Solid state and sub-cooled liquid vapour pressures of cyclic aliphatic dicarboxylic acids

Abstract. Knudsen Effusion Mass Spectrometry (KEMS) has been used to measure for the first time the solid state vapour pressures of a series of aliphatic cyclic dicarboxylic acids with increasing ring size. Additionally the atmospherically important compounds; cis-pinonic acid and levoglucosan were also measured. Differential Scanning Calorimetry (DSC) was used to measure melting points, enthalpies and entropies of fusion, which were used to determine sub-cooled liquid vapour pressures for the compounds. The sub-cooled liquid vapour pressure of straight chain, branched and cyclic dicarboxylic acids was compared to a selection of estimation methods.

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Solid state and sub-cooled liquid vapour pressures of substituted dicarboxylic acids using Knudsen Effusion Mass Spectrometry (KEMS) and Differential Scanning Calorimetry

Atmospheric Chemistry and Physics ◽

10.5194/acp-10-4879-2010 ◽

2010 ◽

Vol 10 (10) ◽

pp. 4879-4892 ◽

Cited By ~ 63

Author(s):

A. M. Booth ◽

M. H. Barley ◽

D. O. Topping ◽

G. McFiggans ◽

A. Garforth ◽

...

Keyword(s):

Mass Spectrometry ◽

Differential Scanning Calorimetry ◽

Solid State ◽

Dicarboxylic Acids ◽

Estimation Methods ◽

Scanning Calorimetry ◽

Knudsen Effusion ◽

Oh Groups ◽

Knudsen Effusion Mass Spectrometry ◽

The Impact

Abstract. Solid state vapour pressures of a selection of atmospherically important substituted dicarboxylic acids have been measured using Knudsen Effusion Mass Spectrometry (KEMS) over a range of 20 K (298–318 K). Enthalpies of fusion and melting points obtained using Differential Scanning Calorimetry (DSC) were used to obtain sub-cooled liquid vapour pressures. They have been compared to estimation methods used on the E-AIM website. These methods are shown to poorly represent – OH groups in combination with COOH groups. Partitioning calculations have been performed to illustrate the impact of the different estimation methods on organic aerosol mass compared to the use of experimental data.

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Solid state and sub-cooled liquid vapour pressures of substituted dicarboxylic acids using Knudsen Effusion Mass Spectrometry (KEMS) and Differential Scanning Calorimetry

Atmospheric Chemistry and Physics Discussions ◽

10.5194/acpd-10-5717-2010 ◽

2010 ◽

Vol 10 (2) ◽

pp. 5717-5749

Author(s):

A. M. Booth ◽

M. H. Barley ◽

D. O. Topping ◽

G. McFiggans ◽

A. Garforth

Keyword(s):

Mass Spectrometry ◽

Differential Scanning Calorimetry ◽

Solid State ◽

Dicarboxylic Acids ◽

Estimation Methods ◽

Scanning Calorimetry ◽

Knudsen Effusion ◽

Oh Groups ◽

Knudsen Effusion Mass Spectrometry ◽

The Impact

Abstract. Solid state vapour pressures of a selection of substituted dicarboxylic acids have been measured using Knudsen Effusion Mass Spectrometry (KEMS). Enthalpies of fusion and melting points obtained using Differential Scanning Calorimetry (DSC) were used to obtain sub-cooled liquid vapour pressures. They have been compared to estimation methods used on the E-AIM website. These methods are shown to poorly represent -OH groups in combination with COOH groups. Partitioning calculations have been performed to illustrate the impact of the different estimation methods on organic aerosol mass compared to the use of experimental data.

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Measured Solid State and Sub-Cooled Liquid Vapour Pressures of Benzaldehydes Using Knudsen Effusion Mass Spectrometry

Atmosphere ◽

10.3390/atmos12030397 ◽

2021 ◽

Vol 12 (3) ◽

pp. 397

Author(s):

Petroc Shelley ◽

Thomas J. Bannan ◽

Stephen D. Worrall ◽

M. Rami Alfarra ◽

Carl J. Percival ◽

...

Keyword(s):

Mass Spectrometry ◽

Solid State ◽

Vapour Pressure ◽

Boiling Point ◽

Point Method ◽

Scanning Calorimetry ◽

Knudsen Effusion ◽

Pressure Method ◽

Liquid Saturation ◽

Knudsen Effusion Mass Spectrometry

Benzaldehydes are components of atmospheric aerosol that are poorly represented in current vapour pressure predictive techniques. In this study the solid state (PSsat) and sub-cooled liquid saturation vapour pressures (PLsat) were measured over a range of temperatures (298–328 K) for a chemically diverse group of benzaldehydes. The selected benzaldehydes allowed for the effects of varied geometric isomers and functionalities on saturation vapour pressure (Psat) to be probed. PSsat was measured using Knudsen effusion mass spectrometry (KEMS) and PLsat was obtained via a sub-cooled correction utilising experimental enthalpy of fusion and melting point values measured using differential scanning calorimetry (DSC). The strength of the hydrogen bond (H-bond) was the most important factor for determining PLsat when a H-bond was present and the polarisability of the compound was the most important factor when a H-bond was not present. Typically compounds capable of hydrogen bonding had PLsat 1 to 2 orders of magnitude lower than those that could not H-bond. The PLsat were compared to estimated values using three different predictive techniques (Nannoolal et al. vapour pressure method, Myrdal and Yalkowsky method, and SIMPOL). The Nannoolal et al. vapour pressure method and the Myrdal and Yalkowsky method require the use of a boiling point method to predict Psat. For the compounds in this study the Nannoolal et al. boiling point method showed the best performance. All three predictive techniques showed less than an order of magnitude error in PLsat on average, however more significant errors were within these methods. Such errors will have important implications for studies trying to ascertain the role of these compounds on aerosol growth and human health impacts. SIMPOL predicted PLsat the closest to the experimentally determined values.

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Measured solid state and subcooled liquid vapour pressures of nitroaromatics using Knudsen effusion mass spectrometry

Atmospheric Chemistry and Physics ◽

10.5194/acp-20-8293-2020 ◽

2020 ◽

Vol 20 (14) ◽

pp. 8293-8314

Author(s):

Petroc D. Shelley ◽

Thomas J. Bannan ◽

Stephen D. Worrall ◽

M. Rami Alfarra ◽

Ulrich K. Krieger ◽

...

Keyword(s):

Mass Spectrometry ◽

Solid State ◽

Vapour Pressure ◽

Scanning Calorimetry ◽

Subcooled Liquid ◽

Knudsen Effusion ◽

Liquid Saturation ◽

Knudsen Effusion Mass Spectrometry ◽

Saturation Vapour Pressure ◽

Selection Of Species

Abstract. Knudsen effusion mass spectrometry (KEMS) was used to measure the solid state saturation vapour pressure (PSsat) of a range of atmospherically relevant nitroaromatic compounds over the temperature range from 298 to 328 K. The selection of species analysed contained a range of geometric isomers and differing functionalities, allowing for the impacts of these factors on saturation vapour pressure (Psat) to be probed. Three subsets of nitroaromatics were investigated: nitrophenols, nitrobenzaldehydes and nitrobenzoic acids. The PSsat values were converted to subcooled liquid saturation vapour pressure (PLsat) values using experimental enthalpy of fusion and melting point values measured using differential scanning calorimetry (DSC). The PLsat values were compared to those estimated by predictive techniques and, with a few exceptions, were found to be up to 7 orders of magnitude lower. The large differences between the estimated PLsat and the experimental values can be attributed to the predictive techniques not containing parameters to adequately account for functional group positioning around an aromatic ring, or the interactions between said groups. When comparing the experimental PSsat of the measured compounds, the ability to hydrogen bond (H bond) and the strength of the H bond formed appear to have the strongest influence on the magnitude of the Psat, with steric effects and molecular weight also being major factors. Comparisons were made between the KEMS system and data from diffusion-controlled evaporation rates of single particles in an electrodynamic balance (EDB). The KEMS and the EDB showed good agreement with each other for the compounds investigated.

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Measured solid state and sub-cooled liquid vapour pressures of nitroaromatics using Knudsen effusion mass spectrometry

10.5194/acp-2020-75 ◽

2020 ◽

Author(s):

Petroc D. Shelley ◽

Thomas J. Bannan ◽

Stephen D. Worrall ◽

M. Rami Alfarra ◽

Ulrich K. Krieger ◽

...

Keyword(s):

Mass Spectrometry ◽

Solid State ◽

Vapour Pressure ◽

Scanning Calorimetry ◽

Knudsen Effusion ◽

Liquid Saturation ◽

Knudsen Effusion Mass Spectrometry ◽

Saturation Vapour Pressure ◽

Selection Of Species ◽

Major Factors

Abstract. Knudsen Effusion Mass Spectrometry (KEMS) was used to measure the solid state saturation vapour pressure (PSsat) of a range of atmospherically relevant nitroaromatic compounds over the temperature range from 298 to 328 K. The selection of species analysed contained a range of geometric isomers and differing functionalities, allowing for the impacts of these factors on saturation vapour pressure (Psat) to be probed. Three subsets of nitroaromatics were investigated, nitrophenols, nitrobenzaldehydes and nitrobenzoic acids. The PSsat were converted to sub-cooled liquid saturation vapour pressures (PLsat) using experimental enthalpy of fusion and melting point values measured using differential scanning calorimetry (DSC). The PLsat were compared to those estimated by predictive techniques and, with a few exceptions, were found to be up to 7 orders of magnitude lower. The large differences between the estimated PLsat and the experimental can be attributed to the predictive techniques not containing parameters to adequately account for functional group positioning around an aromatic ring, or the interactions between said groups. When comparing the experimental PSsat of the measured compounds the ability to hydrogen bond (H-Bond), and the strength of a H-bond formed appear to have the strongest influence on the magnitude of the Psat with steric effects and molecular weight also being major factors. Comparisons were made between the KEMS system and data from diffusion-controlled evaporation rates of single particles in an electrodynamic balance (EDB). The KEMS and the EDB showed good agreement with each other for the compounds investigated.

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Synergistic use of Knudsen effusion quadrupole mass spectrometry, solid-state galvanic cell and differential scanning calorimetry for thermodynamic studies on lithium aluminates

Journal of Solid State Chemistry ◽

10.1016/j.jssc.2008.03.003 ◽

2008 ◽

Vol 181 (6) ◽

pp. 1402-1412 ◽

Cited By ~ 11

Author(s):

S.K. Rakshit ◽

Y.P. Naik ◽

S.C. Parida ◽

Smruti Dash ◽

Ziley Singh ◽

...

Keyword(s):

Mass Spectrometry ◽

Differential Scanning Calorimetry ◽

Solid State ◽

Galvanic Cell ◽

Quadrupole Mass ◽

Scanning Calorimetry ◽

Knudsen Effusion ◽

Thermodynamic Studies ◽

Quadrupole Mass Spectrometry

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The Radiation Sterilization of Ertapenem Sodium in the Solid State

Molecules ◽

10.3390/molecules24162944 ◽

2019 ◽

Vol 24 (16) ◽

pp. 2944

Author(s):

Karolina Kilińska ◽

Judyta Cielecka-Piontek ◽

Robert Skibiński ◽

Daria Szymanowska ◽

Andrzej Miklaszewski ◽

...

Keyword(s):

Solid State ◽

Physicochemical Properties ◽

High Performance ◽

Degradation Products ◽

Radiation Sterilization ◽

Scanning Calorimetry ◽

Beam Radiation ◽

Promising Alternative ◽

Ft Ir ◽

First Time

For the first time, the influence of ionising radiation on the physicochemical properties of ertapenem in solid state was studied. During our studies, we evaluated the possibility of applying radiosterilization to obtain sterile ertapenem. Spectroscopic (Fourier Transform Infrared (FT-IR)), thermal (differential scanning calorimetry (DSC), chromatography (High-Performance Liquid Chromatography (HPLC) and HPLC-MS), and X-ray powder diffraction (XRPD) studies shown that irradiation of ertapenem with the 25 kGy, the dose required to achieve sterility, does not change the physicochemical properties of the studied compound. The antimicrobial activity of ertapenem irradiated with the dose of 25 kGy was only reduced for one species. Based on the received results, we can conclude that radiostelization is a promising alternative method of obtaining sterile ertapenem. In our studies, ertapenem was also exposed to e-beam radiation with a dose of 400 kGy. It was determined that two novel degradation products that are structurally differently to degradants formed during hydrolysis and thermolysis.

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Improved Solubility of Vortioxetine Using C2-C4 Straight-Chain Dicarboxylic Acid Salt Hydrates

Crystals ◽

10.3390/cryst8090352 ◽

2018 ◽

Vol 8 (9) ◽

pp. 352 ◽

Cited By ~ 4

Author(s):

Lei Gao ◽

Xian-Rui Zhang ◽

Shao-Ping Yang ◽

Juan-Juan Liu ◽

Chao-Jie Chen

Keyword(s):

Dicarboxylic Acid ◽

Crystal Engineering ◽

Dicarboxylic Acids ◽

Acid Salt ◽

X Ray Diffraction ◽

Straight Chain ◽

Scanning Calorimetry ◽

X Ray ◽

Salt Hydrates ◽

Aliphatic Dicarboxylic Acids

The purpose of this study was to improve the solubility of vortioxetine by crystal engineering principles. In this paper, three C2-C4 straight-chain dicarboxylic acid salt hydrates of vortioxetine (VOT-OA, VOT-MA-H2O, and VOT-SUA-H2O, VOT = vortioxetine, OA = Oxalic acid, MA = malonic acid, SUA = succinic acid) were synthesized and characterized by single X-ray diffraction, powder X-ray diffraction, and differential scanning calorimetry. The single crystal structure of three salts reveals that vortioxetine has torsional flexibility, which can encourage VOT to allow combination with aliphatic dicarboxylic acids through N+-H···O hydrogen bonds. The solubility of all salts exhibits a dramatic increase in distilled water, especially for VOT-MA-H2O salt, where it shows the highest solubility, by 96-fold higher compared with pure vortioxetine.

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Melting Diagrams of Adefovir Dipivoxil and Dicarboxylic Acids: An Approach to Assess Cocrystal Compositions

Crystals ◽

10.3390/cryst9020070 ◽

2019 ◽

Vol 9 (2) ◽

pp. 70 ◽

Cited By ~ 2

Author(s):

Hyunseon An ◽

Insil Choi ◽

Il Kim

Keyword(s):

Solid State ◽

Adefovir Dipivoxil ◽

Sufficient Conditions ◽

Dicarboxylic Acids ◽

Current Approach ◽

X Ray Diffraction ◽

Scanning Calorimetry ◽

X Ray ◽

Pharmaceutical Ingredients ◽

Solution Crystallization

Pharmaceutical cocrystallization is a useful method to regulate the physical properties of active pharmaceutical ingredients (APIs). Since the cocrystals may form in various API/coformer ratios, identification of the cocrystal composition is the critical first step of any further analysis. However, the composition identification is not always unambiguous if cocrystallization is performed in solid state with unsuccessful solution crystallization. Single melting point and some new X-ray diffraction peaks are necessary but not sufficient conditions. In the present study, the use of melting diagrams coupled with the X-ray diffraction data was tested to identify cocrystal compositions. Adefovir dipivoxil (AD) was used as a model API, and succinic acid (SUC), suberic acid (SUB), and glutaric acid (GLU) were coformers. Compositions of AD/SUC and AD/SUB had been previously identified as 2:1 and 1:1, but that of AD/GLU was not unambiguously identified because of the difficulty of solution crystallization. Melting diagrams were constructed with differential scanning calorimetry, and their interpretation was assisted by powder X-ray diffraction. The cocrystal formation was exhibited as new compositions with congruent melting in the phase diagrams. This method correctly indicated the previously known cocrystal compositions of AD/SUC and AD/SUB, and it successfully identified the AD/GLU cocrystal composition as 1:1. The current approach is a simple and useful method to assess the cocrystal compositions when the crystallization is only possible in solid state.

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