SE502756C2 - Förfarande för rening av mandelsyra-N,N-dietylamid - Google Patents
Förfarande för rening av mandelsyra-N,N-dietylamidInfo
- Publication number
- SE502756C2 SE502756C2 SE9000421A SE9000421A SE502756C2 SE 502756 C2 SE502756 C2 SE 502756C2 SE 9000421 A SE9000421 A SE 9000421A SE 9000421 A SE9000421 A SE 9000421A SE 502756 C2 SE502756 C2 SE 502756C2
- Authority
- SE
- Sweden
- Prior art keywords
- dem
- adduct
- process according
- water
- cacl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 13
- 238000000746 purification Methods 0.000 title claims abstract 4
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 title abstract 2
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 title abstract 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 title abstract 2
- 229960002510 mandelic acid Drugs 0.000 title abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000011575 calcium Substances 0.000 claims abstract description 5
- 229910052791 calcium Inorganic materials 0.000 claims abstract description 3
- -1 calcium halide Chemical class 0.000 claims abstract description 3
- 239000002904 solvent Substances 0.000 claims description 13
- 238000003756 stirring Methods 0.000 claims description 9
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 claims description 8
- 229910001628 calcium chloride Inorganic materials 0.000 claims description 8
- 239000001110 calcium chloride Substances 0.000 claims description 8
- 239000000243 solution Substances 0.000 claims description 8
- 238000002425 crystallisation Methods 0.000 claims description 6
- 230000008025 crystallization Effects 0.000 claims description 6
- 230000002209 hydrophobic effect Effects 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 150000001805 chlorine compounds Chemical group 0.000 claims 2
- 150000004820 halides Chemical class 0.000 claims 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 1
- WZHCOOQXZCIUNC-UHFFFAOYSA-N cyclandelate Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C(O)C1=CC=CC=C1 WZHCOOQXZCIUNC-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000013078 crystal Substances 0.000 description 8
- 235000011148 calcium chloride Nutrition 0.000 description 7
- XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 229910014811 CaCl2—6H2O Inorganic materials 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- LXTKCTMGEWVPTB-UHFFFAOYSA-N butylazanium;acetate Chemical compound CC(O)=O.CCCCN LXTKCTMGEWVPTB-UHFFFAOYSA-N 0.000 description 1
- 229910001622 calcium bromide Inorganic materials 0.000 description 1
- WGEFECGEFUFIQW-UHFFFAOYSA-L calcium dibromide Chemical compound [Ca+2].[Br-].[Br-] WGEFECGEFUFIQW-UHFFFAOYSA-L 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 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
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 description 1
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 description 1
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/22—Separation; Purification; Stabilisation; Use of additives
- C07C231/24—Separation; Purification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/32—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
- C07C235/34—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE9000421A SE502756C2 (sv) | 1990-02-06 | 1990-02-06 | Förfarande för rening av mandelsyra-N,N-dietylamid |
| US07/649,401 US5149873A (en) | 1990-02-06 | 1991-02-01 | Process for the purification of mandelic acid N,N-diethylamide |
| AT91850021T ATE116965T1 (de) | 1990-02-06 | 1991-02-04 | Reinigungsprozess für n,n-diethylmandelsäureamid. |
| ES91850021T ES2066413T3 (es) | 1990-02-06 | 1991-02-04 | Procedimiento para la purificacion de n,n-dietilmandelamida. |
| DE69106538T DE69106538T2 (de) | 1990-02-06 | 1991-02-04 | Reinigungsprozess für N,N-Diethylmandelsäureamid. |
| DK91850021.6T DK0441760T3 (da) | 1990-02-06 | 1991-02-04 | Fremgangsmåde til rensning af N,N-dimethylmandelsyreamid |
| EP91850021A EP0441760B1 (de) | 1990-02-06 | 1991-02-04 | Reinigungsprozess für N,N-Diethylmandelsäureamid |
| JP3035347A JPH072749A (ja) | 1990-02-06 | 1991-02-05 | マンデル酸ｎ，ｎ−ジエチルアミドの精製法 |
| GR950400263T GR3015020T3 (en) | 1990-02-06 | 1995-02-08 | Purification process for N,N-diethylmandelamide. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE9000421A SE502756C2 (sv) | 1990-02-06 | 1990-02-06 | Förfarande för rening av mandelsyra-N,N-dietylamid |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| SE9000421D0 SE9000421D0 (sv) | 1990-02-06 |
| SE9000421L SE9000421L (sv) | 1991-08-07 |
| SE502756C2 true SE502756C2 (sv) | 1996-01-08 |
Family
ID=20378469
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE9000421A SE502756C2 (sv) | 1990-02-06 | 1990-02-06 | Förfarande för rening av mandelsyra-N,N-dietylamid |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US5149873A (de) |
| EP (1) | EP0441760B1 (de) |
| JP (1) | JPH072749A (de) |
| AT (1) | ATE116965T1 (de) |
| DE (1) | DE69106538T2 (de) |
| DK (1) | DK0441760T3 (de) |
| ES (1) | ES2066413T3 (de) |
| GR (1) | GR3015020T3 (de) |
| SE (1) | SE502756C2 (de) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109678750A (zh) * | 2018-12-29 | 2019-04-26 | 上海天慈国际药业有限公司 | 一种n,n-二乙基-2-羟基-2-苯乙酰胺的制备方法 |
| EP4296262A1 (de) | 2019-07-12 | 2023-12-27 | Alzchem Trostberg GmbH | Verfahren zur herstellung einer metastabilen kristallmodifikation von n-(aminoiminomethyl)-2-aminoethansäure (iv) |
| CN111662205B (zh) * | 2020-06-22 | 2025-07-18 | 北京斯瑞朗文生物科技有限公司 | N,n-二乙基-2-羟基-2-苯乙酰胺的晶型及其制备方法和应用 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3876800A (en) * | 1969-05-12 | 1975-04-08 | Clin Midy | Pharmaceutical compositions and methods for treating inflammation and pain |
| US4192892A (en) * | 1976-04-06 | 1980-03-11 | Elisabeth Malm | Aromatic α-hydroxyamides with insect repellant properties |
| SE409808B (sv) * | 1976-04-06 | 1979-09-10 | Thorsell Walborg Susanna | Anvendning av vid kveveatomen disubstituerade mandelsyraamider sasom insektsavvisande medel |
-
1990
- 1990-02-06 SE SE9000421A patent/SE502756C2/sv not_active IP Right Cessation
-
1991
- 1991-02-01 US US07/649,401 patent/US5149873A/en not_active Expired - Fee Related
- 1991-02-04 DK DK91850021.6T patent/DK0441760T3/da active
- 1991-02-04 EP EP91850021A patent/EP0441760B1/de not_active Expired - Lifetime
- 1991-02-04 ES ES91850021T patent/ES2066413T3/es not_active Expired - Lifetime
- 1991-02-04 DE DE69106538T patent/DE69106538T2/de not_active Expired - Fee Related
- 1991-02-04 AT AT91850021T patent/ATE116965T1/de not_active IP Right Cessation
- 1991-02-05 JP JP3035347A patent/JPH072749A/ja active Pending
-
1995
- 1995-02-08 GR GR950400263T patent/GR3015020T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES2066413T3 (es) | 1995-03-01 |
| JPH072749A (ja) | 1995-01-06 |
| DE69106538D1 (de) | 1995-02-23 |
| EP0441760A1 (de) | 1991-08-14 |
| DE69106538T2 (de) | 1995-05-18 |
| DK0441760T3 (da) | 1995-06-12 |
| US5149873A (en) | 1992-09-22 |
| SE9000421L (sv) | 1991-08-07 |
| GR3015020T3 (en) | 1995-05-31 |
| ATE116965T1 (de) | 1995-01-15 |
| SE9000421D0 (sv) | 1990-02-06 |
| EP0441760B1 (de) | 1995-01-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| NUG | Patent has lapsed |
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