Stability of Sodium Tetraphenylboron Solutions

Cooper, Stancil S.

doi:10.1021/ac60123a035

Cited by 22 publications

(7 citation statements)

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“…Appearance of turbidity in the stock solution may be delayed by neutralizing it to pH 7 with sodium hydroxide ( 19), or storing it in a refrigerator when not in use (8). Cooper (3) has made a more comprehensive study of the stability of sodium tetraphenylborate solutions.…”

Section: Resultsmentioning

confidence: 99%

Tetraphenylborate Spot Test for Detection of Amines and Their Salts

Crane¹

1958

Anal. Chem.

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Section: Resultsmentioning

confidence: 99%

Tetraphenylborate Spot Test for Detection of Amines and Their Salts

Crane¹

1958

Anal. Chem.

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“…The order of dependence on total copper increases in the order of 3PB ~ 2PB < 1PB NaTPB. We discussed kinetic rate expressions for reaction pathways involving both a redox process with hydroxide and copper reactants (reactions [4][5], and dephenylation by reduced cuprous ion involving a phenylated copper organometallic intermediate (reactions [6][7]. Increased decomposition rates in the presence of oxygen for 3PB, 2PB and 1PB suggest that oxidation of copper (i.e., the sequence of reactions 4-5) may play a significant role in governing the rate of decomposition.…”

Section: Discussionmentioning

confidence: 99%

“…During commissioning of the process in 1995, all excess NaTPB unexpectedly decomposed [5,6]. The literature indicates that NaTPB solutions hydrolyze unless stabilized by sodium hydroxide [7]. Previous experience with aqueous NaTPB solutions indicated that even in the presence of sodium hydroxide, NaTPB decomposes in the presence of soluble copper [8].…”

Section: Introductionmentioning

confidence: 99%

Copper-catalyzed sodium tetraphenylborate, triphenylborane, diphenylborinic acid and phenylboronic acid decomposition kinetic studies in aqueous alkaline solutions

Crawford

Barnes

Peterson

et al. 1999

Journal of Organometallic Chemistry

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This work studied the kinetics of copper-catalyzed decomposition of tetraphenylborate, triphenylborane, diphenylborinic acid and phenylboronic acid (NaTPB, 3PB, 2PB and 1PB, respectively) in aqueous alkaline solution over the temperature range of 25 to 70 °C. The statistically designed test matrices added copper sulfate to maximum concentrations of 10 mg/L. The relative rates of decomposition increase in the order of NaTPB < 1PB ~ 3PB < 2PB. Dependence of decomposition on the amount of added copper increases in the order of 3PB ~ 2PB < 1PB ~ NaTPB. Activation energies ranged from 82 to 143 kJ/mole over the temperature range studied. Final decomposition products predominately involved benzene and phenol. All 3PB, 2PB and 1PB intermediate phenylborate species proved relatively stable (< 8% decomposition ) thermal hydrolysis of the phenylborate species occurs at 55 to 70° C in alkaline (0.6-2.3 M OH -, 2-4.7 M Na + ) solution with no added copper. The experiments suggest an important role for oxygen in copper-catalyzed phenylborate decomposition. NaTPB decomposes promptly under anoxic conditions while 3PB, 2PB and 1PB decompose faster in aerobic solutions. Benzene and phenol form as the predominant end-products from alkaline copper catalysis in static systems sealed under air. Both 2PB and 1PB decompose with near equal rates and quantitatively produce phenol under flowing air-purge conditions at 25 to 60 °C. Mechanisms for copper-catalyzed phenylborate decomposition likely involve a redox process giving loss of a phenyl group from the phenylborate with reduction of cupric ion, or dephenylation by reduced cuprous ion involving a phenylated copper intermediate.

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“…Before each titration the electrode was briefly brought to red heat on a bunsen lamp. It was then soaked for 3 min in a magnetically stirred 3% w/v sodium tetraphenylborate solution previously stabilized (Cooper 1957) and freshly prepared every two weeks, finally it was rinsed with distilled water. This pretreatment replaced that described in our earlier report (Pinzauti & La Porta 1977).…”

Section: Itaiymentioning

confidence: 99%