Phosphonium, tetrakis chloride

Tetrakis(hydroxymethyl)phosphonium Salts. The reaction of formaldehyde (qv) and phosphine in aqueous hydrochloric or sulfuric acid yields tetrakis-(hydroxymethyl)phosphonium chloride [124-62-1/, Albright Wilson s Retardol C, or the sulfate [55566-30-8] (Retardol S), (C4H 2C4P)2SO [55566-30-8]. 

The salt ia this case is tetrakis(hydroxymethyl)phosphonium chloride [124-64-1]. The corresponding sulfate salt [55566-30-8] is also produced commercially as are urea-containing formulations of both salts. The latter formulations are actually used to flame retard the textiles (see Flame retardants FOR textiles). 

Biocides. Two phosphine derivatives are ia commercial use as biocides. These are tetrakis(hydroxymethyl)phosphonium sulfate [55566-30-8] and tributyl(tetradecyl)phosphonium chloride [8741-28-8]. These compounds are sold by Albright and Wilson Ltd. and EMC, respectively. The preparation... 

Flame Retardants. The amount of research expended to develop flame-retardant (FR) finishes for cotton and other fabrics has been extremely large in comparison to the total amount of fabrics finished to be flame retardant. The extent of this work can be seen in various reviews (146—148). In the early 1960s, a substantial market for FR children s sleepwear appeared to be developing, and substantial production of fabric occurred. In the case of cotton, the finish was based on tetrakis(hydroxymethyl)phosphonium chloride (THPC) or the corresponding sulfate (THPS). This chemical was partly neutralized to THPOH, padded on fabric, dried under controlled conditions, and ammoniated. The finish was subsequently oxidized, yielding a product that passed the test for FR performance. This process is widely preferred to the THPOH—NH process. 

Tetrakis(hydroxymethyl)phosphonium chloride [124-64-1] AcOH and dried at 100° in a vacuum. An 80% w/v aqueous solution has d 7955]. 

The tetrakis(hydroxymethyl)phosphonium chloride so formed is the major ingredient with urea-formaldehyde or melamine-formaldehyde resins for the permanent flame-proofing of cotton cloth. 

A development reported recently [519] involves reduction of the cystine disulphide bonds in wool with either thioglycolic acid or tetrakis(hydroxymethyl)phosphonium chloride to form thiol groups, followed by crosslinking with bifunctional reactive dyes. This gave improved insect resistance but had adverse effects on physical properties such as strength, shrinkage and stiffness, thus limiting the potential of the process for commercial use. 

The main method for obtaining these heterocycles is the interaction of amines with oxymethylphosphines. Frank and Drake (72JOC2752 77JOC4040) isolated 5-aminomethyl-l,3-diphenyl-l,3,5-diazaphosphori-nane (39) by treating tris(oxymethyl) phosphine (40) or tetrakis(oxy-methyl)phosphonium chloride (38) with aniline. The reaction with p-toluidine proceeds in a similar manner [Eq. (24)] (83IZV1379). 

Thorpe reaction org chem The reaction by which, in presence of lithium amides, a,(rt-dinitriles undergo base-catalyzed condensation to cyclic iminonitriles, which can be hydrolyzed and decarboxylated to cyclic ketones. thorp re,ak-shan TMPC See tetrakis(hydroxymethyl)phosphonium chloride, thulia See thulium oxide. thu-le-a ... 

Little attention was paid to these reactions until 1921 when Hoffman 174-176) prepared tetrakis(hydroxymethyl)phosphonium chloride by passing phosphine into a warm, aqueous hydrochloric acid solution of formaldehyde. The product was obtained in the form of colourless crystals by evaporation of the reaction solution. 

Chem. Abstr. Name. Phosphonium, tetrakis(hydroxymethyl)-, chloride... 

Tetrakis(hydroxymethyl)phosphonium chloride was tested for carcinogenicity by oral administration in one strain of mice and one strain of rats. No dose-related increase in the incidence of any tumour was observed however, in male rats receiving the low dose, there was an increased incidence of mononuclear-cell leukaemia. Tetrakis(hydroxymethyl)-phosphonium chloride did not show significant promoting activity in a two-stage skin carcinogenicity test in mice. 

Tetrakis(hydroxymethyl)phosphonium chloride can be absorbed through the skin (Ulsamer et al., 1980). 

Tetrakis(hydroxymethyl)phosphonium chloride and sulfate salts were not mutagenic to bacteria in either the presence or absence of an exogenous metabolic system. In single studies, the sulfate salt induced mutations in mouse lymphoma L5178Y cells in vitro at the tk locus and, in mouse bone marrow in vivo, it caused a marginal increase in the frequency of chromosomal aberrations, but did not induce micronuclei (lARC, 1990). 

Tetrakis(hydroxymethyl)phosphonium chloride was not mutagenic to bacteria in... 

A pH-controlled process for obtaining high-purity quaternary phosphonium chlorides has been patented21. An electrolytic process may also be used with the same aim in the case of phosphonium hydroxides22. Titration of water-soluble tetrakis hydroxymethyl-phosphonium chloride (1) with iodine in the presence of weak bases can be used for the analysis of this compound23. 

To an open 800-mL beaker containing 124 g of ice and 238 g (1.25 mol) of THPC, tetrakis(hydroxymethyl)phosphonium chloride, a solution of 63.9 g NaOH (50% w/w) is slowly added while manually stirring. After the resulting clear, colorless solution warms to room temperature, 450 g of formaldehyde (40%, 6.25 mol) is added. Then 140 g (1.00 mol) of hexamethylenetetraamine7 is dissolved in the solution, which is subsequently allowed to stand overnight. The solution is then transferred to a large evaporating dish and placed under a hood or draft of air for ease of evaporation. It is allowed to stand until the solution becomes approximately... 

The CPSC staff performed quantitative risk assessments on various flame-retardants for both upholstered residential furniture fabrics and foam.89 CPSC addresses chemical hazards under the Federal Hazardous Substances Act (FHSA), which is risk based. For fabrics, five flame-retardants were evaluated, that include antimony trioxide, deca-BDE, HBCD, phosphonic acid, (3- [hydroxymethyl]amino)-3-oxopropyl)-, dimethyl ester (PA), and tetrakis (hydroxymethyl) phosphonium chloride (THPC). These flame-retardants were selected for study because they are used to comply with the U.K. upholstered furniture flammability standard (except THPC) and fabric samples were available for testing. The staff concluded in 2006 that deca-BDE, HBCD, and PA would not present a hazard to consumers and that additional data would be needed to assess antimony trioxide and THPC. 

Other most successful durable treatment is based on tetrakis (hydroxymethyl) phosphonium derivatives. Very well-known brand marketed as Proban CC (Rhodia, previously Albright Wilson) involves padding of tetrakis (hydroxymethyl) phosphonium chloride (THPC) urea solution onto the cotton fabric, curing with ammonia in a specially designed reactor to generate a highly cross-linked three-dimensional polymer network. The fabric is then treated with hydrogen peroxide, which converts P3+ to the P5+ state. The reactions are shown in Scheme 24.2. Other similar commercial product is Thor s Aflammit P. In literature many combinations of tetrakis (hydroxymethyl) phosphonium derivatives with other salts have been reported,50 but the most successful so far has been the THPC-urea-NH3 system discussed earlier. 

Also phosphorus- and nitrogen-containing polyols are shown to be effective in flame retardancy of PU foams24 such as polyols based on phosphonic acid ester or obtained by partial or full substitution of methylol groups of tetrakis(hydroxymethyl)phosphonium chloride with amine several examples of such polyols were reported by Levchik and Weil.15 Rigid PU foam modified with these polyols showed improved oxygen index values moreover better results were achieved with higher functionality polyols. 

Gold nanorods were prepared by the photochemical procedure of Kim et al. [6]. Gold nanocrystals with an average diameter of 2.5 nm were obtained by the reduction of chlo-roaurate ion (0.55 ml of 25 mM aqueous solution) by partially hydrolyzed tetrakis (hydroxymethyl) phosphonium chloride (THPC) [7], CdSe nanocrystals were prepared by the solvothermal procedure starting with cadmium stearate, selenium and tetralin in toluene [8]. SWNTs prepared by the electric arc method with a Y2O3 + Ni catalyst, were purified by acid and hydrogen treatments [9]. 

GroBere Aufmerksamkeit fand die Reaktion jedoch erst, als 1921 Hoffman 174-176) durch Einleiten von Phosphin in eine warme, waBrige, salzsaure Losung von Formaldehyd das Tetrakis(hydroxymethyl)-phosphonium-chlorid herstellte, das beim Eindampfen der Reaktions-losung in Form farbloser Kristalle zuriickbleibt. 

Proban A process for rendering textiles flame-retardant by treatment with tetrakis hydroxymethyl phosphonium chloride (THPC). Invented at the U.S. Regional Research Laboratory in New Orleans, LA, in the early 1950s. Commercialized in 1955 under the trade name Proban by Proban Ltd., a joint venture between the Bradford Dyers Association and Albright Wilson. Now offered by Rhodia. 

Although inorganic salts can provide excellent flame-retardant properties for cellulose, reasonable laundering durability must be incorporated into any finish destined for apparel use. The most successful durable flame retardants for cellulose are based on phosphorous- and nitrogen-containing chemical systems that can react with the fibre or form crosslinked structures on the fibre. The key ingredient of one of these finishes is tetrakis(hydroxymethyl)phosphonium chloride (THPC), made from phosphine, formaldehyde and hydrochloric acid (Fig. 8.11). THPC reacts with urea to form an insoluble structure on cellulose in a pad-dry-cure process (Fig. 8.12). 

Because these fire-retardant salts are water-soluble and subject to leaching, several new methods have been developed which provide a water-resistant or permanent treatment for cotton fabrics and cellu-losic materials. Perkin developed a process involving successive treatment with sodium stannate and ammonium sulfate, which precipitates stannic oxide in the cellulose libers. Antimony oxide in combination with vinyl chloride or other chlorinated polymers has also been found effective. A more recent approach to this problem involves application of fire-retardant resin-forming or cross-linking compounds. " These include materials and methods based on the copolymerization of tetrakis(hydroxymethyl)phosphonium chloride and methylol — melamine, the reaction of bromoform and triallyl phosphate to form a cross-linked polymer, and the cross-linking reaction of tris(l-aziridinyl)phosphine oxide with cellulose, or its copolymerization with tetrakis(hydroxymethyl)phosphonium chloride and other materials. ... 

A variety of compounds capable of rupturing disulfide bonds have been shown to accelerate setting. Sulfite mixed with ninhydrin (Speakman and Speakman, 1956), tetrakis(hydroxymethyl)phosphonium chloride (Bajpai et al., 1960,1961 Zahn and Vassiliadis, 1962 Jenkins and Wolfram, 1963), thiourea dioxide (Bajpai and Whewell, 1961), and peracetic acid (Jenkins and Wolfram, 1964) are examples. 

C4H10O3 2-methoxy-1,3-propanediol 761-06-8 505.15 44.379 1,2 4048 C4H12CI04P tetrakis(hydroxymethyl)phosphonium chloride 124-64-1 390.85 33.504 1,2... 

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