Green Hydrogenation: Solvent-Free Hydrogenation of Pinenes for An Undergraduate Organic Chemistry Laboratory

Touaibia, Mohamed; Selka, Ayyoub; Levesque, Natalie A.; St-Onge, Pierre A.

doi:10.1021/acs.jchemed.9b01026

Cited by 4 publications

(4 citation statements)

References 19 publications

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“…Furthermore, this synthetic route stresses green principles through the use of a solventless reaction, employment of microwave irradiation to reduce heating time, and the implementation of a three-step synthesis that does not require purification between steps. While the literature contains pedagogical examples of multistep synthesis − and single-step green chemistry transformations, − there exists a need for more pedagogical examples of multistep transformations that consider green principles for each step.…”

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confidence: 84%

Multistep Microwave-Assisted Synthesis of Avobenzone

et al. 2022

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Multistep synthesis is a key capstone experience in organic laboratory instruction. Here, a four-step synthesis of avobenzone, an active component in sunscreens, has been developed that can be completed in two 4 h laboratory periods. This synthesis incorporates green principles and includes an aldol condensation, electrophilic addition of bromine to an alkene, an E2 dehalogenation of a dibromide, and hydration of an alkyne. Highlights of this synthesis include the use of coupling constants to identify alkene configuration, NMR analysis to determine preferred tautomeric form, the use of microwave irradiation to reduce reaction times, a solvent-free synthesis of a chalcone, and a three-step reaction that can be completed in a single lab period.

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confidence: 84%

Multistep Microwave-Assisted Synthesis of Avobenzone

et al. 2022

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“…• Castor oil was hydrogenated by hydrogen atom transfer from limonene in the presence of 1% Pd/C by refluxing at 176 °C for 30 min or microwave heating for 20 min. 10 • Pinene was hydrogenated using hydrogen gas in the presence of 10% Pd/C at 1 atm using a balloon and heating at 100 °C for 3−4 h or at 27 atm using a roomtemperature autoclave for 4 h. 11 A final activity connected melting points and molecular shape for fatty acids and triglycerides. The exercise included assembling molecular models to consider how those molecules might interact, as well as graphing melting points.…”

Section: ■ Introductionmentioning

confidence: 99%

“… Castor oil was hydrogenated by hydrogen atom transfer from limonene in the presence of 1% Pd/C by refluxing at 176 °C for 30 min or microwave heating for 20 min Pinene was hydrogenated using hydrogen gas in the presence of 10% Pd/C at 1 atm using a balloon and heating at 100 °C for 3–4 h or at 27 atm using a room-temperature autoclave for 4 h …”

Section: Introductionmentioning

confidence: 99%

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Intermolecular Forces and the Languages of Chemistry

Lisensky,

Kueffer,

Livingston

et al. 2024

J. Chem. Educ.

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The concept of intermolecular forces is challenging because students often revert to intramolecular explanations when discussing macroscopic properties. This set of activities from our general chemistry course aimed to use the different languages of chemistry to help build a more solid, multilevel understanding of intermolecular forces. Through the symbolic language of graphing, students were first asked to explore the relationship among melting point, molecular weight, and structure. Macroscopic language was used during a lab activity where students hydrogenated common kitchen oils and saw a change from liquid to solid. In another activity, students employed atomic/molecular/ particulate language in building models and thinking about the interactions between molecules. They were asked to make use of all three languages in examining the intermolecular forces relevant to the melting points of fatty acids and triglycerides.

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Selective Hydrogenation of Unsaturated Vinyl Ethers in Two‐Chamber Gauge‐Reactor

Gyrdymova,

Saybulina,

Mironenko

et al. 2024

Asian J Org Chem

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A pressure gauge was incorporated into a two‐chamber glass H‐tube to continuously monitor the pressure inside a reactor when working with gases. The ex situ generated H2, D2, acetylene and CO2 were tested in pressure gauge reactors, and calibration curves were plotted. A series of unsaturated compounds with two or more double C=C bonds accessible for hydrogenation were synthesized for hydrogenation. The hydrogenation proceeded well due to constant pressure control, and the desired products were isolated in good yields. The same hydrogenation procedures were then carried out using steel autoclaves to verify the results and compare them. Surprisingly, almost the same results were obtained, confirming the effectiveness of self‐made glass reactors. The hydrogenation mechanism was further investigated using D‐labeled reagents. The kinetics of hydrogenation was studied both in manometric glass reactors and in steel autoclaves, which showed a similar nature of the main process in both reaction units. Thus, the created reactors can be effectively used in barometric transformations instead of steel autoclaves in appropriate cases.

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Green Hydrogenation: Solvent-Free Hydrogenation of Pinenes for An Undergraduate Organic Chemistry Laboratory

Cited by 4 publications

References 19 publications

Multistep Microwave-Assisted Synthesis of Avobenzone

Multistep Microwave-Assisted Synthesis of Avobenzone

Intermolecular Forces and the Languages of Chemistry

Selective Hydrogenation of Unsaturated Vinyl Ethers in Two‐Chamber Gauge‐Reactor

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