Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
Formaldehyde (systematic name methanal), is a naturally occurring
organic compound with the formula CH2O (H-CHO). It is the simplest of
the aldehydes (R-CHO). The common name of this substance comes from
its similarity and relation to formic acid.
Formaldehyde is an important precursor to many other materials and
chemical compounds. In 1996, the installed capacity for the production
of formaldehyde was estimated to be 8.7 million tons per year. It
is mainly used in the production of industrial resins, e.g., for
particle board and coatings.
In view of its widespread use, toxicity, and volatility, formaldehyde
poses a significant danger to human health. In 2011, the US
National Toxicology Program
National Toxicology Program described formaldehyde as "known to be a
1 Forms of formaldehyde
2.1 Interstellar formaldehyde
3 Synthesis and industrial production
4 Organic chemistry
4.1 Self-condensation and hydration
4.3 Hydroxymethylation and chloromethylation
4.4 Base reactions
5.1 Industrial applications
5.2 Examples of organic synthetic applications
5.3 Disinfectant and biocide
5.4 Tissue fixative and embalming agent
5.5 Drug testing
6.1 International bans
Formaldehyde issues in trailers
6.2.1 Hurricanes Katrina and Rita
6.2.2 Iowa floods of 2008
7 Contaminant in food
8 See also
10 External links
Forms of formaldehyde
Formaldehyde is more complicated than many simple carbon compounds in
that it adopts several different forms. As a gas, formaldehyde is
colorless and has a characteristic pungent, irritating odor. Upon
condensation, the gas converts to various other forms of formaldehyde
(with different chemical formulas) that are of more practical value.
One important derivative is the cyclic trimer metaformaldehyde or
1,3,5-trioxane with the formula (CH2O)3. There is also a linear
polymer called paraformaldehyde. These compounds have similar chemical
properties and are often used interchangeably.
Paraformaldehyde is a common form of formaldehyde for industrial
When dissolved in water, formaldehyde also forms a hydrate,
methanediol, with the formula H2C(OH)2. This compound also exists in
equilibrium with various oligomers (short polymers), depending on the
concentration and temperature. A saturated water solution, of about
40% formaldehyde by volume or 37% by mass, is called "100% formalin".
A small amount of stabilizer, such as methanol, is usually added to
suppress oxidation and polymerization. A typical commercial grade
formalin may contain 10–12% methanol in addition to various metallic
impurities. The name was long ago genericized from an old trade name
Processes in the upper atmosphere contribute up to 90% of the total
formaldehyde in the environment.
Formaldehyde is an intermediate in
the oxidation (or combustion) of methane, as well as of other carbon
compounds, e.g. in forest fires, automobile exhaust, and tobacco
smoke. When produced in the atmosphere by the action of sunlight and
oxygen on atmospheric methane and other hydrocarbons, it becomes part
Formaldehyde has also been detected in outer space (see
Formaldehyde and its adducts are ubiquitous in living organisms. It is
formed in the metabolism of endogenous amino acids[which?] and is
found in the bloodstream of humans and other primates at
concentrations of approximately 0.1 millimolar. Experiments in
which animals are exposed to an atmosphere containing isotopically
labeled formaldehyde have demonstrated that even in deliberately
exposed animals, the majority of formaldehyde-
DNA adducts found in
non-respiratory tissues are derived from endogenously produced
Formaldehyde does not accumulate in the environment, because it is
broken down within a few hours by sunlight or by bacteria present in
soil or water. Humans metabolize formaldehyde quickly, so it does not
accumulate, converting it to formic acid in the body.
Main article: Interstellar formaldehyde
Formaldehyde was the first polyatomic organic molecule detected in the
interstellar medium. Since its initial detection in 1969, it has
been observed in many regions of the galaxy. Because of the widespread
interest in interstellar formaldehyde, it has recently been
extensively studied, yielding new extragalactic sources. A
proposed mechanism for the formation is the hydrogenation of CO ice,
H + CO → HCO
HCO + H → CH2O (rate constant=9.2×10−3 s−1)[clarification
Formaldehyde appears to be a useful probe for astrochemists due to its
low reactivity in the gas phase and to the fact that the 110←111 and
211←212 K-doublet transitions are rather clear.
On 11 August 2014, astronomers released studies, using the Atacama
Large Millimeter/Submillimeter Array (ALMA) for the first time, that
detailed the distribution of HCN, HNC, H2CO, and dust inside the comae
C/2012 F6 (Lemmon)
C/2012 F6 (Lemmon) and C/2012 S1 (ISON).
Synthesis and industrial production
Formaldehyde was first reported in 1859 by the Russian chemist
Aleksandr Butlerov (1828–86) and was conclusively identified in
1869 by August Wilhelm von Hofmann.
Formaldehyde is produced industrially by the catalytic oxidation of
methanol. The most common catalysts are silver metal or a mixture of
an iron and molybdenum or vanadium oxides. In the commonly used formox
process, methanol and oxygen react at ca. 250–400 °C in
presence of iron oxide in combination with molybdenum and/or vanadium
to produce formaldehyde according to the chemical equation:
2 CH3OH + O2 → 2 CH2O + 2 H2O
The silver-based catalyst usually operates at a higher temperature,
about 650 °C. Two chemical reactions on it simultaneously
produce formaldehyde: that shown above and the dehydrogenation
CH3OH → CH2O + H2
In principle, formaldehyde could be generated by oxidation of methane,
but this route is not industrially viable because the methanol is more
easily oxidized than methane.
Formaldehyde is a building block in the synthesis of many other
compounds of specialised and industrial significance. It exhibits most
of the chemical properties of other aldehydes but is more reactive.
Self-condensation and hydration
Formaldehyde, unlike most aldehydes, oligomerizes spontaneously. The
trimer is trioxane and the polymer is called paraformaldehyde. Many
cyclic oligomers have been isolated. Similarly, formaldehyde hydrates
to give the geminal diol, which condenses further to form oligomers
HO(CH2O)nH. Monomeric CH2O is rarely encountered.
It is more readily oxidized by atmospheric oxygen into formic acid.
For this reason, commercial formaldehyde typically is contaminated
with formic acid.
Hydroxymethylation and chloromethylation
Formaldehyde is a good electrophile. With good nucleophiles such as
thiols, amines, and even amides, no acid catalyst is required. The
resulting hydroxymethyl derivatives typically react further. Thus
amines give hexahydro-1,3,5-triazines. Similarly, when combined with
hydrogen sulfide, it forms trithiane.
3CH2O + 3H2S → (CH2S)3 + 3H2O
In the presence of acids, it participates in electrophilic aromatic
substitution reactions with aromatic compounds resulting in
ArH + CH2O → ArCH2OH
When conducted in the presence of hydrogen chloride, the product is
the chloromethyl compound, as described in the Blanc
chloromethylation. If the arene is electron-rich, as in phenols,
elaborate condensations ensue. With 4-substituted phenols one obtains
calixarenes. Phenol results in polymers.
Cannizzaro reaction in the presence of basic catalysts to produce
formic acid and methanol.
Formaldehyde is a common precursor to more complex compounds and
materials. In approximate order of decreasing consumption, products
generated from formaldehyde include urea formaldehyde resin, melamine
resin, phenol formaldehyde resin, polyoxymethylene plastics,
1,4-butanediol, and methylene diphenyl diisocyanate. The textile
industry uses formaldehyde-based resins as finishers to make fabrics
crease-resistant. Formaldehyde-based materials are key to the
manufacture of automobiles, and used to make components for the
transmission, electrical system, engine block, door panels, axles and
brake shoes. The value of sales of formaldehyde and derivative
products was over $145 billion in 2003, about 1.2% of the gross
domestic product (GDP) of the United States and Canada. Including
indirect employment, over 4 million people work in the formaldehyde
industry across approximately 11,900 plants in the U.S. and
Two steps in formation of urea-formaldehyde resin, which is widely
used in the production of particle board.
When treated with phenol, urea, or melamine, formaldehyde produces,
respectively, hard thermoset phenol formaldehyde resin, urea
formaldehyde resin, and melamine resin. These polymers are common
permanent adhesives used in plywood and carpeting. It is used as the
wet-strength resin added to sanitary paper products such as (listed in
increasing concentrations injected into the paper machine headstock
chest) facial tissue, table napkins, and roll towels. They are also
foamed to make insulation, or cast into moulded products. Production
of formaldehyde resins accounts for more than half of formaldehyde
Formaldehyde is also a precursor to polyfunctional alcohols such as
pentaerythritol, which is used to make paints and explosives. Other
formaldehyde derivatives include methylene diphenyl diisocyanate, an
important component in polyurethane paints and foams, and hexamine,
which is used in phenol-formaldehyde resins as well as the explosive
Examples of organic synthetic applications
Condensation with acetaldehyde affords pentaerythritol, a chemical
necessary in synthesizing PETN, a high explosive. Condensation
with phenols gives phenol-formaldehyde resins.
Disinfectant and biocide
An aqueous solution of formaldehyde can be useful as a disinfectant as
it kills most bacteria and fungi (including their spores).
Formaldehyde solutions are applied topically in medicine to dry the
skin, such as in the treatment of warts. Many aquarists use
formaldehyde as a treatment for the parasites Ichthyophthirius
multifiliis and Cryptocaryon irritans.
Formaldehyde is used to inactivate bacterial products for toxoid
vaccines (vaccines that use an inactive bacterial toxin to produce
immunity). It is also used to kill unwanted viruses and bacteria that
might contaminate the vaccine during production. Urinary tract
infections are also often treated using a derivative of formaldehyde
(methenamine), a method often chosen because it prevents overuse of
antibiotics and the resultant development of bacterial resistance to
them. In an acid environment, methenamine is converted in the kidneys
to formaldehyde, which then has an antibacterial effect in the urinary
tract. Some topical creams, cosmetics, and personal hygiene products
contain derivatives of formaldehyde as the active ingredients that
prevent the growth of potentially harmful bacteria.
Formaldehyde is also approved for use in the manufacture of animal
feeds in the US. It is an antimicrobial agent used to maintain
complete animal feeds or feed ingredients
Salmonella negative for up
to 21 days.
Tissue fixative and embalming agent
Injecting a giant squid specimen with formalin for preservation.
Formaldehyde preserves or fixes tissue or cells by a mixture of
reversible (short exposure time and low temperatures) and irreversible
(long exposure time and higher temperatures) cross-linking of primary
amino groups in proteins with other nearby nitrogen atoms in protein
DNA through a -CH2- linkage. This is exploited in
ChIP-sequencing genomics experiments, where DNA-binding proteins are
cross-linked to their cognate binding sites on the chromosome and
analyzed to determine what genes are regulated by the proteins.
Formaldehyde is also used as a denaturing agent in
RNA from forming secondary structures. A
solution of 4% formaldehyde fixes pathology tissue specimens at about
one mm per hour at room temperature.
Formaldehyde solutions are used as a fixative for microscopy and
histology because of formaldehyde's ability to perform the Mannich
reaction, although the percentage formaldehyde used may vary based on
the method of analysis. Additionally, the methanol used to stabilize
formaldehyde may interfere with the ability to properly fix tissue or
cells, and therefore commercial formaldehyde preparations are
available that are packaged in glass ampules under an inert gas to
prevent the use of contaminating methanol for stabilization.
Formaldehyde-based solutions are also used in embalming to disinfect
and temporarily preserve human and animal remains. It is the ability
of formaldehyde to fix the tissue that produces the tell-tale firmness
of flesh in an embalmed body. In post mortem examinations a procedure
known as the "sink test" involves placing the lungs of an animal in an
aqueous solution of formaldehyde; if the lungs float it suggests the
animal was probably breathing or able to breathe at the time of death.
Although formaldehyde solutions are commonly used as a biological
preserving medium, usually for smaller specimens, it delays, but does
not prevent, decay. This method of fixation does not preserve nucleic
acids, thus preventing, for example, genetic analysis of the first
Several European countries restrict the use of formaldehyde, including
the import of formaldehyde-treated products and embalming. Starting
September 2007, the European Union banned the use of formaldehyde due
to its carcinogenic properties as a biocide (including embalming)
Biocidal Products Directive (98/8/EC). Countries
with a strong tradition of embalming corpses, such as Ireland and
other colder-weather countries, have raised concerns. Despite reports
to the contrary, no decision on the inclusion of formaldehyde on
Annex I of the
Biocidal Products Directive for
product-type 22 (embalming and taxidermist fluids) had been made
as of September 2009[update].
Formaldehyde, along with 18 M (concentrated) sulfuric acid makes
Marquis reagent which can be used to identify alkaloids and other
In photography, formaldehyde is used in low concentrations for process
C-41 (color negative film) stabilizer in the final wash step, as
well as in the process E-6 pre-bleach step, to make it unnecessary in
the final wash.
The safety of formaldehyde is very complicated. It occurs naturally
and is "an essential intermediate in cellular metabolism in mammals
and humans." It is not acutely toxic as ingestion of many
milliliters is tolerated. The main concerns are associated with
chronic (long term) exposure by inhalation. This may happen through 3
main sources: thermal or chemical decomposition of formaldehyde-based
resins, emission from aqueous formaldehyde solutions (i.e. embalming
fluids), and the production of formaldehyde resulting from the
combustion of a variety of organic compounds (for example, exhaust
gases). As formaldehyde resins are used in many construction materials
it is one of the more common indoor air pollutants. At
concentrations above 0.1 ppm in air formaldehyde can irritate the
eyes and mucous membranes, resulting in watery eyes. Formaldehyde
inhaled at this concentration may cause headaches, a burning sensation
in the throat, and difficulty breathing, and can trigger or aggravate
A 1988 Canadian study of houses with urea-formaldehyde foam insulation
found that formaldehyde levels as low as 0.046 ppm were positively
correlated with eye and nasal irritation. A recent review of
studies has shown a strong association between exposure to
formaldehyde and the development of childhood asthma. The primary
exposure concern is for the workers in the industries producing or
The formaldehyde theory of carcinogenesis was proposed in 1978. In
1987 the U.S. EPA classified it as a probable human carcinogen, and
after more studies the
WHO International Agency for Research on Cancer
(IARC) in 1995 also classified it as a probable human carcinogen.
Further information and evaluation of all known data led the IARC to
reclassify formaldehyde as a known human carcinogen associated
with nasal sinus cancer and nasopharyngeal cancer. Recent studies
have also shown a positive correlation between exposure to
formaldehyde and the development of leukemia, particularly myeloid
leukemia. Nasopharyngeal and sinonasal cancers are relatively
rare, with a combined annual incidence in the United States of <
4,000 cases. About 25,000 cases of myeloid leukemia occur in
the United States each year. Workplace exposure to inhaled
chemicals is among the most important risk factors for sinonasal
cancers. Professionals exposed to formaldehyde in their
occupation, such as funeral industry workers and embalmers, showed an
increased risk of leukemia and brain cancer compared with the general
population. Other factors are important in determining individual
risk for the development of leukemia or nasopharyngeal
In the residential environment, formaldehyde exposure comes from a
number of different routes; formaldehyde can off-gas from wood
products, such as plywood or particle board, but it is produced by
paints, varnishes, floor finishes, and cigarette smoking as well.
In July 2016, the EPA released a prepublication version of its final
Formaldehyde Emission Standards for Composite Wood Products.
These new rules will impact manufacturers, importers, distributors,
and retailers of products containing composite wood, including
fiberboard, particleboard and various laminated products, who will
need to comply with more stringent record-keeping and labeling
United States Environmental Protection Agency
United States Environmental Protection Agency (EPA) allows no more
than 0.016 ppm formaldehyde in the air in new buildings
constructed for that agency. A U.S. Environmental Protection
Agency study found a new home measured 0.076 ppm when brand new and
0.045 ppm after 30 days. The Federal Emergency Management Agency
(FEMA) has also announced limits on the formaldehyde levels in
trailers purchased by that agency. The EPA recommends the use of
"exterior-grade" pressed-wood products with phenol instead of urea
resin to limit formaldehyde exposure, since pressed-wood products
containing formaldehyde resins are often a significant source of
formaldehyde in homes.
For most people, irritation from formaldehyde is temporary and
reversible, though formaldehyde can cause allergies and is part of the
standard patch test series. In 2005–06, it was the
seventh-most-prevalent allergen in patch tests (9.0%). People with
formaldehyde allergy are advised to avoid formaldehyde releasers as
well (e.g., Quaternium-15, imidazolidinyl urea, and diazolidinyl
urea). People who suffer allergic reactions to formaldehyde tend
to display lesions on the skin in the areas that have had direct
contact with the substance, such as the neck or thighs (often due to
formaldehyde released from permanent press finished clothing) or
dermatitis on the face (typically from cosmetics). Formaldehyde
has been banned in cosmetics in both
Sweden and Japan.[citation
needed] The eyes are most sensitive to formaldehyde exposure: The
lowest level at which many people can begin to smell formaldehyde is
about 0.05 ppm and the highest level is 1 ppm. The maximum
concentration value at the workplace is 0.3 ppm. In controlled
chamber studies, individuals begin to sense eye irritation at about
0.5 ppm; 5 to 20 percent report eye irritation at 0.5 to 1 ppm; and
greater certainty for sensory irritation occurred at 1 ppm and above.
While some agencies have used a level as low as 0.1 ppm as a threshold
for irritation, the expert panel found that a level of 0.3 ppm would
protect against nearly all irritation. In fact, the expert panel found
that a level of 1.0 ppm would avoid eye irritation—the most
sensitive endpoint—in 75–95% of all people exposed.
Formaldehyde levels in building environments are affected by a number
of factors. These include the potency of formaldehyde-emitting
products present, the ratio of the surface area of emitting materials
to volume of space, environmental factors, product age, interactions
with other materials, and ventilation condition.
from a variety of construction materials, furnishings, and consumer
products. The three products that emit the highest concentrations are
medium density fiberboard, hardwood plywood, and particle board.
Environmental factors such as temperature and relative humidity can
elevate levels because formaldehyde has a high vapor pressure.
Formaldehyde levels from building materials are the highest when a
building first opens because materials would have less time to
Formaldehyde levels decrease over time as the sources
Formaldehyde levels in air can be sampled and tested in several ways,
including impinger, treated sorbent, and passive monitors. The
National Institute for Occupational Safety and Health
National Institute for Occupational Safety and Health (NIOSH) has
measurement methods numbered 2016, 2541, 3500, and 3800.
Studies on the interactions between formaldehyde and proteins at the
molecular level have been reported on the effects of the body’s
carrier protein, serum albumin. The binding of formaldehyde loosens
the skeletal structure of albumin and exposure of aromatic ring amino
acids in the internal hydrophobic region. Symptoms may affect personal
awareness, making one feel tired or fatigued.
Formaldehyde inhalation has also shown to cause oxidative stress and
inflammation in animals. Mice studied over an exposure to a high dose
of formaldehyde (3ppm), showed increased NO−
3 levels in plasma. This result suggests that FA inhalation either
decreased NO production or increased NO scavenging, which may be an
anti-stress mechanism in the body.
Formaldehyde inhalation changes the
sensitivity of immune system, which influences oxidative
In June 2011, the twelfth edition of the National Toxicology Program
(NTP) Report on Carcinogens (RoC) changed the listing status of
formaldehyde from "reasonably anticipated to be a human carcinogen" to
"known to be a human carcinogen". Concurrently, a National
Academy of Sciences (NAS) committee was convened and issued an
independent review of the draft United States Environmental Protection
Agency IRIS assessment of formaldehyde, providing a comprehensive
health effects assessment and quantitative estimates of human risks of
There are several web articles claiming that formaldehyde has been
banned from manufacture or import into the European Union (EU) under
REACH (Registration, Evaluation, Authorization, and restriction of
Chemical substances) legislation. This appears to be misinformation,
as official EU chemical databases[which?] contradict these claims as
of February 19, 2010. This misconception has gained some ground.
Formaldehyde is not listed in the Annex I of
Regulation (EC) No
689/2008 (export and import of dangerous chemicals regulation), nor on
a priority list for risk assessment. However, formaldehyde is banned
from use in certain applications (preservatives for liquid-cooling and
processing systems, slimicides, metalworking-fluid preservatives, and
antifouling products) under the Biocidal Products Directive.
In the EU, the maximum allowed concentration of formaldehyde in
finished products is 0.2%, and any product that exceeds 0.05% has to
include a warning that the product contains formaldehyde.
In the United States, a bill was passed in Congress on July 7, 2010,
regarding the use of formaldehyde in hardwood plywood, particle board,
and medium density fiberboard. The bill limited the allowable amount
of formaldehyde emissions from these wood products to .09 ppm, a
standard which companies were required to meet by January 2013.
Formaldehyde was declared a toxic substance by the 1999 Canadian
Environmental Protection Act.
Formaldehyde issues in trailers
"Episode 202: Where Have All the FEMA Trailers Gone? Tracing Toxicity
from Bust to Boom", Distillations, September 2, 2015, Science History
Where Have All the Trailers Gone?, Video by Mariel Carr
(Videographer) & Nick Shapiro (Researcher), 2015, Science History
Hurricanes Katrina and Rita
In the U.S. the
Federal Emergency Management Agency
Federal Emergency Management Agency (FEMA) provided
travel trailers, recreational park trailers and manufactured homes
starting in 2006 for habitation by residents of the U.S. gulf coast
Hurricane Katrina and Hurricane Rita. Some of the people
who moved into the FEMA trailers complained of breathing difficulties,
nosebleeds, and persistent headaches. Formaldehyde-catalyzed resins
were used in the production of these homes.
The United States Centers For Disease Control and Prevention (CDC)
performed indoor air quality testing for formaldehyde in some of
the units. On February 14, 2008, the CDC announced that potentially
hazardous levels of formaldehyde were found in many of the travel
trailers and manufactured homes provided by the agency. The
CDC's preliminary evaluation of a scientifically established random
sample of 519 travel trailers and manufactured homes tested between
December 21, 2007, and January 23, 2008 (2+ years after manufacture),
showed average levels of formaldehyde in all units of about 0.077
parts per million (ppm). Long-term exposure to levels in this range
can be linked to an increased risk of cancer and, at levels above this
range, there can also be a risk of respiratory illness. These levels
are higher than expected in indoor air, where levels are commonly in
the range of 0.01–0.02 ppm, and are higher than the Agency for Toxic
Substance Disease Registry (ATSDR, division of the CDC) Minimal Risk
Level (MRL) of 0.008 ppm. Levels measured ranged from 0.003 ppm to
FEMA, which requested the testing by the CDC, said it would work
aggressively to relocate all residents of the temporary housing as
soon as possible. Lawsuits were filed against FEMA trailer
manufacturers as a result of the exposures. As of 2012, U.S.
Kurt D. Engelhardt of New Orleans approved a $42.6
million class-action lawsuit settlement for the plaintiffs, who
included roughly 55,000 residents of Louisiana, Mississippi, Alabama
and Texas. The defendants included two dozen manufacturers who built
mobile homes for the
Federal Emergency Management Agency
Federal Emergency Management Agency (FEMA),
including Gulf Stream Coach Inc., Forest River Inc., Vanguard LLC and
Monaco Coach Corp. A separate $5.1 million settlement dealt with
claims against FEMA contractors including Shaw Environmental Inc.,
Bechtel Corp., Fluor Enterprises Inc. and CH2M Hill Constructors Inc.,
who were responsible for installing and maintaining the units.
Iowa floods of 2008
Also in the U.S., problems arose in trailers again provided by FEMA to
residents displaced by the Iowa floods of 2008. Several months after
moving to the trailers, occupants reported violent coughing,
headaches, as well as asthma, bronchitis, and other problems. Tests
showed that in some trailers, levels of formaldehyde exceeded the
limits recommended by the U.S.
Environmental Protection Agency
Environmental Protection Agency and
American Lung Association. The associated publicity has
resulted in additional testing to begin in November.
Contaminant in food
Formaldehyde occurs naturally and is "an essential intermediate in
cellular metabolism in mammals and humans." At high concentrations
it is probably unhealthy. Scandals have broken in both the 2005
Indonesia food scare and
2007 Vietnam food scare regarding the
addition of formaldehyde to foods to extend shelf life. In 2011, after
a four-year absence, Indonesian authorities found foods with
formaldehyde being sold in markets in a number of regions across the
country. Besides using formaldehyde, they also used borax, but not in
combination. In August 2011, at least at two Carrefour
supermarkets, the Central
Jakarta Livestock and Fishery Sub-Department
found a sweet glutinous rice drink (cendol) contained 10 parts per
million of formaldehyde. In 2014, the owner of two noodle
factories in Bogor, Indonesia; was arrested for using formaldehyde in
noodles. 50 kg of formaldehyde was confiscated. Foods known
to be contaminated include noodles, salted fish, and tofu; chicken and
beer are also rumored to be contaminated. In some places, such as
China, formaldehyde is still used illegally as a preservative in
foods, which exposes people to formaldehyde ingestion. In humans,
the ingestion of formaldehyde has been shown to cause vomiting,
abdominal pain, dizziness, and in extreme cases can cause death.
Testing for formaldehyde is by blood and/or urine by gas
chromatography-mass spectrometry. Other methods include infrared
detection, gas detector tubes, etc., of which HPLC is the most
sensitive. In the early 1900s, it was frequently added by US milk
plants to milk bottles as a method of pasteurization due to the lack
of knowledge regarding formaldehyde's toxicity.
In 2011 in Nakhon Ratchasima, Thailand, truckloads of rotten chicken
were exposed to formaldehyde in which "a large network," including 11
slaughterhouses run by a criminal gang, were implicated. In 2012,
1 billion rupiah (almost USD100,000) of fish imported from
Batam, Indonesia, were found laced with formaldehyde.
Formalin contamination of foods has been reported in Bangladesh, with
stores and supermarkets selling fruits, fishes, and vegetables that
have been treated with formalin to keep them fresh. However, in
Formalin Control Bill was passed in the Parliament of
Bangladesh with a provision of life-term imprisonment as the maximum
punishment and in addition 2,000,000 BDT as fine but not less than
500,000 BDT for importing, production or hoarding of formalin without
^ a b Nomenclature of Organic Chemistry : IUPAC Recommendations
and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of
Chemistry. 2014. p. 908. doi:10.1039/9781849733069-FP001.
^ a b
Formaldehyde (PDF), SIDS Initial Assessment Report,
International Programme on Chemical Safety
^ Spence, Robert, and William Wild. "114. The vapour-pressure curve of
formaldehyde, and some related data." Journal of the Chemical Society
(Resumed) (1935): 506-509
PubChem Compound Database; CID=712". National Center for
Biotechnology Information. Retrieved 2017-07-08.
^ Weast, Robert C., ed. (1981). CRC Handbook of Chemistry and Physics
(62nd ed.). Boca Raton, FL: CRC Press. pp. C–301, E–61.
^ a b c "NIOSH Pocket Guide to Chemical Hazards #0293". National
Institute for Occupational Safety and Health (NIOSH).
^ "NIOSH Pocket Guide to Chemical Hazards #0294". National Institute
for Occupational Safety and Health (NIOSH).
^ a b "Formaldehyde". Immediately Dangerous to Life and Health
Concentrations (IDLH). National Institute for Occupational Safety and
^ a b c d e f Günther Reuss, Walter Disteldorf, Armin Otto Gamer,
Albrecht Hilt "Formaldehyde" in Ullmann's Encyclopedia of Industrial
Chemistry, 2002, Wiley-VCH, Weinheim. doi:10.1002/14356007.a11_619
^ "Formaldehyde", Formaldehyde, 2-Butoxyethanol and
1-tert-Butoxypropan-2-ol (PDF), IARC Monographs on the Evaluation of
Carcinogenic Risks to Humans 88, Lyon, France: International Agency
for Research on Cancer, 2006, pp. 39–325,
ISBN 92-832-1288-6 "
Formaldehyde (gas)", Report on
Carcinogens, Eleventh Edition (PDF), U.S. Department of Health and
Human Services, Public Health Service, National Toxicology Program,
^ a b Harris, Gardiner (10 June 2011). "Government Says 2 Common
Materials Pose Risk of Cancer". New York Times. Retrieved
^ a b
National Toxicology Program
National Toxicology Program (10 June 2011). "12th Report on
Carcinogens". National Toxicology Program. Retrieved 2011-06-11.
^ a b
National Toxicology Program
National Toxicology Program (10 June 2011). "Report On
Carcinogens – Twelfth Edition – 2011" (PDF). National Toxicology
Program. Retrieved 2011-06-11.
^ Merriam-Webster, Merriam-Webster's Collegiate Dictionary,
^ "Review of the
Formaldehyde Assessment in the National Toxicology
Program 12th Report on Carcinogens". p. 91.
^ "Review of the
Formaldehyde Assessment in the National Toxicology
Program 12th Report on Carcinogens". p. 95.
Formaldehyde Is Biodegradable, Quickly Broken Down in the Air By
Sunlight or By
Bacteria in Soil or Water".
Formaldehyde Panel of the
American Chemistry Council. Retrieved 22 April 2017.
^ Zuckerman, B.; Buhl, D.; Palmer, P.; Snyder, L. E. (1970).
"Observation of interstellar formaldehyde". Astrophys. J. 160:
485–506. Bibcode:1970ApJ...160..485Z. doi:10.1086/150449.
^ Mangum, Jeffrey G.; Darling, Jeremy; Menten, Karl M.; Henkel,
Christian (2008). "
Formaldehyde Densitometry of Starburst Galaxies".
Astrophys. J. 673 (2): 832–46. arXiv:0710.2115 .
^ Woon, David E. (2002). "Modeling Gas-Grain Chemistry with Quantum
Chemical Cluster Calculations. I. Heterogeneous Hydrogenation of CO
and H2CO on Icy Grain Mantles". Astrophys. J. 569: 541–48.
^ Zubritsky, Elizabeth; Neal-Jones, Nancy (11 August 2014). "RELEASE
14-038 - NASA's 3-D Study of Comets Reveals Chemical Factory at Work".
NASA. Retrieved 12 August 2014.
^ Cordiner, M.A.; et al. (11 August 2014). "Mapping the Release of
Volatiles in the Inner Comae of Comets
C/2012 F6 (Lemmon)
C/2012 F6 (Lemmon) and C/2012
S1 (ISON) Using the Atacama Large Millimeter/Submillimeter Array". The
Astrophysical Journal. 792 (1): L2. Bibcode:2014ApJ...792L...2C.
doi:10.1088/2041-8205/792/1/L2. Retrieved 12 August 2014.
^ A. Butlerow (1859) "Ueber einige Derivate des Jodmethylens" (On some
derivatives of methylene iodide), Annalen der Chemie und Pharmacie,
vol . 111, pages 242–252. In this paper, Butlerov discovered
formaldehyde, which he called "Dioxymethylen" (methylene dioxide)
[page 247] because his empirical formula for it was incorrect
^ In 1867, A. W. Hofmann first announced to the Royal Prussian Academy
of Sciences the production of formaldehyde by passing methanol vapor
in air over hot platinum wire. See: A. W. Hofmann (14 October 1867)
"Zur Kenntnis des Methylaldehyds" ([Contributions] to our knowledge of
methylaldehyde), Monatsbericht der Königlich Preussischen Akademie
der Wissenschaften zu Berlin (Monthly Report of the Royal Prussian
Academy of Sciences in Berlin), vol. 8, pages 665–669. Reprinted in:
A.W. Hofmann, (1868) "Zur Kenntnis des Methylaldehyds", Annalen der
Chemie und Pharmacie (Annals of Chemistry and Pharmacy), vol. 145, no.
3, pages 357–361.
A.W. Hofmann (1868) "Zur Kenntnis des Methylaldehyds", Journal für
praktische Chemie (Journal for Practical Chemistry), vol. 103, no. 1,
However, it was not until 1869 that Hofmann determined the correct
empirical formula of formaldehyde. See: A.W. Hofmann (5 April 1869)
"Beiträge zur Kenntnis des Methylaldehyds", Monatsbericht der
Königlich Preussischen Akademie der Wissenschaften zu Berlin,
vol. ?, pages 362–372. Reprinted in:
Hofmann, A.W. (1869). "Beiträge zur Kenntnis des Methylaldehyds".
Journal für Praktische Chemie. 107 (1): 414–424.
A.W. Hofmann (1869) "Beiträge zur Kenntnis des Methylaldehyds,"
Berichte der Deutschen Chemischen Gesellschaft (Reports of the German
Chemical Society), vol. 2, pages 152–159.
^ Read, J. (1935). Text-
Book of Organic Chemistry. London: G Bell
^ Bost, R. W.; Constable, E. W. (1936). "sym-Trithiane". Organic
Syntheses. 16: 81. ; Collective Volume, 2, p. 610
^ Gutsche, C. D.; Iqbal, M. (1993). "p-tert-Butylcalixarene".
Organic Syntheses. ; Collective Volume, 8, p. 75
Formaldehyde in Clothing and Textiles FactSheet". NICNAS.
Australian National Industrial Chemicals Notification and Assessment
Scheme. May 2013. Retrieved 12 November 2014.
^ Economic Importance,
Formaldehyde Council. 2009. Accessed on April
^ Schurink, H. B. J. (1925). "Pentaerythritol". Organic Syntheses. 4:
53. ; Collective Volume, 1, p. 425
^ Francis-Floyd, Ruth (April 1996). "Use of
Formalin to Control Fish
Parasites". Institute of Food and Agricultural Sciences, University of
Florida. Archived from the original on May 27, 2012.
^ Center for Disease Control: Vaccines
^ U.S. Government Publishing Office title=§573.460 Formaldehyde
^ Directive 98/8/EC of the European Parliament and of the Council of
16 February 1998 concerning the placing of biocidal products on the
market. OJEU L123, 24.04.1998, pp. 1–63. (consolidated version
to 2008-09-26 (PDF))
Regulation (EC) No 2032/2003 of 4 November 2003 on the
second phase of the 10-year work programme referred to in
Article 16(2) of Directive 98/8/EC of the European
Parliament and of the Council concerning the placing of biocidal
products on the market, and amending Regulation (EC)
No 1896/2000. OJEU L307, 24.11.2003, p. 1–96.
(consolidated version to 2007-01-04 (PDF))
^ Patel, Alkesh (2007-07-04). "
Formaldehyde Ban set for 22 September
2007". WebWire. Retrieved 19 May 2012.
^ "European chemical Substances Information System (ESIS) entry for
formaldehyde". Archived from the original on 2014-01-01. Retrieved
^ "Process C-41 Using Kodak Flexicolor Chemicals – Publication
Z-131". Kodak. Retrieved 2009-09-01.
^ "Medical Management Guidelines for Formaldehyde".
^ "Indoor Air
Pollution in California" (PDF). Air Resources Board,
California Environmental Protection Agency. July 2005.
pp. 65–70. Retrieved 19 May 2012.
^ "Formaldehyde". Occupational Safety and Health Administration.
August 2008. Retrieved 2009-09-01.
Formaldehyde Reference Exposure Levels" (PDF). California Office Of
Health Hazard Assessment. December 2008. Retrieved 19 May 2012.
Formaldehyde and Indoor Air. Health Canada. August 2005.
ISBN 0-8155-1129-9. Retrieved 2009-09-01.
^ Broder, I; Corey, P; Brasher, P; Lipa, M; Cole, P (1991).
Formaldehyde exposure and health status in households". Environmental
Health Perspectives. 95: 101–4. doi:10.1289/ehp.9195101.
PMC 1568408 . PMID 1821362.
^ McGwin, G; Lienert, J; Kennedy, JI (November 2009). "Formaldehyde
Asthma in Children: A Systematic Review". Environmental
Health Perspectives. Environmental Health Perspectives. 118 (3):
313–7. doi:10.1289/ehp.0901143. PMC 2854756 .
^ "Role of mitochondrial processes in the development and aging of
organism. Aging and cancer" (PDF). Deposited Doc., VINITI 2172-78.
^ "IARC Monographs on the Evaluation of Carcinogenic Risks to Humans
Volume 88 (2006) Formaldehyde, 2-Butoxyethanol and
1-tert-Butoxypropan-2-ol" (pdf, html).
WHO Press, 2006( English
^ a b "
Formaldehyde and Cancer Risk".
^ Zhang, Luoping; Steinmaus, Craig; Eastmond, Eastmond; Xin, Xin;
Smith, Smith (March–June 2009). "
Formaldehyde exposure and leukemia:
A new meta-analysis and potential mechanisms" (PDF). Mutation
Research/Reviews in Mutation Research. Mutation Research/Reviews in
Mutation Research. 681 (2–3): 150–168.
doi:10.1016/j.mrrev.2008.07.002. PMID 18674636. Retrieved
Formaldehyde and Leukemia: Epidemiology, Potential Mechanisms, and
Implications for Risk Assessment". Environmental and Molecular
Mutagenesis. Environmental and Molecular Mutagenesis. 51: 181–191.
^ "What are the key statistics about nasopharyngeal cancer?".
^ Turner JH, Reh DD (June 2012). "Incidence and survival in patients
with sinonasal cancer: a historical analysis of population-based
data". Head Neck. 34 (6): 877–85. doi:10.1002/hed.21830.
^ "What are the key statistics about chronic myeloid leukemia?".
^ "What are the key statistics about acute myeloid leukemia?".
^ a b "What are the risk factors for nasopharyngeal cancer?".
^ Butticè, Claudio (2015). "Solvents". In Colditz, Graham A. The SAGE
Encyclopedia of Cancer and Society (Second ed.). Thousand Oaks: SAGE
Publications, Inc. pp. 1089–1091.
doi:10.4135/9781483345758.n530. ISBN 9781483345734.
^ "What are the risk factors for acute myeloid leukemia?".
^ "What are the risk factors for chronic myeloid leukemia?".
^ Dales, R; Liu, L; Wheeler, AJ; Gilbert, NL (July 2008). "Quality of
indoor residential air and health". Canadian Medical Association
Journal. Canadian Medical Association Journal. 179 (2): 147–52.
doi:10.1503/cmaj.070359. PMC 2443227 .
^ Passmore, Whitney; Sullivan, Michael J. (August 4, 2016). "EPA
Issues Final Rule on
Formaldehyde Emission Standards for Composite
Wood Products". The National Law Review. Womble Carlyle Sandridge
& Rice, PLLC. Retrieved August 24, 2016 – via Google News.
^ "Testing for Indoor Air Quality, Baseline IAQ, and Materials".
Environmental Protection Agency. Archived from the original on October
^ Residential Indoor Air
Formaldehyde Testing Program: A Pilot Study,"
M. Koontz, et al, prepared for U.S. EPA, 1996
^ Evans, Ben (2008-04-11). "FEMA limits formaldehyde in trailers".
Boston.com. Archived from the original on June 15, 2010. Retrieved
^ Zug KA, Warshaw EM, Fowler JF Jr, Maibach HI, Belsito DL, Pratt MD,
Sasseville D, Storrs FJ, Taylor JS, Mathias CG, Deleo VA, Rietschel
RL, Marks J. Patch-test results of the North American Contact
Dermatitis Group 2005–2006. Dermatitis. 2009 May–Jun;20(3):149-60.
Formaldehyde allergy". DermNet NZ. New Zealand Dermatological
Society. June 2009. Retrieved 2009-09-01.
^ a b De Groot, Anton C; Flyvholm, Mari-Ann; Lensen, Gerda; Menné,
Torkil; Coenraads, Pieter-Jan (2009). "Formaldehyde-releasers:
relationship to formaldehyde contact allergy. Contact allergy to
formaldehyde and inventory of formaldehyde-releasers". Contact
Dermatitis. 61 (2): 63–85. doi:10.1111/j.1600-0536.2009.01582.x.
Formaldehyde CAS 50-00-0 (PDF)
Formaldehyde and Facts About Health Effects (PDF). Formaldehyde
Epidemiology, Toxicology and Environmental Group. August 2002.
Accessed on April 25, 2010.
^ When Sampling Formaldehyde, The Medium Matters
^ NIOSH Pocket Gide to Chemical Hazards: Formaldehyde
^ Addendum to the 12th Report on Carcinogens (PDF) National Toxicology
Program, U.S. Department of Health and Human Services, retrieved
^ "European Union Bans formaldehyde/formalin within Europe" (PDF).
European Commission's Environment Directorate-General. September 2007.
pp. 1–3. Retrieved 19 May 2012.
^ "ESIS (European Chemical Substances Information System)". European
Commission Joint Research Centre Institute for Health and Consumer
Protection. February 2009. Archived from the original on 1 January
2014. Retrieved 19 May 2012.
^ "S.1660 –
Formaldehyde Standards for Composite Wood Products Act".
OpenCongress. July 2010. Retrieved 19 May 2012.
^ "Health Canada – Proposed residential indoor air quality
guidelines for formaldehyde". Health Canada. April 2007.
^ CFC.gov (PDF)
Formaldehyde Levels in FEMA-Supplied Trailers (PDF)
^ Mike Brunker (2006-07-25). "Are FEMA trailers 'toxic tin cans'?".
MSNBC. Retrieved 19 May 2012.
^ ATSDR – Minimal Risk Levels for Hazardous Substances (MRLs)
^ FEMA: CDC Releases Results Of
Formaldehyde Level Tests
^ Kunzelman, Michael (2007-08-08). "Suit Filed Over FEMA Trailer
Toxins". The Washington Post. Retrieved 2010-05-02.
^ Brunker, Mike (September 28, 2012). "Class-action suit against FEMA
trailer manufacturers settled for $42.6 million". NBC News. Retrieved
11 September 2015.
^ Megan Terlecky (2008-10-24). "How We Tested for Formaldehyde".
KGAN-TV. Archived from the original on June 15, 2011.
^ "FEMA Trailers in Iowa Exceed
Formaldehyde Levels Considered Safe".
Insurance Journal. October 23, 2008. Retrieved 16 September
^ Nigel Duara (2008-10-21). "FEMA disputes formaldehyde study of Iowa
trailers". Associated Press. Archived from the original on October 31,
^ Cindy Hadish (2008-10-24). "FEMA meets with mobile home residents
over health concerns". Cedar Rapids Gazette. Archived from the
original on February 22, 2009.
^ "Formaldehyde-laced foods reemerge in Indonesian markets". August
^ "Formaldehyde-Tainted Rice Drinks Found at
August 22, 2011.
^ "BPOM Uncovers Two Formaldehyde-Tainted Noodle Factories in Bogor".
October 12, 2014.
^ Xiaojiang Tang et al., "
Formaldehyde in China: Production,
consumption, exposure levels, and health effects (PDF)", Environment
International 35 (2009): 1215–16, and other references cited on p.
1216; see also "Municipality sees red over bad blood processing"
(2011-03-18, China Daily, online English edition; retrieved on May 17,
^ Moise Ngwa (2010-10-25). "formaldehyde testing" (PDF). Cedar Rapids
Gazette. Retrieved 19 May 2012.
^ "Was Death in the Milk?". The Indianapolis News. July 31, 1900.
p. 5. Retrieved August 20, 2014 – via Newspapers.com.
^ "Wants New Law Enacted. Food Inspector Farnsworth Would Have Use of
Formaldehyde in Milk Stopped". The Topeka Daily Capital. August 30,
1903. p. 8. Retrieved August 20, 2014 – via
^ Illegal business 'being run by a gang' - The Nation
^ Import of formaldehyde fish from
Pakistan foiled in BatamThe
^ Staff Correspondent, "Trader Fined for Selling Fish Treated with
Formalin," Bangladesh2day, September 1, 2009
Wikisource has the text of the 1911 Encyclopædia Britannica article
International Chemical Safety Card 0275 (gas)
International Chemical Safety Card 0695 (solution)
"NIOSH Pocket Guide to Chemical Hazards #0293". National Institute for
Occupational Safety and Health (NIOSH).
Entry for "Formaldehyde" on the Australian National Pollutant
Formaldehyde from ChemSub Online
Formaldehyde in the Workplace (PDF) from the IRSST
Formaldehyde from the National Institute for Occupational Safety and
IPCS Health and Safety Guide 57: Formaldehyde
Environmental Health Criteria 89: Formaldehyde
SIDS Initial Assessment Report for
Formaldehyde from the Organisation
for Economic Co-operation and Development (OECD)
Formaldehyde Added to "Known Carcinogens" List Despite Lobbying by
Chemical Industry — video report by Democracy Now!
Do you own a post-Katrina FEMA trailer? Check your VIN#
So you’re living in one of FEMA’s Katrina trailers... What can you
Formaldehyde in the
Pesticide Properties DataBase (PPDB)
Adulterants, food contaminants
Mercury in fish
Monosodium glutamate (MSG)
High-fructose corn syrup
Escherichia coli O104:H4
Escherichia coli O157:H7
Parasitic infections through food
Ethylenediaminetetraacetic acid (EDTA)
Toxins, poisons, environment pollution
Arsenic contamination of groundwater
Benzene in soft drinks
Food contamination incidents
Swill milk scandal
1858 Bradford sweets poisoning
1900 English beer poisoning
Morinaga Milk arsenic poisoning incident
1971 Iraq poison grain disaster
Toxic oil syndrome
1993 Jack in the Box E. coli outbreak
1996 Odwalla E. coli outbreak
2006 North American E. coli outbreaks
ICA meat repackaging controversy
2008 Canada listeriosis outbreak
2008 Chinese milk scandal
2008 Irish pork crisis
2008 United States salmonellosis outbreak
2011 Germany E. coli outbreak
2011 Taiwan food scandal
2011 United States listeriosis outbreak
2013 Bihar school meal poisoning
2013 horse meat scandal
2013 Taiwan food scandal
2014 Taiwan food scandal
2017 Brazil weak meat scandal
2017–18 South African listeriosis outbreak
Food safety incidents in China
Regulation, standards, watchdogs
Acceptable daily intake
Food labeling regulations
Food libel laws
International Food Safety Network
Quality Assurance International
Centre for Food Safety
European Food Safety Authority
Institute for Food Safety and Health
International Food Safety Network
Ministry of Food and Drug Safety
Molecules detected in outer space
Magnesium monohydride cation
Hydrogen cyanide (HCN)
Hydrogen isocyanide (HNC)
Protonated molecular hydrogen
Protonated carbon dioxide
Protonated hydrogen cyanide
Buckminsterfullerene (C60 fullerene, buckyball)
Ethyl methyl ether
Atomic and molecular astrophysics
Diffuse interstellar band
Earliest known life forms
Extraterrestrial liquid water
Helium hydride ion
Iron–sulfur world theory
Molecules in stars
Nexus for Exoplanet System Science
PAH world hypothesis
Polycyclic aromatic hydrocarbon
Polycyclic aromatic hydrocarbon (PAH)
RNA world hypothesis
TRP channel modulators
Sanshool (ginger, Sichuan and melegueta peppers)
Allyl isothiocyanate (mustard, radish, horseradish, wasabi)
CR gas (dibenzoxazepine; DBO)
CS gas (2-chlorobenzal malononitrile)
Farnesyl thiosalicylic acid
Ligustilide (celery, Angelica acutiloba)
Linalool (Sichuan pepper, thyme)
Methyl salicylate (wintergreen)
Oleocanthal (olive oil)
Paclitaxel (Pacific yew)
Polygodial (Dorrigo pepper)
Shogaols (ginger, Sichuan and melegueta peppers)
Thiopropanal S-oxide (onion)
Umbellulone (Umbellularia californica)
Adhyperforin (St John's wort)
Hyperforin (St John's wort)
Cooling Agent 10
Rutamarin (Ruta graveolens)
Steviol glycosides (e.g., stevioside) (Stevia rebaudiana)
Sweet tastants (e.g., glucose, fructose, sucrose; indirectly)
Rutamarin (Ruta graveolens)
Triptolide (Tripterygium wilfordii)
Sanshool (ginger, Sichuan and melegueta peppers)
Bisandrographolide (Andrographis paniculata)
Camphor (camphor laurel, rosemary, camphorweed, African blue basil,
Capsaicin (chili pepper)
Carvacrol (oregano, thyme, pepperwort, wild bergamot, others)
Dihydrocapsaicin (chili pepper)
Eugenol (basil, clove)
Evodiamine (Euodia ruticarpa)
Homocapsaicin (chili pepper)
Homodihydrocapsaicin (chili pepper)
Low pH (acidic conditions)
Nonivamide (PAVA) (PAVA spray)
Nordihydrocapsaicin (chili pepper)
Paclitaxel (Pacific yew)
Phorbol esters (e.g., 4α-PDD)
Piperine (black pepper, long pepper)
Polygodial (Dorrigo pepper)
Rutamarin (Ruta graveolens)
Resiniferatoxin (RTX) (Euphorbia resinifera/pooissonii)
Shogaols (ginger, Sichuan and melegueta peppers)
Thymol (thyme, oregano)
Tinyatoxin (Euphorbia resinifera/pooissonii)
Cannabigerolic acid (cannabis)
See also: Receptor/signaling modulators • Ion channel modulators