Difference between revisions of "Pentaerythritol"
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| MeltingPt_ref = | | MeltingPt_ref = | ||
| MeltingPt_notes = | | MeltingPt_notes = | ||
| − | | Odor = | + | | Odor = Odorless |
| pKa = | | pKa = | ||
| pKb = | | pKb = | ||
| Solubility = 5.6 g/100 mL (15 °C) | | Solubility = 5.6 g/100 mL (15 °C) | ||
| − | | SolubleOther = | + | | SolubleOther = Soluble in [[ethanol]], [[ethylene glycol]], [[formamide]], [[glycerol]], [[isopropanol]], [[methanol]]<br>Insoluble in [[acetone]], [[benzene]], [[Carbon tetrachloride|CCl<sub>4</sub>]], [[diethyl ether]], [[mineral oil]], [[toluene]] |
| Solvent = | | Solvent = | ||
| VaporPressure = 0.00000008 mmHg (20°C) | | VaporPressure = 0.00000008 mmHg (20°C) | ||
| Line 88: | Line 88: | ||
}} | }} | ||
| Section6 = {{Chembox Hazards | | Section6 = {{Chembox Hazards | ||
| − | | AutoignitionPt = 490 °C | + | | AutoignitionPt = 490 °C (914 °F; 763 K) |
| ExploLimits = | | ExploLimits = | ||
| − | | ExternalMSDS = [https://www. | + | | ExternalMSDS = [https://www.docdroid.net/xNSWu7m/pentaerythritol-sa.pdf Sigma-Aldrich] |
| − | | FlashPt = 200.1 °C | + | | FlashPt = 200.1 °C (392.18 °F; 473.25 K) |
| LD50 = 10,000 mg/kg (rat, oral) | | LD50 = 10,000 mg/kg (rat, oral) | ||
| LC50 = 50,000 mg/L (freshwater fish, 48 h) | | LC50 = 50,000 mg/L (freshwater fish, 48 h) | ||
| Line 115: | Line 115: | ||
===Physical=== | ===Physical=== | ||
| − | PE is a white crystalline solid, with no smell (if pure). It has a density of 1. | + | PE is a white crystalline solid, with no smell (if pure). It has a density of 1.396 g/cm<sup>3</sup>. PE is slightly soluble in water (5.6 g/100 ml at 15 °C). It is also soluble in [[ethanol]], [[ethylene glycol]], [[formamide]], [[glycerol]], [[methanol]], but insoluble in aprotic organic solvents such as [[acetone]], [[benzene]], [[carbon tetrachloride]], [[chloroform]], [[diethyl ether]], paraffin. |
==Availability== | ==Availability== | ||
| Line 129: | Line 129: | ||
Reacting formaldehyde with 3-hydroxybutanal in the presence of lead(II) hydroxide also yields pentaerythritol.<ref>Zhurnal Russkago Fiziko-Khimicheskago Obshchestva (1913), vol. 45, p. 1452</ref><ref>Chemisches Zentralblatt (1914), vol. 85, nb. I, p. 758</ref> | Reacting formaldehyde with 3-hydroxybutanal in the presence of lead(II) hydroxide also yields pentaerythritol.<ref>Zhurnal Russkago Fiziko-Khimicheskago Obshchestva (1913), vol. 45, p. 1452</ref><ref>Chemisches Zentralblatt (1914), vol. 85, nb. I, p. 758</ref> | ||
| − | It can also be prepared from [[propylene | + | It can also be prepared from [[propylene oxide]].<ref>https://www.google.gg/patents/US20120016049</ref> |
==Projects== | ==Projects== | ||
Latest revision as of 16:15, 2 January 2022
| Names | |
|---|---|
| IUPAC name
2,2-Bis(hydroxymethyl)1,3-propanediol
| |
| Systematic IUPAC name
Pentaerythritol | |
| Other names
Tetramethylolmethane
Hercules Aqualon Hercules P 6 Monopentaerythritol Pentaerythrite Pentek PETP THME | |
| Identifiers | |
| Jmol-3D images | Image |
| |
| Properties | |
| C5H12O4 | |
| Molar mass | 136.15 |
| Appearance | White crystalline solid |
| Odor | Odorless |
| Density | 1.396 g/cm3 |
| Melting point | 260.5 °C (500.9 °F; 533.6 K) |
| Boiling point | 276 °C (529 °F; 549 K) |
| 5.6 g/100 mL (15 °C) | |
| Solubility | Soluble in ethanol, ethylene glycol, formamide, glycerol, isopropanol, methanol Insoluble in acetone, benzene, CCl4, diethyl ether, mineral oil, toluene |
| Vapor pressure | 0.00000008 mmHg (20°C) |
| Hazards | |
| Safety data sheet | Sigma-Aldrich |
| Flash point | 200.1 °C (392.18 °F; 473.25 K) |
| Lethal dose or concentration (LD, LC): | |
| LD50 (Median dose)
|
10,000 mg/kg (rat, oral) |
| LC50 (Median concentration)
|
50,000 mg/L (freshwater fish, 48 h) |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Pentaerythritol (sometimes shortened to PE) is an organic compound with the formula C5H12O4, a polyol with the neopentane backbone. It has no relation to erythritol.
Contents
Properties
Chemical
Pentaerythritol can react with with various halogenated organic compounds to yield many ethers or esters. It can also react with benzaldehyde.
Physical
PE is a white crystalline solid, with no smell (if pure). It has a density of 1.396 g/cm3. PE is slightly soluble in water (5.6 g/100 ml at 15 °C). It is also soluble in ethanol, ethylene glycol, formamide, glycerol, methanol, but insoluble in aprotic organic solvents such as acetone, benzene, carbon tetrachloride, chloroform, diethyl ether, paraffin.
Availability
Pentaerythritol is sold by chemical suppliers. Some products may contain traces of borax as additive.
Certain cosmetics contain a small amount of PE or its derivates.
Preparation
Pentaerythritol can be made by reacting formaldehyde with acetaldehyde, in the presence of a strong base, such as sodium hydroxide, though calcium hydroxide can also be used. A full recipe can be found here.
Acetaldehyde can be replaced with lactonitrile.[1]
Reacting formaldehyde with 3-hydroxybutanal in the presence of lead(II) hydroxide also yields pentaerythritol.[2][3]
It can also be prepared from propylene oxide.[4]
Projects
- Make pentaerythritol tetraacrylate
- Make Pentaerythritol tetranitrate (PETN)
- Make blue aluminium
Handling
Safety
Pentaerythritol is irritant to skin, eyes, nose and mouth. It presents some toxicity if ingested.[5]
Storage
Pentaerythritol should be stored in closed bottles, away from any flame source or oxidizer. Just about any clean bottle is suitable.
Disposal
Pentaerythritol can be safely burned as it releases no toxic byproducts.
References
- ↑ http://www.google.com/patents/US2711431
- ↑ Zhurnal Russkago Fiziko-Khimicheskago Obshchestva (1913), vol. 45, p. 1452
- ↑ Chemisches Zentralblatt (1914), vol. 85, nb. I, p. 758
- ↑ https://www.google.gg/patents/US20120016049
- ↑ http://www.sciencelab.com/msds.php?msdsId=9926416
Relevant Sciencemadness threads
- Chemical pages without CAS Registry Number
- Articles without EBI source
- Chemical pages without ChemSpiderID
- Chemical pages without DrugBank identifier
- Articles without KEGG source
- Articles without InChI source
- Articles without UNII source
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- Chembox articles without image
- Chemical compounds
- Organic compounds
- Alcohols
- Polyols
- Easily prepared chemicals
