User:Chloeczhou/Halogenated ether
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Halogenated ether are a subcategory of a larger group of chemicals known as ethers. An ether is an organic chemical that contains an ether group—an oxygen atom connected to two (substituted) alkyl groups. A good example of an ether is the solvent diethyl ether.[1] Examples of commonly used halogenated ethers include halothane, isoflurane, sevofluorane and desflurane.[2] Halogenated ethers differ from other ethers is as there is a substitution (halogenation) of one or more hydrogen atoms with a halogen atom. Halogen atoms include fluorine, chlorine, bromine, and iodine.[3]
While there are many toxicological dangers with these compounds, they can also be used as anesthetic agents, in polymers, and even as flame retardant.
Common Halogenated Ethers
[edit]| Halogenated Ether | Chemical Formula | Chemical Structure |
|---|---|---|
| Sevoflurane | C4H3F7O | |
| Isoflurane | C3H2ClF5O | |
| Desflurane | C3H2F6O | |
| Methoxyflurane | C3H4Cl2F2O | |
| Enflurane | C3H2ClF5O |
History
[edit]Until the 1950s an ideal inhaled anesthetic was yet to be found. Volatile substances like diethyl ether, which have severe risks of nausea, were used instead.[4] Diethyl ether had the unfortunate disadvantage of being extremely flammable, especially in the presence of enriched oxygen mixtures. Thus, many instances of fires and even explosions in operating rooms during surgery occurred.[5]
James Young Simpson, an obstetrics surgeon, used ether to help women relieve their labor pains. He quickly realized that ethers were no longer a viable option. Using the halogenated hydrocarbon, chloroform, Simpson and his friends decided to test this at a house party as a substitute inhalation agent. They woke from unconsciousness and were pleasantly surprised with the outcome. This was the first recorded, successful use of halogenated hydrocarbons as anesthetics. [4]
Eventually these compounds also made their demise. Halogenated ethers have the advantages of being non-flammable as well as less toxic than earlier general anesthetics. Halogenated ethers differ from other ethers because they contain at least one halogen atom in each molecule. Examples of halogenated ethers include the general anesthetics isoflurane, desflurane, and sevoflurane. However, not all halogenated ethers have anesthetic effects, and some compounds such as flurothyl do the opposite and have stimulant and convulsant effects.[2]
Uses in anesthesiology
[edit]Inhaled agents like diethyl ether are critical in anesthesia. Diethyl ether initially replaced non-flammable (but more toxic) halogenated hydrocarbons like chloroform and trichloroethylene. Halothane is a halogenated hydrocarbon anesthetic agent that was introduced into clinical practice in 1956. Due to its ease of use and improved safety profile with respect to organ toxicity, halothane quickly replaced chloroform and trichloroethylene.[6]
The anesthesia practice was significantly improved later in the 1950s with the introduction of halogenated ethers, like halothane, isoflurane, enflurane, and sevoflurane. Since its introduction in the 1980s, isoflurane has been widely used due to its decreased risk of hepatotoxicity and better hemodynamic stability when compared to halothane. The 1990s saw the development of sevoflurane, which was especially helpful in pediatric anesthesia because it provided even faster induction and recovery profiles.[7]
All inhalation anesthetics in current clinical use are halogenated ethers, except for halothane (which is a halogenated hydrocarbon or haloalkane), nitrous oxide, and xenon.[8]
Inhalation anesthetics are vaporized and mixed with other gases prior to their inhalation by the patient before or during surgery. These other gases always include oxygen or air, but may also include other gases such as nitrous oxide or helium. In most surgical situations, other drugs such as opiates are used for pain and skeletal muscle relaxants are used to cause temporary paralysis. Additional drugs such as midazolam may be used to produce amnesia during surgery. Although newer intravenous anesthetics (such as propofol) have increased the options of anesthesiologists, halogenated ethers remain a mainstay of general anesthesia [9].
Use in polymers
[edit]The perfluorinated epoxides are used as comonomers for the production of polytetrafluoroethylene.
When used as comonomers, they can alter the microstructure of PTFE, reducing crystallinity and improving flexibility and toughness. This makes the polymer more suitable for applications like seals and gaskets, which require resilience under stress. Furthermore, perfluorinated epoxides enable the tailoring of specific functional properties, such as low surface energy, which is essential for applications requiring non-stick or low-friction surfaces. [10]
Use as Flame retardant
[edit]Halogenated ethers play a significant role in enhancing the thermal stability and fire resistance of polymers. When applied to materials, they are effective in preventing items from catching fire because of the chemical's resistance to decomposition and effective flame suppression properties.
Most halogenated ethers contain bromine or chlorine. Brominated compounds are particularly effective because they release bromine radicals when exposed to heat. These radicals interrupt the combustion process by reacting with free radicals in the flame, thereby suppressing fire propagation. Chlorinated ethers can also function similarly by releasing chlorine radicals. Both types of halogens contribute to the flame-retardant properties, but brominated ethers are often favoured for their higher efficiency and lower required concentrations compared to their chlorinated counterparts [11].
Tetrabromobisphenol A bis(2,3-dibromopropyl) ether (TBBPA-DBPE) is an example, and is widely used in electronic casings and circuit boards due to its high efficiency in reducing flammability. TBBPA-DBPE is also a flame retardant in plastics, paper, and textiles, and as a plasticizer in adhesives and coatings [12].
Decabromodiphenyl ether (deca-BDE), a type of Polybrominated diphenyl ethers (PBDEs), was widely used in polystyrene, acrylonitrile butadiene styrene (ABS), flexible polyurethane foam, textile coatings, wire and cable insulation, electrical/electronic connectors, and other interior parts. PBDE is one of many halogenated flame retardants that are now are heavily regulated or banned in many regions because of their persistence, bioaccumulation, and potential toxicity [13]. Most industries are now transitioning to alternative, less hazardous flame retardants. However, because of the widespread use of these chemicals in many products, it is anticipated that they will continue to persist in the environment [14]
Toxicology of Halogenated Ethers
[edit]Respiratory Depression
[edit]Halogenated ethers can cause respiratory depression by reducing the body's response to carbon dioxide and hypoxia, which affects breathing rates and depth. Some, like desflurane and isoflurane, are also known for causing airway irritation, leading to coughing, breath-holding, or laryngospasm, particularly during inhalational induction of anesthesia. Sevoflurane, with minimal airway irritation, is generally preferred for induction, particularly in children or those with sensitive airways [15].
Environmental Effect
[edit]Greenhouse Gas Emissions
[edit]Halogenated ethers contribute to global warming as greenhouse gases. dCompounds like desflurane and isoflurane have high global warming potentials (GWP), which measure their heat-trapping abilities relative to carbon dioxide (CO₂). The GWP of a halogenated anesthetic is up to 2,000 times greater than CO2. The use of these anesthetics in healthcare is a significant contributor to hospital-related greenhouse gas emissions, leading to a growing focus on identifying lower-GWP alternatives or enhancing recovery and recycling technologies for anesthetic gases [16]
Persistence and Bioaccumulation
[edit]Due to their stability, halogenated ethers can persist in the atmosphere for years, contributing to their cumulative environmental footprint. These compounds do not readily degrade and thus remain in circulation long after their release, adding to the atmospheric burden of greenhouse gases. Although they are generally not bioaccumulative due to their high volatility and low tendency to dissolve in water or adhere to biological tissues, the persistent nature of these compounds raises concerns for long-term environmental effects, especially in areas surrounding healthcare facilities where they may be routinely released [17]
- ^ Schmitt, Laura; Hinxlage, Ilka; Cea, Pablo A.; Gohlke, Holger; Wesselborg, Sebastian (2021-02-13). "40 Years of Research on Polybrominated Diphenyl Ethers (PBDEs)—A Historical Overview and Newest Data of a Promising Anticancer Drug". Molecules. 26 (4): 995. doi:10.3390/molecules26040995. ISSN 1420-3049.
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- ^ a b Whalen, Francis X.; Bacon, Douglas R.; Smith, Hugh M. (2005-09-01). "Inhaled anesthetics: an historical overview". Best Practice & Research Clinical Anaesthesiology. Renaissance of Inhalational Anaesthesia. 19 (3): 323–330. doi:10.1016/j.bpa.2005.02.001. ISSN 1521-6896.
- ^ insideout (2015-04-27). "Understanding the Safety Risks of Diethyl Ether". VelocityEHS. Retrieved 2024-11-04.
- ^ "Halothane". go.drugbank.com. Retrieved 2024-11-04.
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- ^ Miller, Amanda L.; Theodore, Danny; Widrich, Jason (2024), "Inhalational Anesthetic", StatPearls, Treasure Island (FL): StatPearls Publishing, PMID 32119427, retrieved 2024-11-04
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- ^ Siegemund, Günter; Schwertfeger, Werner; Feiring, Andrew; Smart, Bruce; Behr, Fred; Vogel, Herward; McKusick, Blaine; Kirsch, Peer (2016-01-28). "Fluorine Compounds, Organic". Ullmann's Encyclopedia of Chemical Technology. Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA. pp. 1–56. doi:10.1002/14356007.a11_349.pub2. ISBN 978-3-527-30673-2.
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- ^ Knudsen, Gabriel A.; Hughes, Michael F.; Birnbaum, Linda S. (2019-02-01). "Dermal disposition of Tetrabromobisphenol A Bis(2,3-dibromopropyl) ether (TBBPA-BDBPE) using rat and human skin". Toxicology Letters. 301: 108–113. doi:10.1016/j.toxlet.2018.11.011. ISSN 0378-4274.
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{{cite journal}}: CS1 maint: unflagged free DOI (link) - ^ Wu, Qiong; Munschy, Catherine; Bodin, Nathalie; Vetter, Walter (2024-07-17). "Persistent and Bioaccumulative Halogenated Natural Products in Various Tropical Reef Fish Species from the Seychelles, Western Indian Ocean". Journal of Agricultural and Food Chemistry. 72 (28): 15643–15652. doi:10.1021/acs.jafc.4c03503. ISSN 1520-5118. PMID 38967173.