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{{chembox {{chembox
| Verifiedfields = changed
| verifiedrevid = 303034209
| Watchedfields = changed
| verifiedrevid = 376962659
| Name = Neopentyl glycol | Name = Neopentyl glycol
| ImageFile = 2,2-dimethylpropane-1,3-diol 200.svg
| ImageFileL1 = Neopentyl glycol.png
| ImageSizeL1 = 120px | ImageSize = 150px
| ImageNameL1 = Neopentyl glycol | ImageName = Neopentyl glycol
| ImageFile1 = Neopentyl-glycol-3D-balls.png
| ImageFileR1 = Neopentylglycol.png
| ImageSizeR1 = 120px | ImageSize1 = 160px
| ImageNameR1 = Neopentyl glycol | ImageAlt1 = Neopentyl glycol molecule
| IUPACName = 2,2-Dimethyl-1,3-propanediol | PIN = 2,2-Dimethylpropane-1,3-diol
| OtherNames = | OtherNames = 2,2-Dimethyl-1,3-propanediol
| Reference = <ref name="hand"> | Reference = <ref name="hand">
{{Citation {{Citation
| last = Lide | last = Lide
| first = David R. | first = David R.
| author-link = | author-link =
| publication-date =
| last2 =
| first2 = | year = 1998
| title = Handbook of Chemistry and Physics
| author2-link =
| edition = 87
| publication-date =
| date = | volume =
| year = 1998 | series =
| publication-place = Boca Raton, Florida
| title = Handbook of Chemistry and Physics
| edition = 87 | place =
| volume = | publisher = CRC Press
| series = | id =
| isbn = 0-8493-0594-2
| publication-place = Boca Raton, FL
| place = | doi =
| oclc =
| publisher = CRC Press
| pages = 3‑228, 5‑42, 16‑22
| id =
| url =
| isbn = 0849305942
| doi = | accessdate =
| oclc =
| pages = 3‑228, 5‑42, 16‑22
| url =
| accessdate =
}}</ref> }}</ref>
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| CASNo = 126-30-7 | CASNo = 126-30-7
| CASNo_Ref = | CASNo_Ref = {{cascite|correct|CAS}}
| CASOther = | CASNoOther =
| UNII_Ref = {{fdacite|correct|FDA}}
| RTECS =
| EINECS = | UNII = QI80HXD6S5
| PubChem = 31344
| RTECS =
| EINECS =
| ChEBI = 143768
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 13835293
| SMILES = CC(C)(CO)CO
| InChI = 1/C5H12O2/c1-5(2,3-6)4-7/h6-7H,3-4H2,1-2H3
| InChIKey = SLCVBVWXLSEKPL-UHFFFAOYAD
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C5H12O2/c1-5(2,3-6)4-7/h6-7H,3-4H2,1-2H3
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = SLCVBVWXLSEKPL-UHFFFAOYSA-N
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| Formula = C<sub>5</sub>H<sub>12</sub>O<sub>2</sub> | Formula = C<sub>5</sub>H<sub>12</sub>O<sub>2</sub>
| MolarMass = 104.148 g/mol | MolarMass = 104.148 g/mol
| Appearance = | Appearance =
| Density = | Density =
| MeltingPt = 129.13°C | MeltingPtC = 129.13
| BoilingPt = 208°C | BoilingPtC = 208
| Solubility = soluble in water | Solubility = good
| SolubleOther = soluble in ], ], very soluble in ], ] | SolubleOther = soluble in ], ], very soluble in ], ]
}} }}
| Section3 = {{Chembox Structure |Section3={{Chembox Structure
| Coordination = | Coordination =
| CrystalStruct = | CrystalStruct =
}} }}
| Section4 = {{Chembox Thermochemistry |Section4={{Chembox Thermochemistry
| DeltaHf = -551.2 ] | DeltaHf = -551.2 ]
| DeltaHc = | DeltaHc =
| Entropy = | Entropy =
| HeatCapacity = | HeatCapacity =
}} }}
| Section7 = {{Chembox Hazards |Section7={{Chembox Hazards
| ExternalMSDS = | ExternalSDS =
| EUIndex = | NFPA-H =
| NFPA-H =
| NFPA-F = | NFPA-F =
| NFPA-R = | NFPA-R =
| RPhrases = | FlashPtC = 129
| SPhrases =
| FlashPt = 129°C
}} }}
| Section8 = {{Chembox Related |Section8={{Chembox Related
| OtherAnions = | OtherAnions =
| OtherCations = | OtherCations =
}} }}
}} }}


'''Neopentyl glycol''' (] name 2,2-dimethyl-1,3-propanediol) is an ] ]. It is used in the sythesis of ]s, ]s, ]s, and ]s. When used in the manufacture of polyesters, it enhances the product's stability toward heat, light, and water. '''Neopentyl glycol''' (] name: 2,2-dimethylpropane-1,3-diol) is an ] ]. It is used in the synthesis of ]s, ]s, ]s, and ]s. When used in the manufacture of polyesters, it enhances the stability of the product towards heat, light, and water. By ] reaction with ] or ] acids, synthetic lubricating esters with reduced potential for ] or ], compared to natural esters, can be produced.


== Reactions == == Reactions ==
Neopentyl glycol is synthesized industrially by the ] of ] and ]. This creates the intermediate hydroxypivaldehyde, which can be converted to neopentyl glycol with either excess formaldehyde or catalytic hydrogenation of the ] group to an ] group.<ref name="ioc"> Neopentyl glycol is synthesized industrially by the ] of ] and ]. This creates the intermediate ], which can be converted to neopentyl glycol by either a ] with excess formaldehyde, or by hydrogenation using palladium on carbon.<ref name="ioc">
{{Citation {{Citation
| last = Weissermel | last1 = Weissermel
| first = Klaus | first1 = Klaus
| author-link = | author-link =
| last2 = Arpe | last2 = Arpe
| first2 = Hans-Jürgen | first2 = Hans-Jürgen
| author2-link = | author2-link =
| last3 = Lindley | last3 = Lindley
| first3 =Charlet R. | first3 =Charlet R.
| author3-link = | author3-link =
| publication-date = | publication-date =
| date = | year = 2003
| title = Industrial Organic Chemistry
| year = 2003
| edition = 4
| title = Industrial Organic Chemistry
| edition = 4 | volume =
| volume = | series =
| publication-place =
| series =
| publication-place = | place =
| place = | publisher = Wiley-VCH
| id =
| publisher = Wiley-VCH
| isbn = 978-3-527-30578-0
| id = | doi =
| isbn = 9783527305780
| doi = | oclc =
| pages = 214–215
| oclc =
| url = https://books.google.com/books?id=OUGVPYqtnNgC&q=%22Neopentyl+glycol%22&pg=PA215
| pages = 214–215
| accessdate = 2009-07-20
| url = http://books.google.com/?id=OUGVPYqtnNgC&pg=PA215&dq=%22Neopentyl+glycol%22
| accessdate = 2009-07-20
}}</ref> }}</ref>


Owing to its tendency to form cyclic derivatives (see ]), it is used as a ] for ketones, for example in ] synthesis. Similarly it gives
== References ==
], which can be useful in the ]s.<ref>{{cite journal|doi=10.15227/orgsyn.097.0245 |title=Anhydrous, Homogeneous, Suzuki-Miyaura Cross-Coupling of Boronic Esters using Potassium Trimethylsilanolate |year=2020 |last1=p. Delaney |first1=Connor |last2=Heyboer |first2=E. M. |last3=Denmark |first3=S. E. |journal=Organic Syntheses |volume=97 |pages=245–261 |pmid=33456091 |pmc=7808858 }}</ref><ref name="BlairZhong2016">{{cite journal|last1=Blair|first1=D. J.|last2=Zhong|first2=S.|last3=Hesse|first3=M. J.|last4=Zabaleta|first4=N.|last5=Myers|first5=E. L.|last6=Aggarwal|first6=V. K.|title=Full chirality transfer in the synthesis of hindered tertiary boronic esters under in situ lithiation–borylation conditions|journal=Chemical Communications|volume=52|issue=30|year=2016|pages=5289–5292|issn=1359-7345|doi=10.1039/C6CC00536E|pmid=27002235|doi-access=free|hdl=1983/879ca6cc-b403-48ea-8a81-3ff6988db405|hdl-access=free}}</ref>
{{Reflist}}


A ] of neopentyl glycol with ] gives ].
]
]
]


Neopentyl glycol is a precursor to ]. The sequence begins with alkylation with ] using a ] ]. ] of the resulting ] with ] affords the desired ether.<ref>{{Cite journal |last=Crivello |first=James V. |date=2006 |title=Design and synthesis of multifunctional glycidyl ethers that undergo frontal polymerization |url=https://doi.org/10.1002/pola.21761 |journal=Journal of Polymer Science Part A: Polymer Chemistry |volume=44 |issue=21 |pages=6435–6448 |doi=10.1002/pola.21761 |bibcode=2006JPoSA..44.6435C |issn=0887-624X}}</ref>


==Research==
It has been reported that ]s of neopentyl glycol exhibit a colossal barocaloric effect (CBCEs), which is a cooling effect caused by pressure-induced phase transitions. The obtained entropy changes are about 389 joules per kilogram per kelvin near room temperature. This CBCE phenomenon is likely to be very useful in future solid-state ] technologies.<ref name="nature">
{{Citation
| last = Li
| first = Bing |display-authors=et al
| date = 27 March 2019
| title = Nature
| pages = 506–510
}}</ref>


==See also==
* ]
* ]
* ]


== References ==
]
{{Reflist}}
]

]
]
]
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