Formaldehyde

Formaldehyde (/fɔːrˈmældɪhaɪd/ ( listen) for-MAL-di-

hide, US also /fər-/ ( listen) fər-) (systematic name
Formaldehyde
methanal) is a naturally occurring organic compound
with the formula CH2 O and structure H−CHO. The pure
compound is a pungent, colourless gas that polymerises
spontaneously into paraformaldehyde (refer to section
Forms below), hence it is stored as an aqueous solution
(formalin), which is also used to store animal specimens.
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 at 8.7 million tons per year.[14] It is mainly used
in the production of industrial resins, e.g., for particle Names
board and coatings. Preferred IUPAC name
Formaldehyde[1]
Systematic IUPAC name
Contents Methanal[1]
Forms Other names
Structure and bonding Methyl aldehyde
Occurrence Methylene glycol (diol forms in aqueous
Interstellar formaldehyde solution)
Methylene oxide
Synthesis and industrial production
Formalin (aqueous solution)
Laboratory synthesis
Formol
Industry
Carbonyl hydride
In nature
Identifiers
Organic chemistry
CAS Number 50-00-0 (https://common
Self-condensation and hydration
chemistry.cas.org/detail?
Oxidation
cas_rn=50-00-0) 
Hydroxymethylation and chloromethylation
Base reactions 3D model (JSmol) Interactive image (http

Uses s://chemapps.stolaf.edu/j
Industrial applications mol/jmol.php?model=C%
Niche uses 3DO)
Disinfectant and biocide 3DMet B00018 (http://www.3dm
Tissue fixative and embalming agent et.dna.affrc.go.jp/cgi/sho
Drug testing w_data.php?acc=B0001
Photography 8)
 Safety Beilstein 1209228
International bans Reference

Contaminant in food ChEBI CHEBI:16842 (https://ww

See also w.ebi.ac.uk/chebi/searchI
d.do?chebiId=16842) 
References
ChEMBL ChEMBL1255 (https://ww
External links
w.ebi.ac.uk/chembldb/ind
ex.php/compound/inspec
Forms t/ChEMBL1255) 
ChemSpider 692 (https://www.chemsp
Formaldehyde is more complicated than many simple
ider.com/Chemical-Struct
carbon compounds in that it adopts several diverse forms.
ure.692.html) 
These compounds can often be used interchangeably and
can be interconverted. DrugBank DB03843 (https://www.dr
ugbank.ca/drugs/DB038
Molecular formaldehyde. A colorless gas with a
43) 
characteristic pungent, irritating odor. It is stable
at about 150 °C, but polymerizes when ECHA InfoCard 100.000.002 (https://ech
condensed to a liquid. a.europa.eu/substance-i
1,3,5-Trioxane, with the formula (CH2O)3. It is a nformation/-/substancein
white solid that dissolves without degradation in fo/100.000.002)
organic solvents. It is a trimer of molecular
formaldehyde. EC Number 200-001-8
Paraformaldehyde, with the formula E number E240 (preservatives)
HO(CH2O)nH. It is a white solid that is insoluble
Gmelin Reference 445
in most solvents.
Methanediol, with the formula CH2(OH)2. This IUPHAR/BPS 4196 (http://www.guideto
compound also exists in equilibrium with pharmacology.org/GRA
various oligomers (short polymers), depending C/LigandDisplayForwar
on the concentration and temperature. A d?tab=summary&ligandI
saturated water solution, of about 40% d=4196)
formaldehyde by volume or 37% by mass, is
called "100% formalin". KEGG D00017 (https://www.keg
g.jp/entry/D00017) 
A small amount of stabilizer, such as methanol, is usually
MeSH Formaldehyde (https://w
added to suppress oxidation and polymerization. A
typical commercial-grade formalin may contain 10–12% ww.nlm.nih.gov/cgi/mes
methanol in addition to various metallic impurities. h/2014/MB_cgi?mode=&t
erm=Formaldehyde)
"Formaldehyde" was first used as a generic trademark in PubChem CID 712 (https://pubchem.nc
1893 following a previous trade name, "formalin".[15]
bi.nlm.nih.gov/compoun
Main forms of formaldehyde d/712)
RTECS number LP8925000
UNII 1HG84L3525 (https://fda
sis.nlm.nih.gov/srs/srsdir
ect.jsp?regno=1HG84L3
525) 
UN number 2209
 CompTox DTXSID7020637 (https://
Dashboard (EPA) comptox.epa.gov/dashbo
ard/chemical/details/DTX
SID7020637)

InChI
InChI=1S/CH2O/c1-2/h1H2 
Key: WSFSSNUMVMOOMR-UHFFFAOYSA-
N 
Monomeric Trioxane is a stable
InChI=1/CH2O/c1-2/h1H2
formaldehyde cyclic trimer of Key: WSFSSNUMVMOOMR-UHFFFAOYAT
(subject of this formaldehyde.
article). SMILES
C=O

Properties[7]
Chemical formula CH2O
Molar mass 30.026 g·mol−1
Appearance Colorless gas
Density 0.8153 g/cm3 (−20 °C)[2]
(liquid)
Melting point −92 °C (−134 °F; 181 K)
Paraformaldehyde is Methanediol, the
a common form of predominant Boiling point −19 °C (−2 °F; 254 K)[2]
formaldehyde for species in dilute Solubility in water 400 g/L
industrial aqueous solutions of
log P 0.350
applications. formaldehyde.
Vapor pressure > 1 atm[3]
Acidity (pKa) 13.27 (hydrate)[4][5]

Structure and bonding Magnetic −18.6·10−6 cm3/mol

susceptibility (χ)
Molecular formaldehyde contains a central carbon atom Dipole moment 2.330 D[6]
with a double bond to the oxygen atom and a single bond Structure
to each hydrogen atom. This structure is summarised by
Point group C2v
the condensed formula H2 C=O.[16] The molecule is
planar, Y-shaped and its molecular symmetry belongs to Molecular shape Trigonal planar
the C2v point group.[17] The precise molecular geometry Thermochemistry[8]
of gaseous formaldehyde has been determined by gas Heat capacity (C) 35.387 J·mol−1·K−1
electron diffraction[16][18] and microwave
[19][20] Std molar 218.760 J·mol−1·K−1
spectroscopy. The bond lengths are 1.21 Å for the
entropy (S ⦵298)
carbon–oxygen bond[16][18][19][20][21] and around 1.11
Å for the carbon–hydrogen bond,[16][18][19][20] while the Std enthalpy of −108.700 kJ·mol−1
formation
H–C–H bond angle is 117°,[19][20] close to the 120°
(Δ f H ⦵298)
Gibbs free energy −102.667 kJ·mol−1
(Δ f G⦵)
angle found in an ideal trigonal planar molecule.[16] Std enthalpy of 571 kJ·mol−1
Some excited electronic states of formaldehyde are combustion
pyramidal rather than planar as in the ground state.[21] (Δ c H ⦵298)
Pharmacology
Occurrence ATCvet code QP53AX19 (WHO (http
s://www.whocc.no/atcvet/
Processes in the upper atmosphere contribute up to 90% atcvet_index/?code=QP5
of the total formaldehyde in the environment.
3AX19))
Formaldehyde is an intermediate in the oxidation (or
combustion) of methane, as well as of other carbon Hazards
compounds, e.g. in forest fires, automobile exhaust, and GHS labelling:
tobacco smoke. When produced in the atmosphere by the
Pictograms
action of sunlight and oxygen on atmospheric methane
and other hydrocarbons, it becomes part of smog.
Formaldehyde has also been detected in outer space. [9]

Signal word Danger

Formaldehyde and its adducts are ubiquitous in living
organisms. It is formed in the metabolism of the amino Hazard H301, H311, H314,
acids serine and threonine and is found in the statements H317, H331, H335,
bloodstream of humans and other primates at H341, H350, H370[9]
concentrations of approximately 0.1  millimolar.[22] Precautionary P201, P280,
Experiments in which animals are exposed to an statements P303+P361+P353,
atmosphere containing isotopically labeled formaldehyde
have demonstrated that even in deliberately exposed P304+P340+P310,
animals, the majority of formaldehyde-DNA adducts P305+P351+P338,
found in non-respiratory tissues are derived from P308+P310[9]
endogenously produced formaldehyde.[23] NFPA 704
(fire diamond) 4
Formaldehyde does not accumulate in the environment, 3 0
because it is broken down within a few hours by sunlight COR
or by bacteria present in soil or water. Humans
metabolize formaldehyde quickly, converting it to formic Flash point 64 °C (147 °F; 337 K)
acid, so it does not accumulate in the body.[24] It Autoignition 430 °C (806 °F; 703 K)
nonetheless presents significant health concerns. temperature
Explosive limits 7–73%
Interstellar formaldehyde Lethal dose or concentration (LD, LC):
LD50 (median 100 mg/kg (oral, rat)[12]
Formaldehyde appears to be a useful probe in dose)
astrochemistry due to prominence of the 110 ←111 and
LC50 (median 333 ppm (mouse, 2 h)
211 ←212 K-doublet transitions. It was the first concentration) 815 ppm (rat, 30 min)[13]
polyatomic organic molecule detected in the interstellar
medium.[25] Since its initial detection in 1969, it has been LCLo (lowest 333 ppm (cat, 2 h)[13]
observed in many regions of the galaxy. Because of the published)
widespread interest in interstellar formaldehyde, it has NIOSH (US health exposure limits):
been extensively studied, yielding new extragalactic PEL TWA 0.75 ppm ST 2 ppm
sources.[26] A proposed mechanism for the formation is (Permissible) (as formaldehyde and
the hydrogenation of CO ice:[27] formalin)[10][11]
H + CO → HCO REL Ca TWA 0.016 ppm C
HCO + H → CH2O (Recommended) 0.1 ppm [15-minute][10]
HCN, HNC, H2 CO, and dust have also been observed IDLH Ca [20 ppm][10]
inside the comae of comets C/2012 F6 (Lemmon) and (Immediate
C/2012 S1 (ISON).[28][29] danger)
Safety data sheet MSDS (https://www.fisher

Synthesis and industrial (SDS) sci.com/shop/msdsprox

y?productName=F75P1
production GAL&productDescription
=formaldehyde--by-weig
ht-histological-fisher-che
Laboratory synthesis mical&catNo=F75P-1GA
L&vendorId=VN0000000
Formaldehyde was first reported in 1859 by the Russian
1&storeId=10652)
chemist Aleksandr Butlerov (1828–86)[30] In his paper,
(Archived (https://web.ar
Butlerov referred to formaldehyde as "dioxymethylen"
(methylene dioxide) [page 247] because his empirical chive.org/web/20170918
formula for it was incorrect (C4 H4 O4 ). It was 021414/https://www.fishe
conclusively identified by August Wilhelm von rsci.com/shop/msdsprox
Hofmann, who first announced the production of y?productName=F75P1
formaldehyde by passing methanol vapor in air over hot GAL&productDescription
platinum wire.[31][32] With modifications, Hoffmann's =formaldehyde--by-weig
method remains the basis of the present day industrial ht-histological-fisher-che
route. mical&catNo=F75P-1GA
L&vendorId=VN0000000
Solution routes to formaldehyde also entail oxidation of
1&storeId=10652))
methanol or methyl iodide.[33]
Related compounds
Related Acetaldehyde
Industry aldehydes
Butyraldehyde
Formaldehyde is produced industrially by the catalytic Decanal
oxidation of methanol. The most common catalysts are Heptanal
silver metal, iron(III) oxide,[34] iron molybdenum oxides Hexanal
[e.g. iron(III) molybdate] with a molybdenum-enriched Nonanal
surface,[35] or vanadium oxides. In the commonly used Octadecanal
formox process, methanol and oxygen react at ca.  250– Octanal
400  °C in presence of iron oxide in combination with Pentanal
molybdenum and/or vanadium to produce formaldehyde Propionaldehyde
according to the chemical equation:[14]
Related Methanol
2 CH3OH + O2 → 2 CH2O + 2 H2O compounds Formic acid
The silver-based catalyst usually operates at a higher Except where otherwise noted, data are
temperature, about 650 °C. Two chemical reactions on it given for materials in their standard state (at
simultaneously produce formaldehyde: that shown above 25 °C [77 °F], 100 kPa).
and the dehydrogenation reaction:  verify (what is   ?)
Infobox references
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.[14]

In nature

The amino acid serine is a source of natural formaldehyde according to this reaction, which produces
glycine:

HOCH2CH(NH2)CO2H → CH2O +H2C(NH2)CO2H

This reaction is catalyzed by serine hydroxymethyltransferase, a PLP-containing enzyme.

Organic chemistry
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 1,3,5-trioxane, and the
polymer is called paraformaldehyde. Many cyclic oligomers have been isolated. Similarly, formaldehyde
hydrates to give the geminal diol methanediol, which condenses further to form oligomers HO(CH2 O)n H.
Monomeric CH2 O is rarely encountered.

Oxidation

It is readily oxidized by atmospheric oxygen into formic acid. For this reason, commercial formaldehyde is
typically contaminated with formic acid.

Hydroxymethylation and chloromethylation

Formaldehyde reacts with many compounds, resulting in hydroxymethylation:

X-H + CH2O → X-CH2OH

(X = R2 N, RC(O)NR', SH). The resulting hydroxymethyl derivatives typically react further. Thus, amines
give hexahydro-1,3,5-triazines:

3 RNH2 + 3 CH2O → (RNCH2)3 + 3 H2O

Similarly, when combined with hydrogen sulfide, it forms trithiane:[36]

3 CH2O + 3 H2S → (CH2S)3 + 3 H2O

In the presence of acids, it participates in electrophilic aromatic substitution reactions with aromatic
compounds resulting in hydroxymethylated derivatives:

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.[37] Phenol results in polymers.

Base reactions

Cannizzaro reaction in the presence of basic catalysts to produce formic acid and methanol.

Uses

Industrial applications

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.[14] The textile industry uses formaldehyde-based resins as finishers to make fabrics
crease-resistant.[38]

When treated with phenol, urea, or melamine,

formaldehyde produces, respectively, hard
thermoset phenol formaldehyde resin, urea
formaldehyde resin, and melamine resin. These
polymers are permanent adhesives used in
plywood and carpeting. They are also foamed to
make insulation, or cast into moulded products.
Production of formaldehyde resins accounts for
more than half of formaldehyde consumption.
Two steps in formation of urea-formaldehyde resin, which
Formaldehyde is also a precursor to is widely used in the production of particle board.
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 RDX.

Condensation with acetaldehyde affords pentaerythritol, a chemical necessary in synthesizing PETN, a

high explosive.[39] Condensation with phenols gives phenol-formaldehyde resins.

Niche uses

Disinfectant and biocide

An aqueous solution of formaldehyde can be useful as a disinfectant as it kills most bacteria and fungi
(including their spores). It is used as an additive in vaccine manufacturing to inactivate toxins and
pathogens.[40] Formaldehyde releasers are used as biocides in personal care products such as cosmetics.
Although present at levels not normally considered harmful, they are known to cause allergic contact
dermatitis in certain sensitised individuals.[41]

Aquarists use formaldehyde as a treatment for the parasites Ichthyophthirius multifiliis and Cryptocaryon
irritans.[42]

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.[43]

Tissue fixative and embalming agent

Formaldehyde preserves or fixes tissue or cells. The process

involves cross-linking of primary amino groups. The European
Union has banned the use of formaldehyde as a biocide (including
embalming) under the Biocidal Products Directive (98/8/EC) due to
its carcinogenic properties.[44][45] Countries with a strong tradition
of embalming corpses, such as Ireland and other colder-weather
countries, have raised concerns. Despite reports to the contrary,[46]
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.[47]

Formaldehyde-based crosslinking is exploited in ChIP-on-chip or

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 Injecting a giant squid specimen with
RNA gel electrophoresis, preventing RNA from forming secondary formalin for preservation
structures. A solution of 4% formaldehyde fixes pathology tissue
specimens at about one mm per hour at room temperature.

Drug testing

Formaldehyde and an 18  M (concentrated) sulfuric acid makes Marquis reagent—which can identify
alkaloids and other compounds.

Photography

In photography, formaldehyde is used in low concentrations for the process C-41 (color negative film)
stabilizer in the final wash step,[48] as well as in the process E-6 pre-bleach step, to make it unnecessary in
the final wash.

Safety
In view of its widespread use, toxicity, and volatility, formaldehyde poses a significant danger to human
health.[49][50] In 2011, the US National Toxicology Program described formaldehyde as "known to be a
human carcinogen".[51][52][53]

However, concerns are associated with chronic (long term) exposure by inhalation as may happen from
thermal or chemical decomposition of formaldehyde-based resins 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.[54] At concentrations above 0.1  ppm in air, formaldehyde can irritate the eyes and mucous
membranes.[55] Formaldehyde inhaled at this concentration may cause headaches, a burning sensation in
the throat, and difficulty breathing, and can trigger or aggravate asthma symptoms.[56][57]

The CDC considers formaldehyde as a systemic poison. Formaldehyde poisoning can cause permanent
changes in the nervous system's functions.[58]

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.[59] A 2009 review of studies
has shown a strong association between exposure to formaldehyde and the development of childhood
asthma.[60]

A theory was proposed for the carcinogenesis of formaldehyde in 1978.[61] In 1987 the United States
Environmental Protection Agency (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[62] associated with nasal sinus cancer and
nasopharyngeal cancer.[63] 2009 and 2010 studies have also shown a positive correlation between exposure
to formaldehyde and the development of leukemia, particularly myeloid leukemia.[64][65] Nasopharyngeal
and sinonasal cancers are relatively rare, with a combined annual incidence in the United States of < 4,000
cases.[66][67] About 30,000 cases of myeloid leukemia occur in the United States each year.[68][69] Some
evidence suggests that workplace exposure to formaldehyde contributes to sinonasal cancers.[70]
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.[71] Other factors are important in determining individual risk for the development of leukemia
or nasopharyngeal cancer.[70][72][73] In yeast, formaldehyde is found to perturb pathways for DNA repair
and cell cycle.[74]

In the residential environment, formaldehyde exposure comes from a number of routes; formaldehyde can
be emitted by treated wood products, such as plywood or particle board, but it is produced by paints,
varnishes, floor finishes, and cigarette smoking as well.[75] In July 2016, the U.S. EPA released a
prepublication version of its final rule on Formaldehyde Emission Standards for Composite Wood
Products.[76] These new rules impact manufacturers, importers, distributors, and retailers of products
containing composite wood, including fiberboard, particleboard, and various laminated products, who must
comply with more stringent record-keeping and labeling requirements.[77]

The U.S. EPA allows no more than 0.016 ppm formaldehyde in the air in new buildings constructed for
that agency.[78] 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.[79] The Federal Emergency Management Agency (FEMA)
has also announced limits on the formaldehyde levels in trailers purchased by that agency.[80] 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.[63]
For most people, irritation from formaldehyde is temporary and
reversible, although 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%).[81] People with
formaldehyde allergy are advised to avoid formaldehyde releasers
as well (e.g., Quaternium-15, imidazolidinyl urea, and diazolidinyl
urea).[82] 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 Patch test
dermatitis on the face (typically from cosmetics).[41] Formaldehyde
has been banned in cosmetics in both Sweden and Japan.[83] The
eyes are most sensitive to formaldehyde exposure: The lowest level at which many people can begin to
smell formaldehyde ranges between 0.05-1 ppm. The maximum concentration value at the workplace is 0.3
ppm.[84] 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.[85]

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. Formaldehyde emits 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 off-gas. Formaldehyde levels decrease
over time as the sources suppress.

Formaldehyde levels in air can be sampled and tested in several ways,

including impinger, treated sorbent, and passive monitors.[86] The National
Institute for Occupational Safety and Health (NIOSH) has measurement Some air purifiers include
methods numbered 2016, 2541, 3500, and 3800.[87] filtering technology that is
supposed to lower indoor
Studies on the interactions between formaldehyde and proteins at the formaldehyde concentration.
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 causes 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 NO3 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 stress.
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."[51][52][53] Concurrently, a National Academy of Sciences (NAS)
committee was convened and issued an independent review of the draft U.S. EPA IRIS assessment of
formaldehyde, providing a comprehensive health effects assessment and quantitative estimates of human
risks of adverse effects.[88]

Formaldehyde occurs naturally, and is "an essential intermediate in cellular metabolism in mammals and
humans."[14] "Formaldehyde is found in every living system -- from plants to animals to humans. It
metabolizes quickly in the body, breaks down rapidly, is not persistent and does not accumulate in the
body."[89]

International bans

Several web articles claim 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. That is a misconception, as 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.[90][91] 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.[41]

In the United States, Congress passed a bill 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 0.09 ppm, and required companies to meet this
standard by January 2013.[92] The final U.S. EPA rule specified maximum emissions of "0.05 ppm
formaldehyde for hardwood plywood, 0.09 ppm formaldehyde for particleboard, 0.11 ppm formaldehyde
for medium-density fiberboard, and 0.13 ppm formaldehyde for thin medium-density fiberboard."[93]

Formaldehyde was declared a toxic substance by the 1999 Canadian Environmental Protection Act.[94]

External media
Contaminant in food
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.[95] In
August 2011, at least at two Carrefour supermarkets, the Central Audio
Jakarta Livestock and Fishery Sub-Department found cendol "Episode 202: Where Have All
containing 10 parts per million of formaldehyde.[96] In 2014, the the FEMA Trailers Gone? Tracing
owner of two noodle factories in Bogor, Indonesia, was arrested Toxicity from Bust to Boom" (https://
for using formaldehyde in noodles. 50  kg of formaldehyde was www.sciencehistory.org/distillations/
confiscated.[97] Foods known to be contaminated included podcast/where-have-all-the-fema-tr
noodles, salted fish, and tofu. Chicken and beer were also
ailers-gone), Distillations,
rumored to be contaminated. In some places, such as China,
September 2, 2015, Science History
manufacturers still use formaldehyde illegally as a preservative in
Institute
foods, which exposes people to formaldehyde ingestion.[98] In
humans, the ingestion of formaldehyde has been shown to cause Video
vomiting, abdominal pain, dizziness, and in extreme cases can
Where Have All the Trailers
cause death.[58] Testing for formaldehyde is by blood and/or
Gone? (https://www.sciencehistory.
urine by gas chromatography-mass spectrometry. Other methods
include infrared detection, gas detector tubes, etc., of which high- org/distillations/video/where-have-al
performance liquid chromatography is the most sensitive.[99] In l-the-trailers-gone), Video by Mariel
the early 1900s, it was frequently added by US milk plants to Carr (Videographer) & Nick Shapiro
milk bottles as a method of pasteurization due to the lack of (Researcher), 2015, Science
knowledge and concern[100] regarding formaldehyde's History Institute
toxicity.[101][102]

In 2011 in Nakhon Ratchasima, Thailand, truckloads of rotten chicken were treated with formaldehyde for
sale in which "a large network," including 11 slaughterhouses run by a criminal gang, were implicated.[103]
In 2012, 1 billion rupiah (almost US$100,000) of fish imported from Pakistan to Batam, Indonesia, were
found laced with formaldehyde.[104]

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.[105] However, in
2015, a Formalin Control Bill was passed in the Parliament of Bangladesh with a provision of life-term
imprisonment as the maximum punishment as well as a maximum fine of 2,000,000 BDT but not less than
500,000 BDT for importing, producing, or hoarding formalin without a license.[106]

Formaldehyde was one of the chemicals used in 19th century industrialised food production that was
investigated by Dr. Harvey W. Wiley with his famous 'Poison Squad' as part of the US Department of
Agriculture. This led to the 1906 Pure Food and Drug Act, a landmark event in the early history of food
regulation in the United States.

See also
Transition metal complexes of aldehydes and ketones includes several complexes of
formaldehyde.
1,3-Dioxetane
DMDM hydantoin
Sulphobes

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External links
International Chemical Safety Card 0275 (https://www.ilo.org/dyn/icsc/showcard.display?p_l
ang=en&p_card_id=0275&p_version=2) (gas)
International Chemical Safety Card 0695 (https://www.ilo.org/dyn/icsc/showcard.display?p_l
ang=en&p_card_id=0695&p_version=2) (solution)
NIOSH Pocket Guide to Chemical Hazards. "#0293" (https://www.cdc.gov/niosh/npg/npgd02
93.html). National Institute for Occupational Safety and Health (NIOSH).
Entry for "Formaldehyde" (http://www.npi.gov.au/database/substance-info/profiles/45.html)
on the Australian National Pollutant Inventory
Formaldehyde (http://chemsub.online.fr/name/formaldehyde.html) from ChemSub Online
Prevention guide—Formaldehyde in the Workplace (PDF) (http://www.irsst.qc.ca/files/docu
ments/PubIRSST/RG-473.pdf) from the IRSST
Formaldehyde (https://www.cdc.gov/niosh/topics/formaldehyde/) from the National Institute
for Occupational Safety and Health
IPCS Health and Safety Guide 57: Formaldehyde (http://www.inchem.org/documents/hsg/hs
g/hsg057.htm)
IPCS Environmental Health Criteria 89: Formaldehyde (http://www.inchem.org/documents/e
hc/ehc/ehc89.htm)
 SIDS Initial Assessment Report for Formaldehyde (http://www.inchem.org/documents/sids/si
ds/FORMALDEHYDE.pdf) from the Organisation for Economic Co-operation and
Development (OECD)
Formaldehyde Added to "Known Carcinogens" List Despite Lobbying by Chemical Industry
(http://www.democracynow.org/2011/6/14/formaldehyde_added_to_known_carcinogens_lis
t) — video report by Democracy Now!
Do you own a post-Katrina FEMA trailer? Check your VIN# (http://assets.grist.org/article/peo
ple-are-still-living-in-femas-toxic-katrina-trailers-and-they-likely-have-no-idea/index.html)
So you’re living in one of FEMA’s Katrina trailers... What can you do? (http://grist.org/article/
what-do-i-do-if-i-am-living-in-a-fema-trailer/)
Formaldehyde (http://sitem.herts.ac.uk/aeru/ppdb/en/Reports/359.htm) in the Pesticide
Properties DataBase (PPDB)

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