PL85292B1 - - Google Patents
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- Publication number
- PL85292B1 PL85292B1 PL1972156202A PL15620272A PL85292B1 PL 85292 B1 PL85292 B1 PL 85292B1 PL 1972156202 A PL1972156202 A PL 1972156202A PL 15620272 A PL15620272 A PL 15620272A PL 85292 B1 PL85292 B1 PL 85292B1
- Authority
- PL
- Poland
- Prior art keywords
- acid
- salt
- carbinol
- diphenyl
- separated
- Prior art date
Links
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 29
- 239000002253 acid Substances 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 11
- 238000000926 separation method Methods 0.000 claims description 11
- 239000002244 precipitate Substances 0.000 claims description 7
- 239000000706 filtrate Substances 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims 1
- 239000000243 solution Substances 0.000 description 12
- 239000000203 mixture Substances 0.000 description 9
- 229960004193 dextropropoxyphene Drugs 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- XLMALTXPSGQGBX-GCJKJVERSA-N dextropropoxyphene Chemical compound C([C@](OC(=O)CC)([C@H](C)CN(C)C)C=1C=CC=CC=1)C1=CC=CC=C1 XLMALTXPSGQGBX-GCJKJVERSA-N 0.000 description 6
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 241000723346 Cinnamomum camphora Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-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
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000779819 Syncarpia glomulifera Species 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 230000003444 anaesthetic effect Effects 0.000 description 1
- 239000003434 antitussive agent Substances 0.000 description 1
- 229940124584 antitussives Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 229960000846 camphor Drugs 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- -1 for example Substances 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 230000003533 narcotic effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000001739 pinus spp. Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 229940065347 propoxyphene hydrochloride Drugs 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- HIEHAIZHJZLEPQ-UHFFFAOYSA-M sodium;naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 HIEHAIZHJZLEPQ-UHFFFAOYSA-M 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 229940036248 turpentine Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/25—Sulfonic acids having sulfo groups bound to carbon atoms of rings other than six-membered aromatic rings of a carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US00155981A US3819689A (en) | 1971-06-23 | 1971-06-23 | Resolution of dl-camphor-10-sulfonic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL85292B1 true PL85292B1 (en, 2012) | 1976-04-30 |
Family
ID=22557571
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1972156202A PL85292B1 (en, 2012) | 1971-06-23 | 1972-06-22 |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US3819689A (en, 2012) |
| AT (1) | AT315159B (en, 2012) |
| AU (1) | AU460910B2 (en, 2012) |
| BE (1) | BE785228A (en, 2012) |
| CA (1) | CA966855A (en, 2012) |
| CS (1) | CS164924B2 (en, 2012) |
| DD (1) | DD100238A5 (en, 2012) |
| DE (1) | DE2230838A1 (en, 2012) |
| ES (1) | ES404120A1 (en, 2012) |
| FR (1) | FR2143425B1 (en, 2012) |
| GB (1) | GB1391664A (en, 2012) |
| HU (1) | HU165336B (en, 2012) |
| IE (1) | IE36408B1 (en, 2012) |
| IL (1) | IL39660A (en, 2012) |
| NL (1) | NL7208447A (en, 2012) |
| PL (1) | PL85292B1 (en, 2012) |
| SE (1) | SE372011B (en, 2012) |
| SU (1) | SU465778A3 (en, 2012) |
| ZA (1) | ZA723856B (en, 2012) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4370500A (en) * | 1978-11-06 | 1983-01-25 | American Cyanamid Company | Compound: d-N-(2-amino-2-phenethyl)-2-methoxyethylamine and process for preparing the same by selective crystallization |
| US4859771A (en) * | 1986-07-14 | 1989-08-22 | Merck & Co., Inc. | Process for resolution and racemization of amines with acidic α-hydrogens |
| CN105461596B (zh) * | 2015-12-18 | 2017-03-08 | 卢伯福 | 一种由樟脑磺酸铵转化成樟脑磺酸的清洁生产工艺 |
| CN105418467B (zh) * | 2015-12-18 | 2017-03-15 | 卢伯福 | 一种由樟脑磺酸钠转化成樟脑磺酸的清洁生产工艺 |
| CN106565550B (zh) * | 2016-11-02 | 2018-04-13 | 河北美邦工程科技股份有限公司 | 一种左旋苯甘氨酸生产过程中樟脑磺酸溶液的浓缩脱水方法 |
| DE102020213511A1 (de) | 2020-10-27 | 2022-04-28 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung eingetragener Verein | Verfahren zur enzymatischen Racemat-Spaltung von Campher |
-
1971
- 1971-06-23 US US00155981A patent/US3819689A/en not_active Expired - Lifetime
-
1972
- 1972-06-06 ZA ZA723856A patent/ZA723856B/xx unknown
- 1972-06-08 IE IE799/72A patent/IE36408B1/xx unknown
- 1972-06-09 IL IL39660A patent/IL39660A/xx unknown
- 1972-06-09 HU HUEI422A patent/HU165336B/hu unknown
- 1972-06-14 AU AU43414/72A patent/AU460910B2/en not_active Expired
- 1972-06-15 CS CS4199A patent/CS164924B2/cs unknown
- 1972-06-16 AT AT521472A patent/AT315159B/de not_active IP Right Cessation
- 1972-06-20 NL NL7208447A patent/NL7208447A/xx unknown
- 1972-06-20 SE SE7208137A patent/SE372011B/xx unknown
- 1972-06-22 CA CA145,407A patent/CA966855A/en not_active Expired
- 1972-06-22 ES ES404120A patent/ES404120A1/es not_active Expired
- 1972-06-22 DD DD163910A patent/DD100238A5/xx unknown
- 1972-06-22 PL PL1972156202A patent/PL85292B1/pl unknown
- 1972-06-22 SU SU1802042A patent/SU465778A3/ru active
- 1972-06-22 BE BE785228A patent/BE785228A/xx unknown
- 1972-06-22 GB GB2930772A patent/GB1391664A/en not_active Expired
- 1972-06-23 DE DE19722230838 patent/DE2230838A1/de active Pending
- 1972-06-23 FR FR7222882A patent/FR2143425B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| AU4341472A (en) | 1975-12-20 |
| AU460910B2 (en) | 1975-04-18 |
| IL39660A0 (en) | 1972-08-30 |
| IE36408L (en) | 1972-12-23 |
| BE785228A (fr) | 1972-12-22 |
| IL39660A (en) | 1975-02-10 |
| FR2143425B1 (en, 2012) | 1977-12-23 |
| NL7208447A (en, 2012) | 1972-12-28 |
| DD100238A5 (en, 2012) | 1973-09-12 |
| CS164924B2 (en, 2012) | 1975-11-28 |
| GB1391664A (en) | 1975-04-23 |
| DE2230838A1 (de) | 1972-12-28 |
| SE372011B (en, 2012) | 1974-12-09 |
| ZA723856B (en) | 1974-02-27 |
| CA966855A (en) | 1975-04-29 |
| ES404120A1 (es) | 1975-05-16 |
| AT315159B (de) | 1974-05-10 |
| IE36408B1 (en) | 1976-10-27 |
| FR2143425A1 (en, 2012) | 1973-02-02 |
| US3819689A (en) | 1974-06-25 |
| HU165336B (en, 2012) | 1974-08-28 |
| SU465778A3 (ru) | 1975-03-30 |
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