Difference between revisions of "Oxalyl chloride"
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| Name = Oxalyl chloride | | Name = Oxalyl chloride | ||
| Reference = | | Reference = | ||
| − | | IUPACName = | + | | IUPACName = Oxalyl dichloride |
| PIN = | | PIN = | ||
| − | | SystematicName = | + | | SystematicName = Ethanedioyl dichloride |
| − | | OtherNames = | + | | OtherNames = Oxalic acid chloride<br>Oxalic acid dichloride<br>Oxalic dichloride<br>Oxaloyl chloride |
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| − | + | ||
| − | + | ||
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<!-- Images --> | <!-- Images --> | ||
| ImageFile = | | ImageFile = | ||
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| Section2 = {{Chembox Properties | | Section2 = {{Chembox Properties | ||
| AtmosphericOHRateConstant = | | AtmosphericOHRateConstant = | ||
| − | | Appearance = | + | | Appearance = Colorless liquid |
| BoilingPt = | | BoilingPt = | ||
| − | | BoilingPtC = | + | | BoilingPtC = 63-64 |
| BoilingPt_ref = | | BoilingPt_ref = | ||
| BoilingPt_notes = | | BoilingPt_notes = | ||
| − | | Density = | + | | Density = 1.4785 g/cm<sup>3</sup> |
| − | | Formula = | + | | Formula = C<sub>2</sub>O<sub>2</sub>Cl<sub>2</sub> |
| HenryConstant = | | HenryConstant = | ||
| LogP = | | LogP = | ||
| − | | MolarMass = | + | | MolarMass = 126.93 g/mol |
| MeltingPt = | | MeltingPt = | ||
| − | | MeltingPtC = | + | | MeltingPtC = -16 |
| MeltingPt_ref = | | MeltingPt_ref = | ||
| MeltingPt_notes = | | MeltingPt_notes = | ||
| + | | Odor = Acrid | ||
| pKa = | | pKa = | ||
| pKb = | | pKb = | ||
| − | + | | Solubility = Reacts | |
| − | | Solubility = | + | | SolubleOther = Reacts with alcohols |
| − | | SolubleOther = | + | |
| Solvent = | | Solvent = | ||
| VaporPressure = | | VaporPressure = | ||
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}} | }} | ||
| Section6 = {{Chembox Hazards | | Section6 = {{Chembox Hazards | ||
| − | | AutoignitionPt = | + | | AutoignitionPt = Non-flammable |
| ExploLimits = | | ExploLimits = | ||
| − | | ExternalMSDS = | + | | ExternalMSDS = [https://www.docdroid.net/hVBgMBf/oxalyl-chloride-sa.pdf Sigma-Aldrich] |
| − | | FlashPt = | + | | FlashPt = Non-flammable |
| LD50 = | | LD50 = | ||
| LC50 = | | LC50 = | ||
| − | | MainHazards = | + | | MainHazards = Corrosive |
| NFPA-F = | | NFPA-F = | ||
| NFPA-H = | | NFPA-H = | ||
| Line 110: | Line 105: | ||
| OtherFunction = | | OtherFunction = | ||
| OtherFunction_label = | | OtherFunction_label = | ||
| − | | OtherCompounds = | + | | OtherCompounds = [[Oxalic acid]]<br>[[Thionyl chloride]] |
}} | }} | ||
}} | }} | ||
| − | Oxalyl chloride is the [[acyl chloride]] of [[oxalic acid]]. It is used as a chlorinating agent, similar to [[thionyl chloride]]. Like other acyl chlorides, it is also used for producing derivatives of the parent acid such as [[ | + | '''Oxalyl chloride''' is the [[acyl chloride]] of [[oxalic acid]]. It is used as a chlorinating agent, similar to [[thionyl chloride]]. Like other acyl chlorides, it is also used for producing derivatives of the parent acid such as [[ester]]s. Aromatic esters of oxalic acid are used in glowsticks. |
==Properties== | ==Properties== | ||
===Chemical=== | ===Chemical=== | ||
| − | Oxalyl chloride behaves similarly to other [[acyl | + | Oxalyl chloride behaves similarly to other [[acyl chloride]]s in that reacting with alcohols produces the corresponding [[ester]]. Unusually, however, reaction with water does not yield the parent acid, but instead results in decomposition to [[carbon dioxide]], [[carbon monoxide]], and [[hydrogen chloride]]. |
| − | Other [[carboxylic | + | Other [[carboxylic acid]]s can be converted to the corresponding acyl chloride by treatment with oxalyl chloride in the presence of a catalytic amount of a nitrogen base such as [[dimethylformamide]], [[triethylamine]], or [[pyridine]]. The byproducts produced by this reaction are [[carbon dioxide]] and [[carbon monoxide]]. |
| − | Oxalyl chloride can also be used to formylate [[ | + | Oxalyl chloride can also be used to formylate [[arene]]s by [[Friedel-Crafts acylation]]. |
===Physical=== | ===Physical=== | ||
Revision as of 22:22, 23 March 2019
| Names | |
|---|---|
| IUPAC name
Oxalyl dichloride
| |
| Systematic IUPAC name
Ethanedioyl dichloride | |
| Other names
Oxalic acid chloride
Oxalic acid dichloride Oxalic dichloride Oxaloyl chloride | |
| Properties | |
| C2O2Cl2 | |
| Molar mass | 126.93 g/mol |
| Appearance | Colorless liquid |
| Odor | Acrid |
| Density | 1.4785 g/cm3 |
| Melting point | −16 °C (3 °F; 257 K) |
| Boiling point | 63–64 °C (145–147 °F; 336–337 K) |
| Reacts | |
| Solubility | Reacts with alcohols |
| Hazards | |
| Safety data sheet | Sigma-Aldrich |
| Flash point | Non-flammable |
| Related compounds | |
| Related compounds
|
Oxalic acid Thionyl chloride |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Oxalyl chloride is the acyl chloride of oxalic acid. It is used as a chlorinating agent, similar to thionyl chloride. Like other acyl chlorides, it is also used for producing derivatives of the parent acid such as esters. Aromatic esters of oxalic acid are used in glowsticks.
Contents
Properties
Chemical
Oxalyl chloride behaves similarly to other acyl chlorides in that reacting with alcohols produces the corresponding ester. Unusually, however, reaction with water does not yield the parent acid, but instead results in decomposition to carbon dioxide, carbon monoxide, and hydrogen chloride.
Other carboxylic acids can be converted to the corresponding acyl chloride by treatment with oxalyl chloride in the presence of a catalytic amount of a nitrogen base such as dimethylformamide, triethylamine, or pyridine. The byproducts produced by this reaction are carbon dioxide and carbon monoxide.
Oxalyl chloride can also be used to formylate arenes by Friedel-Crafts acylation.
Physical
Availability
Oxalyl chloride is available from chemical suppliers but due to its hazards it is often hard to get for amateurs.
Preparation
Oxalyl chloride is prepared by reacting anhydrous oxalic acid with phosphorus pentachloride.
Projects
- Make Bis(2,4,6-trichlorophenyl)oxalate for glowsticks
Handling
Safety
Oxalyl chloride is very toxic and presents a severe inhalational hazard. It should only be used with very good ventilation.
Contact with water produces highly toxic carbon monoxide gas, along with corrosive hydrogen chloride.
