Paraformaldehyde

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Paraformaldehyde
Paraformaldehyd.svg
Names
IUPAC name
Polyoxymethylene
Identifiers
ChemSpider
  • none
ECHA InfoCard 100.108.270
Properties
OH(CH2O)nH (n = 8 - 100)
Appearance white crystalline solid
Density 1.42 g·cm−3 (25 °C)
Melting point 120 °C (248 °F; 393 K)
low
Hazards
Safety data sheet Oxford MSDS
Toxic (T); Corrosive (C)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
No verify (what is YesYNo ?)
Infobox references

Paraformaldehyde (PFA) is the smallest polyoxymethylene, the polymerization product of formaldehyde with a typical degree of polymerization of 8–100 units. Paraformaldehyde commonly has a slight odor of formaldehyde due to decomposition. Paraformaldehyde is a poly-acetal.

Synthesis[edit]

Paraformaldehyde forms slowly in aqueous formaldehyde solutions as a white precipitate, especially if stored in the cold. Formalin actually contains very little monomeric formaldehyde; most of it forms short chains of polyformaldehyde. A small amount of methanol is often added as a stabilizer to limit the extent of polymerization.

Reactions[edit]

Paraformaldehyde can be depolymerized to formaldehyde gas by dry heating[1] and to form a formaldehyde solution by water in the presence of a base or heat. The very pure formaldehyde solutions obtained in this way are used as a fixative for microscopy and histology.

The resulting formaldehyde gas from dry heating paraformaldehyde is flammable.

Uses[edit]

Once paraformaldehyde is depolymerized, the resulting formaldehyde may be used as a fumigant, disinfectant, fungicide, and fixative. Longer chain-length (high molecular weight) polyoxymethylenes are used as a thermoplastic and are known as polyoxymethylene plastic (POM, Delrin). It was used in the past in the discredited Sargenti method of root canal treatment.[2]

Paraformaldehyde is not a fixative; it must be depolymerized to formaldehyde in solution. In cell culture, a typical formaldehyde fixing procedure would involve using a 4% formaldehyde solution in phosphate buffered saline (PBS) on ice for 10 minutes.

Paraformaldehyde is also used to crosslink proteins to DNA, as used in ChIP (Chromatin Immuno Precipitation) which is a technique to determine which part of DNA certain proteins are binding to.

Paraformaldehyde can be used as a substitute of aqueous formaldehyde to produce the resinous binding material, which is commonly used together with melamine, phenol or other reactive agents in the manufacturing of particle board, medium density fiberboard and plywood.[3]

Toxicity[edit]

As a formaldehyde releasing agent, paraformaldehyde is a potential carcinogen.[4] Its acute oral median lethal dose in rats is 592 mg/kg.[5]

See also[edit]

References[edit]

  1. ^ Yates, J (1973). "Adsorption and decomposition of formaldehyde on tungsten (100) and (111) crystal planes". Journal of Catalysis. 30 (2): 260. doi:10.1016/0021-9517(73)90073-0. 
  2. ^ http://www.dentalwatch.org/questionable/sargenti/overview.html
  3. ^ http://dovechem.com/en/paraformaldehyde-3
  4. ^ Cogliano, Vincent; Grosse, Yann; Baan, Robert; Straif, Kurt; Secretan, Béatrice; Ghissassi, Fatiha El (September 2004). "Advice on formaldehyde and glycol ethers". The Lancet Oncology. 5 (9): 528. doi:10.1016/S1470-2045(04)01562-1. Retrieved 27 October 2015. 
  5. ^ "MSDS - 158127 SAFETY DATA SHEET - Paraformaldehyde". SIGMA-ALDRICH. Retrieved 27 October 2015.