BE521899A - - Google Patents

Info

Publication number

BE521899A

BE521899A BE521899DA BE521899A BE 521899 A BE521899 A BE 521899A BE 521899D A BE521899D A BE 521899DA BE 521899 A BE521899 A BE 521899A

Authority

BE

Belgium

Prior art keywords

acid

deoxycholeic

until

june

mixture

Prior art date

Links

• Espacenet
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• 239000002253 acid Substances 0.000 claims description 62
• KXGVEGMKQFWNSR-LLQZFEROSA-N deoxycholic acid Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 KXGVEGMKQFWNSR-LLQZFEROSA-N 0.000 claims description 24
• 229960003964 deoxycholic acid Drugs 0.000 claims description 24
• 239000000203 mixture Substances 0.000 claims description 20
• 150000001875 compounds Chemical class 0.000 claims description 17
• 238000002425 crystallisation Methods 0.000 claims description 17
• 230000008025 crystallization Effects 0.000 claims description 17
• 239000000126 substance Substances 0.000 claims description 13
• 230000020477 pH reduction Effects 0.000 claims description 10
• 238000000034 method Methods 0.000 claims description 9
• 238000000926 separation method Methods 0.000 claims description 8
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
• 230000000694 effects Effects 0.000 claims description 3
• 150000002576 ketones Chemical class 0.000 claims description 3
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
• 150000003839 salts Chemical class 0.000 claims description 2
• 239000007864 aqueous solution Substances 0.000 claims 1
• 239000003795 chemical substances by application Substances 0.000 claims 1
• 239000013078 crystal Substances 0.000 claims 1
• 239000000463 material Substances 0.000 claims 1
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
• 210000000941 bile Anatomy 0.000 description 8
• 229910052739 hydrogen Inorganic materials 0.000 description 8
• 239000001257 hydrogen Substances 0.000 description 8
• -1 hydrogen ions Chemical class 0.000 description 8
• 239000008096 xylene Substances 0.000 description 8
• CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 7
• 150000007513 acids Chemical class 0.000 description 7
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
• 239000000243 solution Substances 0.000 description 6
• 238000003756 stirring Methods 0.000 description 6
• 238000001914 filtration Methods 0.000 description 4
• 239000000061 acid fraction Substances 0.000 description 3
• MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 3
• 239000012452 mother liquor Substances 0.000 description 3
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
• 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
• 238000005119 centrifugation Methods 0.000 description 2
• 238000001816 cooling Methods 0.000 description 2
• 238000010494 dissociation reaction Methods 0.000 description 2
• 230000005593 dissociations Effects 0.000 description 2
• 239000012535 impurity Substances 0.000 description 2
• 229910052500 inorganic mineral Inorganic materials 0.000 description 2
• 239000011707 mineral Substances 0.000 description 2
• 239000002244 precipitate Substances 0.000 description 2
• 238000001556 precipitation Methods 0.000 description 2
• 239000007787 solid Substances 0.000 description 2
• HSINOMROUCMIEA-FGVHQWLLSA-N (2s,4r)-4-[(3r,5s,6r,7r,8s,9s,10s,13r,14s,17r)-6-ethyl-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-methylpentanoic acid Chemical class C([C@@]12C)C[C@@H](O)C[C@H]1[C@@H](CC)[C@@H](O)[C@@H]1[C@@H]2CC[C@]2(C)[C@@H]([C@H](C)C[C@H](C)C(O)=O)CC[C@H]21 HSINOMROUCMIEA-FGVHQWLLSA-N 0.000 description 1
• OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical class [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 1
• NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
• UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
• DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
• 150000001447 alkali salts Chemical class 0.000 description 1
• 239000012670 alkaline solution Substances 0.000 description 1
• 229910021529 ammonia Inorganic materials 0.000 description 1
• 239000000908 ammonium hydroxide Substances 0.000 description 1
• 239000002585 base Substances 0.000 description 1
• 239000003613 bile acid Substances 0.000 description 1
• 238000010924 continuous production Methods 0.000 description 1
• 239000002178 crystalline material Substances 0.000 description 1
• 229940117389 dichlorobenzene Drugs 0.000 description 1
• 150000004816 dichlorobenzenes Chemical class 0.000 description 1
• 235000014113 dietary fatty acids Nutrition 0.000 description 1
• 239000003792 electrolyte Substances 0.000 description 1
• 238000000605 extraction Methods 0.000 description 1
• 239000000194 fatty acid Substances 0.000 description 1
• 229930195729 fatty acid Natural products 0.000 description 1
• 150000004665 fatty acids Chemical class 0.000 description 1
• 238000002955 isolation Methods 0.000 description 1
• 238000004519 manufacturing process Methods 0.000 description 1
• 238000012986 modification Methods 0.000 description 1
• 230000004048 modification Effects 0.000 description 1
• 238000010899 nucleation Methods 0.000 description 1
• 150000002894 organic compounds Chemical class 0.000 description 1
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
• 229910052700 potassium Inorganic materials 0.000 description 1
• 239000011591 potassium Substances 0.000 description 1
• 230000001376 precipitating effect Effects 0.000 description 1
• 238000000746 purification Methods 0.000 description 1
• 230000000630 rising effect Effects 0.000 description 1
• 229910052708 sodium Inorganic materials 0.000 description 1
• 239000011734 sodium Substances 0.000 description 1
• 239000002904 solvent Substances 0.000 description 1
• 239000000725 suspension Substances 0.000 description 1
• 150000003509 tertiary alcohols Chemical class 0.000 description 1
• 239000012855 volatile organic compound Substances 0.000 description 1