Synthesis of tris(aminomethyl)phosphine oxide and its carbon dioxide adduct from tetrakis(hydroxymethyl)phosphonium salts via their methyl carbamate derivatives

Frank, Arlen W.

doi:10.1139/v81-005

Cited by 19 publications

(7 citation statements)

References 12 publications

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“…[33] A mixture of 75% aqueous 1 (135.4 g, 0.25 mol) and methyl carbamate (150.1 g, 2.00 mol) was heated to reflux with constant stirring, and held at 106-108°C for 2 h, allowed to cool, stripped of water under reduced pressure giving 218.7 g (101.5%) of 2 as an almost colorless tacky glass.…”

Section: Synthesis Of Octakis(n-carbomethoxylaminomethyl) Diphosphonimentioning

confidence: 99%

“…[33] A solution of 2 (200.0 g, 0.23 mol) in distilled water (300 mL) was purged with argon, and treated with concentrated ammonium hydroxide (100 mL) over 15 min at 20-25°C. Solids started to separate after a few minutes, and after 2 h another 150 mL of distilled water was added to facilitate stirring.…”

Section: Synthesis Of Tris(n-carbomethoxylaminomethyl) Phosphinementioning

confidence: 99%

“…Tris (N-carbomethoxyl-aminomethyl)phosphine and its oxide were successfully synthesized from THPS by Frank. [33] These compounds contain methyl carbamate functional groups, which can produce isocyanates through thermal decomposition method. This process is a promising ecologically safe method of obtaining isocyanates without using the toxic phosgene.…”

Section: Introductionmentioning

confidence: 99%

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Phosphorus-containing polymers from THPS.I. Design, synthesis, and characterization of novel monomer and polyureas

Tan

Zhang

Guo³

et al. 2014

Designed Monomers and Polymers

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A new phosphorus-containing dicarbamates, di(N-carbomethoxylaminomethyl)benzyl phosphine oxide was first synthesized from tetrakis(hydroxymethyl)phosphonium sulfate (THPS) via five step reactions (Scheme 1), and its structure was proved by FTIR, ( 1 H, 13 C, and 31 P) NMR, and MS. A series of thermally stable phosphorus-containing polyureas were synthesized via trans-ureation polycondensation of the new monomer with aliphatic diamines, including poly(propylene glycol) bis(2-aminopropyl ether), respectively. All of the above polyureas were fully characterized by inherent viscosity, GPC, solubility tests, and thermogravimetric analysis. The thermal gravimetric analysis results showed that the initial breakdown temperature of all phosphorus-containing polyureas was observed at above 265°C while complete weight loss occurred in the region of 406-465°C, which shows all polyureas have good thermal stability. GPC results showed that the maximum number-average molecular weight of the synthesized polyureas reached 59,100 g mol. The solubility tests results demonstrated that incorporating the ether moieties into the polymer main chain can enhance the solubility of polyureas in organic solvents.

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Section: Synthesis Of Octakis(n-carbomethoxylaminomethyl) Diphosphonimentioning

confidence: 99%

Section: Synthesis Of Tris(n-carbomethoxylaminomethyl) Phosphinementioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Phosphorus-containing polymers from THPS.I. Design, synthesis, and characterization of novel monomer and polyureas

Tan

Zhang

Guo³

et al. 2014

Designed Monomers and Polymers

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“…The best bases are those that are capable of reacting with formaldehyde, such as ammonium hydroxide, morpholine, and sodium sulfite [40,50].…”

Section: Reactionsmentioning

confidence: 99%

Chemistry of Hydroxymethyl Phosphorus Compounds

Frank

Daigle

Vail

1982

Textile Research Journal

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The chemistry of the hydroxymethyl phosphonium salts and their derivatives is reviewed, with major emphasis on reactions in which the quaternary structure of the phosphonium salts is preserved.The subject matter covered in this review is restricted to phosphonium salts that are of interest to textile chemists as flame retardants for cotton. Formally, these compounds are derived from tetramethylphosphonium chloride, Me4PCl, or its equivalent (CH3)4P'Cl-, by substituting a single OR, NR2, or halogen substituent, where R = H, alkyl, aryl, acyl, alkoxycarbonyl, or aminocarbonyl group or combination thereof, for a hydrogen atom in each and every methyl group, or by substituting another anion for the chloride anion. There are many phosphonium salts that do not fall into this classification. For these, the reader should consult a textbook on organo-4 Names of companies or commercial products are given solely for the purpose of providing specific information. Their mention does not imply recommendation or endorsement by the U.S. Department of Agriculture over others not mentioned.

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“…However, only few T P O 's containing one or more primary amino groups in their mole cules are known. Studies on such compounds are limited [6][7][8][9][10][11][12]. Because of the high activity of amino groups these compounds can be used as phosphorylation agents for polymers, as well in synthesis of new organophosphorus compounds.…”

Section: Introductionmentioning

confidence: 99%