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Separate mechanisms of ion oligomerization tune the physicochemical properties of n-butylammonium acetate: cation-base clusters vs. anion-acid dimers
Berton, Paula1; Kelley, Steven P.1; Wang, Hui2; Myerson, Allan S.3,4; Rogers, Robin D.1,5
2017-10-07
Source PublicationPHYSICAL CHEMISTRY CHEMICAL PHYSICS
ISSN1463-9076
Volume19Issue:37Pages:25544-25554
Abstract

We investigated the ability of the ions comprising protic ionic liquids to strongly interact with their neutral acid and base forms through the characterization of n-butylammonium acetate ([C4NH3][OAc]) in the presence of excess n-butylamine (C4NH2) or excess acetic acid (HOAc). The conjugate and parent acid or base form new nonstoichiometric, noncovalently bound species (i.e., oligomeric ions) which change the physical and chemical properties of the resulting liquids, thus offering tunability. The effects of adding C4NH2 or HOAc to [C4NH3][OAc] on the resulting thermal and spectroscopic properties differ and suggest that C4NH2 interacts primarily with [C4NH3](+) to form 3-dimensional polymeric networks likely similar to those in H2O/[H3O](+),while HOAc interacts primarily with [OAc](-) to form oligomeric ions (e.g., [H(OAc)(2)](-)). The densities of the systems increased with the increase of acid content and reached a maximum when the acid molar fraction was 0.90, but decreased with increasing amine concentration. The viscosities decreased significantly with increasing acid or base concentration. The solvent properties of the mixtures were assessed by measuring the solubilities of benzene, ethyl acetate, diethyl ether, heptane, ibuprofen free acid, and lidocaine free base. The solubilities of the organic solutes and active pharmaceutical ingredients can be tuned with the concentration of acid or amine in the mixtures. In addition, crystallization of the active pharmaceutical ingredients can be induced with the modification of the composition of the mixtures. These observations support the usage of these mixtures for the synthesis and purification of acid or basic active pharmaceutical ingredients in the pharmaceutical industry.

SubtypeArticle
WOS HeadingsScience & Technology ; Physical Sciences
DOI10.1039/c7cp04078d
Indexed BySCI
Language英语
WOS KeywordBinary-mixtures ; Physical-properties ; Aqueous-solutions ; Liquid-mixtures ; Salts ; Solubility ; Ionicity ; Water ; n,N-dimethylformamide ; Conductivity
WOS Research AreaChemistry ; Physics
WOS SubjectChemistry, Physical ; Physics, Atomic, Molecular & Chemical
Funding OrganizationNovartis-Massachusetts Institute of Technology (MIT) Center for Continuous Manufacturing (CCM) ; Novartis International AG ; Canada Excellence Research Chairs Program
WOS IDWOS:000412271600033
Citation statistics
Document Type期刊论文
Identifierhttp://ir.ipe.ac.cn/handle/122111/23252
Collection研究所(批量导入)
Affiliation1.McGill Univ, Dept Chem, 801 Sherbrooke St West, Montreal, PQ H3A 0B8, Canada
2.Chinese Acad Sci, Inst Proc Engn, Beijing 100190, Peoples R China
3.MIT, Novartis MIT Ctr Continuous Mfg, 77 Massachusetts Ave, Cambridge, MA 02139 USA
4.MIT, Dept Chem Engn, Cambridge, MA 02139 USA
5.525 Solut Inc, 720 2nd St, Tuscaloosa, AL 35401 USA
Recommended Citation
GB/T 7714
Berton, Paula,Kelley, Steven P.,Wang, Hui,et al. Separate mechanisms of ion oligomerization tune the physicochemical properties of n-butylammonium acetate: cation-base clusters vs. anion-acid dimers[J]. PHYSICAL CHEMISTRY CHEMICAL PHYSICS,2017,19(37):25544-25554.
APA Berton, Paula,Kelley, Steven P.,Wang, Hui,Myerson, Allan S.,&Rogers, Robin D..(2017).Separate mechanisms of ion oligomerization tune the physicochemical properties of n-butylammonium acetate: cation-base clusters vs. anion-acid dimers.PHYSICAL CHEMISTRY CHEMICAL PHYSICS,19(37),25544-25554.
MLA Berton, Paula,et al."Separate mechanisms of ion oligomerization tune the physicochemical properties of n-butylammonium acetate: cation-base clusters vs. anion-acid dimers".PHYSICAL CHEMISTRY CHEMICAL PHYSICS 19.37(2017):25544-25554.
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