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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<!-- Images --> | <!-- Images --> | ||
| ImageFile = | | ImageFile = | ||
| Line 52: | Line 47: | ||
| 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, amines, [[carboxylic acid]]s |
| − | | SolubleOther = | + | |
| Solvent = | | Solvent = | ||
| VaporPressure = | | VaporPressure = | ||
| Line 93: | Line 88: | ||
}} | }} | ||
| 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]]. |
| − | + | : C<sub>2</sub>O<sub>2</sub>Cl<sub>2</sub> + H<sub>2</sub>O → 2 HCl + CO<sub>2</sub> + CO | |
| − | Oxalyl chloride can also be used to formylate [[ | + | 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 [[arene]]s by [[Friedel-Crafts_reaction#Friedel-Crafts_acylation|Friedel-Crafts acylation]]. | ||
===Physical=== | ===Physical=== | ||
| Line 130: | Line 127: | ||
==Preparation== | ==Preparation== | ||
| − | Oxalyl chloride is prepared by reacting [[anhydrous]] [[oxalic acid]] with [[phosphorus pentachloride]]. | + | Oxalyl chloride is usually prepared by reacting [[anhydrous]] [[oxalic acid]] with [[phosphorus pentachloride]]. Unusually, [[thionyl chloride]] cannot be used to chlorinate oxalic acid. |
==Projects== | ==Projects== | ||
| Line 136: | Line 133: | ||
==Handling== | ==Handling== | ||
| − | |||
===Safety=== | ===Safety=== | ||
Oxalyl chloride is very toxic and presents a severe inhalational hazard. It should only be used with very good ventilation. | Oxalyl chloride is very toxic and presents a severe inhalational hazard. It should only be used with very good ventilation. | ||
| Line 143: | Line 139: | ||
===Storage=== | ===Storage=== | ||
| + | In airtight bottles. | ||
===Disposal=== | ===Disposal=== | ||
| + | Should be dissolved in an excess calcium hydroxide solution, which will cause calcium oxalate to precipitate. | ||
==References== | ==References== | ||
| Line 151: | Line 149: | ||
[[Category:Chemical compounds]] | [[Category:Chemical compounds]] | ||
| + | [[Category:Inorganic compounds]] | ||
[[Category:Chlorine compounds]] | [[Category:Chlorine compounds]] | ||
[[Category:Materials that react with water]] | [[Category:Materials that react with water]] | ||
| Line 156: | Line 155: | ||
[[Category:Irritants]] | [[Category:Irritants]] | ||
[[Category:Chlorinating agents]] | [[Category:Chlorinating agents]] | ||
| + | [[Category:Liquids]] | ||
Latest revision as of 21:47, 11 October 2022
| 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, amines, carboxylic acids |
| 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.
- C2O2Cl2 + H2O → 2 HCl + CO2 + CO
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 usually prepared by reacting anhydrous oxalic acid with phosphorus pentachloride. Unusually, thionyl chloride cannot be used to chlorinate oxalic acid.
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.
Storage
In airtight bottles.
Disposal
Should be dissolved in an excess calcium hydroxide solution, which will cause calcium oxalate to precipitate.
