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Metol

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(Redirected from Methylaminophenol) Reducing aromatic compound used as developing agent in black and white photography

Metol
Names
IUPAC name 4-(methylamino)phenol sulfate
Other names N-methyl-p-aminophenol sulfate, Pictol, p-(methylamino)phenol sulfate, monomethyl-p-aminophenol hemisulfate, Metol, Elon, Rhodol, Enel, Viterol, Scalol, Genol, Satrapol, Photol.
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.000.216 Edit this at Wikidata
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/2C7H9NO.H2O4S/c2*1-8-6-2-4-7(9)5-3-6;1-5(2,3)4/h2*2-5,8-9H,1H3;(H2,1,2,3,4)Key: ZVNPWFOVUDMGRP-UHFFFAOYSA-N
  • InChI=1/2C7H9NO.H2O4S/c2*1-8-6-2-4-7(9)5-3-6;1-5(2,3)4/h2*2-5,8-9H,1H3;(H2,1,2,3,4)Key: ZVNPWFOVUDMGRP-UHFFFAOYAW
SMILES
  • O=S(=O)(O)O.Oc1ccc(NC)cc1.Oc1ccc(NC)cc1
Properties
Chemical formula (C7H10NO)2SO4
Molar mass 344.38 g/mol
Melting point 260 °C (500 °F; 533 K)
Hazards
GHS labelling:
Pictograms GHS08: Health hazardGHS07: Exclamation markGHS09: Environmental hazard
Signal word Warning
Hazard statements H302, H317, H373, H410
Precautionary statements P260, P280, P301+P312+P330
Safety data sheet (SDS) Oxford MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Metol (or Elon) is a trade name for the organic compound with the formula 2HSO4. It is the sulfate salt of N-methylaminophenol. This colourless salt is a popular photographic developer used in monochrome photography.

Synthesis and degradation

Several methods exist for the preparation of N-methylaminophenol. It arises by decarboxylation of N-4-hydroxyphenylglycine (Glycin). It can be obtained by reaction of hydroquinone with methylamine.

Being an electron-rich arene, metol is readily degraded by hydrogen peroxide.

Application

Metol is an excellent developing agent for most continuous tone developer applications, and it has been widely used in published developer formulas as well as commercial products. However, it is difficult to produce highly concentrated developer solutions using Metol, and therefore most Metol developers are supplied in dry chemical mix. A developer containing both Metol and hydroquinone is called an MQ developer. This combination of agents provides greater developer activity since the rate of development by both agents together is greater than the sum of rates of development by each agent used alone (superadditivity). This combination is very versatile; by varying the quantities of Metol, hydroquinone, and restrainer, and adjusting the pH, the entire range of continuous tone developers can be made. Therefore, this form of Metol replaced most other developing agents except for hydroquinone, Phenidone (which is more recent than Metol), and derivatives of Phenidone. Notable formulas include Eastman Kodak D-76 film developer, D-72 print developer, and D-96 motion picture negative developer.

History

Alfred Bogisch, working for a chemical company owned by Julius Hauff, discovered in 1891 that methylated p-aminophenol has more vigorous developing action than p-aminophenol. Hauff introduced this compound as a developing agent. The exact composition of Bogisch and Hauff's early Metol is unknown, but it was most likely methylated at the ortho position of the benzene ring (p-amino-o-methylphenol), rather than at the amino group. Some time later, Metol came to mean the N-methylated variety, and the o-methylated variety fell out of use. Aktien-Gesellschaft für Anilinfabrikation (AGFA) sold this compound under the trade name Metol, which became by far the most common name, followed by Eastman Kodak's trade name Elon.

Because it has been in use for this purpose for over 100 years, and often by amateur photographers, there is a substantial body of evidence regarding the health problems that contact with Metol can cause. These are principally local dermatitis of the hands and forearms. There is also some evidence of sensitization dermatitis.

References

  1. GHS: GESTIS 022920
  2. Gerd Löbbert "Photography" in Ullmann's Encyclopedia of Industrial Chemistry, 2005, Wiley-VCH, Weinheim. doi:10.1002/14356007.a20_001
  3. Harger, Rolla N. (1919). "Preparation of Metol". J. Am. Chem. Soc. 41 (2): 270–276. doi:10.1021/ja01459a014.
  4. Lunar, L. (2000). "Degradation of Photographic Developers by Fenton's Reagent: Condition Optimization and Kinetics for Metol Oxidation". Water Research. 34 (6): 1791–1802. doi:10.1016/s0043-1354(99)00339-5.
  5. Roberts, David W.; Aptula, Aynur O.; Patlewicz, Grace (2007). "Electrophilic Chemistry Related to Skin Sensitization. Reaction Mechanistic Applicability Domain Classification for a Published Data Set of 106 Chemicals Tested in the Mouse Local Lymph Node Assay". Chemical Research in Toxicology. 20 (1): 44–60. doi:10.1021/tx060121y. PMID 17226926.
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