Isooctane

Table 5.4 gives the specific energies of selected organic liquid compounds. Compared with the isooctane chosen as the base reference, the variations from one compound to another are relatively small, on the order of 1 to 5%, with the exception of some particular chemical structures such as those of the short chain nitroparaffins (nitromethane, nitroethane, nitropropane) that are found to be energetic . That is why nitromethane, for example, is recommended for very small motors such as model airplanes it was also used in the past for competitive auto racing, for example in the Formula 1 at Le Mans before being forbidden for safety reasons. 

The motor fuel under test is compared to two pure hydrocarbons chosen as references. The first is 2, 2, 4-trimethylpentane or isooctane which is very resistant to auto-ignition and to which is arbitrarily given the number 100 /... 

A motor fuel has an octane number X if it behaves under tightly defined experimental conditions the same as a mixture of X volume % of isooctane and (100 - X)% of n-heptane. The isooctane-heptane binary mixtures are called primary reference fuels. Octane numbers higher than 100 can also be defined the reference material is isooctane with small quantities of tetraethyl lead added the way in which this additive acts will be discussed later. 

Fig. III-9. Representative plots of surface tension versus composition, (a) Isooctane-n-dodecane at 30°C 1 linear, 2 ideal, with a = 48.6. Isooctane-benzene at 30°C 3 ideal, with a = 35.4, 4 ideal-like with empirical a of 112, 5 unsymmetrical, with ai = 136 and U2 = 45. Isooctane-

The data in Table III-2 have been determined for the surface tension of isooctane-benzene solutions at 30°C. Calculate Ff, F, F, and F for various concentrations and plot these quantities versus the mole fraction of the solution. Assume ideal solutions. 

Mole Fraction Isooctane Surface Tension (dyn/cm) Mole Fraction Isooctane Surface Tension (dyn/cm)... 

Using these group values, predict isooctane (2,2,3-trimethylpentane) and... 

Alkylation combines lower-molecular-weight saturated and unsaturated hydrocarbons (alkanes and alkenes) to produce high-octane gasoline and other hydrocarbon products. Conventional paraffin-olefin (alkane-alkene) alkylation is an acid-catalyzed reaction, such as combining isobutylene and isobutane to isooctane. 

The two dimers of 2 methylpropene shown in the equation can be converted to 2 2 4 trimethylpentane (known by its common name isooctane) for use as a gasoline additive Can you suggest a method for this conversion ... 

Octane rating (Section 2 16) The capacity of a sample of gasoline to resist knocking expressed as a number equal to the percentage of 2 2 4 trimethylpentane ( isooctane ) in an isooctane-heptane mixture that has the same knocking characteristics... 

In liquid-solid adsorption chromatography (LSC) the column packing also serves as the stationary phase. In Tswett s original work the stationary phase was finely divided CaCOa, but modern columns employ porous 3-10-)J,m particles of silica or alumina. Since the stationary phase is polar, the mobile phase is usually a nonpolar or moderately polar solvent. Typical mobile phases include hexane, isooctane, and methylene chloride. The usual order of elution, from shorter to longer retention times, is... 

Although acetic acid and water are not beheved to form an azeotrope, acetic acid is hard to separate from aqueous mixtures. Because a number of common hydrocarbons such as heptane or isooctane form azeotropes with formic acid, one of these hydrocarbons can be added to the reactor oxidate permitting separation of formic acid. Water is decanted in a separator from the condensate. Much greater quantities of formic acid are produced from naphtha than from butane, hence formic acid recovery is more extensive in such plants. Through judicious recycling of the less desirable oxygenates, nearly all major impurities can be oxidized to acetic acid. Final acetic acid purification follows much the same treatments as are used in acetaldehyde oxidation. Acid quahty equivalent to the best analytical grade can be produced in tank car quantities without difficulties. 

Sodium acetate reacts with carbon dioxide in aqueous solution to produce acetic anhydride and sodium bicarbonate (49). Under suitable conditions, the sodium bicarbonate precipitates and can be removed by centrifugal separation. Presumably, the cold water solution can be extracted with an organic solvent, eg, chloroform or ethyl acetate, to furnish acetic anhydride. The half-life of aqueous acetic anhydride at 19°C is said to be no more than 1 h (2) and some other data suggests a 6 min half-life at 20°C (50). The free energy of acetic anhydride hydrolysis is given as —65.7 kJ/mol (—15.7 kcal/mol) (51) in water. In wet chloroform, an extractant for anhydride, the free energy of hydrolysis is strangely much lower, —50.0 kJ/mol (—12.0 kcal/mol) (51). Half-life of anhydride in moist chloroform maybe as much as 120 min. Ethyl acetate, chloroform, isooctane, and / -octane may have promise for extraction of acetic anhydride. Benzene extracts acetic anhydride from acetic acid—water solutions (52). 

The rates of these two reactions have been studied for the attack of trifluoromethyl (51) and methyl radicals (52) in isoprene that has been dissolved in 2,3-dimethylbutane and isooctane, respectively. The rate constants for the reactions with isoprene are much greater than those for the attack on the solvent. The ratio between the two rates for the attack of trifluoromethyl radicals varies from 1090 at 65°C to 233 at 180°C. For the corresponding reaction involving methyl radicals, the ratio is 2090 at 65°C. 

Octane number is a measure of a fuel s abiUty to avoid knocking. The octane number of a gasoline is deterrnined in a special single-cylinder engine where various combustion conditions can be controlled. The test engine is adjusted to give trace knock from the fuel to be rated. Various mixtures of isooctane (2,2,4-trimethyl pentane) and normal heptane are then used to find the ratio of the two reference fuels that produce the same intensity of knock as that by the unknown fuel. 

By defining isooctane as having an octane number of 100 and / -heptane as having an octane number of 0, the volumetric percentage of isooctane in heptane that matches the knock from the unknown fuel can be calculated as the octane number of the fuel. For example, 90 vol % isooctane and 10 vol % normal heptane produce a 90-octane-number reference fuel. 

Instmmental methods of analysis provide information about the specific composition and purity of the amines. QuaUtative information about the identity of the product (functional groups present) and quantitative analysis (amount of various components such as nitrile, amide, acid, and deterruination of unsaturation) can be obtained by infrared analysis. Gas chromatography (gc), with a Hquid phase of either Apiezon grease or Carbowax, and high performance Hquid chromatography (hplc), using siHca columns and solvent systems such as isooctane, methyl tert-huty ether, tetrahydrofuran, and methanol, are used for quantitative analysis of fatty amine mixtures. Nuclear magnetic resonance spectroscopy (nmr), both proton ( H) and carbon-13 ( C), which can be used for quaHtative and quantitative analysis, is an important method used to analyze fatty amines (8,81). 

Since a carbocation can add to an alkene to form a larger cation, under acidic conditions isobutylene can dimerize to form 2,4,4-trim ethyl -1 -pen ten e [107-39-1] and 2,4,4-trimethyl-2-pentene [107-40-4J, which can then be hydrogenated in the presence of nickel to form isooctane [540-84-1]. This reaction is no longer of commercial significance. 

Alkylation of isobutylene and isobutane in the presence of an acidic catalyst yields isooctane. This reaction proceeds through the same mechanism as dimerization except that during the last step, a proton is transferred from a surrounding alkane instead of one being abstracted by a base. The cation thus formed bonds with the base. Alkylation of aromatics with butylenes is another addition reaction and follows the same general rules with regard to relative rates and product stmcture. Thus 1- and 2-butenes yield j -butyl derivatives and isobutylene yields tert-huty derivatives. 

The alkylate contains a mixture of isoparaffins, ranging from pentanes to decanes and higher, regardless of the olefins used. The dominant paraffin in the product is 2,2,4-trimethylpentane, also called isooctane. The reaction involves methide-ion transfer and carbenium-ion chain reaction, which is cataly2ed by strong acid. 

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