Trimer of propylene

Nonene (n-nonene boiling point 146°C, density 0.730) was originally made by the trimerization of propylene (CH3CH=CH2) to give a branched nonene this product now has limited use for detergents because of nonbiodegradability. 

Apart from the isooctanol and isononanol discussed above, isodecanol can be produced from the trimer of propylene and isotridecanoi from its tetramer. Alcohols with 8... 

It is worth underlining that, with ionic complexes whatever the ligands used, linear structures are disfavored, especially in higher oligomers thus the trimers of propylene are highly branched and contain only 3% linear nonenes. 

DIDP production depends on the availability of phthalic anhydride. Isodecanol (iso-decyl alcohol) is produced from nonene, the trimer of propylene. About eight per-... 

The feedstock, usuaHy consisting of propylene and butylenes (various isomers of C Hg) from cracking processes, may even consist of selective olefins for dimer, trimer, or tetramer production ... 

The product is a mixmre of dimers, trimers, tetramers, and pentamers having an average RON (Research Octane Number) = 95. Table 3-14 shows the analysis of feed and products from dimerization of propylene. ... 

V. Kh. Dulaev, N. M. Bondarets, N. A. Polukhina, V. I. Petresku, R. G. Galiev, P. P. Kapustin, and O. S. Matrosov. Composition for preparation of aerated plugging solution—contains Portland cement, oxyethylated monoalkylphenol(s) of propylene trimers, glycol mixture, air, water, etc. Patent SU 1745893-A, 1992. 

Interestingly, if benzene is left out similar conditions are used to manufacture the trimer and tetramer of propylene. The cumene is separated by distillation, bp 153°C. 

This reaction mechanism also explains why oligomerization of propylene, as mentioned, tends to yield much more trimer than dimer. The dimeric carbocation (4) formed readily undergoes a hydride shift to yield tertiary cation 5 ... 

Nonyltrichlorosilane can be synthesised by the hydrosilylation of propylene trimer with (nonen-l)trichlorosilane in the presence of a catalyst. 

Fig. 23. Asymmetric oligomerzation of propylene. Isomers of trimeric propylene were detected by gas chromatography/mass spectrometry (204).

Fig. 24. Asymmetric oligomerization of propylene at various temperatures gas-chromatographic separation of 2,4-dimethyl-2-heptene (trimer) in a capillary column coated with octakis(6-0-methyl-2,3-di-0-pentyl)cyclodextrin) (204).

Polymerization of olefins in the presence of sulfuric acid accompanied by hydrogenation and dehydrogenation was reported by S. S. Nametkin in 1934 similar work was also reported by him in 1937 (247). The mechanism of polymerization of propylene, as indicated by the structure of its dimers and trimers, was thought by Antsus and Petrov (293) to be similar to that of polymerization of isobutylene (apparently over acid catalysts) in the first step 2-methyl-l-pentene was formed. 

Evidence of oligomers appears at short contact time. Figure 3 shows plateaus corresponding to the trimer, tetramer and penta-mer of propylene at conditions of 2.7 WHSV, 400°F, 500 psig at which propylene conversion if 67%. This contrasts with the smooth curve at 0.4 WHSV, 98% propylene conversion. 

Jones and Savill ( 6) have described the very rapid catalytic effect upon trimerization of isocyanates by ethylene oxide, propylene oxide, styrene oxide, or epichlorhydrin when a trace of pyridine is present. No reaction occurs in the absence of pyridine. They express the opinion that the function of the tertiary base is to open the epoxide ring and that the catalytic action is believed due to initial formation of... 

A. M. Joshi, W. N. Delgass, K. T. Thomson, Partial oxidation of propylene to propylene oxide over a neutral gold trimer in the gas phase A Density Functional Theory study, J. Phys. Chem. B 110 (2006) 2572. 

In the absence of propylene oxide only traces of trimer were isolated. However [15] in the presence of iV,7V -A -tris(3-dimethylaminopropyl)35 / hexa-hydrotriazine trimerization took place in the absence of propylene oxide. 

There are two different ways of making 2-ethoxyoctane from 2-octanol using the Williamson ether synthesis. When pure (—)-2-octanol of specific rotation —8.24° is treated with sodium metal and then ethyl iodide, the product is 2-ethoxyoc-tane with a specific rotation of —15.6°. When pure (—)-2-octanol is treated with tosyl chloride and pyridine and then with sodium ethoxide, the product is also 2-ethoxyoctane. Predict the rotation of the 2-ethoxyoctane made using the tosy-lation/sodium ethoxide procedure, and propose a detailed mechanism to support your predictioa 14-43 Under base-catalyzed conditions, several molecules of propylene oxide can react to give short polymers. Propose a mechanism for the base-catalyzed formation of the following trimer. 

The oleflnic hydrocarbon gases, propylene and the butylenes, are sent to polymerization and alkylation. Polymerization forms dimers and trimers of these olefins for use in gasoline blending or for petrochemicals. Alkylation is a more common process in which the olefins are reacted with isobutane. This step produces the more desirable isoparaffins for gasoline blending. 

CrCUCpylj, CrCl3(4-Etpy)3, and [CrClsCPBus) ] complexes have been used as catalysts for dimerization of propylene [567,568], In addition to dimers, trimers and tetramers are formed. The Cg fraction is composed mainly of 2-methylpentene (69%) and n-hexane (31%). EtAlCh is used as the cocatalyst in these systems. 

Formation of linear trimers and tetramers starting from an a-olefin (Table V) is difficult to vizualize and suggests an intramolecular rearrangement which may be ascribed to a most favored primary carbon— metal bond (or to its higher reactivity), e.g. in the case of propylene ... 

Isospecificity derived from racemic enantiomers can be understood by considering that the approach of the incoming prochiral propylene to the reactive metal-carbon bond must be controlled by the chiral structure of reactive centers (enantiomorphic site control). Pino and coworkers obtained (S)-2,4-dimethylheptane with high optical purity by trimerizing propene in the presence of (—)(R) -bis(l-tetrahydroindenyl)ethane zirconium dimethyl/MAO in the presenee of H2, whieh causes very fast chain transfer. As insertion oceurs with cis stereochemistry, they supposed the prevailing chirality of the hydro-oligomers is supposed to indicate that the Re enantioface of propylene preferentially approached Zr—carbon bond (Fig. 15) [64, 65]. 

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