2-Amino-5-hydroxynaphthalene-1,7-disulphonic acid → Sulfanilic acid

HRID 1742558

반응식

HRID 1742558 반응식
[N+:1]([C:4]1[CH:5]=[C:6](N)[C:7](=[CH:12][CH:13]=1)[S:8]([OH:11])(=[O:10])=[O:9])([O-])=O.OC1C2C(=C(S(O)(=O)=O)C(N)=CC=2)C=C(S(O)(=O)=O)C=1>O>[S:8]([OH:11])(=[O:10])([C:7]1[CH:6]=[CH:5][C:4]([NH2:1])=[CH:13][CH:12]=1)=[O:9]

참가 물질

4

반응물 2

HCID 810242-Amino-5-hydroxynaphthalene-1,7-disulphonic acidHCID 904642-Amino-4-nitrobenzenesulfonic acid

생성물 1

HCID 8479Sulfanilic acid

시약·촉매·용매 1

HCID 962Water용매2회

실험 절차

4-Nitro-o-sulfanilic acid is diazotized and coupled neutrally to I acid. 43 mmol of this dye are dissolved in 200 ml water and indirectly diazotized. After stirring for 1 hour, the excess nitrous acid is removed with amidosulfonic acid and a solution of 43 mmol 4-hydroxy- 7-aminonaphthalene-2,8-disulfonic acid in 200 ml water is added. Coupling is completed overnight at pH 8-9, the dye is filtered under suction and the sulfo groups are split off by boiling for 12 h in a 1:1 mixture of water and N-methyl pyrrolidone containing 60 ml concentrated hydrochloric acid. This dye is diazotized and added dropwise to a solution in 100 ml water of 7.2 mmol of a dye obtained by acidic coupling of p-sulfanilic acid onto 4-amino-5-hydroxynaphthalene sulfonic acid. After stirring overnight, the dye is precipitated by addition of acetone, optionally dissolved and allowed to crystallize once more and then washed with aqueous acetone. 0.1 g dye are dissolved in 9.9 g Mowiol® 28-99 (a product of Hoechst AG) and 190 ml water and a 500μ thick layer is cast from this solution. After evaporation of the water, an approx. 50μ thick dark-blue film is obtained. The film is stretched by 500% at 130° C. The dichroic ratio (CR) is 15.3 at 650 nm.

후처리

  1. customthe excess nitrous acid is removed with amidosulfonic acid
  2. waitCoupling is completed overnight at pH 8-9
  3. filtrationthe dye is filtered under suction
  4. customthe sulfo groups are split off
  5. additionby boiling for 12 h in a 1:1 mixture of water and N-methyl pyrrolidone containing 60 ml concentrated hydrochloric acid
  6. additionadded dropwise to a solution in 100 ml water of 7.2 mmol of a dye

출처 및 근거

ORD 기록
ord-80405a6d202c492785d5d8c257f95b45
출처 데이터셋
uspto-grants-1994_08
특허 번호
US05340504

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