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CAS: 124-64-1
Tetrakis(hydroxymethyl)phosphonium chloride (THPC) is an organophosphorus compound with the chemical formula [P(CH2OH)4]Cl. The cation P(CH2OH)4+ is four-coordinate, as is typical for phosphonium salts. THPC has applications as a precursor to fire-retardant materials,[1] as well as a microbiocide in commercial and industrial water systems.
Tetrakis(hydroxymethyl)phosphonium chloride; 124-64-1; THPC; Pyroset TKC; TETRAMETHYLOLPHOSPHONIUM CHLORIDE; Phosphonium, tetrakis(hydroxymethyl)-, chloride; NCI-C55061; Tetra(hydroxymethyl)phosphonium chloride; UNII-58WB2XCF8I; Tetrakis(hydroxymethyl)phosphochloride; 58WB2XCF8I; tetrakis(hydroxymethyl)phosphanium;chloride ;Retardol C; Phosphonium, tetrakis(hydroxymethyl)-, chloride (1:1); Proban CC; CCRIS 317; HSDB 2923; tetrakis(hydroxymethyl)phosphanium chloride; EINECS 204-707-7; Tetrahydroxymethylphosphonium chloride; NSC 30698; Tetrakis(hydroxymethyl)phosphonium Chloride (ca. 80% in Water); AI3-22268; Tetrakis(hydroxymethyl)phosphonium chloride, ca. 80% solution in water; Tetrakis-(hydroxymethyl)fosfoniumchlorid [Czech]; Tetrakis-(hydroxymethyl)fosfoniumchlorid; ACMC-1BPFQ; DSSTox_CID_1330; EC 204-707-7; DSSTox_RID_76085; DSSTox_GSID_21330; SCHEMBL196471; CHEMBL2131547; DTXSID5021330; WLN: Q1P1Q1Q1Q & G; NSC30698; Tox21_302070; ANW-43807; MFCD00031687; NSC-30698; AKOS015918384; Tetra(hydroxymethyl)phosphoniumchloride; NE10887; NCGC00164162-01; NCGC00255382-01; CAS-124-64-1; DB-007909; tetrakis-(hydroxymethyl)phosphonium chloride; FT-0631726; Phosphonium, chloro-tetrakis(hydroxymethyl)-; EN300-19000; Q7706566; 359406-89-6
THPC can be synthesized with high yield by treating phosphine with formaldehyde in the presence of hydrochloric acid.[1]
PH3 + 4 H2C=O + HCl → [P(CH2OH)4]Cl
THPC converts to tris(hydroxymethyl)phosphine upon treatment with aqueous sodium hydroxide:[2]
[P(CH2OH)4]Cl + NaOH → P(CH2OH)3 + H2O + H2C=O + NaCl
THPC has industrial importance in the production of crease-resistant and flame-retardant finishes on cotton textiles and other cellulosic fabrics. A flame-retardant finish can be prepared from THPC by the Proban Process,[4] in which THPC is treated with urea. The urea condenses with the hydroxymethyl groups on THPC. The phosphonium structure is converted to phosphine oxide as the result of this reaction.
[P(CH2OH)4]Cl + NH2CONH2 → (HOCH2)2POCH2NHCONH2 + HCl + HCHO + H2 + H2O
This reaction proceeds rapidly, forming insoluble high molecular weight polymers. The resulting product is applied to the fabrics in a "pad-dry process." This treated material is then treated with ammonia and ammonia hydroxide to produce fibers that are flame-retardant.
THPC can condense with many other types of monomers in addition to urea. These monomers include amines, phenols, and polybasic acids and anhydrides.
Tris(hydroxymethyl)phosphine, which is derived from tetrakis(hydroxymethyl)phosphonium chloride, is an intermediate in the preparation of the water-soluble ligand 1,3,5-triaza-7-phosphaadamantane (PTA). This conversion is achieved by treating hexamethylenetetramine with formaldehyde and tris(hydroxymethyl)phosphine.[6]
Tris(hydroxymethyl)phosphine can also be used to synthesize the heterocycle, N-boc-3-pyrroline by ring-closing metathesis using Grubbs' catalyst (bis(tricyclohexylphosphine)benzylidineruthenium dichloride). N-Boc-diallylamine is treated with Grubbs' catalyst, followed by tris(hydroxymethyl)phosphine. The carbon-carbon double bonds undergo ring closure, releasing ethene gas, resulting in N-boc-3-pyrroline.[7] The hydroxymethyl groups on THPC undergo replacement reactions when THPC is treated with α,β-unsaturated nitrile, acid, amide, and epoxides. For example, base induces condensation between THPC and acrylamide with displacement of the hydroxymethyl groups. (Z = CONH2)
[P(CH2OH)4]Cl + NaOH + 3CH2=CHZ → P(CH2CH2Z)3 + 4CH2O + H2O + NaCl
Similar reactions occur when THPC is treated with acrylic acid; only one hydroxymethyl group is displaced, however.
Uses at industrial sites
This substance has an industrial use resulting in manufacture of another substance (use of intermediates).
This substance is used for the manufacture of: chemicals.
Release to the environment of this substance can occur from industrial use: as an intermediate step in further manufacturing of another substance (use of intermediates).
Manufacture
Release to the environment of this substance can occur from industrial use: manufacturing of the substance.
At present, tetra-hydroxymethyl phosphonium chloride (THPC ) is widely used in flame retardant finishing, industrial water treatment and leather manufacture industry etc., and its decomposition will affect the actual application. So the thermal decomposition and acid-alkali decomposition of THPC were studied by 31 P nuclear magnetism resomance (31P NMR), thermo-gravimetric analysis (TGA) and differential scanning calorimet ry (DSC ) respectively. The results showed that THPC solution was stable when pH9.0, all of the phosphorus compounds converted to TrHPO. Consequently, THPC content decreased when pH of the THPC solution rose. Thermal decomposition experiment was also carried out.The structure of THPC began to change when heated to 152.4℃ and lose weight at 184.41℃. Therefore, application temperature should be below 152℃, which could give a favorable guide in THPC application.
Tetra-hydroxymethyl phosphonium chloride (THPC) was first reported in 1921 by Hoffman[1] . It is a rather unusual and little-investigated organic phosphorus compound that undergoes many interesting reactions [2] . At present, it is widely used in chemical engineering field, such as flame retardant finishing[3] , industrial water treatment [4] , intermediate producing [5] , leather manufacture industry and so on. In THPC applying process,
THPC will decompose because of heating or neutralizing. At the same time, free formaldehyde and phosphine compounds will be generated, which may influence on the actual application and products quality [7, 8] . In order to make clear with the THPC decomposition rule, the reaction of thermal decomposition and acid-alkali decomposition were studied by THPC content determination, free formaldehyde content determination, 31P NMR analysis, etc
Tetrakis(hydroxymethyl)phosphonium chloride (THPC) and sulfate (THPS) are of importance in the textile industry as flame retardants, in the oil industry as scale-removers, as biocides for water systems, in the leather industry as tanning agents, in nanochemistry as reductants and stabilizers of nanoparticles, and as oxygen-scavengers in medical uses. In the majority of cases, THPC and THPS themselves are not chemically active and solely play a role of reservoirs for the more reactive species tris(hydroxymethyl)phosphine (THP) and/or formaldehyde. The contents of THPC/THPS solutions greatly depend on pH, which is now recognized as a key factor, for example, in metal hydrosol preparations, biocidal activity, and ecotoxicity.
Degration of THPC is spontaneous at basic pH. The abstaction of the ß-proton of 1-hydroxyalkyl phoshphonium ion results in the release of formaldehyde and the in situ formation of Tri hydroxymethyl phosphine (THP), a strong reducing agent. It is able to reduce disulphide aminoacid (cystine) residues of microbial cell entities to SH amino (cysteine) components. The phosphine is converted (inactivated) to phosphine oxide. It should be noted that the chemistry of the Tetrakis hydroxymethyl phosphonium ion is driven by the electrochemistry of the phosphine species. Phosphines exist in the +3 oxidation state and most phosphine chemistry results in a phosphorus +5 species.
Its reactivity as well as the hydrophilic nature makes bioaccumulation of THPC unlikely. An estimation of the BCF by means of EPIWIN supports negative bioaccumulation potential. THPC has been shown to react electrophilically with guanosine at the 2-amino position to give N-(bis (hydroxymethyl) phosphino) methyl guanosine. In vitro, THPC is genotoxic. In vivo, no mutagenicity has been found.
Bioaccumulation of this ionic compound is not expected because of the low log Pow.
THPC is a new class anti-microbial agent, with minimum effects on the environment. THPC's benefits include low toxicity, low dosage and rapid breakdown in the environment.
PACKING
250kg per UN approved PE drum
APPLICATIONS
· Industrial / Commercial Water Treatment - control of bacterial growth
· Oilfield - control of bacterial growth
· Textiles
· Disinfectants
· Chemical Intermediate
The sizes, size distributions, morphologies, chemical compositions, and optical properties of the THPC-metal nanoparticles (THPC-mNPs) were characterized by transmission electron microscopy (TEM), selected area electron diffraction (SAED) analysis, X-ray photoelectron spectroscopy (XPS), Fourier transform-infrared (FT-IR) spectroscopy, and ultraviolet-visible (UV-vis) spectroscopy. Characterization of the resulting nanoshells was performed using scanning electron microscopy (SEM), TEM, and UV-vis spectroscopy. While the use of THPC-gold nanoparticles to seed metal nanoshells is well known, the process is time consuming and requires highly concentrated seeding solutions. Our THPC-mNPs were used to seed the growth of a variety of metal nanoshells in rapid fashion, including the successful generation of highly uniform platinum and palladium nanoshells grown from their own seeds.
Applications Carbic Anhydride is an intermediate used to prepare Endo-2,3-Norbornanedicarboximide (N661225) which is used to prepare piperidinylbenzisoxazole antipsychotic drugs.
Tetrakis(hydroxymethyl) phosphonium chloride (THPC) is a water soluble organophosphorus compound that has low toxicity, rapid breakdown in the environment, and no or little bioaccumulation.
Flame Retardants & Textile Auxiliaries
THPC, as well as THPS, are used in the flame-resistant fabric industry to improve the tear strength of cotton and other cellulosic fabrics.
THPC can be also used as tanning agents in the leather industry.
Oilfield Operations
THPC is an anti-microbial agent against SRB (Sulfate Reducing Bacteria) with minimum effects on the environment used in oilfield drilling and production applications. THPC 80% can be also used as an iron control chemistry to prevent iron sulfide scale common in the oil and gas industry.
Industrial and Commercial Water Treatment
Tetrakis Hydroxymethyl Phosphonium chloride (THPC) can be also used for the control of bacteria, algae, and fungi in industrial/commercial recirculating cooling water systems, in heat transfer water systems, and in industrial process water systems.
Tetrakis(hydroxymethyl)phosphonium chloride solution (80% in H2O) has been used as a reducing agent and stabilizing ligand for the synthesis of gold nanoparticles (AuNPs) from gold(III) chloride trihydrate
It is a tetra-functional, amine-reactive, aqueous crosslinker that can be used for tuning the properties of protein-based hydrogels for 3D cell encapsulation applications.
Tetrakis(hydroxyethyl) phosphonium salts are used to produce crease-resistant flame-retardant finishes on cotton textiles and cellulosic fabrics. llPC, THPS and THPA/P can be cured on the fabric with amine compounds (e.g., ammonia, urea, melamine-formaldehyde resins) to form durable, cross-linked flame-retardant resin finish es. Recently, THPS has largely replaced THPC in commercial use; THPA/P has never been a major commercial product.
Many co-reactants have been used to form flame-retardant finishes with these compounds. One of the most popular processes has been the tetrakis(hydroxyethyl) phosphonium hydroxide-ammonIa finish, in which llPS is converted to a free organic base and th en cured on the fabric by reaction with ammonia gas
Organophosphorus flame retardants, such as tetrakis
hydroxymethyl phosphonium chloride (THPC), often have similar applications to and are generally not as persistent as halogenated flame retardants. Additionally, other contaminants from industry and agriculture are likely to accompany flame retardant chemicals in surface waters. THPC may be found in combination with ammonia, which is released directly with THPC in textile effluent and is a common component of agricultural fertilizers.
Ammonia is a form of inorganic nitrogen that can stimulate primary production, but in excess can shift phytoplankton community composition to dominance by less edible or harmful species
Used to make crease-resistant and flame-retardant finishes for textiles, e.g., children's sleepwear;
Used as a disinfectant--effective against escherichia coli and staphylococcus aureus, and foot-and-mouth disease virus of cattle
Degrades rapidly in the environment in the presence of moisture and sunlight; Tetrakis (hydroxymethyl) phosphonium sulfate (THPS) was a sensitizer in 14 of 20 guinea pigs; Tetrakis (hydroxymethyl) phosphonium chloride (THPC) was also designated a dermal sensitizer.
Textile
Textile operations include fiber synthesis, weaving, manufacturing, dyeing, and finishing.
Using Disinfectants or Biocides
Disinfectants are chemicals used to inhibit or kill microorganisms. Disinfectants are also called antiseptics or biocides. Disinfectants are generally used in physical media (solutions or on surfaces) while antiseptics are applied to skin or other living tissue. Some of these agents are also used as preservatives for food, drugs, and other domestic and industrial products. Many of these chemicals are skin and respiratory sensitizers. The following can cause occupational asthma: glutaraldehyde, formaldehyde, sodium bisulfite, chloramine T, hexachlorophene, chlorohexidine, benzalkonium chloride, isononanoyl oxybenzene sulfonate, lauryl dimethyl benzyl ammonium chloride, and isothiazolinones. A study of 175 workers exposed to chloramines, aldehydes, and quaternary ammonium disinfectants in the food industry showed increased acute irritation symptoms but not chronic respiratory symptoms.
IUPAC
Tetrakis(hydroxymethyl) phosphonium chloride
tetrakis(hydroxymethyl)phosphanium chloride
tetrakis(hydroxymethyl)phosphanium;chloride
Tetrakis(hydroxymethyl)phosphonium chloride
tetrakis(hydroxymethyl)phosphonium chloride
tetrakis(hydroxymethyl)phosphonium chloride
THPC
TRADE
Tetrakis Hydroxymethyl Phosphonium Chloride
THPC
