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Sodium hydroxide
From Wikipedia, the free encyclopedia
Jump to: navigation, search
Sodium hydroxide

IUPAC name[hide]
Sodium hydroxide
Systematic name[hide]
Sodium oxidanide
Other names[hide]
Caustic soda
Lye
Identifiers
CAS number 1310-73-2
PubChem 14798
ChemSpider 14114
UNII 55X04QC32I
EC number 215-185-5
UN number 1823
KEGG C12569
MeSH Sodium+hydroxide
ChEBI CHEBI:32145
RTECS number WB4900000
Gmelin Reference 68430
SMILES
[show]
InChI
[show]
Properties
Molecular formula NaOH
Exact mass 39.992509329 g mol−1
Appearance White opaque crystals
Density 2.13 g cm−3
Melting point 318 °C, 591 K, 604 °F
Boiling point 1388 °C, 1661 K, 2530 °F
Solubility in water 1110 g dm−3 (at 20 °C)
Solubility in methanol 238 g dm−3
Solubility in ethanol <<139 g dm−3
Vapor pressure <18 mmHg (at 20 °C)
Acidity (pKa) 13
Refractive index (nD) 1.412
Hazards
MSDS External MSDS
EU Index 011-002-00-6

EU classification
C
R-phrases R35
S-phrases (S1/2), S26, S37/39, S45

NFPA 704 0
3
1
COR
Related compounds
Other anions Sodium hydrosulfide
Caesium hydroxide

Other cations Lithium hydroxide


Potassium hydroxide
Rubidium hydroxide
(what is this?) (verify)
Except where noted otherwise, data are given for materials in
their standard state (at 25 °C, 100 kPa)
Infobox references

Sodium hydroxide (NaOH), also known as lye and caustic soda, is a caustic metallic
base. It is used in many industries, mostly as a strong chemical base in the manufacture of
pulp and paper, textiles, drinking water, soaps and detergents and as a drain cleaner.
Worldwide production in 2004 was approximately 60 million tonnes, while demand was
51 million tonnes.[1]

Pure sodium hydroxide is a white solid available in pellets, flakes, granules, and as a 50%
saturated solution. It is hygroscopic and readily absorbs water from the air, so it should
be stored in an airtight container. It is very soluble in water with liberation of heat. It also
dissolves in ethanol and methanol, though it exhibits lower solubility in these solvents
than does potassium hydroxide. Molten sodium hydroxide is also a strong base, but the
high temperature required limits applications. It is insoluble in ether and other non-polar
solvents. A sodium hydroxide solution will leave a yellow stain on fabric and paper.

Contents
[hide]

• 1 Properties
• 2 Reactions
• 3 Production
o 3.1 Chloralkali electrolysis
• 4 Uses
o 4.1 pH regulation
o 4.2 Paper making
o 4.3 Tissue digestion
o 4.4 Dissolving amphoteric metals and compounds
o 4.5 Esterification and transesterification reagent
o 4.6 Cleaning agent
o 4.7 Food preparation
o 4.8 Domestic uses
• 5 Safety
• 6 See also
• 7 References
• 8 Bibliography

• 9 External links

Properties
Sodium hydroxide is predominantly ionic, containing sodium cations and hydroxide
anions. The hydroxide anion makes sodium hydroxide a strong base which reacts with
acids to form water and the corresponding salts.

ΔH°dissolution for aqueous dilution is −44.45 kJ / mol; from aqueous solutions at 12.3–61.8
°C, it crystallizes in monohydrate, with a melting point 65.1 °C and density of 1.829
g/cm3. The standard enthalpy change of formation (ΔH°form) is −734.95 kJ / mol.

Reactions
With acids

Sodium hydroxide reacts with protic acids to give water and the corresponding salts. For
example, with hydrochloric acid, sodium chloride is formed:

NaOH(aq) + HCl(aq) → NaCl(aq) + H2O(l)

In general such neutralization reactions are represented by one simple net ionic equation:

OH−(aq) + H+(aq) → H2O(l)

This type of reaction with a strong acid releases heat, and hence is referred to as
exothermic. Such acid-base reactions can also be used for titrations. However, sodium
hydroxide is not used as a primary standard because it is hygroscopic and absorbs carbon
dioxide from air.

Sodium hydroxide reacts readily with carboxylic acids to form their salts and is even a
strong enough base to form salts with phenols. It is not, however, strong enough the
quantitatively produce enolates from carbonyl compounds or deprotonate amines; this
would require a superbase.

With acidic oxides

Sodium hydroxide also reacts with acidic oxides, such as sulfur dioxide. Such reactions
are often used to "scrub" harmful acidic gases (like SO2 and H2S) produced in the burning
of coal and thus prevent their release into the atmosphere. For example,

2 NaOH + CO2 → Na2CO3 + H2O


With amphoteric metals and oxides

Sodium hydroxide slowly reacts with glass to form sodium silicate, so glass joints and
stopcocks exposed to NaOH have a tendency to "freeze". Flasks and glass-lined chemical
reactors are damaged by long exposure to hot sodium hydroxide, and the glass becomes
frosted. Sodium hydroxide does not attack iron since iron does not have amphoteric
properties (i.e., it only dissolves in acid, not base). A few transition metals, however, may
react vigorously with sodium hydroxide.
In 1986, an aluminium road tanker in the UK was mistakenly used to transport 25%
sodium hydroxide solution[citation needed], causing pressurization of the contents and damage
to the tanker. The pressurization was due to the hydrogen gas which is produced in the
reaction between sodium hydroxide and aluminium:

2 Al + 2 NaOH + 2 H2O → 2 NaAlO2 + 3 H2


Precipitant

Unlike NaOH, the hydroxides of most transition metals are insoluble, and therefore
sodium hydroxide can be used to precipitate transition metal hydroxides.

Aluminium hydroxide is used as a gelatinous flocculant to filter out particulate matter in


water treatment. Aluminium hydroxide is prepared at the treatment plant from aluminium
sulfate by reacting it with NaOH.

Al2(SO4)3 + 6 NaOH → 2 Al(OH)3 + 3 Na2SO4


Saponification

NaOH can be used for the base-driven hydrolysis of esters (as in saponification), amides
and alkyl halides. However, the limited solubility of NaOH in organic solvents means
that the more soluble KOH is often preferred.

Electrolysis

In the laboratory, with careful control of conditions, sodium metal can be isolated from
the electrolysis of the molten monohydrate according to the following reaction:

4 NaOH·H2O(l) → 4 Na(l) + O2(g) + 6 H2O(g)

The monohydrate does not need to be heated in order to melt, as the process produces
enough heat due to ohmic heating. However, it must be initiated with a small quantity of
liquid water to create an electrically conductive electrolyte. As the system's temperature
increases, the monohydrate will start to melt at about 65 °C as stated above. Only when
the temperature reaches about 100 °C can sodium be isolated. Below this temperature, the
water produced will react with the sodium, above this point, any water formed will be
driven off in the vapour phase, creating an essentially anhydrous reaction. While this
process has some advantages over other electrolytic processes, it is not preferred by most
chemists for several reasons: a marginal quantity of sodium produced boils at the
electrode interface, the vapour thus given off consists primarily of fumed sodium oxide,
which tends to settle on any surface in close proximity with corrosive consequences.

Production
Sodium hydroxide is industrially produced as a 50 % solution by variations of the
electrolytic chloralkali process. Chlorine gas is also produced in this process. Solid
sodium hydroxide is obtained from this solution by the evaporation of water. Solid
sodium hydroxide is most commonly sold as flakes, prills, and cast blocks.[1]

In 2004, world production was estimated at 60 million dry metric tonnes of sodium
hydroxide, and demand was estimated at 51 million tonnes.[1] In 1998, total world
production was around 45 million tonnes. North America and Asia collectively
contributed around 14 million tonnes, while Europe produced around 10 million tonnes.
In the United States, the major producer of sodium hydroxide is the Dow Chemical
Company, which has annual production around 3.7 million tonnes from sites at Freeport,
Texas, and Plaquemine, Louisiana. Other major US producers include Oxychem, PPG,
Olin, Pioneer Companies (which was purchased by Olin), Inc. (PIONA), and Formosa.
All of these companies use the chloralkali process.[2]

Of historic interest is the Leblanc process, which produced sodium carbonate, followed
by roasting to create carbon dioxide and sodium oxide, which readily absorbs water to
create sodium hydroxide. This method is still occasionally used. It helped establish
sodium hydroxide as an important commodity chemical. The Leblanc process was
superseded by the Solvay process in the late 19th century.

Sodium hydroxide may be formed by the metathesis reaction between calcium


hydroxide(also known as lime) and sodium carbonate (also known as soda ash):[3]

Ca(OH)2 + Na2CO3 → CaCO3 + 2 NaOH

Chloralkali electrolysis

Basic membrane cell used in the electrolysis of brine.


Main article: Chloralkali process

Sodium hydroxide is produced (along with chlorine and hydrogen) via the chloralkali
process. This involves the electrolysis of an aqueous solution of sodium chloride. The
sodium hydroxide builds up at the cathode, where water is reduced to hydrogen gas and
hydroxide ion:

2 Na+ + 2 H2O + 2 e– → H2 + 2 NaOH

More accurately:
2 Na+Cl– + 2 H2O + 2 e– → H2 + 2 Cl– + 2 NaOH

The Cl– ions are oxidized to chlorine gas at the anode.

To produce NaOH it is necessary to prevent reaction of the NaOH with the chlorine. This
is typically done in one of three ways, of which the membrane cell process is
economically the most viable.

• Mercury cell process (also called the Castner-Kellner process); sodium ions are
reduced to sodium metal, which forms an amalgam with a mercury cathode; this
sodium is then reacted with water to produce NaOH. There have been concerns
about mercury releases, although modern plants claim to be safe in this regard.[4]
• Diaphragm cell process; uses a steel cathode, and the reaction of NaOH with Cl2
is prevented using a porous diaphragm, often made of asbestos fibers. In the
diaphragm cell process the anode area is separated from the cathode area by a
permeable diaphragm. The brine is introduced into the anode compartment and
flows through the diaphragm into the cathode compartment. A diluted caustic
brine leaves the cell. The sodium hydroxide must usually be concentrated to 50%
and the salt removed. This is done using an evaporative process with about three
tonnes of steam per tonne of sodium hydroxide. The salt separated from the
caustic brine can be used to saturate diluted brine. The chlorine contains oxygen
and is purified by liquefaction and evaporation.[5][6]
• Membrane cell process; similar to the diaphragm cell process, with a Nafion
membrane to separate the cathode and anode reactions. Only sodium ions and a
little water pass through the membrane. It produces a higher quality of NaOH. Of
the three processes, the membrane cell process requires the lowest consumption of
electric energy and the amount of steam needed for concentration of the caustic is
relatively small (less than one tonne per tonne of sodium hydroxide).[5][7]

Uses

Canister of sodium hydroxide.


Sodium hydroxide is the principal strong base used in the chemical industry. In bulk it is
most often handled as an aqueous solution, since solutions are cheaper and easier to
handle. Sodium hydroxide, a strong base, is responsible for most of these applications.
Another strong base such as potassium hydroxide is likely to yield positive results as
well.

56 % of sodium hydroxide produced is used by the chemical industry, with 25 % of the


same total used by the paper industry. Sodium hydroxide is also used for the manufacture
of sodium salts and detergents, for pH regulation, and for organic synthesis. It is used in
the Bayer process of aluminium production.[1]

pH regulation

Sodium hydroxide is used in all sorts of scenarios where it is desirable to increase the
alkalinity of a mixture, or to neutralize acids.

For example, sodium hydroxide is used as an additive in drilling mud to increase


alkalinity in bentonite mud systems increases the mud viscosity, as well as to neutralise
any acid gas (such as hydrogen sulfide and carbon dioxide) which may be encountered in
the geological formation as drilling progresses.

In the same industry, poor quality crude oil can be treated with sodium hydroxide to
remove sulfurous impurities in a process known as caustic washing. As above, sodium
hydroxide reacts with weak acids such as hydrogen sulfide and mercaptans to give the
non-volatile sodium salts which can be removed. The waste which is formed is toxic and
difficult to deal with, and the process is banned in many countries because of this. In
2006, Trafigura used the process and then dumped the waste in Africa.[8][9]

See also: hydrodesulfurization

Paper making

Main article: paper making

Sodium hydroxide was also widely used in making paper. Along with sodium sulfide,
NaOH is a key component of the white liquor solution used to separate lignin from
cellulose fibers in the Kraft process. It also plays a key role in several later stages of the
process of bleaching the brown pulp resulting from the pulping process. These stages
include oxygen delignification, oxidative extraction, and simple extraction, all of which
require a strong alkaline environment with a pH > 10.5 at the end of the stages.

Tissue digestion

In a similar fashion, sodium hydroxide is used to digest tissues, such as in a process that
was used with farm animals at one time. This process involves the placing of a carcass
into a sealed chamber, which then puts the carcass in a mixture of sodium hydroxide and
water, which breaks chemical bonds keeping the body intact. This eventually turns the
body into a coffee-like[10][11] liquid, and the only solid that remains are bone hulls, which
could be crushed between one's fingertips.[12] Sodium hydroxide is frequently used in the
process of decomposing roadkill dumped in landfills by animal disposal contractors.[11]
Sodium hydroxide has also been used by criminals to dispose of their victims' bodies.[13]

Dissolving amphoteric metals and compounds

Strong bases attack aluminium. Sodium hydroxide reacts with aluminium and water to
release hydrogen gas. The aluminium takes the oxygen atom from sodium hydroxide
(NaOH), which in turn takes the oxygen atom from the water, and releases the two
hydrogen atoms. In this reaction, sodium hydroxide acts as an agent to make the solution
alkaline, which aluminium can dissolve in. This reaction can be useful in etching,
removing anodizing, or converting a polished surface to a satin-like finish, but without
further passivation such as anodizing or alodining the surface may become degraded,
either under normal use or in severe atmospheric conditions.

In the Bayer process, sodium hydroxide is used in the refining of alumina containing ores
(bauxite) to produce alumina (aluminium oxide) which is the raw material used to
produce aluminium metal via the electrolytic Hall-Héroult process. Since the alumina is
amphoteric, it dissolves in the sodium hydroxide, leaving impurities less soluble at high
pH such as iron oxides behind in the form of a highly alkaline red mud.

See also: Ajka alumina plant accident

Esterification and transesterification reagent

Sodium hydroxide is traditionally used in soap making (cold process soap,


saponification).[14] It was made in the nineteenth century for a hard surface rather than
liquid product because it was easier to store and transport.

For the manufacture of biodiesel, sodium hydroxide is used as a catalyst for the
transesterification of methanol and triglycerides. This only works with anhydrous sodium
hydroxide, because combined with water the fat would turn into soap, which would be
tainted with methanol. It is used more often than potassium hydroxide because it is
cheaper and a smaller quantity is needed.

Cleaning agent

Main article: Cleaning agent

Sodium hydroxide is frequently used as an industrial cleaning agent where it is often


called "caustic". It is added to water, heated, and then used to clean the process
equipment, storage tanks, etc. It can dissolve grease, oils, fats and protein based deposits.
The sodium hydroxide solution can also be added surfactants to stabilize dissolved
substances to prevent redeposition. A sodium hydroxide soak solution is used as a
powerful degreaser on stainless and glass bakeware. It is also a common ingredient in
oven cleaners.

A common use of sodium hydroxide is in the production of parts washer detergents. Parts
washer detergents based on sodium hydroxide are some of the most aggressive parts
washer cleaning chemicals. The sodium hydroxide based detergent include surfactants,
rust inhibitors and defoamers. A parts washer heats water and the detergent in a closed
cabinet and then sprays the heated sodium hydroxide and hot water at pressure against
dirty parts for degreasing applications. Sodium hydroxide used in this manner replaced
many solvent based systems in the early 1990s[citation needed] when trichloroethane was
outlawed by the Montreal Protocol. Water and sodium hydroxide detergent based parts
washers are considered to be an environmental improvement over the solvent based
cleaning methods.

Food preparation

Food uses of sodium hydroxide include washing or chemical peeling of fruits and
vegetables, chocolate and cocoa processing, caramel coloring production, poultry
scalding, soft drink processing, and thickening ice cream. Olives are often soaked in
sodium hydroxide to soften them, while pretzels and German lye rolls are glazed with a
sodium hydroxide solution before baking to make them crisp. Owing to the difficulty in
obtaining food grade sodium hydroxide in small quantities for home use, sodium
carbonate is often used in place of sodium hydroxide.[15]

Specific foods processed with sodium hydroxide include:

• The Pinoy or Filipino dessert (kakanin) called kutsinta uses a bit of lye water to
help give the rice flour batter a jelly like consistency.
• A similar process is also used in the kakanin known as pitsi-pitsi or pichi-pichi
(pit-chi-pit-chi) except that the mixture uses grated cassava instead of rice flour.
• The Scandinavian delicacy known as lutefisk (from lutfisk, "lye fish").
• Hominy is dried maize (corn) kernels reconstituted by soaking in lye-water. These
expand considerably in size and may be further processed by frying to make corn
nuts or by drying and grinding to make grits. Nixtamal is similar, but uses calcium
hydroxide instead of sodium hydroxide.
• Sodium hydroxide is also the chemical that causes gelling of egg whites in the
production of Century eggs.
• German pretzels are poached in a boiling sodium carbonate solution or cold
sodium hydroxide solution before baking, which contributes to their unique crust.
• Most yellow coloured Chinese noodles are made with lye-water but are
commonly mistaken for containing egg.

Domestic uses
Hardware store grade NaOH to be used as drain cleaner

Paint stripping with caustic soda

Sodium hydroxide is used in the home as a drain cleaning agent for clearing clogged
drains. It is distributed as a dry crystal or as a thick liquid gel. The chemical mechanism
employed is the conversion of grease to a form of soap. Soap is water-soluble, and can be
dissolved by flushing with water. This conversion occurs far more rapidly at high
temperatures, so commercial drain cleaners may also contain chemicals that react with
water to generate heat. Sodium hydroxide also decomposes complex molecules such as
the protein that composes hair. Such drain cleaners (and their acidic versions) are highly
caustic and should be handled with care.

Sodium hydroxide has been used as a relaxer to straighten hair. However, because of the
high incidence and intensity of chemical burns, chemical relaxer manufacturers have now
switched to other alkaline chemicals. Sodium hydroxide relaxers are still available, but
they are used mostly by professionals.

A solution of sodium hydroxide in water was traditionally used as the most common
paint stripper on wooden objects. Its use has become less common, because it can
damage the wood surface, raising the grain and staining the colour.

Safety
Solid sodium hydroxide and solutions of more than 2% by weight (0.5 M) should be
labeled as corrosive.

Chemical burn caused by exposure to a sodium hydroxide solution.

Solid sodium hydroxide or solutions of sodium hydroxide may cause chemical burns,
permanent injury or scarring if it contacts unprotected human, or other animal, tissue. It
may cause blindness if it contacts with the eye. Protective equipment such as rubber
gloves, safety clothing and eye protection should always be used when handling the
material or its solutions.

Dissolution of sodium hydroxide is highly exothermic, and the resulting heat may cause
heat burns or ignite flammables. It also produces heat when reacted with acids. Sodium
hydroxide is corrosive to some metals, e.g. aluminum, which produces flammable
hydrogen gas on contact. Sodium hydroxide is also mildly corrosive to glass, which can
cause damage to glazing or freezing of ground glass joints

Chloroform
From Wikipedia, the free encyclopedia
Jump to: navigation, search
Chloroform

IUPAC name[hide]
Chloroform
Systematic name[hide]
Trichloromethane
Other names[hide]
Formyl trichloride, Methane trichloride, Methyl trichloride,
Methenyl trichloride, TCM, Freon 20, R-20, UN 1888
Identifiers
CAS number 67-66-3
PubChem 6212
ChemSpider 5977
UNII 7V31YC746X
EC number 200-663-8
KEGG C13827
ChEBI CHEBI:35255
ChEMBL CHEMBL44618
RTECS number FS9100000
SMILES
[show]
InChI
[show]
Properties
Molecular formula CHCl3
Molar mass 119.38 g/mol
Appearance Colorless liquid
Density 1.483 g/cm3
Melting point -63.5 °C
Boiling point 61.2 °C
Solubility in water 0.8 g/100 ml (20 °C)
Refractive index (nD) 1.4459
Structure
Molecular shape Tetrahedral
Hazards
MSDS External MSDS
R-phrases R22, R38, R40, R48/20/22
S-phrases (S2), S36/37

NFPA 704
0
2
0
Flash point Non-flammable
U.S. Permissible
50 ppm (240 mg/m3) (OSHA)
exposure limit (PEL)
Supplementary data page
Structure and
n, εr, etc.
properties
Thermodynamic Phase behaviour
data Solid, liquid, gas
Spectral data UV, IR, NMR, MS
(what is this?) (verify)
Except where noted otherwise, data are given for materials in
their standard state (at 25 °C, 100 kPa)
Infobox references

Chloroform in its liquid state shown in a test tube

Chloroform is the organic compound with formula CHCl3. The colorless, sweet-
smelling, dense liquid is a trihalomethane, and is considered somewhat hazardous.
Several million tons are produced annually as a precursor to Teflon and refrigerants, but
its use for refrigerants is being phased out.[1]

Contents
[hide]

• 1 Occurrence
o 1.1 Marine
• 2 Production
o 2.1 Industrial routes
o 2.2 Deuterochloroform
o 2.3 Inadvertent formation of chloroform
• 3 Uses
o 3.1 As a solvent
o 3.2 As a reagent in organic synthesis
o 3.3 As an anesthetic
o 3.4 Veterinary use
• 4 Safety
o 4.1 Conversion to phosgene
• 5 References
• 6 External links

Occurrence
CHCl3 has a multitude of natural sources, both biogenic and abiotic. It is estimated that
greater than 90% of atmospheric CHCl3 is of natural origin.[2]

Marine

In particular, chloroform is produced by brown seaweeds (Laminaria digitata, Laminaria


saccharina, Fucus serratus, Pelvetia canaliculata, Ascophyllum nodosum), red seaweeds
(Gigartina stellata, Corallina officinalis, Polysiphonia lanosa), and green seaweeds
(Ulva lactuca, Enteromorpha sp., Cladophora albida).[3] Similarly, the macroalga
Eucheuma denticulatum, which is cultivated and harvested on a large scale for
carrageenan production, produces CHCl3,[4] as do Hypnea spinella, Falkenbergia
hillebrandii, and Gracilara cornea along with seven indigenous macroalgae inhabiting a
rock pool.[5] These studies show increased CHCl3 production with increased light
intensity, presumably when photosynthesis is at a maximum. Chloroform is also
produced by the brown alga Fucus vesiculosus, the green algae Cladophora glomerata,
Enteromorpha ahlneriana, Enteromorpha flexuosa, and Enteromorpha intestinalis, and
the diatom Pleurosira laevis.[6] Other studies observe CHCl3 in Fucus serratus, Fucus
vesiculosis, Corallina officinalis, Cladophora pellucida, and Ulva lactuca,[7] and
Desmarestia antarctica, Lambia antarctica, Laminaria saccharina, Neuroglossum
ligulatum.[8]

Production
Chloroform was discovered by three researchers independently of one another.
Chloroform was reported in 1831 by the French chemist Eugène Soubeiran, who
prepared it from acetone (2-propanone) as well as ethanol through the action of chlorine
bleach powder (calcium hypochlorite).[9] The American physician Samuel Guthrie
prepared gallons of the material and described its "deliciousness of flavor."[10]
Independently, Justus von Liebig also described the same compound.[11] All early
preparations used variations of the haloform reaction. Chloroform was named and
chemically characterized in 1834 by Jean-Baptiste Dumas.[12]

Industrial routes

In industry, chloroform is produced by heating a mixture of chlorine and either


chloromethane or methane.[1] 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 give CCl4:

CHCl3 + Cl2 → CCl4 + HCl

The output of this process is a mixture of the four chloromethanes, chloromethane,


dichloromethane, chloroform, and carbon tetrachloride, which are then separated by
distillation.[1]

Deuterochloroform

An archaic industrial route to chloroform involved the reaction of acetone (or ethanol)
with sodium hypochlorite or calcium hypochlorite, the aforementioned haloform reaction.
[1]
The chloroform can be removed from the coproducts by distillation. A related reaction
is still used in the production of bromoform and iodoform. Although the haloform
process is obsolete for the production of ordinary chloroform, it is used to produce
CDCl3.[citation needed] Deuterochloroform can also be prepared by the reaction of sodium
deuteroxide with chloral hydrate,[citation needed] or from ordinary chloroform.[13]

Inadvertent formation of chloroform

The haloform reaction can also occur inadvertently in domestic settings. Sodium
hypochlorite solution (chlorine bleach) mixed with common household liquids such as
acetone, butanone, ethanol, or isopropyl alcohol can produce some chloroform, in
addition to other compounds such as chloroacetone, or dichloroacetone.

Uses
The major use of chloroform today is in the production of the chlorodifluoromethane (R-
22), a major precursor to tetrafluoroethylene:

CHCl3 + 2 HF → CHClF2 + 2 HCl

The reaction is conducted in the presence of a catalytic amount of antimony


pentafluoride. Chlorodifluoromethane is then converted into tetrafluoroethylene, the main
precursor to Teflon. Before the Montreal Protocol, chlorodifluoromethane (R22) was also
a popular refrigerant.

As a solvent

Chloroform is a common solvent in the laboratory because it is relatively unreactive,


miscible with most organic liquids, and conveniently volatile. Chloroform is used as a
solvent in the pharmaceutical industry and for producing dyes and pesticides. Chloroform
is an effective solvent for alkaloids in their base form and thus plant material is
commonly extracted with chloroform for pharmaceutical processing. For example, it is
used in commerce to extract morphine from poppies and scopolamine from Datura
plants. Chloroform containing deuterium (heavy hydrogen), CDCl3, is a common solvent
used in NMR spectroscopy. It can be used to bond pieces of acrylic glass (also known
under the trade names Perspex and Plexiglas). A solvent of phenol:chloroform:isoamyl
alcohol 25:24:1 is used to dissolve non-nucleic acid biomolecules in DNA and RNA
extractions.

As a reagent in organic synthesis

As a reagent, chloroform serves as a source of the dichlorocarbene CCl2 group.[14] It


reacts with aqueous sodium hydroxide usually in the presence of a phase transfer catalyst
to produce dichlorocarbene, CCl2.[15][16] This reagent affects 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.

As an anesthetic

Antique bottles of Chloroform

Chloroform was once a popular anesthetic; its vapor depresses the central nervous system
of a patient, allowing a doctor to perform various otherwise painful procedures. In 1847,
the Scottish obstetrician James Young Simpson first used chloroform for general
anesthesia during childbirth. The use of chloroform during surgery expanded rapidly
thereafter in Europe. In the United States, chloroform began to replace ether as an
anesthetic at the beginning of the 20th century; however, it was quickly 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". Ether is still the
preferred anesthetic in some developing nations due to its high therapeutic index (~1.5–
2.2) [17] and low price. One possible mechanism of action for chloroform is that it
increases movement of potassium ions through certain types of potassium channels in
nerve cells.[18] 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.

Veterinary use

In veterinary medicine it is used externally to kill maggots in wounds.[citation needed]


Safety
Fatal oral dose of chloroform may be as low as 10 mL (14.8 g), with death due to
respiratory or cardiac arrest.[19]

As might be expected for an anesthetic, chloroform vapors depress the central nervous
system. It is immediately dangerous to life and health at approximately 500 ppm,
according to the U.S. National Institute for Occupational Safety and Health. Breathing
about 900 ppm for a short time can cause dizziness, fatigue, and headache. Chronic
chloroform exposure can damage the liver (where chloroform is metabolized to
phosgene) and to the kidneys, and some people develop sores when the skin is immersed
in chloroform.

Animal studies have shown that miscarriages occur in rats and mice that have breathed
air containing 30 to 300 ppm of chloroform during pregnancy and also in rats that have
ingested chloroform during pregnancy. Offspring of rats and mice that breathed
chloroform during pregnancy have a higher incidence of birth defects, and abnormal
sperm have been found in male mice that have breathed air containing 400 ppm
chloroform for a few days. The effect of chloroform on reproduction in humans is
unknown.

Chloroform once appeared in toothpastes, cough syrups, ointments, and other


pharmaceuticals, but it has been banned as a consumer product in the US since 1976.[20]
Cough syrups containing Chloroform can still be legally purchased in pharmacies and
supermarkets in the UK.

The US National Toxicology Program's eleventh report on carcinogens[21] implicates it as


reasonably anticipated to be a human carcinogen, a designation equivalent to
International Agency for Research on Cancer class 2A. The IARC itself classifies
chloroform as possibly carcinogenic to humans, a Group 2B designation.[22] It has been
most readily associated with hepatocellular carcinoma.[23][24] Caution is mandated during
its handling in order to minimize unnecessary exposure; safer alternatives, such as
dichloromethane, have resulted in a substantial reduction of its use as a solvent.

Conversion to phosgene

During prolonged storage in the presence of oxygen chloroform converts slowly to


phosgene. 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.[25] Dissolved phosgene
cannot be removed by distillation or carbon filters, but is removed by calcium hydroxide
or activated alumina.[26] Suspicious samples can be tested for phosgene using filter paper
(treated with 5% diphenylamine, 5% dimethylaminobenzaldehyde in alcohol, and then
dried), which turns yellow in phosgene vapor. There are several colorimetric and
fluorometric reagents for phosgene, and it can also be quantified with mass spectrometry.