The Cyclohexanol Cycle and Synthesis of Nylon 6,6: Green Chemistry in the Undergraduate Organic Laboratory

Dintzner, Matthew R.; Kinzie, Charles R.; Pulkrabek, Kimberly A.; Arena, Anthony F.

doi:10.1021/ed2000878

Cited by 24 publications

(16 citation statements)

References 34 publications

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“…Students are guided to devise a more sustainable solvent system for Grignard reactivity based upon their own acquired data and that provided to them. A one-term, integrated project for the undergraduate organic laboratory involves synthesis of Nylon 6,6 from cyclohexanol (Dintzner et al, 2012). The product of one reaction is used as a starting material for the following one in an effort to minimize waste, and students are exposed to several other green principles in the context of a familiar target compound.…”

Section: Laboratory Resourcesmentioning

confidence: 99%

Green chemistry teaching in higher education: a review of effective practices

Andraos

Dicks

2012

Chem. Educ. Res. Pract.

107

122

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This account reviews published green chemistry teaching resources in print and online literature and our experiences in teaching the subject to undergraduate students. Effective practices in lecture and laboratory are highlighted and ongoing challenges are addressed, including areas in cutting edge green chemistry research that impact its teaching in the undergraduate curriculum. In particular, the influence of green chemistry on the overall teaching of organic chemistry is discussed. Challenges in teaching green chemistry 1. Examples across the chemical sub-disciplinesMost literature examples of green chemistry in the context of optimized syntheses are from an organic perspective. This includes pharmaceutically important target molecules such as sildenafil citrate (Viagrat) (Dunn et al., 2004;Dicks and Batey, 2012;Edward, 2012) and ibuprofen (Advilt) (Cann and Connelly, 2000). As such, the vast majority of green

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Section: Laboratory Resourcesmentioning

confidence: 99%

Green chemistry teaching in higher education: a review of effective practices

Andraos

Dicks

2012

Chem. Educ. Res. Pract.

107

122

View full text Add to dashboard Cite

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“…Theory Teaching of polymer science, such as different polymerization methods, kinetics, and molecular weight analyses, as well as dedicated polymer lab courses, is becoming more and more important in the chemical education system. , Although many new polymerization methods and chemical structures have been introduced into lab courses for undergraduate students, − as far as we know, functional polymers based on dynamic chemistries are relatively rare in lab courses. Although many polymer characterization experiments have been introduced into lab courses for undergraduate students, − characterizations with an emphasis on polymer physics properties such as shape memory, reprocessability (welding experiment), and thermal and mechanical properties are not so common.…”

Section: Introductionmentioning

confidence: 99%

“Reprocessable Thermosets”: Synthesis and Characterization of Vitrimer in the Undergraduate Lab Course

Chen

Yang

et al. 2021

J. Chem. Educ.

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This article introduces a novel experiment that involves vitrimers, a new type of polymer, in polymer chemistry and physics lab courses for undergraduate students. Vitrimers are permanently cross-linked networks that can be reprocessed under certain external stimuli. Therefore, they combine the advantages of traditional thermoplastics (excellent reprocessability) with thermosets (outstanding mechanical properties and environmental stability). They can be regarded as a kind of “special thermoset”, which moves this industry toward a more sustainable path, as they are conducive to decreasing thermosetting wastes, reducing environmental pollution, and cutting down the waste of resources. From this lab class, students obtained more experience in the preparation and characterization of polymers. They also learned the concepts of dynamic chemistries and vitrimers and gained a better understanding of the advantages and limitations of thermosets and thermoplastics, as well as a strategy for making a reprocessable thermoset polymeric material. It also fostered students’ interest in functional materials and inspired them to design other functional materials. Moreover, this experimental setup is convenient and safe for implementation and dissemination in most undergraduate laboratory classes.

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“…Green chemistry principles involve the use of safer alternatives to hazardous chemicals. − Following the growing trend of green chemistry, many educators have striven to make introductory organic chemistry lab experiments more environmentally benign. − Systems thinking influences green chemistry approaches and has informed much of the progress made in green chemistry . Systems thinking also encourages chemists to recognize the interdependence of chemistry with other disciplines and consider how they are related.…”

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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The Cyclohexanol Cycle and Synthesis of Nylon 6,6: Green Chemistry in the Undergraduate Organic Laboratory

Cited by 24 publications

References 34 publications

Green chemistry teaching in higher education: a review of effective practices

Green chemistry teaching in higher education: a review of effective practices

“Reprocessable Thermosets”: Synthesis and Characterization of Vitrimer in the Undergraduate Lab Course

A Green Nucleophilic Aromatic Substitution Reaction

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