Formaldehyde
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Names | |||
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Preferred IUPAC name
Formaldehyde[1] | |||
Systematic IUPAC name
Methanal[1] | |||
Other names
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Identifiers | |||
3D model (
JSmol ) |
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3DMet | |||
1209228 | |||
ChEBI | |||
ChEMBL | |||
ChemSpider | |||
DrugBank | |||
ECHA InfoCard
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100.000.002 | ||
EC Number |
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E number | E240 (preservatives) | ||
445 | |||
IUPHAR/BPS |
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KEGG | |||
MeSH | Formaldehyde | ||
PubChem CID
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RTECS number
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UNII | |||
UN number | 2209 | ||
CompTox Dashboard (EPA)
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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] | |||
Heat capacity (C)
|
35.387 J·mol−1·K−1 | ||
Std molar
entropy (S⦵298) |
218.760 J·mol−1·K−1 | ||
Std enthalpy of (ΔfH⦵298)formation |
−108.700 kJ·mol−1 | ||
Gibbs free energy (ΔfG⦵)
|
−102.667 kJ·mol−1 | ||
Std enthalpy of (ΔcH⦵298)combustion |
571 kJ·mol−1 | ||
Pharmacology | |||
QP53AX19 (WHO )
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Hazards | |||
GHS labelling: | |||
[9] | |||
Danger | |||
H301, H311, H314, H317, H331, H335, H341, H350, H370[9] | |||
P201, P280, P303+P361+P353, P304+P340+P310, P305+P351+P338, P308+P310[9] | |||
NFPA 704 (fire diamond) | |||
Flash point | 64 °C (147 °F; 337 K) | ||
430 °C (806 °F; 703 K) | |||
Explosive limits
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7–73% | ||
Lethal dose or concentration (LD, LC): | |||
LD50 (median dose)
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100 mg/kg (oral, rat)[12] | ||
LC50 (median concentration)
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333 ppm (mouse, 2 h) 815 ppm (rat, 30 min)[13] | ||
LCLo (lowest published)
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333 ppm (cat, 2 h)[13] | ||
NIOSH (US health exposure limits): | |||
PEL (Permissible)
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TWA 0.75 ppm ST 2 ppm (as formaldehyde and formalin)[10][11] | ||
REL (Recommended)
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Ca TWA 0.016 ppm C 0.1 ppm [15-minute][10] | ||
IDLH (Immediate danger) |
Ca [20 ppm][10] | ||
Safety data sheet (SDS) | MSDS(Archived) | ||
Related compounds | |||
Related aldehydes
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Related compounds
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Formaldehyde (/fɔːrˈmældɪhaɪd/ ⓘ for-MAL-di-hide, US also /fər-/ ⓘ fər-) (systematic name methanal) is an organic compound with the chemical formula CH2O and structure H−CHO, more precisely H2C=O. 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
"Formaldehyde" was first used as a generic trademark in 1893 following a previous trade name, "formalin".[16]
-
Monomeric formaldehyde (subject of this article)
-
Trioxane is a stable cyclic trimer of formaldehyde.
-
Paraformaldehyde is a common form of formaldehyde for industrial applications.
-
Methanediol, the predominant species in dilute aqueous solutions of formaldehyde
Structure and bonding
Molecular formaldehyde contains a central carbon atom with a
Occurrence
Processes in the upper
Formaldehyde and its
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
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
- H + CO → HCO
- HCO + H → CH2O
Synthesis and industrial production
Laboratory synthesis
Formaldehyde was first reported in 1859 by the Russian chemist
Solution routes to formaldehyde also entail oxidation of methanol or methyl iodide.[36]
Industry
Formaldehyde is produced industrially by the catalytic oxidation of
- 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.
- 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
Monomeric CH2O is a gas and is rarely encountered in the laboratory. Aqueous formaldehyde, unlike some other small aldehydes (which need specific conditions to oligomerize through
Gaseous formaldehyde polymerizes at active sites on 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]
Oxidation and reduction
It is readily
In the
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
- 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
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
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
Condensation with acetaldehyde affords
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
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]
Tissue fixative and embalming agent
Formaldehyde preserves or
Formaldehyde-based crosslinking is exploited in
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,[58] 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.[59][60] In 2011, the US National Toxicology Program described formaldehyde as "known to be a human carcinogen".[61][62][63]
Chronic inhalation
This section may require cleanup to meet Wikipedia's quality standards. The specific problem is: A little too scattered among different types of risks. Needs some reorganization. (November 2023) |
However, concerns are associated with chronic (long-term) exposure by inhalation as may happen from
The CDC considers formaldehyde as a systemic poison. Formaldehyde poisoning can cause permanent changes in the nervous system's functions.[68]
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.[69] A 2009 review of studies has shown a strong association between exposure to formaldehyde and the development of childhood asthma.[70]
A theory was proposed for the carcinogenesis of formaldehyde in 1978.
In the residential environment, formaldehyde exposure comes from a number of routes; formaldehyde can be emitted by treated
External media | |
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Audio | |
"Episode 202: Where Have All the FEMA Trailers Gone? Tracing Toxicity from Bust to Boom", Distillations, September 2, 2015, Science History Institute | |
Video | |
Where Have All the Trailers Gone?, Video by Mariel Carr (Videographer) & Nick Shapiro (Researcher), 2015, Science History Institute |
The U.S. EPA allows no more than 0.016 ppm formaldehyde in the air in new buildings constructed for that agency.[88][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.[89] The Federal Emergency Management Agency (FEMA) has also announced limits on the formaldehyde levels in trailers purchased by that agency.[90] 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.[73]
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.[91][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.[92]
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
Formaldehyde levels in air can be sampled and tested in several ways, including impinger, treated sorbent, and passive monitors.[94] The National Institute for Occupational Safety and Health (NIOSH) has measurement methods numbered 2016, 2541, 3500, and 3800.[95]
In June 2011, the twelfth edition of the
Acute irritation and allergic reaction
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
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."[100]
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.[63]
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).[68] 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.[101]
Regulation
Several web articles[
In the United States, Congress passed a bill July 7, 2010, regarding the use of formaldehyde in hardwood
Formaldehyde was declared a toxic substance by the 1999 Canadian Environmental Protection Act.[106]
The
Contaminant in food
Scandals have broken in both the
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.[115] In 2012, 1 billion rupiah (almost US$100,000) of fish imported from Pakistan to Batam, Indonesia, were found laced with formaldehyde.[116]
Formalin contamination of foods has been reported in
Formaldehyde was one of the chemicals used in 19th century industrialised food production that was investigated by Dr.
See also
- Transition metal complexes of aldehydes and ketones includes several complexes of formaldehyde.
- 1,3-Dioxetane
- DMDM hydantoin
- Sawdust | Health impacts of sawdust
- Sulphobes
- Wood glue
- Wood preservative
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{{cite web}}
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- OCLC 1024107182.)
{{cite book}}
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Notes
- ^ 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
- 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 Inventory
- Formaldehyde from ChemSub Online
- Prevention guide—Formaldehyde in the Workplace (PDF) from the IRSST
- Formaldehyde from the National Institute for Occupational Safety and Health
- 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 do?
- Formaldehyde in the Pesticide Properties DataBase (PPDB)