DE60219953T2 - Trennung von diastereoisomeren - Google Patents
Trennung von diastereoisomeren Download PDFInfo
- Publication number
- DE60219953T2 DE60219953T2 DE60219953T DE60219953T DE60219953T2 DE 60219953 T2 DE60219953 T2 DE 60219953T2 DE 60219953 T DE60219953 T DE 60219953T DE 60219953 T DE60219953 T DE 60219953T DE 60219953 T2 DE60219953 T2 DE 60219953T2
- Authority
- DE
- Germany
- Prior art keywords
- lewis acid
- diastereoisomers
- mixture
- starting mixture
- liquid
- 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.)
- Expired - Lifetime
Links
- 238000000926 separation method Methods 0.000 title abstract description 25
- 239000000203 mixture Substances 0.000 claims abstract description 80
- 239000002841 Lewis acid Substances 0.000 claims abstract description 56
- 239000007788 liquid Substances 0.000 claims abstract description 48
- 238000000034 method Methods 0.000 claims abstract description 46
- 150000007517 lewis acids Chemical class 0.000 claims abstract description 45
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 33
- 150000001875 compounds Chemical class 0.000 claims abstract description 14
- -1 Lewis acid compound Chemical class 0.000 claims abstract description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- GGHNHVFHLSKAGV-UHFFFAOYSA-N 4,5-bis(methoxymethyl)octane Chemical compound CCCC(COC)C(CCC)COC GGHNHVFHLSKAGV-UHFFFAOYSA-N 0.000 claims description 5
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052749 magnesium Inorganic materials 0.000 claims description 3
- 229910052719 titanium Inorganic materials 0.000 claims description 3
- 229910052723 transition metal Inorganic materials 0.000 claims description 3
- 150000003624 transition metals Chemical class 0.000 claims description 3
- 125000006659 (C1-C20) hydrocarbyl group Chemical group 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 229910007926 ZrCl Inorganic materials 0.000 claims description 2
- 229910052791 calcium Inorganic materials 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- LBFYQOYPPWREAX-UHFFFAOYSA-N diethyl 2,3-di(butan-2-yl)butanedioate Chemical compound CCOC(=O)C(C(C)CC)C(C(C)CC)C(=O)OCC LBFYQOYPPWREAX-UHFFFAOYSA-N 0.000 claims description 2
- LQLYZPTVIYLWPB-UHFFFAOYSA-N dimethyl 2,4-dimethylpentanedioate Chemical compound COC(=O)C(C)CC(C)C(=O)OC LQLYZPTVIYLWPB-UHFFFAOYSA-N 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 229910052759 nickel Inorganic materials 0.000 claims description 2
- 230000000737 periodic effect Effects 0.000 claims description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 229910052726 zirconium Inorganic materials 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 238000000053 physical method Methods 0.000 abstract description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 45
- 239000007787 solid Substances 0.000 description 27
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
- 239000002904 solvent Substances 0.000 description 17
- 238000007792 addition Methods 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- WGFNXLQURMLAGC-UHFFFAOYSA-N diethyl 2,3-di(propan-2-yl)butanedioate Chemical compound CCOC(=O)C(C(C)C)C(C(C)C)C(=O)OCC WGFNXLQURMLAGC-UHFFFAOYSA-N 0.000 description 10
- 239000007791 liquid phase Substances 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 8
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 5
- 238000004587 chromatography analysis Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 150000001722 carbon compounds Chemical class 0.000 description 1
- 238000007385 chemical modification Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000000593 degrading effect Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 238000001033 granulometry Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- KJJBSBKRXUVBMX-UHFFFAOYSA-N magnesium;butane Chemical compound [Mg+2].CCC[CH2-].CCC[CH2-] KJJBSBKRXUVBMX-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001612 separation test Methods 0.000 description 1
- 238000011172 small scale experimental method Methods 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000006104 solid solution Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B57/00—Separation of optically-active compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP01205252 | 2001-12-24 | ||
| EP01205252 | 2001-12-24 | ||
| PCT/EP2002/014875 WO2003055831A1 (en) | 2001-12-24 | 2002-12-20 | Separation of diastereoisomers |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60219953D1 DE60219953D1 (de) | 2007-06-14 |
| DE60219953T2 true DE60219953T2 (de) | 2008-01-17 |
Family
ID=8181566
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60219953T Expired - Lifetime DE60219953T2 (de) | 2001-12-24 | 2002-12-20 | Trennung von diastereoisomeren |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US7067690B2 (https=) |
| EP (1) | EP1458661B1 (https=) |
| JP (1) | JP4485797B2 (https=) |
| CN (1) | CN100390111C (https=) |
| AT (1) | ATE361268T1 (https=) |
| DE (1) | DE60219953T2 (https=) |
| WO (1) | WO2003055831A1 (https=) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL374508A1 (en) | 2002-08-01 | 2005-10-31 | Basell Poliolefine Italia S.P.A. | Highly stereoregular polypropylene with improved properties |
| JP2011506718A (ja) * | 2007-12-20 | 2011-03-03 | バーゼル・ポリオレフィン・イタリア・ソチエタ・ア・レスポンサビリタ・リミタータ | 改良された特性を有する高立体規則性ポリプロピレン |
| CN116178152A (zh) * | 2022-11-17 | 2023-05-30 | 河南科弘生物科技有限公司 | 一种2，3-二仲丁烯琥珀酸二乙酯的制备方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1216190A (en) | 1967-05-15 | 1970-12-16 | Ici Ltd | Resolution of enantiomorphic compounds |
| AU5575898A (en) | 1997-01-24 | 1998-08-18 | Kissei Pharmaceutical Co. Ltd. | Process for producing optically active benzylsuccinic acid and intermediate therefor |
| IT1302029B1 (it) | 1998-08-19 | 2000-07-20 | Montech Usa Inc | Processo per produrre composizioni polimeriche eterofasiche ecomposizioni cosi' ottenute |
-
2002
- 2002-12-20 US US10/499,273 patent/US7067690B2/en not_active Expired - Lifetime
- 2002-12-20 WO PCT/EP2002/014875 patent/WO2003055831A1/en not_active Ceased
- 2002-12-20 CN CNB028259750A patent/CN100390111C/zh not_active Expired - Fee Related
- 2002-12-20 EP EP02796762A patent/EP1458661B1/en not_active Expired - Lifetime
- 2002-12-20 AT AT02796762T patent/ATE361268T1/de not_active IP Right Cessation
- 2002-12-20 JP JP2003556367A patent/JP4485797B2/ja not_active Expired - Fee Related
- 2002-12-20 DE DE60219953T patent/DE60219953T2/de not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| EP1458661B1 (en) | 2007-05-02 |
| CN1608041A (zh) | 2005-04-20 |
| CN100390111C (zh) | 2008-05-28 |
| JP4485797B2 (ja) | 2010-06-23 |
| US7067690B2 (en) | 2006-06-27 |
| DE60219953D1 (de) | 2007-06-14 |
| ATE361268T1 (de) | 2007-05-15 |
| EP1458661A1 (en) | 2004-09-22 |
| WO2003055831A1 (en) | 2003-07-10 |
| JP2005513150A (ja) | 2005-05-12 |
| US20050171379A1 (en) | 2005-08-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition |