Anthracene
Anthracene is a polycyclic aromatic hydrocarbon consisting of three fused benzene rings. It is a solid, colorless compound with a distinct blue fluorescence when exposed to ultraviolet light. Anthracene is used in the production of dyes, as a starting material for the synthesis of various organic compounds, and in research as a fluorescent tracer.
4 Key excerpts on "Anthracene"
eBook - ePubBiochemistry
An Organic Chemistry Approach
- Michael B. Smith(Author)
- 2020(Publication Date)
- CRC Press(Publisher)
...Reprinted with permission from Widersten, M.; Björnestedt, R.; Mannervik, B. Biochemistry 1996, 35, 7731–7742. Copyright 1996 American Chemical Society. 9.10 Polynuclear Aromatic Hydrocarbons There are many aromatic compounds that meet the 4 n +2 rule, with structures where the π-electrons are not confined to one ring, but rather contained in several rings that are fused together. They are called polynuclear (or polycyclic) aromatic molecules. Three simple examples are shown: naphthalene, Anthracene, and phenanthrene. Naphthalene is a bicyclic aromatic compound with the formula C 10 H 8. It was the main constituent of “mothballs” for many years, but toxicity led to its replacement with 1,4-dichlorobenzene (characterized as an insecticidal fumigant). Anthracene is a polycyclic aromatic compound (14 π-electrons) with three rings are fused together and the formula C 14 H 10. Anthracene is used to prepare other important compounds and is used in wood preservatives and in insecticides. Phenanthrene is an isomer of Anthracene in which the point of attachment of the “third ring” on the “middle ring” is different. Like Anthracene, phenanthrene is derived from coal tar and is used in the synthesis of dyes, explosives, and drugs. Polynuclear aromatic hydrocarbons (e.g., naphthalene, Anthracene, and phenanthrene) undergo electrophilic aromatic substitution reactions in the same manner as benzene. A significant difference is that there are more carbon atoms, more potential sites for substitution, and more resonance structures to consider in the arenium ion intermediates. The reaction of naphthalene with Cl 2 /AlCl 3 gave 1-chloronaphthalene as the major product, one of only two different positions for substitution, C1 and C2...
eBook - ePubHandbook of Environmental Analysis
Chemical Pollutants in Air, Water, Soil, and Solid Wastes, Third Edition
- Pradyot Patnaik(Author)
- 2017(Publication Date)
- CRC Press(Publisher)
...37 Hydrocarbons, Polynuclear Aromatic PAHs are aromatic compounds that contain two or more benzene rings that are fused together. These substances may be analyzed by HPLC, GC, GC/MS, and enzyme immunoassay techniques. The latter is a rapid screening method that may be applied for a qualitative or semiquantitative determination. Test kits are commercially available for such screening. The U.S. EPA (1995) has specified a method (Draft Method 4035) that detects a range of PAHs to different degrees and measures the composite of individual responses to determine the total PAHs in the sample. The U.S. EPA has listed 16 PAHs as priority pollutants in wastewater and 24 PAH in the category of soils, sediments, hazardous wastes, and groundwater. Some common PAH compounds including the ones listed by the U.S. EPA as priority pollutants are presented in Table 37.1. All these analytes, as well as any other compound that has a polyaromatic ring, may be analyzed by similar methods. The analytical steps include extraction of the sample with methylene chloride or an appropriate solvent, concentration of the solvent extract into a small volume, cleanup of the extract using silica gel (for dirty samples), and determination of PAH by HPLC, GC, or GC/MS. The HPLC method is superior to packed column GC analysis that suffers from a coelution problem. Table 37.1 Common PAHs CAS. No. Compounds [83-32-9] Acenaphthene [208-96-8] Acenaphthylene [120-12-7] Anthracene [53-96-3] 2-Acetylaminofluorene [56-55-3] Benz(a)Anthracene [205-99-2] Benzo(b)fluoranthene [207-08-9] Benzo(k)fluoranthene [191-24-2] Benzo(g, h, i)perylene [50-32-8] Benzo(a)pyrene [192-97-2] Benzo(e)pyrene [90-13-1] 1-Chloronaphthalene [91-58-7] 2-Chloronaphthalene [218-01-9] Chrysene [191-07-1] Coronene a [224-42-0] Dibenz(a, j)acridine [53-70-3] Dibenz(a, h)Anthracene [132-64-9] Dibenzofuran [192-65-4] Dibenzo(a, e[--=P...
- Robert Routledge(Author)
- 2018(Publication Date)
- Routledge(Publisher)
...Certainly no one could have supposed at that time that the slightest relation existed between Anthracene and madder. Anthracene is a white solid hydro-carbon, which comes over only in the last stages of the distillation of coal-tar, accompanied by naphthaline, from which it is easily separated by means of spirits of wine, by which the naphthaline is readily dissolved, but the Anthracene scarcely. Anderson, ïn 1861, discovered, among other results, that Anthracene, C 14 H 10, by treatment with nitric acid became changed into oxy-Anthracene, C 14 H 8 0 2 ; and this reaction we shall see is a step in the process of procuring alizarine from Anthracene. Phenol, as already mentioned, can be made to yield benzol, by a process of deoxidization. With a view to similarly obtaining a hydro-carbon from alizarine, Graebe and Liebermann passed its vapours over heated zinc filings, and thus produced Anthracene from alizarine. It now remained to find a means of reversing this process, that is, so to act on Anthracene as to produce alizarine, and this was effected by treating Anthracene with bromine, forming a substance which, on fusing with caustic potash, yielded alizar ate of potash, from which pure alizarine resulted by treatment with hydrochloric acid. A much cheaper method was, however, necessary for manufacturing purposes, and it was found in a process by which oxy-Anthracene, C 14 0 8 H 2, is treated at a high temperature with strong sulphuric acid, and the product so formed heated with a strong solution of potash, yielding alizarate of potassium as before. Many other interesting substances appear to be formed in the reactions, but the nature of these bodies has as yet been imperfectly investigated. No doubt whatever can be entertained of the identity of natural with artificial alizarine; and the production of this substance, the first instance of a natural colouring matter made artificially, may be regarded as a great triumph of chemical science...
eBook - ePub- W.L.F. Armarego(Author)
- 2017(Publication Date)
- Butterworth-Heinemann(Publisher)
...Anthracene has been crystallised from EtOH, chromatographed through alumina in hot *benzene (fume hood) and then sublimed in a vacuum in a pyrex tube that has been cleaned and baked at 100°. (For further details see Craig & Rajikan JCS Faraday Trans 2, 74 292 1978, DOI: 10.1039/F29787400292; and Williams & Zboinski JCS Faraday Trans 1 74 618 1978, DOI: 10.1039/F29787400618.) It has been chromatographed on alumina, recrystallised from n- hexane and sublimed under reduced pressure. [Saltiel J Am Chem Soc 108 2674 1986, DOI: 10.1021/ja00270a028; Masnovi et al. J Am Chem Soc 108 1126 1986, DOI: 10.1021/ja00266a003.] Alternatively, recrystallise it from cyclohexane, chromatograph it on alumina with n- hexane as eluent, and recrystallise two more times [Saltiel et al. J Am Chem Soc 109 1209 1987, DOI: 10.1021/ja00238a034]. Anthracene is fluorescent and forms a picrate complex, m 139°, on mixing the components in CHCl 3 or *C 6 H 6, but decomposes on attempted crystallisation. [ Beilstein 5 IV 2281.] Anthracene-9-carboxylic acid (anthroic acid) [723-62-6] C 15 H 10 O 2, M 222.2, m 213-217°, 214°(dec), pK 20 3.65. Crystallise the acid from EtOH. It is fluorescent in EtOH with λ max at 254nm (0.1% EtOH). The corresponding alcohol 9-Anthracenemethanol [1468-95-7] C 15 H 12 O, M 208.3, has m 162-164° (from MeOH); and the respective methacrylate ester 9-anthracenylmethyl methacrylate [31645-35-9] C 19 H 16 O 2, M 276.3, has m 80-85° [from *C 6 H 6 /petroleum ether (b 40-60°) and λ max at 249nm (EtOH).] [ Beilstein 9 IV 2671.] 9-Anthraldehyde (Anthracene-9-carboxaldehyde) [642-31-9] C 15 H 10 O, M 206.2, m 103-105°, 104-105°. Crystallise the aldehyde from acetic acid or EtOH. It forms a charge-transfer complex with TCNE (tetracyanoethylene) in CHCl 3...
