Dichloromethane
Encyclopedia
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...
with the formula
Chemical formula
A chemical formula or molecular formula is a way of expressing information about the atoms that constitute a particular chemical compound....
C
Carbon
Carbon is the chemical element with symbol C and atomic number 6. As a member of group 14 on the periodic table, it is nonmetallic and tetravalent—making four electrons available to form covalent chemical bonds...
H
Hydrogen
Hydrogen is the chemical element with atomic number 1. It is represented by the symbol H. With an average atomic weight of , hydrogen is the lightest and most abundant chemical element, constituting roughly 75% of the Universe's chemical elemental mass. Stars in the main sequence are mainly...
2Cl
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...
2. This colorless, volatile liquid with a moderately sweet aroma is widely used as a solvent
Solvent
A solvent is a liquid, solid, or gas that dissolves another solid, liquid, or gaseous solute, resulting in a solution that is soluble in a certain volume of solvent at a specified temperature...
. Although it is not miscible with water, it is miscible with many organic solvent
Solvent
A solvent is a liquid, solid, or gas that dissolves another solid, liquid, or gaseous solute, resulting in a solution that is soluble in a certain volume of solvent at a specified temperature...
s. It was first prepared in 1840 by the French
France
The French Republic , The French Republic , The French Republic , (commonly known as France , is a unitary semi-presidential republic in Western Europe with several overseas territories and islands located on other continents and in the Indian, Pacific, and Atlantic oceans. Metropolitan France...
chemist
Chemist
A chemist is a scientist trained in the study of chemistry. Chemists study the composition of matter and its properties such as density and acidity. Chemists carefully describe the properties they study in terms of quantities, with detail on the level of molecules and their component atoms...
Henri Victor Regnault
Henri Victor Regnault
Henri Victor Regnault was a French chemist and physicist best known for his careful measurements of the thermal properties of gases. He was an early thermodynamicist and was mentor to William Thomson in the late 1840s....
, who isolated it from a mixture of chloromethane
Chloromethane
Chloromethane, also called methyl chloride, R-40 or HCC 40, is a chemical compound of the group of organic compounds called haloalkanes. It was once widely used as a refrigerant. It is a colorless extremely flammable gas with a minorly sweet odor, which is, however, detected at possibly toxic levels...
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...
that had been exposed to sunlight
Sunlight
Sunlight, in the broad sense, is the total frequency spectrum of electromagnetic radiation given off by the Sun. On Earth, sunlight is filtered through the Earth's atmosphere, and solar radiation is obvious as daylight when the Sun is above the horizon.When the direct solar radiation is not blocked...
.
Production
Dichloromethane is produced by treatingChemical reaction
A chemical reaction is a process that leads to the transformation of one set of chemical substances to another. Chemical reactions can be either spontaneous, requiring no input of energy, or non-spontaneous, typically following the input of some type of energy, such as heat, light or electricity...
either methyl chloride or methane with chlorine gas at 400–500 °C. At these temperatures, both 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 methyl chloride undergo a series of reactions producing progressively more chlorinated products.
- CH4MethaneMethane 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...
+ Cl2ChlorineChlorine 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...
→ CH3Cl + HClHydrogen chlorideThe compound hydrogen chloride has the formula HCl. At room temperature, it is a colorless gas, which forms white fumes of hydrochloric acid upon contact with atmospheric humidity. Hydrogen chloride gas and hydrochloric acid are important in technology and industry... - CH3Cl + Cl2 → CH2Cl2 + HCl
- CH2Cl2 + Cl2 → CHCl3ChloroformChloroform 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...
+ HCl - CHCl3 + Cl2 → CCl4Carbon tetrachlorideCarbon tetrachloride, also known by many other names is the organic compound with the formula CCl4. It was formerly widely used in fire extinguishers, as a precursor to refrigerants, and as a cleaning agent...
+ HCl
The output of these processes is a mixture of methyl chloride, dichloromethane, 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 carbon tetrachloride
Carbon tetrachloride
Carbon tetrachloride, also known by many other names is the organic compound with the formula CCl4. It was formerly widely used in fire extinguishers, as a precursor to refrigerants, and as a cleaning agent...
. These compounds are separated by distillation
Distillation
Distillation is a method of separating mixtures based on differences in volatilities of components in a boiling liquid mixture. Distillation is a unit operation, or a physical separation process, and not a chemical reaction....
.
Uses
Dichloromethane's volatility and ability to dissolve a wide range of organic compounds makes it a useful solvent for many chemical processes. Concerns about its health effects have led to a search for alternatives in many of these applications.It is widely used as a paint stripper
Paint stripper
Paint stripper, or paint remover, is the generic name given to solvent mixtures designed to remove paint and other finishes and also to clean the underlying surface. The principal active ingredient is usually dichloromethane...
and a degreaser. In the food industry
Food industry
The food production is a complex, global collective of diverse businesses that together supply much of the food energy consumed by the world population...
, it has been used to decaffeinate
Decaffeination
Decaffeination is the act of removing caffeine from coffee beans, cocoa, tea leaves and other caffeine-containing materials. Despite removal of caffeine, many decaffeinated drinks still have around 1-2% of the...
coffee
Coffee
Coffee is a brewed beverage with a dark,init brooo acidic flavor prepared from the roasted seeds of the coffee plant, colloquially called coffee beans. The beans are found in coffee cherries, which grow on trees cultivated in over 70 countries, primarily in equatorial Latin America, Southeast Asia,...
and tea
Tea
Tea is an aromatic beverage prepared by adding cured leaves of the Camellia sinensis plant to hot water. The term also refers to the plant itself. After water, tea is the most widely consumed beverage in the world...
as well as to prepare extracts of hops
Hops
Hops are the female flower clusters , of a hop species, Humulus lupulus. They are used primarily as a flavoring and stability agent in beer, to which they impart a bitter, tangy flavor, though hops are also used for various purposes in other beverages and herbal medicine...
and other flavorings. Its volatility has led to its use as an aerosol spray propellant and as a 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...
for polyurethane
Polyurethane
A polyurethane is any polymer composed of a chain of organic units joined by carbamate links. Polyurethane polymers are formed through step-growth polymerization, by reacting a monomer with another monomer in the presence of a catalyst.Polyurethanes are...
foam
Foam
-Definition:A foam is a substance that is formed by trapping gas in a liquid or solid in a divided form, i.e. by forming gas regions inside liquid regions, leading to different kinds of dispersed media...
s.
Specialized uses
The chemical compound's low boiling pointBoiling point
The boiling point of an element or a substance is the temperature at which the vapor pressure of the liquid equals the environmental pressure surrounding the liquid....
allows the chemical to function as a heat engine
Heat engine
In thermodynamics, a heat engine is a system that performs the conversion of heat or thermal energy to mechanical work. It does this by bringing a working substance from a high temperature state to a lower temperature state. A heat "source" generates thermal energy that brings the working substance...
that can extract movement from low grade temperatures. An example of a Dichloromethane heat engine is the drinking bird
Drinking bird
Drinking birds, also known as dippy birds and dipping birds, are toy heat engines that mimic the motions of a bird drinking from a fountain or other water source. They are sometimes incorrectly considered examples of a perpetual motion device....
. The toy works at room temperature.
Dichloromethane chemically welds certain plastics; 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
Model building
Model building as a hobby involves the creation of models either from kits or from materials and components acquired by the builder.Categories of modelling include:*Scale model building*Live steam models*Matchstick models*Military models...
hobbyists for joining plastic components together — it is commonly referred to as "Di-clo."
It is also used in the garment printing industry for removal of heat-sealed garment transfers, and its volatility is exploited in novelty items — bubble light
Bubble light
A bubble light is a decorative device consisting of a liquid-filled vial that is heated and lighted by an incandescent light bulb. Because of the liquid's low boiling point, the modest heat generated by the lamp causes the liquid to boil and bubble up from the vial's base. The liquid is almost...
s and jukebox
Jukebox
A jukebox is a partially automated music-playing device, usually a coin-operated machine, that will play a patron's selection from self-contained media...
displays.
Dichloromethane is used within the material testing field of civil engineering
Civil engineering
Civil engineering is a professional engineering discipline that deals with the design, construction, and maintenance of the physical and naturally built environment, including works like roads, bridges, canals, dams, and buildings...
; specifically it is used during the testing of bituminous materials as a solvent to separate the binder from the aggregate of an asphalt
Asphalt
Asphalt or , also known as bitumen, is a sticky, black and highly viscous liquid or semi-solid that is present in most crude petroleums and in some natural deposits, it is a substance classed as a pitch...
or macadam
Macadam
Macadam is a type of road construction pioneered by the Scotsman John Loudon McAdam in around 1820. The method simplified what had been considered state-of-the-art at that point...
to allow the testing of the materials.
Toxicity
Dichloromethane is the least toxic of the simple chlorohydrocarbons, but it is not without its health risks as its high volatilityVolatility (chemistry)
In chemistry and physics, volatility is the tendency of a substance to vaporize. Volatility is directly related to a substance's vapor pressure. At a given temperature, a substance with higher vapor pressure vaporizes more readily than a substance with a lower vapor pressure.The term is primarily...
makes it an acute inhalation hazard. Dichloromethane is also metabolized by the body to carbon monoxide
Carbon monoxide
Carbon monoxide , also called carbonous oxide, is a colorless, odorless, and tasteless gas that is slightly lighter than air. It is highly toxic to humans and animals in higher quantities, although it is also produced in normal animal metabolism in low quantities, and is thought to have some normal...
potentially leading to carbon monoxide poisoning
Carbon monoxide poisoning
Carbon monoxide poisoning occurs after enough inhalation of carbon monoxide . Carbon monoxide is a toxic gas, but, being colorless, odorless, tasteless, and initially non-irritating, it is very difficult for people to detect...
. Acute exposure by inhalation has resulted in optic neuropathy
Optic neuropathy
The optic nerve contains axons of nerve cells that emerge from the retina, leave the eye at the optic disc, and go to the visual cortex where input from the eye is processed into vision. There are 1.2 million optic nerve fibers that derive from the retinal ganglion cells of the inner retina. Optic...
and hepatitis
Hepatitis
Hepatitis is a medical condition defined by the inflammation of the liver and characterized by the presence of inflammatory cells in the tissue of the organ. The name is from the Greek hepar , the root being hepat- , meaning liver, and suffix -itis, meaning "inflammation"...
. Prolonged skin contact can result in the dichloromethane dissolving some of the fatty tissues in skin, resulting in skin irritation or chemical burns.
It may be carcinogen
Carcinogen
A carcinogen is any substance, radionuclide, or radiation that is an agent directly involved in causing cancer. This may be due to the ability to damage the genome or to the disruption of cellular metabolic processes...
ic, as it has been linked to cancer
Cancer
Cancer , known medically as a malignant neoplasm, is a large group of different diseases, all involving unregulated cell growth. In cancer, cells divide and grow uncontrollably, forming malignant tumors, and invade nearby parts of the body. The cancer may also spread to more distant parts of the...
of the lungs, liver
Liver
The liver is a vital organ present in vertebrates and some other animals. It has a wide range of functions, including detoxification, protein synthesis, and production of biochemicals necessary for digestion...
, and pancreas
Pancreas
The pancreas is a gland organ in the digestive and endocrine system of vertebrates. It is both an endocrine gland producing several important hormones, including insulin, glucagon, and somatostatin, as well as a digestive organ, secreting pancreatic juice containing digestive enzymes that assist...
in laboratory animals. Dichloromethane crosses the placenta
Placenta
The placenta is an organ that connects the developing fetus to the uterine wall to allow nutrient uptake, waste elimination, and gas exchange via the mother's blood supply. "True" placentas are a defining characteristic of eutherian or "placental" mammals, but are also found in some snakes and...
. Fetal toxicity in women who are exposed to it 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...
, however, has not been proven. In animal experiments, it was fetotoxic at doses that were maternally toxic but no teratogenic
Teratology
Teratology is the study of abnormalities of physiological development. It is often thought of as the study of human birth defects, but it is much broader than that, taking in other non-birth developmental stages, including puberty; and other non-human life forms, including plants.- Etymology :The...
effects were seen.
In many countries, products containing dichloromethane must carry labels warning of its health risks.
In the European Union
European Union
The European Union is an economic and political union of 27 independent member states which are located primarily in Europe. The EU traces its origins from the European Coal and Steel Community and the European Economic Community , formed by six countries in 1958...
, the European Parliament
European Parliament
The European Parliament is the directly elected parliamentary institution of the European Union . Together with the Council of the European Union and the Commission, it exercises the legislative function of the EU and it has been described as one of the most powerful legislatures in the world...
voted in 2009 to ban the use of dichloromethane in paint-strippers for consumers and many professionals. The ban took effect in December 2010.
In Europe, the Scientific Committee on Occupational Exposure Limits (SCOEL) recommends for dichloromethane an occupational exposure limit
Occupational exposure limit
An occupational exposure limit is an upper limit on the acceptable concentration of a hazardous substance in workplace air for a particular material or class of materials. It is typically set by competent national authorities and enforced by legislation to protect occupational safety and health...
(8h time-weighted average) of 100 ppm and a short-term exposure limit (15 min) of 200 ppm.