Synthesis
It is obtained by chlorination and reduction of o-nitrotoluene.
1. Chlorination reaction
In o-nitrotoluene, add 2% ferric chloride as a catalyst, pass chlorine gas at 50-60 ° C until the relative density of the reaction solution reaches 1.27-1.29 (50 ° C), wash with 5% hydrochloric acid, and then Wash with water, and finally adjust pH to 7 with liquid caustic soda. Divide the water layer, evaporate the water, carry out vacuum distillation, collect 120-150 ℃ (5.33-8.0kPa) fractions, crystallize by cooling and filter to obtain 2-chloro-6-nitrotoluene.
2. Reduction reaction
Add hydrochloric acid and iron powder to the reaction pot, stir and heat to 90°C, slowly add melted 2-chloro-6-nitrotoluene, complete the addition, and reflux for 3 hours. Cooling, adding liquid alkali to adjust pH to 8, steam distillation to obtain 3-chloro-o-toluidine.
Description
The chloromethylanilines are colorless orwhite crystalline solids or liquids, some have a mild fishyodor. Molecular weight (all isomers) =141.61. HazardIdentification (based on NFPA 704 M Rating System): (87-60-5) Health 2, Flammability 1, Reactivity 0. All are soluble in water and include:
Chemical Properties
clear yellow to red or red-brown liquid
Chemical Properties
The chloromethylanilines are colorless or
white crystalline solids or liquids, some have a mild
fishy odor.
Uses
3-Chloro-2-Methylaniline can be used for dyeing cotton, viscose, silk, nylon and acetate, as well as printing on cotton. It is mainly used for dyeing red, such as coupling with chromophenol AS, AS-BO, AS-ITR, etc.
Preparation
By 1-Methyl-2-nitrobenzene chlorination byproducts 3-Chloro-2-methylbenzenaminereduction.
Hazard
Toxic by ingestion or inhalation.
Safety Profile
Poison by ingestion.
Mutation data reported. When heated to
decomposition it emits toxic fumes of Cl
and NOx. See also other chloro toluidine
entries.
Potential Exposure
Most of the isomers are used in dyestuff manufacture. The 3-chloro-para isomer is used to kill
birds. It is marketed as pelleted bait for control of bird
populations.
First aid
If this chemical gets into the eyes, remove anycontact lenses at once and irrigate immediately for at least15 min, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts theskin, remove contaminated clothing and wash immediatelywith soap and water. Seek medical attention immediately. Ifthis chemical has been inhaled, remove from exposure,begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR ifheart action has stopped. Transfer promptly to a medicalfacility. When this chemical has been swallowed, get medical attention. Give large quantities of water and inducevomiting. Do not make an unconscious person vomit.
Note to physician: Treat for methemoglobinemia.Spectrophotometry may be required for precise determination of levels of methemoglobinemia in urine.
storage
Color Code—Blue: Health Hazard/Poison: Store ina secure poison location. Prior to working with chloromethylanilines you should be trained on its proper handling andstorage. Store in tightly closed containers in a cool, well-ventilated area. Sources of ignition, such as smoking and openflames, are prohibited where Choromethyl anilines are handled, or stored in a manner that could create a potential fireor explosion hazard. A regulated, marked area should beestablished where this chemical is handled, used, or stored incompliance with OSHA Standard 1910.1045.
Shipping
Chlorotoluidines require a label of“POISONOUS/TOXIC MATERIALS.” They fall in DOTHazard Class 6.1 and Packing Group III.
Incompatibilities
Incompatible with oxidizers, strong
acids; chloroformates, and acid anhydrides, isocyanates,
aldehydes forming fire and explosive hazards.
References
[1] Materials Research Bulletin, 2013, vol. 48, # 5, p. 1885 - 1890
[2] Bulletin of the Korean Chemical Society, 2012, vol. 33, # 9, p. 2851 - 2852
[3] Patent: CN104725242, 2017, B. Location in patent: Paragraph 0026-0027
[4] Journal of the Chemical Society. Perkin Transactions 1, 2001, # 9, p. 955 - 977
[5] Synthetic Communications, 1981, vol. 11, # 11, p. 925 - 930
