CRYSTAL COMPOSITION (CC) COMPRISING 4,4'-DICHLORODIPHENYLSULFOXIDE CRYSTALS (C)

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).

Claims

1. 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 the total weight of the crystals (C) contained in the crystal composition (CC), wherein the crystal composition (CC) has a d10,.sub.3 -value in the range of 100 to 400 μm, a d50,.sub.3 -value in the range of 300 to 800 μm and a d90,.sub.3 -value in the range of 700 to 1500 μm, wherein the d10,.sub.3-value is lower than the d50,.sub.3-value and the d50,.sub.3-value is lower than the d90,.sub.3-value.

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

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

4. A crystal composition (CC) according to claim 1, wherein the average aspect ratio of the crystals (C) are in the range of 0.2 to 1.

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

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

7. A crystal composition (CC) according to claim 1, wherein the 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.sup.3±1 Å.sup.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 the total weight of the crystal (C), wherein the outer surface of the crystal (C) comprises i) a six-sided base surface (bsu) and ii) a six-sided top surface (tsu) and iii) six side surfaces (ssu1 to ssu6), joining the corresponding sides of the six-sided base surface (bsu) and the six-sided top surface (tsu).

9. A crystal (C) according to claim 8, wherein the six-sided base surface (bsu), the six-sided top surface (tsu) and the six side surfaces (ssu1 to ssu6) account for at least 90% of the outer surface of the crystal (C).

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

11. A crystal (C) according to claim 8, wherein the length (I1) of the first side surface (ssu1), the length (I2) of the second side surface (ssu2), the length (I3) of the third side surface (ssu3), the length (I4) of the fourth side surface (ssu4), the length (I5) of the fifth side surface (ssu5) and the length (I6) of the sixth side surface (ssu6) are each independently in the range of 100 to 3000 μm.

12. A crystal (C) according to claim 8, wherein the ratio of the average of the diameter (db) and the diameter (dt) to the average of the length (I1), the length (I2), the length (I3), the length (I4), the length (I5) and the length (I6) is in the range of 0.2 to 1.

13. Crystal (C) according to 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 the total weight of the impurities (b) contained in the crystal (C).

14. A crystal composition (CC) according to claim 1 obtained by a process comprising the steps: 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 step 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 step 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 step III) into step I), and V) drying the filter residue obtained in step II) to obtain the crystal composition (CC), wherein the organic solvent is chlorobenzene, toluene, xylene, mesitylene, methanol or a mixture of two or more of said solvents.

15. A crystal (C) obtained by the process of claim 14, further comprising the step: VI) separating a crystal (C) out of the crystal composition (CC) obtained in step V).

16. Use of the crystal composition (CC) as an intermediate for the production of at least one product selected from the group consisting of monomers, polymers and pharmaceuticals.

Description

FIGURES AND REFERENCE SIGN LIST

[0140] FIG. 1A shows the net of a prism with a symmetrical six-sided base surface bsu and a symmetrical six-sided top surface tsu and six side surfaces ssu1 to ssu6

[0141] FIG. 1B shows the top view of the top surface tsu of an asymmetrical prism with a six-sided top surface tsu

[0142] FIG. 1C shows the first side surface ssu of an asymmetrical six-sided prism

[0143] FIG. 1D shows one embodiment of the geometry of the outer surface of the crystal C according to the invention

[0144] FIG. 2A shows another embodiment of the geometry of the outer surface of the crystal C according to the invention

[0145] FIG. 2B shows a photo taken with a light microscope of the geometry of the outer surface of the crystal C according to the invention with marked up edges and reference signs

[0146] FIG. 3A shows a photo taken with a light microscope of the crystal composition CC showing crystals C (500 μm)

[0147] FIG. 3B shows a photo taken with a light microscope of the crystal composition CC showing crystals C (200 μm)

[0148] FIG. 4A shows a photo taken with a light microscope of 4,4′-dichlorodiphenylsulfoxide in particulate powder form obtained from abcr GmbH (500 μm)

[0149] FIG. 4B shows a photo taken with a light microscope of 4,4′-dichlorodiphenylsulfoxide in particulate powder form obtained from abcr GmbH (200 μm)

[0150] FIG. 5 shows a photo taken with a light microscope of 4,4′-dichlorodiphenylsulfoxide in particulate powder form obtained from Alfa Aesar (500 μm)

[0151] FIG. 6A shows a photo taken with a light microscope of 4,4′-dichlorodiphenylsulfoxide in particulate powder form obtained from TCI GmbH (500 μm)

[0152] FIG. 6B shows a photo taken with a light microscope of 4,4′-dichlorodiphenylsulfoxide in particulate powder form obtained from TCI GmbH (1 mm)

[0153] FIG. 7A shows a photo taken with a light microscope of 4,4′-dichlorodiphenylsulfoxide in particulate powder form recrystallized from diethyl ether (500 μm)

[0154] FIG. 7B shows a photo taken with a light microscope of 4,4′-dichlorodiphenylsulfoxide in particulate powder form recrystallized form diethylether (200 μm)

[0155] FIG. 8A illustrates the measurement of X.sub.c min

[0156] FIG. 8B illustrates the measurement of X.sub.Fe max

[0157] FIG. 9A shows a photo taken with a light microscope of 4,4′-dichlorodiphenylsulfoxide in particulate powder form recrystallized from chloroform (200 μm)

[0158] FIG. 9B shows a photo taken with a light microscope of 4,4′-dichlorodiphenylsulfoxide in particulate powder form recrystallized from chloroform (500 μm)

[0159] FIG. 10 shows a photo taken with a light microscope of 4,4′-dichlorodiphenylsulfoxide in particulate powder form recrystallized from ethyl acetate (500 μm)

[0160] C crystal [0161] bsu six-sided base surface of the crystal (C) [0162] bsi1 first side of the six-sided base surface bsu [0163] bsi2 second side of the six-sided base surface bsu [0164] bsi3 third side of the six-sided base surface bsu [0165] bsi4 fourth side of the six-sided base surface bsu [0166] bsi5 fifth side of the six-sided base surface bsu [0167] bsi6 sixth side of the six-sided base surface bsu [0168] cb1 first corner of the six-sided base surface bsu [0169] cb2 second corner of the six-sided base surface bsu [0170] cb3 third corner of the six-sided base surface bsu [0171] cb4 fourth corner of the six-sided base surface bsu [0172] cb5 fifth corner of the six-sided base surface bsu [0173] cb6 sixth corner of the six-sided base surface bsu [0174] db diameter of the six-sided base surface bsu [0175] db14 shortest distance between the first corner cb1 and the fourth corner cb4 [0176] db25 shortest distance between the second corner cb2 and the [0177] fifth corner cb5 [0178] db36 shortest distance between the third corner cb3 and the sixth corner cb6 [0179] tsu six-sided top surface of the crystal C [0180] tsi1 first side of the six-sided top surface tsu [0181] tsi2 second side of the six-sided top surface tsu [0182] tsi3 third side of the six-sided top surface tsu [0183] tsi4 fourth side of the six-sided top surface tsu [0184] tsi5 fifth side of the six-sided top surface tsu [0185] tsi6 sixth side of the six-sided top surface tsu [0186] ct1 first corner of the six-sided top surface tsu [0187] ct2 second corner of the six-sided top surface tsu [0188] ct3 third corner of the six-sided top surface tsu [0189] ct4 fourth corner of the six-sided top surface tsu [0190] ct5 fifth corner of the six-sided top surface tsu [0191] ct6 sixth corner of the six-sided top surface tsu [0192] dt diameter of the six-sided top surface tsu [0193] dt14 shortest distance between the first corner ct1 and the fourth corner ct4 [0194] dt25 shortest distance between the second corner ct2 and the fifth corner ct5 [0195] dt36 shortest distance between the third corner ct3 and the sixth corner ct6 [0196] ssu1 first side surface of the crystal (C) [0197] ssu2 second side surface of the crystal (C) [0198] ssu3 third side surface of the crystal (C) [0199] ssu4 fourth side surface of the crystal (C) [0200] ssu5 fifth side surface of the crystal (C) [0201] ssu6 sixth side surface of the crystal (C) [0202] I1 length of the first side surface (ssu1) [0203] I2 length of the second side surface (ssu2) [0204] I3 length of the third side surface (ssu3) [0205] I4 length of the fourth side surface (ssu4) [0206] I5 length of the fifth side surface (ssu5) [0207] I6 length of the sixth side surface (ssu6) [0208] I11 shortest distance between the first corner ct1 and the first corner bt1 [0209] I22 shortest distance between the second corner ct2 and the second corner bt2 [0210] I33 shortest distance between the third corner ct3 and the third corner bt3 [0211] I44 shortest distance between the fourth corner ct4 and the fourth corner bt4 [0212] I55 shortest distance between the fifth corner ct5 and the fifth corner bt5 [0213] I66 shortest distance between the sixth corner ct6 and the sixth corner bt6