Greening the organic chemistry laboratory: a comparison of microwave-assisted and classical nucleophilic aromatic substitution reactions

Latimer, Devin; Wiebe, Michael E.

doi:10.1080/17518253.2015.1065010

Cited by 6 publications

(7 citation statements)

References 37 publications

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“…Latimer and Wiebe compared the nucleophilic aromatic substitution reactions of 2,4-dinitrobromobenzene with one of the following nucleophiles: potassium thiocyanate, ethyl amine, or diethylamine. 56 The microwave-assisted substitution took place in 5 min with heating and used ethanol−water as the solvent system. Yields for these reactions improved by 1.3−2.0 times compared to the conventional heating method (1 h heating) using toluene as solvent (Scheme 34).…”

Section: Nucleophilic Aromatic Substitutionsupporting

confidence: 66%

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Environmentally Friendly Organic Chemistry Laboratory Experiments for the Undergraduate Curriculum: A Literature Survey and Assessment

Mohan

Mejia

2020

J. Chem. Educ.

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Due to a growing awareness of environmental issues, green chemistry concepts are increasingly being incorporated into the undergraduate organic chemistry lecture and laboratory component. This minireview summarizes environmentally friendly organic chemistry experiments suitable for undergraduate laboratories. Whenever feasible, LD50 values for various chemicals are provided to allow readers to determine the suitability of an experiment for their curriculum based on the toxicity of reagents used.

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Section: Nucleophilic Aromatic Substitutionsupporting

confidence: 66%

Section: Microwave-assisted Reactionsmentioning

confidence: 99%

Environmentally Friendly Organic Chemistry Laboratory Experiments for the Undergraduate Curriculum: A Literature Survey and Assessment

Mohan

Mejia

2020

J. Chem. Educ.

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“…These programs have a growing number of resources available such as the Green Chemistry Commitment where programs pledge to implement Green Chemistry Student Learning Objectives into curricula and several green chemistry laboratory manuals. − Green Chemistry concepts such as the 12 Principles of Green Chemistry , have been introduced in the undergraduate chemistry curriculum , as a qualitative tool to comparatively assess reactions. Quantitative metrics such as atom economy (AE), environmental factor (E-factor), − and process mass intensity (PMI), − that represent the incorporation of all reactant atoms stoichiometrically into the product, reaction waste, and process efficiency, respectively, have also been introduced. However, these are univariate metrics that are based on the mass of the product as the major determinant of conversion efficiency .…”

Section: Introductionmentioning

confidence: 99%

Green Chemistry, Life Cycle Assessment, and Systems Thinking: An Integrated Comparative-Complementary Chemical Decision-Making Approach

2022

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Chemistry students are passionate about using their learning to contribute toward a sustainable future, yet they feel unprepared to make green and sustainable practical decisions informed by industry-relevant tools. Most green chemistry metrics are mass-based, which do not estimate environmental impact or help address global socioeconomic challenges. We present the introduction of two complementary quantitative tools used in industry to compare greenness and environmental impacts of chemical reactions: (i) DOZN 2.0, a free online software inspired by the 12 principles of Green Chemistry and (ii) Life Cycle Assessment (LCA) metrics integrated with systems thinking to connect the chemical reactions to the UN SDGs. Students worked collaboratively on projects comparing two organic synthetic processes with the free, online software DOZN2.0 developed by MilliporeSigma to calculate aggregate scores and choose the greener synthesis. The chemical evaluation was complemented with quantified univariate green chemistry metrics and multivariate life-cycle impacts using nine LCA impact category indicators. The quantified results were considered with a systems thinking lens and connected to the UN SDGs. Students developed critical scientific communication skills by presenting their evaluation in a virtual presentation and in an industry-focused report. Responses to survey questions indicated that the use of the complementary tools empowered students to make more informed and insightful decisions that could not be supported by using a single tool. They felt more prepared to make sustainable decisions for careers in industry and academia and became more conscious of the role of chemists in environmental and social responsibility and justice.

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“…A discovery-based S N Ar experiment in water was reported to introduce chemistry students to micellar catalysis, green chemistry, and systems thinking . Latimer et al compared microwave-induced organic reaction enhancement to that of more traditional synthetic procedures toward S N Ar reaction . Rizvi et al determined the activation energy of S N Ar on porphyrins .…”

Section: Introductionmentioning

confidence: 99%

“…38 Latimer et al compared microwave-induced organic reaction enhancement to that of more traditional synthetic procedures toward S N Ar reaction. 39 Rizvi et al determined the activation energy of S N Ar on porphyrins. 40 Goodrich et al employed S N Ar reaction as one of the reactions in the synthesis of a fluorescent acridone.…”

Section: ■ Introductionmentioning

confidence: 99%

A Green Nucleophilic Aromatic Substitution Reaction

Abraham

2020

J. Chem. Educ.

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This paper revisits the tie-dyeing process through a bioinspired and safer alternative to nucleophilic aromatic substitution (SNAr) reactions for an introductory organic chemistry laboratory. The simple and straightforward experiment provides students with an opportunity to gain practical experience in conducting a chemical reaction in a real-world context while applying concepts of design for biodegradability and reusability. The water-soluble reactive dye that replaces the use of a conventional SNAr substrate does not require any heavy metals, toxic substances, or mordants but utilizes a much less toxic and safer sodium carbonate to generate the cellulosate nucleophile. This reaction generates no waste, and the end-product, the tie-dyed T-shirt, is reusable and biodegradable. Through this experiment, students can see connections between chemistry and environmental health while gaining a practical insight into dyeing chemistry, making use of a systems thinking approach. This experiment serves not only to employ safer alternatives to hazardous chemicals in the undergraduate organic chemistry laboratory but also to educate students to recognize the relevance and importance of applying green chemistry wherever it is possible, emphasizing life cycle thinking and stewardship.

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Greening the organic chemistry laboratory: a comparison of microwave-assisted and classical nucleophilic aromatic substitution reactions

Cited by 6 publications

References 37 publications

Environmentally Friendly Organic Chemistry Laboratory Experiments for the Undergraduate Curriculum: A Literature Survey and Assessment

Environmentally Friendly Organic Chemistry Laboratory Experiments for the Undergraduate Curriculum: A Literature Survey and Assessment

Green Chemistry, Life Cycle Assessment, and Systems Thinking: An Integrated Comparative-Complementary Chemical Decision-Making Approach

A Green Nucleophilic Aromatic Substitution Reaction

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