Editing Pentaerythritol

{{Chembox
| Verifiedfields = changed
| Watchedfields  = changed
| verifiedrevid  = 444044240
| ImageFile      = Pentaerythritol.svg
| ImageSize      = 
| ImageFile1     = Pentaerythritol-3D-balls.png
| PIN            = 2,2-Bis(hydroxymethyl)propane-1,3-diol<ref name=iupac2013>{{cite book |title=Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book) |publisher=[[Royal Society of Chemistry|The Royal Society of Chemistry]] |date=2014 |location=Cambridge |page=691 |doi=10.1039/9781849733069-FP001 |isbn=978-0-85404-182-4}}</ref>
| OtherNames     = 2,2-Bis(hydroxymethyl)-1,3-propanediol<br />Pentaerythritol<ref name=iupac2013 /><br />Hercules P 6<br />Monopentaerythritol<br />Tetramethylolmethane<br />THME<br />PETP<br />Pentaerythrite<br />Pentek<br />Hercules Aqualon improved technical PE-200
| Section1       = {{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 115-77-5
| PubChem = 8285
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = SU420W1S6N
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 7984
| EC_number = 204-104-9
| RTECS = RZ2490000
| ChEMBL = 3186112
| ChEBI = 134760
| DrugBank = DB13526
| KEGG = D08331
| SMILES = OCC(CO)(CO)CO
| InChI = 1/C5H12O4/c6-1-5(2-7,3-8)4-9/h6-9H,1-4H2
| InChIKey = WXZMFSXDPGVJKK-UHFFFAOYAH
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C5H12O4/c6-1-5(2-7,3-8)4-9/h6-9H,1-4H2
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = WXZMFSXDPGVJKK-UHFFFAOYSA-N
  }}
| Section2       = {{Chembox Properties
| Formula = C<sub>5</sub>H<sub>12</sub>O<sub>4</sub>
| MolarMass = 136.15 g/mol
| Appearance = white solid
| Density = 1.396 g/cm<sup>3</sup>
| MeltingPtC = 260.5
| BoilingPtC = 276
| BoilingPt_notes = at 30 mmHg
| Solubility = {{unbulleted list|
38.46 g/L (0°C) |
47.62 g/L (10°C) |
52.60 g/L (15°C) |
56.60 g/L (20°C) |
74.07 g/L (30°C) |
115.0 g/L (40°C) |
180.3 g/L (60°C) |
285.7 g/L (80°C) |
500.0 g/L (100°C)<ref>{{cite book |last1=Yalkowsky |first1=Samuel H. |title=Handbook of aqueous solubility data |date=2010 |publisher=CRC Press |location=Boca Raton, FL |isbn=9781439802465 |page=185 |edition=Second}}</ref> 
}}
| SolubleOther = 
{{unbulleted list|
[[TBuOH]], 15g/L (60°C)<ref>{{cite journal |last1=Yadav |first1=Manish G. |last2=Vadgama |first2=Rajeshkumar N. |last3=Kavadia |first3=Monali R. |last4=Odaneth |first4=Annamma Anil |last5=Lali |first5=Arvind M. |title=Production of Pentaerythritol Monoricinoleate (PEMR) by immobilized Candida antarctica lipase B |journal=Biotechnology Reports |date=September 2019 |volume=23 |pages=e00353 |doi=10.1016/j.btre.2019.e00353|pmid=31304100 |pmc=6599945 }}</ref> |
[[DMSO]], 20g/L (25°C)
}}

Slightly soluble in:[[methanol]], [[ethanol]], [[glycerol]], [[ethylene glycol]], [[formamide]];

insoluble in: [[acetone]], [[toluene]], [[heptane]], [[diethyl ether]], [[dichloromethane]]
| VaporPressure = 0.00000008 mmHg (20°C)<ref name=PGCH/>
  }}
| Section3       = {{Chembox Hazards
| MainHazards = 
| FlashPtC = 200.1
| AutoignitionPtC = 
| IDLH = N.D.<ref name=PGCH>{{PGCH|0485}}</ref>
| REL = TWA 10 mg/m<sup>3</sup> (total) TWA 5 mg/m<sup>3</sup> (resp)<ref name=PGCH/>
| PEL = TWA 15 mg/m<sup>3</sup> (total) TWA 5 mg/m<sup>3</sup> (resp)<ref name=PGCH/>
 }}
| Section9       = {{Chembox Related
| OtherCompounds = [[Neopentane]], [[Neopentyl alcohol]], [[Neopentyl glycol]], [[Trimethylolethane]], [[Orthocarbonic acid]]
  }}
}}
'''Pentaerythritol''' is an [[organic compound]] with the [[chemical formula|formula]] C(CH<sub>2</sub>OH)<sub>4</sub>. The molecular structure can be described as a [[neopentane]] with one [[hydrogen]] atom in each [[methyl]] group replaced by a [[hydroxyl]] (–OH) group.  It is therefore a [[polyol]], specifically a [[tetrol]]. 

Pentaerythritol is a white solid. It is a building block for the synthesis and production of [[explosive]]s, [[plastic]]s, [[paint]]s, [[home appliance|appliance]]s, [[cosmetics]], and many other commercial products.

The word pentaerythritol is a blend of ''penta-'' in reference to its five [[carbon]] atoms and ''[[erythritol]]'', which also possesses 4 alcohol groups.

==Synthesis==
Pentaerythritol was first reported in 1891 by German chemist [[Bernhard Tollens]] and his student P. Wigand.<ref>{{cite journal |last1=Tollens |first1=B. |last2=Wigand |first2=P. |title=Ueber den Penta-Erythrit, einen aus Formaldehyd und Acetaldehyd synthetisch hergestellten vierwerthigen Alkohol (On pentaerythritol, a quaternary alcohol synthetically produced from formaldehyde and acetaldehyde) |journal=Justus Liebig's Annalen der Chemie |date=1891 |volume=265 |issue=3 |pages=316–340 |url=https://zenodo.org/record/1427437/files/article.pdf |language=de |doi=10.1002/jlac.18912650303}}</ref> It may be prepared via a base-catalyzed multiple-[[addition reaction]] between [[acetaldehyde]] and 3 equivalents of [[formaldehyde]] to give [[pentaerythrose]] (CAS: 3818-32-4), followed by a [[Cannizzaro reaction]] with a fourth equivalent of [[formaldehyde]] to give the final product plus [[formate]] ion.<ref name="Schurink1941">{{OrgSynth |author=Schurink, H. B. J. |title=Pentaerythritol |collvol=1 |collvolpages=425 |year=1925 |prep=CV1P0425 |volume=4 |pages=53 |doi=10.15227/orgsyn.004.0053}}</ref>

:[[File:Pentaerythritol Synthesis.svg|575px]]

==Uses==
Pentaerythritol is a versatile building block for the preparation of many compounds,<ref>{{cite journal |last1=Marrian |first1=S. F. |title=The Chemical Reactions of Pentaerythritol and its Derivatives. |journal=Chemical Reviews |date=1 August 1948 |volume=43 |issue=1 |pages=149–202 |doi=10.1021/cr60134a004|pmid=18876970 }}</ref> particularly polyfunctionalized derivatives. applications include [[alkyd]] [[resin]]s, [[varnish]]es, [[polyvinyl chloride]] stabilizers, [[tall oil]] [[ester]]s, [[antioxidant]]s (e.g. [[Pentaerythritol tetrakis(3,5-di-tert-butyl-4-hydroxyhydrocinnamate)|Anox 20]]). Such derivatives are found in [[plastic]]s, [[paint]]s, [[cosmetics]], and many other products. Relevant to resins, pentaerythritol is a precursor to other [[polyol]], such as [[dipentaerythritol]]:<ref>{{Ullmann |doi=10.1002/14356007.a01_305.pub2|title=Alcohols, Polyhydric |year=2008 |last1=Werle |first1=Peter |last2=Morawietz |first2=Marcus |last3=Lundmark |first3=Stefan |last4=Sörensen |first4=Kent |last5=Karvinen |first5=Esko |last6=Lehtonen |first6=Juha |isbn=978-3527306732 }}</ref>
:{{chem2|2 C(CH2OH)4  -> O[CH2C(CH2OH)3]2 +  H2O}}

[[Ester]]s of pentaerythitol are [[biodegradable]],<ref>{{cite book |title=The Complete Book on Adhesives, Glues & Resins Technology (with Process & Formulations) 2nd Revised Edition|author1=NPCS Board of Consultants & Engineers|year=2016}}</ref><ref>{{cite book|title=Synthetic Resins Technology Handbook|author1=NIIR Board of Engineers & Consultants|year=2005}}</ref> and they are used as [[transformer oil]]s.<ref>{{cite book | url=https://books.google.com/books?id=2kjMBQAAQBAJ&pg=PA71 | title=Synthetics, Mineral Oils, and Bio-Based Lubricants: Chemistry and Technology | isbn=9781420027181 | last1=Rudnick | first1=Leslie R. | date=22 December 2005 }}</ref> Due to a very high [[flash point]] they also find some use in lubricating [[gas turbine]]s.<ref>{{cite book | url=https://books.google.com/books?id=h6X0NM7ME8IC&pg=PA375 | title=Modern Tribology Handbook, Two Volume Set | isbn=9780849377877 | last1=Bhushan | first1=Bharat | date=28 December 2000 }}</ref>

===Ester derivatives===
Pentaerythritol is a precursor to esters of the type C(CH<sub>2</sub>OX)<sub>4</sub>. Such derivatives are [[pentaerythritol tetranitrate]] (PETN),  a [[vasodilator]] and [[explosive]], the trinitrate [[derivative (chemistry)|derivative]] [[pentrinitrol]] (Petrin), the tetraacetate [[normosterol]] (PAG), and the [[Cross-link|polymer cross-linking agent]]s [[pentaerythritol tetraacrylate]] and [[pentaerythritol tetrakis(3-mercaptopropionate)]].<ref>{{cite journal|title=The Chemical Reactions of Pentaerythritol and its Derivatives|author=S. F. Marrian |journal=[[Chemical Reviews]]|year=1948|volume=43 |issue=1|pages=149–202|doi=10.1021/cr60134a004 |pmid=18876970}}</ref><ref>{{cite journal |last1=Hoyle |first1=Charles E. |last2=Bowman |first2=Christopher N. |title=Thiol–Ene Click Chemistry |journal=[[Angewandte Chemie International Edition]] |year=2010 |volume=49 |issue=9 |doi=10.1002/anie.200903924 |pages=1542–1543}}</ref>

A linear polymer which can be described as a ([[spiro compound|spiro]]) [[orthocarbonate]] ester of pentaerythritol, whose formula could be written as {{chem2|[(\sCH2)2C(CH2\s)2 (\sO)2C(O\s)2]_{''n''}|}}, was synthesized in 2002.<ref name=voda2002>David T. Vodak, Matthew Braun, Lykourgos Iordanidis, Jacques Plévert, Michael Stevens, Larry Beck, John C. H. Spence, Michael O'Keeffe, Omar M. Yaghi (2002): "One-Step Synthesis and Structure of an Oligo(spiro-orthocarbonate)". ''Journal of the American Chemical Society'', volume 124, issue 18, pages 4942–4943. {{doi|10.1021/ja017683i}}</ref>

===Fire retardants===
Pentaerythritol is used as a fire retardant, such as in plastics and [[intumescent]] paints and coatings. It releases water upon heating and leaves a deposit of thermally insulating char.<ref>{{Ullmann |doi=10.1002/14356007.a18_359.pub2 |title=Paints and Coatings |year=2006 |last1=Stoye |first1=Dieter |isbn=3527306730 |display-authors=etal }}</ref>

==See also==
* [[1,6-Hexanediol]]
* [[Neopentyl glycol]]
* [[Trimethylolethane]]
* [[Trimethylolpropane]]

==References==
{{Reflist}}

[[Category:Tetrols]]
[[Category:Alkanols]]
[[Category:Substances discovered in the 19th century]]