DE1289040B - Tetrachlorterephthalsaeuredialkylester - Google Patents
TetrachlorterephthalsaeuredialkylesterInfo
- Publication number
- DE1289040B DE1289040B DE1966V0030456 DEV0030456A DE1289040B DE 1289040 B DE1289040 B DE 1289040B DE 1966V0030456 DE1966V0030456 DE 1966V0030456 DE V0030456 A DEV0030456 A DE V0030456A DE 1289040 B DE1289040 B DE 1289040B
- Authority
- DE
- Germany
- Prior art keywords
- terephthalate
- ester
- dialkyl
- tetrachloroterephthalate
- tetrachloride
- 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.)
- Pending
Links
- UAJSLAIYDXMAEH-UHFFFAOYSA-N OC(C(C=C1)=CC=C1C(O)=O)=O.Cl.Cl.Cl.Cl Chemical compound OC(C(C=C1)=CC=C1C(O)=O)=O.Cl.Cl.Cl.Cl UAJSLAIYDXMAEH-UHFFFAOYSA-N 0.000 title claims description 4
- -1 tetrachloroterephthalic acid methyl ester chloride Chemical compound 0.000 claims description 13
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- KZCBXHSWMMIEQU-UHFFFAOYSA-N Chlorthal Chemical compound OC(=O)C1=C(Cl)C(Cl)=C(C(O)=O)C(Cl)=C1Cl KZCBXHSWMMIEQU-UHFFFAOYSA-N 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- NPOJQCVWMSKXDN-UHFFFAOYSA-N Dacthal Chemical compound COC(=O)C1=C(Cl)C(Cl)=C(C(=O)OC)C(Cl)=C1Cl NPOJQCVWMSKXDN-UHFFFAOYSA-N 0.000 claims description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- HNUALPPJLMYHDK-UHFFFAOYSA-N C[CH]C Chemical group C[CH]C HNUALPPJLMYHDK-UHFFFAOYSA-N 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
- 239000000203 mixture Substances 0.000 description 10
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 7
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 6
- 238000000921 elemental analysis Methods 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- ZPXGNBIFHQKREO-UHFFFAOYSA-N 2-chloroterephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(Cl)=C1 ZPXGNBIFHQKREO-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 230000002363 herbicidal effect Effects 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 230000006378 damage Effects 0.000 description 3
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- NOHPQCSHYVUGOP-UHFFFAOYSA-N methyl 4-carbonochloridoyl-2,3,5,6-tetrachlorobenzoate Chemical compound COC(=O)C1=C(Cl)C(Cl)=C(C(Cl)=O)C(Cl)=C1Cl NOHPQCSHYVUGOP-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 240000001592 Amaranthus caudatus Species 0.000 description 2
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 2
- 244000025254 Cannabis sativa Species 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000002274 desiccant Substances 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 230000009528 severe injury Effects 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- CMEPUAROFJSGJN-UHFFFAOYSA-N 1,4-dioxan-2-ylmethanol Chemical compound OCC1COCCO1 CMEPUAROFJSGJN-UHFFFAOYSA-N 0.000 description 1
- SXINVWXSZUQKSW-UHFFFAOYSA-N 2,3,5,6-tetrachloro-4-methoxycarbonylbenzoic acid Chemical compound COC(=O)C1=C(Cl)C(Cl)=C(C(O)=O)C(Cl)=C1Cl SXINVWXSZUQKSW-UHFFFAOYSA-N 0.000 description 1
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 1
- LSAUQLHEUOZZLD-UHFFFAOYSA-N 4-o-ethyl 1-o-methyl 2,3,5,6-tetrachlorobenzene-1,4-dicarboxylate Chemical compound CCOC(=O)C1=C(Cl)C(Cl)=C(C(=O)OC)C(Cl)=C1Cl LSAUQLHEUOZZLD-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- OQHPOUNEQNPCLC-UHFFFAOYSA-N ClC1=C(C(=C(C(=C1C(=O)OC)Cl)Cl)C(=O)OCCCC)Cl Chemical compound ClC1=C(C(=C(C(=C1C(=O)OC)Cl)Cl)C(=O)OCCCC)Cl OQHPOUNEQNPCLC-UHFFFAOYSA-N 0.000 description 1
- 241000287828 Gallus gallus Species 0.000 description 1
- 244000062793 Sorghum vulgare Species 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011874 heated mixture Substances 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 230000009027 insemination Effects 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 235000019713 millet Nutrition 0.000 description 1
- 230000009526 moderate injury Effects 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/10—Aromatic or araliphatic carboxylic acids, or thio analogues thereof; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/80—Phthalic acid esters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US434625A US3335171A (en) | 1965-02-23 | 1965-02-23 | Methyl isopropyl tetrahaloterephthalates |
| US434654A US3341571A (en) | 1965-02-23 | 1965-02-23 | Methyl-n-propyl tetrahaloterephthalates |
| US434653A US3335172A (en) | 1965-02-23 | 1965-02-23 | Methyl ethyl tetrahaloterephthalates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1289040B true DE1289040B (de) | 1969-02-13 |
Family
ID=40813160
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1966V0030456 Pending DE1289040B (de) | 1965-02-23 | 1966-02-23 | Tetrachlorterephthalsaeuredialkylester |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE676953A (enrdf_load_stackoverflow) |
| DE (1) | DE1289040B (enrdf_load_stackoverflow) |
| ES (1) | ES323450A1 (enrdf_load_stackoverflow) |
| FR (1) | FR1469735A (enrdf_load_stackoverflow) |
| GB (1) | GB1102467A (enrdf_load_stackoverflow) |
| NL (1) | NL6602334A (enrdf_load_stackoverflow) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1265053A (fr) * | 1960-08-12 | 1961-06-23 | Diamond Alkali Co | Composés halogéno-organiques, notamment téréphtaliques, leur préparation et leurs applications |
| DE1112339B (de) * | 1958-04-04 | 1961-08-03 | Diamond Alkali Co | Mittel zur Verhinderung unerwuenschten Pflanzenwachstums |
| GB942911A (en) * | 1961-05-11 | 1963-11-27 | Diamond Alkali Co | Improvements in or relating to the production of halogenated aromatic carboxylic halides and esters |
-
1966
- 1966-02-21 FR FR50455A patent/FR1469735A/fr not_active Expired
- 1966-02-23 ES ES0323450A patent/ES323450A1/es not_active Expired
- 1966-02-23 BE BE676953D patent/BE676953A/xx unknown
- 1966-02-23 GB GB803166A patent/GB1102467A/en not_active Expired
- 1966-02-23 DE DE1966V0030456 patent/DE1289040B/de active Pending
- 1966-02-23 NL NL6602334A patent/NL6602334A/xx unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1112339B (de) * | 1958-04-04 | 1961-08-03 | Diamond Alkali Co | Mittel zur Verhinderung unerwuenschten Pflanzenwachstums |
| FR1265053A (fr) * | 1960-08-12 | 1961-06-23 | Diamond Alkali Co | Composés halogéno-organiques, notamment téréphtaliques, leur préparation et leurs applications |
| GB942911A (en) * | 1961-05-11 | 1963-11-27 | Diamond Alkali Co | Improvements in or relating to the production of halogenated aromatic carboxylic halides and esters |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1469735A (fr) | 1967-02-17 |
| ES323450A1 (es) | 1967-03-16 |
| NL6602334A (enrdf_load_stackoverflow) | 1966-08-24 |
| BE676953A (enrdf_load_stackoverflow) | 1966-08-23 |
| GB1102467A (en) | 1968-02-07 |
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