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Chloroform

From Wikipedia, in a visual modern way
Chloroform
Chloroform displayed.svg
Chloroform-3D-balls.png
Chloroform in its liquid state shown in a test tube
Names
Preferred IUPAC name
Trichloromethane
Other names
Chloroform[1]
Methane trichloride
Methyl trichloride
Methenyl trichloride
Methenyl chloride
TCM
Freon 20
Refrigerant-20
R-20
UN 1888
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.603 Edit this at Wikidata
EC Number
  • 200-663-8
KEGG
RTECS number
  • FS9100000
UNII
  • InChI=1S/CHCl3/c2-1(3)4/h1H checkY
    Key: HEDRZPFGACZZDS-UHFFFAOYSA-N checkY
  • InChI=1/CHCl3/c2-1(3)4/h1H
    Key: HEDRZPFGACZZDS-UHFFFAOYAG
  • ClC(Cl)Cl
Properties
CHCl3
Molar mass 119.37 g·mol−1
Appearance Highly refractive colorless liquid
Odor Strong smell reminiscent of dry-cleaner's shops
Density 1.564 g/cm3 (−20 °C)
1.489 g/cm3 (25 °C)
1.394 g/cm3 (60 °C)
Melting point −63.5 °C (−82.3 °F; 209.7 K)
Boiling point 61.15 °C (142.07 °F; 334.30 K)
decomposes at 450 °C
10.62 g/L (0 °C)
8.09 g/L (20 °C)
7.32 g/L (60 °C)
Solubility Soluble in benzene
Miscible in diethyl ether, oils, ligroin, alcohol, CCl4, CS2
Solubility in acetone ≥ 100 g/L (19 °C)
Solubility in dimethyl sulfoxide ≥ 100 g/L (19 °C)
Vapor pressure 0.62 kPa (−40 °C)
7.89 kPa (0 °C)
25.9 kPa (25 °C)
313 kPa (100 °C)
2.26 MPa (200 °C)
3.67 L·atm/mol (24 °C)
Acidity (pKa) 15.7 (20 °C)
UV-vis (λmax) 250 nm, 260 nm, 280 nm
−59.30·10−6 cm3/mol
Thermal conductivity 0.13 W/m·K (20 °C)
1.4459 (20 °C)
Viscosity 0.563 cP (20 °C)
Structure
Tetrahedral
1.15 D
Thermochemistry
114.25 J/mol·K
202.9 J/mol·K
−134.3 kJ/mol
−71.1 kJ/mol
473.21 kJ/mol
Pharmacology
N01AB02 (WHO)
Hazards[7]
Occupational safety and health (OHS/OSH):
Main hazards
 Carcinogen – Reproductive toxicity – Specific target organ toxicity (STOT)[2][3][4]
GHS labelling:
GHS06: Toxic GHS08: Health hazard
Danger
H302, H315, H319, H331, H336, H351, H361d, H372
P201, P202, P235, P260, P264, P270, P271, P280, P281, P301+P330+P331, P302+P352, P304+P340, P305+P351+P338, P308+P313, P310, P311, P314, P332+P313, P337+P313, P362, P403+P233, P405, P501
NFPA 704 (fire diamond)
2
0
0
Flash point Non-flammable
Lethal dose or concentration (LD, LC):
704 mg/kg (mouse, dermal)[5]
9,617 ppm (rat, 4 hr)[6]
20,000 ppm (guinea pig, 2 hr)
7,056 ppm (cat, 4 hr)
25,000 ppm (human, 5 min)[6]
NIOSH (US health exposure limits):
PEL (Permissible)
 50 ppm (240 mg/m3)[3]
REL (Recommended)
 Ca ST 2 ppm (9.78 mg/m3) [60-minute][3]
IDLH (Immediate danger)
 500 ppm[3]
Safety data sheet (SDS) [1]
Related compounds
Related chloromethanes
 Chloromethane
Dichloromethane
Tetrachloromethane
Supplementary data page
Chloroform (data page)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
For other uses, see Chloroform (disambiguation).

Chloroform, or trichloromethane (often abbreviated as TCM), is an organic compound with the formula CHCl3 and a common organic solvent. It is a very volatile, colorless, strong-smelling, dense liquid produced on a large scale as a precursor to PTFE and refrigerants[8] and is a trihalomethane that serves as a powerful anesthetic, euphoriant, anxiolytic, and sedative when inhaled or ingested. It is also part of a wider class of substances known as volatile organic compounds.[9][10]

Chloroform is miscible with many solvents but it is only very slightly soluble in water (only 8 g/L at 20 °C). Chloroform was frequently used as an anaesthetic between 1847 and the first half of the 20th century.

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Organic compound

Organic compound

In chemistry, many authors consider an organic compound to be any chemical compound that contains carbon-hydrogen or carbon-carbon bonds, although the definition of "organic" versus "inorganic" varies from author to author, and is a topic of debate. For example, methane is considered organic, but whether halides of carbon without hydrogen are organic or inorganic varies from author to author.

Chemical formula

Chemical formula

In chemistry, a chemical formula is a way of presenting information about the chemical proportions of atoms that constitute a particular chemical compound or molecule, using chemical element symbols, numbers, and sometimes also other symbols, such as parentheses, dashes, brackets, commas and plus (+) and minus (−) signs. These are limited to a single typographic line of symbols, which may include subscripts and superscripts. A chemical formula is not a chemical name, and it contains no words. Although a chemical formula may imply certain simple chemical structures, it is not the same as a full chemical structural formula. Chemical formulae can fully specify the structure of only the simplest of molecules and chemical substances, and are generally more limited in power than chemical names and structural formulae.

Carbon

Carbon

Carbon is a chemical element with the symbol C and atomic number 6. It is nonmetallic and tetravalent—its atom making four electrons available to form covalent chemical bonds. It belongs to group 14 of the periodic table. Carbon makes up about 0.025 percent of Earth's crust. Three isotopes occur naturally, 12C and 13C being stable, while 14C is a radionuclide, decaying with a half-life of about 5,730 years. Carbon is one of the few elements known since antiquity.

Hydrogen

Hydrogen

Hydrogen is the chemical element with the symbol H and atomic number 1. Hydrogen is the lightest element. At standard conditions hydrogen is a gas of diatomic molecules having the formula H2. It is colorless, odorless, tasteless, non-toxic, and highly combustible. Hydrogen is the most abundant chemical substance in the universe, constituting roughly 75% of all normal matter. Stars such as the Sun are mainly composed of hydrogen in the plasma state. Most of the hydrogen on Earth exists in molecular forms such as water and organic compounds. For the most common isotope of hydrogen each atom has one proton, one electron, and no neutrons.

Chlorine

Chlorine

Chlorine is a chemical element with the 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 between them. Chlorine is a yellow-green gas at room temperature. It is an extremely reactive element and a strong oxidising agent: among the elements, it has the highest electron affinity and the third-highest electronegativity on the revised Pauling scale, behind only oxygen and fluorine.

Solvent

Solvent

A solvent is a substance that dissolves a solute, resulting in a solution. A solvent is usually a liquid but can also be a solid, a gas, or a supercritical fluid. Water is a solvent for polar molecules and the most common solvent used by living things; all the ions and proteins in a cell are dissolved in water within the cell.

Refrigerant

Refrigerant

A refrigerant is a working fluid used in the 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. Refrigerants are heavily regulated due to their toxicity, flammability and the contribution of CFC and HCFC refrigerants to ozone depletion and that of HFC refrigerants to climate change.

Trihalomethane

Trihalomethane

In chemistry, trihalomethanes (THMs) are chemical compounds in which three of the four hydrogen atoms of methane are replaced by halogen atoms. Many trihalomethanes find uses in industry as solvents or refrigerants. THMs are also environmental pollutants, and many are considered carcinogenic. Trihalomethanes with all the same halogen atoms are called haloforms.

Anesthetic

Anesthetic

An anesthetic or anaesthetic is a drug used to induce anesthesia ⁠— ⁠in other words, to result in a temporary loss of sensation or awareness. They may be divided into two broad classes: general anesthetics, which result in a reversible loss of consciousness, and local anesthetics, which cause a reversible loss of sensation for a limited region of the body without necessarily affecting consciousness.

Anxiolytic

Anxiolytic

An anxiolytic is a medication or other intervention that reduces anxiety. This effect is in contrast to anxiogenic agents which increase anxiety. Anxiolytic medications are used for the treatment of anxiety disorders and their related psychological and physical symptoms.

Sedative

Sedative

A sedative or tranquilliser is a substance that induces sedation by reducing irritability or excitement. They are CNS depressants and interact with brain activity causing its deceleration. Various kinds of sedatives can be distinguished, but the majority of them affect the neurotransmitter gamma-aminobutyric acid (GABA). In spite of the fact that each sedative acts in its own way, most produce relaxing effects by increasing GABA activity.

Structure

The molecule adopts a tetrahedral molecular geometry with C3v symmetry.[11] The chloroform molecule can be viewed as a methane molecule with three hydrogen atoms replaced with three chlorine atoms, leaving a single hydrogen atom.

Natural occurrence

The total global flux of chloroform through the environment is approximately 660000 tonnes per year,[12] and about 90% of emissions are natural in origin. Many kinds of seaweed produce chloroform, and fungi are believed to produce chloroform in soil.[13] Abiotic processes are also believed to contribute to natural chloroform productions in soils, although the mechanism is still unclear.[14]

As chloroform is a volatile organic compound,[15] it dissipates readily from soil and surface water and undergoes degradation in air to produce phosgene, dichloromethane, formyl chloride, carbon monoxide, carbon dioxide, and hydrogen chloride. 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.[16]

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Seaweed

Seaweed

Seaweed, or macroalgae, refers to thousands of species of macroscopic, multicellular, marine algae. The term includes some types of Rhodophyta (red), Phaeophyta (brown) and Chlorophyta (green) macroalgae. Seaweed species such as kelps provide essential nursery habitat for fisheries and other marine species and thus protect food sources; other species, such as planktonic algae, play a vital role in capturing carbon, producing at least 50% of Earth's oxygen.

Phosgene

Phosgene

Phosgene is the organic chemical compound with the formula COCl2. It is a toxic, colorless gas; in low concentrations, its musty odor resembles that of freshly cut hay or grass. It can be thought of as formaldehyde with the hydrogen atoms replaced by chlorine atoms. Phosgene is a valued and important industrial building block, especially for the production of precursors of polyurethanes and polycarbonate plastics.

Dichloromethane

Dichloromethane

Dichloromethane is an organochlorine compound with the formula CH2Cl2. This colorless, volatile liquid with a chloroform-like, sweet odour is widely used as a solvent. Although it is not miscible with water, it is slightly polar, and miscible with many organic solvents.

Carbon monoxide

Carbon monoxide

Carbon monoxide is a poisonous, flammable gas that is colorless, odorless, tasteless, and slightly less dense than air. Carbon monoxide consists of one carbon atom and one oxygen atom connected by a triple bond. It is the simplest carbon oxide. In coordination complexes the carbon monoxide ligand is called carbonyl. It is a key ingredient in many processes in industrial chemistry.

Carbon dioxide

Carbon dioxide

Carbon dioxide (chemical formula CO2) is a chemical compound made up of molecules that each have one carbon atom covalently double bonded to two oxygen atoms. It is found in the gas state at room temperature, and as the source of available carbon in the carbon cycle, atmospheric CO2 is the primary carbon source for life on Earth. In the air, carbon dioxide is transparent to visible light but absorbs infrared radiation, acting as a greenhouse gas. Carbon dioxide is soluble in water and is found in groundwater, lakes, ice caps, and seawater. When carbon dioxide dissolves in water, it forms carbonate and mainly bicarbonate (HCO−3), which causes ocean acidification as atmospheric CO2 levels increase.

Hydrogen chloride

Hydrogen chloride

The compound hydrogen chloride has the chemical formula HCl 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 gas and hydrochloric acid are important in technology and industry. Hydrochloric acid, the aqueous solution of hydrogen chloride, is also commonly given the formula HCl.

Half-life

Half-life

Half-life is the time required for a quantity to reduce to half of its initial value. The term is commonly used in nuclear physics to describe how quickly unstable atoms undergo radioactive decay or how long stable atoms survive. The term is also used more generally to characterize any type of exponential decay. For example, the medical sciences refer to the biological half-life of drugs and other chemicals in the human body. The converse of half-life is doubling time.

Biodegradation

Biodegradation

Biodegradation is the breakdown of organic matter by microorganisms, such as bacteria and fungi. It is generally assumed to be a natural process, which differentiates it from composting. Composting is a human-driven process in which biodegradation occurs under a specific set of circumstances.

History

Chloroform was synthesized independently by several investigators circa 1831:

  • Moldenhawer, a German pharmacist from Frankfurt an der Oder, appears to have produced chloroform in 1830 by mixing chlorinated lime with ethanol; however, he mistook it for Chloräther (chloric ether, 1,2-dichloroethane).[17][18]
  • Samuel Guthrie, a U.S. physician from Sackets Harbor, New York, also appears to have produced chloroform in 1831 by reacting chlorinated lime with ethanol, as well as noting its anaesthetic properties; he also believed that he had prepared chloric ether, however.[19][20][21]
  • Justus von Liebig carried out the alkaline cleavage of chloral. Liebig incorrectly states that the empirical formula of chloroform is C2Cl5 and names it "Chlorkohlenstoff" ("carbon chloride").[22][23]
  • Eugène Soubeiran obtained the compound by the action of chlorine bleach on both ethanol and acetone.[24]
  • In 1834, French chemist Jean-Baptiste Dumas determined chloroform's empirical formula and named it.[25] Dumas states chloroform's empirical formula and names it: "Es scheint mir also erweisen, dass die von mir analysirte Substance, … zur Formel hat: C2H2Cl6." (Thus it seems to me to show that the substance [that was] analyzed by me … has as [its empirical] formula: C2H2Cl6.) [Note: The coefficients of his empirical formula must be halved.] ... "Diess hat mich veranlasst diese Substanz mit dem Namen 'Chloroform' zu belegen." (This caused me to bestow this substance with the name "chloroform" [i.e., formyl chloride or chloride of formic acid].)
  • In 1835, Dumas prepared the substance by the alkaline cleavage of trichloroacetic acid.
  • Regnault prepared chloroform by chlorination of chloromethane.
  • In 1842, Robert Mortimer Glover in London discovered the anaesthetic qualities of chloroform on laboratory animals.[26]
  • In 1847, Scottish obstetrician James Y. Simpson was the first to demonstrate the anaesthetic properties of chloroform on humans, provided by local pharmacist William Flockhart of Duncan, Flockhart and company,[27] and helped to popularise the drug for use in medicine.[28]
  • By the 1850s, chloroform was being produced on a commercial basis. In Britain, about 750,000 doses a week were being produced by 1895[29] using the Liebig procedure, which retained its importance until the 1960s. Today, chloroform – along with dichloromethane – is prepared exclusively and on a massive scale by the chlorination of methane and chloromethane.[8]

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Ethanol

Ethanol

Ethanol is an organic compound. It is an alcohol with the chemical formula C2H6O. Its formula can also be written as CH3−CH2−OH or C2H5OH. Ethanol is a volatile, flammable, colorless liquid with a characteristic wine-like odor and pungent taste. It is a psychoactive recreational drug, and the active ingredient in alcoholic drinks.

Anesthetic

Anesthetic

An anesthetic or anaesthetic is a drug used to induce anesthesia ⁠— ⁠in other words, to result in a temporary loss of sensation or awareness. They may be divided into two broad classes: general anesthetics, which result in a reversible loss of consciousness, and local anesthetics, which cause a reversible loss of sensation for a limited region of the body without necessarily affecting consciousness.

Justus von Liebig

Justus von Liebig

Justus Freiherr von Liebig was a German scientist who made major contributions to agricultural and biological chemistry, and is considered one of the principal founders of organic chemistry. As a professor at the University of Giessen, he devised the modern laboratory-oriented teaching method, and for such innovations, he is regarded as one of the greatest chemistry teachers of all time. He has been described as the "father of the fertilizer industry" for his emphasis on nitrogen and trace minerals as essential plant nutrients, and his formulation of the law of the minimum, which described how plant growth relied on the scarcest nutrient resource, rather than the total amount of resources available. He also developed a manufacturing process for beef extracts, and with his consent a company, called Liebig Extract of Meat Company, was founded to exploit the concept; it later introduced the Oxo brand beef bouillon cube. He popularized an earlier invention for condensing vapors, which came to be known as the Liebig condenser.

Bond cleavage

Bond cleavage

In chemistry, bond cleavage, or bond fission, is the splitting of chemical bonds. This can be generally referred to as dissociation when a molecule is cleaved into two or more fragments.

Chloral

Chloral

Chloral, also known as trichloroacetaldehyde or trichloroethanal, is the organic compound with the formula Cl3CCHO. This aldehyde is a colourless oily liquid that is soluble in a wide range of solvents. It reacts with water to form chloral hydrate, a once widely used sedative and hypnotic substance.

Empirical formula

Empirical formula

In chemistry, the empirical formula of a chemical compound is the simplest whole number ratio of atoms present in a compound. A simple example of this concept is that the empirical formula of sulfur monoxide, or SO, would simply be SO, as is the empirical formula of disulfur dioxide, S2O2. Thus, sulfur monoxide and disulfur dioxide, both compounds of sulfur and oxygen, have the same empirical formula. However, their molecular formulas, which express the number of atoms in each molecule of a chemical compound, are not the same.

Eugène Soubeiran

Eugène Soubeiran

Eugène Soubeiran was a French scientist.

Acetone

Acetone

Acetone, is an organic compound with the formula (CH3)2CO. It is the simplest and smallest ketone. It is a colorless, highly volatile and flammable liquid with a characteristic pungent odor.

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. He also developed a method for the analysis of nitrogen in compounds.

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. He never used his first given name, and was known throughout his lifetime as Victor Regnault.

Halogenation

Halogenation

In chemistry, halogenation is a chemical reaction that entails the introduction of one or more halogens into a compound. Halide-containing compounds are pervasive, making this type of transformation important, e.g. in the production of polymers, drugs. This kind of conversion is in fact so common that a comprehensive overview is challenging. This article mainly deals with halogenation using elemental halogens (F2, Cl2, Br2, I2). Halides are also commonly introduced using salts of the halides and halogen acids. Many specialized reagents exist for and introducing halogens into diverse substrates, e.g. thionyl chloride.

Chloromethane

Chloromethane

Chloromethane, also called methyl chloride, Refrigerant-40, R-40 or HCC 40, is an organic compound with the chemical formula CH3Cl. One of the haloalkanes, it is a colorless, odorless, flammable gas. Methyl chloride is a crucial reagent in industrial chemistry, although it is rarely present in consumer products, and was formerly utilized as a refrigerant.

Production

Industrially, chloroform is produced by heating a mixture of chlorine and either methyl chloride (CH3Cl) or methane (CH4).[8] At 400–500 °C, a free radical halogenation occurs, converting these precursors to progressively more chlorinated compounds:

CH4 + Cl2 → CH3Cl + HCl
CH3Cl + Cl2 → CH2Cl2 + HCl
CH2Cl2 + Cl2 → CHCl3 + HCl

Chloroform undergoes further chlorination to yield carbon tetrachloride (CCl4):

CHCl3 + Cl2 → CCl4 + HCl

The output of this process is a mixture of the four chloromethanes: chloromethane, methylene chloride (dichloromethane), trichloromethane (chloroform), and tetrachloromethane (carbon tetrachloride). This can then be separated by distillation.[8]

Chloroform may also be produced on a small scale via the haloform reaction between acetone and sodium hypochlorite:

3 NaClO + (CH3)2CO → CHCl3 + 2 NaOH + CH3COONa

Deuterochloroform

Main article: Deuterated chloroform

Deuterated chloroform is an isotopologue of chloroform with a single deuterium atom. CDCl3 is a common solvent used in NMR spectroscopy. Deuterochloroform is produced by the reaction of hexachloroacetone with deuterium oxide.[30] 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.[31][32]

Inadvertent formation of 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.[33] Sodium hypochlorite solution (chlorine bleach) mixed with common household liquids such as acetone, methyl ethyl ketone, ethanol, or isopropyl alcohol can produce some chloroform, in addition to other compounds such as chloroacetone or dichloroacetone.

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Chlorine

Chlorine

Chlorine is a chemical element with the 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 between them. Chlorine is a yellow-green gas at room temperature. It is an extremely reactive element and a strong oxidising agent: among the elements, it has the highest electron affinity and the third-highest electronegativity on the revised Pauling scale, behind only oxygen and fluorine.

Methane

Methane

Methane is a chemical compound with the chemical formula CH4. It is a group-14 hydride, the simplest alkane, and the main constituent of natural gas. The relative abundance of methane on Earth makes it an economically attractive fuel, although capturing and storing it poses technical challenges due to its gaseous state under normal conditions for temperature and pressure.

Hydrogen chloride

Hydrogen chloride

The compound hydrogen chloride has the chemical formula HCl 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 gas and hydrochloric acid are important in technology and industry. Hydrochloric acid, the aqueous solution of hydrogen chloride, is also commonly given the formula HCl.

Carbon tetrachloride

Carbon tetrachloride

Carbon tetrachloride, also known by many other names (such as tetrachloromethane, also recognised by the IUPAC, carbon tet in the cleaning industry, Halon-104 in firefighting, and Refrigerant-10 in HVACR) is a chemical compound with the chemical formula CCl4. It is a colourless liquid with a "sweet" smell that can be detected at low levels. It is practically incombustible at lower temperatures. It was formerly widely used in fire extinguishers, as a precursor to refrigerants and as a cleaning agent, but has since been phased out because of environmental and safety concerns. Exposure to high concentrations of carbon tetrachloride (including vapor) can affect the central nervous system and degenerate the liver and kidneys. Prolonged exposure can be fatal.

Chloromethane

Chloromethane

Chloromethane, also called methyl chloride, Refrigerant-40, R-40 or HCC 40, is an organic compound with the chemical formula CH3Cl. One of the haloalkanes, it is a colorless, odorless, flammable gas. Methyl chloride is a crucial reagent in industrial chemistry, although it is rarely present in consumer products, and was formerly utilized as a refrigerant.

Distillation

Distillation

Distillation, or classical distillation, is the process of separating the components or substances from a liquid mixture by using selective boiling and condensation, usually inside an apparatus known as a still. Dry distillation is the heating of solid materials to produce gaseous products ; this may involve chemical changes such as destructive distillation or cracking. Distillation may result in essentially complete separation, or it may be a partial separation that increases the concentration of selected components; in either case, the process exploits differences in the relative volatility of the mixture's components. In industrial applications, distillation is a unit operation of practically universal importance, but is a physical separation process, not a chemical reaction. An installation used for distillation, especially of distilled beverages, is a distillery. Distillation includes the following applications:The distillation of fermented products produces distilled beverages with a high alcohol content, or separates other fermentation products of commercial value. Distillation is an effective and traditional method of desalination. In the petroleum industry, oil stabilization is a form of partial distillation that reduces the vapor pressure of crude oil, thereby making it safe for storage and transport as well as reducing the atmospheric emissions of volatile hydrocarbons. In midstream operations at oil refineries, fractional distillation is a major class of operation for transforming crude oil into fuels and chemical feed stocks. Cryogenic distillation leads to the separation of air into its components – notably oxygen, nitrogen, and argon – for industrial use. In the chemical industry, large amounts of crude liquid products of chemical synthesis are distilled to separate them, either from other products, from impurities, or from unreacted starting materials.

Haloform reaction

Haloform reaction

In chemistry, the haloform reaction is a chemical reaction in which a haloform is produced by the exhaustive halogenation of an acetyl group, in the presence of a base. The reaction can be used to transform acetyl groups into carboxyl groups or to produce chloroform, bromoform, or iodoform. Note that fluoroform can't be prepared in this way.

Acetone

Acetone

Acetone, is an organic compound with the formula (CH3)2CO. It is the simplest and smallest ketone. It is a colorless, highly volatile and flammable liquid with a characteristic pungent odor.

Deuterated chloroform

Deuterated chloroform

Deuterated chloroform, also known as chloroform-d, is the organic compound with the formula C2HCl3 or CDCl3. Deuterated chloroform is a common solvent used in NMR spectroscopy. The properties of CDCl3 and ordinary CHCl3 (chloroform) are virtually identical.

Isotopologue

Isotopologue

In chemistry, isotopologues are molecules that differ only in their isotopic composition. They have the same chemical formula and bonding arrangement of atoms, but at least one atom has a different number of neutrons than the parent.

Deuterium

Deuterium

Deuterium is one of two stable isotopes of hydrogen. The nucleus of a deuterium atom, called a deuteron, contains one proton and one neutron, whereas the far more common protium has no neutrons in the nucleus. Deuterium has a natural abundance in Earth's oceans of about one atom of deuterium among every 6,420 atoms of hydrogen. Thus deuterium accounts for approximately 0.0156% by number of all the naturally occurring hydrogen in the oceans, while protium accounts for more than 99.98%. The abundance of deuterium changes slightly from one kind of natural water to another.

Hexachloroacetone

Hexachloroacetone

Hexachloroacetone is an organic compound with the formula (Cl3C)2CO. It is also called hexachloropropanone or perchloroacetone. Numbers indicating the position of the chlorine-atoms are generally omitted as all the possible positions are substituted with chlorine. It is a colorless liquid, slightly soluble in water.

Uses

In terms of scale, the most important reaction of chloroform is with hydrogen fluoride to give monochlorodifluoromethane (CFC-22), a precursor in the production of polytetrafluoroethylene (Teflon) and other fluoropolymers:[8]

CHCl3 + 2HF → CHClF2 + 2 HCl

The reaction is conducted in the presence of a catalytic amount of mixed antimony halides. Chlorodifluoromethane is then converted into tetrafluoroethylene, the main precursor to Teflon.[34]

Solvent

The hydrogen attached to carbon in chloroform participates in hydrogen bonding,[35][36] thus making it a good solvent for many materials.

Worldwide, chloroform is also used in pesticide formulations, as a solvent for lipids, rubber, alkaloids, waxes, gutta-percha, and resins, as a cleansing agent, grain fumigant, in fire extinguishers, and in the rubber industry.[16][37] CDCl3 is a common solvent used in NMR spectroscopy.[38]

Refrigerant

Trichloromethane has been used as a precursor to make R-22 (Chlorodifluoromethane). This is done by reacting it with a solution of Hydrofluoric acid (HF) which will fluorinate the CHCl3 molecule and release hydrochloric acid as a byproduct.[39] Prior to the enforcement of the Montreal Protocol, the majority of the trichloromethane produced in the United States, was used for the production of Chlorodifluoromethane. [40]

Although trichloromethane has properties such as its low boiling point and its low global warming potential of only 31 (compared to the 1,760 of R-22) which result in it having good refrigeration properties, there is little information to suggest that it has seen widespread use as a refrigerant in any consumer products.[41]

Lewis acid

In solvents such as CCl4 and alkanes, chloroform hydrogen bonds to a variety of Lewis bases. HCCl3 is classified as a hard acid and the ECW model lists its acid parameters as EA = 1.56 and CA = 0.44.

Reagent

As a reagent, chloroform serves as a source of the dichlorocarbene :CCl2 group.[42] It reacts with aqueous sodium hydroxide usually in the presence of a phase transfer catalyst to produce dichlorocarbene, :CCl2.[43][44] This reagent effects ortho-formylation of activated aromatic rings such as phenols, producing aryl aldehydes in a reaction known as the Reimer–Tiemann reaction. Alternatively, the carbene can be trapped by an alkene to form a cyclopropane derivative. In the Kharasch addition, chloroform forms the CHCl2 free radical in addition to alkenes.

Anaesthetic

Antique bottles of chloroform
Antique bottles of chloroform

The anaesthetic qualities of chloroform were first described in 1842 in a thesis by Robert Mortimer Glover, which won the Gold Medal of the Harveian Society for that year. Glover also undertook practical experiments on dogs to prove his theories, and refined his theories and presented them in the thesis for his doctorate at the University of Edinburgh in the summer of 1847.

The Scottish obstetrician James Young Simpson was one of the persons required to read the thesis, but later claimed to have never read the thesis and to have come to his own conclusions independently. On 4 November 1847, Simpson argued that he discovered the anaesthetic qualities of chloroform on humans. He and two colleagues entertained themselves by trying the effects of various substances, and thus revealed the potential for chloroform in medical procedures.[27]

A few days later, during the course of a dental procedure in Edinburgh, Francis Brodie Imlach became the first person to use chloroform on a patient in a clinical context.[45]

In May 1848, Robert Halliday Gunning made a presentation to the Medico-Chirurgical Society of Edinburgh following a series of laboratory experiments on rabbits that confirmed Glover's findings and also refuted Simpson's claims of originality. The laboratory experiments proving the dangers of chloroform were largely ignored.[46]

The use of chloroform during surgery expanded rapidly in Europe; for instance in the 1850s, chloroform was used by the physician John Snow during the birth of Queen Victoria's last two children.[47] In the United States, chloroform began to replace ether as an anesthetic at the beginning of the 20th century; it was abandoned in favor of ether upon discovery of its toxicity, especially its tendency to cause fatal cardiac arrhythmia analogous to what is now termed "sudden sniffer's death". Some people used chloroform as a recreational drug or to attempt suicide.[48] One possible mechanism of action for chloroform is that it increases the movement of potassium ions through certain types of potassium channels in nerve cells.[49] Chloroform could also be mixed with other anaesthetic agents such as ether to make C.E. mixture, or ether and alcohol to make A.C.E. mixture.

In 1848, Hannah Greener, a 15-year-old girl who was having an infected toenail removed, died after being given the anaesthetic.[50] Her autopsy establishing the cause of death was undertaken by John Fife assisted by Robert Mortimer Glover.[26] A number of physically fit patients died after inhaling it. In 1848, however, John Snow developed an inhaler that regulated the dosage and so successfully reduced the number of deaths.[51]

The opponents and supporters of chloroform disagreed on the question of whether the medical complications were due to respiratory disturbance or whether chloroform had a specific effect on the heart. Between 1864 and 1910, numerous commissions in Britain studied chloroform but failed to come to any clear conclusions. It was only in 1911 that Levy proved in experiments with animals that chloroform can cause cardiac fibrillation. Despite this, between 1865 and 1920, chloroform was used in 80 to 95% of all narcoses performed in the UK and German-speaking countries. IIn Germany, the first comprehensive surveys of the fatality rate during anaesthesia were made by Gurlt between 1890 and 1897. In 1934, Killian gathered all the statistics compiled until then and found that the chances of suffering fatal complications under ether were between 1:14,000 and 1:28,000, whereas under chloroform the chances were between 1:3,000 and 1:6,000. The rise of gas anaesthesia using nitrous oxide, improved equipment for administering anaesthetics and the discovery of hexobarbital in 1932 led to the gradual decline of chloroform narcosis.[52]

Criminal use

Chloroform has been used by criminals to knock out, daze, or even murder victims. Joseph Harris was charged in 1894 with using chloroform to rob people.[53] Serial killer H. H. Holmes used chloroform overdoses to kill his female victims. In September 1900, chloroform was implicated in the murder of the U.S. businessman William Marsh Rice. Chloroform was deemed a factor in the alleged murder of a woman in 1991 when she was asphyxiated while sleeping.[54] In 2002, 13-year-old Kacie Woody was sedated with chloroform when she was abducted by David Fuller and during the time that he had her, before he shot and killed her.[55] In a 2007 plea bargain, a man confessed to using stun guns and chloroform to sexually assault minors.[56]

Use of chloroform as an incapacitating agent has become widely recognized, bordering on clichéd, due to the popularity of crime fiction authors having criminals use chloroform-soaked rags to render victims unconscious. However, it is nearly impossible to incapacitate someone using chloroform in this manner.[57] It takes at least five minutes of inhaling an item soaked in chloroform to render a person unconscious. Most criminal cases involving chloroform also involve another drug being co-administered, such as alcohol or diazepam, or the victim being found to have been complicit in its administration. After a person has lost consciousness due to chloroform inhalation, a continuous volume must be administered, and the chin must be supported to keep the tongue from obstructing the airway, a difficult procedure typically requiring the skills of an anesthesiologist. In 1865 as a direct result of the criminal reputation chloroform had gained, the medical journal The Lancet offered a "permanent scientific reputation" to anyone who could demonstrate "instantaneous insensibility", i.e. losing consciousness instantaneously, using chloroform.[58]

Discover more about Uses related topics

Hydrogen fluoride

Hydrogen fluoride

Hydrogen fluoride (fluorane) is an inorganic compound with the chemical formula HF. This colorless gas or liquid is the principal industrial source of fluorine, often as an aqueous solution called hydrofluoric acid. It is an important feedstock in the preparation of many important compounds including pharmaceuticals and polymers, e.g. polytetrafluoroethylene (PTFE). HF is widely used in the petrochemical industry as a component of superacids. Hydrogen fluoride boils at near room temperature, much higher than other hydrogen halides.

Catalysis

Catalysis

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 recycles quickly, very small amounts of catalyst often suffice; mixing, surface area, and temperature are important factors in reaction rate. Catalysts generally react with one or more reactants to form intermediates that subsequently give the final reaction product, in the process of regenerating the catalyst.

Tetrafluoroethylene

Tetrafluoroethylene

Tetrafluoroethylene (TFE) is a fluorocarbon with the chemical formula C2F4. It is the simplest perfluorinated alkene. This gaseous species is used primarily in the industrial preparation of fluoropolymers.

Hydrogen

Hydrogen

Hydrogen is the chemical element with the symbol H and atomic number 1. Hydrogen is the lightest element. At standard conditions hydrogen is a gas of diatomic molecules having the formula H2. It is colorless, odorless, tasteless, non-toxic, and highly combustible. Hydrogen is the most abundant chemical substance in the universe, constituting roughly 75% of all normal matter. Stars such as the Sun are mainly composed of hydrogen in the plasma state. Most of the hydrogen on Earth exists in molecular forms such as water and organic compounds. For the most common isotope of hydrogen each atom has one proton, one electron, and no neutrons.

Carbon

Carbon

Carbon is a chemical element with the symbol C and atomic number 6. It is nonmetallic and tetravalent—its atom making four electrons available to form covalent chemical bonds. It belongs to group 14 of the periodic table. Carbon makes up about 0.025 percent of Earth's crust. Three isotopes occur naturally, 12C and 13C being stable, while 14C is a radionuclide, decaying with a half-life of about 5,730 years. Carbon is one of the few elements known since antiquity.

Solvent

Solvent

A solvent is a substance that dissolves a solute, resulting in a solution. A solvent is usually a liquid but can also be a solid, a gas, or a supercritical fluid. Water is a solvent for polar molecules and the most common solvent used by living things; all the ions and proteins in a cell are dissolved in water within the cell.

Alkaloid

Alkaloid

Alkaloids are a class of basic, naturally occurring organic compounds that contain at least one nitrogen atom. This group also includes some related compounds with neutral and even weakly acidic properties. Some synthetic compounds of similar structure may also be termed alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and, more rarely, other elements such as chlorine, bromine, and phosphorus.

Wax

Wax

Waxes are a diverse class of organic compounds that are lipophilic, malleable solids near ambient temperatures. They include higher alkanes and lipids, typically with melting points above about 40 °C (104 °F), melting to give low viscosity liquids. Waxes are insoluble in water but soluble in nonpolar organic solvents such as hexane, benzene and chloroform. Natural waxes of different types are produced by plants and animals and occur in petroleum.

Gutta-percha

Gutta-percha

Gutta-percha is a tree of the genus Palaquium in the family Sapotaceae. The name also refers to the rigid, naturally biologically inert, resilient, electrically nonconductive, thermoplastic latex derived from the tree, particularly from Palaquium gutta; it is a polymer of isoprene which forms a rubber-like elastomer.

Resin

Resin

In polymer chemistry and materials science, a 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 naturally occurring resins.

Deuterated chloroform

Deuterated chloroform

Deuterated chloroform, also known as chloroform-d, is the organic compound with the formula C2HCl3 or CDCl3. Deuterated chloroform is a common solvent used in NMR spectroscopy. The properties of CDCl3 and ordinary CHCl3 (chloroform) are virtually identical.

Safety

Exposure

Chloroform is known to form as a by-product of water chlorination, along with a range of other disinfection by-products, and as such is commonly present in municipal tap water and swimming pools. Reported ranges vary considerably but are generally below the current health standard for total trihalomethanes of 100μg/L.[59] Nonetheless, the presence of chloroform in drinking water at any concentration is considered controversial by some.

Historically, chloroform exposure may well have been higher due to its common use as an anaesthetic, as an ingredient in cough syrups, and as a constituent of tobacco smoke where DDT had previously been used as a fumigant.[60]

Pharmacology

It is well absorbed, metabolized, and eliminated rapidly by mammals after oral, inhalation, or dermal exposure. Accidental splashing into the eyes has caused irritation.[16] Prolonged dermal exposure can result in the development of sores as a result of defatting. Elimination is primarily through the lungs in the form of chloroform and carbon dioxide; less than 1% is excreted in the urine.[37]

Chloroform is metabolized in the liver by the cytochrome P-450 enzymes, by oxidation to chloromethanol and by reduction to the dichloromethyl free radical. Other metabolites of chloroform include hydrochloric acid and digluathionyl dithiocarbonate, with carbon dioxide as the predominant end product of metabolism.[61]

Like most other general anesthetics and sedative-hypnotic drugs, chloroform is a positive allosteric modulator for the GABAA receptor.[62] Chloroform causes depression of the central nervous system (CNS), ultimately producing deep coma and respiratory center depression.[61] When ingested, chloroform caused symptoms similar to those seen following inhalation. Serious illness has followed ingestion of 7.5 g (0.26 oz). The mean lethal oral dose for an adult is estimated at 45 g (1.6 oz).[16]

The anesthetic use of chloroform has been discontinued because it caused deaths due to respiratory failure and cardiac arrhythmias. Following chloroform-induced anesthesia, some patients suffered nausea, vomiting, hyperthermia, jaundice, and coma due to hepatic dysfunction. At autopsy, liver necrosis and degeneration have been observed.[16]

Chloroform has induced liver tumors in mice and kidney tumors in mice and rats.[16] The hepatotoxicity and nephrotoxicity of chloroform is thought to be due largely to phosgene.[61]

Conversion to phosgene

Chloroform converts slowly in air to the extremely poisonous phosgene (COCl2), releasing HCl in the process.[63]

2 CHCl3 + O2 → 2 COCl2 + 2 HCl

To prevent accidents, commercial chloroform is stabilized with ethanol or amylene, but samples that have been recovered or dried no longer contain any stabilizer. Amylene has been found ineffective, and the phosgene can affect analytes in samples, lipids, and nucleic acids dissolved in or extracted with chloroform.[64] Phosgene and HCl can be removed from chloroform by washing with saturated aqueous carbonate solutions, such as sodium bicarbonate. This procedure is simple and results in harmless products. Phosgene reacts with water to form carbon dioxide and HCl,[65] and the carbonate salt neutralizes the resulting acid.[66]

Suspected samples can be tested for phosgene using filter paper (treated with 5% diphenylamine, 5% dimethylaminobenzaldehyde in ethanol, and then dried), which turns yellow in phosgene vapour. There are several colorimetric and fluorometric reagents for phosgene, and it can also be quantified with mass spectrometry.[67]

Regulation

Chloroform is suspected of causing cancer (i.e., possibly carcinogenic, IARC Group 2B) as per the International Agency for Research on Cancer (IARC) Monographs. [PDF]

It is classified as an extremely hazardous substance in the United States as defined in Section 302 of the U.S. Emergency Planning and Community Right-to-Know Act (42 U.S.C. 11002), and is subject to strict reporting requirements by facilities that produce, store, or use it in significant quantities.[68]

Discover more about Safety related topics

Disinfection by-product

Disinfection by-product

Disinfection by-products (DBPs) result from chemical reactions between organic and inorganic matter in water with chemical treatment agents during the water disinfection process.

DDT

DDT

Dichlorodiphenyltrichloroethane, commonly known as DDT, is a colorless, tasteless, and almost odorless crystalline chemical compound, an organochloride. Originally developed as an insecticide, it became infamous for its environmental impacts. DDT was first synthesized in 1874 by the Austrian chemist Othmar Zeidler. DDT's insecticidal action was discovered by the Swiss chemist Paul Hermann Müller in 1939. DDT was used in the second half of World War II to limit the spread of the insect-borne diseases malaria and typhus among civilians and troops. Müller was awarded the Nobel Prize in Physiology or Medicine in 1948 "for his discovery of the high efficiency of DDT as a contact poison against several arthropods".

Defatting (medical)

Defatting (medical)

Defatting is the chemical dissolving of dermal lipids, from the skin, on contact with defatting agents. This can result in water loss from the affected area and cause the whitening and drying of the skin which may result in cracking, secondary infection and chemical irritant contact dermatitis.

Hydrochloric acid

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. It is a component of the gastric acid in the digestive systems of most animal species, including humans. Hydrochloric acid is an important laboratory reagent and industrial chemical.

Carbon dioxide

Carbon dioxide

Carbon dioxide (chemical formula CO2) is a chemical compound made up of molecules that each have one carbon atom covalently double bonded to two oxygen atoms. It is found in the gas state at room temperature, and as the source of available carbon in the carbon cycle, atmospheric CO2 is the primary carbon source for life on Earth. In the air, carbon dioxide is transparent to visible light but absorbs infrared radiation, acting as a greenhouse gas. Carbon dioxide is soluble in water and is found in groundwater, lakes, ice caps, and seawater. When carbon dioxide dissolves in water, it forms carbonate and mainly bicarbonate (HCO−3), which causes ocean acidification as atmospheric CO2 levels increase.

Allosteric modulator

Allosteric modulator

In pharmacology and biochemistry, allosteric modulators are a group of substances that bind to a receptor to change that receptor's response to stimuli. Some of them, like benzodiazepines, are drugs. The site that an allosteric modulator binds to is not the same one to which an endogenous agonist of the receptor would bind. Modulators and agonists can both be called receptor ligands.

GABAA receptor

GABAA receptor

The GABAA receptor (GABAAR) is an ionotropic receptor and ligand-gated ion channel. Its endogenous ligand is γ-aminobutyric acid (GABA), the major inhibitory neurotransmitter in the central nervous system. Upon opening, the GABAA receptor on the postsynaptic cell is selectively permeable to chloride ions (Cl−) and, to a lesser extent, bicarbonate ions (HCO3−). Depending on the membrane potential and the ionic concentration difference, this can result in ionic fluxes across the pore. If the membrane potential is higher than the equilibrium potential (also known as the reversal potential) for chloride ions, when the receptor is activated Cl− will flow into the cell. This causes an inhibitory effect on neurotransmission by diminishing the chance of a successful action potential occurring at the postsynaptic cell. The reversal potential of the GABAA-mediated inhibitory postsynaptic potential (IPSP) in normal solution is −70 mV, contrasting the GABAB IPSP (-100 mV).

Central nervous system

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 parts of the bodies of bilaterally symmetric and triploblastic animals—that is, all multicellular animals except sponges and diploblasts. It is a structure composed of nervous tissue positioned along the rostral to caudal axis of the body and may have an enlarged section at the rostral end which is a brain. Only arthropods, cephalopods and vertebrates have a true brain.

Coma

Coma

A coma is a deep state of prolonged unconsciousness in which a person cannot be awakened, fails to respond normally to painful stimuli, light, or sound, lacks a normal wake-sleep cycle and does not initiate voluntary actions. Person may experience respiratory and circulatory problems due to the body's inability to maintain normal bodily functions. People in a coma often require extensive medical care to maintain their health and prevent complications such as pneumonia or blood clots. Coma patients exhibit a complete absence of wakefulness and are unable to consciously feel, speak or move. Comas can be derived by natural causes, or can be medically induced.

Nausea

Nausea

Nausea is a diffuse sensation of unease and discomfort, sometimes perceived as an urge to vomit. While not painful, it can be a debilitating symptom if prolonged and has been described as placing discomfort on the chest, abdomen, or back of the throat.

Hyperthermia

Hyperthermia

Hyperthermia, also known simply as overheating, is a condition in which an individual's body temperature is elevated beyond normal due to failed thermoregulation. The person's body produces or absorbs more heat than it dissipates. When extreme temperature elevation occurs, it becomes a medical emergency requiring immediate treatment to prevent disability or death. Almost half a million deaths are recorded every year from hyperthermia.

Jaundice

Jaundice

Jaundice, also known as icterus, is a yellowish or greenish pigmentation of the skin and sclera due to high bilirubin levels. Jaundice in adults is typically a sign indicating the presence of underlying diseases involving abnormal heme metabolism, liver dysfunction, or biliary-tract obstruction. The prevalence of jaundice in adults is rare, while jaundice in babies is common, with an estimated 80% affected during their first week of life. The most commonly associated symptoms of jaundice are itchiness, pale feces, and dark urine.

Bioremediation of chloroform

Some anaerobic bacteria use chloroform for their respiration, termed organohalide respiration, converting it to dichloromethane.[69][70]

Source: "Chloroform", Wikipedia, Wikimedia Foundation, (2023, March 15th), https://en.wikipedia.org/wiki/Chloroform.

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Further Reading

Chlorine

Phosgene

Haloalkane

Dichloromethane

1,1,1-Trichloroethane

Trichloroethylene

Triphenylmethane

Phosphorus pentachloride

Sulfuryl chloride

Antimony pentachloride

Triphenylphosphine oxide

Haloform reaction
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