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Home > Encyclopedia > 1,5-Diaminochloro-4,8-dihydroxy-9,10-anthracenedione

1,5-Diaminochloro-4,8-dihydroxy-9,10-anthracenedione

1,5-Diaminochloro-4,8-dihydroxy-9,10-anthracenedione structure

1,5-Diaminochloro-4,8-dihydroxy-9,10-anthracenedione 

structure
  • CAS No:

    12217-79-7

  • Formula:

    C14H9ClN2O4

  • Chemical Name:

    1,5-Diaminochloro-4,8-dihydroxy-9,10-anthracenedione

  • Synonyms:

    9,10-Anthracenedione,1,5-diaminochloro-4,8-dihydroxy-;1,5-Diaminochloro-4,8-dihydroxy-9,10-anthracenedione;1,5-Dihydroxy-4,8-diaminochloroanthraquinone;Disperse blue 56;34344-90-6;50814-71-6;71807-39-1;71807-42-6;84933-12-0

  • Categories:

    Dyes and Pigments  >  Dye

1,5-Diaminochloro-4,8-dihydroxy-9,10-anthracenedione Basic Attributes

349.14

304.02500

235-401-1

DTXSID0065270

3204110000

Characteristics

126.64000

2.85340

darkblue powder

1.4410 (rough estimate)

129°C (rough estimate)

1.6800 (estimate)

1.18E-18mmHg at 25°C

1,5-Diaminochloro-4,8-dihydroxy-9,10-anthracenedione Use and Manufacturing

Methods of Manufacturing

The preparation method of Disperse Blue 2BLN is divided into mercury method and non-mercury method. Because the mercury method requires mercury sulfate as a sulfonation locator, it brings mercury-containing wastewater and causes environmental pollution, so it is gradually stopped. Non-mercury method is divided into phenoxy method and methoxy method. The synthesis method is as follows:. The first nitrification: add 100% sulfuric acid and anthraquinone to the nitrification pot and stir well; slowly add the mixed acid (prepared from the same amount of 100% sulfuric acid and 100% nitric acid) within 4-5h, and the temperature rises to about 80℃, and keep it 4-5h, cool and filter, wash with 100% sulfuric acid, then wash with water until neutral, and dry to obtain crude product. Add the crude product to the separation pot and add 100% sulfuric acid to dissolve it. After it is heated to 120℃ within 1 hour, it is completely dissolved, then slowly cooled to precipitate out 1, 5-dinitroanthraquinone, filtered, washed with 100% sulfuric acid, and then washed with water to medium Properties, dry to get 1, 5-dinitroanthraquinone, melting point 372-375℃. If it is recrystallized with nitrobenzene, the melting point can rise to 384-385°C (the pure product melting point is 422°C). The filtrate is slowly added to ice water until the sulfuric acid concentration reaches about 70%, and 1, 8-dinitroanthraquinone is precipitated. It is filtered, washed with 70% sulfuric acid, washed with water until neutral, and dried to obtain 1, 8-dinitroanthracene. Quinone. The melting point is 280-290°C. Phenoxylation: add sodium hydroxide and phenol into the reaction pot, heat it to 130-140℃ to melt all of it, then cool to 120℃, add 1, 5-dinitroanthraquinone, and heat up to within 2-4h Incubate at 140-145°C for 2h, heat up to 145-155°C for 6h, after measuring the end point, distill phenol under reduced pressure (140°C/21.3kPa), finish steaming, dilute with heating water, add 30% sodium hydroxide solution and stir for 4h , Filter, wash with water to neutral, get 1, 5-diphenoxyanthraquinone. Second nitration: Add a small amount of water to the nitrification pot, then add 98% sulfuric acid and 1, 5-diphenoxyanthraquinone, stir and maintain at 10°C to dissolve all of it, then slowly add 96% nitric acid within 2 hours. After the addition, the temperature was raised to 40°C and kept for 8h. Then pour the nitrated material into a large amount of ice water, filter under 40°C, and wash with water until it is neutral to obtain 1, 5-(2, 4-dinitrophenoxy)-4, 8-dinitroanthraquinone. Hydrolysis: Add clean water and nitrate filter cake to the hydrolysis pot and stir evenly, then add 30% sodium hydroxide, heat to 95℃, keep for 30min, cool to below 50℃, filter, wash with 3% sodium hydroxide, wash until washing The solution has no precipitation after acid precipitation and is filtered to obtain 1, 5-dinitro-4, 8-dihydroxyanthraquinone. The filtrate is acidified and filtered to obtain 2, 4-dinitrophenol. Reduction: Add clean water, 1, 5-dinitro-4, 8-dihydroxyanthraquinone filter cake to the reduction pot, stir well, then add 15% sodium sulfide solution, heat up to 90℃, keep it warm for 1h, and cool to 40 Filter at -45°C, wash with water to neutral, then wash with 0.5% hydrochloric acid, then wash with water to neutral, and dry to obtain 1, 5-diamino-4, 8-dihydroxyanthraquinone. Bromination: Add 3%-5% fuming sulfuric acid, a small amount of boric acid and reducing material filter cake into the bromination pot, stir evenly (about 2h), add bromine, slowly increase the temperature (within about 5h) to 80°C, keep it for 4h, Cool to below 40°C, pour the brominated material into a large amount of ice water, filter at about 40°C, wash with water to neutrality, and obtain a filter cake of Disperse Blue 2BLN. Post-treatment: add filter cake and diffusing agent to the grinding pot, neutralize with sodium hydroxide to pH=7-7.5, grind at 90°C for 14h, dry and pulverize to obtain the finished product.

Uses

Mainly used for dyeing polyester and its blended fabrics

9,10-Anthracenedione, 1,5-diaminochloro-4,8-dihydroxy-: ACTIVE

Computed Properties

Molecular Weight:304.68
XLogP3:2.5
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:6
Exact Mass:304.0250845
Monoisotopic Mass:304.0250845
Topological Polar Surface Area:127
Heavy Atom Count:21
Complexity:474
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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