Sodium 2-anthraquinonesulfonate

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Sodium 2-anthraquinonesulfonate
Sodium 2-anthraquinonesulfonate.png
Names
Preferred IUPAC name
Sodium 9,10-dioxo-9,10-dihydroanthracene-2-sulfonate
Other names
Sodium 2-anthrachinonesulphonate; 2-Anthraquinone sodium sulfonate; Silver salt
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.004.555 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C14H8O5S.Na/c15-13-9-3-1-2-4-10(9)14(16)12-7-8(20(17,18)19)5-6-11(12)13;/h1-7H,(H,17,18,19);/q;+1/p-1 X mark.svgN
    Key: GGCZERPQGJTIQP-UHFFFAOYSA-M X mark.svgN
  • O=C1C2=C(C=CC(S(=O)([O-])=O)=C2)C(C3=CC=CC=C31)=O.[Na+]
Properties
C14H7NaO5S
Molar mass 310.25 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Sodium 2-anthraquinonesulfonate (AMS) is a water-soluble anthraquinone derivative. In the laboratory it can be prepared by sulfonation of anthraquinone. [1]

Digester additive in papermaking

AMS is used as a catalyst in production of alkaline pulping in the soda process. It goes through a redox cycle similar to that of anthraquinone to give a catalytic effect. AMS was discovered as an efficient pulping catalyst before anthraquinone, [2] but has a higher cost.

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14
H
8
O
2
. Isomers include various quinone derivatives. The term anthraquinone however refers to the isomer, 9,10-anthraquinone wherein the keto groups are located on the central ring. It is a building block of many dyes and is used in bleaching pulp for papermaking. It is a yellow, highly crystalline solid, poorly soluble in water but soluble in hot organic solvents. It is almost completely insoluble in ethanol near room temperature but 2.25 g will dissolve in 100 g of boiling ethanol. It is found in nature as the rare mineral hoelite.

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The anthraquinone process is a process for the production of hydrogen peroxide, which was developed by BASF. The industrial production of hydrogen peroxide is based on the reduction of oxygen, as in the direct synthesis from the elements. Instead of hydrogen itself, however, a 2-alkyl-anthrahydroquinone, which is generated before from the corresponding 2-alkyl-anthraquinone by catalytic hydrogenation with palladium is used. Oxygen and the organic phase react under formation of the anthraquinone and hydrogen peroxide. Among other alkyl groups (R) ethyl- and tert-butyl- are used, e.g., 2-ethylanthraquinone.

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References

  1. Cumming, W. M. (1937). Systematic organic chemistry. p. 325. Retrieved 2016-01-11 via PrepChem.com.
  2. "Anthraquinone/ alkali pulping. A literature review" (PDF). July 1978.