Description
Ethoxyquin is used as an antioxidant in animal feed
and caused contact dermatitis in a worker at an animal
feed mill.
Chemical Properties
Transparent yellow or brown viscous liquid. Discolors and stains badly. Soluble in benzene, gasoline, ether, ethanol, carbon tetrachloride, acetone, dichloroethane, insoluble in water.
Uses
Antioxidant in feed and food; antidegradation agent for rubber.
Uses
Ethoxyquin is an antioxidant used in the preservation of color in
chili powder, ground chili, and paprika.
Definition
ChEBI: Ethoxyquin is a quinoline that is 1,2-dihydroquinoline bearing three methyl substituents at position 2, 2 and 4 as well as an ethoxy substituent at position 6. It has a role as a herbicide, an UDP-glucuronosyltransferase activator, a neuroprotective agent, a Hsp90 inhibitor, a genotoxin, a food antioxidant, a geroprotector and an antifungal agrochemical. It is a member of quinolines and an aromatic ether.
General Description
Clear light yellow to dark brown viscous liquid. Discolors and stains badly. Mercaptan-like odor.
Air & Water Reactions
Polymerizes and darkens in color on exposure to light and air. Insoluble in water.
Reactivity Profile
Ethoxyquin may undergo a hazardous polymerization at temperatures above 320° F. Tends to polymerize and darken in color on exposure to light and air. Not compatible with oxidizing agents and with strong acids .
Hazard
Toxic by ingestion.
Fire Hazard
Ethoxyquin is combustible.
Agricultural Uses
Insecticide, Fungicide, Plant growth regulator,
Ingredient in other products: Used for preharvest or postharvest preservation of
color in apples and pears. It is used as an antioxidant to
preserve color in paprika and ground and powdered chili.
Ethoxyquin is also a chemical preservative used in animal
feed to prevent ingredients from reacting with oxygen and
becoming rancid. It has been known to cause birth defects
in pet birds and dogs. Not approved for use in EU countries[
115]. Registered for use in the U.S.
Trade name
CHEMLEY®[C]; DECCOQUIN
305®; EMQ®; EQ®; NIFLEX®; NIX-SCALD®[C];
SANTOFLEX A®; SANTOFLEX AW®; SANTOQUIN®;
SANTOQUINE®; STOP-SCALD®
Contact allergens
Ethoxyquin is used as an antioxidant in animal feed
and caused contact dermatitis in a worker at an animal
feed mill
Mechanism of action
Anti-oxidant effecting plant growth. Ethoxyquin may also inhibit heat shock protein 90 (Hsp90), a molecular chaperone involved in protein folding and stress responses
Safety Profile
Poison by intraperitoneal route. Moderately toxic by ingestion. Mutation data reported. Combustible when exposed to heat or flame; can react with oxidizing materials. When heated to decomposition it emits toxic fumes of NOx.
Synthesis
The general procedure for the synthesis of ethoxyquinoline from p-ethoxyaniline and acetone was as follows: 100 kg of p-aminoanisole, 30 kg of the solvent acetic anhydride and 5 kg of the catalyst cuprous chloride were added to the reaction tank and mixed thoroughly. Subsequently, the reaction mixture was heated to 130°C, and the titration rate of acetone was controlled by a rotameter at atmospheric pressure, and a total of 210 kg of acetone was titrated. The reaction lasted for 12 hours, during which the content of ethoxyquinoline in the reaction mixture was determined periodically. When the content of ethoxyquinoline reached 90% or higher, the reaction mixture was cooled to 75°C. Water and unreacted acetone produced during the reaction were recovered by condensation and the acetone was recycled.
Potential Exposure
Quinoline insecticide, fungicide and
plant growth regulator. Also and ingredient in other products. Used for preharvest or postharvest preservation of
color in apples and pears. It is used as an anti-oxidant to
preserve color in paprika and ground and powdered chili.
Ethoxyquin also is a chemical preservative used in animal
feed to prevent ingredients from reacting with oxygen and
becoming rancid. It has been known to cause birth defects
in pet birds and dogs
Shipping
UN3082 Environmentally hazardous substances,
liquid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name Required
Purification Methods
Purify Ethoxyquin by fractional distillation in vacuo whereby the distillate solidifies to a glass. [Knoevenagel Chem Ber 54 1723, 1730 1921.] The methiodide has m 179o (from EtOH), and the 1-phenylcarbamoyl derivative has m 146-147o (from EtOH). [Beaver et al. J Am Chem Soc 79 1236 1957, Beilstein 21 III/IV 95.]
Incompatibilities
Polymerization can occur on contact
with strong light and/or water. Decomposes in temperatures
above 150℃. Keep away from oxidizers (chlorates,
nitrates, peroxides, permanganates, perchlorates, chlorine,
bromine, fluorine, etc.); strong acids.
Waste Disposal
Do not discharge into drains
or sewers. Dispose of waste material as hazardous waste
using a licensed disposal contractor to an approved landfill.
Consult with environmental regulatory agencies for
guidance on acceptable disposal practices. If allowed,
Incineration with effluent gas scrubbing is recommended.
Containers must be disposed of properly by following package label directions or by contacting your local or federal environmental control agency, or by contacting your
regional EPA office
References
[1] Heteroatom Chemistry, 2012, vol. 23, # 6, p. 598 - 604
[2] Chemische Berichte, 1921, vol. 54, p. 1723,1730
[3] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 21, p. 5081 - 5085
[4] Patent: CN104961679, 2016, B. Location in patent: Paragraph 0023; 0044-0053
[5] European Journal of Pharmaceutical Sciences, 2018, vol. 118, p. 67 - 79
Pesticide Type
Fungicide; Veterinary substance
