GB1571804A - Recovery of esters derived from n-benzoyl-n-2-aminopropionic acids - Google Patents
Recovery of esters derived from n-benzoyl-n-2-aminopropionic acids Download PDFInfo
- Publication number
- GB1571804A GB1571804A GB660776A GB660776A GB1571804A GB 1571804 A GB1571804 A GB 1571804A GB 660776 A GB660776 A GB 660776A GB 660776 A GB660776 A GB 660776A GB 1571804 A GB1571804 A GB 1571804A
- Authority
- GB
- United Kingdom
- Prior art keywords
- ester
- benzoyl
- residue
- aqueous
- acid
- 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
- 150000002148 esters Chemical class 0.000 title claims abstract description 63
- 239000002253 acid Substances 0.000 title claims abstract description 21
- 238000011084 recovery Methods 0.000 title claims description 7
- 150000007513 acids Chemical class 0.000 title description 9
- -1 alkali metal salt Chemical class 0.000 claims abstract description 20
- 239000012452 mother liquor Substances 0.000 claims abstract description 20
- 239000008346 aqueous phase Substances 0.000 claims abstract description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 13
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 11
- 230000032050 esterification Effects 0.000 claims abstract description 11
- 238000005886 esterification reaction Methods 0.000 claims abstract description 11
- 239000003960 organic solvent Substances 0.000 claims abstract description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 7
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 6
- 238000006480 benzoylation reaction Methods 0.000 claims abstract description 5
- 229910052500 inorganic mineral Inorganic materials 0.000 claims abstract description 5
- 239000011707 mineral Substances 0.000 claims abstract description 5
- 239000003377 acid catalyst Substances 0.000 claims abstract description 4
- 230000020477 pH reduction Effects 0.000 claims abstract description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 3
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 3
- 239000011737 fluorine Substances 0.000 claims abstract description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 56
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 39
- 239000000203 mixture Substances 0.000 claims description 35
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 26
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 16
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 15
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 15
- 239000000243 solution Substances 0.000 claims description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 claims description 12
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 12
- 229950011008 tetrachloroethylene Drugs 0.000 claims description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 9
- 239000000047 product Substances 0.000 claims description 9
- 239000001117 sulphuric acid Substances 0.000 claims description 9
- 235000011149 sulphuric acid Nutrition 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 8
- 238000002425 crystallisation Methods 0.000 claims description 7
- 230000008025 crystallization Effects 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- 239000002585 base Substances 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 6
- 238000004821 distillation Methods 0.000 claims description 6
- 238000010992 reflux Methods 0.000 claims description 6
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 6
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 6
- 239000007858 starting material Substances 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 239000012074 organic phase Substances 0.000 claims description 5
- 150000001340 alkali metals Chemical class 0.000 claims description 4
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims description 4
- 235000010755 mineral Nutrition 0.000 claims description 4
- IKVXBIIHQGXQRQ-UHFFFAOYSA-N propan-2-yl 2-(n-benzoyl-3-chloro-4-fluoroanilino)propanoate Chemical compound C=1C=C(F)C(Cl)=CC=1N(C(C)C(=O)OC(C)C)C(=O)C1=CC=CC=C1 IKVXBIIHQGXQRQ-UHFFFAOYSA-N 0.000 claims description 4
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 238000000605 extraction Methods 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- 150000002430 hydrocarbons Chemical class 0.000 claims description 3
- 150000002576 ketones Chemical class 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 230000035484 reaction time Effects 0.000 claims description 3
- 238000003786 synthesis reaction Methods 0.000 claims description 3
- FEXQDZTYJVXMOS-UHFFFAOYSA-N Isopropyl benzoate Chemical compound CC(C)OC(=O)C1=CC=CC=C1 FEXQDZTYJVXMOS-UHFFFAOYSA-N 0.000 claims description 2
- 239000012043 crude product Substances 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- RBNIGDFIUWJJEV-UHFFFAOYSA-N methyl 2-(n-benzoyl-3-chloro-4-fluoroanilino)propanoate Chemical compound C=1C=C(F)C(Cl)=CC=1N(C(C)C(=O)OC)C(=O)C1=CC=CC=C1 RBNIGDFIUWJJEV-UHFFFAOYSA-N 0.000 claims description 2
- 229940095102 methyl benzoate Drugs 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 238000001953 recrystallisation Methods 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- 238000010626 work up procedure Methods 0.000 claims description 2
- 150000008282 halocarbons Chemical class 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 10
- 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 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- LZCLXQDLBQLTDK-UHFFFAOYSA-N lactic acid ethyl ester Natural products CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 4
- 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 3
- 239000005711 Benzoic acid Substances 0.000 description 3
- 235000010233 benzoic acid Nutrition 0.000 description 3
- 229940116333 ethyl lactate Drugs 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
- 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
- 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 2
- 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 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 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 2
- 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 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 230000002363 herbicidal effect Effects 0.000 description 2
- 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 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N o-aminobenzenecarboxylic acid Natural products NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- IBUQLJLHWNSERX-UHFFFAOYSA-N 2-amino-2-(3,4-dichlorophenyl)propanoic acid Chemical compound OC(=O)C(N)(C)C1=CC=C(Cl)C(Cl)=C1 IBUQLJLHWNSERX-UHFFFAOYSA-N 0.000 description 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
- 235000007320 Avena fatua Nutrition 0.000 description 1
- 244000075850 Avena orientalis Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- QNAYBMKLOCPYGJ-UHFFFAOYSA-N D-alpha-Ala Natural products CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 description 1
- 235000005373 Uvularia sessilifolia Nutrition 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011877 solvent mixture 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
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)
Priority Applications (11)
| 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 |
| CA270,792A CA1106392A (en) | 1976-02-19 | 1977-02-01 | Recovery of herbicidal esters |
| BE1007950A BE851460A (nl) | 1976-02-19 | 1977-02-16 | Werkwijze voor het winnen van esters met herbicide eigenschappen |
| BG035440A BG27892A3 (en) | 1976-02-19 | 1977-02-17 | Method of extracting esters of n-benzoil-n-(3,4-dihalophenyl) -2-aminoropionic acid |
| IT2040777A IT1074674B (it) | 1976-02-19 | 1977-02-17 | Processo per il recupero di esteri ad attivita' erbicida |
| DE19772706823 DE2706823A1 (de) | 1976-02-19 | 1977-02-17 | Verfahren zur reingewinnung von estern mit herbizidwirkung |
| NL7701670A NL7701670A (nl) | 1976-02-19 | 1977-02-17 | Werkwijze voor het winnen van esters met herbicide eigenschappen. |
| SU772453151A SU644376A3 (ru) | 1976-02-19 | 1977-02-17 | Способ выделени эфиров бензоил- - (3,4-дигалоидфенил)2-аминопропионовых кислот |
| JP1560577A JPS52100436A (en) | 1976-02-19 | 1977-02-17 | Recovering method of herbicidal ester |
| CH199077A CH632235A5 (en) | 1976-02-19 | 1977-02-17 | Process for the preparation of esters having a herbicidal action |
| FR7704543A FR2341561A1 (fr) | 1976-02-19 | 1977-02-17 | Recuperation d'esters d'acides n-benzoyl-n-(3,4-dihalogenophenyl)-2-aminopropioniques et applications herbicides |
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 (1)
| Publication Number | Publication Date |
|---|---|
| GB1571804A true GB1571804A (en) | 1980-07-16 |
Family
ID=9817556
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB660776A Expired GB1571804A (en) | 1976-02-19 | 1976-02-19 | Recovery of esters derived from n-benzoyl-n-2-aminopropionic acids |
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 CH CH199077A patent/CH632235A5/de not_active IP Right Cessation
- 1977-02-17 DE DE19772706823 patent/DE2706823A1/de active Granted
- 1977-02-17 NL NL7701670A patent/NL7701670A/xx not_active Application Discontinuation
- 1977-02-17 BG BG035440A patent/BG27892A3/xx unknown
- 1977-02-17 IT IT2040777A patent/IT1074674B/it active
- 1977-02-17 JP JP1560577A patent/JPS52100436A/ja active Granted
- 1977-02-17 SU SU772453151A patent/SU644376A3/ru active
- 1977-02-17 FR FR7704543A patent/FR2341561A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| BE851460A (nl) | 1977-08-16 |
| CA1106392A (en) | 1981-08-04 |
| BG27892A3 (en) | 1980-01-15 |
| IT1074674B (it) | 1985-04-20 |
| DE2706823C2 (enrdf_load_stackoverflow) | 1989-01-05 |
| JPS52100436A (en) | 1977-08-23 |
| DE2706823A1 (de) | 1977-09-01 |
| FR2341561A1 (fr) | 1977-09-16 |
| CH632235A5 (en) | 1982-09-30 |
| FR2341561B1 (enrdf_load_stackoverflow) | 1980-10-10 |
| JPS6125021B2 (enrdf_load_stackoverflow) | 1986-06-13 |
| NL7701670A (nl) | 1977-08-23 |
| SU644376A3 (ru) | 1979-01-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1077057A (en) | Process for the preparation of acetic acid derivatives | |
| EP0208948B1 (en) | A method for optical resolution of phenylacetic acid derivative | |
| US4673761A (en) | Process for preparing anti-inflammatory cycloalkylidenemethylphenylacetic acid derivatives | |
| GB1571804A (en) | Recovery of esters derived from n-benzoyl-n-2-aminopropionic acids | |
| KR870000981B1 (ko) | α-할로알킬아미드의 제조방법 | |
| EP0155779A1 (en) | A method for the optical purification of an optically active 2,2-dimethylcyclopropanecarboxylic acid amide | |
| EP0093511B1 (en) | Method for producing and optically active 2,2-dimethylcyclopropanecarboxylic acid | |
| JPH0149253B2 (enrdf_load_stackoverflow) | ||
| CN116917263A (zh) | 顺式2-链烯酸的制备 | |
| US4337355A (en) | Process for preparing 4-hydroxyphenylacetic acid | |
| JPH09188649A (ja) | 共沸エステル化による合成ピレトロイドの製造方法 | |
| US6087499A (en) | Process for producing 5-perfluoroalkyluracil derivatives | |
| US5654338A (en) | Preparation of optically active α-(hydroxyphenoxy)alkanecarboxylic acids and derivatives thereof | |
| JP4397990B2 (ja) | ３−アルキルフラバノノール誘導体の精製法 | |
| JPH0134979B2 (enrdf_load_stackoverflow) | ||
| RU2015953C1 (ru) | Способ расщепления рацемата 2,2-диметилциклопропанкарбоновой кислоты | |
| Kozłowski et al. | Lower Aliphatic 2-oxoacids and their Eteyl Esters from Ethyl Esters of 2-Hydroxy Acids | |
| JP2549173B2 (ja) | 光学活性のｄー２ー（４ーヒドロキシフェノキシ）プロピオン酸エステルの製造方法 | |
| JPH06166683A (ja) | Ｏ，ｏ´−ジアシル酒石酸無水物の製造法 | |
| EP0101570B1 (en) | Method for the resolution of racemic 2-cp-difluoromethoxy phenyl)-3-methylbutyric acid | |
| JPH0565500B2 (enrdf_load_stackoverflow) | ||
| JPH027305B2 (enrdf_load_stackoverflow) | ||
| JPH072690B2 (ja) | ３−メチル−４−ニトロフエノ−ルの製造方法 | |
| JPH07238061A (ja) | 芳香族メトキシカルボン酸メチルエステルの製造方法 | |
| JP2941097B2 (ja) | ジヒドロキシフェニル−２−ヒドロキシ酢酸の製造方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 19950217 |