Aromatic sulfinic acid compound preparation method

Abstract

The invention discloses an aromatic sulfinic acid compound preparation method, comprising using chlorine aluminic acid ion liquid as a catalyst, obtaining aromatic sulfinic acid by an Friedel-Crafts acylation reaction of an aromatic compound and sulfur dioxide. Among the aromatic compounds, benzene series compounds and naphthalene series compounds are preferred. The method of the invention is mild in reaction condition and short in reaction time. The yield of benzene series products is more than 80% and the yield of naphthalene series products is more than 70% and the product content is more than 92%.

Description

technical field [0001] The invention belongs to the field of organic synthesis and relates to a preparation method of aromatic sulfinic acid compounds. Background technique [0002] Aromatic sulfinic acids, especially benzene-based and naphthalene-based sulfinic acids, are an important class of intermediates, which are generally solid at room temperature. Such compounds are widely used in the fields of dyes, medicines, pesticides, photosensitizers, and electroplating additives. There have been reports in the literature on its synthesis. In the early 20th century, the literature [Ber.41, 3315-22 (1908)] reported that benzene and SO 2 in AlCl 3 The gas-liquid two-phase method synthesizes benzenesulfinic acid under the action, and the yield is 80%, but because the reaction temperature is low (0-5 ℃), the reaction time is too long, the AlCl in the reaction 3 The consumption is large, and a large amount of acid waste water is produced after the reaction, and there are no follo...

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Problems solved by technology

There have been reports in the literature on its synthesis. In the early 20th century, the literature [Ber.41, 3315-22 (1908)] reported that benzene and SO 2 in AlCl 3 The gas-liquid two-phase method synthesizes benzenesulfinic acid under the action, and the yield is 80%, but because the reaction temperature is low (0-5 ℃), the reaction time is too long, the AlCl in the reaction 3 The consumption is large, and a large amount of acid waste water is produced after the reaction, and there are no follow-up reports; the literature [J.Chem.SOC.1 948,528] reported that aromatic magnesium halide or aromatic lithium and SO 2 The method for preparing sulfinic acid by reaction requires the use of organometallic compound Grignard reagents and organic lithium as raw materials, resulting in harsh reaction conditions and high costs; patent DE95830 reports that aromatic diazonium salts react with SO under the action of copper or copper salts. 2 Carry out Sandmeyer reaction to prepare aromatic sulfinic acid; at present, aromatic sulfinic acid is produced by the chlorosulfonation reaction of aromatic compounds through chlorosulfonic acid, and the obtained sulfonyl chloride is reduced and acidified under the action of reducing agent sulfite or zinc powder. , although the total yield of benzene series can reach 80-85%, and the total yield of naphthalene series can reach 50%-60%, but the two-step reaction of this method produces a large amount of sulfuric acid and hydrochloric acid and sodium sulfate, sodium chloride or oxidation Zinc waste water, waste residue

In summary, there is a lack of an environmentally friendly, efficient preparation method for aromatic sulfinic acid compounds in the prior art

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