Preparation of 2,6- and 2,7-disubstituted anthraquinone derivatives

Patent metadata

Field	Value
Publication number	US-9988268-B2
Application number	US-201515314560-A
Country	US
Kind code	B2
Filing date	May 28, 2015
Priority date	May 30, 2014
Publication date	Jun 5, 2018
Grant date	Jun 5, 2018

Abstract

The present invention relates to novel anthraquinone derivatives, 2,6-diisohexylanthracene-9,10-dione and 2,7-diisohexyl-anthracene-9,10-dione, preferably to be used for the preparation of hydrogen peroxide, and to a process for the preparation of these anthraquinone derivatives.

First claim

The invention claimed is:

1. A compound of formula (Ia)

2. A compound of formula (Ib)

3. A composition, comprising a compound of formula (Ia)

and a compound of formula (Ib)

4. The composition of claim 3 , wherein at least 90 weight-% of the composition consists of the compounds of formula (Ia) and formula (Ib).

5. The composition of claim 3 , wherein the molar ratio of the compound of formula (Ia) relative to the compound of formula (Ib) is in a range of from 0.2:1 to 5:1.

6. The composition of claim 3 , having a solubility of at least 1.0 mol/l in a solvent mixture of which at least 99.9 weight-% consists of ortho-xylene and diisobutyl carbinol wherein the molar ratio of the ortho-xylene relative to the diisobutyl carbinol in a range of from 0.99:1 to 1.01:1, wherein said solubility refers to the molar amount of the compound of formula (Ia) plus the molar amount of the compound of formula (Ib) dissolved in 1 l of the solvent mixture at a temperature of from 20 to 23° C. and at a pressure of from 0.9 to 1.1 bar.

7. The composition of claim 3 , wherein at least 90 weight-% of the compound of formula (Ia) and at least 96 weight-% of the compound of formula (Ib) are present in solid form.

8. The composition of claim 3 , being at least partially dissolved in a solvent.

9. A solution, comprising a compound of formula (Ia)

and/or a compound of formula (Ib)

and a solvent.

10. A process for preparing a composition comprising a compound of formula (Ia)

and a compound of formula (Ib)

said process comprising:
(i) providing a mixture comprising the compound of formula (IIa)

and the compound of formula (IIb)

and
(ii) subjecting the mixture to a hydrogenation reaction.

11. The process of claim 10 , wherein (i) comprises
(a) providing a compound of formula (III)

(b) reacting the compound of formula (III) with a compound of formula (IV)

thereby obtaining a mixture comprising a compound of formula (Va)

and a compound of formula (Vb)

and
(c) subjecting the mixture obtained in (b) to an oxidation reaction thereby obtaining a mixture comprising the compound of formula (IIa) and the compound of formula (IIb).

12. The process of claim 11 , wherein the reacting (b) is carried out in a solvent.

13. The process of claim 11 , further comprising: after (b) and prior to (c),
(b′) separating the compounds of formula (Va) and formula (Vb) from the mixture obtained in (b), thereby obtaining a mixture comprising the compounds of formula (Va) and formula (Vb).

14. The process of claim 11 , wherein prior to (c), the compounds of formula (Va) and formula (Vb) are not separated from the mixture obtained in (b).

15. The process of claim 11 , wherein the oxidation reaction in (c) is carried out in a solvent.

16. The process of claim 11 , further comprising: after (c) and prior to (ii),
(c′) separating the compounds of formula (IIa) and formula (IIb) from the mixture obtained in (c), thereby obtaining a mixture comprising the compounds of formula (IIa) and formula (IIb).

17. The process of claim 11 , wherein after (c) and prior to (ii), the compounds of formula (IIa) and formula (II) are not separated from the mixture obtained in (c).

18. The process of claim 10 , wherein the hydrogenation reaction in (ii) is carried out in a solvent in the presence of a hydrogenation catalyst.

19. The process of claim 10 , further comprising
(iii) treating the mixture obtained in (ii) with an inorganic base, thereby obtaining a mixture comprising the compounds of formula (Ia) and formula (Ib).

20. The process of claim 10 , further comprising crystallizing the compounds of formula (Ia) and formula (Ib) from the mixture obtained in (ii).

21. A mixture or a composition, comprising the compounds of formula (Ia)

and of formula (Ib)

obtained by the process of claim 10 .

22. A process for preparing hydrogen peroxide, the process comprising:
preparing hydrogen peroxide from a compound selected from the group consisting of a compound of formula (Ia), a compound of formula (Ib), and a combination thereof:

23. A process for preparing hydrogen peroxide, the process comprising
(I) providing a compound of formula (Ia)

or a compound of formula (Ib)

or a composition comprising the compound of formula (Ia) and the compound of formula (Ib);
(II) preparing a mixture comprising the compound or the composition provided in (I) dissolved in an organic solvent, and further comprising a hydrogenation catalyst;
(III) subjecting the mixture prepared in (II) to a hydrogenation reaction, thereby obtaining a mixture comprising a compound of formula (VIIa)

or comprising a compound of formula (VIIb)

or comprising the compound of formula (VIIa) and the compound formula (VIIb);
(IV) subjecting the mixture obtained in (III) to an oxidation reaction in the presence of an oxygen containing gas, thereby obtaining a mixture comprising the compound of formula (Ia), or the compound of formula (Ib), or the compound of formula (Ia) and the compound of formula (Ib), and further comprising hydrogen peroxide; and
(V) separating hydrogen peroxide from the mixture obtained in (IV), thereby obtaining a

Assignees

• Basf Se

Inventors

• Riedel Dominic
• Teles Joaquim Henrique
• Wurm Thomas

Classifications

• C07C45/62 Primary

  by hydrogenation of carbon-to-carbon double or triple bonds · CPC title

• C01B15/023 Primary

  by the alkyl-anthraquinone process · CPC title

• C07C50/18

  Anthraquinones, i.e. C14H8O2 · CPC title

• C07C50/00 Primary

  Quinones · CPC title

• C07C46/08

  with molecular oxygen · CPC title