CA1162571A - Process for preparing high assay dicamba - Google Patents
Process for preparing high assay dicambaInfo
- Publication number
- CA1162571A CA1162571A CA000376929A CA376929A CA1162571A CA 1162571 A CA1162571 A CA 1162571A CA 000376929 A CA000376929 A CA 000376929A CA 376929 A CA376929 A CA 376929A CA 1162571 A CA1162571 A CA 1162571A
- Authority
- CA
- Canada
- Prior art keywords
- acid
- methoxy
- percent
- weight
- mixture
- 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
- IWEDIXLBFLAXBO-UHFFFAOYSA-N dicamba Chemical compound COC1=C(Cl)C=CC(Cl)=C1C(O)=O IWEDIXLBFLAXBO-UHFFFAOYSA-N 0.000 title claims abstract description 33
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 5
- 239000005504 Dicamba Substances 0.000 title description 12
- 238000003556 assay Methods 0.000 title description 3
- 239000000203 mixture Substances 0.000 claims abstract description 21
- 230000032050 esterification Effects 0.000 claims abstract description 8
- 238000005886 esterification reaction Methods 0.000 claims abstract description 8
- 238000000034 method Methods 0.000 claims description 25
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 21
- 239000011541 reaction mixture Substances 0.000 claims description 11
- 238000010992 reflux Methods 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- AUVSCSCAPKFMEK-UHFFFAOYSA-N 3,5-dichloro-2-methoxybenzoic acid Chemical compound COC1=C(Cl)C=C(Cl)C=C1C(O)=O AUVSCSCAPKFMEK-UHFFFAOYSA-N 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 9
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 6
- 239000003377 acid catalyst Substances 0.000 claims description 5
- 239000012429 reaction media Substances 0.000 claims description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 4
- 150000004996 alkyl benzenes Chemical class 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 239000012430 organic reaction media Substances 0.000 claims description 3
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- 238000010533 azeotropic distillation Methods 0.000 claims description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims description 2
- 229940092714 benzenesulfonic acid Drugs 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims description 2
- HKJYVRJHDIPMQB-UHFFFAOYSA-N propan-1-olate;titanium(4+) Chemical compound CCCO[Ti](OCCC)(OCCC)OCCC HKJYVRJHDIPMQB-UHFFFAOYSA-N 0.000 claims description 2
- 125000005489 p-toluenesulfonic acid group Chemical group 0.000 claims 1
- 239000002253 acid Substances 0.000 abstract description 3
- 239000000047 product Substances 0.000 description 10
- 239000002244 precipitate Substances 0.000 description 9
- 239000008096 xylene Substances 0.000 description 8
- 238000001914 filtration Methods 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 3
- RANCECPPZPIPNO-UHFFFAOYSA-N 2,5-dichlorophenol Chemical compound OC1=CC(Cl)=CC=C1Cl RANCECPPZPIPNO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- -1 alkane ester Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
- QVTQYSFCFOGITD-UHFFFAOYSA-N 2,5-dichlorobenzoic acid Chemical compound OC(=O)C1=CC(Cl)=CC=C1Cl QVTQYSFCFOGITD-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 229960004592 isopropanol Drugs 0.000 description 2
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- 150000003738 xylenes Chemical class 0.000 description 2
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- UMPSXRYVXUPCOS-UHFFFAOYSA-N 2,3-dichlorophenol Chemical class OC1=CC=CC(Cl)=C1Cl UMPSXRYVXUPCOS-UHFFFAOYSA-N 0.000 description 1
- HFZWRUODUSTPEG-UHFFFAOYSA-N 2,4-dichlorophenol Chemical compound OC1=CC=C(Cl)C=C1Cl HFZWRUODUSTPEG-UHFFFAOYSA-N 0.000 description 1
- FKIKPQHMWFZFEB-UHFFFAOYSA-N 3,6-dichloro-2-hydroxybenzoic acid Chemical compound OC(=O)C1=C(O)C(Cl)=CC=C1Cl FKIKPQHMWFZFEB-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 150000001559 benzoic acids Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 230000002301 combined effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/487—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification
- C07C51/493—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification whereby carboxylic acid esters are formed
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C62/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C62/02—Saturated compounds containing hydroxy or O-metal groups
- C07C62/04—Saturated compounds containing hydroxy or O-metal groups with a six-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C63/00—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
- C07C63/04—Monocyclic monocarboxylic acids
- C07C63/06—Benzoic acid
- C07C63/10—Halides thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US15819680A | 1980-06-11 | 1980-06-11 | |
| US158,196 | 1980-06-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1162571A true CA1162571A (en) | 1984-02-21 |
Family
ID=22567061
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000376929A Expired CA1162571A (en) | 1980-06-11 | 1981-05-06 | Process for preparing high assay dicamba |
Country Status (17)
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61197365U (enrdf_load_stackoverflow) * | 1985-05-31 | 1986-12-09 | ||
| BR112022019528A2 (pt) * | 2020-03-31 | 2022-11-16 | Basf Corp | Formulações aquosas agroquímicas, processo para fazer formulações, uso de formulações e método de controle de vegetação indesejada |
| USD967679S1 (en) * | 2021-07-24 | 2022-10-25 | Li Peng | Lawn coring aerator |
| USD1012640S1 (en) * | 2023-07-26 | 2024-01-30 | Shenzhenshi Wanlian Technology Innovation Co., Ltd. | Lawn aerator |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3013054A (en) * | 1958-08-04 | 1961-12-12 | Velsicol Chemical Corp | 2-methoxy-3, 6-dichlorobenzoates |
| US3012870A (en) * | 1958-08-04 | 1961-12-12 | Velsicol Chemical Corp | Method of destroying undesirable vegetation |
| GB1282926A (en) * | 1968-10-10 | 1972-07-26 | El Paso Products Co | Esterification and extraction process |
| US4094913A (en) * | 1977-01-07 | 1978-06-13 | Velsicol Chemical Corporation | Process for the preparation of 2,5-dichlorophenol |
| US4215065A (en) * | 1979-01-02 | 1980-07-29 | Monsanto Company | Acid separation |
-
1981
- 1981-05-06 CA CA000376929A patent/CA1162571A/en not_active Expired
- 1981-05-08 CH CH301581A patent/CH646936A5/de not_active IP Right Cessation
- 1981-05-13 IL IL62860A patent/IL62860A/xx unknown
- 1981-05-19 AU AU70814/81A patent/AU538334B2/en not_active Ceased
- 1981-05-19 KR KR1019810001725A patent/KR850001156B1/ko not_active Expired
- 1981-05-21 NL NL8102501A patent/NL8102501A/nl not_active Application Discontinuation
- 1981-05-22 FR FR8110283A patent/FR2484405B1/fr not_active Expired
- 1981-05-27 JP JP8066581A patent/JPS5728028A/ja active Granted
- 1981-06-01 IT IT48596/81A patent/IT1142534B/it active
- 1981-06-03 ZA ZA00813711A patent/ZA813711B/xx unknown
- 1981-06-03 DE DE19813122073 patent/DE3122073A1/de active Granted
- 1981-06-10 SE SE8103635A patent/SE442196B/sv not_active IP Right Cessation
- 1981-06-10 BE BE0/205058A patent/BE889169A/fr not_active IP Right Cessation
- 1981-06-10 BR BR8103658A patent/BR8103658A/pt not_active IP Right Cessation
- 1981-06-10 ES ES502917A patent/ES502917A0/es active Granted
- 1981-06-10 GB GB8117725A patent/GB2077729B/en not_active Expired
- 1981-06-10 AT AT0258381A patent/AT374782B/de active
Also Published As
| Publication number | Publication date |
|---|---|
| DE3122073A1 (de) | 1982-03-18 |
| AT374782B (de) | 1984-05-25 |
| JPH0114896B2 (enrdf_load_stackoverflow) | 1989-03-14 |
| FR2484405B1 (fr) | 1985-07-05 |
| JPS5728028A (en) | 1982-02-15 |
| IT1142534B (it) | 1986-10-08 |
| AU538334B2 (en) | 1984-08-09 |
| SE442196B (sv) | 1985-12-09 |
| IL62860A0 (en) | 1981-07-31 |
| GB2077729B (en) | 1984-03-14 |
| IL62860A (en) | 1984-09-30 |
| KR830006159A (ko) | 1983-09-17 |
| ZA813711B (en) | 1982-06-30 |
| BR8103658A (pt) | 1982-03-02 |
| ATA258381A (de) | 1983-10-15 |
| ES8203818A1 (es) | 1982-04-01 |
| DE3122073C2 (enrdf_load_stackoverflow) | 1989-10-19 |
| KR850001156B1 (ko) | 1985-08-16 |
| IT8148596A0 (it) | 1981-06-01 |
| CH646936A5 (de) | 1984-12-28 |
| ES502917A0 (es) | 1982-04-01 |
| FR2484405A1 (fr) | 1981-12-18 |
| NL8102501A (nl) | 1982-01-04 |
| GB2077729A (en) | 1981-12-23 |
| SE8103635L (sv) | 1981-12-12 |
| BE889169A (fr) | 1981-10-01 |
| AU7081481A (en) | 1981-12-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |