Solubility of fluorinated pharmaceuticals in dense carbon dioxide

Antero Laitinen (Corresponding Author), Olli Jauhiainen, Olli Aaltonen

Research output: Contribution to journalArticleScientificpeer-review

10 Citations (Scopus)

Abstract

The solubilities of benzoic acid and fluorinated benzoic acid derivatives in dense carbon dioxide were measured at 35 °C and 55 °C to find out how much fluorination increases the solubility of organic pharmaceuticals in dense carbon dioxide. The solubilities of two higher molecular weight pharmaceuticals, triflupromazine and flufenamic acid, in dense carbon dioxide were also measured. The solubility of benzoic acid is approximately 0.2 wt% at 35 °C and 100 bar. Attaching one fluorine atom increased the solubility of benzoic acid slightly, and the solubility of 3-tluorobenzoic acid was approximately 1 wt%. The solubility of 3,4-difluorobenzoic acid was 1.3 wt% at 35 °C and 103 bar. Introduction oftrifluoromethyl-group increased the solubility significantly, and the solubility of 3-(trifluoromethyl)benzoic acid in dense carbon dioxide at 35 °C and 100 bar was approximately 7 wt%, which is almost 40 times higher than the solubility of benzoic acid in same conditions. The solubility of triflupromazine was relatively high, i.e. 4.4 wt% at 43 °C and 145 bar. Flufenamic acid was very sparingly soluble at ambient temperatures (<50 °C), and 70-80 °C was necessary to reach 1-3 wt% solubility. These experiments show that dense carbon dioxide is a feasible solvent for fluorinated pharmaceuticals and that the fluorine content of a compound can be used as a clue to find carbon dioxide soluble molecules.
Original languageEnglish
Pages (from-to)353 - 356
Number of pages4
JournalOrganic Process Research and Development
Volume4
Issue number5
DOIs
Publication statusPublished - 2000
MoE publication typeA1 Journal article-refereed

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Carbon Dioxide
carbon dioxide
solubility
Solubility
Benzoic Acid
benzoic acid
Pharmaceutical Preparations
Triflupromazine
Flufenamic Acid
acids
Fluorine
fluorine
Fluorination
Acids
fluorination
ambient temperature
molecular weight
Molecular weight
Derivatives
Atoms

Cite this

@article{005b83cc628f47b694a687c745019666,
title = "Solubility of fluorinated pharmaceuticals in dense carbon dioxide",
abstract = "The solubilities of benzoic acid and fluorinated benzoic acid derivatives in dense carbon dioxide were measured at 35 °C and 55 °C to find out how much fluorination increases the solubility of organic pharmaceuticals in dense carbon dioxide. The solubilities of two higher molecular weight pharmaceuticals, triflupromazine and flufenamic acid, in dense carbon dioxide were also measured. The solubility of benzoic acid is approximately 0.2 wt{\%} at 35 °C and 100 bar. Attaching one fluorine atom increased the solubility of benzoic acid slightly, and the solubility of 3-tluorobenzoic acid was approximately 1 wt{\%}. The solubility of 3,4-difluorobenzoic acid was 1.3 wt{\%} at 35 °C and 103 bar. Introduction oftrifluoromethyl-group increased the solubility significantly, and the solubility of 3-(trifluoromethyl)benzoic acid in dense carbon dioxide at 35 °C and 100 bar was approximately 7 wt{\%}, which is almost 40 times higher than the solubility of benzoic acid in same conditions. The solubility of triflupromazine was relatively high, i.e. 4.4 wt{\%} at 43 °C and 145 bar. Flufenamic acid was very sparingly soluble at ambient temperatures (<50 °C), and 70-80 °C was necessary to reach 1-3 wt{\%} solubility. These experiments show that dense carbon dioxide is a feasible solvent for fluorinated pharmaceuticals and that the fluorine content of a compound can be used as a clue to find carbon dioxide soluble molecules.",
author = "Antero Laitinen and Olli Jauhiainen and Olli Aaltonen",
note = "Project code: K9SU00430",
year = "2000",
doi = "10.1021/op000036b",
language = "English",
volume = "4",
pages = "353 -- 356",
journal = "Organic Process Research and Development",
issn = "1083-6160",
publisher = "American Chemical Society",
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Solubility of fluorinated pharmaceuticals in dense carbon dioxide. / Laitinen, Antero (Corresponding Author); Jauhiainen, Olli; Aaltonen, Olli.

In: Organic Process Research and Development, Vol. 4, No. 5, 2000, p. 353 - 356.

Research output: Contribution to journalArticleScientificpeer-review

TY - JOUR

T1 - Solubility of fluorinated pharmaceuticals in dense carbon dioxide

AU - Laitinen, Antero

AU - Jauhiainen, Olli

AU - Aaltonen, Olli

N1 - Project code: K9SU00430

PY - 2000

Y1 - 2000

N2 - The solubilities of benzoic acid and fluorinated benzoic acid derivatives in dense carbon dioxide were measured at 35 °C and 55 °C to find out how much fluorination increases the solubility of organic pharmaceuticals in dense carbon dioxide. The solubilities of two higher molecular weight pharmaceuticals, triflupromazine and flufenamic acid, in dense carbon dioxide were also measured. The solubility of benzoic acid is approximately 0.2 wt% at 35 °C and 100 bar. Attaching one fluorine atom increased the solubility of benzoic acid slightly, and the solubility of 3-tluorobenzoic acid was approximately 1 wt%. The solubility of 3,4-difluorobenzoic acid was 1.3 wt% at 35 °C and 103 bar. Introduction oftrifluoromethyl-group increased the solubility significantly, and the solubility of 3-(trifluoromethyl)benzoic acid in dense carbon dioxide at 35 °C and 100 bar was approximately 7 wt%, which is almost 40 times higher than the solubility of benzoic acid in same conditions. The solubility of triflupromazine was relatively high, i.e. 4.4 wt% at 43 °C and 145 bar. Flufenamic acid was very sparingly soluble at ambient temperatures (<50 °C), and 70-80 °C was necessary to reach 1-3 wt% solubility. These experiments show that dense carbon dioxide is a feasible solvent for fluorinated pharmaceuticals and that the fluorine content of a compound can be used as a clue to find carbon dioxide soluble molecules.

AB - The solubilities of benzoic acid and fluorinated benzoic acid derivatives in dense carbon dioxide were measured at 35 °C and 55 °C to find out how much fluorination increases the solubility of organic pharmaceuticals in dense carbon dioxide. The solubilities of two higher molecular weight pharmaceuticals, triflupromazine and flufenamic acid, in dense carbon dioxide were also measured. The solubility of benzoic acid is approximately 0.2 wt% at 35 °C and 100 bar. Attaching one fluorine atom increased the solubility of benzoic acid slightly, and the solubility of 3-tluorobenzoic acid was approximately 1 wt%. The solubility of 3,4-difluorobenzoic acid was 1.3 wt% at 35 °C and 103 bar. Introduction oftrifluoromethyl-group increased the solubility significantly, and the solubility of 3-(trifluoromethyl)benzoic acid in dense carbon dioxide at 35 °C and 100 bar was approximately 7 wt%, which is almost 40 times higher than the solubility of benzoic acid in same conditions. The solubility of triflupromazine was relatively high, i.e. 4.4 wt% at 43 °C and 145 bar. Flufenamic acid was very sparingly soluble at ambient temperatures (<50 °C), and 70-80 °C was necessary to reach 1-3 wt% solubility. These experiments show that dense carbon dioxide is a feasible solvent for fluorinated pharmaceuticals and that the fluorine content of a compound can be used as a clue to find carbon dioxide soluble molecules.

U2 - 10.1021/op000036b

DO - 10.1021/op000036b

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