CA2465294A1 - Recovery and recycling of chiral tartaric acid resolving agents - Google Patents
Recovery and recycling of chiral tartaric acid resolving agents Download PDFInfo
- Publication number
- CA2465294A1 CA2465294A1 CA002465294A CA2465294A CA2465294A1 CA 2465294 A1 CA2465294 A1 CA 2465294A1 CA 002465294 A CA002465294 A CA 002465294A CA 2465294 A CA2465294 A CA 2465294A CA 2465294 A1 CA2465294 A1 CA 2465294A1
- Authority
- CA
- Canada
- Prior art keywords
- tartaric acid
- process according
- acid
- substituted
- recovery
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 239000011975 tartaric acid Substances 0.000 title claims abstract description 42
- 239000003795 chemical substances by application Substances 0.000 title claims abstract description 30
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 title claims abstract description 27
- 235000002906 tartaric acid Nutrition 0.000 title claims abstract description 27
- 238000011084 recovery Methods 0.000 title claims abstract description 11
- 238000004064 recycling Methods 0.000 title description 2
- 238000000034 method Methods 0.000 claims abstract description 32
- 150000003892 tartrate salts Chemical class 0.000 claims abstract description 29
- 239000003960 organic solvent Substances 0.000 claims abstract description 15
- 239000008346 aqueous phase Substances 0.000 claims abstract description 14
- 239000002253 acid Substances 0.000 claims abstract description 12
- 229910052500 inorganic mineral Inorganic materials 0.000 claims abstract description 9
- 239000011707 mineral Substances 0.000 claims abstract description 9
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical group CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims description 18
- 239000002585 base Substances 0.000 claims description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 11
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical class N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 6
- 239000012453 solvate Substances 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 4
- 239000006184 cosolvent Substances 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 3
- 229910021529 ammonia Inorganic materials 0.000 claims description 3
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 150000003839 salts Chemical class 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000002904 solvent Substances 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical group [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 235000010755 mineral Nutrition 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 230000008929 regeneration Effects 0.000 description 4
- 238000011069 regeneration method Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- STCJUTRPNGTJGE-UHFFFAOYSA-N [1-benzyl-4-(4-fluorophenyl)-3,6-dihydro-2h-pyridin-3-yl]methanol Chemical compound C1C=C(C=2C=CC(F)=CC=2)C(CO)CN1CC1=CC=CC=C1 STCJUTRPNGTJGE-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229960000443 hydrochloric acid Drugs 0.000 description 3
- 235000011167 hydrochloric acid Nutrition 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000012452 mother liquor Substances 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- MTJGVAJYTOXFJH-UHFFFAOYSA-N 3-aminonaphthalene-1,5-disulfonic acid Chemical compound C1=CC=C(S(O)(=O)=O)C2=CC(N)=CC(S(O)(=O)=O)=C21 MTJGVAJYTOXFJH-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 2
- 238000010268 HPLC based assay Methods 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- -1 amine compounds Chemical class 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- CEXCHYIGFUAPKW-UHFFFAOYSA-N methanol;piperidine Chemical class OC.C1CCNCC1 CEXCHYIGFUAPKW-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 230000000717 retained effect Effects 0.000 description 2
- LSROBYZLBGODRN-UHFFFAOYSA-N 1-aminopyrrolidin-2-one Chemical class NN1CCCC1=O LSROBYZLBGODRN-UHFFFAOYSA-N 0.000 description 1
- NZVZVGPYTICZBZ-UHFFFAOYSA-N 1-benzylpiperidine Chemical class C=1C=CC=CC=1CN1CCCCC1 NZVZVGPYTICZBZ-UHFFFAOYSA-N 0.000 description 1
- VSWICNJIUPRZIK-UHFFFAOYSA-N 2-piperideine Chemical class C1CNC=CC1 VSWICNJIUPRZIK-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 235000015424 sodium Nutrition 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B57/00—Separation of optically-active compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/52—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/60—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0127346A GB2382074A (en) | 2001-11-14 | 2001-11-14 | Recovery of chiral tartaric acid resolving agents |
| GB0127346.5 | 2001-11-14 | ||
| PCT/EP2002/012494 WO2003042132A1 (en) | 2001-11-14 | 2002-11-08 | Recovery and recycling of chiral tartaric acid resolving agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2465294A1 true CA2465294A1 (en) | 2003-05-22 |
Family
ID=9925776
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002465294A Abandoned CA2465294A1 (en) | 2001-11-14 | 2002-11-08 | Recovery and recycling of chiral tartaric acid resolving agents |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US7838700B2 (enExample) |
| EP (1) | EP1446372B1 (enExample) |
| JP (1) | JP2005509011A (enExample) |
| AT (1) | ATE428677T1 (enExample) |
| CA (1) | CA2465294A1 (enExample) |
| DE (1) | DE60232006D1 (enExample) |
| ES (1) | ES2324772T3 (enExample) |
| GB (1) | GB2382074A (enExample) |
| HU (1) | HUP0402368A3 (enExample) |
| IL (2) | IL161540A0 (enExample) |
| WO (1) | WO2003042132A1 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1315777C (zh) | 2003-01-16 | 2007-05-16 | 东丽泛应化学(股) | 旋光二酰基酒石酸的回收方法 |
| ES2264378B1 (es) * | 2005-05-09 | 2007-11-01 | Ragactives, S.L. | Procedimiento para la resolucion de 2-amino-6propilamino-4,5,6,7-tetrahidrobenzotiazol y compuestos intermedios. |
| EP1736462A1 (en) * | 2005-06-22 | 2006-12-27 | Sandoz AG | Recovery of optically active tartaric acid resolving agents |
| MD4504C1 (ro) * | 2016-04-13 | 2018-03-31 | Общественное Учреждение "Научно-Практический Институт Садоводства И Пищевых Технологий" | Procedeu de obţinere a acidului tartric din tartratul de calciu obţinut din deşeuri vinicole |
| JP7516029B2 (ja) | 2018-11-16 | 2024-07-16 | アムジエン・インコーポレーテツド | Ｋｒａｓ ｇ１２ｃ阻害剤化合物の重要な中間体の改良合成法 |
| MX2023003983A (es) * | 2020-10-07 | 2023-04-24 | Amgen Inc | Procedimiento para racemizar y aislar atropisomeros de 7-cloro-6-fluoro-1-(2-isopropil-4-metilpiridin-3-il)pirido[2,3-d] pirimidin-2,4(1h,3h)-diona. |
| CN112358398A (zh) * | 2020-11-19 | 2021-02-12 | 山东新华制药股份有限公司 | D-(+)-二对甲苯甲酰酒石酸的回收制备方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH09176115A (ja) * | 1995-12-28 | 1997-07-08 | Koei Chem Co Ltd | 光学活性なｎ−ベンジル−３−アミノピロリジンの製造方法 |
| HU221921B1 (hu) | 1996-07-08 | 2003-02-28 | Richter Gedeon Vegyészeti Gyár Rt. | N-benzil-piperidin- és tetrahidropiridinszármazékok és eljárás azok előállítására |
| CN1173929C (zh) * | 1999-10-19 | 2004-11-03 | 中国科学院成都有机化学研究所 | 光学纯肾上腺素类β-激动剂的组合拆分制备法 |
| GB9930577D0 (en) | 1999-12-23 | 2000-02-16 | Smithkline Beecham Plc | Novel process |
-
2001
- 2001-11-14 GB GB0127346A patent/GB2382074A/en not_active Withdrawn
-
2002
- 2002-11-08 WO PCT/EP2002/012494 patent/WO2003042132A1/en not_active Ceased
- 2002-11-08 HU HU0402368A patent/HUP0402368A3/hu unknown
- 2002-11-08 CA CA002465294A patent/CA2465294A1/en not_active Abandoned
- 2002-11-08 US US10/495,359 patent/US7838700B2/en not_active Expired - Fee Related
- 2002-11-08 DE DE60232006T patent/DE60232006D1/de not_active Expired - Lifetime
- 2002-11-08 AT AT02803000T patent/ATE428677T1/de not_active IP Right Cessation
- 2002-11-08 JP JP2003543972A patent/JP2005509011A/ja active Pending
- 2002-11-08 IL IL16154002A patent/IL161540A0/xx active IP Right Grant
- 2002-11-08 ES ES02803000T patent/ES2324772T3/es not_active Expired - Lifetime
- 2002-11-08 EP EP02803000A patent/EP1446372B1/en not_active Expired - Lifetime
-
2004
- 2004-04-21 IL IL161540A patent/IL161540A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| GB2382074A (en) | 2003-05-21 |
| IL161540A (en) | 2011-03-31 |
| IL161540A0 (en) | 2004-09-27 |
| ATE428677T1 (de) | 2009-05-15 |
| US7838700B2 (en) | 2010-11-23 |
| DE60232006D1 (de) | 2009-05-28 |
| EP1446372B1 (en) | 2009-04-15 |
| GB0127346D0 (en) | 2002-01-02 |
| EP1446372A1 (en) | 2004-08-18 |
| ES2324772T3 (es) | 2009-08-14 |
| HUP0402368A2 (hu) | 2005-03-29 |
| HUP0402368A3 (en) | 2008-02-28 |
| JP2005509011A (ja) | 2005-04-07 |
| WO2003042132A1 (en) | 2003-05-22 |
| US20050085665A1 (en) | 2005-04-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |
Effective date: 20130212 |