Catalytic Aerobic N-Nitrosation by Secondary Nitroalkanes in Water: A Tandem Diazotization of Aryl Amines and Azo Coupling

Ramesh, Karu; Kim, Hun Young; Oh, Kyungsoo

doi:10.1021/acs.orglett.2c04353

Cited by 3 publications

(3 citation statements)

References 45 publications

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“…However, the reaction might not be complete, and other byproducts could be formed depending on the specific acid used and on the reaction conditions. In addition, the formation of nitrosating agents in rubber is a relatively difficult process [ 56 , 57 , 58 ], as mentioned previously. Nitrosating agents may be contaminants, non-rubber compounds, or they may have formed by oxidation.…”

Section: Resultsmentioning

confidence: 99%

Advancement of an Environmentally Friendly and Innovative Sustainable Rubber Wrap Film with Superior Sealing Properties

Suchat,

Boonrasri

2024

Polymers

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Common kitchen wraps like plastic and aluminum foil create significant environmental burdens. Plastic wrap, typically made from non-renewable fossil fuels, often ends up in landfills for centuries, breaking down into harmful microplastics. Aluminum foil, while effective, requires a large amount of energy to produce, and recycling it at home can be impractical due to food residue. A promising new alternative, low-nitrosamine rubber wrap film, aims to reduce waste by offering a reusable option compared to traditional single-use plastic wrap. The film is environmentally friendly, durable, and effective in sealing containers and keeping food fresh or crispy. The raw materials used to make the product were studied, namely fresh and concentrated natural rubber latex. No nitrosamines were found in either the fresh or concentrated latex, which is important as nitrosamines are known to be carcinogenic. The absence of nitrosamines in the raw materials suggests that the universal rubber wrap film is safe for use. In this study, the rubber formulation and properties of rubber used to make rubber wrap film were studied. The content of additives affecting the rubber properties was varied to find the optimum rubber formulation for making rubber wrap films. The rubber formulation with the least amount of chemicals that met the following criteria was selected: tensile strength of at least 15 MPa, elongation at break of at least 600%, and nitrosamine content below 6 ppm. It was found experimentally that the optimum rubber formulation for making a translucent rubber film had 0.7 phr zinc oxide and 1.0 phr sulfur. Performance tests revealed the rubber wrap film’s superior sealing capabilities. Its elasticity allows for a tighter fit on containers, effectively conforming to various shapes and creating an optimal seal compared to plastic wrap and aluminum foil. The results of this study provide valuable information for developing a universal rubber wrap film that is safe with low nitrosamines.

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Section: Resultsmentioning

confidence: 99%

Advancement of an Environmentally Friendly and Innovative Sustainable Rubber Wrap Film with Superior Sealing Properties

Suchat,

Boonrasri

2024

Polymers

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“…However, the reaction might not be complete, and other byproducts could be formed depending on the specific acid used and on the reaction conditions. In addition, the formation of nitrosating agents in rubber is a relatively difficult process [44][45][46], as mentioned previously. Nitrosating agents may be contaminants, non-rubber compounds, or they may have formed by oxidation.…”

Section: Fig 7 (A)mentioning

confidence: 92%

Advancement of an Eco-Friendly and Innovative Sustainable Rubber Wrap Film Exhibiting Superior Sealing Properties

Suchat,

Boonrasri

2024

Preprint

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The rubber wrap film is a promising new product that could have a positive impact on the en-vironment. The film is environmentally friendly, durable, and effective in sealing containers and keeping food fresh or crispy. The raw materials used to make the product were studied, namely fresh and concentrated natural rubber latex. No nitrosamines were found in either fresh or concentrated latex, which is important as nitrosamines are known to be carcinogenic. The absence of nitrosamines in the raw materials suggests that the universal rubber wrap film is safe for use. In this study, the rubber formulation and properties of rubber used to make rubber wrap film were studied. The content of additives affecting rubber properties was varied to find the optimum rubber formulation for making rubber wrap film. The rubber formulation with the least amount of chemicals that met the following criteria was selected: tensile strength at least 15 MPa, elongation at break at least 600%, and nitrosamine content below 6 ppm. It was found experimentally that the optimum rubber formulation for making a translucent rubber film had 0.7 phr zinc oxide and 1.0 phr sulfur. In actual use tests it was found that the translucent rubber wrap sealed containers more tightly than a PE plastic film or aluminum foil, because of its elasticity. This allows the rubber film to conform to the shape of the container more closely, creating a tighter seal. The results of this study provide valuable information for developing a universal rubber wrap film that is safe with low nitrosamines.

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“…While the earlier works of Cano-Yelo and Deronzier explored the visible-light-mediated reactions of diazonium salts using Ru(bpy) 3 2+ photocatalyst, the König group reignited the visible-light-promoted aryl radical chemistry of diazonium salts that evolved into one of the key synthetic transformations in recent years . With no diazonium alternatives to serve as “aryl cation synthons”, our group became interested in the photochemical behavior of areneazo-2-(2-nitro)propanes, derived from the aerobic diazotization of aryl amines using secondary nitroalkanes . Herein, we disclose the visible-light-generated aryl cations from areneazo-2-(2-nitro)propane derivatives and their use in the aromatic unimolecular nucleophilic substitution (S N 1) reactions with a variety of nucleophiles (Scheme c).…”

mentioning

confidence: 99%

Visible-Light-Promoted Aryl Cation Formation: Aromatic S_N1 Reactions of Areneazo-2-(2-nitro)propanes

Patil,

Ramesh,

Kim

et al. 2023

Org. Lett.

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The visible light excitation of areneazo-2-(2-nitro)propane·HCl salts generated the singlet aryl cation that readily underwent aromatic SN1 reactions with a variety of nucleophiles. The in situ generated singlet aryl cation was stabilized by a counter nitronate anion that prevented other intersystem crossing and single electron transfer processes. With the improved safety features of neutral areneazo-2-(2-nitro)propane derivatives, the current visible-light-promoted aromatic SN1 reactions provide an alternative aryl Csp2 –X bond forming strategy.

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Catalytic Aerobic N-Nitrosation by Secondary Nitroalkanes in Water: A Tandem Diazotization of Aryl Amines and Azo Coupling

Cited by 3 publications

References 45 publications

Advancement of an Environmentally Friendly and Innovative Sustainable Rubber Wrap Film with Superior Sealing Properties

Advancement of an Environmentally Friendly and Innovative Sustainable Rubber Wrap Film with Superior Sealing Properties

Advancement of an Eco-Friendly and Innovative Sustainable Rubber Wrap Film Exhibiting Superior Sealing Properties

Visible-Light-Promoted Aryl Cation Formation: Aromatic S_N1 Reactions of Areneazo-2-(2-nitro)propanes

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Catalytic Aerobic N-Nitrosation by Secondary Nitroalkanes in Water: A Tandem Diazotization of Aryl Amines and Azo Coupling

Cited by 3 publications

References 45 publications

Advancement of an Environmentally Friendly and Innovative Sustainable Rubber Wrap Film with Superior Sealing Properties

Advancement of an Environmentally Friendly and Innovative Sustainable Rubber Wrap Film with Superior Sealing Properties

Advancement of an Eco-Friendly and Innovative Sustainable Rubber Wrap Film Exhibiting Superior Sealing Properties

Visible-Light-Promoted Aryl Cation Formation: Aromatic SN1 Reactions of Areneazo-2-(2-nitro)propanes

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Visible-Light-Promoted Aryl Cation Formation: Aromatic S_N1 Reactions of Areneazo-2-(2-nitro)propanes