Applications of light olefin oligomerization to the production of fuels and chemicals

Nicholas, Christopher P.

doi:10.1016/j.apcata.2017.06.011

Cited by 129 publications

(95 citation statements)

References 231 publications

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“…The reaction mechanism for butene oligomerization is obey classical carbenium ion mechanisms [23]. Figure S1 illustrates the typical step of the Reaction scheme in butene oligomerization.…”

Section: Catalytic Performancementioning

confidence: 99%

Improvement of the Catalytic Efficiency of Butene Oligomerization Using Alkali Metal Hydroxide-Modified Hierarchical ZSM-5 Catalysts

Zhang

et al. 2018

Catalysts

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Oligomerization of light olefin is an effective method to produce plentiful liquid fuels. However, oligomerization processes using microporous zeolites have severe problems due to steric hindrance. In this paper, oligomerization of butene using a series of new types of hierarchical HZSM-5 zeolite catalysts is studied. To obtain the modified HZSM-5 catalysts, HZSM-5 is treated with the same concentration of LiOH, NaOH, KOH, and CsOH aqueous solutions, respectively. It is demonstrated that the alkali treatment can effectively modify the acidity properties and hierarchical structure of the HZSM-5 catalyst, which is confirmed by X-ray Diffraction (XRD), X-ray Fluorescence (XRF), Nitrogen Adsorption-desorption Measurements, Transmission Electron Microscopy Investigations (TEM), Ammonia Temperature-programmed Desorption Method (NH 3 -TPD), Pyridine FT-IR, and Thermogravimetric Analysis (TGA). The results show that hierarchical catalysts with interconnected open-mesopores, smaller crystal size, and suitable acidity can better prolong the catalyst lifetime during butene oligomerization. Particularly, the HZSM-5 catalysts treated with CsOH aqueous solution (ATHZ5-Cs) proved to be the most effective catalyst, resulting in approximately 99% conversion of butene and exhibiting C 8 + selectivity of 85% within 12 h. Thus, an appropriate hierarchical catalyst can satisfy the oligomerization process and has the potential to be used as a substitute for the commercial ZSM-5 catalyst.

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“…The reaction mechanism for butene oligomerization is obey classical carbenium ion mechanisms [23]. Figure S1 illustrates the typical step of the Reaction scheme in butene oligomerization.…”

Section: Catalytic Performancementioning

confidence: 99%

Improvement of the Catalytic Efficiency of Butene Oligomerization Using Alkali Metal Hydroxide-Modified Hierarchical ZSM-5 Catalysts

Zhang

et al. 2018

Catalysts

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“…Dimerization of 1-pentene:1 -Pentene (0.252 g, 3.2 mmol), 87 % conversion. 1 Oligomerization of isoprene:I soprene (0.218 g, 3.2 mmol), 70 % conversion. Ac omplex mixture of dimers, trimers and tetramers was obtained ( Figure S4).…”

Section: Generalc Atalytic Proceduresmentioning

confidence: 99%

“…The catalytic oligomerization of short-chain olefinsi sap owerful method for the generationo fs ynthetic paraffinic kerosenes (SPKs) that have applicationsa sa lternative jet and diesel fuels. [1] Short-chain olefins including ethylene, propylene, butenes, 1-hexene, and isoprene are readily availablef rom biomass sources and can be converted into SPKs by highthroughput catalytic routes. [2][3][4][5] Renewable alcohols such as ethanol, n-butanol, [6][7][8] 2,3-butanediol, [9] isobutanol, [10][11][12] methyl butenols, [13] 1-pentanol, [14] and 1-hexanol [15] can be generated by fermentation of biomass sugars and then dehydrated to generate alkene substrates.…”

Section: Introductionmentioning

confidence: 99%

“…Mixed coupling of isoprene/1-hexene/1-pentene (2:1:1):Isoprene (0.109 g, 1.6 mmol), 1-pentene (0.056 g, 0.82 mmol), and 1-hexene (0.068 g, 0.82 mmol), 80 %c onversion 1. HNMR (CDCl 3 ): d = 5.21-5.13 (m, CH 2 ), 4.74-4.65 (m, CH 2 ), 4.60 (bs), 2.73-2.54 (m, CH), 2.27-2.14 (m, CH 2 ), 2.14-1.95 (m, CH), 1.72 (bs, CH 3 ), 1.68 (bs), 1.64 (bs), 1.62 (bs), 1.51-1.36 (m, CH 2 ), 1.36-1.11( m, CH 2 ), 0.95-0.81 ppm (m, CH 3 ); GC-MS (ESI): m/z calcd for C 10 H 18 ,C 11 H 20 :1 38, 152; found:138, 152.…”

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confidence: 99%

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High‐Performance Jet Fuels Derived from Bio‐Based Alkenes by Iron‐Catalyzed [2+2] Cycloaddition

2019

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A series of high‐performance cycloparaffinic fuels have been generated by [2+2] cycloaddition of the bio‐derived alkenes 1‐hexene, isoprene, and 1‐pentene, catalyzed by a low‐valent iron pyridine(diimine) complex [(MePDI)Fe(N2)2(μ‐N2)] [MePDI=N,N′‐(2,6‐pyridinediyldiethylidyne)bis(2,6‐dimethylbenzenamine)]. Reactions with 1‐pentene and 1‐hexene resulted in 85 % selectivity to 1,2‐cyclobutanes, and 12 % selectivity to acyclic alkenes generated by β‐hydride elimination. Self‐dimerization of isoprene was sluggish and generated heavier oligomer products, but cross‐dimerization of isoprene with 1‐hexene afforded primarily a 1,3‐cyclobutane product, along with isomers of acyclic C11 mixed dimers. Hydrocarbon mixtures were hydrogenated and fractionally distilled to yield finished fuel mixtures in overall yields of 83–93 % at the multigram scale. The fuels exhibited densities ranging between 0.767 and 0.783 g mL−1, and net heats of combustion (NHOC) of up to 120.6 kBtu gal−1 (43.8 MJ kg−1). These values are higher than conventional synthetic paraffinic kerosenes owing to the higher density and ring strain afforded by the cyclobutane rings. The fuel mixtures also exhibited extremely low viscosities ranging from 2.38 to 4.78 mm2 s−1 at −20 °C, due in part to the presence of the acyclic dimers. The excellent fuel properties of the product mixtures, selectivity for dimer products, high yields, and the ability to use simple bio‐derived alkenes as substrates, make the [Fe]‐catalyzed [2+2] cycloaddition of unactivated alkenes a compelling route to the synthesis of sustainable high‐performance fuels.

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“…The oligomerisation of light olefins, such as ethene, propene and butenes, represents an attractive route to produce ecofriendly synthetic fuels with low content of aromatics and sulphur, and added value chemicals such as dyes, plasticizers and detergents. [1,2] Olefin oligomerisation technologies were firstly commercialized by Universal Oil Products (1930), namely the CatPoly technology [3,4] using solid phosphoric acid (SPA) as catalyst to produce gasoline and diesel range products from propene/butene mixtures (Scheme 1). Overcoming environmental and technical drawbacks associated with SPA, the MOGD (1980) [5][6][7] and COD (1992) [8,9] technologies were developed using crystalline microporous aluminosilicates possessing the MFI topology to produce high quality distillate fuels (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

Catalytic Conversion of 1‐butene over Modified Versions of Commercial ZSM‐5 to Produce Clean Fuels and Chemicals

et al. 2019

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The oligomerisation of light olefins, obtainable from fossil/renewable sources and refinery streams, is an attractive route to produce clean synthetic fuels and added‐value chemicals. ZSM‐5 is a type of catalyst used in commercial olefin oligomerisation processes. Using appropriate modification procedures, it was possible to prepare catalysts with improved performances. Various modified versions of commercially available ZSM‐5 were prepared and investigated for 1‐butene oligomerisation under high‐pressure, continuous‐flow operation (30 bar, 200 °C). Simple, up‐scalable top‐down strategies involving base‐acid treatments of ZSM‐5 led to catalysts possessing enlarged pores and the required acidity for converting 1‐butene to higher molar mass products. In targeting diesel type products, the modified catalysts led to up to 86 % butenes conversion, space time yield of 852 mg gcat−1 h−1 and mass ratio diesel:naphtha cuts of 2.2. Characterisation studies and multivariate/principal component analysis helped categorise the differently prepared catalysts, and gain insights into complex interplay of material properties influencing the catalytic reaction.

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Applications of light olefin oligomerization to the production of fuels and chemicals

Cited by 129 publications

References 231 publications

Improvement of the Catalytic Efficiency of Butene Oligomerization Using Alkali Metal Hydroxide-Modified Hierarchical ZSM-5 Catalysts

Improvement of the Catalytic Efficiency of Butene Oligomerization Using Alkali Metal Hydroxide-Modified Hierarchical ZSM-5 Catalysts

High‐Performance Jet Fuels Derived from Bio‐Based Alkenes by Iron‐Catalyzed [2+2] Cycloaddition

Catalytic Conversion of 1‐butene over Modified Versions of Commercial ZSM‐5 to Produce Clean Fuels and Chemicals

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