HU192247B - Process for separation of cyclopropan carbonic esthers from their secondary products - Google Patents
Process for separation of cyclopropan carbonic esthers from their secondary products Download PDFInfo
- Publication number
- HU192247B HU192247B HU833496A HU349683A HU192247B HU 192247 B HU192247 B HU 192247B HU 833496 A HU833496 A HU 833496A HU 349683 A HU349683 A HU 349683A HU 192247 B HU192247 B HU 192247B
- Authority
- HU
- Hungary
- Prior art keywords
- esters
- formula
- mixture
- general formula
- reaction
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 19
- 238000000926 separation method Methods 0.000 title abstract description 5
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 title 1
- 239000000203 mixture Substances 0.000 claims abstract description 30
- 150000002148 esters Chemical class 0.000 claims abstract description 27
- 150000001408 amides Chemical class 0.000 claims abstract description 16
- 150000001412 amines Chemical class 0.000 claims abstract description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 14
- 150000001875 compounds Chemical class 0.000 claims abstract description 13
- 238000004821 distillation Methods 0.000 claims abstract description 11
- 238000005406 washing Methods 0.000 claims abstract description 4
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical class OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000002904 solvent Substances 0.000 claims description 11
- 238000007112 amidation reaction Methods 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 2
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims 1
- FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical class OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 claims 1
- 239000000543 intermediate Substances 0.000 abstract description 5
- 239000004009 herbicide Substances 0.000 abstract 2
- 239000000047 product Substances 0.000 description 24
- 230000015572 biosynthetic process Effects 0.000 description 19
- 238000003786 synthesis reaction Methods 0.000 description 18
- 239000000463 material Substances 0.000 description 10
- 239000012071 phase Substances 0.000 description 10
- 239000006227 byproduct Substances 0.000 description 8
- 150000001993 dienes Chemical class 0.000 description 8
- 239000012535 impurity Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 6
- YYOLVILSZOVWLS-UHFFFAOYSA-N 1,1-dichloro-4-methylpenta-1,3-diene Chemical compound CC(C)=CC=C(Cl)Cl YYOLVILSZOVWLS-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- -1 permethric acid ester Chemical class 0.000 description 5
- 238000011084 recovery Methods 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- CHHVYWOANAOMKL-UHFFFAOYSA-N CC=CC=CC(Cl)Cl Chemical compound CC=CC=CC(Cl)Cl CHHVYWOANAOMKL-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000001476 alcoholic effect Effects 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
- LLMLSUSAKZVFOA-UHFFFAOYSA-N 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(O)=O LLMLSUSAKZVFOA-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
- 239000005749 Copper compound Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical class OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- BXEFQPCKQSTMKA-UHFFFAOYSA-N OC(=O)C=[N+]=[N-] Chemical compound OC(=O)C=[N+]=[N-] BXEFQPCKQSTMKA-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 238000010640 amide synthesis reaction Methods 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 150000001880 copper compounds Chemical class 0.000 description 1
- 238000012926 crystallographic analysis Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 125000005265 dialkylamine group Chemical group 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003344 environmental pollutant Substances 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 231100000719 pollutant Toxicity 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000002728 pyrethroid Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU833496A HU192247B (en) | 1983-10-10 | 1983-10-10 | Process for separation of cyclopropan carbonic esthers from their secondary products |
| FR8415398A FR2553088B1 (fr) | 1983-10-10 | 1984-10-08 | Procede de separation d'esters |
| JP59210603A JPS6055498B2 (ja) | 1983-10-10 | 1984-10-09 | エステルの分離方法 |
| DE19843437220 DE3437220A1 (de) | 1983-10-10 | 1984-10-10 | Verfahren zur trennung von estern |
| US06/659,320 US4521612A (en) | 1983-10-10 | 1984-10-10 | Process for the separation of esters |
| GB08425553A GB2148290B (en) | 1983-10-10 | 1984-10-10 | Process for the separation of other esters from cyclopropane carboxylic acid esters |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU833496A HU192247B (en) | 1983-10-10 | 1983-10-10 | Process for separation of cyclopropan carbonic esthers from their secondary products |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HUT36776A HUT36776A (en) | 1985-10-28 |
| HU192247B true HU192247B (en) | 1987-05-28 |
Family
ID=10964251
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU833496A HU192247B (en) | 1983-10-10 | 1983-10-10 | Process for separation of cyclopropan carbonic esthers from their secondary products |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4521612A (en, 2012) |
| JP (1) | JPS6055498B2 (en, 2012) |
| DE (1) | DE3437220A1 (en, 2012) |
| FR (1) | FR2553088B1 (en, 2012) |
| GB (1) | GB2148290B (en, 2012) |
| HU (1) | HU192247B (en, 2012) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4250326A (en) * | 1979-10-22 | 1981-02-10 | Fmc Corporation | Method of reducing the contents of haloethynyl-containing impurities in synthetic dihaloethenyl pyrethroid insecticides or intermediates by reaction with phosphites |
| US4288610A (en) * | 1980-02-25 | 1981-09-08 | Stauffer Chemical Company | Purification of pyrethroid intermediate compounds by selective partial saponification |
-
1983
- 1983-10-10 HU HU833496A patent/HU192247B/hu not_active IP Right Cessation
-
1984
- 1984-10-08 FR FR8415398A patent/FR2553088B1/fr not_active Expired
- 1984-10-09 JP JP59210603A patent/JPS6055498B2/ja not_active Expired
- 1984-10-10 US US06/659,320 patent/US4521612A/en not_active Expired - Lifetime
- 1984-10-10 DE DE19843437220 patent/DE3437220A1/de active Granted
- 1984-10-10 GB GB08425553A patent/GB2148290B/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2553088B1 (fr) | 1988-11-25 |
| JPS6097938A (ja) | 1985-05-31 |
| HUT36776A (en) | 1985-10-28 |
| FR2553088A1 (fr) | 1985-04-12 |
| GB2148290A (en) | 1985-05-30 |
| JPS6055498B2 (ja) | 1985-12-05 |
| GB8425553D0 (en) | 1984-11-14 |
| US4521612A (en) | 1985-06-04 |
| DE3437220C2 (en, 2012) | 1987-11-05 |
| DE3437220A1 (de) | 1985-04-25 |
| GB2148290B (en) | 1987-04-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 | ||
| HPC4 | Succession in title of patentee |
Owner name: AGRO-CHEMIE NOVENYVEDOESZER GYARTO, ERTEKESITOE ES |
|
| HMM4 | Cancellation of final prot. due to non-payment of fee |