Prediction of Setschenow constants

Ni, Nina; Yalkowsky, Samuel H.

doi:10.1016/s0378-5173(03)00008-5

Cited by 101 publications

(104 citation statements)

References 20 publications

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“…Two partially insoluble phases are formed, an organic phase containing THF, a small amount of water, allylcarbinol and other organic impurities, and an aqueous phase containing water, THF and partially soluble MgCl 2 salts. THF and water are totally miscible unless the MgCl 2 salts and allylcarbinol are present (salting-out effect 41 ), in which case they are only partially miscible.…”

Section: Organic Process Research and Developmentmentioning

confidence: 99%

Continuous Hydrolysis and Liquid–Liquid Phase Separation of an Active Pharmaceutical Ingredient Intermediate Using a Miniscale Hydrophobic Membrane Separator

Cervera-Padrell

Morthensen

Lewandowski

et al. 2012

Org. Process Res. Dev.

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Continuous hydrolysis of an active pharmaceutical ingredient intermediate, and subsequent liquid−liquid (L-L) separation of the resulting organic and aqueous phases, have been achieved using a simple PTFE tube reactor connected to a miniscale hydrophobic membrane separator. An alkoxide product, obtained in continuous mode by a Grignard reaction in THF, reacted with acidic water to produce partially miscible organic and aqueous phases containing Mg salts. Despite the partial THF− water miscibility, the two phases could be separated at total flow rates up to 40 mL/min at different flow ratios, using a PTFE membrane with 28 cm 2 of active area. A less challenging separation of water and toluene was achieved at total flow rates as high as 80 mL/min, with potential to achieve even higher flow rates. The operability and flexibility of the membrane separator and a plate coalescer were compared experimentally as well as from a physical viewpoint. Surface tension-driven L-L separation was analyzed in general terms, critically evaluating different designs. It was shown that microporous membrane L-L separation can offer very large operating windows compared to other separation devices thanks to a high capillary pressure (Laplace pressure) combined with a large number of pores per unit area offering low pressure drop. The separation device can easily be operated by means of a back-pressure regulator ensuring flow-independent separation efficiency. Simple monitoring and control strategies as well as scaling-up/out approaches are proposed, concluding that membrane-based L-L separation may become a standard unit operation for continuous pharmaceutical manufacturing.

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Section: Organic Process Research and Developmentmentioning

confidence: 99%

Continuous Hydrolysis and Liquid–Liquid Phase Separation of an Active Pharmaceutical Ingredient Intermediate Using a Miniscale Hydrophobic Membrane Separator

Cervera-Padrell

Morthensen

Lewandowski

et al. 2012

Org. Process Res. Dev.

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“…Salting-out effect on the solubility of organic compounds was extensively examined in the literature for various organic compounds but not for OCPs. Calculated or experimentally determined k s values of organic compounds range between 0.01 and 2.23 L mol À1 (Ni and Yalkowsky, 2003;Xie et al, 1997). Xie et al (1997) (Xie et al, 1997).…”

Section: Article In Pressmentioning

confidence: 99%

Determination of Henry's law constants of organochlorine pesticides in deionized and saline water as a function of temperature

Çetin

Özer

Sofuoğlu

et al. 2006

Atmospheric Environment

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The Henry's law constant (H) is an important parameter that is required to estimate the air-water exchange of semivolatile organic compounds. Henry's law constants for 17 banned/restricted/currently used organochlorine pesticides (OCPs) were experimentally determined using a gas-stripping technique in deionized and saline water (3%) over a temperature range of 5-35 1C. H values (at 25 1C) ranged between 0.06670.037 Pa m 3 mol À1 (endosulfan II) and 62.0724.2 Pa m 3 mol À1 (heptachlor) in deionized water while the range in saline water was 0.2870.03 Pa m 3 mol À1 (g-HCH) and 135.2731.3 Pa m 3 mol À1 (heptachlor). The increase in dimensionless Henry's law constants (H 0 ) for OCPs over the studied temperature range was between 3 (g-HCH)-19 times (chlorpyrifos) and 3 (endosulfan II)-80 times (transnonachlor) in deionized and saline water, respectively. The calculated enthalpies of phase change (DH H ) were within the ranges previously reported for OCPs and other organic compounds (23.8-100.2 kJ mol À1 ). The salting-out constant, k s , ranged between 0.04 (g-HCH) and 1.80 L mol À1 (endosulfan II) indicating the importance of assessing the H values of OCPs in saline water to accurately determine their partitioning and fate in seawater. r

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“…The experimental K salt data for 101 compounds in aqueous NaCl solution (Table 1) were taken from the article by Ni and Yalkowsky [6]. The reported K salt values ranged from -0.068 to 0.354.…”

Section: Datasetmentioning

confidence: 99%

“…the number of atom pairs at distance equal to k. The negative sign of GATS2m in Eq. (6) indicates that the compounds containing atoms with larger atomic masses would possess higher K salt , because this descriptor increases with increased atomic masses. …”

Section: T a B L Ementioning

confidence: 99%

“…The theoretical prediction of K salt has been carried out using several methods [1][2][3][4][5][6]; however, they require experimental physicochemical properties or ambiguously determined parameters, resulting in limited predictive ability. Therefore, predicting K salt directly from the molecular structure of the compound concerned it is of particular interest.…”

Section: Introductionmentioning

confidence: 99%

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A simple 2D-QSPR model for the prediction of Setschenow constants of organic compounds

Fan

2016

Maced. J. Chem. Chem. Eng.

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A quantitative structure-property relationship (QSPR) analysis of the Setschenow constants (K salt ) of organic compounds in a sodium chloride solution was carried out using only two-dimensional (2D) descriptors as input parameters. The whole set of 101 compounds was split into a training set of 71 compounds and a validation set of 30 compounds by means of the Kennard and Stones algorithm. A general four-parameter equation, with correlation coefficient (R) of 0.887 and standard error of estimation (s) of 0.031, was obtained by stepwise multilinear regression analysis (MLRA) on the training set. The reliability and robustness of the present model was verified with leave-one-out cross-validation, randomization tests, and the external validation set. All of the descriptors contained in this model are calculated directly from the molecular 2D structures; thus, this model can be used to easily predict the K salt of other compounds not involved in the present dataset.Keywords: QSPR; Setschenow constants; 2D descriptor; multilinear regression analysis ЕДНОСТАВЕН 2D-QSPR-МОДЕЛ ЗА ПРЕДВИДУВАЊЕ НА КОНСТАНТИТЕ НА SETSCHENOW ЗА ОРГАНСКИТЕ СОЕДИНЕНИЈААнализата на квантитативната зависност на структурата и својствата (QSPR) на константите на Setschenow (K salt ) на органските соединенија во раствор од натриум хлорид е извршена користејќи само дводимензионални (2D) дескриптори како влезни параметри. Целото множество од 101 соединение беше поделено во множество за подготовка од 71 соединение и множество за валидација од 30 соединенија според алгоритамот на Kennard и Stones. Од множеството за подготовка со мултилинеарна регресиона анализа MLRA е добиена општа четирипараметарска равенка со коефициент на корелација R = 0,887 и стандардна грешка на процената s = 0,031. Веродостојноста и робусноста на овој модел беше верифицирана со повеќе тестови: вкрстена валидација со испуштање на еден параметар, тест на рандомизација, како и екстерно множество за валидација. Сите дескриптори содржат модел што се пресметува директно од молекулските 2D-структури, и така овој модел може да се користи за едноставно предвидување на K salt на други соединенија што не се вклучени во ова множество на податоци.

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Prediction of Setschenow constants

Cited by 101 publications

References 20 publications

Continuous Hydrolysis and Liquid–Liquid Phase Separation of an Active Pharmaceutical Ingredient Intermediate Using a Miniscale Hydrophobic Membrane Separator

Continuous Hydrolysis and Liquid–Liquid Phase Separation of an Active Pharmaceutical Ingredient Intermediate Using a Miniscale Hydrophobic Membrane Separator

Determination of Henry's law constants of organochlorine pesticides in deionized and saline water as a function of temperature

A simple 2D-QSPR model for the prediction of Setschenow constants of organic compounds

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