142-96-1 Usage
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.
Chemical Properties
Different sources of media describe the Chemical Properties of 142-96-1 differently. You can refer to the following data:
1. Di-n-butyl ether is colourless liquid with ether-like odour
2. Di-n-butyl ether is a flammable, colorless liquid with a mild, ethereal odor.
Uses
Different sources of media describe the Uses of 142-96-1 differently. You can refer to the following data:
1. 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.
2. 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.
3. Solvent for hydrocarbons, fatty materials;
extracting agent used especially for separating met-
als, solvent purification, organic synthesis (reaction
medium).
General Description
Di-n-butyl ether is a clear colorless liquid with an ethereal odor. Flash point below 141°F. Less dense than water and insoluble in water. Vapors heavier than air. Irritates the eyes, nose, throat, and respiratory tract.
Air & Water Reactions
Highly flammable. Oxidizes readily in air to form unstable peroxides that may explode spontaneously [Bretherick 1979 p.151-154, 164]. A mixture of liquid air and diethyl ether exploded spontaneously [MCA Case History 616 1960]. Insoluble in water.
Reactivity Profile
Ethers, such as BUTYL ETHER can act as bases. They form salts with strong acids and addition complexes with Lewis acids. The complex between diethyl ether and boron trifluoride is an example. Ethers may react violently with strong oxidizing agents. In other reactions, which typically involve the breaking of the carbon-oxygen bond, ethers are relatively inert.
Hazard
Toxic on prolonged inhalation. Flammable,
moderate fire risk. May form explosive peroxides,
especially in anhydrous form.
Health Hazard
Inhalation causes irritation of nose and throat. Liquid irritates eyes and may irritate skin on prolonged contact. Ingestion causes irritation of mouth and stomach.
Fire Hazard
Behavior in Fire: Vapor is heavier than air and may travel a considerable distance to a source of ignition and flash back.
Chemical Reactivity
Reactivity with Water No reaction; Reactivity with Common Materials: No reaction; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.
Industrial uses
n-Butyl ether is used in
synthesis reactions that require an anhydrous, inert solvent. This ether is a valuable
extraction solvent for aqueous solutions because of its low water solubility. n-Butyl
ether when mixed with ethanol or butanol is an excellent solvent for ethyl cellulose.
Safety Profile
Mildly toxic by
inhalation, ingestion, and skin contact.
Human systemic effects by inhalation:
conjunctiva irritation and unspecified nasal
effects. An experimental skin and human
eye irritant. See also ETHERS. Dangerous
fire hazard when exposed to heat, flame, oroxidizers. Incompatible with NCL and
oxidizing materials. To fight fire, use alcohol
foam, dry chemical. When heated to
decomposition it emits acrid smoke and
fumes.
Potential Exposure
Di-n-butyl ether is used as a solvent for hydrocarbons, fatty materials; extracting agent in used metals separation; solvent purification, making other chemicals. Incompatibilities: May form explosive mixture with air. May accumulate static electrical charges, and may cause ignition of its vapors. Incompatible with strong acids; oxidizers. Contact with air or light may form unstable and explosive peroxides, especially anhydrous form.
Environmental Fate
Butyl ether has the ability to dissolve lipids. As a result, it
causes irritation and pain on contact with the eyes and nasal
mucosa. It also causes dermal irritation and dermatitis on
contact with the skin. Damage caused by butyl ether appears
to be scattered loss of epithelial cells due to solution of
phospholipid cell membranes. At the central nervous system
(CNS) level, butyl ether, like other volatile organic solvents,
depresses the CNS by dissolving in the lipid membrane of the
cells and disrupting the lipid matrix. These effects are known
as membrane fluidization. At the molecular level, membrane
fluidization disrupts solute gradient homeostasis, which is
essential for cell function.
Shipping
UN1149 Butyl ethers & Dibutyl ethers, Hazard
Class: 3; Labels: 3—Flammable liquid
Purification Methods
Peroxides (detected by the liberation of iodine from weakly acid HCl solutions of 2% KI) can be removed by shaking 1L of ether with 5-10mL of a solution comprising of 6.0g of ferrous sulfate and 6mL conc H2SO4 and 110mL of water, with aqueous Na2SO3, or with acidified NaI, water, then aqueous Na2S2O3. After washing with dilute NaOH, KOH, or Na2CO3, then water, the ether is dried with CaCl2 and distilled. It can be further dried by distillation from CaH2 or Na (after drying with P2O5), and stored in the dark with Na or NaH. The ether can also be purified by treating with CS2 and NaOH, expelling the excess sulfide by heating. The ether is then washed with water, dried with NaOH and distilled [Kusama & Koike J Chem Soc Jpn, Pure Chem Sect 72 229 1951]. Other purification procedures include passage through an activated alumina column to remove peroxides, or through a column of silica gel, and distillation after adding about 3% (v/v) of a 1M solution of MeMgI in n-butyl ether. [Beilstein 1 IV 1520.]
Toxicity evaluation
Production of butyl ether and its use as an extracting agent
and a solvent may result in its release to the environment
through various waste streams. If released to air, a vapor
pressure of 6.0 mmHg at 25°C indicates that butyl ether will
exist solely as a vapor in the ambient atmosphere. Vaporphase
butyl ether reacts in the atmosphere with hydroxyl
radicals; the half-life for this reaction in air has been estimated
to be 13 h. Direct photolysis is not expected to be an
important removal process since aliphatic ethers do not
absorb light in the environmental spectrum. If released to
soil, butyl ether is expected to have high mobility based on
its estimated adsorption coefficient (Koc) of 51. Volatilization
from moist soil surfaces may be an important fate process
based on its reported Henry’s law constant of
6.0×10-3 atm m3 mol-1. Butyl ether is expected to volatilize
from dry soil surfaces based on its reported vapor
pressure. If released into water, butyl ether is not expected to
adsorb to suspended solids and sediment in water based on
its Koc. Aqueous screening studies indicate biodegradation
may be an important fate process in both soil and water; for
example, butyl ether reached 3–4% of its theoretical biological
oxygen demand (BOD) over 4 weeks using an activated
sludge seed. Volatilization from water surfaces is
expected to occur based on this compound’s estimated
Henry’s law constant. Estimated volatilization half-lives for
a model river and model lake have been reported to be 3.5 h
and 4.6 days, respectively. Bioconcentration factors (BCFs)
ranging from 30 to 114 in carp suggest that bioconcentration
in aquatic organisms is moderate to high. Butyl ether is not
expected to undergo hydrolysis in the environment due to
the lack of hydrolyzable functional groups.
Waste Disposal
Dissolve or mix the material
with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. All federal,
state, and local environmental regulations must be
observed.
Check Digit Verification of cas no
The CAS Registry Mumber 142-96-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,4 and 2 respectively; the second part has 2 digits, 9 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 142-96:
(5*1)+(4*4)+(3*2)+(2*9)+(1*6)=51
51 % 10 = 1
So 142-96-1 is a valid CAS Registry Number.
InChI:InChI=1/C8H18O/c1-3-5-7-9-8-6-4-2/h3-8H2,1-2H3
142-96-1Relevant articles and documents
Hudson,Mc Adoo
, p. 109,111, 113 (1979)
Etherification of n-butanol to di-n-butyl ether over Keggin-, wells-Dawson-, and preyssler-type heteropolyacid catalysts
Kim, Jeong Kwon,Choi, Jung Ho,Park, Dong Ryul,Song, In Kyu
, p. 8121 - 8126 (2013)
Etherification of n-butanol to di-n-butyl ether was carried out over various structural classes of heteropolyacid (HPA) catalysts, including Keggin- (H3PW12O40), Wells-Dawson- (H6P2W18O62), and Preyssler-type (H14[NaP5W30O110]) HPA catalysts. Successful formation of HPA catalysts was well confirmed by FT-IR, 31P NMR, and ICP-AES analyses. Acid properties of HPA catalysts were determined by NH3-TPD (temperature-programmed desorption) measurements. Acid strength of the catalysts increased in the order of H14 [NaP5W30O110] 6P2W18O62 3PW12O40. The catalytic performance of HPA catalysts was closely related to the acid strength of the catalysts. In the etherification of n-butanol to di-n-butyl ether over various structural classes of HPA catalysts, Conversion of n-butanol and yield for di-n-butyl ether increased with increasing acid strength of HPA catalysts. Among the catalysts tested, Keggin-type (H3PW12O40) HPA catalyst with the strongest acid strength showed the best catalytic performance. Acid strength of HPAs served as an important factor determining the catalytic performance in the etherification of n-butanol to di-n-butyl ether. Copyright
Etherification of n-butanol to di-n-butyl ether over HnXW 12O40 (XCo2+, B3+, Si4+, and P5+) Keggin heteropolyacid catalysts
Kim, Jeong Kwon,Choi, Jung Ho,Song, Ji Hwan,Yi, Jongheop,Song, In Kyu
, p. 5 - 8 (2012)
Etherification of n-butanol to di-n-butyl ether was carried out over heteroatom-substituted HnXW12O40 (XCo 2+, B3+, Si4+, and P5+) Keggin heteropolyacid (HPA) catalysts. Acid properties of HPA catalysts were determined by NH3-TPD measurements. Acid strength of HnXW 12O40 Keggin HPA catalysts increased in the order of H6CoW12O40 5BW 12O40 4SiW12O40 3PW12O40. Yield for di-n-butyl ether increased with increasing acid strength of the catalysts. Acid strength of HPAs served as an important factor determining the catalytic performance in the etherification of n-butanol to di-n-butyl ether.
Kobylinski,Pines
, p. 384 (1970)
AQUIVION perfluorosulfonic acid resin for butyl levulinate production from furfuryl alcohol
Bernal, Hilda Gómez,Oldani, Claudio,Funaioli, Tiziana,Raspolli Galletti, Anna Maria
, p. 14694 - 14700 (2019)
This study reports the sustainable production of butyl levulinate (BL) from furfuryl alcohol (FA), a highly abundant biomass derived platform obtained from C5 sugars in hemicellulose. FA upgrading is performed adopting a robust and easily recyclable commercial perfluorosulfonic acid resin, Aquivion P87S, used as cylinder shaped pellets. This approach avoids the use of corrosive and harmful mineral acids allowing a simple separation of the catalyst from the reaction mixture, reducing the cost of equipment materials and disposal or neutralization issues, also resulting in reduced solvent dehydration. Moreover, FA alcoholysis to BL involves butanol as a sustainable reaction medium, also readily obtained from biomass. The catalyst remains stable up to 6 recycles. Furthermore, the absence of heavy by-products and the stability of the catalyst allowed us to perform successive additions of the substrate to the reaction medium to increase the BL concentrations up to 0.66 M (13 wt%).
Polymer-supported catalysts for clean preparation of n-butanol
Jiang, Haibin,Lu, Shuliang,Zhang, Xiaohong,Peng, Hui,Dai, Wei,Qiao, Jinliang
, p. 2499 - 2503 (2014)
A new type of RANEY metal catalyst supported by polymer was developed for the clean preparation of n-butanol. Unlike traditional supported catalysts, the newly developed alkalescent polyamide 6 (PA6) supported RANEY nickel catalyst provided a 100.0% conversion of n-butyraldehyde without producing any detectable n-butyl ether, the main byproduct in industry. The significantly enhanced catalyst selectivity of the polymer-supported RANEY metal catalyst was attributed to the elimination of the acid-catalyzed side reaction associated with RANEY metals and traditional catalyst supports, such as Al2O3 and SiO2. By eliminating acid-catalyzed side reactions, therefore, green chemistry could be achieved through reducing resources and energy consumption in chemical reactions. Furthermore, the preparation and recycling of the polymer-supported catalysts are also much more eco-friendly than for traditional Al2O3-/SiO 2-supported catalysts. The methodology developed in this study to use alkalescent polymers as the catalyst support could be applied to the whole catalyst family, including a series of important RANEY metal catalysts (e.g., RANEY nickel, RANEY cobalt, RANEY copper) used routinely in the chemical industry.
The Guanidine-Promoted Direct Synthesis of Open-Chained Carbonates
Shang, Yuhan,Zheng, Mai,Zhang, Haibo,Zhou, Xiaohai
, p. 933 - 938 (2019)
In order to reduce CO2 accumulation in the atmosphere, chemical fixation methodologies were developed and proved to be promising. In general, CO2 was turned into cyclic carbonates by cycloaddition with epoxides. However, the cyclic carbonates need to be converted into open-chained carbonates by transesterification for industrial usage, which results in wasted energy and materials. Herein, we report a process catalyzed by tetramethylguanidine (TMG) to afford linear carbonates directly. This process is greener and shows potential for industrial applications.
Silver(I)-Catalyzed Reductive Cross-Coupling of Aldehydes to Structurally Diverse Cyclic and Acyclic Ethers
Dong, Guichao,Li, Chuang,Liang, Ting,Xu, Xin,Xu, Zhou
supporting information, p. 1817 - 1821 (2022/03/16)
A range of medium-sized cyclic ethers (5 to 11 membered) have been effectively synthesized through intramolecular reductive coupling of dialdehydes initiated by 50 ppm to 0.5% of AgNTf2 with hydrosilane at 25 °C. The catalytic system is also suitable for the coupling of two different monoaldehydes to provide unsymmetrical ethers. This protocol features broad functional group compatibility, high product diversity, high efficiency, and utility in the late-stage modification of complex biorelevant molecules.
Transition Metal-Free Direct Hydrogenation of Esters via a Frustrated Lewis Pair
Sapsford, Joshua S.,Csókás, Dániel,Turnell-Ritson, Roland C.,Parkin, Liam A.,Crawford, Andrew D.,Pápai, Imre,Ashley, Andrew E.
, p. 9143 - 9150 (2021/07/31)
"Frustrated Lewis pairs"(FLPs) continue to exhibit unique reactivity for the reduction of organic substrates, yet to date, the catalytic hydrogenation of an ester functionality has not been demonstrated. Here, we report that iPr3SnNTf2 (1-NTf2; Tf = SO2CF3) is a more potent Lewis acid than the previously studied iPr3SnOTf; in an FLP with 2,4,6-collidine/2,6-lutidine (col/lut), this translates to faster H2 activation and the catalytic hydrogenolysis of an ester bond by a main-group compound, furnishing alcohol and ether (minor) products. The reaction outcome is sensitive to the steric and electronic properties of the substrate; CF3CO2Et and simple formates (HCO2Me and HCO2Et) are catalytically reduced, whereas related esters CF3CO2nBu and CH3CO2Et show only stoichiometric reactivity. A computational case study on the hydrogenation of CF3CO2Et and CH3CO2Et reveals that both share a common mechanistic pathway; however, key differences in the energies of a Sn-acetal intermediate and transition states emerge, favoring CF3CO2Et reduction. The alcohol products reversibly inhibit 1-NTf2/lut via formation of resting-state species 1-OR/[1·(1-OR)]+[NTf2]- however, the extra energy required to regenerate 1-NTf2/lut exacerbates the unfavorable reduction energy profile for CH3CO2Et, ultimately preventing turnover. These findings will assist the design of future main-group catalysts for ester hydrogenation, with improved performance.
SATURATED HOMOETHER MANUFACTURING METHOD FROM UNSATURATED CARBONYL COMPOUND
-
Paragraph 0045-0046, (2020/05/14)
PROBLEM TO BE SOLVED: To provide a method for manufacturing saturated homoether from an unsaturated carboxyl compound at good efficiency. SOLUTION: There is provided a manufacturing method of saturated homoether using an unsaturated carboxyl compound and hydrogen as raw materials, and a catalyst in which a metal is carried on an acidic catalyst carrier. The metal of the catalyst is for example palladium, and the carrier of the catalyst is alumina, silica, silica-alumina, or the like. The unsaturated carbonyl compound as the raw material is 2-butenal, 2-ethyl-2-hexenal, 2-ethyl-2-butenal, 2-hexenal, and manufactured saturated homoether is dibuthylether, bis(2-ethylhexyl)ether, bis(2-ethylbuty)ether, dihexylether, or the like. SELECTED DRAWING: None COPYRIGHT: (C)2020,JPO&INPIT
