Resorcinol

Source: Wikipedia, the free encyclopedia.

Resorcinol
Skeletal formula
Skeletal formula
Ball-and-stick model
Ball-and-stick model
Names
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
)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard
100.003.260 Edit this at Wikidata
KEGG
UNII
UN number 2876
  • InChI=1S/C6H6O2/c7-5-2-1-3-6(8)4-5/h1-4,7-8H checkY
    Key: GHMLBKRAJCXXBS-UHFFFAOYSA-N checkY
  • InChI=1/C6H6O2/c7-5-2-1-3-6(8)4-5/h1-4,7-8H
    Key: GHMLBKRAJCXXBS-UHFFFAOYAB
  • c1cc(cc(c1)O)O
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
1.578[4]
2.07±0.02 D[5]
Thermochemistry
Std enthalpy of
formation
fH298)
-368.0 kJ·mol−1[4]
Enthalpy of fusion fHfus)
20.4 kJ·mol−1[4]
Pharmacology
D10AX02 (WHO) S01AX06 (WHO)
Hazards
GHS labelling:
GHS05: CorrosiveGHS07: Exclamation markGHS09: Environmental hazard
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
1.4%-?[2]
NIOSH (US health exposure limits):
PEL (Permissible)
none[2]
REL (Recommended)
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).
☒N verify (what is checkY☒N ?)

Resorcinol (or resorcin) is a phenolic compound. It is an

benzenediols, the 1,3-isomer (or meta-isomer). Resorcinol crystallizes from benzene as colorless needles that are readily soluble in water, alcohol, and ether, but insoluble in chloroform and carbon disulfide.[6]

Production

Resorcinol is produced in several steps from benzene, starting with dialkylation with

Hock rearrangement of this disubstituted arene gives acetone and resorcinol.[6]

Production of resorcinol via Hock Rearrangement

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

bromophenols
, benzene-para-disulfonic acid) also yield resorcinol on fusion with potassium hydroxide.

Reactions

Partial

dihydroresorcinol, also known as 1,3-cyclohexanedione.[10][11]

It reduces

pyrocatechol. Iron(III) chloride colors its aqueous solution a dark-violet, and bromine water precipitates tribromoresorcinol. These properties are what give it its use as a colouring agent for certain chromatography
experiments.

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

anhydrides of dibasic acids, it yields fluoresceins. When heated with calcium chlorideammonia to 200 °C it yields meta-dioxydiphenylamine.[13]

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

enone tautomer
.

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.

pseudotannins in plants.[17]

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.

throat lozenges
.

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

UV
absorber in resins.

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

dyestuff
under the name of Fluorescent Resorcin Blue.

deliquescent mass obtained by the action of sulfuric acid on resorcin.[24] It is readily soluble in water and ethanol
.

Resorcinol is also a common

drug target for anticancer treatments.[25]

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

  1. ^ .
  2. ^ a b c d e f g h NIOSH Pocket Guide to Chemical Hazards. "#0543". National Institute for Occupational Safety and Health (NIOSH).
  3. .
  4. ^
    OCLC 930681942.{{cite book}}: CS1 maint: location missing publisher (link) CS1 maint: others (link
    )
  5. doi:10.1021/ja01218a051.{{cite journal}}: CS1 maint: multiple names: authors list (link
    )
  6. ^ .
  7. ^ Wood adhesives, Pizzi & Mittal, 2010
  8. ^ McCoy, Michael. "Resorcinol plant to close". Chemical & Engineering News. American Chemical Society. Retrieved 6 December 2023.
  9. .
  10. .
  11. .
  12. .
  13. ^ A. Seyewitz, Bull. Soc. Chins., 1890, 3, p. 811
  14. .
  15. ^ J. T. Hewitt and F. G. Pope, Jour. C/tern. Soc., 1897, 75, p. 1084
  16. .
  17. ^ .
  18. .
  19. .
  20. ^ Euresol, PubChem
  21. PMID 31674740
    .
  22. ^ "Military Explosives," Department of the Army Technical Manual, TM-9-1300-214 (Washington, D.C.: Department of the Army, September 1984), p. 7-12.
  23. .
  24. .
  25. ^ .
  26. .
  27. .
  28. ISBN 978-0-632-03488-8.{{cite book}}: CS1 maint: multiple names: authors list (link
    )
  29. ^ 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.)
  30. ^ "Resorcinol to be added to REACH candidate list after long battle". Chemical Watch. 10 February 2022. Retrieved 16 August 2022.

External links

 This article incorporates text from a publication now in the public domainChisholm, Hugh, ed. (1911). "Resorcin". Encyclopædia Britannica. Vol. 23 (11th ed.). Cambridge University Press. pp. 183–184.