Resorcinol
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Names | |||
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Preferred IUPAC name
Benzene-1,3-diol[1] | |||
Other names
Resorcinol[1]
Resorcin m-Dihydroxybenzene 1,3-Benzenediol 1,3-Dihydroxybenzene 3-Hydroxyphenol m-Benzenediol | |||
Identifiers | |||
3D model (
JSmol ) |
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ChEBI | |||
ChEMBL | |||
ChemSpider | |||
ECHA InfoCard
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100.003.260 | ||
KEGG | |||
PubChem CID
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UNII | |||
UN number | 2876 | ||
CompTox Dashboard (EPA)
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Properties | |||
C6H6O2 | |||
Molar mass | 110.111 g/mol | ||
Appearance | White solid[2] | ||
Odor | Faint[2] | ||
Density | 1.28 g/cm3, solid | ||
Melting point | 110 °C (230 °F; 383 K) | ||
Boiling point | 277 °C (531 °F; 550 K) | ||
110 g/100 mL at 20 °C | |||
Vapor pressure | 0.0002 mmHg (25 °C)[2] | ||
Acidity (pKa) | 9.15[3] | ||
−67.26×10−6 cm3/mol | |||
Refractive index (nD)
|
1.578[4] | ||
2.07±0.02 D[5] | |||
Thermochemistry | |||
Std enthalpy of (ΔfH⦵298)formation |
-368.0 kJ·mol−1[4] | ||
Enthalpy of fusion (ΔfH⦵fus)
|
20.4 kJ·mol−1[4] | ||
Pharmacology | |||
D10AX02 (WHO) S01AX06 (WHO) | |||
Hazards | |||
GHS labelling: | |||
H302, H313, H315, H318, H400 | |||
P273, P280, P305+P351+P338 | |||
Flash point | 127 °C; 261 °F; 400 K[2] | ||
608 °C (1,126 °F; 881 K)[4] | |||
Explosive limits
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1.4%-?[2] | ||
NIOSH (US health exposure limits): | |||
PEL (Permissible)
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none[2] | ||
REL (Recommended)
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TWA 10 ppm (45 mg/m3) ST 20 ppm (90 mg/m3)[2] | ||
IDLH (Immediate danger) |
N.D.[2] | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Resorcinol (or resorcin) is a phenolic compound. It is an
Production
Resorcinol is produced in several steps from benzene, starting with dialkylation with
Resorcinol is an expensive chemical, produced in only a very few locations around the world (as of 2010 only four commercial plants were known to be operative: in the United States, Germany, China, and Japan), and as such it is the determining factor in the cost of PRF adhesives.[7] Production in the United States ended in 2017 with the closure of Indspec Chemical's plant in Petrolia, Pennsylvania.[8]
Many additional routes exist for resorcinol. It was formerly produced by disulfonation of benzene followed by hydrolysis of the 1,3-disulfonate. This method has been discarded because it cogenerates so much sulfur-containing waste. Resorcinol can also be produced when any of a large number of
Reactions
Partial
It reduces
Sodium amalgam reduces it to dihydroresorcin, which when heated to 150 to 160 °C with concentrated barium hydroxide solution gives γ-acetylbutyric acid.[citation needed]
When fused with potassium hydroxide, resorcinol yields
With
In presence of Sulfuric acid, with twice amount of Succinic acid, Resorcinol creates Fluorescence effect on water.[17]
In addition to electrophilic aromatic addition, resorcinol (and other
Nitration with concentrated nitric acid in the presence of cold concentrated sulfuric acid yields trinitroresorcin (styphnic acid), an explosive.
Occurrence and use
Derivatives of resorcinol are found in different natural sources.
Adhesives
Resorcinol is mainly used in the production of resins. As a mixture with phenol, it condenses with formaldehyde to afford adhesives. Such resins are used as adhesives in the rubber industry and others are used for wood glue.[6] Related to its conversion resins with formaldehyde, resorcinol is the starting material for resorcinarene rings.
Medical uses
It is present in over-the-counter topical acne treatments at 2% or less concentration, and in prescription treatments at higher concentrations.[19] Monoacetylresorcinol, C6H4(OH)(O–COCH3), is used under the name of Euresol.[20] It is used in hidradenitis suppurativa with limited evidence showing it can help with resolution of the lesions.[21] Resorcinol is one of the active ingredients in products such as Resinol, Vagisil, and Clearasil.
In the 1950s and early 1960s the British Army used it, in the form of a paste applied directly to the skin. One such place where this treatment was given to soldiers with chronic acne was the Cambridge Military Hospital, Aldershot, England. It was not always successful.
Chemical uses
Resorcinol is used as a chemical intermediate for the synthesis of pharmaceuticals and other organic compounds. It is used in the production of
It is an analytical reagent for the qualitative determination of ketoses (Seliwanoff's test).
It is the starting material for the initiating explosive lead styphnate.[22]
Related compounds
Resorcinol is also a common
History, etymology, and nomenclature
Austrian chemist Heinrich Hlasiwetz (1825–1875) is remembered for his chemical analysis of resorcinol and for his part in the first preparation of resorcinol, along with Ludwig Barth, which was published in 1864.[27]: 10 [28]
Benzene-1,3-diol is the name recommended by the International Union of Pure and Applied Chemistry (IUPAC) in its 1993 Recommendations for the Nomenclature of Organic Chemistry.[29]
Resorcinol is so named because of its derivation from ammoniated resin gum, and for its relation to the chemical orcinol.[30]
Toxicity
Resorcinol has low toxicity, with an LD50 (rats, oral) > 300 mg/kg. It is less toxic than phenol.[6]
Resorcinol was named a substance of very high concern under European Union REACH in 2022 because of its endocrine disrupting properties.[31]
References
- ^ ISBN 978-0-85404-182-4.
- ^ a b c d e f g h NIOSH Pocket Guide to Chemical Hazards. "#0543". National Institute for Occupational Safety and Health (NIOSH).
- .
- ^ )
- doi:10.1021/ja01218a051.)
{{cite journal}}
: CS1 maint: multiple names: authors list (link - ^ ISBN 978-3527306732.
- ^ Wood adhesives, Pizzi & Mittal, 2010
- ^ McCoy, Michael. "Resorcinol plant to close". Chemical & Engineering News. American Chemical Society. Retrieved 6 December 2023.
- .
- .
- .
- .
- ^ A. Seyewitz, Bull. Soc. Chins., 1890, 3, p. 811
- .
- ^ J. T. Hewitt and F. G. Pope, Jour. C/tern. Soc., 1897, 75, p. 1084
- .
- ^ PMID 26313262.
- .
- S2CID 1794323.
- ^ Euresol, PubChem
- PMID 31674740.
- ^ "Military Explosives," Department of the Army Technical Manual, TM-9-1300-214 (Washington, D.C.: Department of the Army, September 1984), p. 7-12.
- .
- .
- ^ PMID 23312026.
- PMID 20055425.
- ISBN 9783540280903
- .
- ISBN 978-0-632-03488-8.)
{{cite book}}
: CS1 maint: multiple names: authors list (link - ^ H. Hlasiwetz and L. Barth (1864) "Ueber einen neuen, dem Orcin homologen Körper" (On a new substance homologous to orcin), Annalen der Chemie, 130 (3) : 354-359. Resorcinol is named on p. 358: "Wir nennen den neuen Körper, da wir gefunden haben, dass er auch aus dem Ammoniakgummiharz erhalten werden kann, Resorcin, um an seine Entstehung aus Harzen und seine Beziehung zum Orcin zu erinnern." (We name the new substance, since we have found that it can be obtained from ammoniated resin gum, resorcin, in order to recall its creation from resin and its relation to orcin.)
- ^ "Resorcinol to be added to REACH candidate list after long battle". Chemical Watch. 10 February 2022. Retrieved 16 August 2022.
External links
- International Chemical Safety Card 1033
- NIOSH Pocket Guide to Chemical Hazards
- IARC Monograph: "Resorcinol"
- IUPAC Nomenclature of Organic Chemistry (online version of the "Blue Book")
public domain: Chisholm, Hugh, ed. (1911). "Resorcin". Encyclopædia Britannica. Vol. 23 (11th ed.). Cambridge University Press. pp. 183–184.
This article incorporates text from a publication now in the