Synthesis of Derivatives of (1R)-(-)- and (1S)-(+)-10-Camphorsulfonic Acid

Cermak, Steven C.; Wiemer, David F.

doi:10.1021/ed076p1715

Cited by 4 publications

(4 citation statements)

References 3 publications

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“…Again, the chirality has as expected no impact on the phase behavior of the neat salts, but also points to accurate preparation and purity as well as sample preparation. The same has been observed for other 48 Again, the same as the TGA T d data, for a given anion, the lithium salts possess lower T m as compared to the corresponding potassium salts. This diverges from the TFSI salts, where KTFSI has a lower T m (199 °C) than LiTFSI (233 °C) 49 and can be rationalized by the different lattice energies, originating from the greatly complicated electrostatic interactions of these bulky organic anions with different cations, as previously observed for other sulfonimide salts, e.g., for salts of the (fluorosulfonyl)(pentafluoroethanesulfonyl)imide (FPFSI) anion, where LiFPFSI has a T m = 152 °C and KFPFSI is more high melting (T m = 173 °C).…”

Section: Resultssupporting

confidence: 82%

Solid Polymer Electrolytes Comprising Camphor-Derived Chiral Salts for Solid-State Batteries

Qiao

Santiago

Zhang

et al. 2020

J. Electrochem. Soc.

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Solid polymer electrolytes (SPEs) with both excellent processability and flexibility have been deemed as an auspicious alternative to develop safe solid-state lithium metal (Li°) batteries (SSLMBs). The electrochemical performance of SSLMBs is ultimately associated with the nature of the Li-salt anion and the widely used bis(trifluoromethanesulfonyl)imide anion (TFSI) is "slippery" due to its perfluorinated nature and therefore highly mobile, which leads to severe polarization upon battery cell charge/discharge cycles. In this work, we report on a new type of chiral salts, synthesized from commercially available camphorsulfonic acid, used in poly(ethylene oxide) (PEO)-based SPEs. The impact of the chirality of the anions on the fundamental physical properties of the SPEs is extensively studied in terms of thermal stability, phase transition and ionic conductivity, etc. We demonstrate that the resulting SPEs exhibit agreeable ionic conductivities (ca. 10 -4 S cm -1 ) accompanied by high cation transference numbers (ca. 0.5) at 70 °C. Whether either the R or the S enantiomers are used the ion transport properties are the same, as expected, but rather surprisingly the artificial racemic mixture is within the errors of the measurements just as conductive. We discuss how this opens a new avenue to design novel salts for reaching high-performant SSLMBs.

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Section: Resultssupporting

confidence: 82%

Solid Polymer Electrolytes Comprising Camphor-Derived Chiral Salts for Solid-State Batteries

Qiao

Santiago

Zhang

et al. 2020

J. Electrochem. Soc.

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“…Camphor sulfonic acid (CSA) is an important organic intermediate and chiral resolve agent, which has been widely used in pharmaceutical, light and daily chemical industries. [1][2][3][4][5] Especially in the field of optically active drugs, the optically active L-10-camphorsulfonic acid (L-CSA) is an important intermediate for many drugs, 6 such as the synthesis of clopidogrel bisulfate 7 and bis-indole acenaphthene quinone compounds. 8,9 However, L-CSA cannot be directly prepared by the sulfonation of natural camphor, but can only be isolated from the synthetic camphor sulfonic acid.…”

Section: Introductionmentioning

confidence: 99%

Bipolar membrane electrodialysis for clean production of L‐10‐camphorsulfonic acid: From laboratory to industrialization

Yan

Wang

et al. 2021

AIChE Journal

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In this study, bipolar membrane electrodialysis (BMED) was implemented for cleaner production of L-10-camphorsulfonic acid (L-CSA) to lower the environmental impact.Under the current density of 300-400 A/m 2 and feed salt concentration of 6-10 wt. %, the energy consumption and current efficiency were 2.24-2.70 kWh/kg and 20.89-29.5%, respectively. Positron annihilation lifetime spectroscopy, x-ray photoelectron spectroscopy with ion beam etching, and other characterizations were used to elucidate the transport behaviors of large-sized anions across the membranes. It was speculated that the large-sized camphor sulfonate ions were more likely to deposit on the surface of the anion-exchange membrane to form a deposition layer under a direct current electric field. The appearance of water splitting at this deposition layer would offset the water dissociation in the bipolar membrane. Nevertheless, the successful commissioning of industrial-scale stack proved the feasibility and sustainability of BMED technique for a closed loop L-CSA production.

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“…For this reason, multiple teaching activities have been designed for use during lectures in order to help students build mental models of chiral molecular structures. − However, there are not as many laboratory experiments that teach students about the concept of chirality . Typically, students carry out experiments involving resolution, ,− polarimetry, ,, or the synthesis of chiral compounds. − Even when not the focus of an experiment, specific rotation values are typically used as evidence that an optically active compound was synthesized. None of these experiments, however, allow students to observe a palpable, visual display of chirality.…”

Section: Introductionmentioning

confidence: 99%

Visualizing Molecular Chirality in the Organic Chemistry Laboratory Using Cholesteric Liquid Crystals

2016

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Although stereochemistry is an important topic in second-year undergraduate organic chemistry, there are limited options for laboratory activities that allow direct visualization of macroscopic chiral phenomena. A novel, guided-inquiry experiment was developed that allows students to explore chirality in the context of cholesteric liquid crystals. As part of the experiment, which requires no specialized equipment, students visually distinguish two enantiomers. A chiral imine is synthesized in one step from an assigned (but unknown to students) enantiomer of 1-phenylethylamine and then dissolved in a nematic liquid crystal host, inducing a helical structure. The resulting cholesteric liquid crystalline material selectively reflects circularly polarized light with a handedness that depends on the absolute configuration of the starting amine, easily detected using circularly polarizing filters from disposable 3D glasses. Working in teams, students examine the behavior of both dopant enantiomers and the racemic mixture. Analysis of our students’ responses to post-lab questions indicates comprehension of most of the ideas introduced in lab.

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Synthesis of Derivatives of (1R)-(-)- and (1S)-(+)-10-Camphorsulfonic Acid

Cited by 4 publications

References 3 publications

Solid Polymer Electrolytes Comprising Camphor-Derived Chiral Salts for Solid-State Batteries

Solid Polymer Electrolytes Comprising Camphor-Derived Chiral Salts for Solid-State Batteries

Bipolar membrane electrodialysis for clean production of L‐10‐camphorsulfonic acid: From laboratory to industrialization

Visualizing Molecular Chirality in the Organic Chemistry Laboratory Using Cholesteric Liquid Crystals

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