Propane-1,2,3-triphosphonic acid and butane-1,2,3,4-tetraphosphonic acid

Cilley, W. A.; Nicholson, D. Allan; Campbell, D. S.

doi:10.1021/ja00709a045

Cited by 6 publications

(2 citation statements)

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“…Synthesis. Synthesis of molecules C3 and C4 was performed based on previously described literature procedures, 32 as shown in Figure 2. Both C3 (white powder) and C4 (light amber-colored resin) are water-soluble and can exist as highly viscous oils, which slowly crystallize over extended periods of time.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…Materials consisting of silica-supported phosphonic acids are described as follows: PA/SiO 2 -X% , where PA represents the phosphonic acid (i.e., either C3 , C4 CX8 , or PVPA ) and X is the mass percentage of PA in the resulting solid material. C3 and C4 are prepared as shown in Figure , and this synthesis is adapted from that previously published and patented by Cilley, Nicholson, and Campbell. − …”

Section: Methodsmentioning

confidence: 99%

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Silica-Supported Phosphonic Acids as Thermally and Oxidatively Stable Organic Acid Sites

et al. 2016

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Organic–inorganic materials consisting of organophosphonic-acid-supported-on-silica materials C3/SiO2 and C4/SiO2 are described, where C3 is propane-1,2,3-triphosphonic acid and C4 is butane-1,2,3,4-tetraphosphonic acid. Solid-state structures of both of these phosphonic acids are analyzed using single-crystal X-ray diffraction, and these data reveal extensive intermolecular hydrogen bonding and no intramolecular hydrogen bonds. Thermogravimetric analysis/mass spectroscopy (TGA/MS) data show a lack of combustion for these materials in air at temperatures below 400 °C, and only release of water corresponding to reversible organophosphonic acid condensation below 150 °C. A comparative series of silica-supported materials were synthesized, consisting of organophosphonic acid CX8, which represents a calixarene macrocycle that is decorated with a high density of organophosphonic-acid substituents on both the lower and upper rim, as well as polyvinylphosphoric acid (PVPA). Material CX8/SiO2 possesses a significantly lower thermal stability and lower combustion temperature of 300 °C in air, whereas PVPA demonstrates comparable thermal stability as observed with C3 and C4. TGA coupled with base-probe titration was used to determine the Brønsted acid site density of all silica-supported phosphonic acids at various coverages and temperatures. Material C4/SiO 2 -37% (corresponding to 37% (by mass) loading and half-monolayer coverage on silica) exhibited the highest Brønsted acid-site density of all materials, corresponding to 0.84 mmol/g at 150 °C, and 0.62 mmol/g at 300 °C. All supported phosphonic acids treated with pyridine at room temperature were strong enough acids to protonate pyridine at room temperature as exhibited by a distinct pyridinium cation band in the infrared spectrum; however, in contrast to much stronger acid sites in silica-supported phosphoric acid materials, almost all adsorbed pyridine was lost by 150 °C. Use of a stronger base for acid-site titration consisting of diisopropylamine (DIPA) demonstrates acid sites in all materials up to 300 °C, at which temperature the acid site was too weak to adsorb DIPA. Thus, these oxidatively stable materials are deemed to be useful in applications requiring weak Brønsted acid sites, while exhibiting high-temperature oxidative stability up to 400 °C.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Silica-Supported Phosphonic Acids as Thermally and Oxidatively Stable Organic Acid Sites

et al. 2016

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The Synthesis of Phosphonic and Phosphinic Acids and their Derivatives: Non‐Functionalized Acids

Edmundson¹

2009

Patai's Chemistry of Functional Groups

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Introduction The Formation of P  C ( sp 3 ) Bonds. Syntheses of Alkyl, Cycloalkyl and Aralkyl Phosphonic and Phosphinic Acids The Formation of P  C ( sp 2 ) Bonds. Syntheses of Alkenyl and Alkadienyl Phosphonic and Phosphinic Acids The Formation of P  C ( sp ) Bonds. Syntheses of Alkynyl Phosphonic and Phosphinic Acids The Formation of P  C (Aromatic) Bonds. Syntheses of Aryl Phosphonic and Phosphinic Acids Syntheses of Phosphonic and Phosphinic Acids by Modification Procedures

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ChemInform Abstract: PROPAN‐1,2,3‐TRIPHOSPHONSAEURE UND BUTAN‐1,2,3,4‐TETRAPHOSPHONSAEURE

Cilley¹,

Nicholson²,

Campbell³

1970

Chemischer Informationsdienst. Organische Chemie

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Propane-1,2,3-triphosphonic acid and butane-1,2,3,4-tetraphosphonic acid

Cited by 6 publications

References 1 publication

Silica-Supported Phosphonic Acids as Thermally and Oxidatively Stable Organic Acid Sites

Silica-Supported Phosphonic Acids as Thermally and Oxidatively Stable Organic Acid Sites

The Synthesis of Phosphonic and Phosphinic Acids and their Derivatives: Non‐Functionalized Acids

ChemInform Abstract: PROPAN‐1,2,3‐TRIPHOSPHONSAEURE UND BUTAN‐1,2,3,4‐TETRAPHOSPHONSAEURE

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