Counter-ion and solvent effects in electrospray ionization of solutions of alkali metal and quaternary ammonium salts

2013 ◽  
Vol 354-355 ◽  
pp. 219-228 ◽  
Author(s):  
Konrad Koszinowski ◽  
Friederike Lissy
2021 ◽  
Author(s):  
Roel Kleijwegt ◽  
Wyatt Winkenwerder ◽  
Wim Baan ◽  
John van der Schaaf

<div>Surfactants such as quaternary ammonium salts (QAS) have been in increasing demand, for emerging new applications. Recent attempts at process intensification of</div><div>their production, have disclosed the need for a better understanding of QAS thermal stability. This work aims to determine degradation kinetics of various QASs, and the</div><div>associated solvent effects. Degradation kinetics of four methyl carbonate QASs were determined in various</div><div>polar solvents in stainless steel batch autoclaves. <sup>1</sup>H NMR spectrometry was employed for online analysis of the reaction mixtures. The kinetic parameters were then used</div><div>to compare the thermal stability of the four compounds in the polar solvents. Water showed not degradation, and methanol (MeOH) was the solvent that provided the</div><div>second-best stability. Water-MeOH mixtures may provide an overall optimum. More, and longer long-chain substituents increased the degradation rate. Thermogravimetric Analysis was used to obtain the thermal stability in a solid-</div><div>state, i.e. solventless environment. Isoconversional analysis showed that no reliable kinetic parameters could be determined. Nevertheless, the data did allow for a compar-</div><div>ison of the thermal stability of 14 different QASs. Furthermore, the relative instability of the compounds in solid-state demonstrated the challenges of solventless QAS production.</div>


2018 ◽  
Vol 21 ◽  
pp. 160-170 ◽  
Author(s):  
Bahar Darsazan ◽  
Alireza Shafaati ◽  
Afshin Zarghi ◽  
Seyed Alireza Mortazavi

Purpose: Adefovir is an antiviral drug that exhibits high hydrophilic properties and negligible bioavailability (less than 12%). It is only applied in the form of the ester prodrug adefovir dipivoxil (ADV). The oral bioavailability of ADV is limited (32% to 45%) by its low permeability (Class 3) and biological conversion of the prodrug to adefovir. Ion-pair formation is considered as an alternative approach to a covalent prodrug (ADV) to enhance intestinal permeation of adefovir. Methods: The effect of various counter-ions (anionic, cationic and two quaternary ammonium salts) on the lipophilicity of adefovir was investigated by means of the n-octanol/buffer partitioning system, an in vitro transport model (PAMPA) and a biological membrane (everted gut sac). Results: Quaternary ammonium salts, cetylpyridinium chloride (CPC) and cetrimide enhanced the lipophilicity of adefovir 136- and 87-fold, respectively. The apparent permeability of adefovir in combination with CPC (counter-ion) was 2.5-fold greater than ADV permeability in the PAMPA model. The apparent permeability of adefovir-CPC (counter-ion) was 1.3-fold greater than that of adefovir dipivoxil permeability in a biologic membrane (everted gut sac). Conclusion: These results suggest that the adefovir-CPC ion-paired system has potential for improving the permeation of adefovir across the intestinal membrane. This article is open to POST-PUBLICATION REVIEW. Registered readers (see “For Readers”) may comment by clicking on ABSTRACT on the issue’s contents page.


2021 ◽  
Author(s):  
Roel Kleijwegt ◽  
Wyatt Winkenwerder ◽  
Wim Baan ◽  
John van der Schaaf

<div>Surfactants such as quaternary ammonium salts (QAS) have been in increasing demand, for emerging new applications. Recent attempts at process intensification of</div><div>their production, have disclosed the need for a better understanding of QAS thermal stability. This work aims to determine degradation kinetics of various QASs, and the</div><div>associated solvent effects. Degradation kinetics of four methyl carbonate QASs were determined in various</div><div>polar solvents in stainless steel batch autoclaves. <sup>1</sup>H NMR spectrometry was employed for online analysis of the reaction mixtures. The kinetic parameters were then used</div><div>to compare the thermal stability of the four compounds in the polar solvents. Water showed not degradation, and methanol (MeOH) was the solvent that provided the</div><div>second-best stability. Water-MeOH mixtures may provide an overall optimum. More, and longer long-chain substituents increased the degradation rate. Thermogravimetric Analysis was used to obtain the thermal stability in a solid-</div><div>state, i.e. solventless environment. Isoconversional analysis showed that no reliable kinetic parameters could be determined. Nevertheless, the data did allow for a compar-</div><div>ison of the thermal stability of 14 different QASs. Furthermore, the relative instability of the compounds in solid-state demonstrated the challenges of solventless QAS production.</div>


Author(s):  
Tomasz K. Olszewski ◽  
Anna Brol

An effective protocol for quaternization of simple 1-aminoalkylphosphonic acids under basic conditions and using Me2SO4 as convenient alkylating agent is reported. In the course of reaction phosphonic acid quaternary ammonium...


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