Polyethylene glycol
Names | |
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IUPAC names
poly(oxyethylene) {structure-based},
poly(ethylene oxide) {source-based}[1] | |
Other names
Kollisolv, Carbowax, GoLYTELY, GlycoLax, Fortrans, TriLyte, Colyte, Halflytely, macrogol, MiraLAX, MoviPrep
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Identifiers | |
Abbreviations | PEG |
ChEMBL | |
ChemSpider |
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ECHA InfoCard
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100.105.546 |
E number | E1521 (additional chemicals) |
UNII | |
CompTox Dashboard (EPA)
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Properties | |
C2nH4n+2On+1 | |
Molar mass | 44.05n + 18.02 g/mol |
Density | 1.125[2] |
Pharmacology | |
A06AD15 (WHO) | |
Hazards | |
Flash point | 182–287 °C; 360–549 °F; 455–560 K |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Polyethylene glycol (PEG;
Uses
Medical uses
- Pharmaceutical-grade PEG is used as an excipient in many pharmaceutical products, in oral, topical, and parenteral dosage forms.[4]
- PEG is the basis of a number of Miralax) is the generic name for polyethylene glycol used as a laxative. The name may be followed by a number which represents the average molecular weight (e.g. macrogol 3350, macrogol 4000 or macrogol 6000).
- The possibility that PEG could be used to fuse axons is being explored by researchers studying peripheral nerve and spinal cord injury.[5]
- An example of PEG hydrogels (see Biological uses section) in a therapeutic has been theorized by Ma et al. They propose using the hydrogel to address periodontitis (gum disease) by encapsulating stem cells in the gel that promote healing in the gums.[7] The gel with encapsulated stem cells was to be injected into the site of disease and crosslinked to create the microenvironment required for the stem cells to function.
- PEGylation of adenoviruses for gene therapy can help prevent adverse reactions due to pre-existing adenovirus immunity.[8]
- A
Chemical uses
- Polyethylene glycol is also commonly used as a polar stationary phase for gas chromatography, as well as a heat transfer fluid in electronic testers.
- PEG is frequently used to preserve waterlogged wood and other organic artifacts that have been salvaged from underwater archaeological contexts, as was the case with the warship Vasa in Stockholm,[13] and similar cases. It replaces water in wooden objects, making the wood dimensionally stable and preventing warping or shrinking of the wood when it dries.[5] In addition, PEG is used when working with green wood as a stabilizer, and to prevent shrinkage.[14]
- PEG has been used to preserve the painted colors on Terracotta Warriors unearthed at a UNESCO World Heritage site in China.[15] These painted artifacts were created during the Qin Shi Huang (first emperor of China) era. Within 15 seconds of the terra-cotta pieces being unearthed during excavations, the lacquer beneath the paint begins to curl after being exposed to the dry Xi'an air. The paint would subsequently flake off in about four minutes. The German Bavarian State Conservation Office developed a PEG preservative that when immediately applied to unearthed artifacts has aided in preserving the colors painted on the pieces of clay soldiers.[16]
- PEG is often used (as an internal calibration compound) in mass spectrometry experiments, with its characteristic fragmentation pattern allowing accurate and reproducible tuning.
- PEG derivatives, such as narrow range ethoxylates, are used as surfactants.
- PEG has been used as the hydrophilic block of copolymers used to create some polymersomes.[17]
- PEG is a component of the propellent used in UGM-133M Trident II Missiles, in service with the United States Navy.[18]
Biological uses
- An example study was done using PEG-diacrylate hydrogels to recreate vascular environments with the encapsulation of endothelial cells and macrophages. This model furthered vascular disease modeling and isolated macrophage phenotype's effect on blood vessels.[19]
- PEG is commonly used as a crowding agent in in vitro assays to mimic highly crowded cellular conditions.
- PEG is commonly used as a X-ray diffractionof protein crystals can reveal the atomic structure of the proteins.
- PEG is used to fuse two different types of cells, most often B-cells and myelomas in order to create hybridomas. César Milstein and Georges J. F. Köhler originated this technique, which they used for antibody production, winning a Nobel Prize in Physiology or Medicine in 1984.[5]
- In microbiology, PEG precipitation is used to concentrate viruses. PEG is also used to induce complete fusion (mixing of both inner and outer leaflets) in liposomes reconstituted in vitro.
- Gene therapy vectors (such as viruses) can be PEG-coated to shield them from inactivation by the immune system and to de-target them from organs where they may build up and have a toxic effect.[23] The size of the PEG polymer has been shown to be important, with larger polymers achieving the best immune protection.
- PEG is a component of
- In
- When working with phenol in a laboratory situation, PEG 300 can be used on phenol skin burns to deactivate any residual phenol.[27]
- In biophysics, polyethylene glycols are the molecules of choice for the functioning ion channels diameter studies, because in aqueous solutions they have a spherical shape and can block ion channel conductance.[28][29]
Commercial uses
- PEG is the basis of many cetomacrogol) and personal lubricants.
- PEG is used in a number of toothpastes[5] as a dispersant. In this application, it binds water and helps keep xanthan gum uniformly distributed throughout the toothpaste.
- PEG is under investigation for use in body armor, and in tattoos to monitor diabetes.[30][31]
- Polymer segments derived from PEG polyols impart flexibility to polyurethanes for applications such as elastomeric fibers (spandex) and foamcushions.
- In low- as an ink solvent and lubricant for the print heads.
- PEG is used as an anti-foaming agent in food and drinks
Industrial uses
- A
- Dimethyl ethers of PEG are the key ingredient of Selexol, a solvent used by coal-burning, integrated gasification combined cycle (IGCC) power plants to remove carbon dioxide and hydrogen sulfide from the syngas stream.
- PEG has been used as the gate insulator in an electric double-layer transistor to induce superconductivity in an insulator.[36]
- PEG is used as a polymer host for solid polymer electrolytes. Although not yet in commercial production, many groups around the globe are engaged in research on solid polymer electrolytes involving PEG, with the aim of improving their properties, and in permitting their use in batteries, electro-chromic display systems, and other products in the future.
- PEG is injected into industrial processes to reduce foaming in separation equipment.
- PEG is used as a binder in the preparation of technical ceramics.[37]
- PEG was used as an additive to silver halide photographic emulsions.
Entertainment uses
- PEG is used to extend the size and durability of very large soap bubbles.
- PEG is the main ingredient in many personal lubricants.[citation needed] (Not to be confused with propylene glycol.)
- PEG is the main ingredient in the paint (known as "fill") in paintballs.
Health effects
PEG is considered biologically inert and safe by the U.S.
However, a growing body of evidence shows the existence of a detectable level of anti-PEG
Available forms and nomenclature
PEG, PEO, and POE refer to an oligomer or polymer of ethylene oxide. The three names are chemically synonymous, but historically PEG is preferred in the biomedical field, whereas PEO is more prevalent in the field of polymer chemistry. Because different applications require different polymer chain lengths, PEG has tended to refer to oligomers and polymers with a molecular mass below 20,000 g/mol, PEO to polymers with a molecular mass above 20,000 g/mol, and POE to a polymer of any molecular mass.[41] PEGs are prepared by polymerization of ethylene oxide and are commercially available over a wide range of molecular weights from 300 g/mol to 10,000,000 g/mol.[42]
PEG and PEO are liquids or low-melting solids, depending on their
PEGs are also available with different geometries.
- Branched PEGs have three to ten PEG chains emanating from a central core group.
- Star PEGs have 10 to 100 PEG chains emanating from a central core group.
- Comb PEGs have multiple PEG chains normally grafted onto a polymer backbone.
The numbers that are often included in the names of PEGs indicate their average molecular weights (e.g. a PEG with n = 9 would have an average molecular weight of approximately 400
PEG is soluble in water, methanol, ethanol, acetonitrile, benzene, and dichloromethane, and is insoluble in diethyl ether and hexane. It is coupled to hydrophobic molecules to produce non-ionic surfactants.[43]
PEG and related polymers (PEG phospholipid constructs) are often sonicated when used in biomedical applications. However, as reported by Murali et al., PEG is very sensitive to sonolytic degradation and PEG degradation products can be toxic to mammalian cells. It is, thus, imperative to assess potential PEG degradation to ensure that the final material does not contain undocumented contaminants that can introduce artifacts into experimental results.[44]
PEGs and methoxypolyethylene glycols are manufactured by
Production
The production of polyethylene glycol was first reported in 1859. Both
- HOCH2CH2OH + n(CH2CH2O) → HO(CH2CH2O)n+1H
Depending on the catalyst type, the mechanism of
Polyethylene oxide, or high-molecular-weight polyethylene glycol, is synthesized by
Alkaline catalysts such as sodium hydroxide (NaOH), potassium hydroxide (KOH), or sodium carbonate (Na2CO3) are used to prepare low-molecular-weight polyethylene glycol.[47]
Safety
PEO's have "very low singledose oral toxicity", on the order of tens of grams per kg body weight (oral).[3] Because of its low toxicity, PEO is used in a variety of edible products.[48] The polymer is used as a lubricating coating for various surfaces in aqueous and non-aqueous environments.[49]
The precursor to PEGs is ethylene oxide, which is hazardous.[50] Ethylene glycol and its ethers are nephrotoxic if applied to damaged skin.[51]
See also
- Ethylene
- Propylene glycol
- Monoethylene glycol
- Diethylene glycol
- PEGylation
- PEG-PVA
- Lauryl methyl gluceth-10 hydroxypropyl dimonium chloride
- Movicol
- Polyethylene glycol propylene glycol cocoates
- Lysozyme PEGylation
References
- .
- ^ "Poly(ethylene glycol)". ChemSrc. 7 January 2020.
- ^ ISBN 978-3527306732.
- ^ "Polyethylene Glycol as Pharmaceutical Excipient". pharmaceutical.basf.com. Retrieved 27 April 2021.
- ^ a b c d e f Kean S (2017). "Chemical Hope". Distillations. 2 (4): 5. Retrieved 22 March 2018.
- ^ "Polyethyleneglycol (PEG 4000 ) | Laxolite | Medical Dialogues". Medical Dialogues. 19 January 2021. Retrieved 19 January 2021.
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- ^ Bostock N (9 December 2020). "MHRA warning after allergic reactions in NHS staff given COVID-19 vaccine". GP. Archived from the original on 9 December 2020. Retrieved 9 December 2020.
- ^ "Pfizer-BioNTech COVID-19 vaccine: Health Canada recommendations for people with serious allergies". Health Canada. 12 December 2020.
- ^ Furtula A, Jordans F (21 December 2020). "EU regulator gives conditional approval to Pfizer-BioNTech COVID-19 vaccine". The Globe and Mail Inc. Reuters.
- ISBN 91-7486-581-1.
- ^ "Anti-Freeze is Not a Green Wood Stabilizer – Buzz Saw". The Rockler Blog. 2 May 2006. Archived from the original on 17 January 2022. Retrieved 30 November 2012.
- ^ Reiffert S (18 March 2015). "Conservators preserve the paint layers of the Terracotta Army". tum.de. Technische Universität München. Archived from the original on 22 December 2015. Retrieved 19 December 2015.
- National Geographic. 221 (6): 74–87.
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- ^ Johnson T (21 April 2004). "Army Scientists, Engineers develop Liquid Body Armor".
- ^ "Tattoo to monitor diabetes". BBC News. 1 September 2002.
- ^ US Government – Food and Drug Agency "Food Additive Status List". Food and Drug Administration. Retrieved 2 May 2017.
- ^ "Codex Alimentarius". codexalimentarius.net. Archived from the original on 7 January 2012.
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: CS1 maint: unfit URL (link) - ^ "Current EU approved additives and their E Numbers". UK Government – Food Standards Agency. Retrieved 21 October 2010.
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- ^ For example, in the online catalog Archived 29 December 2006 at the Wayback Machine of Scientific Polymer Products, Inc., poly(ethylene glycol) molecular weights run up to about 20,000, while those of poly(ethylene oxide) have six or seven digits.
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- ISBN 9780824783846. Retrieved 17 July 2017.
- ^ Polyethylene glycol, Chemindustry.ru
- ^ "PEG 4000, 6000, 8000, 12000 | Polyethylene glycol". www.venus-goa.com. Retrieved 19 January 2023.
- ^ Sheftel VO (2000). Indirect Food Additives and Polymers: Migration and Toxicology. CRC. pp. 1114–1116. Archived from the original on 9 August 2007. Retrieved 22 August 2007.
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- ^ Center for Food Safety and Applied Nutrition. "Potential Contaminants - 1,4-Dioxane A Manufacturing Byproduct". fda.gov. Retrieved 26 May 2017.
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