Paraformaldehyde (PFA) is the smallest

polyoxymethylene Polyoxymethylene (POM), also known as acetal, polyacetal, and polyformaldehyde, is an engineering thermoplastic used in precision parts requiring high stiffness, low friction, and excellent dimensional stability. As with many other synthetic pol ...

, the

polymerization In polymer chemistry, polymerization (American English), or polymerisation (British English), is a process of reacting monomer, monomer molecules together in a chemical reaction to form polymer chains or three-dimensional networks. There are ...

product of

formaldehyde Formaldehyde ( , ) (systematic name methanal) is a naturally occurring organic compound with the formula and structure . The pure compound is a pungent, colourless gas that polymerises spontaneously into paraformaldehyde (refer to section F ...

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 In organic chemistry, an acetal is a functional group with the connectivity . Here, the R groups can be organic fragments (a carbon atom, with arbitrary other atoms attached to that) or hydrogen, while the R' groups must be organic fragments no ...

Synthesis

Paraformaldehyde forms slowly in aqueous

solutions as a white precipitate, especially if stored in the cold.

Formalin Formaldehyde ( , ) (systematic name methanal) is a naturally occurring organic compound with the formula and structure . The pure compound is a pungent, colourless gas that polymerises spontaneously into paraformaldehyde (refer to section Fo ...

actually contains very little monomeric formaldehyde; most of it forms short chains of polyformaldehyde. A small amount of

methanol Methanol (also called methyl alcohol and wood spirit, amongst other names) is an organic chemical and the simplest aliphatic alcohol, with the formula C H3 O H (a methyl group linked to a hydroxyl group, often abbreviated as MeOH). It is a ...

is often added as a stabilizer to limit the extent of

Reactions

Paraformaldehyde can be depolymerized to formaldehyde gas by dry heating and to formaldehyde solution by

water Water (chemical formula ) is an inorganic, transparent, tasteless, odorless, and nearly colorless chemical substance, which is the main constituent of Earth's hydrosphere and the fluids of all known living organisms (in which it acts as a ...

in the presence of a base, an acid or heat. The high purity formaldehyde solutions obtained in this way are used as a fixative for

microscopy Microscopy is the technical field of using microscopes to view objects and areas of objects that cannot be seen with the naked eye (objects that are not within the resolution range of the normal eye). There are three well-known branches of micr ...

and

histology Histology, also known as microscopic anatomy or microanatomy, is the branch of biology which studies the microscopic anatomy of biological tissues. Histology is the microscopic counterpart to gross anatomy, which looks at larger structures vis ...

. The resulting formaldehyde gas from dry heating paraformaldehyde is flammable.

Uses

Once paraformaldehyde is depolymerized, the resulting formaldehyde may be used as a

fumigant Fumigation is a method of pest control or the removal of harmful micro-organisms by completely filling an area with gaseous pesticides—or fumigants—to suffocate or poison the pests within. It is used to control pests in buildings ( ...

disinfectant A disinfectant is a chemical substance or compound used to inactivate or destroy microorganisms on inert surfaces. Disinfection does not necessarily kill all microorganisms, especially resistant bacterial spores; it is less effective than st ...

fungicide Fungicides are biocidal chemical compounds or biological organisms used to kill parasitic fungi or their spores. A fungistatic inhibits their growth. Fungi can cause serious damage in agriculture, resulting in critical losses of yield, quality, ...

, and fixative. Longer chain-length (high molecular weight) polyoxymethylenes are used as a

thermoplastic A thermoplastic, or thermosoft plastic, is any plastic polymer material that becomes pliable or moldable at a certain elevated temperature and solidifies upon cooling. Most thermoplastics have a high molecular weight. The polymer chains associate ...

and are known as

plastic (POM, ''Delrin''). It was used in the past in the discredited Sargenti method of

root canal treatment Root canal treatment (also known as endodontic therapy, endodontic treatment, or root canal therapy) is a treatment sequence for the infected pulp of a tooth which is intended to result in the elimination of infection and the protection of ...

. 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 Phosphate-buffered saline (PBS) is a buffer solution (pH ~ 7.4) commonly used in biological research. It is a water-based salt solution containing disodium hydrogen phosphate, sodium chloride and, in some formulations, potassium chloride and potass ...

(PBS) on ice for 10 minutes. In histology and pathology specimens preparation, usually, the fixation step is performed using 10% Neutral Buffered Formalin (4% formaldehyde) for, at least, 24 hours. Paraformaldehyde is also used to crosslink proteins to DNA, as used in ChIP (

chromatin immunoprecipitation Chromatin immunoprecipitation (ChIP) is a type of immunoprecipitation experimental technique used to investigate the interaction between proteins and DNA in the cell. It aims to determine whether specific proteins are associated with specific genom ...

) 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 Melamine is an organic compound with the formula C3H6N6. This white solid is a trimer of cyanamide, with a 1,3,5-triazine skeleton. Like cyanamide, it contains 67% nitrogen by mass, and its derivatives have fire retardant properties due t ...

phenol Phenol (also called carbolic acid) is an aromatic organic compound with the molecular formula . It is a white crystalline solid that is volatile. The molecule consists of a phenyl group () bonded to a hydroxy group (). Mildly acidic, it req ...

or other reactive agents in the manufacturing of

particle board Particle board, also known as chipboard or low-density fiberboard, is an engineered wood product manufactured from wood chips and a synthetic resin or other suitable binder, which is pressed and extruded. Particle board is often confused with ori ...

, medium density

fiberboard Fiberboard (American English) or fibreboard (British English) is a type of engineered wood product that is made out of wood fibers. Types of fiberboard (in order of increasing density) include particle board or low-density fiberboard (LDF), medi ...

and

plywood Plywood is a material manufactured from thin layers or "plies" of wood veneer that are glued together with adjacent layers having their wood grain rotated up to 90 degrees to one another. It is an engineered wood from the family of manufactured ...

Toxicity

As a formaldehyde releasing agent, paraformaldehyde is a potential

carcinogen A carcinogen is any substance, radionuclide, or radiation that promotes carcinogenesis (the formation of cancer). This may be due to the ability to damage the genome or to the disruption of cellular metabolic processes. Several radioactive substan ...

. Its acute oral

median lethal dose In toxicology, the median lethal dose, LD50 (abbreviation for "lethal dose, 50%"), LC50 (lethal concentration, 50%) or LCt50 is a toxic unit that measures the lethal dose of a toxin, radiation, or pathogen. The value of LD50 for a substance is the ...

in rats is 592 mg/kg.{{cite web, title=MSDS - 158127 SAFETY DATA SHEET - Paraformaldehyde, url=https://www.sigmaaldrich.com/US/en/product/sial/158127 , publisher=SIGMA-ALDRICH, access-date=15 February 2022

References

Polyethers Hemiacetals

Synthesis

Reactions

Uses

Toxicity

See also

References