Paracetamol: Difference between revisions
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(Created page with "{{Compound|aka=Acetaminophen, Tylenol |chemf=C8H9NO2|mm=151.17|density=1.263|mp=169|sol_aq=12.78 |medicine=yes|listed_who=yes|listed_dhs=yes}} {{med desc|flist=WHO, DHS, and EMS |treats=pain and fever. It is typically used for mild to moderate pain relief |admin=orally}} ==Uses== ===Primary=== * Pharm: used in the medication {{medlink|paracetamol}} on the WHO LEM, WHO IEHK, DHS AMF, and EMS lists ==Production== ===Synthesis=== ====from 4-aminophenol==== The main product...") |
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Combine [[4-nitrophenol]] and '''potassium thioacetate'''.<ref>{{cite pub |last=Bhattacharya |first=Apurba |last2=et al |date=2006 |title=One-step reductive amidation of nitro arenes: application in the synthesis of Acetaminophen |url=http://www.cs.gordon.edu/~ijl/_lead_papers/One%20step%20reductive%20amidation%20of%20nitroarenes%20-%20Tylenol.pdf |publication=Tetrahedron Letters |volume=47 |pages=1861-1864 |doi=10.1016/j.tetlet.2005.09.196 |access-date=2016-11-02 }}</ref> | Combine [[4-nitrophenol]] and '''potassium thioacetate'''.<ref>{{cite pub |last=Bhattacharya |first=Apurba |last2=et al |date=2006 |title=One-step reductive amidation of nitro arenes: application in the synthesis of Acetaminophen |url=http://www.cs.gordon.edu/~ijl/_lead_papers/One%20step%20reductive%20amidation%20of%20nitroarenes%20-%20Tylenol.pdf |publication=Tetrahedron Letters |volume=47 |pages=1861-1864 |doi=10.1016/j.tetlet.2005.09.196 |access-date=2016-11-02 }}</ref> | ||
====from hydroquinone==== | ====from hydroquinone====Benzene-1,4-diol | ||
In 2014 a "one-pot" synthesis from [[ | In 2014 a "one-pot" synthesis from [[Benzene-1,4-diol]] has been described before the Royal Society of Chemistry.<ref>{{cite pub | ||
|title=Amidation of phenol derivatives: a direct synthesis of paracetamol (acetaminophen) from Hydroquinone | |title=Amidation of phenol derivatives: a direct synthesis of paracetamol (acetaminophen) from Hydroquinone | ||
|first1=Roxan | |first1=Roxan | ||
| Line 54: | Line 54: | ||
|url=http://www.rsc.org/suppdata/gc/c4/c4gc00166d/c4gc00166d1.pdf | |url=http://www.rsc.org/suppdata/gc/c4/c4gc00166d/c4gc00166d1.pdf | ||
|courtesy=Royal Society of Chemistry (UK)}}</ref> The process may be summarized as follows: | |courtesy=Royal Society of Chemistry (UK)}}</ref> The process may be summarized as follows: | ||
: [[ | : [[Benzene-1,4-diol]], [[ammonium acetate]], and [[acetic acid]] were mixed in an argon atmosphere and heated slowly to 230 °C. The mixture was stirred at this temperature for 15 hours. After cooling the acetic acid was evaporated and the precipitate was filtered, washed with water and dried to give paracetamol as a white solid. | ||
The authors go on to claim an 88% yield and 99% purity. | The authors go on to claim an 88% yield and 99% purity. | ||
Latest revision as of 09:54, 5 December 2024
| Chemical formula | C8H9NO2 |
|---|---|
| Molar Mass(g/mol) | 151.17 |
| Density(g/cc) | 1.263 |
| Melting Point(°C) | 169 |
| Solubility in water(g/L) | 12.78 |
| NFPA 704 |  0
0
0
|
Paracetamol is included in WHO, DHS, and EMS and is used to treat pain and fever. It is typically used for mild to moderate pain relief. It is usually administered orally.[1]
Uses
Primary
- Pharm: used in the medication paracetamol on the WHO LEM, WHO IEHK, DHS AMF, and EMS lists
Production
Synthesis
from 4-aminophenol
The main production methods differ over the method of acetylation
via acetic anhydride
Paraphrasing from his book[2]
Combine 4-aminophenol with acetic anhydride giving paracetamol
- 2 HO-C6H4-NH2 + (CH3CO)2O → 2 HO-C6H4-NH-COCH3 + H2O
via glacial acetic acid
Intermix the 4-aminophenol and glacial acetic acid at 115-120°C in a refluxing apparatus that distills off the water at the top.[3]
clay-promoted acetylation
Combine 4-aminophenol with glacial acetic acid in an Fe3+ (basic iron acetate?) enriched clay and mix at 160°C for 6 hours [4]
from 4-nitrophenol
The reduction and acylation steps are performed simultaneously
via tin/acid
Combine acetic acid, tin, and 4-nitrophenol
- O2NC6H4OH + 5 CH3COOH + 2 Sn → CH3COONHC6H4OH + 2 H2O + 2 Sn(CH3COO)2
via thioacetates
Combine 4-nitrophenol and potassium thioacetate.[5]
====from hydroquinone====Benzene-1,4-diol In 2014 a "one-pot" synthesis from Benzene-1,4-diol has been described before the Royal Society of Chemistry.[6] The process may be summarized as follows:
- Benzene-1,4-diol, ammonium acetate, and acetic acid were mixed in an argon atmosphere and heated slowly to 230 °C. The mixture was stirred at this temperature for 15 hours. After cooling the acetic acid was evaporated and the precipitate was filtered, washed with water and dried to give paracetamol as a white solid.
The authors go on to claim an 88% yield and 99% purity.
See Also
References
- ↑ Wikipedia page
- ↑ Ellis, Frank (2002) "Paracetamol: a curriculum resource".
Royal Society of Chemistry, Cambridge, UK
ISBN: 0-85404-375-6 - ↑ US patent 9102589 "Reactive distillation process for preparation of acetaminophen", 2010
Link courtesy Google - ↑ US patent 6215024B1 "Process for the production of amides from amines", 1999
Link courtesy Google - ↑ "One-step reductive amidation of nitro arenes: application in the synthesis of Acetaminophen"
Tetrahedron Letters 47; pp1861-1864.
DOI:10.1016/j.tetlet.2005.09.196 - ↑ Joncour, Roxan; Duguet, Nicolas; Métay, Estelle; Ferreira, Amadéo; Lemaire, Marc (2014) "Amidation of phenol derivatives: a direct synthesis of paracetamol (acetaminophen) from Hydroquinone"
Green Chem. 16(6); pp2997–3002.
DOI:10.1039/C4GC00166D
link courtesy Royal Society of Chemistry (UK).