TETRAKIS(HYDROXYMETHYL)PHOSPHONIUM CHLORIDE

TETRAKIS(HYDROXYMETHYL)PHOSPHONIUM CHLORIDE = THPC = PHOSPHONIUM,TETRAKIS(HYDROXMETHYL)-,CHLORIDE(1:1)

CAS Number: 124-64-1
EC Number: 204-707-7
MDL number: MFCD00031687
Chemical formula: (HOCH2)4PCl

Tetrakis(hydroxymethyl)phosphonium chloride (THPC) is an organophosphorus compound with the chemical formula [P(CH2OH)4]Cl. 
Tetrakis(hydroxymethyl)phosphonium chloride is four-coordinate, as is typical for phosphonium salts. 
Tetrakis(hydroxymethyl)phosphonium chloride has applications as a precursor to fire-retardant materials, as well as a microbiocide in commercial and industrial water systems.

The contents of Tetrakis(hydroxymethyl)phosphonium chloride /THPS solutions greatly depend on pH, which is now recognized as a key factor, for example, in metal hydrosol preparations, biocidal activity, and ecotoxicity. 
Tetrakis(hydroxymethyl) phosphonium chloride (THPC) is a water soluble organophosphorus compound, rapid breakdown in the environment, and no or little bioaccumulation.

Tetrakis(hydroxymethyl)phosphonium chloride is a clear slightly viscous,colorless to yellow liquid (20% H2O solution). 
Tetrakis(hydroxymethyl)phosphonium chloride 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(hydroxymethyl)phosphonium chloride is registered under the REACH Regulation and is manufactured in and / or imported to the European Economic Area, for intermediate use.

Tetrakis(hydroxymethyl)phosphonium chloride is an organ phosphorus compound with the cationP(CH2OH)4+ is four-coordinate, as is typical for phosphonium salts. 
Tetrakis(hydroxymethyl)phosphonium chloride has mild acid properties, easily biodegradable and considered environmentally friendly compound.
Tetrakis(hydroxymethyl)phosphonium chloride may be found in combination with ammonia, which is released directly with 

Tetrakis(hydroxymethyl)phosphonium chloride in textile effluent and is a common component of agricultural fertilizers. 
In the environment, Tetrakis(hydroxymethyl)phosphonium chloride breaks down via photodegradation and hydrolysis into phosphorus oxides, ammonia, and chlorine.
Tetrakis(hydroxymethyl)phosphonium chloride is not found in the environment alone, and other chemicals likely to enter freshwater systems include pulses of inorganic nutrients (nitrogen and phosphorus) following application of agricultural fertilizers and municipal wastewater discharge.

Tetrakis(hydroxymethyl)phosphonium chloride may be found in combination with ammonia, which is released directly with Tetrakis(hydroxymethyl)phosphonium chloride in textile effluent and is a common component of agricultural fertilizers. 
Tetrakis(hydroxymethyl)phosphonium chloride is a clear slightly viscous,colorless to yellow liquid (20% H₂O solution).
White or of- white powder or crystlline power,odorless

Very soluble in N,N-Dimethylformamide,Soluble in methanol,Sparingly soluble inglacial acetic acid, Very slightly soluble inchloroform, Practically insoluble in water.
Has Tetrakis(hydroxymethyl)phosphonium chloride's characteristic odor.
Has mild acid properties and are considered corrosive. 
Easily biodegradable and considered environmentally friendly compound.
Tetrakis(hydroxymethyl)phosphonium chloride is a flame retardant for textiles. 

USES and APPLICATIONS of TETRAKIS(HYDROXYMETHYL)PHOSPHONIUM CHLORIDE:
-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, Tetrakis(hydroxymethyl)phosphonium chloride 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. 

-Tetrakis(hydroxymethyl)phosphonium chloride, which is a water-soluble, organophosphorus salt, is mainly used by textile industries as a flame retardant and crease resistant for cotton and cellulose fabrics. 
-Tetrakis(hydroxymethyl)phosphonium chloride, as well as THPS, are used in the flame-resistant fabric industry to improve the tear strength of cotton and other cellulosic fabrics.

-Tetrakis(hydroxymethyl)phosphonium chloride can be also used as tanning agents in the leather industry.
-Tetrakis(hydroxymethyl)phosphonium chloride is an anti-microbial agent against SRB (Sulfate Reducing Bacteria) with minimum effects on the environment used in oilfield drilling and production applications. 
-Tetrakis(hydroxymethyl)phosphonium chloride can be also used as an iron control chemistry to prevent iron sulfide scale common in the oil and gas industry.

-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 is used at industrial sites and in manufacturing.

-Tetrakis(hydroxymethyl)phosphonium chloride has an industrial use resulting in manufacture of another substance (use of intermediates).
-Tetrakis(hydroxymethyl)phosphonium chloride is used for the manufacture of chemicals.
-As an intermediate step in further manufacturing of another substance (use of intermediates).

-The use of tetrakis-(hydroxymethyl)-phosphonium chloride (THPC) as simultaneous reducing agent and stabilizing ligand has been extended to the single-step synthesis at room temperature of a wide variety of monometallic nanoparticles and bi-/tri- metallic nanoalloys containing noble metals with potential application in catalysis. 
-Tetrakis(hydroxymethyl) phosphonium salts are used to produce crease- resistant and flame-retardant finishes on textile fabrics, including children's nightwear. 

-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. 
-Tetrakis(hydroxymethyl)phosphonium chloride is used as a reducing agent and stabilizing ligand for the synthesis of gold nanoparticles (AuNPs) from gold(III) chloride trihydrate (HAuCl4.3H2O). 

-Tetrakis(hydroxymethyl)phosphonium chloride is used to make crease-resistant and flame-retardant finishes for textiles, e.g., children's sleepwear.
-Tetrakis(hydroxymethyl)phosphonium chloride is used as a disinfectant--effective against escherichia coli and staphylococcus aureus, and foot-and-mouth disease virus of cattle.

-Flame retardant for the finishing of cotton and polyester fabrics. 
-Applied to pure cotton or polyester cotton as well as other fabrics. 
-Treated textiles show excellent flame-retarding, handling, wash resistance, and low tear strength effects as opposed to untreated fabrics.

-Tetrakis(hydroxymethyl)phosphonium chloride has been used as a reducing agent and stabilizing ligand for the synthesis of gold nanoparticles (AuNPs) from gold(III) chloride trihydrate (HAuCl4.3H2O). 
-Tetrakis(hydroxymethyl)phosphonium chloride 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.

-A broad spectrum disinfectant and act as chemical intermiedates.
-The use of tetrakis-(hydroxymethyl)-phosphonium chloride (THPC) as simultaneous reducing agent and stabilizing ligand has been extended to the single-step synthesis at room temperature of a wide variety of monometallic nanoparticles and bi-/tri- metallic nanoalloys containing noble metals with potential application in catalysis. 

-Tetrakis(hydroxymethyl)phosphonium chloride is used to replace old and toxic fungicides. 
-Tetrakis(hydroxymethyl)phosphonium chloride is used in industrial water treatment, papermaking, tanning, oilfield exploitation and production, etc.
-Tetrakis(hydroxymethyl)phosphonium chloride is an intermediate in the preparation of the water-soluble ligand 1,3,5-triaza-7-phosphaadamantane (PTA). 

-Tetrakis(hydroxymethyl)phosphonium chloride can also be used to synthesize the heterocycle, N-boc-3-pyrroline by ring-closing metathesis using Grubbs' catalyst (bis(tricyclohexylphosphine)benzylidineruthenium dichloride). 
-Tetrakis (hydroxymethyl) phosphonium chloride uses and applications include: Phase transfer catalyst; polymerization catalyst; chemical intermediate; flame-retarding agent for cotton fabrics
-Tetrakis(hydroxymethyl)phosphonium chloride is used for flame retardants, oil field, and textile applications. 

-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.
-Tetrakis hydroxymethyl phosphonium chloride (THPC), a water-soluble organophosphorus flame retardant formed from the reaction of hydrochloric acid, formaldehyde, and phosphine, is used to produce flame and crease resistant clothing.
-Tetrakis(hydroxymethyl)phosphonium chloride is a useful research chemical.

SYNTHESIS AND REACTIONS of TETRAKIS(HYDROXYMETHYL)PHOSPHONIUM CHLORIDE:
Tetrakis(hydroxymethyl)phosphonium chloride can be synthesized with high yield by treating phosphine with formaldehyde in the presence of hydrochloric acid.

PH3 + 4 H2C=O + HCl → [P(CH2OH)4]Cl
Tetrakis(hydroxymethyl)phosphonium chloride converts to tris(hydroxymethyl)phosphine upon treatment with aqueous sodium hydroxide:

[P(CH2OH)4]Cl + NaOH → P(CH2OH)3 + H2O + H2C=O + NaCl

APPLICATION in TEXTILES of TETRAKIS(HYDROXYMETHYL)PHOSPHONIUM CHLORIDE:
Tetrakis(hydroxymethyl)phosphonium chloride 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 Tetrakis(hydroxymethyl)phosphonium chloride by the Proban Process, in which 
Tetrakis(hydroxymethyl)phosphonium chloride is treated with urea. 
The urea condenses with the hydroxymethyl groups on Tetrakis(hydroxymethyl)phosphonium chloride. 
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.

Tetrakis(hydroxymethyl)phosphonium chloride can condense with many other types of monomers in addition to urea. 
These monomers include amines, phenols, and polybasic acids and anhydrides.

PHYSICAL and CHEMICAL PROPERTIES of TETRAKIS(HYDROXYMETHYL)PHOSPHONIUM CHLORIDE:
Molar mass: 190.56 g·mol−1
Appearance: crystalline
Density: 1.341 g/cm3
Melting point: 150 °C (302 °F; 423 K)
Physical state: Liquid
Appearance: Clear. light brown.
Color: No data available on colour

Odor: Pungent
Odor threshold: No data available
pH: No data available
pH solution: 3 – 5
Melting point: No data available
Freezing point: ≈ 0 °C
Boiling point: ≈ 239 °F
Flash point: No data available
Relative evaporation rate (butyl acetate=1): No data available

Flammability (solid, gas): Non flammable.
Vapor pressure: Not determined
Relative vapor density at 20 °C : > 1
Relative density: No data available
Specific gravity / density: 1.34
Molecular mass: 190.57 g/mol
Solubility: Soluble in water.
Water: 4 g/100ml
Partition coefficient n-octanol/water (Log Pow): -9.77 (QSAR)

FIRST AID MEASURES of TETRAKIS(HYDROXYMETHYL)PHOSPHONIUM CHLORIDE:
-First-aid measures general : 
*If exposed or concerned: 
Get medical advice/attention. 

-First-aid measures after inhalation : 
Get medical advice/attention.

-First-aid measures after skin contact : 
Rinse skin with water/shower. 
Get medical advice/attention. 

-First-aid measures after eye contact : 
Remove contact lenses, if present and easy to do. 
Continue rinsing. 

-First-aid measures after ingestion : 
*If swallowed: 
Rinse mouth. 

ACCIDENTAL RELEASE MEASURES of TETRAKIS(HYDROXYMETHYL)PHOSPHONIUM CHLORIDE:
-General Measures:

--For emergency responders:
*Emergency procedures: 
Ventilate area.

-Methods and material for containment and cleaning up:
For containment: 
Collect spillage. 

*Methods for cleaning up: 
Collect spillage. 
Use suitable disposal containers. 

FIRE FIGHTING MEASURES of TETRAKIS(HYDROXYMETHYL)PHOSPHONIUM CHLORIDE:
-Suitable (and unsuitable) extinguishing media:
*Suitable extinguishing media: 
Dry powder. 
Carbon dioxide. 
Water spray. 
foam.
*Unsuitable extinguishing media: 
No knowledge. 

EXPOSURE CONTROLS/PERSONAL PROTECTION of TETRAKIS(HYDROXYMETHYL)PHOSPHONIUM CHLORIDE:
-Control parameters:
*Ingredients with workplace control parameters:
-Exposure controls:

--Personal protective equipment:
*Eye/face protection:
Use equipment for eye protection.

*Skin protection:
Handle with gloves. 
Wash and dry hands.

Full contact:
Material: Nitrile rubber
Minimum layer thickness: 0,11 mm
Break through time: 480 min

Splash contact:
Material: Nitrile rubber
Minimum layer thickness: 0,11 mm
Break through time: 480 min

*Body Protection:
Use protective clothing

HANDLING and STORAGE of TETRAKIS(HYDROXYMETHYL)PHOSPHONIUM CHLORIDE:
-Precautions for safe handling:
Keep container tightly closed. 
Use personal protective equipment as required. 
Do not eat, drink or smoke when using this product. 

*Hygiene measures: 
Wash hands thoroughly after handling. 

-Conditions for safe storage, including any incompatibilities:
*Storage conditions: 
Keep only in original container. 
Keep container tightly closed.

*Storage area: 
Keep container tightly closed and in a well-ventilated place.

STABILITY and REACTIVITY of TETRAKIS(HYDROXYMETHYL)PHOSPHONIUM CHLORIDE:
-Reactivity:
No data available
-Chemical stability:
The product is chemically stable under standard ambient conditions (room temperature).

SYNONYMS
tetrakis hydroxymethyl phosphonium chloride
THPC
Pyroset TKC
Retardol C
Proban CC
tetramethylolphosphonium acetate
tetramethylolphosphonium chloride
tetramethylolphosphonium hydroxide
tetramethylolphosphonium nitrate
tetramethylolphosphonium oxalate (2:1)
tetramethylolphosphonium phosphate (3:1)
tetramethylolphosphonium sulfate (2:1)
Phosphonium, tetrakis(hydroxymethyl)-, chloride
Pyroset TKC
Tetrahydroxymethylphosphonium chloride
Tetrakis(hydroxymethyl)phosphochloride
Tetrakis(hydroxymethyl)phosphonium chloride
Tetramethylolphosphonium chloride
Phosphonium, tetrakis(hydroxymethyl)-, chloride (1:1)