Formaldehyde

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.

[18] The precise molecular geometry of gaseous formaldehyde has been determined by gas electron diffraction[17][19] and microwave spectroscopy.

[23] 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.

[24] 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.

[30] A proposed mechanism for the formation is the hydrogenation of CO ice:[31] HCN, HNC, H2CO, and dust have also been observed inside the comae of comets C/2012 F6 (Lemmon) and C/2012 S1 (ISON).

[32][33] Formaldehyde was discovered in 1859 by the Russian chemist Aleksandr Butlerov (1828–1886) when he attempted to synthesize methanediol ("methylene glycol") from iodomethane and silver oxalate.

[34] In his paper, Butlerov referred to formaldehyde as "dioxymethylen" (methylene dioxide) because his empirical formula for it was incorrect, as atomic weights were not precisely determined until the Karlsruhe Congress.

The compound was identified as an aldehyde by August Wilhelm von Hofmann, who first announced its production by passing methanol vapor in air over hot platinum wire.

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:[40] The silver-based catalyst usually operates at a higher temperature, about 650 °C.

Similarly, formaldehyde hydrates to give the geminal diol methanediol, which condenses further to form hydroxy-terminated oligomers HO(CH2O)nH.

Thus, amines give hexahydro-1,3,5-triazines: Similarly, when combined with hydrogen sulfide, it forms trithiane:[48] In the presence of acids, it participates in electrophilic aromatic substitution reactions with aromatic compounds resulting in hydroxymethylated derivatives: When conducted in the presence of hydrogen chloride, the product is the chloromethyl compound, as described in the Blanc chloromethylation.

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:[51] An aqueous solution of formaldehyde can be useful as a disinfectant as it kills most bacteria and fungi (including their spores).

Despite reports to the contrary,[59] no decision on the inclusion of formaldehyde on Annex I of the Biocidal Products Directive for product-type 22 (embalming and taxidermist fluids) had been made as of September 2009[update].

In photography, formaldehyde is used in low concentrations for the process C-41 (color negative film) stabilizer in the final wash step,[61] as well as in the process E-6 pre-bleach step, to make it unnecessary in the final wash. Due to improvements in dye coupler chemistry, more modern (2006 or later) E-6 and C-41 films do not need formaldehyde, as their dyes are already stable.

[64][65][66] 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).

[69] Formaldehyde inhaled at this concentration may cause headaches, a burning sensation in the throat, and difficulty breathing, and can trigger or aggravate asthma symptoms.

[72] 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.

[84] 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.

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

The three products that emit the highest concentrations are medium density fiberboard, hardwood plywood, and particle board.

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.

[97] Formaldehyde levels in air can be sampled and tested in several ways, including impinger, treated sorbent, and passive monitors.

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.

[53] 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.

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.

[113] 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.

[118][119] 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.

[123] 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.

Structural formula of formaldehyde (with hydrogens)
Structural formula of formaldehyde (with hydrogens)
Spacefill model of formaldehyde
Spacefill model of formaldehyde
Ball and stick model of formaldehyde
Ball and stick model of formaldehyde
NFPA 704 four-colored diamond Health 4: Very short exposure could cause death or major residual injury. E.g. VX gas Flammability 4: Will rapidly or completely vaporize at normal atmospheric pressure and temperature, or is readily dispersed in air and will burn readily. Flash point below 23 °C (73 °F). E.g. propane Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen Special hazard COR: Corrosive; strong acid or base. E.g. sulfuric acid, potassium hydroxide
Two steps in formation of urea-formaldehyde resin, which is widely used in the production of particle board
Injecting a giant squid specimen with formalin for preservation
Some air purifiers include filtering technology that is supposed to lower indoor formaldehyde concentration.