Ácido 2-hidroxi-3-oxobutanoico

Ácido 2-hidroxi-3-oxobutanoico Alerta sobre risco à saúde

Nome IUPAC	2-hydroxy-3-oxobutanoic acid
Outros nomes	ácido acetilglicólico ácido alfa-hidroxiacetoacético ácido 2-hidroxiacetoacético
Identificadores
Número CAS	37520-05-1
SMILES	`CC(=O)C(O)C(O)=O`
Propriedades
Fórmula molecular	C₄H₆O₄
Massa molar	118,087997
Ponto de fusão	66-68 °C
Ponto de ebulição	303,487 °C
Página de dados suplementares
Estrutura e propriedades	n, ε_r, 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.

Ácido 2-hidroxi-3-oxobutanoico, ácido acetilglicólico, ácido alfa-hidroxiacetoacético ou ácido 2-hidroxiacetoacético é o composto orgânico de fórmula C₄H₆O₄, SMILES CC(=O)C(O)C(O)=O e massa molecular 118,087997. Apresenta-se como um mistura racêmica que é classificada com o número CAS 37520-05-1. É classificado ainda com o EINECS 237-541-9 e ChemSpider ID 14491053. Apresenta ponto de fusão 66-68 °C^[1], ponto de ebulição 303,487 °C a 760 mmHg, ponto de fulgor 151,57 °C e entalpia de vaporização 63,069 kJ/mol.^[2]^[3]

Apresenta-se em duas formas enantioméricas, o ácido (2R)-2-hidroxi-3-oxobutanoico, classificado com o número CAS 335265-55-9, e o ácido (2S)-2-hidroxi-3-oxobutanoico, classificado com o número CAS 335265-54-8.^[4]^[5]

Sofre hidrólise alcalina.^[6]

Obtenção

É produzido nas reações para a produção de ácido glicólico a partir do paraformaldeído ou trioxano, se o ácido acético está presente na mistura de reação:^[7]

HO-CH₂-COOH + CH₃COOH → CH₃COOCH₂COOH + H₂O

É produzido na carbonilação de formaldeído a glicolato de metila sob ação de resinas de troca iônica catiônicas quando usando-se ácido acético como solvente.^[8]

Resulta da hidrólise em refluxo em banho de vapor à pressão reduzida do ácido glicólico com cloreto de acetila.^[1]

Pode ser obtido a partir de cetena obtida a partir de anidrido acético e ácido acético glacial em presença de acetona anidra.^[9]

Ver também

Ácido 3-hidroxi-2-oxobutanoico, SMILES CC(O)C(=O)C(O)=O, classificado com o número CAS 1944-42-9.^[10]

Referências

↑ ^a ^b Sten Gatenbeck; A synthesis of 1,3-Dihydroxyacetone Convenient for ¹⁴C-labelling; Acta Chem. Scand. 9 (1955) No. 4.
↑ 2-Hydroxy-3-oxobutanoic acid - www.chemspider.com
↑ 2-hydroxy-3-oxobutanoic acid^{[ligação inativa]} - www.molport.com
↑ (2R)-2-hydroxy-3-oxobutanoic acid^{[ligação inativa]} - www.molport.com
↑ (2S)-2-hydroxy-3-oxobutanoic acid^{[ligação inativa]} - www.molport.com
↑ Gower, Albert Hugh; The chemical kinetics of the alkaline hydrolysis of Acetyl-glycolic acid; Thesis (M.S.) - Massachusetts State College, 1933.
↑ From paraformaldehyde or trioxane and formic acid or formate, acid catalyst - US 4128575 A - Google Patents
↑ Sakae Uemura, Takeaki Mitsudo, Masatate Haruta; Frontiers and Tasks of Catalysis Towards the Next Century: Proceedings of the International Symposium in Honour of Professor Tomoyuki Inui; VSP, 1998.
↑ Process for the production of acylated hydroxy-substituted carboxylic acids - US 2423569 A - Google Patents
↑ 3-hydroxy-2-oxobutanoic acid^{[ligação inativa]} - www.molport.com

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