Antrasena

Antracena
Skeletal formula and numbering system of anthracene
Ball-and-stick model of the anthracene molecule
Anthracene
Nama
Nama IUPAC
Anthracene;
Tricyclo[8.4.0.03,8]tetradeca-1,3,5,7,9,11,13-heptaene
Penanda
Model 3D (JSmol)
3DMet {{{3DMet}}}
ChEBI
ChEMBL
ChemSpider
DrugBank
Nomor EC
KEGG
Nomor RTECS {{{value}}}
UNII
  • InChI=1S/C14H10/c1-2-6-12-10-14-8-4-3-7-13(14)9-11(12)5-1/h1-10H YaY
    Key: MWPLVEDNUUSJAV-UHFFFAOYSA-N YaY
  • InChI=1/C14H10/c1-2-6-12-10-14-8-4-3-7-13(14)9-11(12)5-1/h1-10H
    Key: MWPLVEDNUUSJAV-UHFFFAOYAK
  • c3ccc2cc1ccccc1cc2c3
  • c1ccc2cc3ccccc3cc2c1
Sifat
C14H10
Massa molar 178,23 g·mol−1
Penampilan Tak berwarna
Bau Aromatik lemah
Densitas 1.28 g/cm3 (25 °C)[1]
0.969 g/cm3 (220 °C)
Titik lebur 21.576 °C (38.869 °F; 21.849 K)
at 760 mmHg[1]
Titik didih 3.399 °C (6.150 °F; 3.672 K)
at 760 mmHg[1]
0.022 mg/L (0 °C)
0.044 mg/L (25 °C)
0.287 mg/L (50 °C)
0.00045% w/w (100 °C, 3.9 MPa)[1]
Kelarutan Larut dalam alkohol, (C2H5)2O, aseton, C6H6, CHCl3,[1] CS2[2]
Kelarutan dalam etanol 0.076 g/100 g (16 °C)
1.9 g/100 g (19.5 °C)
0.328 g/100 g (25 °C)[2]
Kelarutan dalam metanol 1.8 g/100 g (19.5 °C)[2]
Kelarutan dalam heksana 0.37 g/100 g[2]
Kelarutan dalam toluena 0.92 g/100 g (16.5 °C)
12.94 g/100 g (100 °C)[2]
Kelarutan dalam karbon tetraklorida 0.732 g/100 g[2]
log P 4.56[1]
Tekanan uap 0.01 kPa (125.9 °C)
0.1 kPa (151.5 °C)[1]
13.4 kPa (250 °C)[3]
kH 0.039 L·atm/mol[1]
λmaks 345.6 nm, 363.2 nm[3]
Konduktivitas termal 0.1416 W/m·K (240 °C)
0.1334 W/m·K (270 °C)
0.1259 W/m·K (300 °C)[4]
Viskositas 0.602 cP (240 °C)
0.498 cP (270 °C)
0.429 cP (300 °C)[4]
Struktur
Monoclinic (290 K)[5]
P21/b[5]
C52h[5]
a = 8.562 Å, b = 6.038 Å, c = 11.184 Å[5]
α = 90°, β = 124.7°, γ = 90°
Termokimia
Kapasitas kalor (C) 210.5 J/mol·K[1][3]
Entropi molar standar (So) 207.5 J/mol·K[1][3]
Entalpi pembentukan standarfHo) 129.2 kJ/mol[1][3]
Entalpi
pembakaran
standar
ΔcHo298
7061 kJ/mol[3]
Bahaya
Piktogram GHS GHS07: Tanda SeruGHS09: Bahaya Lingkungan[6]
Keterangan bahaya GHS {{{value}}}
H315, H319, H335, H410[6]
P261, P273, P305+351+338, P501[6]
Titik nyala 121 °C (250 °F; 394 K)[6]
540 °C (1.004 °F; 813 K)[6]
Dosis atau konsentrasi letal (LD, LC):
4900 mg/kg (rats, oral)
Kecuali dinyatakan lain, data di atas berlaku pada suhu dan tekanan standar (25 °C [77 °F], 100 kPa).
YaY verifikasi (apa ini YaYN ?)
Referensi

Antrasena adalah hidrokarbon aromatis polisiklis (polycyclic aromatic hydrocarbon/PAH) dengan rumus molekul C14H10 dan terdiri atas tiga inti benzena. Senyawa ini merupakan komponen dari tar batu bara. Antrasena digunakan pada produksi bahan pewarna merah alizarin dan bahan pewarna lainnya. Antrasena tidak berwarna, tetapi memancarkan fluoresensi biru (puncak 400-500 nm) di bawah sinar ultraviolet.[8]

Keberadaan dan produksi

Tar batu bara, yang mengandung sekitar 1,5% antrasena, merupakan sumber utama material ini. Ketakmurnian yang umum adalah fenantrena dan carbazole. Antrasena dapat dipreparasi melalui metode laboratorium klasik, yaitu dengan melakukan siklodehidrasi diarilketon yang tersubstitusi o-metil atau o-metilen. Reaksi ini dikenal dengan reaksi Elbs.

Antrasena terdapat juga pada medium antarbintang.[9] Lebih dari 20% karbon di alam semesta ini dapat diasosiasikan dengan PAH, termasuk antrasena.[10]

Reaksi

Antracena mengalami dimerisasi fotokimia di bawah pengaru sinar UV:

Anthracene dimer

Senyawa dimernya, disebut diantracena (atau terkadang disebut parantracena), dihubungkan melalui pasangan ikatan karbon-karbon baru, menghasilkan [4+4] sikloadisi. Ini dapat dikembalikan menjadi antrasena secara termal atau dengan radiasi UV bawah 300 nm. Derivat antracena tersubstitusi memiliki sifat yang serupa. Reaksi dipengaruhi dengan adanya oksigen.[11][12]

Reduksi antracena dengan logam alkali menghasilkan radikal garam anion berwarna gelap M+[antracena]- (M = Li, Na, K). Hidrogenasi menghasilkan 9,10-dihidroantracena, dengan tetap mempertahankan aromatisitas cincin pengapitnya.

Oksidasi kimia berlangsung cepat, menghasilkan antraquinon, C14H8O2 (lihat di bawah), sebagai contoh, menggunakan hidrogen peroksida dan vanadil asetilasetonat.[13]

Anthraquione
Anthraquione

Antracena juga bereaksi dengan dienofile oksigen singlet pada reaksi [4+2]-sikloadisi (Reaksi Diels-Alder):

Diels alder reaction of anthracene with singlet oxygen
Diels alder reaction of anthracene with singlet oxygen

Penggunaan

Antracena dikonversi terutama menjadi antraquinon, suatu prekursor zat pewarna.[14]

Ceruk

Antracena, suatu semikonduktor organik dengan kesenjangan pita yang lebar digunakan sebagai scintillator pada detektor foton, elektron dan partikel alfa berenergi tinggi. Plastik seperti polivinil toluena, dapat diisi dengan antracena untuk memproduksi scintillator plastik yang digunakan untuk dosimetri radioterapi. Puncak spektrum emisi antracena berkisar antara 400 nm dan 440 nm.

Antracena juga digunakan untuk bahan pengawet kayu, insektisida, dan bahan pembungkus.

Antracena adalah salah satu dari tiga komponen (dua lainnya adalah kalium perklorat dan belerang) yang digunakan untuk memproduksi asap hitam selama Papal Conclave.[15]

Derivat antracena

Berbagai macam derivat antracena digunakan untuk berbagai keperluan. Derivat dengan gugus hidroksil adalah 1-hidroksiantracena dan 2-hidroksiantracena (homolog fenol dan naftol). Hidroksiantracena (disebut juga antrol dan antracenol)[16][17] merupakan zat yang aktif secara farmakologi. Dijumpai juga antracena dengan kandungan gugus hidroksil lebih dari satu, seperti pada 9,10-dihidroantracena.

Toksikologi

.[18] Anthracene, as many other PAHs, is generated during combustion processes: Exposure to humans happens mainly through tobacco smoke and ingestion of food contaminated with combustion products.[19]

Referensi

  1. ^ a b c d e f g h i j k Lide, David R., ed. (2009). CRC Handbook of Chemistry and Physics (edisi ke-90). Boca Raton, Florida: CRC Press. ISBN 978-1-4200-9084-0. 
  2. ^ a b c d e f Seidell, Atherton; Linke, William F. (1919). Solubilities of Inorganic and Organic Compounds (edisi ke-2nd). New York: D. Van Nostrand Company. hlm. 81. 
  3. ^ a b c d e f Anthracene dalam Linstrom, P.J.; Mallard, W.G. (eds.) NIST Chemistry WebBook, NIST Standard Reference Database Number 69. National Institute of Standards and Technology, Gaithersburg MD. http://webbook.nist.gov (diakses tanggal 2014-06-22)
  4. ^ a b "Properties of Anthracene". http://www.infotherm.com. Wiley Information Services GmbH. Diarsipkan dari versi asli tanggal 2014-11-01. Diakses tanggal 2014-06-22.  Hapus pranala luar di parameter |website= (bantuan)
  5. ^ a b c d Douglas, Bodie E.; Ho, Shih-Ming (2007). Structure and Chemistry of Crystalline Solids. New York: Springer Science+Business Media, Inc. hlm. 289. ISBN 0-387-26147-8. 
  6. ^ a b c d e Sigma-Aldrich Co., Anthracene. Diakses tanggal 2014-06-22.
  7. ^ "MSDS of Anthracene". http://www.fishersci.ca. Fisher Scientific. Diakses tanggal 2014-06-22.  Hapus pranala luar di parameter |website= (bantuan)
  8. ^ Jonathan Lindsey and coworkers.
  9. ^ Iglesias-Groth, S.; Manchado, A.; Rebolo, R.; Gonzalez Hernandez, J. I.; Garcia-Hernandez, D. A.; Lambert, D. L. (May 2010).
  10. ^ Hoover, Rachel (February 21, 2014).
  11. ^ Rickborn, Bruce "The retro-Diels-Alder reaction.
  12. ^ Bouas-Laurent, Henri; Desvergne, Jean-Pierre; Castellan, Alain; Lapouyade, Rene "Photodimerization of anthracenes in fluid solution: structural aspects" Chemical Society Reviews (2000), vol. 29, pp. 43-55. doi:10.1039/a801821i[1]
  13. ^ Kimberly D. M. Charleton, Ernest M. Prokopchuk Coordination Complexes as Catalysts: The Oxidation of Anthracene by Hydrogen Peroxide in the Presence of VO(acac)2 Journal of Chemical Education 2011 88 (8), 1155-1157 doi:10.1021/ed100843a[2]
  14. ^ Gerd Collin, Hartmut Höke and Jörg Talbiersky "Anthracene" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2006. doi:10.1002/14356007.a02_343.pub2[3]
  15. ^ Vatican Radio, Briefing by Fr. Federico Lombardi, 03/13/2013, 1 p.m.
  16. ^ 1-Hydroxyanthracene NIST datapage
  17. ^ 2-Hydroxyanthracene NIST datapage
  18. ^ MSDS
  19. ^ http://www.cie.iarc.fr/htdocs/monographs/vol32/anthracene.html[pranala nonaktif permanen]

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