1- Decene dimerization

Decene. See Decene-1 1-Decene dimer. See Didecene Decene, homopolymer. See Polydecene 1-Decene, homopolymer, hydrogenated CAS 68037-01-4... 

The hydrogenated dimer of 1-decene [1208] can be used instead of conventional organic-based fluids, as can n-l-octene [1105]. 

J. D. Mercer and L. L. Nesbit. Oil-base drilhng fluid comprising branched chain paraffins such as the dimer of 1-decene. Patent US 5096883,1992. 

Synthetic fire-resistant fluids have been developed to replace petroleum-based fluids for many applications. Although there are several types of these less hazardous fluids, the only synthetic fluids discussed in this profile are phosphate esters and polyalphaolefins. The phosphate esters are tertiary esters of orthophosphoric acid, 0=P(0H)3, and may be triaryl, trialkyl, and alkyl/aryl. The polyalphaolefins are usually based on 2-decene and contain a mixture of oligomers (dimers, trimers, etc.). 

A typical polyalphaolefin oil prepared from 1-decene and BF3t -C4H9OH catalyst at 30 °C contains predominantly trimer (C30 hydrocarbons) with much smaller amounts of dimer, tetramer, pentamer, and hexamer. While 1-decene is the most common starting material, other alphaolefins can be used, depending on the needs of the product oil. 

Polyalphaolefin Hydraulic Fluids. Polyalphaolefms are made by oligomerizing alphaolefins such as 1-decene in the presence of a catalyst (Newton 1989 Shubkin 1993 Wills 1980). The crude reaction mixture is quenched with water, hydrogenated, and distilled. The number of monomer units present in the product polyalphaolefin oil depends on a number of reaction parameters including the type of catalyst, reaction temperature, reaction time, and pressure (Shubkin 1993). The exact combination of reaction parameters used by a manufacturer is tailored to fit the end-use of the resulting polyalphaolefin oil. A typical polyalphaolefin oil prepared from 1-decene and BF3- -C4H9OH catalyst at 30 °C contains predominantly trimer (C30 hydrocarbons) with much smaller amounts of dimer, tetramer, pentamer, and hexamer. While 1-decene is the most common starting material, other alphaolefins can be used, depending on the needs of the product oil. 

Polyalphaolefin Hydraulic Fluids. The methods for analyzing polyalphaolefin hydraulic fluids are identical to those for the mineral oil hydraulic fluids (see Table 6-1). Polyalphaolefin oils can be distinguished from mineral oils because they will be present in combinations of the alphaolefin from which they were synthesized (Shubkin 1993). Thus, polyalphaolefins obtained from 1-decene will be present as dimers (C20 alkanes), trimers (C30 alkanes), tetramers (C40 alkanes), pentamers (C50 alkanes), etc., with no alkanes between these isomers (e.g., there will be no C2i alkanes present in the oil). This method of identification will only be possible if the polyalphaolefin hydraulic fluids contain no mineral oils or if the samples being analyzed were not exposed to mineral oils. 

Use of less sterically hindered examples of 5 in combination with MAO allows for active catalysts for the linear (head-to-head) dimerisation of a-olefins such as 1-butene, 1-hexene, 1-decene and Chevron Phillips C20-24 a-olefin mixture (Scheme 4) [47], The mechanism for dimerisation is thought to involve an initial 1,2-insertion into an iron-hydride bond followed by a 2,1-insertion of the second alkene and then chain transfer to give the dimers. Structurally related cobalt systems have also been shown to promote dimerisation albeit with lower activities [62], Oligomerisation of the a-olefms propene, 1-butene and 1-hexene has additionally been achieved with the CF3-containing iron and cobalt systems 5j and 6j yielding highly linear dimers [23],... 

Decene complexes with gold, 12 348 Deformation density, 27 29-33 Degradation reactions, heteronuclear gold cluster compounds, 39 336-337 Dehydration reactions, osmium(II), 37 351 Delocalization, see also Valence delocalization added electron, reduced dimer, 38 447, 449 optical centers, interaction with surroundings, 35 380 Density... 

Possibly the most convincing evidence for positive ion-molecule reactions in polymers is the high rate of decay of vinyl unsaturation during the radiolysis of polyethylene, as recently discussed by Dole, Fallgatter, and Katsuura (13). The ideas of these authors with respect to the carbonium ion mechanism for vinyl decay by means of a dimerization reaction were largely suggested by the mechanisms proposed by Col-linson, Dainton, and Walker (5) for vinyl decay (polymerization) in the radiolysis of n-hexa-l-decene, Reactions 3 and 4 of Table I. 

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. 

Although the ylides are too unstable for isolation, they can be utilized in situ for stereoselective syntheses of a, j8-epoxy and -aziridinyl ketones. For example, the generation of l-phenyliodonium-l-decen-2-olate (45) in the presence of aliphatic and aromatic aldehydes affords the corresponding epoxy ketones with high trans-stereoselectivity (Scheme 73) [197]. Efforts to trap 45 with ketones were unsuccessful, leading instead to 10-eicosene-9,12-dione, the formal ylide dimerization product. 

Rationalizations of hydroboration stereoselectivity using models with dimeric boranes are thus not viable. Recent secondary isotope-effect measurements may suggest a model (Mann et al., 1986). Addition of a chiral dialkyl borane to 3-deuterio-cw-3-pentene, followed by alkaline oxidation, yields equal amounts of 3- and 4-deuterio-3-hexanols showing that the secondary isotope effects at these alkene sites are vanishingly small. Deuterium substitution at the allylic sites has a much larger effect. Thus similar treatment of 4,4-dideuterio-cw-5-decene yields a 2.86 1 mixture of 4,4-dideuterio- and 6,6-dideuterio-5-decanols. 

Propene and higher a-olefins also may be dimerized or oligomerized by these catalysts. Generally, reactivity is much lower than that of ethylene and decreases in the order ethylene propylene > 1-butene > 1-hexene > 1-octene > 1-decene. Also the selectivity is lower and mainly branched dimers or oligomers are formed. ... 

BP Chemicals studied the use of chloroaluminates as acidic catalysts and solvents for aromatic alkylation [43]. At present, the AICI3 existing technology (based on red oil catalyst) is still used industrially, but continues to suffer from poor catalyst separation and recycle [44]. The aim of the work was to evaluate the AlCls-based ionic liquids, with the emphasis placed on the development of a clean and recyclable system for the production of ethylbenzene (benzene/ethene alkylation) and synthetic lubricants (alkylation of benzene with 1-decene). The production of linear alkyl benzene (LAB) has also been developed by Akzo [45]. The eth)4benzene experiments were run by BP in a pilot loop reactor similar to that described for the dimerization (Fig. 5.4-8). 

Gallium hydrides also add to alkenes. For example, Et GaH adds 1-decene giving Et2GaC3oH2i, and the dimer (HGaCl2)2 adds to terminal olefins. 

Important unfunctionalized acyclic alkenes used in industry are ethene (C2) and propene (C3), isomeric butenes (C4), octenes (Cg), and olefins up to a chain length of C g. In general, a distinction is made between short-chain (C3, C4), medium-chain (C5-C42), and long-chain (C13-C19) 0x0 products. Some linear a-olefins (LAOs), such as 1-butene, 1-hexene, 1-octene, or 1-decene, can be extracted selectively from Fischer- Tropsch processes. As exemplarily conducted in Sasol s SYNTHOL process, a range of olefins with a broad distribution of odd and even carbon numbers can be obtained [9, 10]. In the case of low-cost ethylene, dimerization may produce 1-butene. Trimerization or tetramerization produces 1-hexene and/or 1-octene [11]. 

Steric effect is very crudal in the selectivity of ds-diol [79]. While the (6-Me2-BPMEN)Fe(OTf)2 produces ds-l,2-cylcooctanediol as the major product (Table 1.5, entry 4), the 5-methyl analog performs as an epoxidation catalyst (Table 1.5, entry 5). In the presence of acetic add, the nonsubstituted (B PM EN) Fe(SbF6)2, also referred to as (MEP)Fe(SbF6)2, self-assembled to a dimer as a stmdural mimic of methane monooxygenase (MMO) [80]. It catalyzes the epoxidation of a range of aliphatic alkenes. Even the relatively nonreactive substrate, 1-decene, can be oxidized to the corresponding epoxide in 85% yield in 5 min. 

BF,-Fl20-alkanoic acids 1-hexene, 1-decene, 1-tetradecene high branched-chain dimers to pentamers 909, 910... 

FIG. 3 Schematic diagram of the process for manufacturing 5-decene from propene (a) disproportionation (b) fractionation (c) isomerization (d) fractionation (e) disproportionation (f) fractionation (g) isomerization (h) fractionation (i) disproportionation 0 fractionation (k) dimerization (1) fractionation. (From Ref. 17.)... 

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