JPS6125021B2 - - Google Patents
Info
- Publication number
- JPS6125021B2 JPS6125021B2 JP1560577A JP1560577A JPS6125021B2 JP S6125021 B2 JPS6125021 B2 JP S6125021B2 JP 1560577 A JP1560577 A JP 1560577A JP 1560577 A JP1560577 A JP 1560577A JP S6125021 B2 JPS6125021 B2 JP S6125021B2
- Authority
- JP
- Japan
- Prior art keywords
- ester
- benzoyl
- mother liquor
- weight
- aqueous phase
- 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
Links
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 41
- 150000002148 esters Chemical class 0.000 claims description 38
- 238000000034 method Methods 0.000 claims description 23
- 239000012452 mother liquor Substances 0.000 claims description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 18
- -1 chloropropionic acid ester Chemical class 0.000 claims description 18
- 239000000243 solution Substances 0.000 claims description 14
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 13
- 239000008346 aqueous phase Substances 0.000 claims description 12
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 9
- 230000032050 esterification Effects 0.000 claims description 9
- 238000005886 esterification reaction Methods 0.000 claims description 9
- 239000000047 product Substances 0.000 claims description 8
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical compound ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 7
- 229910052783 alkali metal Inorganic materials 0.000 claims description 7
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 claims description 7
- 229950011008 tetrachloroethylene Drugs 0.000 claims description 7
- 239000007864 aqueous solution Substances 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- 150000001340 alkali metals Chemical class 0.000 claims description 4
- 239000002585 base Substances 0.000 claims description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 4
- 239000011707 mineral Substances 0.000 claims description 4
- 150000001735 carboxylic acids Chemical class 0.000 claims description 3
- 150000002576 ketones Chemical class 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 150000002430 hydrocarbons Chemical class 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 150000008282 halocarbons Chemical class 0.000 claims 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
- 239000000203 mixture Substances 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 10
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 239000012046 mixed solvent Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 238000006480 benzoylation reaction Methods 0.000 description 4
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000005711 Benzoic acid Substances 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 235000010233 benzoic acid Nutrition 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- SUWRMAZHFSUJCB-UHFFFAOYSA-N 2-(3,4-dichloroanilino)propanoic acid Chemical compound OC(=O)C(C)NC1=CC=C(Cl)C(Cl)=C1 SUWRMAZHFSUJCB-UHFFFAOYSA-N 0.000 description 2
- WZZRJCUYSKKFHO-UHFFFAOYSA-N 2-(n-benzoyl-3,4-dichloroanilino)propanoic acid Chemical compound C=1C=C(Cl)C(Cl)=CC=1N(C(C)C(O)=O)C(=O)C1=CC=CC=C1 WZZRJCUYSKKFHO-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 238000010533 azeotropic distillation Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 2
- 229940116333 ethyl lactate Drugs 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 230000002363 herbicidal effect Effects 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 230000020477 pH reduction Effects 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 235000007320 Avena fatua Nutrition 0.000 description 1
- 244000075850 Avena orientalis Species 0.000 description 1
- SLCGUGMPSUYJAY-UHFFFAOYSA-N Benzoylprop-ethyl Chemical compound C=1C=C(Cl)C(Cl)=CC=1N(C(C)C(=O)OCC)C(=O)C1=CC=CC=C1 SLCGUGMPSUYJAY-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- UGQAHTKWBZSKFH-UHFFFAOYSA-N N-(3,4-dichlorophenyl)-N-ethylbenzamide Chemical compound C(C)N(C1=CC(=C(C=C1)Cl)Cl)C(C1=CC=CC=C1)=O UGQAHTKWBZSKFH-UHFFFAOYSA-N 0.000 description 1
- SIZGSFBMAHSXOL-UHFFFAOYSA-N N-butyl-N-(3,4-dichlorophenyl)benzamide Chemical compound C(CCC)N(C1=CC(=C(C=C1)Cl)Cl)C(C1=CC=CC=C1)=O SIZGSFBMAHSXOL-UHFFFAOYSA-N 0.000 description 1
- 235000005373 Uvularia sessilifolia Nutrition 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229940095102 methyl benzoate Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- JMMLZWNYIVVPOH-UHFFFAOYSA-N n-(3,4-dichlorophenyl)benzamide Chemical compound C1=C(Cl)C(Cl)=CC=C1NC(=O)C1=CC=CC=C1 JMMLZWNYIVVPOH-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- FRENCPHEVDKGOL-UHFFFAOYSA-N propan-2-yl 2-benzamido-2-(3-chloro-4-fluorophenyl)propanoate Chemical compound C=1C=C(F)C(Cl)=CC=1C(C)(C(=O)OC(C)C)NC(=O)C1=CC=CC=C1 FRENCPHEVDKGOL-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/12—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB660776A GB1571804A (en) | 1976-02-19 | 1976-02-19 | Recovery of esters derived from n-benzoyl-n-2-aminopropionic acids |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS52100436A JPS52100436A (en) | 1977-08-23 |
| JPS6125021B2 true JPS6125021B2 (enrdf_load_stackoverflow) | 1986-06-13 |
Family
ID=9817556
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1560577A Granted JPS52100436A (en) | 1976-02-19 | 1977-02-17 | Recovering method of herbicidal ester |
Country Status (11)
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1164160A (en) * | 1966-12-30 | 1969-09-17 | Shell Int Research | N,N-Disubstituted Amino Acid Derivatives and their use as Herbicides |
| GB1289283A (enrdf_load_stackoverflow) * | 1970-03-04 | 1972-09-13 |
-
1976
- 1976-02-19 GB GB660776A patent/GB1571804A/en not_active Expired
-
1977
- 1977-02-01 CA CA270,792A patent/CA1106392A/en not_active Expired
- 1977-02-16 BE BE1007950A patent/BE851460A/xx not_active IP Right Cessation
- 1977-02-17 DE DE19772706823 patent/DE2706823A1/de active Granted
- 1977-02-17 SU SU772453151A patent/SU644376A3/ru active
- 1977-02-17 FR FR7704543A patent/FR2341561A1/fr active Granted
- 1977-02-17 NL NL7701670A patent/NL7701670A/xx not_active Application Discontinuation
- 1977-02-17 IT IT2040777A patent/IT1074674B/it active
- 1977-02-17 CH CH199077A patent/CH632235A5/de not_active IP Right Cessation
- 1977-02-17 BG BG035440A patent/BG27892A3/xx unknown
- 1977-02-17 JP JP1560577A patent/JPS52100436A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DE2706823A1 (de) | 1977-09-01 |
| CH632235A5 (en) | 1982-09-30 |
| FR2341561A1 (fr) | 1977-09-16 |
| SU644376A3 (ru) | 1979-01-25 |
| BE851460A (nl) | 1977-08-16 |
| JPS52100436A (en) | 1977-08-23 |
| CA1106392A (en) | 1981-08-04 |
| NL7701670A (nl) | 1977-08-23 |
| DE2706823C2 (enrdf_load_stackoverflow) | 1989-01-05 |
| BG27892A3 (en) | 1980-01-15 |
| FR2341561B1 (enrdf_load_stackoverflow) | 1980-10-10 |
| IT1074674B (it) | 1985-04-20 |
| GB1571804A (en) | 1980-07-16 |
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