TETRAKIS(HYDROXYMETHYL)PHOSPHONIUM CHLORIDE
TETRAKIS(HYDROXYMETHYL)PHOSPHONIUM CHLORIDE
CAS: 124-64-1, 7732-18-5
Molecular Formula: (HOCH2)4PCl
Molecular Weight (g/mol): 190.56
Alternate Names: THPC solution
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, as well as a microbiocide in commercial and industrial water systems.
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 has characteristic odor.
THPC is non-flammable.
Tetrakis(hydroxymethyl)phosphonium chloride has mild acid properties and are considered corrosive.
Tetrakis(hydroxymethyl)phosphonium chloride is easily biodegradable and considered environmentally friendly compound.
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.
This review is intended to reveal and explain the complex behavior of THP and (HOCH2)4P+ salts in aqueous solutions, conditions that might lead to potential hazardous compounds such as formaldehyde, hydrogen gas, phosphine PH3, and bis(chloromethyl)ether.
Applications of Tetrakis(hydroxymethyl)phosphonium chloride:
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 (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.
Has been replacing older, more toxic biocides in the following markets/customers served: Industrial Water Treatment; Paper Manufacture; Leather Tanning; Oil Field Drilling&Production
Chemical Name or Material: Tetrakis(hydroxymethyl)phosphonium chloride
Density: 1.3400g/mL
Boiling Point: 115.0°C
MDL Number: MFCD00031687
Quantity: 100mL
THPC is an organ phosphorus compound with the cationP(CH2OH)4+ is four-coordinate, as is typical for phosphonium salts.
THPC has mild acid properties, easily biodegradable and considered environmentally friendly compound.
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.
The colloidal suspensions exhibit mean diameters below 4 nm with narrow size distributions and high stability in aqueous solution for long periods of time.
Solubility Information
Solubility in water: soluble.
InChI Key: AKXUUJCMWZFYMV-UHFFFAOYSA-M
IUPAC Name: tetrakis(hydroxymethyl)phosphanium;chloride
PubChem CID: 31298
Physical Form: Solution
Applications of Tetrakis(hydroxymethyl)phosphonium chloride:
1. THPC is used as flame retardant in fabric finishing industry which applied to pure cotton, terylene(Dacron) and other fabric.
After treated with it fabric will have flame-retardant property permanently, and the intrinsic property of fabric will not be affected.
2. THPC also can be used as additive flame retardant for plastic and papery material.
Synthesis and reactions of Tetrakis(hydroxymethyl)phosphonium chloride:
THPC 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
THPC converts to tris(hydroxymethyl)phosphine upon treatment with aqueous sodium hydroxide:
[P(CH2OH)4]Cl + NaOH → P(CH2OH)3 + H2O + H2C=O + NaCl
Tetrakis(hydroxymethyl)phosphonium chloride Application in textiles:
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, 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.
Form: Liquid
Usage/Application: Commercial
Chemical Name: THPC 80%
PH Value: 3.5-5.0
Tris(hydroxymethyl)phosphine and its uses
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.
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.
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.
[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.
CAS: 124-64-1, 7732-18-5
Color: Green-Yellow or Pink
Flash Point: 96°C
Infrared Spectrum: Authentic
Packaging: Glass bottle
Specific Gravity: 1.34
SMILES: [Cl-].OC[P+](CO)(CO)CO
Molecular Weight (g/mol): 190.56
Formula Weight: 190.56
Percent Purity: 80.0 to 85.0%
Tetrakis(hydroxymethyl)phosphonium chloride can be analyzed by this reverse phase (RP) HPLC method with simple conditions.
The mobile phase contains an acetonitrile (MeCN), water, and phosphoric acid.
For Mass-Spec (MS) compatible applications the phosphoric acid needs to be replaced with formic acid.
Smaller 3 µm particles columns available for fast UPLC applications.
This liquid chromatography method is scalable and can be used for isolation impurities in preparative separation.
It also suitable for pharmacokinetics.
Formulation :80% in H2O
Physical State :Liquid
Storage :Store at room temperature
Catalogue Number: T298578
Chemical Name: Tetrakis(hydroxymethyl)phosphonium Chloride (ca. 80% in Water)
CAS Number: 124-64-1
Molecular Formula: C₄H₁₂ClO₄P
Molecular Weight:190.56
Category: Building Blocks; Miscellaneous;
Applications: Tetrakis(hydroxymethyl)phosphonium chloride (ca. 80% in Water) (cas# 124-64-1) is a useful research chemical.
1. Properties of Tetrakis(hydroxymethyl)phosphonium chloride:
Has Tetrakis(hydroxymethyl)phosphonium chlorides characteristic odor.
Non-flammable.
Has mild acid properties and are considered corrosive.
Easily biodegradable and considered environmentally friendly compound.
2. Applications of Tetrakis(hydroxymethyl)phosphonium chloride:
Tetrakis(hydroxymethyl)phosphonium chloride is a flame retardant for textiles.
Also a broad spectrum disinfectant and act as chemical intermiedates.
3. Specifications:
Purity: 82% – 85%
Active P 13% – 13.4%
Fe 10ppm max
Specific Gravity (25a ) 1.32 a 1.36
Viscosity(25a )MPAS 50MPA.S max
PH 3 — 5
4. Storage: Hermetically sealed
A novel and convenient method has been developed for the preparation of tris(hydroxy-methyl) phosphine oxide (THPO) from tetrakis (hydroxymethyl) phosphonium chloride (THPC).
The method consists essentially of oxidative deformylation of THPC with lead carbonate in n-propyl alcohol.
The reaction is facilitated by azeotropic distillation of di-n-propylformal and n -propyl alcohol.
The reaction of THPC with lead carbonate as well as with lead oxide has been studied in detail in aqueous solution and in n-propyl alcohol.
The reaction proceeds via the initial formation of tetrakis(hydroxymethyl) phosphonium hydroxide (THPOH) followed by deformylation to tris (hydroxymethyl) phosphine (THP).
THP then undergoes oxidation by air as well as by lead carbonate or oxide to THPO.
If air is bubbled through the mixture at elevated temperatures, atmospheric oxidation predominates with little or no oxidation by the lead compound.
Depending upon the reaction conditions, a phosphonium hydroxide, a phosphine, or a phosphine oxide are products of the reaction of tetrakis(hydoxymethyl) phosphonium chloride with lead carbonate or oxide.
Other tetrakis(hydroxymethyl)phosphium salts are:
Acetate
Acetate-phosphate
Bromide
6-Carboxycellulose salt
Cellulose carboxymethyl ether salt
Formate
Hydroxybutanedioate
2-Hydroxyproprionate
Iodide
1-Naphthalenesulfonate
2-Naphthalenesulfonate
Oxalate
Phospate
Tetraphenylborate-tetraacetate
para-Toluenesulfonate
Synonym:
tetrakis hydroxymethyl phosphonium chloride
thpc
pyroset tkc
retardol c
tetramethylolphosphonium chloride
tetrakis hydroxymethyl phosphanium chloride
unii-58wb2xcf8i
proban cc
tetrakis hydroxymethyl phosphochloride
ccris 317
124-64-1 [RN]
204-707-7 [EINECS]
3631669
Chlorure de tétrakis(hydroxyméthyl)phosphonium [French] [ACD/IUPAC Name]
MFCD00031687 [MDL number]
Phosphonium, tetrakis(hydroxymethyl)-, chloride (1:1) [ACD/Index Name]
TA2450000
Tetra(hydroxymethyl)phosphonium chloride
Tetrakis(hydroxymethyl)phosphonium chloride [ACD/IUPAC Name]
Tetrakis(hydroxymethyl)phosphoniumchlorid [German] [ACD/IUPAC Name]
THPC solution
[tris(hydroxymethyl)phosphino]methan-1-ol, chloride
2245-60-5 [RN]
52221-67-7 [RN]
55566-30-8 [RN]
7580-37-2 [RN]
80% in Water
EINECS 204-707-7
Phosphonium, chloro-tetrakis(hydroxymethyl)-
phosphonium, tetrakis(hydroxymethyl)-, chloride
Proban CC
Pyroset TKC
Retardol C
Tetra(hydroxymethyl)phosphoniumchloride
Tetrahydroxymethylphosphonium chloride
TETRAKIS(HYDROXYMETHYL) PHOSPHONIUM CHLORIDE
Tetrakis(Hydroxymethyl) Posphonium Chloride
Tetrakis-(hydroxymethyl)fosfoniumchlorid [Czech]
Tetrakis-(hydroxymethyl)fosfoniumchlorid [Czech]
tetrakis(hydroxymethyl)phosphanium chloride
Tetrakis(hydroxymethyl)phosphochloride
tetrakis(hydroxymethyl)-phosphonium chloride
tetrakis-(hydroxymethyl)-phosphonium chloride
Tetrakis(hydroxymethyl)phosphonium Chloride (ca. 80% in Water)
Tetrakis(hydroxymethyl)phosphonium chloride solution
Tetrakis(hydroxymethyl)phosphonium chloride;THPC
Tetrakis(hydroxymethyl)phosphonium phosphate
tetrakis(hydroxymethyl)phosphoniumchloride
tetrakishydroxymethyl phosphonium chloride
tetrakishydroxymethylphosphonium chloride
TETRAMETHYLOLPHOSPHONIUM CHLORIDE
THPC
WLN: Q1P1Q1Q1Q & G
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
Phosphonium, tetrakis(hydroxymethyl)-, chloride (1:1)
58WB2XCF8I
tetrakis(hydroxymethyl)phosphanium;chloride
Retardol C
Proban CC
CCRIS 317
HSDB 2923
EINECS 204-707-7
Tetrahydroxymethylphosphonium chloride
NSC 30698
Tetrakis(hydroxymethyl)phosphonium Chloride (ca. 80% in Water)
AI3-22268
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
MFCD00031687
NSC-30698
AKOS015918384
Tetra(hydroxymethyl)phosphoniumchloride
NCGC00164162-01
NCGC00255382-01
CAS-124-64-1
DB-007909
tetrakis-(hydroxymethyl)phosphonium chloride
FT-0631726
Phosphonium, chloro-tetrakis(hydroxymethyl)-
T0607
EN300-19000
Q7706566