Castor oil glycidyl ether

Last updated
Castor oil glycidyl ether
Castor oil glycidyl ether.svg
Names
IUPAC name
2,3-bis[12-(oxiran-2-ylmethoxy)octadec-9-enoyloxy]propyl 12-(oxiran-2-ylmethoxy)octadec-9-enoate
Identifiers
3D model (JSmol)
EC Number
  • 616-085-8
PubChem CID
  • InChI=1S/C66H116O12/c1-4-7-10-31-40-57(70-49-60-52-73-60)43-34-25-19-13-16-22-28-37-46-64(67)76-55-63(78-66(69)48-39-30-24-18-15-21-27-36-45-59(42-33-12-9-6-3)72-51-62-54-75-62)56-77-65(68)47-38-29-23-17-14-20-26-35-44-58(41-32-11-8-5-2)71-50-61-53-74-61/h25-27,34-36,57-63H,4-24,28-33,37-56H2,1-3H3
    Key: ZFJYZDDXGKWNCH-UHFFFAOYSA-N
  • CCCCCCC(CC=CCCCCCCCC(=O)OCC(COC(=O)CCCCCCCC=CCC(CCCCCC)OCC1CO1)OC(=O)CCCCCCCC=CCC(CCCCCC)OCC2CO2)OCC3CO3
Properties
C66H16O12
Molar mass 1101.6 g/mol
Hazards
GHS labelling: [1]
GHS-pictogram-exclam.svg
Warning
H315, H317
P261, P264, P264+P265, P271, P272, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P333+P313, P337+P317, P362+P364, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Castor oil glycidyl ether is a liquid organic chemical in the glycidyl ether family. It is sometimes called castor oil triglycidyl ether. It has the theoretical formula C66H116O12. There are two CAS numbers in use, 14228-73-0 and 74398-71-3. [2] The IUPAC name is 2,3-bis[[(E)-12-(oxiran-2-ylmethoxy)octadec-9-enoyl]oxy]propyl (E)-12-(oxiran-2-ylmethoxy)octadec-9-enoate. [3] A key use is acting as a modifier for epoxy resins as a reactive diluent that adds flexibility and improved mechanical properties. [4] [5]

Contents

Manufacture

It is made by glycidation of castor oil which is a vegetable oil. Castor oil and epichlorohydrin are reacted in the presence of a Lewis acid catalyst to form halohydrin: each hydroxyl group of the triol reacts with an epoxide on epichlorohydrin. This process is followed neutralizing the catalyst with a small amount of sodium hydroxide and then adding a large excess of epichlorohydrin as solvent. To re-form the epoxide rings in a dehydrochlorination reaction, solid sodium hydroxide flake is used rather than a solution. On completion the epichlorohydrin is recovered and the product cleaned up. [6] One of the quality control tests would involve measuring the epoxy value by determination of the epoxy equivalent weight.

Uses

A 2018 study concluded that its use as a flexiblizing agent as well as an epoxy diluent has application in the aviation field. [7] Poly(propylene glycol) diglycidyl ether may also be used for the same application but has the perceived disadvantage that it is petroleum based rather than renewable plant based like the castor oil glycidyl ether. A patent application shows it may also be used as a co-reactant-surfactant in herbicide production. [8] As the molecule has 3 oxirane functionalities, a key use is modifying and reducing the viscosity of epoxy resins. [9] [10] These reactive diluent modified epoxy resins may then be further formulated into CASE applications: coatings, [11] adhesives, [12] sealants, [13] elastomers. It is also used in composite production. [14] It produces epoxy coatings with high impact resistance. [15] Polymer systems with shape memory may also be produced with this particular molecule. [16] The use of the diluent does effect mechanical properties and microstructure of epoxy resins. [17] [18] Production of biocompatible materials is also possible and the material is often classed as a renewable resource. [19] [20] It has also found use in oil well petroleum recovery. [21]

See also

Related Research Articles

<span class="mw-page-title-main">Epoxy</span> Type of material

Epoxy is the family of basic components or cured end products of epoxy resins. Epoxy resins, also known as polyepoxides, are a class of reactive prepolymers and polymers which contain epoxide groups. The epoxide functional group is also collectively called epoxy. The IUPAC name for an epoxide group is an oxirane.

<span class="mw-page-title-main">Bisphenol A diglycidyl ether</span> Chemical compound

Bisphenol A diglycidyl ether is an organic compound and is a liquid epoxy resin. The compound is a colorless viscous liquid. It is a key component of many epoxy resin formulations. Addition of further Bisphenol A and a catalyst and heat can produce Bisphenol A glycidyl ether epoxy resins of higher molecular weight that are solid.

n-Butyl glycidyl ether is an industrial chemical used in adhesives, sealants, and as a paint or coating additive. It is principally used to reduce the viscosity of epoxy resin systems.

<span class="mw-page-title-main">Reactive diluent</span>

Reactive diluents are substances which reduce the viscosity of a lacquer or resin for processing and become part of the lacquer or coating during its subsequent curing via copolymerization. A non-reactive diluent would be a solvent or plasticizer.

Epoxy value derives from the Epoxy equivalent weight (EEW) or Weight Per Epoxide (WPE) and is a measure of the epoxy content of an epoxy resin or epoxy reactive diluent, or glycidyl ether. This is an important parameter as it allows determination of the correct mix ratio of an epoxy system with a curing agent. The epoxide equivalent weight is usually measured first and done by titration. The standard test method is ASTM D1652 though this has been modified by certain states of the USA. The epoxy equivalent weight (EEW) maybe defined as: the number of grams of epoxy resin required to give 1 mole of epoxy groups. The epoxy value is defined as the number of moles of epoxy group per 100g resin.

2-Ethylhexyl glycidyl ether is a liquid organic molecule with formula C11H22O2 an industrial chemical used to reduce the viscosity of epoxy resins. These are then used in adhesives, sealants, and paints or coatings. It has the CAS Registry Number of 2461-15-6. It has the IUPAC name of 2-(2-ethylhexoxymethyl)oxirane. It also finds use in other polymer based applications.

<i>o</i>-Cresyl glycidyl ether Chemical compound

o-Cresyl glycidyl ether (ortho-cresyl glycidyl ether, o-CGE) is a liquid aromatic organic chemical compound and chemically a glycidyl ether. It has the formula C10H12O2 and the CAS Registry Number 2210-79-9. It is one of a number of glycidyl ethers available commercially that are used to reduce the viscosity of epoxy resins. These are then further used in coatings, sealants, adhesives and elastomers.

Neopentyl glycol diglycidyl ether (NPGDGE) is an organic chemical in the glycidyl ether family. It is aliphatic and a colorless liquid. It has the formula C11H20O4 and the CAS registry number of 17557-23-2. It has two oxirane groups per molecule. Its principle use is in modifying epoxy resins.

1,4-Butanediol diglycidyl ether (B14DODGE) is an organic chemical in the glycidyl ether family. It is aliphatic and a colorless liquid. It has two epoxide (oxirane) groups per molecule. Its main use is in modifying epoxy resins especially viscosity reduction.

1,6-Hexanediol diglycidyl ether is an organic chemical in the glycidyl ether family. It is an aliphatic compound that is a colorless liquid. It has two epoxide (oxirane) groups per molecule. Its main use is in modifying epoxy resins especially viscosity reduction whilst flexibilizing. It is REACH registered.

1,4-Cyclohexanedimethanol diglycidyl ether is an organic chemical in the glycidyl ether family. Its formula is C14H24O4 and the IUPAC name is 2-[[4-(oxiran-2-ylmethoxymethyl)cyclohexyl]methoxymethyl]oxirane. It has the CAS number of 14228-73-0 and is REACH registered in Europe. An industrial chemical, a key use is in the reduction of the viscosity of epoxy resin systems functioning as a reactive diluent.

<span class="mw-page-title-main">C12–C14 alcohol glycidyl ether</span> Chemical compound

C12-C14 alcohol glycidyl ether (AGE) is an organic chemical in the glycidyl ether family. It is a mixture of mainly 12 and 14 carbon chain alcohols, also called fatty alcohols that have been glycidated. It is an industrial chemical used as a surfactant but primarily for epoxy resin viscosity reduction. It has the CAS number 68609-97-2 but the IUPAC name is more complex as it is a mixture and is 2-(dodecoxymethyl)oxirane;2-(tetradecoxymethyl)oxirane;2-(tridecoxymethyl)oxirane. Other names include dodecyl and tetradecyl glycidyl ethers and alkyl (C12-C14) glycidyl ether.

<span class="mw-page-title-main">Trimethylolpropane triglycidyl ether</span> Chemical compound

Trimethylolpropane triglycidyl ether (TMPTGE) is an organic chemical in the glycidyl ether family. It has the formula C15H26O6 and the IUPAC name is 2-[2,2-bis(oxiran-2-ylmethoxymethyl)butoxymethyl]oxirane, and the CAS number 3454-29-3. It also has another CAS number of 30499-70-8 A key use is as a modifier for epoxy resins as a reactive diluent.

<span class="mw-page-title-main">C12–C13 alcohol glycidyl ether</span> Chemical compound

C12-C13 alcohol glycidyl ether is a mixture of organic chemicals in the glycidyl ether family. It is a mixture of mainly 12 and 13 carbon chain alcohols, also called fatty alcohols that have been glycidated. It is an industrial chemical used as a surfactant but primarily for epoxy resin viscosity reduction. It has the CAS number 120547-52-6.

<span class="mw-page-title-main">Trimethylolethane triglycidyl ether</span> Chemical compound

Trimethylolethane triglycidyl ether (TMETGE) is an organic chemical in the glycidyl ether family. It has the formula C14H24O6 and the IUPAC name is 2-({2-methyl-3-[(oxiran-2-yl)methoxy]-2-{[(oxiran-2-yl)methoxy]methyl}propoxy}methyl)oxirane. The CAS number is 68460-21-9. A key use is as a modifier for epoxy resins as a reactive diluent.

<span class="mw-page-title-main">Poly(propylene glycol) diglycidyl ether</span> Chemical compound

Poly(propylene glycol) diglycidyl ether (PPGDGE) is an organic chemical in the glycidyl ether family. There are a number of variations depending on the starting molecular weight of the polypropylene glycol. They have the formula (C3H6O)n.C6H10O3 and the IUPAC name is Poly[oxy(methyl-1,2-ethanediyl)],a-(2-oxiranylmethyl)-w-(2-oxiranylmethoxy)- A key use is as a modifier for epoxy resins as a reactive diluent and flexibilizer. It is REACH registered.

<span class="mw-page-title-main">Diethylene glycol diglycidyl ether</span> Chemical compound

Diethylene glycol diglycidyl ether (DEGDGE) is an organic chemical in the glycidyl ether family with the formula C10H18O5.. The oxirane functionality makes it useful as a reactive diluent for epoxy resin viscosity reduction.

<span class="mw-page-title-main">Diglycidyl resorcinol ether</span> Chemical compound

Diglycidyl resorcinol ether, also called Resorcinol diglycidyl ether (RDGE) is a liquid aromatic organic chemical compound and chemically a glycidyl ether.

<span class="mw-page-title-main">Phenyl glycidyl ether</span> Chemical compound

Phenyl glycidyl ether, is a liquid aromatic organic chemical in the glycidyl ether class of compounds. It has the formula C9H10O2. It has the CAS Registry Number 122-60-1 and the IUPAC name of 2-(phenoxymethyl)oxirane. A key use is in the viscosity reduction of epoxy resin systems. It is REACH registered and on EINECS under the name 2,3-epoxypropyl phenyl ether.

<span class="mw-page-title-main">Diglycidyl aniline</span> Chemical compound

Diglycidyl aniline is an aromatic organic chemical in the glycidyl compound family. It is used to reduce the viscosity of epoxy resin systems. It has the empirical formula C12H15NO2 and the IUPAC name is N,N-bis(oxiran-2-ylmethyl)aniline. The CAS number is 2095-06-9. It is REACH registered in Europe with the EC number 218-259-5. A key use is in the viscosity reduction of epoxy resin systems functioning as a reactive diluent.

References

  1. ↑ "Homopolymer of glyceryl triester with 12-glycidyl-9-octadecenoic acid". pubchem.ncbi.nlm.nih.gov. Retrieved 20 April 2022.
  2. ↑ "CASTOR OIL GLYCIDYL ETHER | 74398-71-3". www.chemicalbook.com. Retrieved 2022-04-18.
  3. ↑ PubChem. "Castor oil glycidyl ether". pubchem.ncbi.nlm.nih.gov. Retrieved 2022-04-19.
  4. ↑ Fu, Qinghe; Tan, Jihuai; Han, Changhao; Zhang, Xiaoxiang; Fu, Bo; Wang, Fang; Zhu, Xinbao (November 2020). "Synthesis and curing properties of castor oil‐based triglycidyl ether epoxy resin". Polymers for Advanced Technologies. 31 (11): 2552–2560. doi:10.1002/pat.4982. ISSN   1042-7147. S2CID   225739893.
  5. ↑ Jagtap, Ameya Rajendra; More, Aarti (2022-08-01). "Developments in reactive diluents: a review". Polymer Bulletin. 79 (8): 5667–5708. doi:10.1007/s00289-021-03808-5. ISSN   1436-2449. S2CID   235678040.
  6. ↑ US 3351574,Hicks, Darrel D.&Belanger, William J.,"Castor oil polyglycidyl ether",published 1967-11-07, assigned to Celanese Coatings Co.
  7. ↑ Ramon, Eric; Sguazzo, Carmen; Moreira, Pedro M. G. P. (October 2018). "A Review of Recent Research on Bio-Based Epoxy Systems for Engineering Applications and Potentialities in the Aviation Sector". Aerospace. 5 (4): 110. Bibcode:2018Aeros...5..110R. doi: 10.3390/aerospace5040110 . ISSN   2226-4310.
  8. ↑ WOapplication 2019238867,Bevinakatti, Hanamanthsa&Islam, Mojahedul,"Herbicidal formulations comprising glyphosate and cote-based adjuvants",published 2019-12-19, assigned to Nouryon Chemicals International BV
  9. ↑ Zarnitz, Charles. "Flexibilizing modifiers" (PDF). CVC Thermosets.
  10. ↑ Monte, Salvatore J. (1998), Pritchard, Geoffrey (ed.), "Diluents and viscosity modifiers for epoxy resins", Plastics Additives: An A-Z reference, Polymer Science and Technology Series, vol. 1, Dordrecht: Springer Netherlands, pp. 211–216, doi:10.1007/978-94-011-5862-6_24, ISBN   978-94-011-5862-6, archived from the original on 2022-04-11, retrieved 2022-03-29
  11. ↑ WOapplication 2015095994,Shen, Yue; Zhan, Fu& Wu, Yanet al.,"Epoxy resin composition",published 2015-07-02, assigned to Dow Global Technologies LLC
  12. ↑ Hao, Xiu; Fan, Dong-Bin (2018-12-17). "Preparation and characterization of epoxy-crosslinked soy protein adhesive". Journal of Adhesion Science and Technology. 32 (24): 2682–2692. doi:10.1080/01694243.2018.1517488. ISSN   0169-4243. S2CID   105550538.
  13. ↑ "14228-73-0 | CAS DataBase". www.chemicalbook.com. Archived from the original on 2022-04-11. Retrieved 2022-04-11.
  14. ↑ Sathyaraj, S.; Sekar, K. (2021). "Recent Advances in Bio-Based Sustainable Aliphatic and Aromatic Epoxy Resins for Composite Applications". Key Engineering Materials. 882: 121–131. doi:10.4028/www.scientific.net/KEM.882.121. ISSN   1662-9795. S2CID   233301700.
  15. ↑ US 8062468,Finter, Jürgen; Kramer, Andreas& Schulenburg, Jan Olafet al.,"Low-temperature impact resistant thermosetting epoxide resin compositions with solid epoxide resins",published 2011-11-22, assigned to Sika Technology AG
  16. ↑ Santiago, David; Guzmán, Dailyn; Ferrando, Francesc; Serra, Àngels; De la Flor, Silvia (March 2020). "Bio-Based Epoxy Shape-Memory Thermosets from Triglycidyl Phloroglucinol". Polymers. 12 (3): 542. doi: 10.3390/polym12030542 . ISSN   2073-4360. PMC   7182903 . PMID   32131508.
  17. ↑ Pastarnokienė, Liepa; Jonikaitė-Švėgždienė, Jūratė; Lapinskaitė, Neringa; Kulbokaitė, Rūta; Bočkuvienė, Alma; Kochanė, Tatjana; Makuška, Ričardas (2023-07-01). "The effect of reactive diluents on curing of epoxy resins and properties of the cured epoxy coatings". Journal of Coatings Technology and Research. 20 (4): 1207–1221. doi:10.1007/s11998-022-00737-4. ISSN   1935-3804. S2CID   256749849.
  18. ↑ Khalina, Morteza; Beheshty, Mohammad Hosain; Salimi, Ali (2019-08-01). "The effect of reactive diluent on mechanical properties and microstructure of epoxy resins". Polymer Bulletin. 76 (8): 3905–3927. doi:10.1007/s00289-018-2577-6. ISSN   1436-2449. S2CID   105389177.
  19. ↑ Mashouf Roudsari, Ghodsieh; Mohanty, Amar K.; Misra, Manjusri (2017-11-06). "Green Approaches To Engineer Tough Biobased Epoxies: A Review". ACS Sustainable Chemistry & Engineering. 5 (11): 9528–9541. doi: 10.1021/acssuschemeng.7b01422 . ISSN   2168-0485.
  20. ↑ Ma, Yufeng; Wang, Rui; Li, Qiaoguang; Li, Mei; Liu, Chengguo; Jia, Puyou (2021-03-24). "Castor oil as a platform for preparing bio-based chemicals and polymer materials". Green Materials. 10 (3): 99–109. doi:10.1680/jgrma.20.00085. ISSN   2049-1220. S2CID   233687152.
  21. ↑ USapplication 2010326660,Ballard, David Antony&Burn, Andrew,"Use of direct epoxy emulsions for wellbore stabilization",published 2010-12-30, assigned to M-I LLC, since abandoned.

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