Dibutyl ether

Base Information

• Chemical Name: Dibutyl ether
• CAS No.: 142-96-1
• Molecular Formula: C8H18O
• Molecular Weight: 130.23
• Hs Code.: 29091990
• European Community (EC) Number: 205-575-3
• ICSC Number: 1150
• NSC Number: 8459
• UN Number: 1149
• UNII: PBM2R52P5G
• DSSTox Substance ID: DTXSID1022007
• Nikkaji Number: J5.816E
• Wikipedia: Dibutyl_ether
• Wikidata: Q1207808
• Metabolomics Workbench ID: 138092
• ChEMBL ID: CHEMBL48132
• Mol file: 142-96-1.mol

Synonyms:dibutyl ether

Chemical Property of Dibutyl ether

Chemical Property:

• Appearance/Colour: colourless liquid with ether-like odour
• Vapor Pressure: 4.8 mm Hg ( 20 °C)
• Melting Point: -98 °C(lit.)
• Refractive Index: n20/D 1.399(lit.)
• Boiling Point: 142.1 °C at 760 mmHg
• Flash Point: 25 °C
• PSA: 9.23000
• Density: 0.78 g/cm³
• LogP: 2.60320
• Storage Temp.: Flammables area
• Solubility.: H2O: soluble0.113g/L at 20°C
• Water Solubility.: 0.03 g/100 mL (20 ºC)
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 6
• Exact Mass: 130.135765193
• Heavy Atom Count: 9
• Complexity: 37.8
• Transport DOT Label: Flammable Liquid

Purity/Quality:

98% ^*data from raw suppliers

Dibutyl Ether ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 10-36/37/38-52/53
• Safety Statements: 61-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Solvents -> Ethers (
• Canonical SMILES: CCCCOCCCC
• Inhalation Risk: No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.
• Effects of Short Term Exposure: The substance is mildly irritating to the eyes and respiratory tract. If swallowed the substance may cause vomiting and could result in aspiration pneumonitis.
• Effects of Long Term Exposure: The substance defats the skin, which may cause dryness or cracking.
• Description: Butyl ether (dibutyl ether) is a colorless, stable liquid, with a mild ether-like odor. It is immiscible with water, with a specific gravity of 0.8, which is lighter than water. Butyl ether is a moderate fire risk and will form explosive peroxides on aging. Flammable range is 1.5%–7.6% in air, with a boiling point of 286°F (141°C) and a flash point of 77°F (25°C). Ignition temperature is 382°F (194°C), and the vapor density is 4.5, which is heavier than air. In addition to flammability, butyl ether is toxic on prolonged inhalation. The four-digit UN identification number is 1149. The NFPA 704 designation is health 2, flammability 3, and reactivity 1. The primary use is as a solvent.
• Uses: Di-n-butyl ether is used as a solvent for Grignard, Witting and alkyl lithium reactions. It is also used as a solvent for oils and fats and some natural and synthetic resins. It is considered as a replacement for terathydofuran in organic synthesis due to its less water and peroxide and high boiling point. In the pharmaceutical industry, it is used in the manufacturing process of active pharmaceutical ingredient such as procarbazine and cefaclor. In addition to this, it is used as an important solvent for the application of the coating. Butyl ether is used mainly as a solvent for organic materials such as resins, oils, hydrocarbons, esters, gums, and alkaloids. It is also used as an extracting agent in metal separation, as a reacting medium in organic synthesis processes, and as a solvent in teaching, research and analytical laboratories. Solvent for hydrocarbons, fatty materials; extracting agent used especially for separating met- als, solvent purification, organic synthesis (reaction medium).

Technology Process of Dibutyl ether

There total 118 articles about Dibutyl ether which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

benzyl alcohol (100-51-6,185532-71-2) + butan-1-ol (71-36-3) → dibutyl ether (142-96-1) + benzyl 1-butyl ether (588-67-0)

Guidance literature:

With Cp*Ir(Cl)₂(nBu₂Im); silver trifluoromethanesulfonate; at 130 ℃; for 2h;

DOI:10.1002/chem.200801580

Reference yield: 78.0%

D-Fructose (57-48-7,18875-34-8) + butan-1-ol (71-36-3) → 5-(butoxymethyl)furan-2-carbaldehyde (1917-68-6) + dibutyl ether (142-96-1) + n-butyl formate (592-84-7) + butyl levulinate (2052-15-5)

Guidance literature:

With poly(p-styrenesulfonic acid)-grafted carbon nanotubes; at 120 ℃; for 24h; chemoselective reaction; Sealed tube; Green chemistry;

DOI:10.1039/c3gc41139g

Reference yield: 57.0%

butan-1-ol (71-36-3) → 1-butylene (106-98-9,9003-28-5) + (Z)-2-Butene (590-18-1) + trans-2-Butene (624-64-6) + dibutyl ether (142-96-1)

Guidance literature:

3-methyl-1-(4-sulfobutyl)imidazol-3-ium bis((trifluoromethyl)sulfonyl)azanide; at 250 ℃; for 0.5h; Product distribution / selectivity; Irradiation;

upstream raw materials:

1-bromo-butane

sodium butanolate

1-iodo-butane

butyl para-toluenesulfonate

Downstream raw materials:

6-methyl-2,3,4,5-tetrahydro-pyridine

butyl xanthic acid

p-cresol

2,3,5,6,2',6'-hexamethyl-benzophenone

Refernces

• 1、 Jansen, Susan,Palmieri, Michael,Gomez, Maria,Lawrence, Steve. "Acid catalysts based on Cu/Ru alumina: Conversion of butyraldehyde to dibutyl ether". . p. 262 - 270. Retrieved 1996.
• 2、 Démolis, Alexandre,Eternot, Marion,Essayem, Nadine,Rataboul, Franck. "Influence of butanol isomers on the reactivity of cellulose towards the synthesis of butyl levulinates catalyzed by liquid and solid acid catalysts". . p. 3747 - 3754. Retrieved 2016.
• 3、 Petrov, B. I.,Slushkov, A. M.,Kaplin, A. Yu.,Domrachev, G. A.. "SYNTHESIS OF METHYL TERT-BUTYL ETHER ON A CHROMIUM-OXIDE CATALYST". . p. 670. Retrieved 1986.
• 4、 Pines,Kobylinski. "". . p. 375. Retrieved 1970.
• 5、 Pérez,Bringué,Iborra,Tejero,Cunill. "Ion exchange resins as catalysts for the liquid-phase dehydration of 1-butanol to di-n-butyl ether". . p. 38 - 48. Retrieved 2014.
• 6、 Bagnell, Laurence,Cablewski, Teresa,Strauss, Christopher R.. "A catalytic symmetrical etherification". . p. 283 - 284. Retrieved 1999.
• 7、 Bowen, Richard D.,Suh, Dennis,Terlouw, Johan K.. "Reactions of Ionized Dibutyl Ether". . p. 791 - 805. Retrieved 1994.
• 8、 Dutta, Saikat,Kella, Tatinaidu,Mal, Sib Sankar,Shee, Debaprasad,Vennathan, Anjana Anandan. "Selective dehydration of 1-butanol to butenes over silica supported heteropolyacid catalysts: Mechanistic aspect". . . Retrieved 2021/11/03.
• 9、 Sapsford, Joshua S.,Csókás, Dániel,Turnell-Ritson, Roland C.,Parkin, Liam A.,Crawford, Andrew D.,Pápai, Imre,Ashley, Andrew E.. "Transition Metal-Free Direct Hydrogenation of Esters via a Frustrated Lewis Pair". . p. 9143 - 9150. Retrieved 2021/07/31.