94-11-1

Basic information

• Product Name: Isopropyl 2,4-dichlorophenoxyacetate
• Synonyms: (2,4-dichlorophenoxy)-aceticaci1-methylethylester;(2,4-dichlorophenoxy)-aceticaci1-methylethylester[qr];(2,4-dichloro-phenoxy)-aceticacid1-methylethylester;(2,4-dichlorophenoxy)-aceticaciisopropylester;(2,4-dichlorophenoxy)-aceticaciisopropylester[qr];2,4-d,isopropylester[qr];2,4-dichlorophenoxyaceticacidisopropylester[qr];Acetic acid, (2,4-dichlorophenoxy)-, 1-methylethyl ester
• CAS NO: 94-11-1
• Molecular Formula: C₁₁H₁₂Cl₂O₃
• Molecular Weight: 263.12
• EINECS: 202-305-6
• Product Categories: Alpha sort;D;DAlphabetic;DIO - DIZEnvironmental Standards;Herbicides;MetabolitesPesticides&Metabolites;Pesticides&Metabolites;Phenoxy structure
• Mol File: 94-11-1.mol

Chemical Properties

• Melting Point: 5°C
• Boiling Point: 371.18°C (rough estimate)
• Flash Point: 126.2°C
• Appearance: /
• Density: 1.2600
• Vapor Pressure: 0.000273mmHg at 25°C
• Refractive Index: 1.5209 (estimate)
• Storage Temp.: 0-6°C
• Water Solubility: 27.36mg/L(temperature not stated)
• CAS DataBase Reference: Isopropyl 2,4-dichlorophenoxyacetate(CAS DataBase Reference)
• NIST Chemistry Reference: Isopropyl 2,4-dichlorophenoxyacetate(94-11-1)
• EPA Substance Registry System: Isopropyl 2,4-dichlorophenoxyacetate(94-11-1)

Safety Data

• Hazard Codes: Xn,N
• Statements: 22-41-50/53-43
• Safety Statements: 26-39-61-60-46-36/37-29
• RIDADR: 3348
• RTECS: AG8750000
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 94-11-1(Hazardous Substances Data)

Usage

Uses

Used in Herbicide Industry:
Isopropyl 2,4-dichlorophenoxyacetate is used as an active ingredient in herbicides for its ability to control a wide range of broadleaf weeds and grasses in various agricultural settings. Its selective action on weeds, without causing significant harm to crops, makes it a valuable tool in modern agriculture.
Used in Chemical Synthesis:
Isopropyl 2,4-dichlorophenoxyacetate serves as a key intermediate in the synthesis of various other chemical compounds, including pharmaceuticals, agrochemicals, and other specialty chemicals. Its unique structure allows for further functionalization and modification, enabling the development of new and innovative products.
Used in Research and Development:
As a chemical compound with distinct properties, Isopropyl 2,4-dichlorophenoxyacetate is utilized in research and development for the study of its potential applications and effects. This includes investigating its interactions with other molecules, understanding its mode of action, and exploring its potential use in new and emerging fields.

Waste Disposal

Incineration of phenoxys is effective in 1 second @ 982 C, using a straight combustion process or @ 482℃ using catalytic combustion. Over 99% decomposition was reported when small amounts of 2,4-D were burned in a polyethylene bag. See “References” for additional detail. In accordance with 40CFR165, follow (31); recommendations for the disposal of pesticides and pesticide containers. Must be disposed properly by follow- ing (100) Package (2) label directions or by contacting your local or federal environmental control agency, or by contacting your regional EPA office. Consult with environ- mental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≥100 kg/mo) must conform with EPA regu- lations governing storage, transportation, treatment, and waste disposal.

InChI:InChI=1/C11H12Cl2O3/c1-7(2)16-11(14)6-15-10-4-3-8(12)5-9(10)13/h3-5,7H,6H2,1-2H3

Upstream product

• 94-75-7 2,4-Dichlorophenoxyacetic acid 
• 67-63-0 isopropyl alcohol 
• 105-48-6 isopropyl chloroacetate 
• 120-83-2 2,4-dichlorophenol 
• 108-95-2 phenol 
• 49566-35-0 isopropyl 2-phenoxyacetate 

Downstream Products

• 94-75-7 2,4-Dichlorophenoxyacetic acid 
• 20940-37-8 diethylammonium 2,4-dichlorophenoxyacetate 
• 2702-72-9 sodium 2,4-dichlorophenoxyacetate 
• 3035-67-4 2,4-dichlorophenoxyacetic acid isooctyl ester 

Relevant articles and documents

Preparation method of 2,4-dichlorophenoxyacetic acid and salt thereof

The invention provides a preparation method of 2,4-dichlorophenoxyacetic acid and a salt thereof, wherein the preparation method includes the following steps: S1) carrying out a reaction of phenol andchloracetic ester under alkaline conditions to obtain phenoxyacetic ester; S2) carrying out selective chlorination reaction of the phenoxyacetic ester with a chlorinating agent under the action of acatalyst A and a catalyst B to obtain 2,4-dichlorophenoxyacetic ester, wherein the catalyst A is Lewis acid, and the catalyst B is C5-22 thioethers, thiazoles, isothiazoles and thiophenes or halogenated derivatives thereof; and S3) carrying out hydrolysis reaction of 2,4-dichlorophenoxyacetic ester under acidic conditions to obtain 2,4-dichlorophenoxyacetic acid; or after 2,4-dichlorophenoxyaceticester is obtained, carrying out an alkaline hydrolysis reaction with an alkaline compound to obtain 2,4-dichlorophenoxyacetate. The production and use of 2,4-dichlorophenol with unpleasant odor are avoided, the production of dioxins is eliminated, the yield of products is improved, and the output of three wastes is greatly reduced.

Preparation method of phenoxycarboxylate herbicide

The invention provides a preparation method of a phenoxycarboxylate herbicide, wherein the preparation method includes the steps: S1, carrying out condensation reaction of phenol or o-cresol with chlorocarboxylic ester under the action of alkaline substances to obtain phenoxycarboxylic ester, wherein chlorocarboxylic ester has the general formula of ClR1COOR, R1 is C1-3 alkylene or alkylidene, R is C1-10 alkyl of or C3-10 cycloalkyl; and S2, under the action of a first catalyst and a second catalyst, carrying out selective chlorination of the phenoxycarboxylic ester with a chlorinating agent to obtain the chlorophenoxycarboxylic ester represented by the formula I, R3 is H, Cl or CH3, the first catalyst is selected from Lewis acid, and the second catalyst is selected from C5-22 thioether, thiazole, isothiazole or thiophene compounds; and S3, mixing chlorophenoxycarboxylic ester with an alkaline compound, and carrying out alkaline hydrolysis to obtain the phenoxycarboxylate herbicide. The preparation method can improve the product quality and production operation environment, and has low quantity of three wastes.

Preparation method of phenoxycarboxylic acid choline salt

The invention provides a preparation method of a phenoxycarboxylic acid choline salt, wherein the preparation method includes the steps: S1, carrying out condensation reaction of phenol or o-cresol with chlorocarboxylic ester in the presence of alkaline substances to obtain phenoxycarboxylic ester; S2, carrying out selective chlorination of the phenoxycarboxylic ester with a chlorinating agent inthe presence of a first catalyst and a second catalyst to obtain chlorobenzoxycarboxylic ester; and S3, after reaction of trimethylamine with ethylene oxide, adding the chlorophenoxycarboxylic acid ester, and carrying out alkaline hydrolysis reaction to obtain the phenoxycarboxylic acid choline salt. Compared with a conventional synthesis technology, the preparation method effectively avoids the production and use of chlorophenols with unpleasant odor, radically eliminates the production of highly toxic dioxins, and greatly improves the product quality and the operation environment of the production site; with phenol as the raw material, through condensation, selective chlorination and alkaline hydrolysis, the high-quality phenoxycarboxylic acid choline salt is obtained, the loss of effective ingredients is effectively avoided and the yield of the product is increased.

A phenoxy carboxylic acid herbicide preparation method (by machine translation)

The invention provides a phenoxy carboxylic acid herbicide preparation method, including: S1, will be [...], alkaline substance mixed with the chlorinated carboxylic acid ester, in the one-pot condensation reaction in anhydrous system, phenoxy carboxylic acid ester obtained; the ClR states the chloro- carboxylic acid ester of the formula is1 COOR, R1 Is C1 - 3 alkylene or alkylidene, R is C1 - 10 alkyl or C3 - 10 cycloalkyl; S2, the [...] ester in the 1st and 2nd catalyst under the action of a catalyst, with the chlorinating agent to carry out the selective chlorination of, get [...] ester; the Lewis acid catalyst is selected from 1st, 2nd catalyst is C5 - 22 of the thioether compound, thiazole compound, isothiazole compound or thiophene compound; S3, will the [...] ester to acid hydrolysis reaction, as shown in formula I phenoxy carboxylic acid herbicide, R3 Is H, Cl or CH3 . This invention can improve the quality of the products and the operating environment of production, three waste low. (by machine translation)

Preparation method of phenoxycarboxylic acid herbicide

The invention provides a preparation method of a phenoxycarboxylic acid herbicide, wherein the preparation method includes the steps: S1, carrying out reaction of anhydrous phenol with an active metalto form phenoxide, and carrying out condensation reaction of the phenoxide with chlorocarboxylic ester to obtain phenoxycarboxylic ester, wherein the chlorocarboxylic ester has the general formula ofClR1COOR, R1 is C1-3 alkylene or alkylidene, and R is C1-10 alkyl or C3-10 of cycloalkyl; S2, carrying out selective chlorination of the phenoxycarboxylic ester with a chlorinating agent in the presence of a first catalyst and a second catalyst to obtain chlorobenzoxycarboxylic ester, wherein the first catalyst is selected from Lewis acid, and the second catalyst is C5-22 thioether, thiazole, isothiazole or thiophene compounds; and S3, carrying out acidolysis reaction of chlorobenzoxycarboxylic ester to obtain the phenoxycarboxylic acid herbicide represented by the formula I, wherein R3 is H,Cl or CH3. The preparation method can improve the product quality and the operation environment of the production site, and has low quantity of three wastes.

Preparation method of phenoxycarboxylic acid herbicide

The invention provides a preparation method of a phenoxycarboxylic acid herbicide, wherein the preparation method includes the steps: S1, carrying out condensation reaction of phenol or o-cresol withchlorocarboxylic ester under the action of an alkaline substance to obtain phenoxycarboxylic ester, wherein the chlorocarboxylic ester has the general formula of ClR1COOR, R1 is C1-3 alkylene or alkylidene, and R is C1-10 alkyl or C3-10 cycloalkyl; S2, carrying out selective chlorination of phenoxycarboxylic ester with a chlorinating agent under the action of a first catalyst and a second catalyst, to obtain chlorobenzoxycarboxylic ester, wherein the first catalyst is selected from Lewis acid, the second catalyst is C5-22 thioether compounds, thiazole compounds, isothiazole compounds or thiophene compounds; and S3, carrying out acidolysis reaction of chlorobenzoxycarboxylic ester, to obtain the phenoxycarboxylic acid herbicide represented by the formula I, wherein R3 is H, Cl or CH3. The preparation method can improve the product quality and the operation environment of a production site, and has low quantity of three wastes.

Preparation method of chlorophenoxycarboxamide salt

The invention provides a preparation method of chlorophenoxycarboxamide salt, wherein the preparation method includes the following steps: S1) carrying out 2-site and/or 4-site selective chlorinationreaction of phenoxycarboxylic ester with a chlorinating agent under the action of a catalyst A and a catalyst B to obtain chlorophenoxycarboxylic ester, wherein the catalyst A is Lewis acid, and the catalyst B has the following structural formula of R1'-S-R2'; and S2) carrying out ammonolysis reaction of chlorophenoxycarboxylic ester and amine to obtain chlorophenoxycarboxamide salt. By redesigning of the process route and fine screening of the catalysts and the chlorinating agent, the method reduces energy consumption, improves chlorination selectivity and avoids loss of effective components.The yield of the obtained chlorophenoxycarboxamide salt can reach 98.5% or more. At the same time, the production of high-salt wastewater is completely eradicated, the dust hazard caused by drying and use of chlorophenoxycarboxylic acid is avoided, energy is saved and equipment investment is reduced.

Preparation method of chlorophenoxycarboxamide salt

The invention provides a preparation method of chlorophenoxycarboxamide salt, wherein the preparation method includes the following steps: S1) carrying out 2-site and/or 4-site selective chlorinationreaction of phenoxycarboxylic ester with a chlorinating agent under the action of a catalyst A and a catalyst B to obtain chlorophenoxycarboxylic ester, wherein the catalyst A is Lewis acid, and the catalyst B is C5-22 thiazoles, isothiazoles and thiophenes or halogenated derivatives thereof; and S2) carrying out ammonolysis reaction of chlorophenoxycarboxylic ester and amine to obtain chlorophenoxycarboxamide salt. By redesigning of the process route and fine screening of the catalysts and the chlorinating agent, the method reduces energy consumption, improves chlorination selectivity and avoids loss of effective components. The yield of the obtained chlorophenoxycarboxamide salt can reach 99% or more. At the same time, the production of high-salt wastewater is completely eradicated, thedust hazard caused by drying and use of chlorophenoxycarboxylic acid is avoided, energy is saved and equipment investment is reduced.

Preparation method of chlorophenoxycarboxylic ester

The invention provides a preparation method of chlorophenoxycarboxylic ester, wherein the preparation method includes the following steps: S1) carrying out 2-site and/or 4-site selective chlorinationreaction of phenoxycarboxylic ester with a chlorinating agent under the action of a catalyst A and a catalyst B to obtain chlorophenoxycarboxylic ester, wherein the catalyst A is Lewis acid, the catalyst B is C5-22 thiazoles, isothiazoles and thiophenes or halogenated derivatives thereof, and the phenoxycarboxylic ester has any structure represented by the formulas I-IV; and S2) carrying out transesterification reaction of chlorophenoxycarboxylic ester and alcohol under the action of a catalyst to obtain long-chain chlorophenoxycarboxylic ester, wherein the alcohol has the molecular formula ofR2OH, and R2 is C4-20 alkyl or cycloalkyl. The method improves the yield and purity of chlorophenoxycarboxylic ester by redesigning of the process route and fine screening of the catalysts and the chlorinating agent. The content of the obtained chlorophenoxycarboxylic ester can reach 98.5% or more and the yield can reach 98.5% or more.

Preparation method of chlorophenoxycarboxylic ester

The invention provides a preparation method of chlorophenoxycarboxylic ester, wherein the preparation method includes the following steps: S1) carrying out 2-site and/or 4-site selective chlorinationreaction of phenoxycarboxylic ester with a chlorinating agent under the action of a catalyst A and a catalyst B to obtain chlorophenoxycarboxylic ester, wherein the catalyst A is Lewis acid, the catalyst B has the following structural formula of R1'-S-R2', and the phenoxycarboxylic ester has any structure represented by the formulas I-IV; and S2) carrying out transesterification reaction of chlorophenoxycarboxylic ester and alcohol under the action of a catalyst to obtain long-chain chlorophenoxycarboxylic ester, wherein the alcohol has the molecular formula of R2OH, and R2 is C4-20 alkyl or cycloalkyl. The method improves the yield and purity of chlorophenoxycarboxylic ester by redesigning of the process route and fine screening of the catalysts and the chlorinating agent. The content ofthe obtained chlorophenoxycarboxylic ester can reach 98.5% or more and the yield can reach 98.5% or more.