919-94-8

Basic information

• Product Name: 1,1-DIMETHYLPROPYL ETHYL ETHER
• Synonyms: TERT-AMYL ETHYL ETHER;1,1-DIMETHYLPROPYL ETHYL ETHER;2-ethoxy-2-methyl-butan;2-Ethoxy-2-methylbutane;2-ethoxy-2-methyl-butane;Butane, 2-ethoxy-2-methyl-;ether,ethyltert-pentyl;Ethyl 1,1-dimethylpropyl ether
• CAS NO: 919-94-8
• Molecular Formula: C₇H₁₆O
• Molecular Weight: 116.2
• Mol File: 919-94-8.mol
• Article Data: 10

Chemical Properties

• Melting Point: -95.35°C (estimate)
• Boiling Point: 102°C
• Flash Point: 5°C
• Appearance: /
• Density: 0,76 g/cm3
• Vapor Pressure: 39.4mmHg at 25°C
• Refractive Index: 1.3890-1.3930
• CAS DataBase Reference: 1,1-DIMETHYLPROPYL ETHYL ETHER(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1-DIMETHYLPROPYL ETHYL ETHER(919-94-8)
• EPA Substance Registry System: 1,1-DIMETHYLPROPYL ETHYL ETHER(919-94-8)

Safety Data

• Statements: 11
• Safety Statements: 9-16-33
• RIDADR: 3271
• RTECS: KO0351000
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 919-94-8(Hazardous Substances Data)

Usage

General Description

1,1-Dimethylpropyl Ethyl Ether, also known as tertiary-butyl ethyl ether (TBEE), is a chemical compound highly known for its use as an oxygenate in unleaded gasoline which helps in reducing the pollutants emitted by motor vehicles and other gasoline-powered equipment. Its molecular formula is C7H16O and it is characterized by a strong ether smell. This colorless liquid has a boiling point of 95°C and a melting point of -95°C. Its low melting and boiling points make it a good solvent for many organic reactions. Despite its benefits, exposure to 1,1-Dimethylpropyl Ethyl Ether can cause irritation in the eyes, skin, and respiratory system if not handled properly.

InChI:InChI=1/C7H16O/c1-5-7(3,4)8-6-2/h5-6H2,1-4H3

Upstream product

• 513-35-9 2-methyl-but-2-ene 
• 64-17-5 ethanol 
• 75-85-4 tert-Amyl alcohol 
• 594-38-7 2-iodo-2-methylbutane 
• 75-03-6 ethyl iodide 
• 18295-27-7 2-iodo-3-methylbutane 
• 18295-25-5 3-bromo-2-methylbutane 
• 563-46-2 2-Methyl-1-butene 
• 74-96-4 ethyl bromide 

Downstream Products

• 513-35-9 2-methyl-but-2-ene 
• 563-46-2 2-Methyl-1-butene 
• 64-17-5 ethanol 
• 594-38-7 2-iodo-2-methylbutane 
• 75-03-6 ethyl iodide 

Relevant articles and documents

METHOD OF PRODUCING TERTIARY AMYL ETHYL ETHER

A process for the production of tertiary ethers, including: feeding a hydrocarbon stream comprising isoolefins and propionitrile to a distillation column reactor system containing at least one etherification reaction zone; feeding a C2 to C6 monoalcohol or mixture thereof to the distillation column reactor; concurrently in the distillation column reactor system: reacting a portion of the isoolefins with a portion of the alcohols to form a tertiary ether; and separating the tertiary ether from unreacted isoolefins; withdrawing the tertiary ether and propionitrile from the distillation column reactor system as a bottoms; withdrawing the unreacted isoolefins from the distillation column reactor system as an overheads; and operating the distillation column reactor system such that the etherification reaction zone is substantially free of propionitrile.

Enthalpies of formation of 2-methyl-2-ethoxypropane and 2-ethyl-2-ethoxypropane from equilibrium measurements

The equilibria for the synthesis of C2H5OC(CH3)3 (A) and C2H5OC(CH3)2(C2H5) (B) from C2H5OH (C) and CH2:C(CH3)2 (D) or CH3CH:C(CH3)2 (E) in the liquid phase were investigated at temperatures from 313 K to 412 K.On the basis of experimental equilibrium constants found for n(C)/n(D) or n(C)/n(E) >/= 4, the following values were obtained for ΔrH0m/(kJ * mol-1) and ΔrS0m/(J * K-1 * mol-1): (C + D = A), -(35.45 +/- 1.94) and -(82.37 +/- 5.99); (C + A = B), -(34.13 +/- 0.81) and -(87.82 +/- 2.18).The following values of ΔfH0m(298.15 K)/(kJ * mol-1) have been derived: C2H5OC(CH3)3(l), -(350.8 +/- 2.6); C2H5OC(CH3)2(C2H5)(l), -(379.8 +/- 1.4).

The Mechanism of Ethylene Elimination from the Oxonium Ions CH3CH2CH=O+CH2CH3 and (CH3)2C=O+CH2CH3

The reactions of the metastable oxonium ions CH3CH2CH=O+CH2CH3 and (CH3)2C=O+CH2CH3 are reported and discussed.Various mechanisms for ethylene elimination, which is the principal dissociation route for these ions, are considered.It is shown by means of 2H-labelling experiments and analysis of collision-induced dissociation spectra that routes involving ion-neutral complexes pre-empt 'conventional' mechanisms for these processes.In contrast, the behaviour of the lower homologues CH3CH2CH=OR+ and (CH3)2C=OR+ (R = H, CH3) is consistent with the operation of 'conventional' mechanisms for ethylene expulsion.This contrast is interpreted in energetic terms.The significance of these results for the chemistry of homologous and analogous 'onium' ions containing a Z+-R function (Z = O, S, NH, NCH3; R= CnH2n+1, n 2) is explained.