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Ether

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Ether

In organic chemistry, ethers are a class of compounds that contain an ether group, a single oxygen atom bonded to two separate carbon atoms, each part of an organyl group (e.g., alkyl or aryl). They have the general formula R−O−R′, where R and R′ represent the organyl groups. Ethers can again be classified into two varieties: if the organyl 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.

Tables

Aliphatic polyethers · Nomenclature › Polyethers
Paraformaldehyde
Paraformaldehyde
Name of the polymers with low to medium molar mass
Paraformaldehyde
Name of the polymers with high molar mass
Polyoxymethylene (POM) or polyacetal or polyformaldehyde
Preparation
Step-growth polymerisation of formaldehyde
Repeating unit
–CH2O–
Examples of trade names
Delrin from DuPont
Polyethylene glycol (PEG)
Polyethylene glycol (PEG)
Name of the polymers with low to medium molar mass
Polyethylene glycol (PEG)
Name of the polymers with high molar mass
Polyethylene oxide (PEO) or polyoxyethylene (POE)
Preparation
Ring-opening polymerization of ethylene oxide
Repeating unit
–CH2CH2O–
Examples of trade names
Carbowax from Dow
Polypropylene glycol (PPG)
Polypropylene glycol (PPG)
Name of the polymers with low to medium molar mass
Polypropylene glycol (PPG)
Name of the polymers with high molar mass
Polypropylene oxide (PPOX) or polyoxypropylene (POP)
Preparation
anionic ring-opening polymerization of propylene oxide
Repeating unit
–CH2CH(CH3)O–
Examples of trade names
Arcol from Covestro
Polytetramethylene glycol (PTMG) or Polytetramethylene ether glycol (PTMEG)
Polytetramethylene glycol (PTMG) or Polytetramethylene ether glycol (PTMEG)
Name of the polymers with low to medium molar mass
Polytetramethylene glycol (PTMG) or Polytetramethylene ether glycol (PTMEG)
Name of the polymers with high molar mass
Polytetrahydrofuran (PTHF)
Preparation
Acid-catalyzed ring-opening polymerization of tetrahydrofuran
Repeating unit
−CH2CH2CH2CH2O−
Examples of trade names
Terathane from Invista and PolyTHF from BASF
Name of the polymers with low to medium molar mass
Name of the polymers with high molar mass
Preparation
Repeating unit
Examples of trade names
Paraformaldehyde
Polyoxymethylene (POM) or polyacetal or polyformaldehyde
Step-growth polymerisation of formaldehyde
–CH2O–
Delrin from DuPont
Polyethylene glycol (PEG)
Polyethylene oxide (PEO) or polyoxyethylene (POE)
Ring-opening polymerization of ethylene oxide
–CH2CH2O–
Carbowax from Dow
Polypropylene glycol (PPG)
Polypropylene oxide (PPOX) or polyoxypropylene (POP)
anionic ring-opening polymerization of propylene oxide
–CH2CH(CH3)O–
Arcol from Covestro
Polytetramethylene glycol (PTMG) or Polytetramethylene ether glycol (PTMEG)
Polytetrahydrofuran (PTHF)
Acid-catalyzed ring-opening polymerization of tetrahydrofuran
−CH2CH2CH2CH2O−
Terathane from Invista and PolyTHF from BASF
· Physical properties
Ether
Ether
Selected data about some alkyl ethers
Ether
Selected data about some alkyl ethers
Structure
Selected data about some alkyl ethers
m.p. (°C)
Selected data about some alkyl ethers
b.p. (°C)
Selected data about some alkyl ethers
Solubility in 1 liter of H2O
Selected data about some alkyl ethers
Dipole moment (D)
Dimethyl ether
Dimethyl ether
Selected data about some alkyl ethers
Dimethyl ether
Selected data about some alkyl ethers
CH3–O–CH3
Selected data about some alkyl ethers
−138.5
Selected data about some alkyl ethers
−23.0
Selected data about some alkyl ethers
70 g
Selected data about some alkyl ethers
1.30
Diethyl ether
Diethyl ether
Selected data about some alkyl ethers
Diethyl ether
Selected data about some alkyl ethers
CH3CH2–O–CH2CH3
Selected data about some alkyl ethers
−116.3
Selected data about some alkyl ethers
34.4
Selected data about some alkyl ethers
69 g
Selected data about some alkyl ethers
1.14
Tetrahydrofuran
Tetrahydrofuran
Selected data about some alkyl ethers
Tetrahydrofuran
Selected data about some alkyl ethers
O(CH2)4
Selected data about some alkyl ethers
−108.4
Selected data about some alkyl ethers
66.0
Selected data about some alkyl ethers
Miscible
Selected data about some alkyl ethers
1.74
Dioxane
Dioxane
Selected data about some alkyl ethers
Dioxane
Selected data about some alkyl ethers
O(C2H4)2O
Selected data about some alkyl ethers
11.8
Selected data about some alkyl ethers
101.3
Selected data about some alkyl ethers
Miscible
Selected data about some alkyl ethers
0.45
Selected data about some alkyl ethers
Ether
Structure
m.p. (°C)
b.p. (°C)
Solubility in 1 liter of H2O
Dipole moment (D)
Dimethyl ether
CH3–O–CH3
−138.5
−23.0
70 g
1.30
Diethyl ether
CH3CH2–O–CH2CH3
−116.3
34.4
69 g
1.14
Tetrahydrofuran
O(CH2)4
−108.4
66.0
Miscible
1.74
Dioxane
O(C2H4)2O
11.8
101.3
Miscible
0.45
· Important ethers
Ethylene oxide
A cyclic ether. Also the simplest epoxide.
Dimethyl ether
A colourless gas that is used as an aerosol spray propellant. A potential renewable alternative fuel for diesel engines with a cetane rating as high as 56–57.
Diethyl ether
A colourless liquid with sweet odour. A common low boiling solvent (b.p. 34.6 °C) and an early anaesthetic. Used as starting fluid for diesel engines. Also used as a refrigerant and in the manufacture of smokeless gunpowder, along with use in perfumery.
Dimethoxyethane (DME)
A water miscible solvent often found in lithium batteries (b.p. 85 °C):
Dioxane
A cyclic ether and high-boiling solvent (b.p. 101.1 °C).
Tetrahydrofuran (THF)
A cyclic ether, one of the most polar simple ethers that is used as a solvent.
Anisole (methoxybenzene)
An aryl ether and a major constituent of the essential oil of anise seed.
Crown ethers
Cyclic polyethers that are used as phase transfer catalysts.
Polyethylene glycol (PEG)
A linear polyether, e.g. used in cosmetics and pharmaceuticals.
Polypropylene glycol
A linear polyether, e.g. used in polyurethanes.
Platelet-activating factor
An ether lipid, an example with an ether on sn-1, an ester on sn-2, and an inorganic ether on sn-3 of the glyceryl scaffold.

References

  1. IUPAC, Compendium of Chemical Terminology, 5th ed. (the "Gold Book") (2025). Online version: (2006–) "ethers". .mw- .mw-
    https://goldbook.iupac.org/terms/view/E02221.html
  2. The Ether Linkage
    https://doi.org/10.1002%2F9780470771075
  3. Dalton Trans.
    https://doi.org/10.1039%2Fb405684a
  4. Wilhelm Heitmann, Günther Strehlke, Dieter Mayer "Ethers, Aliphatic" in Ullmann's Encyclopedia of Industrial Chemistry W
    https://doi.org/10.1002%2F14356007.a10_023
  5. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure
    https://books.google.com/books?id=JDR-nZpojeEC&printsec=frontcover
  6. Organic Syntheses
    http://www.orgsyn.org/demo.aspx?prep=CV5P0412
  7. Inorg. Chim. Acta
    https://doi.org/10.1016%2FS0020-1693%2800%2986863-2
  8. Organic chemistry
    https://archive.org/details/organicchemistry00clay_0/page/129
  9. Synthesis
    https://doi.org/10.1055%2Fs-2006-942440
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