84-51-5

Basic information

• Product Name: 2-Ethyl anthraquinone
• Synonyms: 10-Anthracenedione,2-ethyl-9;2-ethyl-10-anthracenedione;2-Ethyl-9,10-anthraquinone;2-Ethylanthra-9,10-quinone;2-ethyl-anthraquinon;9,10-Anthracenedione,2-ethyl-;Anthraquinone, 2-ethyl-;beta-ethylanthraquinone
• CAS NO: 84-51-5
• Molecular Formula: C₁₆H₁₂O₂
• Molecular Weight: 236.27
• EINECS: 201-535-4
• Product Categories: Intermediates of Dyes and Pigments;Organics;Anthraquinones;Chloroanthraquine, etc.;Functional Materials;Photopolymerization Initiators;Photoluminescent Materials > Light-Emitting Dopants and Fluorescent Dyes;Photonic and Optical Materials
• Mol File: 84-51-5.mol
• Article Data: 32

Chemical Properties

• Melting Point: 108-111 °C(lit.)
• Boiling Point: 180-190°C
• Flash Point: >210°C
• Appearance: white or yellowish crystals or powder
• Density: 1.27 g/cm3 (21℃)
• Vapor Pressure: 4.14E-07mmHg at 25°C
• Refractive Index: 1.6290 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: 0.00025g/l
• Water Solubility: Insoluble in water.
• Stability: Stable. Combustible. Incompatible with strong oxidizing agents.
• BRN: 1969873
• CAS DataBase Reference: 2-Ethyl anthraquinone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Ethyl anthraquinone(84-51-5)
• EPA Substance Registry System: 2-Ethyl anthraquinone(84-51-5)

Safety Data

• Hazard Codes: Xn,N
• Statements: 22-36/37/38-50/53-48/22
• Safety Statements: 24/25-36-26-61-60-37
• RIDADR: UN 3077 9 / PGIII
• WGK Germany: 1
• RTECS: CB0525000
• TSCA: Yes
• Hazardous Substances Data: 84-51-5(Hazardous Substances Data)

Usage

Chemical Properties

white or yellowish crystals or powder

Uses

Different sources of media describe the Uses of 84-51-5 differently. You can refer to the following data:
1. Synthesis, especially of hydrogen peroxide.
2. 2-Ethylanthraquinone can be used as a photoinitiator of crosslinking or degradation of polyethylene. It is used to produce hydrogen peroxide by hydrogenation with the help of Pd/polyaniline as the catalysts.

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C16H12O2/c1-2-10-7-8-13-14(9-10)16(18)12-6-4-3-5-11(12)15(13)17/h3-9H,2H2,1H3

Upstream product

• 62167-65-1 2-ethyl-9,10-dihydroanthracene 
• 839-73-6 2-ethylanthracene-9,10-diol 
• 100-41-4 ethylbenzene 
• 1151-14-0 2-(4’-ethylbenzoyl)benzoic acid 
• 70419-43-1 9,10-diacetoxy-2-ethylanthracene 
• 78246-03-4 ortho(4'-ethylbenzoyl)benzoic acid chloride 
• 85-44-9 phthalic anhydride 
• 10210-32-9 2-acetylanthracene 
• 26708-04-3 2-ethyl-9,10-dimethoxy-anthracene 
• 142354-70-9 2-(3-Ethyl-benzoyl)-benzoic acid 
• 3248-28-0 dipropionyl peroxide 
• 84-65-1 9,10-phenanthrenequinone 
• 64-19-7 acetic acid 
• 76682-71-8 2-ethyl-10H-9-anthranone 

Downstream Products

• 68279-54-9 2-ethyl-5,6,7,8-tetrahydro-9,10-anthrahydroquinone 
• 286463-72-7 2-ethyl-9H-10-anthranone 
• 15547-17-8 6-ethyl-1,2,3,4-tetrahydroanthracene-9,10-dione 
• 76682-71-8 2-ethyl-10H-9-anthranone 
• 1456629-29-0 2-[1-(4-phenyl-1,2,3-triazol-1-yl)ethyl]anthraquinone 
• 1456629-38-1 2-[1-(toluene-4-sulfonyl)ethyl]anthraquinone 
• 1456629-40-5 2-(1-phenylsulfanylethyl)anthraquinone 
• 1456629-41-6 1-nitro-2-[1-(toluene-4-sulfonyl)ethyl]anthraquinone 
• 1456629-42-7 2-[2-(toluene-4-sulfonyl)pent-4-en-2-yl]anthraquinone 
• 1456629-43-8 2-[3-phenyl-2-(toluene-4-sulfonyl)propan-2-yl]anthraquinone 
• 1456629-44-9 2-[5-phenyl-2-(toluene-4-sulfonyl)pent-4-en-2-yl]anthraquinone 
• 1456629-45-0 2-[2-(toluene-4-sulfonyl)hex-3-en-2-yl]anthraquinone 
• 1456629-46-1 2-[2-(toluene-4-sulfonyl)propan-2-yl]anthraquinone 
• 1456629-33-6 2-[1-(4-(p-tolyl)-1,2,3-triazol-1-yl)ethyl]anthraquinone 

Relevant articles and documents

Photocatalytically green synthesis of H2O2 using 2-ethyl-9,10-anthraquinone as an electron condenser

A high level (～9 mM) of hydrogen peroxide is photocatalytically synthesized by using O2 as an oxidant and 2-ethyl-9,10-anthraquinone (EAQ) as an electron condenser. The photo-catalytic efficiency of the EAQ-assisted H2O2 production is ca. 10-fold higher than that of H2 generation with Pt/P25. This journal is

Hydrogen peroxide synthesis by direct photoreduction of 2-ethylanthraquinone in aerated solutions

A new synthesis method of hydrogen peroxide was investigated by the photoreduction of 2-ethylanthraquinone (AQ) in water-insoluble organic solvents. Through optimizing the photoreduction condition including solvent, atmosphere and irradiated time, the photolysis system of 1,3,5-trimethylbenzene/trioctyl phosphate (3:1) solvent mixture under oxygen atmosphere was found to give a high yield of hydrogen peroxide. Furthermore, the formation mechanism of hydrogen peroxide was proposed, i.e. photoreduction and subsequent oxidation of AQ. The photoreduction of 2-ethylanthraquinone undergoes the hydrogen abstraction from solvent to form the anthrahydroquinone, which is subsequently oxidized by oxygen to give hydrogen peroxide.

Engineering the porosity and acidity of H-Beta zeolite by dealumination for the production of 2-ethylanthraquinone via 2-(4′-ethylbenzoyl)benzoic acid dehydration

Environmentally-friendly zeolites have been used commercially to replace concentrated sulfuric acid and oleum in the alkylation reactions and dehydration of alcohols. However, moderate activity, associated with access and diffusion limitations, low intramolecular dehydration selectivity, associated with unsatisfactory acidity, and unknown reusability have hampered their industrial implementation in the dehydration of bulky 2-(4′-ethylbenzoyl)benzoic acid (E-BBA) to 2-ethylanthraquinone (2-EAQ). Herein, we have discovered that after being treated with mild HNO3, nano-sized H-Beta zeolite showed outstanding catalytic activity, selectivity and reusability, compared with a commercial oleum catalyst. A number of techniques, such as XRD, XPS, XRF, 29Si MAS NMR, 27Al MQ MAS NMR, FTIR, NH3-TPD, argon physisorption and HR-TEM, have been employed to decouple the interdependence between acidity, porosity and catalytic performance. It was found that mild HNO3 treatment could clean out the extra-framework aluminium deposits and selectively extract the aluminium species on the outer surface of Beta zeolites, which strengthened the acidity of the Br?nsted acid sites (Si(OH)Al) inside the H-Beta micropores, thus increasing the possibility of intramolecular dehydration of E-BBA. Moreover, this mild HNO3 treatment also dredged the network of intercrystalline mesopores, alleviating the diffusion constraints. Therefore, through the dual adjustment of acidity and porosity, dealuminated H-Beta zeolite has a promising future in the green synthesis of 2-EAQ.

Role of phosphorus in the formation of selective palladium catalysts for hydrogenation of alkylanthraquinones

Effective Pd-P catalysts for the hydrogenation of 2-ethyl-9,10-anthraquinone in a toluene/1-octanol medium were obtained. Phosphorus modification increases the selectivity of the active quinones from 69% to 93%–97%, and the deposition of Pd-P catalyst particles on a carbon support increases their activity fivefold due to increased dispersion without a decrease in selectivity to the target product. Using energy dispersive X-ray spectroscopy, X-ray powder diffraction, high-resolution transmission electron microscopy and X-ray photoelectron spectroscopy, the composition, size and state of the surface layers of Pd-P catalysts were determined. Surface enrichment by the electron-deficient palladium and structural disorder of Pd-P catalyst particles were shown to account for the increase in selectivity to active quinones during hydrogen peroxide production by the anthraquinone method.

Friedel - gram acylating reaction method based on phthalic anhydride and aromatic alkyl compound

A part of a substituted alkylbenzene is used as a solvent and a reaction raw material for - gram acylating reaction, a part of a substituted alkylbenzene is dissolved in a reaction raw material phthalic anhydride and a chloroaluminate ionic liquid catalyst, and a residual part of a substituted alkylbenzene is added dropwise - to obtain - (2 - 4' - alkylbenzoyl) benzoic acid intermediate. 2 -position positioning selectivity of the method is higher, and the reaction production cost is low.

PROCESS FOR PRODUCING SUBSTITUTED ANTHRAQUINONE

A process for manufacturing a compound of formula (II), said process comprising a step of reacting a compound of formula (I) in the presence of a zeolite catalyst and a solvent, (I), (II) wherein R1, R2, R3, R4, R5, R6, R7 and R8 are independently H, halo, C1-C12 alkyl, C1-C12 alkyloxy, C2-C12 alkenyl, C2-C12 alkenyloxy, C2-C12 alkynyl, C2-C12 alkynyloxy, C3-C8 cycloalkyl, C3-C8 cycloalkyloxy, C6-C10 aryl, C6-C10 aryloxy, C7-C10 aralkyl, C7-C10 alkylaryl or C4-C7 heteroaryl; and wherein the solvent is a halogen substituted aromatic compound.

Green synthesis method for preparing 2-alkylanthraquinone from phthalic anhydride in one step

The invention relates to the technical field of green synthesis of organic matters. The invention relates to a synthetic method, in particular to a green synthetic method for preparing 2-alkylanthraquinone from phthalic anhydride in one step. According to the method, phthalic anhydride and alkylbenzene are used as raw materials, difunctional sulfonic acid type solid acid based on an HZSM-5 molecular sieve is used as a catalyst, phthalic anhydride and alkylbenzene are catalyzed to be subjected to a Friedel-Crafts acylation reaction and a dehydration cyclization reaction at the same time under the action of the catalyst, so that the 2-alkyl anthraquinone is prepared in one step, wherein the bifunctional sulfonic acid type solid acid based on the HZSM-5 molecular sieve is a sulfonic acid typeHZSM-5 molecular sieve obtained by carrying out sulfonation treatment on the HZSM-5 molecular sieve. According to the synthesis method of the 2-alkyl anthraquinone, the bifunctional (with strong Bronsted acidity and Lewis acidity) sulfonic acid type solid acid based on the HZSM-5 molecular sieve is used as the catalyst to replace AlCl3 and fuming sulfuric acid, so that generation of a large amount of waste residues, waste gas and wastewater is avoided, and green production is realized.

Method for synthesizing 2-alkylanthraquinone

The invention discloses a method for synthesizing 2-alkylanthraquinone. The method comprises the following steps: preparing a tert-butylanthraquinone intermediate BE acid from phthalic anhydride and alkylbenzene in the presence of a Lewis acid, carrying out dehydration ring closure by adopting a combined dehydrating agent composed of polyphosphoric acid and phosphorus pentoxide, pouring the obtained solution into ice water after the end of the ring closure I order to dilute the polyphosphoric acid to a certain concentration, adding xylene for extraction after water precipitation is finished, washing and concentrating the obtained extract to obtain a brown yellow block solid, and recrystallizing the solid to obtain the 2-alkylanthraquinone. The method of the invention the advantages of avoiding of using of fuming sulfuric acid and production of a large amount of dilute sulfuric acid in the phthalic anhydride method production process of anthraquinone, easily available raw materials, mild reaction conditions, easiness in application in industrial production, realization of continuous using of the byproduct phosphoric acid as the dehydrating agent after addition of phosphorus pentoxide, and good environmental protection meaning.

Method for driving molecular oxygen to selectively oxidize 9,10-dihydroanthracene and quantitatively convert 9,10-dihydroanthracene into anthraquinone by visible light

The invention relates to the technical field of photooxidation synthesis, and discloses a simple, convenient and practical visible light synthesis method for quantitatively converting 9, 10-dihydroanthracene into anthraquinone based on molecular oxygen selective oxidation. Under a condition of normal temperature, normal pressure, pure oxygen atmosphere and no catalysts and additives, the synthesismethod can realize 100% raw material conversion and provide a anthraquinone yield of 99.3%, and 86.4% of anthraquinone yield can be obtained even in an air atmosphere. Moreover, the synthesis methodalso shows a good effect on photooxidation of other compounds with structures similar to the structure of 9, 10-dihydroanthracene, and the synthesis method is indicated to have relatively wide applicability. The visible light synthesis method provided by the invention provides a very good example for participation of active O2 of a substrate in selective oxidation, and accords with the concept ofgreen chemistry.

Preparation method of 2-ethylanthracene

The invention discloses a preparation method of 2-ethylanthracene. The preparation method comprises the following steps: firstly, 2-(4-ethylbenzoyl) benzoic acid is prepared; then, 2-(4-ethylbenzoyl)benzoic acid is subjected to a reaction with concentrated sulfuric acid in a tubular reactor comprising a T-shaped mixer, a reactor A, a Y-shaped mixer, a reactor B and a separator, and 2-ethyl anthraquinone is prepared; finally, a strong ammonia solution as a reaction medium, crystalline copper sulfate as a catalyst, zinc powder as a reducing agent, and 2-ethyl anthraquinone as a raw material aresubjected to reflux reaction at 70-80 DEG C for 1-3 h, a reaction product is cooled to the room temperature after the reaction and is subjected to silica-gel column chromatography, and 2-ethylanthracene is prepared. The disclosed method is simple to operate, and the yield of the target product is high.