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{{Short description|Group of isomers}}
'''Xylidine''' can refer to any of the six [[isomer]]s of [[xylene]] [[amine]], or any mixture of them. All isomers are toxic.
'''Xylidine''' can refer to any of the six [[isomer]]s of [[xylene]] [[amine]], or any mixture of them.


The chemical formula of xylidines is C<sub>8</sub>H<sub>11</sub>N, or (CH<sub>3</sub>)<sub>2</sub>C<sub>6</sub>H<sub>3</sub>NH<sub>2</sub>. They are stable and combustible and react with strong oxidizing agents. They may be light sensitive. The CAS number for the isomer mixture is {{CASREF|CAS=1300-73-8}}. They are typically yellow liquids (except 3,4-xylidine which is solid) that darken when exposed to air and light. They are miscible with [[ethanol]] and [[diethyl ether]] and little soluble in water.
The chemical formula of xylidines is C<sub>8</sub>H<sub>11</sub>N or, more descriptively, (CH<sub>3</sub>)<sub>2</sub>C<sub>6</sub>H<sub>3</sub>NH<sub>2</sub>. The CAS number for the isomer mixture is {{CASREF|CAS=1300-73-8}}. They are colorless solids or liquids, although commercial samples can appear yellow or darker. They are miscible with [[ethanol]] and [[diethyl ether]] and slightly soluble in water. Xylidines are used in production of [[pigment]]s and [[dye]]stuffs, and various [[antioxidant]]s, [[agrochemical]]s, pharmaceuticals, [[hypergolic propellant]]s, and many other organic chemicals.<ref name=Ullmann>{{cite encyclopedia|author=M. Meyer|title=Xylidines|encyclopedia=Ullmann's Encyclopedia of Industrial Chemistry|publisher=Wiley-VCH|place=Weinheim|year=2012|doi=10.1002/14356007.a28_455}}</ref>


In [[World War II]], xylidine was an important [[antiknock agent]] in very high performance aviation gasolines. Its purpose was to permit high levels of boost pressure in multiple-stage turbochargers, and thus high power at high altitudes, without causing detonation that would destroy the engine. The high pressures brought high temperatures of inlet air, making engines prone to knock. This use and storage stabilization methods were important military secrets.<ref>{{cite web |last1=Meyer |first1=Carl L. |title=Antiknock effectiveness of xylidine in small-scale engines |url=https://ntrs.nasa.gov/citations/19930093446 |website=U.S. NASA NTRS |publisher=U.S. Government, NASA |access-date=2 February 2022}}</ref><ref>{{cite web |last1=Starr |first1=Charles E Jr. |display-authors=etal |title=Method of stabilizing xylidine, U.S. Patent No 2,509,891 |url=https://patentimages.storage.googleapis.com/0c/53/cc/4e620bb187e994/US2509891.pdf |website=Google Patents |publisher=U.S. Patent Office |access-date=2 February 2022}}</ref>
Xylidines are produced as byproducts of [[fractional distillation]] of [[coal tar]].


⚫
==Isomers of xylidine==
Their risk and safety phrases are {{R20}} {{R22}} {{R36}} {{R37}} {{R38}}.
⚫
<gallery>

⚫
Image:2,3-Xylidin.svg|2,3-xylidine
Xylidines are chiefly used in production of [[pigment]]s and [[dye]]stuffs, and also various [[antioxidant]]s, [[agrochemical]]s, pharmaceuticals, and many other organic chemicals.
⚫
Image:2,4-Xylidin.svg|2,4-xylidine
⚫
Image:2,5-Xylidin.svg|2,5-xylidine
⚫
Image:2,6-Xylidin.svg|2,6-xylidine
⚫
Image:3,4-Xylidin.svg|3,4-xylidine
⚫
Image:3,5-Xylidin.svg|3,5-xylidine
⚫
</gallery>


===2,3-xylidine===
Xylidines are also used as a component of the [[Tonka (fuel)|Tonka rocket fuel]].
{{main|2,3-Xylidine}}
⚫
'''2,3-xylidine''', also called '''o-xylidine''', '''2,3-dimethylaniline''', '''2,3-xylylamine''', or '''2,3-dimethylphenylamine''', is a liquid with melting point 2.5&nbsp;°C and boiling point 222&nbsp;°C, and [[flash point]] at 96&nbsp;°C. {{SMILESCAS|CAS=87-59-2|SMILES=Nc1cccc(C)c1C}} It is used in production of [[mefenamic acid]], dyes, and pesticides.


==2,3-xylidine==
===2,4-xylidine===
⚫
'''2,3-xylidine''', also called '''o-xylidine''', '''2,3-dimethylaniline''', '''2,3-xylylamine''', or '''2,3-dimethylphenylamine''', is a liquid with melting point 2.5 °C and boiling point 222 °C, and [[flash point]] at 96 °C. {{SMILESCAS|CAS=87-59-2|SMILES=Nc1cccc(C)c1C}} It is used in production of [[mefenamic acid]], dyes, and pesticides.

⚫
==2,4-xylidine==
{{main|2,4-Xylidine}}
{{main|2,4-Xylidine}}
'''2,4-xylidine''', also called '''2-methyl-p-toluidine''', '''2,4-dimethylaniline''', '''2,4-xylylamine''', or '''2,4-dimethylphenylamine''', is a liquid with melting point 16 °C, boiling point 217 °C, and [[flash point]] at 90 °C. {{SMILESCAS|CAS=95-68-1|SMILES=Nc1ccc(C)cc1C}} It is used for production of pesticides, dyes, and other chemicals.
'''2,4-xylidine''', also called '''2-methyl-p-toluidine''', '''2,4-dimethylaniline''', '''2,4-xylylamine''', or '''2,4-dimethylphenylamine''', is a liquid with melting point 16&nbsp;°C, boiling point 217&nbsp;°C, and [[flash point]] at 90&nbsp;°C. {{SMILESCAS|CAS=95-68-1|SMILES=Nc1ccc(C)cc1C}} It is used for production of pesticides, dyes, and other chemicals.


==2,5-xylidine==
===2,5-xylidine===
{{main|2,5-Xylidine}}
'''2,5-xylidine''', also called '''p-xylidine''', '''2,5-dimethylaniline''', '''2,5-xylylamine''', or '''2,5-dimethylphenylamine''', is a liquid with melting point 11.5 °C and boiling point 215 °C. {{SMILESCAS|CAS=95-78-3|SMILES=Nc1cc(C)ccc1C}} It is used for production of dyes and other chemicals.
'''2,5-xylidine''', also called '''p-xylidine''', '''2,5-dimethylaniline''', '''2,5-xylylamine''', or '''2,5-dimethylphenylamine''', is a liquid with melting point 11.5&nbsp;°C and boiling point 215&nbsp;°C. {{SMILESCAS|CAS=95-78-3|SMILES=Nc1cc(C)ccc1C}} It is used for production of dyes and other chemicals.


==2,6-xylidine==
===2,6-xylidine===
{{main|2,6-Xylidine}}
{{main|2,6-Xylidine}}
'''2,6-Xylidine''', also called '''2,6-dimethylaniline''', '''2,6-xylylamine''', or '''2,6-dimethylphenylamine''', is a liquid with melting point 8.4 °C and boiling point 216 °C. {{SMILESCAS|CAS=87-62-7|SMILES=Nc1c(C)cccc1C}} It is used in production of some anesthetics and other chemicals.
'''2,6-Xylidine''', also called '''2,6-dimethylaniline''', '''2,6-xylylamine''', or '''2,6-dimethylphenylamine''', is a liquid with melting point 8.4&nbsp;°C and boiling point 216&nbsp;°C. {{SMILESCAS|CAS=87-62-7|SMILES=Nc1c(C)cccc1C}} It is used in production of some anesthetics and other chemicals.


==3,4-xylidine==
===3,4-xylidine===
{{main|3,4-Xylidine}}
{{main|3,4-Xylidine}}
'''3,4-xylidine''', also called '''3,4-dimethylaniline''', '''3,4-xylylamine''', or '''3,4-dimethylphenylamine''', is a crystalline solid with melting point 51 °C and boiling point 226 °C. {{SMILESCAS|CAS=95-64-7|SMILES=Nc1ccc(C)c(C)c1}} It is used as a raw material for production of [[vitamin B2|vitamin B<sub>2</sub>]], dyes, pesticides, and other chemicals.
'''3,4-xylidine''', also called '''3,4-dimethylaniline''', '''3,4-xylylamine''', or '''3,4-dimethylphenylamine''', is a crystalline solid with melting point 51&nbsp;°C and boiling point 226&nbsp;°C. {{SMILESCAS|CAS=95-64-7|SMILES=Nc1ccc(C)c(C)c1}} It is used as a raw material for production of [[vitamin B2|vitamin B<sub>2</sub>]], dyes, pesticides, and other chemicals.


== 3,5-xylidine ==
=== 3,5-xylidine ===
{{main|3,5-Xylidine}}
'''3,5-xylidine''', also called '''3,5-dimethylaniline''', '''3,5-xylylamine''', or '''3,5-dimethylphenylamine''', is a liquid with melting point 9.8 °C and boiling point 220–221 °C. {{SMILESCAS|CAS=108-69-0|SMILES=Nc1cc(C)cc(C)c1}} It is used for production of pesticides, dyes, and other chemicals.
'''3,5-xylidine''', also called '''3,5-dimethylaniline''', '''3,5-xylylamine''', or '''3,5-dimethylphenylamine''', is a liquid with melting point 9.8&nbsp;°C and boiling point 220–221&nbsp;°C. {{SMILESCAS|CAS=108-69-0|SMILES=Nc1cc(C)cc(C)c1}} It is used for production of pesticides, dyes, and other chemicals.


== Safety ==
⚫
<gallery>
The U.S. [[Occupational Safety and Health Administration]] (OSHA) has set the legal limit ([[Permissible exposure limit]]) for xylidine exposure in the workplace as 5 ppm (25&nbsp;mg/m<sup>3</sup>) skin exposure over an eight-hour workday. The U.S. [[National Institute for Occupational Safety and Health]] (NIOSH) has set a [[Recommended exposure limit]] (REL) of 2 ppm (10&nbsp;mg/m<sup>3</sup>) skin exposure over an eight-hour workday. At levels of 50 ppm, xylidine is [[IDLH|immediately dangerous to life and health]].<ref>{{Cite web|title = CDC - NIOSH Pocket Guide to Chemical Hazards - Xylidine|url = https://www.cdc.gov/niosh/npg/npgd0672.html|website = www.cdc.gov|access-date = 2015-11-28}}</ref>
⚫
Image:2,3-Xylidin.svg|2,3-xylidine

⚫
Image:2,4-Xylidin.svg|2,4-xylidine
Their hazard and precaution phrases are {{H-phrases|302|312|315|332|335|351|411}} {{P-phrases|201|202|261|264|270|271|273|280|281|301+312|302+352|304+312|304+340|308+313|312|321|322|330|332+313|362|363|391|403+233|405|501}}.
⚫
Image:2,5-Xylidin.svg|2,5-xylidine

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Image:2,6-Xylidin.svg|2,6-xylidine
==External links==
⚫
Image:3,4-Xylidin.svg|3,4-xylidine
*[https://www.cdc.gov/niosh/npg/npgd0672.html CDC - NIOSH Pocket Guide to Chemical Hazards]
⚫
Image:3,5-Xylidin.svg|3,5-xylidine

⚫
</gallery>
==References==
{{Reflist}}


{{Authority control}}
[[Category:Aromatic amines]]


[[de:Xylidine]]
[[Category:Anilines]]
[[Category:Alkyl-substituted benzenes]]
[[fr:Xylidine]]
[[nl:Xylidine]]
[[zh:二甲基苯胺]]

Latest revision as of 21:56, 2 November 2023

Xylidine can refer to any of the six isomers of xylene amine, or any mixture of them.

The chemical formula of xylidines is C8H11N or, more descriptively, (CH3)2C6H3NH2. The CAS number for the isomer mixture is 1300-73-8. They are colorless solids or liquids, although commercial samples can appear yellow or darker. They are miscible with ethanol and diethyl ether and slightly soluble in water. Xylidines are used in production of pigments and dyestuffs, and various antioxidants, agrochemicals, pharmaceuticals, hypergolic propellants, and many other organic chemicals.[1]

In World War II, xylidine was an important antiknock agent in very high performance aviation gasolines. Its purpose was to permit high levels of boost pressure in multiple-stage turbochargers, and thus high power at high altitudes, without causing detonation that would destroy the engine. The high pressures brought high temperatures of inlet air, making engines prone to knock. This use and storage stabilization methods were important military secrets.[2][3]

Isomers of xylidine

[edit]
  • 2,3-xylidine
    2,3-xylidine
  • 2,4-xylidine
    2,4-xylidine
  • 2,5-xylidine
    2,5-xylidine
  • 2,6-xylidine
    2,6-xylidine
  • 3,4-xylidine
    3,4-xylidine
  • 3,5-xylidine
    3,5-xylidine

2,3-xylidine

[edit]
Main article: 2,3-Xylidine

2,3-xylidine, also called o-xylidine, 2,3-dimethylaniline, 2,3-xylylamine, or 2,3-dimethylphenylamine, is a liquid with melting point 2.5 °C and boiling point 222 °C, and flash point at 96 °C. Its CAS number is 87-59-2 and its SMILES structure is Nc1cccc(C)c1C. It is used in production of mefenamic acid, dyes, and pesticides.

2,4-xylidine

[edit]
Main article: 2,4-Xylidine

2,4-xylidine, also called 2-methyl-p-toluidine, 2,4-dimethylaniline, 2,4-xylylamine, or 2,4-dimethylphenylamine, is a liquid with melting point 16 °C, boiling point 217 °C, and flash point at 90 °C. Its CAS number is 95-68-1 and its SMILES structure is Nc1ccc(C)cc1C. It is used for production of pesticides, dyes, and other chemicals.

2,5-xylidine

[edit]
Main article: 2,5-Xylidine

2,5-xylidine, also called p-xylidine, 2,5-dimethylaniline, 2,5-xylylamine, or 2,5-dimethylphenylamine, is a liquid with melting point 11.5 °C and boiling point 215 °C. Its CAS number is 95-78-3 and its SMILES structure is Nc1cc(C)ccc1C. It is used for production of dyes and other chemicals.

2,6-xylidine

[edit]
Main article: 2,6-Xylidine

2,6-Xylidine, also called 2,6-dimethylaniline, 2,6-xylylamine, or 2,6-dimethylphenylamine, is a liquid with melting point 8.4 °C and boiling point 216 °C. Its CAS number is 87-62-7 and its SMILES structure is Nc1c(C)cccc1C. It is used in production of some anesthetics and other chemicals.

3,4-xylidine

[edit]
Main article: 3,4-Xylidine

3,4-xylidine, also called 3,4-dimethylaniline, 3,4-xylylamine, or 3,4-dimethylphenylamine, is a crystalline solid with melting point 51 °C and boiling point 226 °C. Its CAS number is 95-64-7 and its SMILES structure is Nc1ccc(C)c(C)c1. It is used as a raw material for production of vitamin B2, dyes, pesticides, and other chemicals.

3,5-xylidine

[edit]
Main article: 3,5-Xylidine

3,5-xylidine, also called 3,5-dimethylaniline, 3,5-xylylamine, or 3,5-dimethylphenylamine, is a liquid with melting point 9.8 °C and boiling point 220–221 °C. Its CAS number is 108-69-0 and its SMILES structure is Nc1cc(C)cc(C)c1. It is used for production of pesticides, dyes, and other chemicals.

Safety

[edit]

The U.S. Occupational Safety and Health Administration (OSHA) has set the legal limit (Permissible exposure limit) for xylidine exposure in the workplace as 5 ppm (25 mg/m3) skin exposure over an eight-hour workday. The U.S. National Institute for Occupational Safety and Health (NIOSH) has set a Recommended exposure limit (REL) of 2 ppm (10 mg/m3) skin exposure over an eight-hour workday. At levels of 50 ppm, xylidine is immediately dangerous to life and health.[4]

Their hazard and precaution phrases are H302, H312, H315, H332, H335, H351, H411 P201, P202, P261, P264, P270, P271, P273, P280, P281, P301+P312, P302+P352, P304+P312, P304+P340, P308+P313, P312, P321, P322, P330, P332+P313, P362, P363, P391, P403+P233, P405, P501.

[edit]

References

[edit]
  1. ^ M. Meyer (2012). "Xylidines". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a28_455.
  2. ^ Meyer, Carl L. "Antiknock effectiveness of xylidine in small-scale engines". U.S. NASA NTRS. U.S. Government, NASA. Retrieved 2 February 2022.
  3. ^ Starr, Charles E Jr.; et al. "Method of stabilizing xylidine, U.S. Patent No 2,509,891" (PDF). Google Patents. U.S. Patent Office. Retrieved 2 February 2022.
  4. ^ "CDC - NIOSH Pocket Guide to Chemical Hazards - Xylidine". www.cdc.gov. Retrieved 2015-11-28.
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