Isoamylene

One can react methanol with the tertiary olefins having five c irbon atoms (isoamylenes). This process increases the octane number of FCC olefinic C5 fractions, in order to reduce the concentration of olefins and to increase gasoline production. 

Some isopentane is dehydrogenated to isoamylene and converted, by processes analogous to those which produce methyl /-butyl ether [1634-04-4] (MTBE) to /-amyl methyl ether [994-05-8] (TAME), which is used as a fuel octane enhancer like MTBE. The amount of TAME which the market can absorb depends mostly on its price relative to MTBE, ethyl /-butyl ether [637-92-3] (ETBE), and ethanol, the other important oxygenated fuel additives. 

The cmde product formed from the alkylation of phenol with isoamylene contains principally 2-/ r2 -amylphenol, 4-/ r2 -amylphenol, and 2,4-di-/ r2 -amylphenol. 4-/ r2 Amylphenol is purified to its typical assay of 99+% by fractional distillation. 4-/ r2 -Amylphenol [80-46-6] is commercially available as a soHd, flaked material packaged ia paper or plastic bags (25 kg net weight) or as a molten material ia tank wagon or railcar quantities. 

Diall lated Phenols. 2,4-Di-tert-amjlphenol (2,4-DTAP) or 2,4-bis(l,l-dimethylpropyl)phenol is produced by the alkylation of phenol with isoamylene under acid catalysis in a mole ratio of 2 1 (isoamylene to phenol). The cmde alkylation product contains 4-/ f2 -amylphenol,... 

Although current United States synthetic capacity for isoprene is based entirely on dehydrogenation of refinery isoamylenes and demethanation of... 

A second route based on olefin disproportionation was developed by Phillips Petroleum (131). Here isobutylene reacts with propylene to form isoamylenes, which are dehydrogenated to isoprene. 2-Butene can be used in place of propylene since it also yields isoamylene and the coproduct propylene can be recycled. Use of mixed butylenes causes the formation of pentenes, giving piperjlene, which contaminates isoprene. 

Commercially, sulfonic acid ion-exchange resins are used in fixed-bed reactors to make these tertiary alkyl ethers (14). Since the reaction is very selective to tertiary olefins and also reversible, a two-step procedure is also used to recover commercially pure tertiary olefins from mixed olefin process streams. The corresponding tertiary alkyl ether is produced in the olefin mixture and then easily separated from the unreacted olefins by simple fractionation. The reaction is then reversed in a second step to make a commercially pure tertiary olefin, usually isobutylene or isoamylene. 

The most common ethers being used as additives are methyl tertiary butyl ether (MTBE), and tertiary amyl methyl ether (TAME). Many of the larger refineries manufacture their own supplies of MTBE and TAME by reacting isobutylene and/or isoamylene with methanol. Smaller refineries usually buy their supplies from chemical manufacturers or the larger refineries. 

A number of examples have been cited by Chakrabarti and Sharma (1993) and Sharma (1995). The example of etherification of phenols, substituted phenols, cresols, naphthols, etc., with isobutylene and isoamylene may be empahsized where homogeneous catalysts lead to... 

Hexanes (Isoamylenes) Isoprene Methylpen tenes Benzene... 

Synonyms EINECS 209-249-1 Isopentene Isopropylethene Isopropylethylene a-Isoamylene 2-Methyl-3-butene 3-Methylbutene UN 2561 Vinyl isopropyl. 

Indenopyrene, see Indeno[l,2,3-crf pyrene l//-Indole, see Indole Indolene, see Indoline Inexit, see Lindane Inhibisol, see 1,1,1-Trichloroethane Insecticide 497, see Dieldrin Insecticide 4049, see Malathion Insectophene, see a-Endosulfan, p-Endosulfan Intox 8, see Chlordane Inverton 245, see 2,4,5-T lodomethane, see Methyl iodide IP, see Indeno[l,2,3-crf pyrene IP3, see Isoamyl alcohol Ipaner, see 2,4-D IPE, see Isopropyl ether IPH, see Phenol Ipersan, see Trifluralin Iphanon, see Camphor Isceon 11, see Trichlorofluoromethane Isceon 122, see Dichlorodifluoromethane Iscobrome, see Methyl bromide Iscobrome D, see Ethylene dibromide Isoacetophorone, see Isophorone a-Isoamylene, see 3-Methyl-l-butene Isoamyl ethanoate, see Isoamyl acetate Isoamylhydride, see 2-Methylbutane Isoamylol, see Isoamyl alcohol Isobac, see 2,4-Dichlorophenol Isobenzofuran-l,3-dione, see Phthalic anhydride 1,3-Isobenzofurandione, see Phthalic anhydride IsoBuAc, see Isobutyl acetate IsoBuBz, see Isobutylbenzene Isobutane, see 2-Methylpropane Isobutanol, see Isobutyl alcohol Isobutene, see 2-Methylpropene Isobutenyl methyl ketone, see Mesityl oxide Isobutyl carbinol, see Isoamyl alcohol Isobutylene, see 2-Methylpropene Isobutylethylene, see 4-Methyl-l-pentene Isobutyl ketone, see Diisobutyl ketone Isobutyl methyl ketone, see 4-Methyl-2-pentanone Isobutyltrimethylmethane, see 2,2,4-Trimethylpentane Isocumene, see Propylbenzene Isocyanatomethane, see Methyl isocyanate Isocyanic acid, methyl ester, see Methyl isocyanate Isocyanic acid, methylphenylene ester, see 2,4-Toluene-diisocyanate... 

The isoprene monomer is not readily available from direct cracking processes. Several routes are employed for its synthesis. One route begins with the extraction of isoamylene fractions from catalytically cracked gasoline streams. Isoprene is produced by subsequent catalytic dehydrogenation. 

Similar to the processes used in the manufacture of 1,3-butadiene, isoprene can be prepared from isopentane, isoamylenes, or a mixed isoC5 feed.172 176 177 The Shell process177 dehydrogenates isoamylenes to isoprene in the presence of steam with 85% selectivity at 35% conversion, over a Fe203—K2CO3—Cr2Oj catalyst at 600°C. 

A number of new processes exploiting metathesis have been developed by Phillips. A novel way to manufacture lubricating oils has been demonstrated.145 The basic reaction is self-metathesis of 1-octene or 1-decene to produce Ci4-C28 internal alkenes. The branched hydrocarbons formed after dimerization and hydrogenation may be utilized as lubricating oils. Metathetical cleavage of isobutylene with propylene or 2-butenes to isoamylenes has a potential in isoprene manufacture.136,146 High isoamylene yields can be achieved by further metathesis of C6+ byproducts with ethylene and propylene. Dehydrogenation to isoprene is already practiced in the transformation of isoamylenes of FCC C5 olefin cuts. 

Figure 4.2 Dependence of conjugated dehydrogenation selectivity (1), isoprene yield (2) and total side products yield (3) on isoamylenes and nitrogen mixture rate. T = 553 °C volume ratio C5H1() N2 = 1 10 20% aqueous H202 rate is 0.185 ml/h.

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