Diisopropyl ether

Last updated
Diisopropyl ether
Diisopropyl ether.svg
Names
Preferred IUPAC name
2-[(Propan-2-yl)oxy]propane
Other names
Isopropyl ether
2-Isopropoxypropane
Diisopropyl oxide
DIPE
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.003.237 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 203-560-6
PubChem CID
RTECS number
  • TZ5425000
UNII
UN number 1159
  • InChI=1S/C6H14O/c1-5(2)7-6(3)4/h5-6H,1-4H3 Yes check.svgY
    Key: ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C6H14O/c1-5(2)7-6(3)4/h5-6H,1-4H3
    Key: ZAFNJMIOTHYJRJ-UHFFFAOYAC
  • O(C(C)C)C(C)C
Properties
C6H14O
Molar mass 102.177 g·mol−1
AppearanceColorless liquid
Odor Sharp, sweet, ether-like [1]
Density 0.725 g/ml
Melting point −60 °C (−76 °F; 213 K)
Boiling point 68.5 °C (155.3 °F; 341.6 K)
2 g/L at 20 °C
Vapor pressure 119 mmHg (20°C) [1]
-79.4·10−6 cm3/mol
Hazards
GHS labelling:
GHS-pictogram-flamme.svg GHS-pictogram-exclam.svg GHS-pictogram-silhouette.svg
Danger
H225, H316, H319, H335, H336, H361, H371, H412
P201, P202, P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P273, P280, P281, P303+P361+P353, P304+P340, P305+P351+P338, P308+P313, P309+P311, P312, P332+P313, P337+P313, P370+P378, P403+P233, P403+P235, P405, P501
NFPA 704 (fire diamond)
NFPA 704.svgHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
1
3
1
Flash point −28 °C (−18 °F; 245 K)
443 °C (829 °F; 716 K)
Explosive limits 1.4–7.9%
Lethal dose or concentration (LD, LC):
8470 mg/kg (rat, oral) [2]
5000-6500 mg/kg (rabbit, oral) [2]
38,138 ppm (rat)
30,840 ppm (rabbit)
28,486 ppm (rabbit) [2]
NIOSH (US health exposure limits):
PEL (Permissible)
TWA 500 ppm (2100 mg/m3) [1]
REL (Recommended)
TWA 500 ppm (2100 mg/m3) [1]
IDLH (Immediate danger)
1400 ppm [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Diisopropyl ether is a secondary ether that is used as a solvent. It is a colorless liquid that is slightly soluble in water, but miscible with organic solvents. It is used as an extractant and an oxygenate gasoline additive. It is obtained industrially as a byproduct in the production of isopropanol by hydration of propylene. [3] Diisopropyl ether is sometimes represented by the abbreviation DIPE.

Contents

Uses

Whereas at 20 °C, diethyl ether will dissolve 1% by weight water, diisopropyl ether dissolves 0.88%. Diisopropyl ether is used as a specialized solvent to remove or extract polar organic compounds from aqueous solutions, e.g. phenols, ethanol, acetic acid. It has also been used as an antiknock agent.

In the laboratory, diisopropyl ether is useful for recrystallizations because it has a wide liquid range. [4] [5] Diisopropyl ether is used for converting bromoboranes, which are thermally labile, into isopropoxy derivatives. [6]

Safety

Diisopropyl ether forms explosive peroxides upon standing in air. This reaction proceeds more easily than for ethyl ether due to the increased lability of the C-H bond adjacent to oxygen. Many explosions have been known to occur during handling or processing of old diisopropyl ether. [7] Some laboratory procedures recommend use of freshly opened bottles. [4] Antioxidants can be used to prevent this process. The stored solvent is generally tested for the presence of peroxides. It is recommended once every 3 months for diisopropyl ether compared to once every 12 months for ethyl ether. [8] Peroxides may be removed by shaking the ether with an aqueous solution of iron(II) sulfate or sodium metabisulfite. [9] [10] For safety reasons, methyl tert-butyl ether is often used as an alternative solvent.

See also

Related Research Articles

Methyl <i>tert</i>-butyl ether Chemical compound

Methyl tert-butyl ether (MTBE), also known as methyl tert-butyl ether and tert-butyl methyl ether, is an organic compound with a structural formula (CH3)3COCH3. MTBE is a volatile, flammable, and colorless liquid that is sparingly soluble in water. Primarily used as a fuel additive, MTBE is blended into gasoline to increase its octane rating and knock resistance, and reduce unwanted emissions.

<span class="mw-page-title-main">Ethanethiol</span> Chemical compound

Ethanethiol, commonly known as ethyl mercaptan, is an organosulfur compound with the formula CH3CH2SH. is a colorless liquid with a distinct odor. Abbreviated EtSH, it consists of an ethyl group (Et), CH3CH2, attached to a thiol group, SH. Its structure parallels that of ethanol, but with sulfur in place of oxygen. The odor of EtSH is infamous. Ethanethiol is more volatile than ethanol due to a diminished ability to engage in hydrogen bonding. Ethanethiol is toxic in high concentrations. It occurs naturally as a minor component of petroleum, and may be added to otherwise odorless gaseous products such as liquefied petroleum gas (LPG) to help warn of gas leaks. At these concentrations, ethanethiol is not harmful.

<span class="mw-page-title-main">Diazomethane</span> Simplest diazo compound and methylating agent

Diazomethane is an organic chemical compound with the formula CH2N2, discovered by German chemist Hans von Pechmann in 1894. It is the simplest diazo compound. In the pure form at room temperature, it is an extremely sensitive explosive yellow gas; thus, it is almost universally used as a solution in diethyl ether. The compound is a popular methylating agent in the laboratory, but it is too hazardous to be employed on an industrial scale without special precautions. Use of diazomethane has been significantly reduced by the introduction of the safer and equivalent reagent trimethylsilyldiazomethane.

Cyclohexene is a hydrocarbon with the formula C6H10. This cycloalkene is a colorless liquid with a sharp smell. It is an intermediate in various industrial processes. Cyclohexene is not very stable upon long term storage with exposure to light and air because it forms peroxides.

<span class="mw-page-title-main">Ethyl acetate</span> Organic compound (CH₃CO₂CH₂CH₃)

Ethyl acetate is the organic compound with the formula CH3CO2CH2CH3, simplified to C4H8O2. This colorless liquid has a characteristic sweet smell and is used in glues, nail polish removers, and in the decaffeination process of tea and coffee. Ethyl acetate is the ester of ethanol and acetic acid; it is manufactured on a large scale for use as a solvent.

<span class="mw-page-title-main">2-Butanol</span> Secondary alcohol

Butan-2-ol, or sec-butanol, is an organic compound with formula CH3CH(OH)CH2CH3. Its structural isomers are 1-butanol, isobutanol, and tert-butanol. 2-Butanol is chiral and thus can be obtained as either of two stereoisomers designated as (R)-(−)-butan-2-ol and (S)-(+)-butan-2-ol. It is normally encountered as a 1:1 mixture of the two stereoisomers — a racemic mixture.

<i>tert</i>-Butyl alcohol Chemical compound

tert-Butyl alcohol is the simplest tertiary alcohol, with a formula of (CH3)3COH (sometimes represented as t-BuOH). Its isomers are 1-butanol, isobutanol, and butan-2-ol. tert-Butyl alcohol is a colorless solid, which melts near room temperature and has a camphor-like odor. It is miscible with water, ethanol and diethyl ether.

Oxygenated chemical compounds are hydrocarbons which contain at least one oxygen atom as a part of their chemical structure. The term often refers to oxygenated chemical compounds added to fuels. Oxygenates are usually employed as gasoline additives to reduce carbon monoxide and soot that is created during the burning of the fuel. Compounds related to soot, such as polyaromatic hydrocarbons (PAHs) and nitrated PAHs, are also reduced.

<span class="mw-page-title-main">Methyl isobutyl ketone</span> Chemical compound

Methyl isobutyl ketone (MIBK) is the common name for the organic compound 4-methylpentan-2-one, condensed chemical formula (CH3)2CHCH2C(O)CH3. This colourless liquid, a ketone, is used as a solvent for gums, resins, paints, varnishes, lacquers, and nitrocellulose.

<span class="mw-page-title-main">Knorr pyrrole synthesis</span> Chemical reaction

The Knorr pyrrole synthesis is a widely used chemical reaction that synthesizes substituted pyrroles (3). The method involves the reaction of an α-amino-ketone (1) and a compound containing an electron-withdrawing group α to a carbonyl group (2).

<span class="mw-page-title-main">Thiophenol</span> Chemical compound

Thiophenol is an organosulfur compound with the formula C6H5SH, sometimes abbreviated as PhSH. This foul-smelling colorless liquid is the simplest aromatic thiol. The chemical structures of thiophenol and its derivatives are analogous to phenols. An exception is the oxygen atom in the hydroxyl group (-OH) bonded to the aromatic ring is replaced by a sulfur atom. The prefix thio- implies a sulfur-containing compound and when used before a root word name for a compound which would normally contain an oxygen atom, in the case of 'thiol' that the alcohol oxygen atom is replaced by a sulfur atom.

<i>tert</i>-Butyllithium Chemical compound

tert-Butyllithium is a chemical compound with the formula (CH3)3CLi. As an organolithium compound, it has applications in organic synthesis since it is a strong base, capable of deprotonating many carbon molecules, including benzene. tert-Butyllithium is available commercially as hydrocarbon solutions; it is not usually prepared in the laboratory.

<span class="mw-page-title-main">Dimethoxymethane</span> Chemical compound

Dimethoxymethane, also called methylal, is a colorless flammable liquid with a low boiling point, low viscosity and excellent dissolving power. It has a chloroform-like odor and a pungent taste. It is the dimethyl acetal of formaldehyde. Dimethoxymethane is soluble in three parts water and miscible with most common organic solvents.

Diisopropylamine is a secondary amine with the chemical formula (Me2CH)2NH (Me = methyl). Diisopropylamine is a colorless liquid with an ammonia-like odor. Its lithium derivative, lithium diisopropylamide, known as LDA is a widely used reagent.

<span class="mw-page-title-main">Vinyl bromide</span> Chemical compound

Vinyl bromide is a simple vinyl halide. It is a colorless liquid. It is produced from ethylene dibromide. It is mainly used as a comonomer to confer fire retardant properties to acrylate polymers.

<span class="mw-page-title-main">Chloromethyl methyl ether</span> Chemical compound

Chloromethyl methyl ether (CMME) is a compound with formula CH3OCH2Cl. A colorless liquid, it is a chloroalkyl ether. It is used as an alkylating agent. In organic synthesis, it is used for introducing the methoxymethyl ether (MOM) protecting group, and is thus often called MOM-Cl or MOM chloride. It also finds application as a chloromethylating agent in some variants of the Blanc chloromethylation.

Isopropyl alcohol is a colorless, flammable organic compound with a pungent alcoholic odor. As an isopropyl group linked to a hydroxyl group it is the simplest example of a secondary alcohol, where the alcohol carbon atom is attached to two other carbon atoms. It is a structural isomer of propan-1-ol and ethyl methyl ether. They all have the formula C3H8O.

tert-Amyl methyl ether (TAME) is an ether used as a fuel oxygenate. TAME derives from C5 distillation fractions of naphtha. It has an ethereous odor. Unlike most ethers, it does not require a stabilizer as it does not form peroxides on storage.

<span class="mw-page-title-main">Diethylphosphite</span> Chemical compound

Diethyl phosphite is the organophosphorus compound with the formula (C2H5O)2P(O)H. It is a popular reagent for generating other organophosphorus compounds, exploiting the high reactivity of the P-H bond. Diethyl phosphite is a colorless liquid. The molecule is tetrahedral.

References

  1. 1 2 3 4 5 NIOSH Pocket Guide to Chemical Hazards. "#0362". National Institute for Occupational Safety and Health (NIOSH).
  2. 1 2 3 "Isopropyl ether". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  3. ↑ Sakuth, Michael; Mensing, Thomas; Schuler, Joachim; Heitmann, Wilhelm; Strehlke, Günther; Mayer (2010). "Ethers, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a10_023.pub2.
  4. 1 2 Andrea Goti; Francesca Cardona; Gianluca Soldaini (2005). "Methyltrioxorhenium Catalyzed Oxidation of Secondary Amines to Nitrones: N-Benzylidene-Benzylamine N-Oxide". Organic Syntheses. 81: 204. doi: 10.15227/orgsyn.081.0204 .
  5. ↑ Ferenc Merényi, Martin Nilsson (1972). "2-Acetyl-1,3-Cyclopentanedione". Organic Syntheses. 52: 1. doi:10.15227/orgsyn.052.0001.
  6. ↑ Shoji Hara, Akira Suzuk (1998). "Synthesis of 4-(2-Bromo-2-Propenyl)-4-Methyl-Y-Butyrolactone by the Reaction of Ethyl Levulinate with (2-Bromoallyl)Diisopropoxyborane Prepared by Haloboration of Allene". Organic Syntheses. 75: 129. doi:10.15227/orgsyn.075.0129.
  7. ↑ Matyáš, Robert; Pachman, Jiří. (2013). Primary explosives. Berlin: Springer. p. 272. ISBN   978-3-642-28436-6. OCLC   832350093.
  8. ↑ "Organic Peroxides - Hazards : OSH Answers". www.ccohs.ca. Canadian Centre for Occupational Health and Safety, Government of Canada.
  9. ↑ Chai, Christina Li Lin; Armarego, W. L. F. (2003). Purification of laboratory chemicals. Oxford: Butterworth-Heinemann. p. 176. ISBN   978-0-7506-7571-0.
  10. ↑ Hamstead, A. C. (1964). "Destroying Peroxides of Isopropyl Ether". Industrial and Engineering Chemistry. 56 (6): 37-42. doi:10.1021/ie50654a005.
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