Ethoxyquin CAS 91-53-2
Introduction：Basic information about Ethoxyquin CAS 91-53-2, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Ethoxyquin Basic information
| Product Name: | Ethoxyquin |
| Synonyms: | 1,2-dihydro-2,2,4-trimethyl-6-ethoxyquinoline;2,2,4-trimethyl-6-ethoxy-1,2-dihydroquinoline;6-ethoxy-1,2-dihydro-2,2,4-trimethyl-quinolin;6-Ethoxyl-2,2,4-trimethyl-1,2-dihydrquinoline;amea100;antageaw;AntioxidantAW;antioxidantec |
| CAS: | 91-53-2 |
| MF: | C14H19NO |
| MW: | 217.31 |
| EINECS: | 202-075-7 |
| Product Categories: | C11 to C30;Building Blocks;Chemical Synthesis;Heterocyclic Building Blocks;Quinolines;Amines;Aromatics;Heterocycles;Antioxidant;Biochemistry;Industrial/Fine Chemicals;INORGANIC & ORGANIC CHEMICALS;91-53-2 |
| Mol File: | 91-53-2.mol |
Ethoxyquin Chemical Properties
| Melting point | <0°C |
| Boiling point | 123-125°C |
| density | 1.03 g/mL at 20 °C (lit.) |
| vapor pressure | 0.035Pa at 25℃ |
| refractive index | 1.569~1.571 |
| Fp | 137 °C |
| storage temp. | 2-8°C |
| solubility | ethanol: 50 mL/L, clear, brown |
| pka | 5.02±0.70(Predicted) |
| form | Liquid |
| color | Yellow to Very Dark Brown |
| Water Solubility | <0.1 g/100 mL at 20 ºC |
| Merck | 14,3753 |
| BRN | 158223 |
| Stability: | Stable. Combustible. Incompatible with oxidizing agents, strong acids. Polymerizes if heated. May polymerize upon exposure to light and air. |
| Major Application | cleaning products cosmetics food and beverages personal care |
| InChI | 1S/C14H19NO/c1-5-16-11-6-7-13-12(8-11)10(2)9-14(3,4)15-13/h6-9,15H,5H2,1-4H3 |
| InChIKey | DECIPOUIJURFOJ-UHFFFAOYSA-N |
| SMILES | CCOc1ccc2NC(C)(C)C=C(C)c2c1 |
| LogP | 3.39 |
| CAS DataBase Reference | 91-53-2(CAS DataBase Reference) |
| NIST Chemistry Reference | Quinoline, 6-ethoxy-1,2-dihydro-2,2,4-trimethyl-(91-53-2) |
| EPA Substance Registry System | Ethoxyquin (91-53-2) |
Safety Information
| Hazard Codes | Xn |
| Risk Statements | 22 |
| Safety Statements | 24 |
| RIDADR | 3082 |
| WGK Germany | 1 |
| RTECS | VB8225000 |
| F | 2-8-10 |
| TSCA | TSCA listed |
| HazardClass | 9 |
| PackingGroup | III |
| HS Code | 29334900 |
| Storage Class | 10 - Combustible liquids |
| Hazard Classifications | Acute Tox. 4 Oral |
| Hazardous Substances Data | 91-53-2(Hazardous Substances Data) |
| Toxicity | LD50 orally in rats, mice: 1920, 1730 mg/kg (Piul'skaya) |
| Description | Ethoxyquin is used as an antioxidant in animal feedand caused contact dermatitis in a worker at an animalfeed 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 ofcolor in apples and pears. It is used as an antioxidant topreserve color in paprika and ground and powdered chili.Ethoxyquin is also a chemical preservative used in animalfeed to prevent ingredients from reacting with oxygen andbecoming rancid. It has been known to cause birth defectsin pet birds and dogs. Not approved for use in EU countries[115]. Registered for use in the U.S. |
| Trade name | CHEMLEY®[C]; DECCOQUIN305®; EMQ®; EQ®; NIFLEX®; NIX-SCALD®[C];SANTOFLEX A®; SANTOFLEX AW®; SANTOQUIN®;SANTOQUINE®; STOP-SCALD® |
| Contact allergens | Ethoxyquin is used as an antioxidant in animal feedand caused contact dermatitis in a worker at an animalfeed mill |
| 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 | 156-43-4 67-64-1 91-53-2 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 andplant growth regulator. Also and ingredient in other products. Used for preharvest or postharvest preservation ofcolor in apples and pears. It is used as an anti-oxidant topreserve color in paprika and ground and powdered chili.Ethoxyquin also is a chemical preservative used in animalfeed to prevent ingredients from reacting with oxygen andbecoming rancid. It has been known to cause birth defectsin 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 contactwith strong light and/or water. Decomposes in temperaturesabove 150℃. Keep away from oxidizers (chlorates,nitrates, peroxides, permanganates, perchlorates, chlorine,bromine, fluorine, etc.); strong acids. |
| Waste Disposal | Do not discharge into drainsor sewers. Dispose of waste material as hazardous wasteusing a licensed disposal contractor to an approved landfill.Consult with environmental regulatory agencies forguidance 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 yourregional 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 |
Ethoxyquin Preparation Products And Raw materials
| Raw materials | Acetone-->PARA TOLUENE-->Benzenesulfonic acid-->Phenetidine |
| Preparation Products | Mesityl oxide-->2,2,4-TRIMETHYL-1,2-DIHYDRO-QUINOLIN-6-OL |
