Quinizarin → Anthraquinone

HRID 1867209Notes

Reaction equation

HRID 1867209 reaction equation
NCCCOCCOCCO.[CH2:12]1[C:26](=O)[C:25]2[C:16](=[C:17]([OH:29])[C:18]3[C:23]([C:24]=2[OH:28])=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:14](=O)[CH2:13]1.C1C=CC2C(=O)C3C(=C(O)C=CC=3O)C(=O)C=2C=1>O>[CH:19]1[C:18]2[C:17](=[O:29])[C:16]3[C:25](=[CH:26][CH:12]=[CH:13][CH:14]=3)[C:24](=[O:28])[C:23]=2[CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 6688QuinizarinHCID 66985Ethanol, 2-[2-(3-aminopropoxy)ethoxy]-HCID 872111,4-Anthracenedione, 2,3-dihydro-9,10-dihydroxy-

Product 1

HCID 6780Anthraquinone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

To a 1 L glass reaction vessel equipped with a mechanical stirrer, temperature probe, water-cooled condenser, and a gas inlet tube was added 2-[2-(3-aminopropoxy)ethoxy]ethanol (291 g), leucoquinizarin (52 g), and quinizarin (152 g). The reaction mixture was heated under a nitrogen atmosphere to 70° C., at which time agitation was started. The reaction mixture was then heated to 80° C. After heating at that temperature for 4 hours, a gentle stream of air was introduced into the reaction mixture and heating at 80° C. was continued with the air sparge in order to oxidize the reaction mixture. After heating an additional 5 hours, the oxidation was complete. The reaction mixture was then cooled to room temperature to produce a blue anthraquinone colorant having a maximum absorbance at 639 nanometers and a color value of 31.5 (absorbance/g/L in methanol). The colorant contained 0.2% 1-(3-(2-(2-hydroxyethoxy)ethoxy)propylamino-4-hydroxyanthraquinone (i.e. violet impurity) and 0.7% of water and methanol insoluble black impurity. The structure of the anthraquinone colorant is shown below:

Workup

  1. customequipped with a mechanical stirrer
  2. temperatureThe reaction mixture was then heated to 80° C
  3. temperatureAfter heating at that temperature for 4 hours
  4. additiona gentle stream of air was introduced into the reaction mixture
  5. temperatureheating at 80° C.
  6. customsparge in order
  7. temperatureAfter heating an additional 5 hours
  8. temperatureThe reaction mixture was then cooled to room temperature

Sources & evidence

ORD record
ord-ba5ff3ccc0f44be8817f452c21203e36
Source dataset
uspto-grants-2009_12
Patent number
US07632682B2

Reaction notes

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