
polystyrene Polystyrene (PS) is a synthetic polymer made from monomers of the aromatic hydrocarbon styrene. Polystyrene can be solid or foamed. General-purpose polystyrene is clear, hard, and brittle. It is an inexpensive resin per unit weight. It is a ...
foam production, as a
local anesthetic A local anesthetic (LA) is a medication that causes absence of pain sensation. In the context of surgery, a local anesthetic creates an absence of pain in a specific location of the body without a loss of consciousness, as opposed to a general an ...
, as an intermediate in drug manufacturing, as a
catalyst Catalysis () is the process of increasing the rate of a chemical reaction by adding a substance known as a catalyst (). Catalysts are not consumed in the reaction and remain unchanged after it. If the reaction is rapid and the catalyst recyc ...
carrier in low-temperature
polymerization In polymer chemistry, polymerization (American English), or polymerisation (British English), is a process of reacting monomer, monomer molecules together in a chemical reaction to form polymer chains or three-dimensional networks. There are ...
, as a fluid for thermometric and thermostatic equipment, and as a
herbicide Herbicides (, ), also commonly known as weedkillers, are substances used to control undesired plants, also known as weeds.EPA. February 201Pesticides Industry. Sales and Usage 2006 and 2007: Market Estimates. Summary in press releasMain page fo ...
.


Obsolete applications

Chloromethane was a widely used
refrigerant A refrigerant is a working fluid used in the heat pump and refrigeration cycle, refrigeration cycle of air conditioning systems and heat pumps where in most cases they undergo a repeated phase transition from a liquid to a gas and back again. Ref ...
, but its use has been discontinued. Chloromethane was also once used for producing lead-based gasoline additives (
tetramethyllead Tetramethyllead, also called tetra methyllead and lead tetramethyl, is a chemical compound used as an antiknock additive for gasoline. Its use is being phased out for environmental considerations. The National Institute for Occupational Safety a ...
).


Safety

Inhalation of chloromethane gas produces
central nervous system The central nervous system (CNS) is the part of the nervous system consisting primarily of the brain and spinal cord. The CNS is so named because the brain integrates the received information and coordinates and influences the activity of all par ...
effects similar to
alcohol intoxication Alcohol intoxication, also known as alcohol poisoning, commonly described as drunkenness or inebriation, is the negative behavior and physical effects caused by a recent consumption of alcohol. In addition to the toxicity of ethanol, the main p ...
. The TLV is 50 ppm and the MAC is the same. Prolonged exposure may have mutagenic effects.


References


External links

* *
Data sheet at inchem.orgInformation about chloromethane
* ttp://www.inchem.org/documents/iarc/vol71/026-methylchloride.html IARC Summaries & Evaluations Vol. 71 (1999)* Ohligschläger et al. (2020). Chloromethanes. In Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a06_233.pub4 {{Authority control Greenhouse gases Halogenated solvents Halomethanes Hazardous air pollutants IARC Group 3 carcinogens Chloroalkanes Refrigerants Halogen-containing natural products Methylating agents