Crystal composition (CC) comprising 4,4#-dichlorodiphenylsulfoxide crystals (C)

Patent metadata

Field	Value
Publication number	US-10975024-B2
Application number	US-202016784287-A
Country	US
Kind code	B2
Filing date	Feb 7, 2020
Priority date	Feb 8, 2019
Publication date	Apr 13, 2021
Grant date	Apr 13, 2021

Abstract

The invention relates to a crystal (C) consisting of at least 95% by weight of 4,4′-dichlorodiphenylsulfoxide, 0 to 2% by weight of impurities and 0 to 3% by weight of an organic solvent (os). Moreover, the present invention relates to a crystal composition (CC) comprising crystals (C) and a process for the production of the crystal composition (CC) and the crystal (C).

First claim

The invention claimed is:

1. A crystal composition (CC), comprising crystals (C), wherein the crystals (C) consist of
(a) at least 95% by weight of 4,4′-dichlorodiphenylsulfoxide,
(b) 0 to 2% by weight of impurities, and
(c) 0 to 3% by weight of an organic solvent (os),
based on a total weight of the crystals (C) comprised in the crystal composition (CC), wherein the crystal composition (CC) has
a d10, 3 -value in a range of 100 to 400 μm,
a d50, 3 -value in a range of 300 to 800 μm and
a d90, 3 -value in a range of 700 to 1500 μm,
wherein the d10, 3 -value is lower than the d50, 3 -value and the d50, 3 -value is lower than the d90, 3 -value.

2. The crystal composition (CC) of claim 1 , wherein the crystal composition (CC) comprises at least 95% by weight of the crystals (C), based on a total weight of the crystal composition (CC).

3. The crystal composition (CC) of claim 1 , wherein the crystal composition (CC) has a bulk density in a range of 600 to 950 kg/m 3 .

4. The crystal composition (CC) of claim 1 , wherein an average aspect ratio of the crystals (C) is in a range of 0.2 to 1.

5. The crystal composition (CC) of claim 1 , wherein an average sphericity of the crystals (C) is in a range of 0.75 to 0.85.

6. The crystal composition (CC) of claim 1 , wherein a Hausner ratio is in a range of 1.05 to 1.27.

7. The crystal composition (CC) of claim 1 , wherein a unit cell of the crystals (C) is monoclinic, space group C 2/m, cell lengths a=16.05 ű0.05 Å, b=9.82 ű0.05 Å, c=7.21 ű0.05 Å, cell angles alpha 90°±0.1°, beta 95.7°±0.1°, gamma 90°±0.1°, and a cell volume 1131.5 Å 3 ±1 Å 3 .

8. A crystal (C) consisting of
(a) at least 95% by weight 4,4′-dichlorodiphenylsulfoxide,
(b) 0 to 2% by weight of impurities, and
(c) 0 to 3% by weight of an organic solvent (os),
based in each case on a total weight of the crystal (C),
wherein an outer surface of the crystal (C) comprises
i) a six-sided base surface (bsu),
ii) a six-sided top surface (tsu), and
iii) six side surfaces (ssu 1 to ssu 6 ), joining the corresponding sides of the six-sided base surface (bsu) and the six-sided top surface (tsu).

9. The crystal (C) of claim 8 , wherein the six-sided base surface (bsu), the six-sided top surface (tsu) and the six side surfaces (ssu 1 to ssu 6 ) account for at least 90% of the outer surface of the crystal (C).

10. The crystal (C) of claim 8 , wherein a diameter (db) of the six-sided base surface (bsu) and a diameter (dt) of the six-sided top surface (tsu) are each independently in a range of 50 to 1500 μm.

11. The crystal (C) of claim 8 , wherein a length (l 1 ) of the first side surface (ssu 1 ), a length (l 2 ) of the second side surface (ssu 2 ), a length (l 3 ) of the third side surface (ssu 3 ), a length (l 4 ) of the fourth side surface (ssu 4 ), a length (l 5 ) of the fifth side surface (ssu 5 ) and a length (l 6 ) of the sixth side surface (ssu 6 ) are each independently in a range of 100 to 3000 μm.

12. The crystal (C) of claim 8 , wherein a ratio of an average of a diameter (db) of the six-sided base surface (bsu) and a diameter (dt) of the six-sided top surface (tsu) to an average of a length (l 1 ) of the first side surface (ssu 1 ), a length (l 2 ) of the second side surface (ssu 2 ), a length (l 3 ) of the third side surface (ssu 3 ), a length (l 4 ) of the fourth side surface (ssu 4 ), a length (l 5 ) of the fifth side surface (ssu 5 ) and a length (l 6 ) of the sixth side surface (ssu 6 ) is in a range of 0.2 to 1.

13. The crystal (C) of claim 8 , wherein the impurities (b) comprise at least 90% by weight of one or more compounds selected from the group consisting of 2,4′-dichlorodiphenylsulfoxide, 3,4′-dichlorodiphenylsulfoxide, 2,2′-dichlorodiphenylsulfoxide, 4,4′-dichlorodiphenylsulfide, and one or more aluminum compounds based on a total weight of the impurities (b) comprised in the crystal (C).

14. The crystal composition (CC) of claim 1 , obtained by a process comprising:
I) cooling a first liquid mixture comprising 4,4′-dichlorodiphenylsulfoxide dissolved in an organic solvent (os) to obtain a suspension comprising crystallized 4,4′-dichlorodiphenylsulfoxide and the organic solvent (os),
II) filtering the suspension obtained in I) to obtain a filtrate comprising 4,4′-dichlorodiphenylsulfoxide dissolved in the organic solvent (os), wherein the filtrate has a lower concentration of 4,4′-dichlorodiphenylsulfoxide compared to the first liquid mixture, and a filter residue comprising the crystallized 4,4′-dichlorodiphenylsulfoxide,
III) concentrating the filtrate obtained in II) to obtain a second liquid mixture, wherein the second liquid mixture has a higher concentration of 4,4′-dichlorodiphenylsulfoxide compared to the filtrate,
IV) recycling at least a part of the second liquid mixture obtained in III) into I), and
V) drying the filter residue obtained in II) to obtain the crystal composition (CC).

15. The crystal (C) of claim 8 , obtained by a process comprising:
I) cooling a liquid mixture comprising 4,4′-dichlorodiphenylsulfoxide dissolved in an organic solvent (os) to obtain a suspension comprising crystallized 4,4′-dichlorodiphenylsulfoxide and the organic solvent (os),
II) filtering the suspension obtained in I) to obtain a filtrate comprising 4,4′-dichlorodiphenylsulfoxide dissolved in the organic solvent (os), wherein the filtrate has a lower concentration of 4,4′-dichlorodiphenylsulfoxide compared to the liquid mixture, and a filter residue comprising the crystallized 4,4′-dichlorodiphenylsulfoxide,
V) drying the filter residue obtained in II) to obtain a crystal composition (CC), and
VI) separating a crystal (C) from the crystal composition (CC) obtained in V).

16. A method of producing a monomer, polymer, or pharmaceutical, the method comprising reacting a crystal composition (CC) as an intermediate,
wherein the crystal composition (CC) comprises crystals (C), wherein the crystals (C) consist of
(a) at least 95% by weight of 4,4′-dichlorodiphenylsulfoxide,
(b) 0 to 2% by weight of impurities, and
(c) 0 to 3% by weight of an organic solvent (os),
based on a total weight of the crystals (C) comprised in the crystal composition (CC), wherein the crystal composition (CC) has
a d10, 3 -value in a range of 100 to 400 μm,
a d50, 3 -value in a range of 300 to 800 μm and
a d90, 3 -value in a range of 700 to 1500 μm,
wherein the d10, 3 -value is lower than the d50, 3 -value and the d50, 3 -value is lower than the d90, 3 -value.

Assignees

• Basf Se

Inventors

• Thiel Indre
• Schuetz Christian
• Blei Stefan
• Gao Jun
• Metzger Lukas

Classifications

• C07C315/06 Primary

  Separation; Purification; Stabilisation; Use of additives · CPC title

• C07B2200/13

  Crystalline forms, e.g. polymorphs · CPC title

• C07C317/14 Primary

  having sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings · CPC title

• C07C2601/16

  the ring being unsaturated · CPC title