Physics:Formaldehyde

From HandWiki
Short description: Organic compound (H–CHO); simplest aldehyde
Formaldehyde
Structural formula of formaldehyde (with hydrogens)
Spacefill model of formaldehyde
Ball and stick model of formaldehyde
Names
Preferred IUPAC name
Formaldehyde[1]
Systematic IUPAC name
Methanal[1]
Other names
Methyl aldehyde
Methylene glycol (diol forms in aqueous solution)
Methylene oxide
Formalin (aqueous solution)
Formol
Carbonyl hydride
Methanone
Oxomethane
Identifiers
3D model (JSmol)
3DMet
1209228
ChEBI
ChEMBL
ChemSpider
DrugBank
EC Number
  • 200-001-8
445
KEGG
MeSH Formaldehyde
RTECS number
  • LP8925000
UNII
UN number 2209
Properties[7]
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)
Boiling point −19 °C (−2 °F; 254 K)[2]
400 g/L
log P 0.350
Vapor pressure > 1 atm[3]
Acidity (pKa) 13.27 (hydrate)[4][5]
−18.6·10−6 cm3/mol
2.330 D[6]
Structure
C2v
Trigonal planar
Thermochemistry[8]
35.387 J·mol−1·K−1
218.760 J·mol−1·K−1
−108.700 kJ·mol−1
−102.667 kJ·mol−1
571 kJ·mol−1
Pharmacology
1=ATCvet code} QP53AX19 (WHO)
Hazards
Safety data sheet MSDS(Archived)
GHS pictograms GHS06: Toxic GHS05: Corrosive GHS08: Health hazard[9]
GHS Signal word Danger
H301, H311, H331, H314, H317, H335, H341, H350, H370[9]
P201, P280, P303+361+353, P304+340+310, P305+351+338, P308+310Script error: No such module "Preview warning".Category:GHS errors[9]
NFPA 704 (fire diamond)
Flash point 64 °C (147 °F; 337 K)
430 °C (806 °F; 703 K)
Explosive limits 7–73%
Lethal dose or concentration (LD, LC):
100 mg/kg (oral, rat)[12]
333 ppm (mouse, 2 h)
815 ppm (rat, 30 min)[13]
333 ppm (cat, 2 h)[13]
NIOSH (US health exposure limits):
PEL (Permissible)
TWA 0.75 ppm ST 2 ppm (as formaldehyde and formalin)[10][11]
REL (Recommended)
Ca TWA 0.016 ppm C 0.1 ppm [15-minute][10]
IDLH (Immediate danger)
Ca [20 ppm][10]
Related compounds
Related aldehydes
Acetaldehyde

Butyraldehyde
Decanal
Heptanal
Hexanal
Nonanal
Octadecanal
Octanal
Pentanal
Propionaldehyde

Related compounds
Methanol
Formic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☑Y verify (what is ☑Y☒N ?)
Infobox references
Tracking categories (test):

Formaldehyde (/fɔːrˈmældɪhd/ (About this soundlisten) for-MAL-di-hide, US also /fər-/ (About this soundlisten) fər-) (systematic name methanal) is an organic compound with the formula CH
2
O
and structure H–CHO. The compound is a pungent, colourless gas that polymerises spontaneously into paraformaldehyde. It is stored as aqueous solutions (formalin), which consists mainly of the hydrate CH2(OH)2. It is the simplest of the aldehydes (R–CHO). As a precursor to many other materials and chemical compounds, in 2006 the global production of formaldehyde was estimated at 12 million tons per year.[14] It is mainly used in the production of industrial resins, e.g., for particle board and coatings. Small amounts also occur naturally.

Formaldehyde is classified as a carcinogen[note 1] and can cause respiratory and skin irritation upon exposure.[15]

Forms

Formaldehyde is more complicated than many simple carbon compounds in that it adopts several diverse forms. These compounds can often be used interchangeably and can be interconverted.

  • Molecular formaldehyde. A colorless gas with a characteristic pungent, irritating odor. It is stable at about 150 °C, but polymerizes when condensed to a liquid.
  • 1,3,5-Trioxane, with the formula (CH2O)3. It is a white solid that dissolves without degradation in organic solvents. It is a trimer of molecular formaldehyde.
  • Paraformaldehyde, with the formula HO(CH2O)nH. It is a white solid that is insoluble in most solvents.
  • Methanediol, with the formula CH2(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.

"Formaldehyde" was first used as a generic trademark in 1893 following a previous trade name, "formalin".[16]

Structure and bonding

Molecular formaldehyde contains a central carbon atom with a double bond to the oxygen atom and a single bond to each hydrogen atom. This structure is summarised by the condensed formula H2C=O.[17] The molecule is planar, Y-shaped and its molecular symmetry belongs to the C2v point group.[18] The precise molecular geometry of gaseous formaldehyde has been determined by gas electron diffraction[17][19] and microwave spectroscopy.[20][21] The bond lengths are 1.21 Å for the carbon–oxygen bond[17][19][20][21][22] and around 1.11 Å for the carbon–hydrogen bond,[17][19][20][21] while the H–C–H bond angle is 117°,[20][21] close to the 120° angle found in an ideal trigonal planar molecule.[17] Some excited electronic states of formaldehyde are pyramidal rather than planar as in the ground state.[22]

Occurrence

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 of smog. Formaldehyde has also been detected in outer space.

Formaldehyde and its adducts are ubiquitous in nature. Food may contain formaldehyde at levels 1–100 mg/kg.[23] Formaldehyde, formed in the metabolism of the amino acids serine and threonine, is found in the bloodstream of humans and other primates at concentrations of approximately 50 micromolar.[24] 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.[25]

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, converting it to formic acid, so it does not accumulate.[26][27] It nonetheless presents significant health concerns, as a contaminant.

Interstellar formaldehyde

Main page: Astronomy:Interstellar formaldehyde

Formaldehyde appears to be a useful probe in astrochemistry due to prominence of the 110←111 and 211←212 K-doublet transitions. It was the first polyatomic organic molecule detected in the interstellar medium.[28] 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 been extensively studied, yielding new extragalactic sources.[29] A proposed mechanism for the formation is the hydrogenation of CO ice:[30]

H + CO → HCO
HCO + H → CH2O

HCN, HNC, H2CO, and dust have also been observed inside the comae of comets C/2012 F6 (Lemmon) and C/2012 S1 (ISON).[31][32]

Synthesis and industrial production

Laboratory synthesis

Formaldehyde was first reported in 1859 by the Russian chemist Aleksandr Butlerov (1828–1886).[33] In his paper, Butlerov referred to formaldehyde as "dioxymethylen" (methylene dioxide) [page 247] because his empirical formula for it was incorrect (C4H4O4). It was conclusively identified by August Wilhelm von Hofmann, who first announced the production of formaldehyde by passing methanol vapor in air over hot platinum wire.[34][35] With modifications, Hoffmann's method remains the basis of the present day industrial route.

Solution routes to formaldehyde also entail oxidation of methanol or methyl iodide.[36]

Industry

Formaldehyde is produced industrially by the catalytic oxidation of methanol. The most common catalysts are silver metal, iron(III) oxide,[37] iron molybdenum oxides [e.g. iron(III) molybdate] with a molybdenum-enriched surface,[38] or vanadium oxides. In the commonly used formox process, methanol and oxygen react at c. 250–400 °C in presence of iron oxide in combination with molybdenum and/or vanadium to produce formaldehyde according to the chemical equation:[39]

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 reaction:

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.[39]

Biochemistry

Formaldehyde is produced via several enzyme-catalyzed routes.[40] Living beings, including humans, produce formaldehyde as part of their metabolism. Formaldehyde are key to several bodily functions (e.g. epigenetics[24]), but its amount must also be tightly controlled to avoid self-poisioning.[41]

  • Serine hydroxymethyltransferase can decompose serine into formaldehyde and glycine, according to this reaction: HOCH2CH(NH2)CO2H → CH2O + H2C(NH2)CO2H.
  • methylotrophic microbes convert methanol into formaldehyde and energy via methanol dehydrogenase: CH3OH → CH2O + 2e + 2H+
  • Other routes to formaldehyde include oxidative demethylations, semicarbazide-sensitive amine oxidases, dimethylglycine dehydrogenases, lipid peroxidases, P450 oxidases, and N-methyl group demethylases.[40]

Formaldehyde is catabolized by alcohol dehydrogenase ADH5 and aldehyde dehydrogenase ALDH2.[42]

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.

Polymerization and hydration

Gaseous formaldehyde polymerizes on the active sites of the vessel walls, but the mechanism of the reaction is unknown.[43] Small amounts of hydrogen chloride (or boron trifluoride, or stannic chloride) present in gaseous formaldehyde provide the catalytic effect and make the polymerization rapid.[44] Monomeric CH2O is a gas and is rarely encountered in the laboratory.

Formaldehyde in aqueous solutions, unlike some other small aldehydes (which need specific conditions to oligomerize through aldol condensation) oligomerizes spontaneously at a common state. The trimer is 1,3,5-trioxane ((CH
2
O)
3
) is typical oligomer. Many cyclic oligomers of other sizes have been isolated. Similarly, formaldehyde hydrates to give the geminal diol methanediol, which condenses further to form hydroxy-terminated oligomers HO(CH2O)nH. The polymer is called paraformaldehyde. The higher concentration of formaldehyde—the more equilibrium shifts towards polymerization. Diluting with water or increasing the solution temperature, as well as adding alcohols (such as methanol or ethanol) lowers that tendency.

Oxidation and reduction

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

In the Cannizzaro reaction, formaldehyde and base react to produce formic acid and methanol, a disproportionation reaction.

Hydroxymethylation and chloromethylation

Formaldehyde reacts with many compounds, resulting in hydroxymethylation:

X-H + CH2O → X-CH2OH

(X = R2N, 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:[45]

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.[46] Phenol results in polymers.

Other reactions

Many amino acids react with formaldehyde.[40] Cysteine converts to thioproline.

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.[39] The textile industry uses formaldehyde-based resins as finishers to make fabrics crease-resistant.[47]

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 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.

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 RDX.

Error creating thumbnail: Unable to save thumbnail to destination

Condensation with acetaldehyde affords pentaerythritol, a chemical necessary in synthesizing PETN, a high explosive.[48] 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.[49] 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.[50]

Aquarists use formaldehyde as a treatment for the parasites Ichthyophthirius multifiliis and Cryptocaryon irritans.[51] Formaldehyde is one of the main disinfectants recommended for destroying anthrax.[52]

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.[53]

Formaldehyde is commonly used to disinfect (via fumigating, sprinklers, and spray sleds) poultry and swine confinement buildings, egg hatcheries, rooms, railway cars, mushroom houses, tools, and equipment. Formaldehyde is a valuable packaged preservative in the food and beverage industry.[54][better source needed]

Tissue fixative and embalming agent

Injecting a giant squid specimen with formalin for preservation

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.[55][56] Countries with a strong tradition of embalming corpses, such as Ireland and other colder-weather countries, have raised concerns. Despite reports to the contrary,[57] 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).[58]

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 RNA gel electrophoresis, preventing RNA from forming secondary 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,[59] 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.[60][61] In 2011, the US National Toxicology Program described formaldehyde as "known to be a human carcinogen".[62][63][64]

Chronic inhalation

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.[65] At concentrations above 0.1 ppm in air, formaldehyde can irritate the eyes and mucous membranes.[66] Formaldehyde inhaled at this concentration may cause headaches, a burning sensation in the throat, and difficulty breathing, and can trigger or aggravate asthma symptoms.[67][68]

The CDC considers formaldehyde as a systemic poison. Formaldehyde poisoning can cause permanent changes in the nervous system's functions.[69]

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.[70] A 2009 review of studies has shown a strong association between exposure to formaldehyde and the development of childhood asthma.[71]

A theory was proposed for the carcinogenesis of formaldehyde in 1978.[72] 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[73] associated with nasal sinus cancer and nasopharyngeal cancer.[74] Studies in 2009 and 2010 have also shown a positive correlation between exposure to formaldehyde and the development of leukemia, particularly myeloid leukemia.[75][76] Nasopharyngeal and sinonasal cancers are relatively rare, with a combined annual incidence in the United States of < 4,000 cases.[77][78] About 30,000 cases of myeloid leukemia occur in the United States each year.[79][80] Some evidence suggests that workplace exposure to formaldehyde contributes to sinonasal cancers.[81] 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.[82] Other factors are important in determining individual risk for the development of leukemia or nasopharyngeal cancer.[81][83][84] In yeast, formaldehyde is found to perturb pathways for DNA repair and cell cycle.[85]

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.[86] In July 2016, the U.S. EPA released a prepublication version of its final rule on Formaldehyde Emission Standards for Composite Wood Products.[87] 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.[88]


The U.S. EPA allows no more than 0.016 ppm formaldehyde in the air in new buildings constructed for that agency.[89][failed verification] 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.[90] The Federal Emergency Management Agency (FEMA) has also announced limits on the formaldehyde levels in trailers purchased by that agency.[91] 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.[74]

The eyes are most sensitive to formaldehyde exposure: The lowest level at which many people can begin to smell formaldehyde ranges between 0.05 and 1 ppm. The maximum concentration value at the workplace is 0.3 ppm.[92][need quotation to verify] 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.[93]

Some air purifiers include filtering technology that is supposed to lower indoor formaldehyde concentration.

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 conditions. 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.

In operating rooms, formaldehyde is produced as a byproduct of electrosurgery and is present in surgical smoke, exposing surgeons and healthcare workers to potentially unsafe concentrations.[94]

Formaldehyde levels in air can be sampled and tested in several ways, including impinger, treated sorbent, and passive monitors.[95] The National Institute for Occupational Safety and Health (NIOSH) has measurement methods numbered 2016, 2541, 3500, and 3800.[96]

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."[62][63][64] 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.[97]

Acute irritation and allergic reaction

Patch test

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%).[98] People with formaldehyde allergy are advised to avoid formaldehyde releasers as well (e.g., Quaternium-15, imidazolidinyl urea, and diazolidinyl urea).[99] 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).[50] Formaldehyde has been banned in cosmetics in both Sweden[citation needed] and Japan .[100]

Other routes

Formaldehyde occurs naturally, and is "an essential intermediate in cellular metabolism in mammals and humans."[39] According to the American Chemistry Council, "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."[101]

The twelfth edition of NTP Report on Carcinogens notes that "food and water contain measureable concentrations of formaldehyde, but the significance of ingestion as a source of formaldehyde exposure for the general population is questionable." Food formaldehyde generally occurs in a bound form and formaldehyde is unstable in an aqueous solution.[64]

In humans, ingestion of as little as 30 millilitres (1.0 US fl oz) of 37% formaldehyde solution can cause death. Other symptoms associated with ingesting such a solution include gastrointestinal damage (vomiting, abdominal pain), and systematic damage (dizziness).[69] 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 high-performance liquid chromatography is the most sensitive.[102]

Regulation

Several web articles[Like whom?] 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.[103][104] 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.[50]

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.[105] 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."[106]

Formaldehyde was declared a toxic substance by the 1999 Canadian Environmental Protection Act.[107]

The FDA is proposing a ban on hair relaxers with formaldehyde due to cancer concerns.[108]

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.[109] In August 2011, at least at two Carrefour supermarkets, the Central Jakarta Livestock and Fishery Sub-Department found cendol containing 10 parts per million of formaldehyde.[110] In 2014, the owner of two noodle factories in Bogor, Indonesia, was arrested for using formaldehyde in noodles. 50 kg of formaldehyde was confiscated.[111] Foods known to be contaminated included noodles, salted fish, and tofu. Chicken and beer were also rumored to be contaminated. In some places, such as China, manufacturers still use formaldehyde illegally as a preservative in foods, which exposes people to formaldehyde ingestion.[112] 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 and concern[113] regarding formaldehyde's toxicity.[114][115]

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.[116] In 2012, 1 billion rupiah (almost US$100,000) of fish imported from Pakistan to Batam, Indonesia, were found laced with formaldehyde.[117]

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.[118] 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.[119]

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

References

  1. 1.0 1.1 "Front Matter". 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. ISBN 978-0-85404-182-4. 
  2. 2.0 2.1 "SIDS Initial Assessment Report". International Programme on Chemical Safety. http://www.inchem.org/documents/sids/sids/FORMALDEHYDE.pdf. 
  3. Spence, Robert; Wild, William (1935). "114. The vapour-pressure curve of formaldehyde, and some related data". Journal of the Chemical Society (Resumed): 506–509. doi:10.1039/jr9350000506. 
  4. "PubChem Compound Database; CID=712". National Center for Biotechnology Information. https://pubchem.ncbi.nlm.nih.gov/compound/formaldehyde#section=Odor-Threshold. 
  5. "Acidity of aldehydes". Chemistry Stack Exchange. http://chemistry.stackexchange.com/questions/12232/acidity-of-aldehydes. 
  6. Nelson, R. D. Jr.; Lide, D. R.; Maryott, A. A. (1967). "Selected Values of electric dipole moments for molecules in the gas phase (NSRDS-NBS10)". https://nvlpubs.nist.gov/nistpubs/Legacy/NSRDS/nbsnsrds10.pdf. 
  7. Weast, Robert C., ed (1981). CRC Handbook of Chemistry and Physics (62nd ed.). Boca Raton, FL: CRC Press. pp. C–301, E–61. ISBN 0-8493-0462-8. 
  8. CRC handbook of chemistry and physics: a ready-reference book of chemical and physical data.. William M. Haynes, David R. Lide, Thomas J. Bruno (2016-2017, 97th ed.). Boca Raton, Florida. 2016. ISBN 978-1-4987-5428-6. OCLC 930681942. https://www.worldcat.org/oclc/930681942. 
  9. 9.0 9.1 9.2 Record of Formaldehyde in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 13 March 2020.
  10. 10.0 10.1 10.2 NIOSH Pocket Guide to Chemical Hazards. "#0293". National Institute for Occupational Safety and Health (NIOSH). https://www.cdc.gov/niosh/npg/npgd0293.html. 
  11. NIOSH Pocket Guide to Chemical Hazards. "#0294". National Institute for Occupational Safety and Health (NIOSH). https://www.cdc.gov/niosh/npg/npgd0294.html. 
  12. "Substance Name: Formaldehyde [USP"]. US National Library of Medicine. https://chem.nlm.nih.gov/chemidplus/rn/50-00-0. 
  13. 13.0 13.1 "Formaldehyde". Immediately Dangerous to Life and Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH). https://www.cdc.gov/niosh/idlh/50000.html. 
  14. Humans, IARC Working Group on the Evaluation of Carcinogenic Risks to (2006) (in en). Summary of Data Reported and Evaluation. International Agency for Research on Cancer. https://www.ncbi.nlm.nih.gov/books/NBK326456/. 
  15. 15.0 15.1 "Formaldehyde and Cancer Risk". 10 June 2011. https://www.cancer.gov/about-cancer/causes-prevention/risk/substances/formaldehyde/formaldehyde-fact-sheet. 
  16. Formalin, Merriam-Webster, Inc., 15 January 2020, https://www.merriam-webster.com/dictionary/formalin, retrieved 18 February 2020 
  17. 17.0 17.1 17.2 17.3 17.4 Wells, A. F. (1984). Structural Inorganic Chemistry (5th ed.). Oxford University Press. pp. 915–917, 926. ISBN 978-0-19-965763-6. 
  18. Greenwood, Norman N.; Earnshaw, Alan (1997). Chemistry of the Elements (2nd ed.). Butterworth-Heinemann. p. 1291. ISBN 978-0-08-037941-8. 
  19. 19.0 19.1 19.2 Chuichi, Kato; Shigehiro, Konaka; Takao, Iijima; Masao, Kimura (1969). "Electron Diffraction Studies of Formaldehyde, Acetaldehyde and Acetone". Bull. Chem. Soc. Jpn. 42 (8): 2148–2158. doi:10.1246/bcsj.42.2148. 
  20. 20.0 20.1 20.2 20.3 William M. Haynes, ed (2012). CRC Handbook of Chemistry and Physics (93rd ed.). CRC Press. pp. 9–39. ISBN 978-1439880500. 
  21. 21.0 21.1 21.2 21.3 Duncan, J. L. (1974). "The ground-state average and equilibrium structures of formaldehyde and ethylene". Mol. Phys. 28 (5): 1177–1191. doi:10.1080/00268977400102501. Bibcode1974MolPh..28.1177D. 
  22. 22.0 22.1 Smith, Michael B.; March, Jerry (2007). March's Advanced Organic Chemistry (6th ed.). John Wiley & Sons. pp. 24–25, 335. ISBN 978-0-471-72091-1. 
  23. "Chapter 5.8 Formaldehyde" (in en). Air Quality Guidelines (2nd ed.). Copenhagen, Denmark: WHO Regional Office for Europe. 2001. https://intranet.euro.who.int/__data/assets/pdf_file/0014/123062/AQG2ndEd_5_8Formaldehyde.pdf. 
  24. 24.0 24.1 Pham, Vanha N.; Bruemmer, Kevin J.; Toh, Joel D. W.; Ge, Eva J.; Tenney, Logan; Ward, Carl C.; Dingler, Felix A.; Millington, Christopher L. et al. (2023). "Formaldehyde regulates S -adenosylmethionine biosynthesis and one-carbon metabolism". Science 382 (6670): eabp9201. doi:10.1126/science.abp9201. PMID 37917677. 
  25. Swenberg, J. A.; Lu, K.; Moeller, B. C.; Gao, L.; Upton, P. B.; Nakamura, J.; Starr, T. B. (2011). "Endogenous versus Exogenous DNA Adducts: Their Role in Carcinogenesis, Epidemiology, and Risk Assessment". Toxicological Sciences 120 (Suppl 1): S130–S145. doi:10.1093/toxsci/kfq371. PMID 21163908. 
  26. "Formaldehyde Is Biodegradable, Quickly Broken Down in the Air By Sunlight or By Bacteria in Soil or Water" (Press release). Formaldehyde Panel of the American Chemistry Council. 2014-01-29. Archived from the original on 2019-03-28. Retrieved 2017-04-22.
  27. "Error: no |title= specified when using {{Cite web}}". 2019-03-28. https://www.atsdr.cdc.gov/ToxProfiles/tp111.pdf. 
  28. Zuckerman, B.; Buhl, D.; Palmer, P.; Snyder, L. E. (1970). "Observation of interstellar formaldehyde". Astrophys. J. 160: 485–506. doi:10.1086/150449. Bibcode1970ApJ...160..485Z. 
  29. Mangum, Jeffrey G.; Darling, Jeremy; Menten, Karl M.; Henkel, Christian (2008). "Formaldehyde Densitometry of Starburst Galaxies". Astrophys. J. 673 (2): 832–46. doi:10.1086/524354. Bibcode2008ApJ...673..832M. 
  30. 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 (1): 541–48. doi:10.1086/339279. Bibcode2002ApJ...569..541W. 
  31. Zubritsky, Elizabeth; Neal-Jones, Nancy (11 August 2014). "RELEASE 14-038 - NASA's 3-D Study of Comets Reveals Chemical Factory at Work". NASA. http://www.nasa.gov/press/2014/august/goddard/nasa-s-3-d-study-of-comets-reveals-chemical-factory-at-work. 
  32. Cordiner, M.A. (11 August 2014). "Mapping the Release of Volatiles in the Inner Comae of Comets C/2012 F6 (Lemmon) and C/2012 S1 (ISON) Using the Atacama Large Millimeter/Submillimeter Array". The Astrophysical Journal 792 (1): L2. doi:10.1088/2041-8205/792/1/L2. Bibcode2014ApJ...792L...2C. 
  33. Butlerow, A (1859). Ueber einige Derivate des Jodmethylens. 111. pp. 242–252. https://books.google.com/books?id=NYs8AAAAIAAJ&pg=PA242. 
  34. 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: 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:
  35. Read, J. (1935). Text-Book of Organic Chemistry. London: G Bell & Sons. 
  36. Hooker, Jacob M.; Schönberger, Matthias; Schieferstein, Hanno; Fowler, Joanna S. (2008). "A Simple, Rapid Method for the Preparation of [11C]Formaldehyde". Angewandte Chemie International Edition 47 (32): 5989–5992. doi:10.1002/anie.200800991. PMID 18604787. 
  37. Wang, Chien-Tsung; Ro, Shih-Hung (2005-05-10). "Nanocluster iron oxide-silica aerogel catalysts for methanol partial oxidation" (in en). Applied Catalysis A: General 285 (1): 196–204. doi:10.1016/j.apcata.2005.02.029. ISSN 0926-860X. https://www.sciencedirect.com/science/article/pii/S0926860X05001523. 
  38. Dias, Ana Paula Soares; Montemor, Fátima; Portela, Manuel Farinha; Kiennemann, Alain (2015-02-01). "The role of the suprastoichiometric molybdenum during methanol to formaldehyde oxidation over Mo–Fe mixed oxides" (in en). Journal of Molecular Catalysis A: Chemical 397: 93–98. doi:10.1016/j.molcata.2014.10.022. ISSN 1381-1169. https://www.sciencedirect.com/science/article/pii/S1381116914004774. 
  39. 39.0 39.1 39.2 39.3 Reuss, Günther; Disteldorf, Walter; Gamer, Armin Otto; Hilt, Albrecht (2000). "Ullmann's Encyclopedia of Industrial Chemistry". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a11_619. 
  40. 40.0 40.1 40.2 Kamps, Jos J. A. G.; Hopkinson, Richard J.; Schofield, Christopher J.; Claridge, Timothy D. W. (2019). "How formaldehyde reacts with amino acids". Communications Chemistry 2. doi:10.1038/s42004-019-0224-2. 
  41. Chen, J; Chen, W; Zhang, J; Zhao, H; Cui, J; Wu, J; Shi, A (27 September 2023). "Dual effects of endogenous formaldehyde on the organism and drugs for its removal.". Journal of Applied Toxicology. doi:10.1002/jat.4546. PMID 37766419. 
  42. Nakamura, Jun; Holley, Darcy W.; Kawamoto, Toshihiro; Bultman, Scott J. (December 2020). "The failure of two major formaldehyde catabolism enzymes (ADH5 and ALDH2) leads to partial synthetic lethality in C57BL/6 mice". Genes and Environment 42 (1): 21. doi:10.1186/s41021-020-00160-4. PMID 32514323. Bibcode2020GeneE..42...21N. 
  43. Boyles, James G.; Toby, Sidney (June 1966). "The mechanism of the polymerization of gaseous formaldehyde". Journal of Polymer Science Part B: Polymer Letters 4 (6): 411–415. doi:10.1002/pol.1966.110040608. Bibcode1966JPoSL...4..411B. https://onlinelibrary.wiley.com/doi/10.1002/pol.1966.110040608. 
  44. Bevington, J. C.; Norrish, R. G. W. (1951-03-07). "The catalyzed polymerization of gaseous formaldehyde" (in en). Proceedings of the Royal Society of London. Series A. Mathematical and Physical Sciences 205 (1083): 516–529. doi:10.1098/rspa.1951.0046. ISSN 0080-4630. Bibcode1951RSPSA.205..516B. https://royalsocietypublishing.org/doi/10.1098/rspa.1951.0046. 
  45. Bost, R. W.; Constable, E. W. (1936). "sym-Trithiane". Organic Syntheses 16: 81. http://www.orgsyn.org/demo.aspx?prep=cv2p0610. ; Collective Volume, 2, pp. 610 
  46. Gutsche, C. D.; Iqbal, M. (1993). "p-tert-Butylcalix[4]arene". Organic Syntheses. http://www.orgsyn.org/demo.aspx?prep=cv8p0075. ; Collective Volume, 8, pp. 75 
  47. "Formaldehyde in Clothing and Textiles FactSheet". Australian National Industrial Chemicals Notification and Assessment Scheme. 2013-05-01. https://www.nicnas.gov.au/chemical-information/factsheets/chemical-name/formaldehyde-in-clothing-and-textiles. 
  48. Schurink, H. B. J. (1925). "Pentaerythritol". Organic Syntheses 4: 53. http://www.orgsyn.org/demo.aspx?prep=cv1p0425. ; Collective Volume, 1, pp. 425 
  49. "Ingredients of Vaccines - Fact Sheet". Center for Disease Control. https://www.cdc.gov/vaccines/vac-gen/additives.htm. "Formaldehyde is used to inactivate bacterial products for toxoid vaccines, (these are 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. Most formaldehyde is removed from the vaccine before it is packaged." 
  50. 50.0 50.1 50.2 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. PMID 19706047. https://www.rug.nl/research/portal/en/publications/formaldehydereleasers(c3ff7adf-9f21-4564-96e0-0b9c5d025b30).html. 
  51. Francis-Floyd, Ruth (April 1996). "Use of Formalin to Control Fish Parasites". Institute of Food and Agricultural Sciences, University of Florida. http://edis.ifas.ufl.edu/vm061. 
  52. "Disinfection, decontamination, fumigation, incineration" (in en), Anthrax in Humans and Animals. 4th edition (World Health Organization), 2008, https://www.ncbi.nlm.nih.gov/books/NBK310477/, retrieved 2023-11-20 
  53. "§573.460 Formaldehyde". U.S. Government Publishing Office. 2019-04-19. http://www.ecfr.gov/cgi-bin/text-idx?SID=373e2ce8edf3f674e80eb9270a461c7d&mc=true&node=se21.6.573_1460&rgn=div8. 
  54. "Registered Formaldehyde". November 17, 2023. https://brainerdchemical.com/product/formaldehyde-37-registered/. 
  55. 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))
  56. Commission 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))
  57. Patel, Alkesh (2007-07-04). "Formaldehyde Ban set for 22 September 2007". WebWire. http://www.webwire.com/ViewPressRel.asp?aId=41468. 
  58. "European chemical Substances Information System (ESIS) entry for formaldehyde". http://esis.jrc.ec.europa.eu/. 
  59. "Process C-41 Using Kodak Flexicolor Chemicals - Publication Z-131". Kodak. http://www.kodak.com/global/en/service/Zmanuals/z131.shtml. 
  60. "Formaldehyde", Formaldehyde, 2-Butoxyethanol and 1-tert-Butoxypropan-2-ol, IARC Monographs on the Evaluation of Carcinogenic Risks to Humans 88, Lyon, France: International Agency for Research on Cancer, 2006, pp. 39–325, ISBN 978-92-832-1288-1, http://monographs.iarc.fr/ENG/Monographs/vol88/mono88-6.pdf 
  61. "Formaldehyde (gas)", Report on Carcinogens, Eleventh Edition (PDF), U.S. Department of Health and Human Services, Public Health Service, National Toxicology Program, 2005
  62. 62.0 62.1 Harris, Gardiner (2011-06-10). "Government Says 2 Common Materials Pose Risk of Cancer". The New York Times. https://www.nytimes.com/2011/06/11/health/11cancer.html. 
  63. 63.0 63.1 National Toxicology Program (2011-06-10). "12th Report on Carcinogens". National Toxicology Program. http://ntp.niehs.nih.gov/go/roc12. 
  64. 64.0 64.1 64.2 National Toxicology Program (2011-06-10). "Report On Carcinogens - Twelfth Edition - 2011". National Toxicology Program. https://ntp.niehs.nih.gov/go/roc12. 
  65. "Indoor Air Pollution in California". Air Resources Board, California Environmental Protection Agency. July 2005. pp. 65–70. http://www.arb.ca.gov/research/indoor/ab1173/rpt0705.pdf. 
  66. "Formaldehyde". Occupational Safety and Health Administration. August 2008. https://www.osha.gov/SLTC/formaldehyde/index.html. 
  67. "Formaldehyde Reference Exposure Levels" (PDF). California Office Of Health Hazard Assessment. December 2008. http://www.oehha.ca.gov/air/hot_spots/2008/AppendixD1_final.pdf#page=128. 
  68. "Formaldehyde and Indoor Air". Health Canada. 2012-03-29. https://www.canada.ca/en/health-canada/services/environmental-workplace-health/reports-publications/air-quality/formaldehyde-indoor-air-environment-workplace-health.html. 
  69. 69.0 69.1 "Formaldehyde | Medical Management Guidelines | Toxic Substance Portal | ATSDR". Centres for Disease Control and Prevention. https://wwwn.cdc.gov/TSP/MMG/MMGDetails.aspx?mmgid=216&toxid=39. 
  70. 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. PMID 1821362. 
  71. McGwin, G; Lienert, J; Kennedy, JI (November 2009). "Formaldehyde Exposure and Asthma in Children: A Systematic Review". Environmental Health Perspectives 118 (3): 313–7. doi:10.1289/ehp.0901143. PMID 20064771. 
  72. Lobachev, AN (1978). "РОЛЬ МИТОХОНДРИАЛЬНЫХ ПРОЦЕССОВ В РАЗВИТИИ И СТАРЕНИИ ОРГАНИЗМА. СТАРЕНИЕ И РАК" (in ru). VINITI. http://aiexandr2010.narod.ru/rol.pdf. 
  73. IARC Working Group on the Evaluation of Carcinogenic Risks to Humans (2006). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans - VOLUME 88 - Formaldehyde, 2-Butoxyethanol and 1-tert-Butoxypropan-2-ol. WHO Press. ISBN 92-832-1288-6. https://monographs.iarc.fr/wp-content/uploads/2018/06/mono88.pdf. Retrieved 2019-04-23. 
  74. 74.0 74.1 "Formaldehyde and Cancer Risk". National Cancer Institute. 2011-06-10. http://www.cancer.gov/cancertopics/factsheet/Risk/formaldehyde. 
  75. Zhang, Luoping; Steinmaus, Craig; Eastmond, Eastmond; Xin, Xin; Smith, Smith (March–June 2009). "Formaldehyde exposure and leukemia: A new meta-analysis and potential mechanisms". Mutation Research/Reviews in Mutation Research 681 (2–3): 150–168. doi:10.1016/j.mrrev.2008.07.002. PMID 18674636. http://ehs.sph.berkeley.edu/krsmith/CRA/cancer/ZhangL_2008.pdf. Retrieved 2013-05-22. 
  76. Zhang, Luoping; Freeman, Laura E. Beane; Nakamura, Jun; Hecht, Stephen S.; Vandenberg, John J.; Smith, Martyn T.; Sonawane, Babasaheb R. (2010). "Formaldehyde and Leukemia: Epidemiology, Potential Mechanisms, and Implications for Risk Assessment". Environmental and Molecular Mutagenesis 51 (3): 181–191. doi:10.1002/em.20534. PMID 19790261. Bibcode2010EnvMM..51..181Z. 
  77. "Key Statistics for Nasopharyngeal Cancer". American Cancer Society. https://www.cancer.org/cancer/nasopharyngeal-cancer/about/key-statistics.html. 
  78. "Incidence and survival in patients with sinonasal cancer: a historical analysis of population-based data". Head Neck 34 (6): 877–85. June 2012. doi:10.1002/hed.21830. PMID 22127982. 
  79. "Key Statistics for Chronic Myeloid Leukemia". American Cancer Society. https://www.cancer.org/cancer/chronic-myeloid-leukemia/about/statistics.html. 
  80. "What are the key statistics about acute myeloid leukemia?Key Statistics for Acute Myeloid Leukemia (AML)". American Cancer Society. https://www.cancer.org/cancer/acute-myeloid-leukemia/about/key-statistics.html. 
  81. 81.0 81.1 "Risk Factors for Nasopharyngeal Cancer". 24 September 2018. http://www.cancer.org/cancer/nasopharyngealcancer/detailedguide/nasopharyngeal-cancer-risk-factors. 
  82. Butticè, Claudio (2015). "Solvents". in Colditz, Graham A.. The SAGE Encyclopedia of Cancer and Society (Second ed.). Thousand Oaks: SAGE Publications. pp. 1089–1091. doi:10.4135/9781483345758.n530. ISBN 9781483345734. https://www.academia.edu/16541375. 
  83. "Risk Factors for Acute Myeloid Leukemia (AML)". American Cancer Society. 2018-08-21. https://www.cancer.org/cancer/acute-myeloid-leukemia/causes-risks-prevention/risk-factors.html. 
  84. "Risk Factors for Chronic Myeloid Leukemia". American Cancer Society. 2018-06-19. https://www.cancer.org/cancer/chronic-myeloid-leukemia/causes-risks-prevention/risk-factors.html. 
  85. Ogbede, J. U., Giaever, G., & Nislow, C. (2021). A genome-wide portrait of pervasive drug contaminants. Scientific reports, 11(1), 12487. https://doi.org/10.1038/s41598-021-91792-1
  86. Dales, R; Liu, L; Wheeler, AJ; Gilbert, NL (July 2008). "Quality of indoor residential air and health". Canadian Medical Association Journal 179 (2): 147–52. doi:10.1503/cmaj.070359. PMID 18625986. 
  87. "Formaldehyde Emission Standards for Composite Wood Products". EPA. 8 July 2016. https://www.epa.gov/formaldehyde/formaldehyde-emission-standards-composite-wood-products-0. 
  88. Passmore, Whitney; Sullivan, Michael J. (2016-08-04). "EPA Issues Final Rule on Formaldehyde Emission Standards for Composite Wood Products". The National Law Review (Womble Carlyle Sandridge & Rice, PLLC). http://www.natlawreview.com/article/epa-issues-final-rule-formaldehyde-emission-standards-composite-wood-products. 
  89. "Testing for Indoor Air Quality, Baseline IAQ, and Materials". Environmental Protection Agency. http://www.epa.gov/rtp/new-bldg/environmental/s_01445.htm. 
  90. M. Koontz, H. Rector, D. Cade, C. Wilkes, and L. Niang. 1996. Residential Indoor Air Formaldehyde Testing Program: Pilot Study. Report No. IE-2814, prepared by GEOMET Technologies, Inc. for the USEPA Office of Pollution Prevention and Toxics under EPA Contract No. 68-D3-0013, Washington, DC
  91. Evans, Ben (2008-04-11). "FEMA limits formaldehyde in trailers". The Boston Globe. http://www.boston.com/news/nation/washington/articles/2008/04/11/fema_limits_formaldehyde_in_trailers/. 
  92. "Formaldehyde CAS 50-00-0". United Nations Environment Programme. http://www.inchem.org/documents/sids/sids/FORMALDEHYDE.pdf. 
  93. Formaldehyde Epidemiology, Toxicology and Environmental Group, Inc (August 2002). "Formaldehyde and Facts About Health Effects". http://www2.dupont.com/Plastics/en_US/assets/downloads/processing/FETEG_Facts.pdf. 
  94. Carroll, Gregory T.; Kirschman, David L. (2023). "Catalytic Surgical Smoke Filtration Unit Reduces Formaldehyde Levels in a Simulated Operating Room Environment" (in en). ACS Chemical Health & Safety 30 (1): 21–28. doi:10.1021/acs.chas.2c00071. ISSN 1871-5532. https://pubs.acs.org/doi/10.1021/acs.chas.2c00071. 
  95. "When Sampling Formaldehyde, The Medium Matters". Galson Labs. http://www.galsonlabs.com/services/referenceinfo/technical_bulletins.php?tb_id=18. 
  96. "NIOSH Pocket Gide to Chemical Hazards: Formaldehyde". National Institute for Occupational Safety and Health, CDC. 2018-11-29. https://www.cdc.gov/niosh/npg/npgd0293.html. 
  97. Addendum to the 12th Report on Carcinogens (PDF) National Toxicology Program, U.S. Department of Health and Human Services. Retrieved 06-13-2011
  98. "Patch-test results of the North American Contact Dermatitis Group 2005-2006". Dermatitis 20 (3): 149–60. 2009. doi:10.2310/6620.2009.08097. PMID 19470301. 
  99. "Formaldehyde allergy". New Zealand Dermatological Society. 2002. https://www.dermnetnz.org/topics/formaldehyde-allergy/. 
  100. Hayashida, Mike. "The Regulation of Cosmetics in Japan". http://www.yakujihou.com/img/CosRegulationJapan.pdf. 
  101. "Formaldehyde occurs naturally and is all around us". https://www.americanchemistry.com/content/download/5865/file/Formaldehyde-Occurs-Naturally-and-Is-All-Around-Us.pdf. 
  102. Ngwa, Moise (2010-10-25). "formaldehyde testing". Cedar Rapids Gazette. http://monographs.iarc.fr/ENG/Monographs/vol88/mono88-6A.pdf. 
  103. "European Union Bans formaldehyde/formalin within Europe". European Commission's Environment Directorate-General. 2007-06-22. pp. 1–3. http://ec.europa.eu/environment/biocides/pdf/070622_withdrawal_notice.pdf. 
  104. "ESIS (European Chemical Substances Information System)". European Commission Joint Research Centre Institute for Health and Consumer Protection. February 2009. http://esis.jrc.ec.europa.eu/. 
  105. "S.1660 - Formaldehyde Standards for Composite Wood Products Act". GovTrack. 2010-08-25. https://www.govtrack.us/congress/bills/111/s1660/text. 
  106. "Formaldehyde Emission Standards for Composite Wood Products". United States Federal Register. 12 December 2016. https://www.regulations.gov/document?D=EPA-HQ-OPPT-2016-0461-0001. "The emission standards will be 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." 
  107. "Health Canada - Proposed residential indoor air quality guidelines for formaldehyde". Health Canada. April 2007. http://www.hc-sc.gc.ca/ewh-semt/pubs/air/formaldehyde/preamble-eng.php. 
  108. "View Rule". https://www.reginfo.gov/public/do/eAgendaViewRule?pubId=202304&RIN=0910-AI83. 
  109. "Formaldehyde-laced foods reemerge in Indonesian markets". antaranews.com. 2011-08-10. http://www.antaranews.com/en/news/74626/formaldehyde-laced-foods-reemerge-in-indonesian-markets. 
  110. "Formaldehyde-Tainted Rice Drinks Found at Carrefour Markets". Jakarta Globe. 2011-08-22. http://www.thejakartaglobe.com/health/formaldehyde-tainted-rice-drinks-found-at-carrefour-markets/460829. 
  111. "BPOM Uncovers Two Formaldehyde-Tainted Noodle Factories in Bogor". Jakarta Globe. 2014-10-12. http://thejakartaglobe.beritasatu.com/news/bpom-uncovers-two-formaldehyde-tainted-noodle-factories-bogor/. 
  112. Blum, Deborah, 1954- (2018-09-25). The poison squad: one chemist's single-minded crusade for food safety at the turn of the twentieth century. Go Big Read (Program). New York, New York. ISBN 9781594205149. OCLC 1024107182. 
  113. "Was Death in the Milk?". The Indianapolis News: p. 5. 1900-07-31. https://www.newspapers.com/clip/888392/formaldehyde_in_milk/.  open access
  114. "Wants New Law Enacted. Food Inspector Farnsworth Would Have Use of Formaldehyde in Milk Stopped". The Topeka Daily Capital: p. 8. 1903-08-30. https://www.newspapers.com/clip/888394/formaldehyde_in_milk/.  open access
  115. "Illegal business 'being run by a gang'". The Nation. 2011-06-16. http://www.nationmultimedia.com/2011/06/16/national/Illegal-business-being-run-by-a-gang-30157928.html. 
  116. "Import of formaldehyde fish from Pakistan foiled in Batam". The Jakarta Post. 2012-02-23. http://www.thejakartapost.com/news/2012/02/23/import-formaldehyde-fish-pakistan-foiled-batam.html. 
  117. "Trader Fined for Selling Fish Treated with Formalin". The Daily Star. 2009-08-31. https://www.thedailystar.net/news-detail-103948. 
  118. "Formalin Control Bill 2015 passed". ntv online. 2015-02-16. http://en.ntvbd.com/bangladesh/923/Formalin-Control-Bill-2015-passed. 

Notes

  1. Formaldehyde is classified as a carcinogen, according to the Environmental Protection Agency, International Agency for Research on Cancer (IARC), and U.S. National Toxicology Program.[15]

External links