Di-n-propyl ether

Last updated
Di-n-propyl ether
Di-n-propylether Structural Formulae.svg
Names
Preferred IUPAC name
1-Propoxypropane
Other names
Propyl ether, di-
Dipropyl ether, normal isomer
Di-n-propyl ether
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.003.518 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C6H14O/c1-3-5-7-6-4-2/h3-6H2,1-2H3
    Key: POLCUAVZOMRGSN-UHFFFAOYSA-N
  • InChI=1/C6H14O/c1-3-5-7-6-4-2/h3-6H2,1-2H3
    Key: POLCUAVZOMRGSN-UHFFFAOYAT
  • O(CCC)CCC
Properties
C6H14O
Molar mass 102.177 g·mol−1
AppearanceColorless liquid
Density 0.75 g/cm3 [1]
Melting point −122 °C (−188 °F; 151 K) [1]
Boiling point 90 °C (194 °F; 363 K) [1]
3 g/L (20 °C)
Hazards
NFPA 704 (fire diamond)
1
3
1
Flash point −18 °C (0 °F; 255 K) [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Dipropyl ether is the symmetrical ether of two n-propyl groups. It is a colorless, flammable liquid with a sweet odor typical of ethers.

Contents

Preparation

Acid catalyzed ether synthesis

Dipropyl ether can be synthesized by reacting two molecules of n-propanol in the presence of p-toluenesulfonic acid (a strong acid) and heat, in the same way other symmetrical ethers may be formed. [2]

Williamson ether synthesis

This ether may also be prepared by way of the Williamson ether synthesis in which n-propoxide, the conjugate base of n-propanol, is reacted with an n-propyl halide: [3]

Williamson ether synthesis of dipropyl ether.png

Safety

As is typical of ethers, dipropyl ether may slowly form explosive organic peroxides over long periods in storage. [2] Antioxidants such as butylated hydroxytoluene are often added to ethers to prevent this process. [4]

Due to the shock and light sensitive nature of organic peroxides, dipropyl ether should never be boiled or evaporated to dryness. This concentrates peroxides that may be present, which can then detonate unexpectedly destroying the vessel in which they have deposited or igniting nearby flammable liquids. [5]

See also

Related Research Articles

Ether Class of organic compounds

Ethers are a class of organic compounds that contain an ether group—an oxygen atom connected to two alkyl or aryl groups. They have the general formula R–O–R′, where R and R′ represent the alkyl or aryl groups. Ethers can again be classified into two varieties: if the alkyl groups are the same on both sides of the oxygen atom, then it is a simple or symmetrical ether, whereas if they are different, the ethers are called mixed or unsymmetrical ethers. A typical example of the first group is the solvent and anaesthetic diethyl ether, commonly referred to simply as "ether" (CH3–CH2–O–CH2–CH3). Ethers are common in organic chemistry and even more prevalent in biochemistry, as they are common linkages in carbohydrates and lignin.

Solvent Substance dissolving a solute resulting in a solution

A solvent is a substance that dissolves a solute, resulting in a solution. A solvent is usually a liquid but can also be a solid, a gas, or a supercritical fluid. Water is a solvent for polar molecules and the most common solvent used by living things; all the ions and proteins in a cell are dissolved in water within the cell.

Tetrahydrofuran Chemical compound

Tetrahydrofuran (THF), or oxolane, is an organic compound with the formula (CH2)4O. The compound is classified as heterocyclic compound, specifically a cyclic ether. It is a colorless, water-miscible organic liquid with low viscosity. It is mainly used as a precursor to polymers. Being polar and having a wide liquid range, THF is a versatile solvent.

Propylene oxide Chemical compound

Propylene oxide is an organic compound with the molecular formula CH3CHCH2O. This colourless volatile liquid with an odour resembling ether, is produced on a large scale industrially. Its major application is its use for the production of polyether polyols for use in making polyurethane plastics. It is a chiral epoxide, although it is commonly used as a racemic mixture.

Diethyl ether Organic chemical compound

Diethyl ether, or simply ether, is an organic compound in the ether class with the formula (C
2
H
5
)
2
O
, sometimes abbreviated as Et
2
O
. It is a colorless, highly volatile, sweet-smelling, extremely flammable liquid. It is commonly used as a solvent in laboratories and as a starting fluid for some engines. It was formerly used as a general anesthetic, until non-flammable drugs were developed, such as halothane. It has been used as a recreational drug to cause intoxication. It is a structural isomer of butanol.

Acrylic acid Chemical compound

Acrylic acid (IUPAC: propenoic acid) is an organic compound with the formula CH2=CHCOOH. It is the simplest unsaturated carboxylic acid, consisting of a vinyl group connected directly to a carboxylic acid terminus. This colorless liquid has a characteristic acrid or tart smell. It is miscible with water, alcohols, ethers, and chloroform. More than a million tons are produced annually.

Diisopropyl ether Chemical compound

Diisopropyl ether is 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. Diisopropyl ether is sometimes represented by the abbreviation DIPE.

2-Butanol Secondary alcohol

2-Butanol, or sec-butanol, is an organic compound with formula CH3CH(OH)CH2CH3. This secondary alcohol is a flammable, colorless liquid that is soluble in three parts water and completely miscible with organic solvents. It is produced on a large scale, primarily as a precursor to the industrial solvent methyl ethyl ketone. 2-Butanol is chiral and thus can be obtained as either of two stereoisomers designated as (R)-(−)-2-butanol and (S)-(+)-2-butanol. It is normally encountered as a 1:1 mixture of the two stereoisomers — a racemic mixture.

Isobutanol Chemical compound

Isobutanol (IUPAC nomenclature: 2-methylpropan-1-ol) is an organic compound with the formula (CH3)2CHCH2OH (sometimes represented as i-BuOH). This colorless, flammable liquid with a characteristic smell is mainly used as a solvent either directly or as its esters. Its isomers, the other butanols, include n-butanol, 2-butanol, and tert-butanol, all of which are important industrially.

Allyl alcohol Chemical compound

Allyl alcohol (IUPAC name: prop-2-en-1-ol) is an organic compound with the structural formula CH2=CHCH2OH. Like many alcohols, it is a water-soluble, colourless liquid. It is more toxic than typical small alcohols. Allyl alcohol is used as a raw material for the production of glycerol, but is also used as a precursor to many specialized compounds such as flame-resistant materials, drying oils, and plasticizers. Allyl alcohol is the smallest representative of the allylic alcohols.

Propyl acetate Chemical compound

Propyl acetate, also known as propyl ethanoate, is a chemical compound used as a solvent and an example of an ester. This clear, colorless liquid is known by its characteristic odor of pears. Due to this fact, it is commonly used in fragrances and as a flavor additive. It is formed by the esterification of acetic acid and 1-propanol, often via Fischer–Speier esterification, with sulfuric acid as a catalyst and water produced as a byproduct.

Cumene Chemical compound

Cumene (isopropylbenzene) is an organic compound that is based on an aromatic hydrocarbon with an aliphatic substitution. It is a constituent of crude oil and refined fuels. It is a flammable colorless liquid that has a boiling point of 152 °C. Nearly all the cumene that is produced as a pure compound on an industrial scale is converted to cumene hydroperoxide, which is an intermediate in the synthesis of other industrially important chemicals, primarily phenol and acetone.

Dibutyl ether is a chemical compound belonging to the ether family with the molecular formula of C
8
H
18
O
. It is colorless, volatile, and flammable liquid and has peculiar ethereal smell.

1-Propanol Primary alcohol compound

1-Propanol is a primary alcohol with the formula CH
3
CH
2
CH
2
OH
and sometimes represented as PrOH or n-PrOH. It is a colorless liquid and an isomer of 2-propanol. It is formed naturally in small amounts during many fermentation processes and used as a solvent in the pharmaceutical industry, mainly for resins and cellulose esters, and, sometimes, as a disinfecting agent.

Benzyl chloride, or α-chlorotoluene, is an organic compound with the formula C6H5CH2Cl. This colorless liquid is a reactive organochlorine compound that is a widely used chemical building block.

Isopropyl acetate Chemical compound

Isopropyl acetate is an ester, an organic compound which is the product of esterification of acetic acid and isopropanol. It is a clear, colorless liquid with a characteristic fruity odor.

Dimethoxymethane 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.

Propargyl alcohol Chemical compound

Propargyl alcohol, or 2-propyn-1-ol, is an organic compound with the formula C3H4O. It is the simplest stable alcohol containing an alkyne functional group. Propargyl alcohol is a colorless viscous liquid that is miscible with water and most polar organic solvents.

1-Bromopropane Chemical compound

1-Bromopropane (n-propylbromide or nPB) is an organobromine compound with the chemical formula CH3CH2CH2Br. It is a colorless liquid that is used as a solvent. It has a characteristic hydrocarbon odor. Its industrial applications increased dramatically in the 21st century.

Isopropyl alcohol (IUPAC name propan-2-ol and also called isopropanol or 2-propanol) is a colorless, flammable chemical compound (chemical formula CH3CHOHCH3) with a strong 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 1-propanol and ethyl methyl ether.

References

  1. 1 2 3 4 Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  2. 1 2 O'Neil, Maryadele; Heckelman, Patricia; Koch, Cherie; Roman, Kristin, eds. (2006). Merck Index of Chemicals and Drugs (14th ed.). Merck Research Laboratories. ISBN   978-0-911910-00-1.
  3. Fox, Marye; Whitesell, James (2004). Organic Chemistry, 3rd ed. Jones & Bartlett Publishers. ISBN   978-0763735869.
  4. "Diethyl ether product listing". Sigma-Aldrich . Retrieved 2012-07-03.
  5. "Organic peroxide hazards". Canadian Centre for Occupational Health and Safety . Retrieved 2012-07-03.