Acetylene and Ethylene: Universal C2 Molecular Units in Cycloaddition Reactions

Ledovskaya, Maria S.; Voronin, V. V.; Rodygin, Konstantin S.; Ananikov, Valentine P.

doi:10.1055/a-1654-2318

Cited by 20 publications

(11 citation statements)

References 404 publications

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“…10,11,12,13,14,15,16 The development of cycloaddition reactions involving acetylene has experienced a resurgence in recent years and is another exciting area. 17 In the context of space, the situation around acetylene becomes even more intricate and fascinating. Chemical evolution from monatomic particles to complex carbon systems is a central issue in astrochemistry.…”

Section: Introductionmentioning

confidence: 99%

“…Acetylene serves as a precursor for many industrial products, including vinyl chloride, vinyl acetate, acrylic acid, 1,4-butynediol, and carbon black. The production and industrial use of acetylene are among the global market indicators, , and new potential applications of acetylene have recently been discovered. ,,, For example, new methods for producing carbon materials such as carbon nanotubes and graphene are of particular interest. ,,,,,, The development of cycloaddition reactions involving acetylene has experienced a resurgence in recent years and is another exciting area …”

Section: Introductionmentioning

confidence: 99%

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Role of Acetylene in the Chemical Evolution of Carbon Complexity

Pentsak,

Murga,

Ananikov

2024

ACS Earth Space Chem.

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Acetylene, among the multitude of organic molecules discovered in space, plays a distinct role in the genesis of organic matter. Characterized by its unique balance of stability and reactivity, acetylene is the simplest unsaturated organic molecule known to have a triple bond. In addition to its inherent chemical properties, acetylene is one of the most prevalent organic molecules found across the Universe, spanning from the icy surfaces of planets and satellites and the cold interstellar medium with low temperatures to hot circumstellar envelopes where temperatures surge to several thousand kelvins. These factors collectively position acetylene as a crucial building block in the molecular diversification of organic molecules and solids present in space. This review comprehensively discusses the formation and expansion of carbon skeletons involving acetylene, ranging from the formation of simple molecules to the origination of the first aromatic ring and ultimately to the formation of nanosized carbon particles. Mechanisms pertinent to both hot environments, such as circumstellar envelopes, and cold environments, including molecular clouds and planetary atmospheres, are explored. In addition, this review contemplates the role of acetylene in the synthesis of prebiotic molecules. A distinct focus is accorded to the recent advancements and future prospects of research into catalytic processes involving acetylene molecules, which is a significant instrument in driving the evolution of carbon complexity in the Universe. The insights garnered from this review underscore the significance of acetylene in astrochemistry and potentially contribute to our understanding of the chemical evolution of the Universe.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Role of Acetylene in the Chemical Evolution of Carbon Complexity

Pentsak,

Murga,

Ananikov

2024

ACS Earth Space Chem.

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“…The challenging issue is to develop sustainable technologies for organic synthesis based on simple low-cost reagents connected to the industrial cycle. Acetylene is one of the most demanding examples in this regard due to its low price, outstanding diversity of reactions, and variety of pathways to different reagents . Incorporation into a sustainable carbon recycling route is one of the key advantages of acetylene .…”

Section: Introductionmentioning

confidence: 99%

Densely Packed Chemical Synthesis Equipment by 3D Spatial Design and Additive Manufacturing: Acetylene Generation Cartridge

Erokhin

Ananikov

2023

Org. Process Res. Dev.

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Preparation of and carrying out chemical reactions often require considerable laboratory space. Miniaturization of chemical equipment and reducing laboratory space requirements are an essential task to improve cost-efficiency, as well as increase safety and decrease potential risks. In this work, we discuss the miniaturization of laboratory equipment through the spatial optimization of functional parts. To demonstrate this, we have optimized the size of one of the most cumbersome processes in the lab, the generation of gases from solid sources. We have developed a ready-to-use acetylene generation cartridge with a high degree of functional filling of the internal space, which significantly compacts its dimensions. The cartridge was sealed upon three-dimensional (3D) printing, prepacked with the reagent, and found suitable for long-term storage. In addition to acetylene generation, built-in water trap channels and a drying compartment made it possible to obtain dried gas on the output of the cartridge. The cartridge showed high efficiency in the reactions for the synthesis of bis(arylthio)-substituted ethenes and butadienes. To expand the range of products based on acetylene, a procedure for the synthesis of 1,2-bis(alkylthio)ethenes was developed. The use of the cartridge allowed us to obtain target Z-ethenes with good yields and stereoselectivity.

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“…4 Furthermore, due to its accessibility and versatile reactivity, the alkyne motif has become a privileged synthon in synthetic chemistry. 5 Of the transformations involving alkynes, difunctionalization and coupling reactions of alkynes represent high-value synthetic approaches. The difunctionalization of an alkyne could simultaneously furnish two functional groups at vicinal positions in a single step.…”

Section: Introductionmentioning

confidence: 99%