CA1106392A - Recovery of herbicidal esters - Google Patents
Recovery of herbicidal estersInfo
- Publication number
- CA1106392A CA1106392A CA270,792A CA270792A CA1106392A CA 1106392 A CA1106392 A CA 1106392A CA 270792 A CA270792 A CA 270792A CA 1106392 A CA1106392 A CA 1106392A
- Authority
- CA
- Canada
- Prior art keywords
- process according
- ester
- aqueous phase
- acid
- aqueous
- 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
- 238000011084 recovery Methods 0.000 title claims abstract description 6
- 150000002148 esters Chemical class 0.000 title claims description 39
- 230000002363 herbicidal effect Effects 0.000 title description 3
- 238000000034 method Methods 0.000 claims abstract description 24
- 239000002253 acid Substances 0.000 claims abstract description 19
- 239000008346 aqueous phase Substances 0.000 claims abstract description 14
- 239000003960 organic solvent Substances 0.000 claims abstract description 7
- 229910052500 inorganic mineral Inorganic materials 0.000 claims abstract description 6
- 239000011707 mineral Substances 0.000 claims abstract description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 37
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 18
- -1 alkali metal salt Chemical class 0.000 claims description 13
- 239000012452 mother liquor Substances 0.000 claims description 10
- 229910052783 alkali metal Inorganic materials 0.000 claims description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 7
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 claims description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 7
- 239000001117 sulphuric acid Substances 0.000 claims description 7
- 235000011149 sulphuric acid Nutrition 0.000 claims description 7
- 229950011008 tetrachloroethylene Drugs 0.000 claims description 7
- 150000007513 acids Chemical class 0.000 claims description 6
- 238000002425 crystallisation Methods 0.000 claims description 6
- 230000008025 crystallization Effects 0.000 claims description 6
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 claims description 5
- 230000032050 esterification Effects 0.000 claims description 5
- 238000005886 esterification reaction Methods 0.000 claims description 5
- 239000002585 base Substances 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 239000003377 acid catalyst Substances 0.000 claims description 2
- 125000000217 alkyl group Chemical group 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
- 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
- 150000002576 ketones Chemical class 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 150000008282 halocarbons Chemical class 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 26
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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 7
- 239000000047 product Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 6
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 6
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 6
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 6
- 239000002904 solvent Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000006480 benzoylation reaction Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000007858 starting material 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
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- 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 2
- 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 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- 229940116333 ethyl lactate Drugs 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 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
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- QNAYBMKLOCPYGJ-UHFFFAOYSA-M alaninate Chemical compound CC(N)C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-M 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- KTYVHLCLTPLSGC-UHFFFAOYSA-N amino propanoate Chemical compound CCC(=O)ON KTYVHLCLTPLSGC-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- TUFYEVMTXRPQQK-UHFFFAOYSA-N ethyl 2-(3,4-dichloroanilino)propanoate Chemical compound CCOC(=O)C(C)NC1=CC=C(Cl)C(Cl)=C1 TUFYEVMTXRPQQK-UHFFFAOYSA-N 0.000 description 1
- NHWFXKLJVWHVKH-UHFFFAOYSA-N ethyl 3-(n-benzoyl-3,4-dichloroanilino)propanoate Chemical compound C=1C=C(Cl)C(Cl)=CC=1N(CCC(=O)OCC)C(=O)C1=CC=CC=C1 NHWFXKLJVWHVKH-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000000463 material Substances 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
- WSGCRAOTEDLMFQ-UHFFFAOYSA-N nonan-5-one Chemical compound CCCCC(=O)CCCC WSGCRAOTEDLMFQ-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 150000003151 propanoic acid esters Chemical class 0.000 description 1
- 230000036647 reaction Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB6607/76 | 1976-02-19 | ||
| GB660776A GB1571804A (en) | 1976-02-19 | 1976-02-19 | Recovery of esters derived from n-benzoyl-n-2-aminopropionic acids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1106392A true CA1106392A (en) | 1981-08-04 |
Family
ID=9817556
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA270,792A Expired CA1106392A (en) | 1976-02-19 | 1977-02-01 | Recovery of herbicidal esters |
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 FR FR7704543A patent/FR2341561A1/fr active Granted
- 1977-02-17 IT IT2040777A patent/IT1074674B/it active
- 1977-02-17 NL NL7701670A patent/NL7701670A/xx not_active Application Discontinuation
- 1977-02-17 BG BG035440A patent/BG27892A3/xx unknown
- 1977-02-17 JP JP1560577A patent/JPS52100436A/ja active Granted
- 1977-02-17 DE DE19772706823 patent/DE2706823A1/de active Granted
- 1977-02-17 SU SU772453151A patent/SU644376A3/ru active
- 1977-02-17 CH CH199077A patent/CH632235A5/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| GB1571804A (en) | 1980-07-16 |
| BG27892A3 (en) | 1980-01-15 |
| NL7701670A (nl) | 1977-08-23 |
| DE2706823A1 (de) | 1977-09-01 |
| BE851460A (nl) | 1977-08-16 |
| JPS6125021B2 (enrdf_load_stackoverflow) | 1986-06-13 |
| IT1074674B (it) | 1985-04-20 |
| DE2706823C2 (enrdf_load_stackoverflow) | 1989-01-05 |
| SU644376A3 (ru) | 1979-01-25 |
| FR2341561A1 (fr) | 1977-09-16 |
| CH632235A5 (en) | 1982-09-30 |
| JPS52100436A (en) | 1977-08-23 |
| FR2341561B1 (enrdf_load_stackoverflow) | 1980-10-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |