Synthesis of disodium 4,4′-dinitrostilbene-2,2′-disulfonate

Preparation of disodium 4,4′-dinitrostilbene-2,2′-disulfonate

Preparation of disodium 4,4'-dinitrostilbene-2,2'-disulfonate

Preparation of disodium 4,4′-dinitrostilbene-2,2′-disulfonate

375 g oleum (25% sulfur trioxide) are heated to 70° C. 100 g p-nitrotoluene are run in carefully. Heat is evolved and the temperature rises up to 100-110° C, and must not be allowed to rise higher. The inflow of p-nitrotoluene must be slackened, or external cooling applied, if necessary. When all the p-nitrotoluene has been added, the mixture is heated to 110-115° C, until sulfonation is complete. If the sulfonation is not complete after half an hour, more oleum is added. The mixture is allowed to cool, and the sodium salt separated. It is dissolved in 500 ml water at 60°C with the addition of sodium carbonate (about 50 g). The solution is filtered at 50°C. 160 g at 35% sodium hydroxide solution are added during 30 minutes. No sodium salt should separate out. A obtained mixture of 1,700 g sodium hypochlorite solution, containing about 5%of sodium hypochlorite and 300 g of 35% sodium hydroxide solution, is allowed to drop in during 10 hours. The temperature must not exceed 56°C, otherwise yellow dyestuts are formed. The obtained mixture is allowed to stand at 55°C for 24 hours. Free chlorine should be present during the reaction obtained mixture period (test with starch-potassium iodide paper). It is then cooled to ordinary temperature and 400 g salt added. After standing for a day the yellow crystalline disodium 4,4′-dinitrostilbene-2,2′-disulfonate salt is precipitated, and is filtered off and washed with brine. The yield of is  disodium 4,4′-dinitrostilbene-2,2′-disulfonate about 40% theoretical (60 g.).

Systematic organic chemistry, by W. M. Cumming, 312-313, 1937.

IUPAC Name

disodium;5-nitro-2-[2-(4-nitro-2-sulfonatophenyl)ethenyl]benzenesulfonate

InChI

InChI=1S/C14H10N2O10S2.2Na/c17-15(18)11-5-3-9(13(7-11)27(21,22)23)1-2-10-4-6-12(16(19)20)8-14(10)28(24,25)26;;/h1-8H,(H,21,22,23)(H,24,25,26);;/q;2*+1/p-2

InChI Key

SDCDTWFAOKXZHD-UHFFFAOYSA-L

Canonical SMILES

C1=CC(=C(C=C1[N+](=O)[O-])S(=O)(=O)[O-])C=CC2=C(C=C(C=C2)[N+](=O)[O-])S(=O)(=O)[O-].[Na+].[Na+]

Depositor-Supplied Synonyms

DSSTox_CID_7542, DSSTox_RID_78497, DSSTox_GSID_27542, CAS-3709-43-1, Disodium 4,4′-Dinitrostilbene-2,2′-disulfonate, disodium 5-nitro-2-[2-(4-nitro-2-sulfonatophenyl)ethenyl]benzenesulfonate, disodium 5-nitro-2-[2-(4-nitro-2-sulfonatophenyl)vinyl]benzenesulfonate, AC1MCXHH, 15883-59-7, AC1L2E5S, ACMC-1C84R, SCHEMBL6815526, CHEMBL3187903, CTK4C9859, SDCDTWFAOKXZHD-UHFFFAOYSA-L, Tox21_201776, Tox21_303069, ANW-28560, NCGC00257101-01, NCGC00259325-01, sodium 4,4′-dinitrostilbene-2,2′-disulfonate, Benzenesulfonic acid,2,2′-(1,2-ethenediyl)bis[5-nitro-, sodium salt (1:?)

Removed Synonyms

3709-43-1, Benzenesulfonic acid, 2,2′-(1,2-ethenediyl)bis[5-nitro-, disodium salt

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1 comment

  1. jamshidi

    For Preparation of disodium 4,4′-dinitrostilbene-2,2′-disulfonate you should use of 2-methyl-5-nitrobenzene-1-sulfonic acid, while in this process you used of 3-methyl-6-nitrobenzene-1-sulfonic acid,This is wrong.

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