Neopentyl glycol diglycidyl ether

Names
IUPAC name

2-[[2,2-dimethyl-3-(oxiran-2-ylmethoxy)propoxy]methyl]oxirane

Other names

Neopentyl glycol diglycidyl ether; 1,3-Bis(2,3-epoxypropoxy)-2,2-dimethylpropane; 2,2'-((2,2-Dimethyl-1,3-propanediyl)bis(oxymethylene))bis(oxirane); CCRIS 2640; Diglycidyl ether of neopentyl gylcol; EINECS 241-536-7; Heloxy WC68; UNII-9288EM7AOW; Oxirane, 2,2'-((2,2-dimethyl-1,3-propanediyl)bis(oxymethylene))bis-; Propane, 1,3-bis(2,3-epoxypropoxy)-2,2-dimethyl-

Identifiers

CAS Number

* 17557-23-2

3D model (JSmol)

* Interactive image

ChEMBL |

* ChEMBL1587512

ChemSpider |

* 26599

EC Number |

* 241-536-7

PubChem CID

* 28594

InChI

* InChI=1S/C11H20O4/c1-11(2,7-12-3-9-5-14-9)8-13-4-10-6-15-10/h9-10H,3-8H2,1-2H3

Key: KUAUJXBLDYVELT-UHFFFAOYSA-N

SMILES

* CC(C)(COCC1CO1)COCC2CO2

Properties

Chemical formula

| C11H20O4
Molar mass | 216.275 g/mol
Hazards
GHS pictograms |
GHS Signal word | Warning

GHS hazard statements

| H315, H317

GHS precautionary statements

| P261, P264, P272, P280, P302+352, P321, P332+313, P333+313, P362, P363, P501

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Infobox references

Tracking categories (test):

* SizeSet

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.[2] It has two oxirane groups per molecule.[3] Its principle use is in modifying epoxy resins.

It is REACH registered.[4] The IUPAC name is 2-[[2,2-dimethyl-3-(oxiran-2-ylmethoxy)propoxy]methyl]oxirane.[5]

## Contents

* 1 Synthesis
* 2 Uses
* 3 Toxicity
* 4 See also
* 5 References
* 6 Further reading
* 7 External websites

## Synthesis

Neopentyl glycol and epichlorohydrin are reacted in the presence of a Lewis acid catalyst to form a halohydrin. This is followed by washing with sodium hydroxide in dehydrochlorination step. This forms Neopentyl glycol diglycidyl ether.[6] The waste products are water and sodium chloride and excess caustic soda. One of the quality control tests would involve measuring the Epoxy value by determination of the epoxy equivalent weight.

## Uses

A key use is modifying the viscosity and properties of epoxy resins[7] which may then be formulated into CASE applications: Coatings,[8] Adhesives,[9] Sealants and Elastomers. These uses include cationic polymerization reactions.[10][11] It is also used to synthesize other molecules.[12][13][14]

## Toxicity

NPGDGE toxicity is fairly well understood. It is classed as a skin irritant and skin sensitizer.[15][16]

## See also

* o-Cresyl glycidyl ether
* Allyl glycidyl ether
* 2-Ethylhexyl glycidyl ether
* n-Butyl glycidyl ether
* Epoxide
* Glycidol

## References

1. ↑ "Neopentyl glycol diglycidyl ether" (in en). https://pubchem.ncbi.nlm.nih.gov/compound/Neopentyl-glycol-diglycidyl-ether#section=Safety-and-Hazards.
2. ↑ "System of Registries | US EPA" (in en). https://sor.epa.gov/sor_internet/registry/substreg/searchandretrieve/advancedsearch/externalSearch.do?p_type=CASNO&p_value=17557-23-2.
3. ↑ PubChem. "Neopentyl glycol diglycidyl ether" (in en). https://pubchem.ncbi.nlm.nih.gov/compound/28594.
4. ↑ "Substance Information - ECHA" (in en-GB). https://echa.europa.eu/substance-information/-/substanceinfo/100.037.745.
5. ↑ PubChem. "Neopentyl glycol diglycidyl ether" (in en). https://pubchem.ncbi.nlm.nih.gov/compound/28594.
6. ↑ Crivello, James V. (2006). "Design and synthesis of multifunctional glycidyl ethers that undergo frontal polymerization". Journal of Polymer Science Part A: Polymer Chemistry 44 (21): 6435–6448. doi:10.1002/pola.21761. ISSN 0887-624X. Bibcode: 2006JPoSA..44.6435C. https://doi.org/10.1002/pola.21761.
7. ↑ Monte, Salvatore J. (1998), Pritchard, Geoffrey, ed., "Diluents and viscosity modifiers for epoxy resins" (in en), Plastics Additives: An A-Z reference, Polymer Science and Technology Series (Dordrecht: Springer Netherlands) 1: pp. 211–216, doi:10.1007/978-94-011-5862-6_24, ISBN 978-94-011-5862-6, https://doi.org/10.1007/978-94-011-5862-6_24, retrieved 2022-03-29
8. ↑ Howarth G.A "Synthesis of a legislation compliant corrosion protection coating system based on urethane, oxazolidine and waterborne epoxy technology" page 23 Master of Science Thesis April 1997 Imperial College London
9. ↑ Luo, Jing; Luo, Jianlin; Zhang, Jizhi; Bai, Yuanyuan; Gao, Qiang; Li, Jianzhang; Li, Li (September 2016). "A New Flexible Soy-Based Adhesive Enhanced with Neopentyl Glycol Diglycidyl Ether: Properties and Application" (in en). Polymers 8 (9): 346. doi:10.3390/polym8090346. ISSN 2073-4360. PMID 30974622.
10. ↑ Crivello, James V (March 2006). "Cationic photopolymerization of alkyl glycidyl ethers". Journal of Polymer Science Part A: Polymer Chemistry 44 (9): 3036–3052. doi:10.1002/pola.21419. Bibcode: 2006JPoSA..44.3036C. https://onlinelibrary.wiley.com/doi/full/10.1002/pola.21419.
11. ↑ Bulut, Umut; Crivello, James V. (2005-04-02). "Investigation of the Reactivity of Epoxide Monomers in Photoinitiated Cationic Polymerization". Macromolecules 38 (9): 3584–3595. doi:10.1021/ma050106k. ISSN 0024-9297. Bibcode: 2005MaMol..38.3584B. https://pubs.acs.org/doi/full/10.1021/ma050106k.
12. ↑ Simokaitiene, Jurate; Lazauskaite, Ruta; Grazulevicius, Juozas V (2002-02-28). "Photopolymerization of neopentyl glycol diglycidylether and its compositions with 9-(2-oxiranylmethyl) carbazole" (in en). Journal of Photochemistry and Photobiology A: Chemistry 147 (1): 55–61. doi:10.1016/S1010-6030(01)00622-0. ISSN 1010-6030. https://www.sciencedirect.com/science/article/pii/S1010603001006220.
13. ↑ Polyepoxy Compound Fixation / Yasuharu Noishiki, Teruo Miyata (2 ed.), CRC Press, 2008, pp. 2263–2272, doi:10.1201/9780429154065-213, ISBN 978-0-429-15406-5, https://www.taylorfrancis.com/chapters/edit/10.1201/9780429154065-213/polyepoxy-compound-fixation-yasuharu-noishiki-teruo-miyata, retrieved 2022-03-29
14. ↑ Huang, Bi-wu; Huang, Bo-fen; Chen, Wei-qing; Ouyang, Zhi-qiang (2009-10-11). "Synthesis of a novel UV-curable prepolymer neopentyl glycol diglycidyl ether diacrylate and its cured film tensile property" (in en). Journal of Shanghai University (English Edition) 13 (5): 396. doi:10.1007/s11741-009-0511-3. ISSN 1863-236X. https://doi.org/10.1007/s11741-009-0511-3.
15. ↑ US EPA, OCSPP (2013-03-01). "Chemical Data Reporting under the Toxic Substances Control Act" (in en). https://www.epa.gov/chemical-data-reporting.
16. ↑ Jolanki, R.; Sysilampi, M.-L.; Kanerva, L.; Estlander, T. (1989). Frosch, Peter; Dooms-Goossens, A.; Lachapelle, J.-M. et al.. eds. "Contact Allergy to Cycloaliphatic Epoxy Resins" (in en). Current Topics in Contact Dermatitis (Berlin, Heidelberg: Springer): 360–367. doi:10.1007/978-3-642-74299-6_75. ISBN 978-3-642-74299-6. https://link.springer.com/chapter/10.1007/978-3-642-74299-6_75.

## Further reading

* Epoxy resin technology.. Paul F. Bruins, Polytechnic Institute of Brooklyn. New York: Interscience Publishers. 1968. ISBN 0-470-11390-1. OCLC 182890. https://www.worldcat.org/oclc/182890.
* Flick, Ernest W. (1993). Epoxy resins, curing agents, compounds, and modifiers : an industrial guide. Park Ridge, NJ. ISBN 978-0-8155-1708-5. OCLC 915134542. https://www.worldcat.org/oclc/915134542.
* Lee, Henry (1967). Handbook of epoxy resins. Kris Neville ([2nd, expanded work] ed.). New York: McGraw-Hill. ISBN 0-07-036997-6. OCLC 311631322. https://www.worldcat.org/oclc/311631322.
* "Dow Epoxy Resins". http://nmt.edu/academics/mtls/faculty/mccoy/docs2/chemistry/DowEpoxyResins.pdf.

## External websites

* Hexion difunctional epoxy diluents
* Denacol epoxy diluent range
* Aalchem NPGDGE
* Cargill Reactive diluents

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*[CID]: Compound ID
*[H315]: Causes skin irritation
*[H317]: May cause an allergic skin reaction
*[P261]: Avoid breathing dust/fume/gas/mist/vapours/spray
*[P264]: Wash … thoroughly after handling
*[P272]: Contaminated work clothing should not be allowed out of the workplace
*[P280]: Wear protective gloves/protective clothing/eye protection/face protection
*[P302+352]: IF ON SKIN: Wash with soap and water
*[P321]: Specific treatment (see … on this label)
*[P332+313]: If skin irritation occurs: Get medical advice/attention
*[P333+313]: If skin irritation or a rash occurs: Get medical advice/attention
*[P362]: Take off contaminated clothing and wash before reuse
*[P363]: Wash contaminated clothing before reuse
*[P501]: Dispose of contents/container to …