View source for C12–C14 alcohol glycidyl ether

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| ImageFile = Alkyl glycidyl ether.svg
| ImageSize = 180px
| ImageCaption = ''n'' = 10-12
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| IUPACName = 2-(dodecoxymethyl)oxirane;2-(tetradecoxymethyl)oxirane;2-(tridecoxymethyl)oxirane
| OtherNames = Alkyl glycidyl ether
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| Section1 = {{Chembox Identifiers
| CASNo = 68609-97-2
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| ChEMBL =
| ChemSpiderID = 22504671
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| InChI = 1S/C17H34O2.C16H32O2.C15H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-18-15-17-16-19-17;1-2-3-4-5-6-7-8-9-10-11-12-13-17-14-16-15-18-16;1-2-3-4-5-6-7-8-9-10-11-12-16-13-15-14-17-15/h17H,2-16H2,1H3;16H,2-15H2,1H3;15H,2-14H2,1H3
| InChIKey = CKNWGKWITWNVEY-UHFFFAOYSA-N
| KEGG =
| MeSHName =
| PubChem = 56846565
| SMILES = CCCCCCCCCCCCCCOCC1CO1.CCCCCCCCCCCCCOCC1CO1.CCCCCCCCCCCCOCC1CO1
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| Section2 = {{Chembox Properties
| C=48 | H=96 | O=6
| MolarMass = 769.3 g/mol
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| Section3 = {{Chembox Hazards
| GHS_ref=<ref>{{cite web |title=Dodecyl and tetradecyl glycidyl ethers |url=https://pubchem.ncbi.nlm.nih.gov/compound/56846565#section=Safety-and-Hazards |website=pubchem.ncbi.nlm.nih.gov |access-date=12 April 2022 |language=en}}</ref>
| GHSPictograms = {{GHS07}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|315|317}}
| PPhrases = {{P-phrases|261|264|272|280|302+352|321|332+313|333+313|362|363|501}}
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'''C12-C14 alcohol glycidyl ether''' ('''AGE''') is an organic chemical in the glycidyl ether family.<ref>{{Cite web |title=Alkyl (C12-C14) glycidyl ether {{!}} 68609-97-2 |url=https://www.chemicalbook.com/ChemicalProductProperty_EN_CB5123061.htm |access-date=2022-04-10 |website=www.chemicalbook.com}}</ref> It is a mixture of mainly 12 and 14 carbon chain alcohols, also called [[fatty alcohol]]s that have been glycidated. It is an industrial chemical used as a surfactant but primarily for [[epoxy]] resin [[viscosity]] reduction.<ref>{{Cite journal |last1=Jagtap |first1=Ameya Rajendra |last2=More |first2=Aarti |date=2022-08-01 |title=Developments in reactive diluents: a review |url=https://doi.org/10.1007/s00289-021-03808-5 |journal=Polymer Bulletin |language=en |volume=79 |issue=8 |pages=5667–5708 |doi=10.1007/s00289-021-03808-5 |s2cid=235678040 |issn=1436-2449}}</ref> It has the [[CAS Registry Number|CAS number]] 68609-97-2 but the [[International Union of Pure and Applied Chemistry|IUPAC]] name is more complex as it is a mixture and is 2-(dodecoxymethyl)oxirane;2-(tetradecoxymethyl)oxirane;2-(tridecoxymethyl)oxirane.<ref>{{Cite web |last=PubChem |title=Dodecyl and tetradecyl glycidyl ethers |url=https://pubchem.ncbi.nlm.nih.gov/compound/56846565 |access-date=2022-04-12 |website=pubchem.ncbi.nlm.nih.gov |language=en}}</ref> Other names include dodecyl and tetradecyl glycidyl ethers and alkyl (C12-C14) glycidyl ether.
==Manufacture==
A fatty alcohol mixture rich in C12-C14 alcohols is placed in a reactor with a [[Lewis acid]] [[catalyst]]. Then [[epichlorohydrin]] is added slowly to control [[Exothermic process|exotherm]] which results in the formation of the [[halohydrin]]s.<ref>{{Cite web |date=November 1992 |title=Process for the preparation of glycidyl ethers- US Patent 5162547 |url=https://patentimages.storage.googleapis.com/be/ad/1f/c3b9622c714a8b/US5162547.pdf}}</ref> This is followed by a caustic [[dehydrochlorination]], to form C12-C14 alcohol glycidyl ether.<ref>{{Cite web |last=SJÖVOLD |first=HENRICK |date=2015 |title=Solvent-Free Synthesis of Glycidyl Ethers : Investigating Factors Influencing the Yield of Alkyl Glycidyl Ethers Master of Science Thesis |url=https://publications.lib.chalmers.se/records/fulltext/218842/218842.pdf |website=Chalmers University Sweden}}</ref>
The waste products are water and sodium chloride and excess caustic soda.<ref>{{Cite web |title=Preparation method of alkyl glycidyl ether - Patent CN-113429367-A - PubChem |url=https://pubchem.ncbi.nlm.nih.gov/patent/CN-113429367-A |access-date=2022-04-12 |website=pubchem.ncbi.nlm.nih.gov}}</ref> One of the quality control tests would involve measuring the [[Epoxy value]] by determination of the epoxy equivalent weight.
==Uses==
As an [[epoxy]] modifier it is classed as an epoxy [[reactive diluent]].<ref>{{Citation |last=Monte |first=Salvatore J. |title=Diluents and viscosity modifiers for epoxy resins |date=1998 |url=https://doi.org/10.1007/978-94-011-5862-6_24 |work=Plastics Additives: An A-Z reference |series=Polymer Science and Technology Series |volume=1 |pages=211–216 |editor-last=Pritchard |editor-first=Geoffrey |place=Dordrecht |publisher=Springer Netherlands |language=en |doi=10.1007/978-94-011-5862-6_24 |isbn=978-94-011-5862-6 |access-date=2022-03-29}}</ref> It is one of a family of glycidyl ethers available used for viscosity reduction of [[epoxy]] resins.<ref>{{Cite journal |last1=Ali |first1=M. |last2=Hammami |first2=A. |date=July 2005 |title=Experimental modeling of the cure behavior of a formulated blend of DGEBA epoxy and C12-C14 glycidyl ether as a reactive diluent |url=https://onlinelibrary.wiley.com/doi/10.1002/pc.20131 |journal=Polymer Composites |language=en |volume=26 |issue=5 |pages=593–603 |doi=10.1002/pc.20131 |issn=0272-8397}}</ref> These are then further formulated into [[coating]]s, [[sealant]]s, [[adhesive]]s, and [[elastomer]]s.<ref>Howarth G.A "Synthesis of a legislation compliant corrosion protection coating system based on urethane, oxazolidine and waterborne epoxy technology" pages 23,24,39 Master of Science Thesis April 1997 Imperial College London</ref><ref>{{Citation |last=Monte |first=Salvatore J. |title=Diluents and viscosity modifiers for epoxy resins |date=1998 |url=https://doi.org/10.1007/978-94-011-5862-6_24 |work=Plastics Additives: An A-Z reference |series=Polymer Science and Technology Series |volume=1 |pages=211–216 |editor-last=Pritchard |editor-first=Geoffrey |place=Dordrecht |publisher=Springer Netherlands |language=en |doi=10.1007/978-94-011-5862-6_24 |isbn=978-94-011-5862-6 |access-date=2022-04-12}}</ref> Resins with this diluent tend to show improved workability.<ref>{{Cite journal |last1=Ozeren Ozgul |first1=Eren |last2=Ozkul |first2=M. Hulusi |date=2018-01-15 |title=Effects of epoxy, hardener, and diluent types on the workability of epoxy mixtures |url=https://www.sciencedirect.com/science/article/pii/S095006181732038X |journal=Construction and Building Materials |language=en |volume=158 |pages=369–377 |doi=10.1016/j.conbuildmat.2017.10.008 |issn=0950-0618}}</ref> It is also used to synthesize other molecules.<ref>{{Cite journal |last1=Urata |first1=Kouichi |last2=Takaishi |first2=Naotake |date=September 1994 |title=The alkyl glycidyl ether as synthetic building blocks |url=http://doi.wiley.com/10.1007/BF02542274 |journal=Journal of the American Oil Chemists' Society |language=en |volume=71 |issue=9 |pages=1027–1033 |doi=10.1007/BF02542274|s2cid=96776835 }}</ref><ref>{{Cite journal |last1=Verkoyen |first1=Patrick |last2=Frey |first2=Holger |date=August 2020 |title=Long-Chain Alkyl Epoxides and Glycidyl Ethers: An Underrated Class of Monomers |journal=Macromolecular Rapid Communications |language=en |volume=41 |issue=15 |pages=2000225 |doi=10.1002/marc.202000225 |pmid=32567153 |issn=1022-1336|doi-access=free }}</ref> The use of the diluent does effect mechanical properties and microstructure of epoxy resins.<ref>{{Cite journal |last1=Khalina |first1=Morteza |last2=Beheshty |first2=Mohammad Hosain |last3=Salimi |first3=Ali |date=2019-08-01 |title=The effect of reactive diluent on mechanical properties and microstructure of epoxy resins |url=https://doi.org/10.1007/s00289-018-2577-6 |journal=Polymer Bulletin |language=en |volume=76 |issue=8 |pages=3905–3927 |doi=10.1007/s00289-018-2577-6 |s2cid=105389177 |issn=1436-2449}}</ref><ref>{{Cite journal |last1=Pastarnokienė |first1=Liepa |last2=Jonikaitė-Švėgždienė |first2=Jūratė |last3=Lapinskaitė |first3=Neringa |last4=Kulbokaitė |first4=Rūta |last5=Bočkuvienė |first5=Alma |last6=Kochanė |first6=Tatjana |last7=Makuška |first7=Ričardas |date=2023-07-01 |title=The effect of reactive diluents on curing of epoxy resins and properties of the cured epoxy coatings |url=https://doi.org/10.1007/s11998-022-00737-4 |journal=Journal of Coatings Technology and Research |language=en |volume=20 |issue=4 |pages=1207–1221 |doi=10.1007/s11998-022-00737-4 |s2cid=256749849 |issn=1935-3804}}</ref>
==Toxicology==
The toxicology is well known, and it is classed as a skin irritant.<ref>{{Cite web |title=C&L Inventory |url=https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/100343 |access-date=2022-04-12 |website=echa.europa.eu |language=en-GB}}</ref>
==See also==
* [[Epoxide]]
* [[Glycidol]]
==References==
{{Reflist}}
==Further reading==
* {{Cite book|url=https://www.worldcat.org/oclc/182890|title=Epoxy resin technology.|date=1968|publisher=Interscience Publishers|others=Paul F. Bruins, Polytechnic Institute of Brooklyn|isbn=0-470-11390-1|location=New York|oclc=182890}}
* {{Cite book|last=Flick|first=Ernest W.|url=https://www.worldcat.org/oclc/915134542|title=Epoxy resins, curing agents, compounds, and modifiers : an industrial guide|date=1993|isbn=978-0-8155-1708-5|location=Park Ridge, NJ|oclc=915134542}}
* {{Cite book|last=Lee|first=Henry|url=https://www.worldcat.org/oclc/311631322|title=Handbook of epoxy resins|date=1967|publisher=McGraw-Hill|others=Kris Neville|isbn=0-07-036997-6|edition=[2nd, expanded work]|location=New York|oclc=311631322}}
* {{Cite web|url=http://nmt.edu/academics/mtls/faculty/mccoy/docs2/chemistry/DowEpoxyResins.pdf|title=Dow Epoxy Resins}}
==External websites==
* [https://nagaseamerica.com/product/denacol-aliphatic-epoxies-5/ Denacol epoxy diluent range]
* [https://olinepoxy.com/products/reactive-diluents/    Reactive Diluents – Olin Epoxy]
* [https://www.hexion.com/en-au/chemistry/epoxy-resins-curing-agents-modifiers/functional-modifiers  Hexion Epoxy Functional Modifiers]
* [https://www.cargill.com/bioindustrial/chemmod-reactive-diluents Cargill Reactive diluents]
{{Glycidyl ethers}}
[[Category:Glycidyl ethers]]
[[Category:Reactive diluents]]
{{DEFAULTSORT:C12-C14 alcohol glycidyl ether}}