CN106986767A - The preparation of high-purity chlorthal - Google Patents
The preparation of high-purity chlorthal Download PDFInfo
- Publication number
- CN106986767A CN106986767A CN201610880069.7A CN201610880069A CN106986767A CN 106986767 A CN106986767 A CN 106986767A CN 201610880069 A CN201610880069 A CN 201610880069A CN 106986767 A CN106986767 A CN 106986767A
- Authority
- CN
- China
- Prior art keywords
- chlorthal
- tetrachloro
- phenylene
- purity
- hours
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/10—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with ester groups or with a carbon-halogen bond
- C07C67/11—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with ester groups or with a carbon-halogen bond being mineral ester groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/08—Preparation of carboxylic acids or their salts, halides or anhydrides from nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a kind of preparation of high-purity chlorthal, using tetrachloro-p-phenylene's dimethoxy nitrile as initiation material, it is 1 that volume ratio is thrown in a kettle.:1 acetic acid and the mixing liquid of dilute sulfuric acid and tetrachloro-p-phenylene's dimethoxy nitrile, reacted 3-4 hours at 120-140 DEG C, reaction carries out suction filtration after terminating and obtains tetrachloro-p-phenylene's dioctyl phthalate, tetrachloro-p-phenylene's dioctyl phthalate is in the basic conditions, neutralization reaction 2-3 hours is carried out at 40-60 DEG C, reaction carries out filtering after terminating and goes the removal of impurity, and gained liquid is reacted with dimethyl suflfate again can obtain tetrachloroterephthalate, i.e. chlorthal.The technology of preparing of high-purity chlorthal of the present invention, processing step is simple, and reaction condition is gentle, easily controllable in actual production process, and products therefrom chlorthal content is more than 98%, and yield is more than 95%.
Description
Technical field
The present invention relates to a kind of preparation method of chlorthal, and in particular to a kind of preparation of high-purity chlorthal.
Background technology
Chlorthal abbreviation DCPA, general entitled Chlorthal-dimethyl；Trade name chlorthaldimethyl,
Dacthal or Fatal etc.；One tetrachloro of the entitled Dimethyl 2,3,5,6 of English-l, 4 one phthalate；Chemistry
Entitled 2,3,5,6 one tetrachloro-p-phenylene's dioctyl phthalate diformazan vinegar；CAs：[1,861 32 1 l]；Molecular formula is.Sterling is clear crystal,
Fusing point is 154-156 DEG C, water insoluble, is dissolved in the organic solvents such as acetone, benzene,toluene,xylene.
Chlorthal is benzoic acid herbicide, with uptake and translocation, can be used for bud pre-treatment, can be used for cauline leaf
Spraying.Suitable for crops such as corn, Kidney bean, cucumber, onion, capsicum, strawberry, lettuce, eggplant, turnips, apply also for lawn and
Ornamental plant, can prevent and kill off annual gramineous weed and some broad leaved weeds, such as green bristlegrass, lady's-grass, humid euphorbia, purslane, numerous
In detail, Semen Cuscutae etc..
The synthetic method of chlorthal document report is initiation material or terephthalic acid (TPA) as raw material predominantly using paraxylene
Synthesized, synthesis route is：In the case of POCl3 presence, terephthalic acid (TPA) is made to benzene with phosphorus pentachloride reaction
Dimethyl chloride, paraphthaloyl chloride is that catalyst is passed through chlorine progress benzene from anhydrous ferric trichloride in the presence of a lewis acid
Ring chlorination.Chlorination cools down the reactant system for having completed phenyl ring chlorination after terminating, add carbon tetrachloride by tetrachloro-p-phenylene's dimethyl chloride
Dissolving.Under carbon tetrachloride reflux temperature, slightly excessive first is added dropwise into the carbon tetrachloride mixed liquor of tetrachloro-p-phenylene's dimethyl chloride one
Alcohol, carries out esterification.Esterification terminates, and after washing, alkali cleaning, drying and words property carbon decoloring, solvent is evaporated off, you can
To chlorthal.
The technique of above-mentioned synthesis chlorthal passes through phosphorus pentachloride chloride, chlorination, ester using terephthalic acid (TPA) as initiation material
The processes such as change is washed again after reacting, alkali cleaning, precipitation, drying complete the preparation of chlorthal, and raw material and solvent used is more,
Production process is longer, while the three wastes are more in production, it is stronger to equipment corrosion, it is unfavorable for environmental protection and products therefrom
Purity and yield be not very high.
The content of the invention
For above-mentioned technical problem, the purpose of the present invention is：A kind of preparation of high-purity chlorthal is proposed, is made
Standby technique is simple, is suitable for industrialized production, and product yield reaches that more than 95%, content reaches more than 98%.
What the technical solution of the present invention was realized in：The preparation of high-purity chlorthal, it is with tetrachloro-p-phenylene's diformazan
Nitrile is initiation material, and it is 1 that volume ratio is thrown in a kettle.:1 acetic acid and the mixing liquid of dilute sulfuric acid and tetrachloro-p-phenylene's dimethoxy nitrile,
Reacted 3-4 hours at 120-140 DEG C, reaction carries out suction filtration after terminating and obtains tetrachloro-p-phenylene's dioctyl phthalate, tetrachloro-p-phenylene's diformazan
Acid in the basic conditions, saponification is carried out 2-3 hours at 40-60 DEG C, and reaction carries out filtering after terminating and goes the removal of impurity, gained
Liquid is reacted with dimethyl suflfate again can obtain tetrachloroterephthalate, i.e. chlorthal.
Due to the utilization of above-mentioned technical proposal, the present invention has following advantages compared with prior art：
The preparation of the high-purity chlorthal of the present invention, technique and operation are practical, and step is simple, not high to equipment requirement, fit
Industrialized production is closed, product yield reaches that more than 95%, content reaches more than 98%.
Embodiment
Embodiment 1
Acetic acid and dilute sulfuric acid sulfuric acid mixture 200mL are added in 1000mL three-necked flasks（Ratio is 1:1, content is respectively
80%、50%）, 66.7 grams of tetrachloro-p-phenylene's dimethoxy nitrile that content is 99% is separately added under agitation, is heated up at 120-125 DEG C
Lower reaction 3.5 hours, after reaction terminates, is cooled to 20-30 DEG C of progress suction filtrations, gained solid is tetrachloro-p-phenylene's dioctyl phthalate.
Tetrachloro-p-phenylene's dioctyl phthalate that above-mentioned steps are obtained is put into 1000mL three-necked flasks, while adding 30% hydrogen-oxygen
Change sodium solution 200mL, start stirring heating and neutralization reaction 2.5 hours is being carried out between 50-55 DEG C, after reaction terminates, carry out
Filtering, filtrate retains.
The filtrate that above-mentioned steps are obtained is put into 1000mL three-necked flasks, adds 250mL's in the case of stirring
DMF, 50 grams of the dimethyl suflfate that then disposable input content is 98%, insulation reaction is carried out after 5 hours between 40-45
77.3 grams of the chlorthal that content is more than 98.7% is obtained after precipitation, washing, drying, yield is 95.4%.
Embodiment 2
Acetic acid and dilute sulfuric acid sulfuric acid mixture 200mL are added in 1000mL three-necked flasks（Ratio is 1:1, content is respectively
80%、40%）, 66.7 grams of tetrachloro-p-phenylene's dimethoxy nitrile that content is 99% is separately added under agitation, is heated up at 130-155 DEG C
Lower reaction 3 hours, after reaction terminates, is cooled to 30 DEG C of progress suction filtrations, gained solid is tetrachloro-p-phenylene's dioctyl phthalate.
Tetrachloro-p-phenylene's dioctyl phthalate that above-mentioned steps are obtained is put into 1000mL three-necked flasks, while adding 30% hydrogen-oxygen
Change sodium solution 250mL, start stirring heating and neutralization reaction 3 hours is being carried out between 50-55 DEG C, after reaction terminates, carried out
Filter, filtrate retains.
The filtrate that above-mentioned steps are obtained is put into 1000mL three-necked flasks, adds 300mL's in the case of stirring
DMF, 52 grams of the dimethyl suflfate that then disposable input content is 98%, insulation reaction is carried out after 5 hours between 40-45
77.5 grams of the chlorthal that content is more than 98.8% is obtained after precipitation, washing, drying, yield is 95.5%.
The above embodiments merely illustrate the technical concept and features of the present invention, and its object is to allow person skilled in the art
Scholar can understand present disclosure and be carried out, and it is not intended to limit the scope of the present invention, all according to the present invention
The equivalent change or modification that Spirit Essence is made, should all cover within the scope of the present invention.
Claims (1)
1. the preparation of high-purity chlorthal, it is characterised in that：Using tetrachloro-p-phenylene's dimethoxy nitrile as initiation material, body is thrown in a kettle.
Product is than being 1:1 acetic acid and the mixing liquid of dilute sulfuric acid and tetrachloro-p-phenylene's dimethoxy nitrile, react 3-4 hours at 120-140 DEG C,
Reaction carries out suction filtration after terminating and obtains tetrachloro-p-phenylene's dioctyl phthalate, and tetrachloro-p-phenylene's dioctyl phthalate in the basic conditions, enters at 40-60 DEG C
Row neutralization reaction 2-3 hours, reaction carries out filtering after terminating and goes the removal of impurity, and gained liquid is reacted with dimethyl suflfate again
It can obtain tetrachloroterephthalate, i.e. chlorthal.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610880069.7A CN106986767A (en) | 2016-10-09 | 2016-10-09 | The preparation of high-purity chlorthal |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610880069.7A CN106986767A (en) | 2016-10-09 | 2016-10-09 | The preparation of high-purity chlorthal |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN106986767A true CN106986767A (en) | 2017-07-28 |
Family
ID=59413994
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201610880069.7A Pending CN106986767A (en) | 2016-10-09 | 2016-10-09 | The preparation of high-purity chlorthal |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN106986767A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6865489B1 (en) * | 2020-10-20 | 2021-04-28 | 株式会社エス・ディー・エス バイオテック | Method for producing dimethyl 2,3,5,6-tetrachloro-1,4-benzenedicarboxylic acid |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN201825893U (en) * | 2010-10-08 | 2011-05-11 | 蒙健 | Novel chlorthal production device |
| CN102432470A (en) * | 2010-09-29 | 2012-05-02 | 蒙健 | Novel production process of chlorthal |
| WO2013140506A1 (en) * | 2012-03-19 | 2013-09-26 | エア・ウォーター株式会社 | Method for manufacturing 4,4'-oxydiphthalic acid and method for manufacturing 4,4'-oxydiphthalic dianhydride |
| CN104803843A (en) * | 2015-03-27 | 2015-07-29 | 江苏长青农化南通有限公司 | Production technology for dicamba |
-
2016
- 2016-10-09 CN CN201610880069.7A patent/CN106986767A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102432470A (en) * | 2010-09-29 | 2012-05-02 | 蒙健 | Novel production process of chlorthal |
| CN201825893U (en) * | 2010-10-08 | 2011-05-11 | 蒙健 | Novel chlorthal production device |
| WO2013140506A1 (en) * | 2012-03-19 | 2013-09-26 | エア・ウォーター株式会社 | Method for manufacturing 4,4'-oxydiphthalic acid and method for manufacturing 4,4'-oxydiphthalic dianhydride |
| CN104803843A (en) * | 2015-03-27 | 2015-07-29 | 江苏长青农化南通有限公司 | Production technology for dicamba |
Non-Patent Citations (2)
| Title |
|---|
| 陈子明，樊能廷: "除草剂敌草索的合成", 《河北化工》 * |
| 黄书盛: "除草剂敌草索的合成试验", 《广东化工》 * |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6865489B1 (en) * | 2020-10-20 | 2021-04-28 | 株式会社エス・ディー・エス バイオテック | Method for producing dimethyl 2,3,5,6-tetrachloro-1,4-benzenedicarboxylic acid |
| WO2022085211A1 (en) * | 2020-10-20 | 2022-04-28 | 株式会社エス・ディー・エス バイオテック | Method for producing dimethyl 2,3,5,6-tetrachloro-1,4-benzenedicarboxylate |
| JP7095931B1 (en) * | 2020-10-20 | 2022-07-05 | 株式会社エス・ディー・エス バイオテック | Method for producing dimethyl 2,3,5,6-tetrachloro-1,4-benzenedicarboxylate |
| CN114728879A (en) * | 2020-10-20 | 2022-07-08 | Sds生物技术株式会社 | Method for producing dimethyl 2,3,5, 6-tetrachloro-1, 4-phthalate |
| US20220267244A1 (en) * | 2020-10-20 | 2022-08-25 | Sds Biotech K.K. | Process for producing dimethyl 2,3,5,6-tetrachloro-1,4-benzenedicarboxylate |
| US11512037B2 (en) * | 2020-10-20 | 2022-11-29 | Sds Biotech K.K. | Process for producing dimethyl 2,3,5,6-tetrachloro-1,4-benzenedicarboxylate |
| CN114728879B (en) * | 2020-10-20 | 2023-11-14 | Sds生物技术株式会社 | Method for producing 2,3,5, 6-tetrachloro-1, 4-dimethyl phthalate |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN102516078B (en) | Preparation methods of glyoxylic acid L-menthyl alcohol ester and monohydrate of glyoxylic acid L-menthyl alcohol ester | |
| CN105906627A (en) | Synthesis method of linagliptin intermediate | |
| CN108503564A (en) | A kind of Mivacurium Chloride intermediate and the method using intermediate synthesis Mivacurium Chloride | |
| CN106986767A (en) | The preparation of high-purity chlorthal | |
| CN110734409A (en) | Synthesis method of metamifop | |
| CN107118187A (en) | A kind of preparation method of 3 hydroxyl phthalic anhydride | |
| CN103086959A (en) | Novel process for producing 3,5,6-sodium trichloropyrindinol | |
| CN104892418A (en) | Synthesis method of citric acid tributyl citrate | |
| CN107011381A (en) | The control method of objectionable impurities in pirimiphos-methyl synthesis | |
| CN102351790A (en) | Method for synthesizing 7-bromo-6-chloro-4-quinazolinone | |
| CN101723856A (en) | Method for preparing cyhalothrin | |
| CN109836344B (en) | Method for producing glycine by organic solvent | |
| CN103553932A (en) | Method suitable for industrially preparing memanitine hydrochloride | |
| CN104402813B (en) | Novel method for synthesizing sorafenib | |
| CN103724213B (en) | A kind of synthetic method of 2,6-di-isopropyl-4-phenoxybenzamine | |
| CN106565556A (en) | Synthetic process of mesotrione | |
| CN101134711A (en) | Method for preparing pentabromobenzyl bromide | |
| CN108484669B (en) | Preparation method of thiotepa | |
| CN109575019A (en) | A kind of preparation method of 5- bromo-7-azaindole | |
| JPS60139627A (en) | Manufacture of water-soluble vic-diol | |
| CN101633596B (en) | Refining method of biphenyl functioning as addition agent of non-aqueous electrolyte | |
| CN113372228B (en) | Preparation method of 2-amino-6-chloro-4-nitrophenol | |
| CN105198834B (en) | The synthesis technique of 2,6 dibromo benzothiazoles | |
| CN109627141B (en) | Efficient preparation method of 2,3,6, 7-tetramethylanthracene and application of efficient preparation method in preparation of triptycene and derivatives thereof | |
| CN103880760A (en) | Synthesis method of 5-(trifluoromethyl) uracil |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| WD01 | Invention patent application deemed withdrawn after publication | ||
| WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20170728 |