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{{chembox |
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| verifiedrevid = 303034209 |
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| Watchedfields = changed |
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| verifiedrevid = 376962659 |
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| Name = Neopentyl glycol |
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| Name = Neopentyl glycol |
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| ImageFile = 2,2-dimethylpropane-1,3-diol 200.svg |
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| ImageFileL1 = Neopentyl glycol.png |
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| ImageSizeL1 = 120px |
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| ImageSize = 150px |
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| ImageNameL1 = Neopentyl glycol |
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| ImageName = Neopentyl glycol |
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| ImageFile1 = Neopentyl-glycol-3D-balls.png |
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| ImageFileR1 = Neopentylglycol.png |
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| ImageSizeR1 = 120px |
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| ImageSize1 = 160px |
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| ImageNameR1 = Neopentyl glycol |
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| ImageAlt1 = Neopentyl glycol molecule |
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| IUPACName = 2,2-Dimethyl-1,3-propanediol |
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| PIN = 2,2-Dimethylpropane-1,3-diol |
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| OtherNames = |
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| OtherNames = 2,2-Dimethyl-1,3-propanediol |
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| Reference = <ref name="hand"> |
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| Reference = <ref name="hand"> |
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{{Citation |
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{{Citation |
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| last = Lide |
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| last = Lide |
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| first = David R. |
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| first = David R. |
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| author-link = |
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| author-link = |
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| publication-date = |
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| last2 = |
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| first2 = |
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| year = 1998 |
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| title = Handbook of Chemistry and Physics |
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| author2-link = |
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| edition = 87 |
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| publication-date = |
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| date = |
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| volume = |
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| year = 1998 |
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| series = |
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| publication-place = Boca Raton, Florida |
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| title = Handbook of Chemistry and Physics |
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| edition = 87 |
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| place = |
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| volume = |
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| publisher = CRC Press |
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| series = |
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| id = |
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| isbn = 0-8493-0594-2 |
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| publication-place = Boca Raton, FL |
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| place = |
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| doi = |
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| oclc = |
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| publisher = CRC Press |
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| pages = 3‑228, 5‑42, 16‑22 |
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| id = |
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| url = |
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| isbn = 0849305942 |
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| doi = |
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| accessdate = |
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| oclc = |
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| pages = 3‑228, 5‑42, 16‑22 |
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| url = |
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| accessdate = |
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}}</ref> |
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}}</ref> |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| CASNo = 126-30-7 |
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| CASNo = 126-30-7 |
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| CASNo_Ref = |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASOther = |
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| CASNoOther = |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| RTECS = |
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| EINECS = |
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| UNII = QI80HXD6S5 |
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| PubChem = 31344 |
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| RTECS = |
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| EINECS = |
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| ChEBI = 143768 |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 13835293 |
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| SMILES = CC(C)(CO)CO |
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| InChI = 1/C5H12O2/c1-5(2,3-6)4-7/h6-7H,3-4H2,1-2H3 |
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| InChIKey = SLCVBVWXLSEKPL-UHFFFAOYAD |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI = 1S/C5H12O2/c1-5(2,3-6)4-7/h6-7H,3-4H2,1-2H3 |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = SLCVBVWXLSEKPL-UHFFFAOYSA-N |
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}} |
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}} |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula = C<sub>5</sub>H<sub>12</sub>O<sub>2</sub> |
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| Formula = C<sub>5</sub>H<sub>12</sub>O<sub>2</sub> |
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| MolarMass = 104.148 g/mol |
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| MolarMass = 104.148 g/mol |
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| Appearance = |
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| Appearance = |
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| Density = |
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| Density = |
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| MeltingPt = 129.13°C |
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| MeltingPtC = 129.13 |
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| BoilingPt = 208°C |
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| BoilingPtC = 208 |
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| Solubility = soluble in water |
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| Solubility = good |
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| SolubleOther = soluble in ], ], very soluble in ], ] |
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| SolubleOther = soluble in ], ], very soluble in ], ] |
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}} |
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| Section3 = {{Chembox Structure |
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|Section3={{Chembox Structure |
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| Coordination = |
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| Coordination = |
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| CrystalStruct = |
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| CrystalStruct = |
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}} |
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| Section4 = {{Chembox Thermochemistry |
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|Section4={{Chembox Thermochemistry |
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| DeltaHf = -551.2 ] |
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| DeltaHf = -551.2 ] |
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| DeltaHc = |
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| DeltaHc = |
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| Entropy = |
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| Entropy = |
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| HeatCapacity = |
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| HeatCapacity = |
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| Section7 = {{Chembox Hazards |
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|Section7={{Chembox Hazards |
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| ExternalMSDS = |
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| ExternalSDS = |
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| EUIndex = |
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| NFPA-H = |
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| NFPA-H = |
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| NFPA-F = |
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| NFPA-F = |
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| NFPA-R = |
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| NFPA-R = |
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| RPhrases = |
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| FlashPtC = 129 |
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| SPhrases = |
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| FlashPt = 129°C |
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}} |
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}} |
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| Section8 = {{Chembox Related |
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|Section8={{Chembox Related |
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| OtherAnions = |
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| OtherAnions = |
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| OtherCations = |
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| OtherCations = |
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'''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. |
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'''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. |
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== Reactions == |
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== Reactions == |
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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"> |
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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"> |
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{{Citation |
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{{Citation |
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| last = Weissermel |
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| last1 = Weissermel |
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| first = Klaus |
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| first1 = Klaus |
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| author-link = |
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| author-link = |
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| last2 = Arpe |
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| last2 = Arpe |
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| first2 = Hans-Jürgen |
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| first2 = Hans-Jürgen |
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| author2-link = |
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| author2-link = |
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| last3 = Lindley |
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| last3 = Lindley |
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| first3 =Charlet R. |
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| first3 =Charlet R. |
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| author3-link = |
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| author3-link = |
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| publication-date = |
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| publication-date = |
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| date = |
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| year = 2003 |
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| title = Industrial Organic Chemistry |
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| year = 2003 |
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| edition = 4 |
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| title = Industrial Organic Chemistry |
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| edition = 4 |
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| volume = |
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| volume = |
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| series = |
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| publication-place = |
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| series = |
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| publication-place = |
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| place = |
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| publisher = Wiley-VCH |
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| id = |
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| publisher = Wiley-VCH |
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| isbn = 978-3-527-30578-0 |
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| id = |
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| doi = |
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| isbn = 9783527305780 |
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| doi = |
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| oclc = |
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| pages = 214–215 |
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| oclc = |
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| url = https://books.google.com/books?id=OUGVPYqtnNgC&q=%22Neopentyl+glycol%22&pg=PA215 |
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| pages = 214–215 |
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| accessdate = 2009-07-20 |
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| url = http://books.google.com/?id=OUGVPYqtnNgC&pg=PA215&dq=%22Neopentyl+glycol%22 |
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| accessdate = 2009-07-20 |
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}}</ref> |
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}}</ref> |
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Owing to its tendency to form cyclic derivatives (see ]), it is used as a ] for ketones, for example in ] synthesis. Similarly it gives |
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== References == |
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], 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> |
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{{Reflist}} |
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A ] of neopentyl glycol with ] gives ]. |
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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> |
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==Research== |
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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"> |
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{{Citation |
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| last = Li |
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| first = Bing |display-authors=et al |
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| date = 27 March 2019 |
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| title = Nature |
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| pages = 506–510 |
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}}</ref> |
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==See also== |
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* ] |
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* ] |
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* ] |
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== References == |
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{{Reflist}} |
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