Alizarina

Alizarina
Alerta sobre risco à saúde
Nome IUPAC 1,2-dihydroxy-9,10-anthracenedione
Outros nomes 1,2-dihydroxyanthraquinone, vermelho-escuro, bordô, vermelho-alzarina, 9,10-anthracenedione
Identificadores
Número CAS 72-48-0
SMILES
Propriedades
Fórmula molecular C14H8O4
Massa molar 240.21 g/mol
Aparência Vermelho-alaranjado
Ponto de fusão

279 - 283 °C

Ponto de ebulição

430 °C

Solubilidade em água ? g/100 ml (?°C)
Riscos associados
MSDS External MSDS
Frases R R36 R37 R38
Frases S S26 S36
Compostos relacionados
Compostos relacionados Antraquinona
Antraceno
Antragalol (1,2,3-Trihidroxiantraquinona)
Página de dados suplementares
Estrutura e propriedades n, εr, etc.
Dados termodinâmicos Phase behaviour
Solid, liquid, gas
Dados espectrais UV, IV, RMN, EM
Exceto onde denotado, os dados referem-se a
materiais sob condições normais de temperatura e pressão

Referências e avisos gerais sobre esta caixa.
Alerta sobre risco à saúde.

A alizarina é um corante e pigmento vermelho derivado originalmente da raiz da garança da espécie Rubia tinctorum.

A palavra alizarina deriva do árabe al-usara, significando suco.[1]

Alizarina é também o nome genérico de uma variedade de corantes, tais como "Verde Alizarina Cyanina G" e "Azul Brilhante Alizarina R".

História

A alizarina foi usada como corante desde há milénios. De Tutancâmon a Carlos Magno, aos viquingues, a raiz de rubia foi utilizada em corantes até 1860.[2]

Alizarina foi reconhecida por Graebe e Liebermann, em 1868, como um derivado do antraceno, e posteriormente por estes sintetizada[3], quando trabalhavam sob Adolf von Baeyer, em um processo de três etapas, vendido posteriormente à então Badische Dye Company (depois BASF), devido ao seu custo e requerimento de bromo.[4]

Em 1869[5] (ou 1870[2]) transformou-se no primeiro pigmento natural a ser sintetizado.

Mesmo com as limitadas técnicas do século XIX, o pigmento obtido artificialmente tinha a metade do custo do natural, fazendo o mercado de cultivo da planta declinar e entrar em colapso.[2][3]

Aplicações

Quando diluído em álcool em solução 75% é chamado de alizarol, que é usado por indústrias de laticínios para verificar a estabilidade térmica do leite e fazer uma estimativa sobre a acidez do mesmo.

Obtenção

A síntese química a partir do antraceno, obtido a partir do alcatrão da hulha, pela fusão de seu derivado 2-antraquinossulfonato de sódio com bases alcalinas.

Referências

  1. alizarin. Dictionary.com Unabridged (v 1.1). Random House, Inc. (em inglês)
  2. a b c Alizarin (Not so mad for madder anymore, are we?) Arquivado em 6 de maio de 2007, no Wayback Machine. - Molecule of The Day (em inglês)
  3. a b Madder - www.botanical.com (em inglês)
  4. Philip Ball; Bright earth: art and the invention of color; University of Chicago Press, 2003; ISBN 0-226-03628-6, 9780226036281 (em inglês)
  5. Hans-Samuel Bien, Josef Stawitz, Klaus Wunderlich “Anthraquinone Dyes and Intermediates”; Ullmann’s Encyclopedia of Industrial Chemistry 2005 Wiley-VCH, Weinheim: 2005. doi:10.1002/14356007.a02

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