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Journal of Energy Chemistry · 2023 · IF 13.1

Synthesis of straight-chain C49H100 alkane using a modular splicing strategy

Bing Ma,Jingqing Tian,Xueling Lang,Shutao Lei,Bolong Li,Chen Zhao

Ultra-long n -alkanes are highly valuable in both scientific research and as major constituents of specialty high-melting-point waxes. Unlike conventional methods (e.g., Fischer–Tropsch (FT), ethylene oligomerization, and polyethylene cracking) typically resulting in wide n -alkane distributions, the elaborate design strategy presented herein allows the direct synthesis of pure, long n -alkanes using a modular splicing method with acetone, furfural, and fatty acid anhydrides or acyl chlorides as bio-blocks. The herein approach is based on a simple four-step catalytic reaction scheme involving C–C chain elongation and C–O bond activation. The synthesized pure n -alkanes had a carbon chain length as high as C 49 (total yield of 49%). The synthesis approach also allows to selectively prepare n -alkanes with even and odd carbon numbers ranging from C 15 to C 49 . This process represents a great breakthrough in the synthesis of long-chain pure n -alkanes, surpassing the carbon number limitations reported in previous methodologies.

研究领域: 有机化学 · 材料科学 · 能源化学
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RAPID COMMUNICATIONS IN MASS SPECTROMETRY · 2010 ·Vol. 24 ·期 9 ·1335-1342 · IF 2.695

Determination of absolute photoionization cross-sections of alkanes and cyclo-alkanes

Zhongyue Zhou,Lidong Zhang,Mingfeng Xie,Zhandong Wang,Dongna Chen,Fei Qi

Absolute photoionization and dissociative photoionization cross-sections of eleven n- alkanes ( n- pentane, n -hexane, n- heptane, n- nonane, n- decane, n -undecane, n- dodecane, n- tridecane, n- tetradecane, n- pentadecane and n- hexadecane), three cyclo -alkanes (cyclopentane, methylcyclohexane and trans -decahydronaphthalene) and iso -octane were measured for photon energies from the ionization thresholds to 11.5 eV. The measurements were performed with the binary-liquid-mixture method utilizing the photoionization cross-sections of benzene as a calibration standard. The ionization energies of n -alkanes and cyclo -alkanes were also calculated at the B3P86/6-31 + +G(d,p) level and by the G3B3 method. Copyright © 2010 John Wiley & Sons, Ltd.

研究领域: 化学 · 物理化学
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RESEARCH ON CHEMICAL INTERMEDIATES · 2025 · IF 3.5

Development of Ni/HTA/Hβ alkane isomerization catalyst with improved selectivity for multi-branched isoalkanes

Zhu Lijun,Huang Guosheng,Liu Shuo,Jing Xiaohui,Yang Junwei,Xia Daohong

Isoalkanes are ideal gasoline components, and the isomerization reaction of light alkanes is the most effective way to increase the octane number of gasoline. Non-precious metal/zeolite catalysts are the mainstream bifunctional catalysts for alkane isomerization reactions, but there are still challenges in achieving high octane number components—multi-branched isoalkanes in isomerization reactions. In this article, Ni–heteropoly acid/zeolite alkane isomerization catalyst (Ni–HTA/Hβ) was prepared by impregnation method. Under optimized conditions, the conversion rate of n -hexane was 79.5%, the yield of isoalkanes was 78.7%, and the selectivity of isoalkanes was as high as 99.0%. In the product distribution, the Ni–HTA/Hβ catalyst can obtain more multi-branched isoalkanes, namely, 2,2-dimethylbutane and 2,3-dimethylbutane, with a total content of up to 19.2%, achieving the goal of further improving the yield of double-branched alkanes in C 6 alkane isomerization products.

研究领域: 催化化学 · 石油炼制 · 材料化学 · 工业化学 · 能源化学
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Processes · 2025 ·Vol. 13 ·期 11 ·3570 · IF 2.8

Volume Expansion Behavior of CO2 in Various Types of Hydrocarbon Systems Under Reservoir Conditions

Yu Zhang,Ziyang Zuo,Mingyuan Wang,Weifeng Lyu,Ke Zhang,Jiahao Gao

As a process fluid in oil reservoirs, carbon dioxide plays a dominant role in enhanced oil recovery by increasing volume and decreasing interfacial tension. To study the volume expansion behavior of a CO2–oil system under reservoir conditions, ten hydrocarbon components with carbon numbers ranging from 8 to 26 were selected to represent crude oil. Systems of CO2with normal alkanes, cycloalkanes, and aromatic hydrocarbons were measured using a self-assembled high-pressure visible cell, with a temperature range of 313.15 K to 353.15 K and a pressure up to 25 MPa. Experimental results demonstrate that pressure and temperature significantly influence the relative volumetric expansion behavior. The expansion rate exhibits a positive correlation with pressure, whereas it shows a negative correlation with temperature. Among different molecular configurations, normal alkanes exhibit the most pronounced swelling effect. This study establishes that the volumetric expansion behavior of crude oil under CO2exposure is predominantly governed by n-alkane components with carbon numbers less than 16. In the heavy hydrocarbon (carbon number > 16) and CO2system, the influence of hydrocarbon structure and carbon number on the expansion extent is considerably reduced. This paper delivers critical theoretical foundations for elucidating the microscopic interaction mechanisms in CO2enhanced oil recovery and optimizing injection parameter strategies.

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ChemSusChem · 2017 ·Vol. 10 ·期 20 ·4102-4108 · IF 7.226

Synthesis of Renewable Lubricant Alkanes from Biomass-Derived Platform Chemicals

Mengyuan Gu,Qineng Xia,Xiaohui Liu,Yong Guo,Yanqin Wang

Graphical Give grease a chance : Bio-based platform chemicals have not to date been exploited for the synthesis of highly branched lubricant alkanes. A selective catalytic synthetic route was developed for the production of highly branched C 23 alkanes as lubricant base oil components from biomass-derived furfural and acetone through a sequential four-step process in an overall carbon yield of approximately 50 %. The catalytic synthesis of liquid alkanes from renewable biomass has received tremendous attention in recent years. However, bio-based platform chemicals have not to date been exploited for the synthesis of highly branched lubricant alkanes, which are currently produced by hydrocracking and hydroisomerization of long-chain n -paraffins. A selective catalytic synthetic route has been developed for the production of highly branched C 23 alkanes as lubricant base oil components from biomass-derived furfural and acetone through a sequential four-step process, including aldol condensation of furfural with acetone to produce a C 13 double adduct, selective hydrogenation of the adduct to a C 13 ketone, followed by a second condensation of the C 13 ketone with furfural to generate a C 23 aldol adduct, and finally hydrodeoxygenation to give highly branched C 23 alkanes in 50.6 % overall yield from furfural. This work opens a general strategy for the synthesis of high-quality lubricant alkanes from renewable biomass.

CAS / MDL: 14898-67-0
研究领域: 化学工程 · 可再生能源 · 催化 · 生物化学
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INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH · 2016 · IF 2.567

Benzyl- and Vinyl-Functionalized Imidazoium Ionic Liquids for Selective Separating Aromatic Hydrocarbons from Alkanes

Fan Zhang,Yong Li,Lele Zhang,Zhiyong Zhou,Wei Sun,Zhongqi Ren

The separation of aromatics and aliphatic hydrocarbons is one of the most challenging and energy consuming operations in the petrochemical industry. In this study, two ionic liquids (ILs), N-benzyl-N-methylimidazoium bis(trifluoromethylsulfonyl)imide (IL-a) and N-benzyl-N-vinylimidazolium bis(trifluoromethylsulfonyl)imide (IL-b), were synthesized. Six ternary systems, i.e., toluene–heptane–IL (IL-a or IL-b), benzene–hexane–IL (IL-a or IL-b), and benzene–cyclohexane–IL (IL-a or IL-b), were studied in terms of both quantum chemical calculation and liquid–liquid extraction (LLE). The quantum calculation results showed that both ILs had stronger interaction with aromatics than that with alkanes. For both ILs, stronger binding energy was obtained with toluene than that with benzene. The liquid–liquid extraction experiments were conducted at 298.2 K and atmospheric pressure. The distribution coefficients of aromatic compounds (benzene and toluene) were over 0.72 when IL-a was used as extractant and above 0.75 when IL-b was used. When IL-a was used in the ternary system with benzene and hexane, the selectivity was more than 30, and the distribution coefficient of benzene was over 2.2. Both ILs could be reused more than 10 times without significant loss of selectivity and decrease of distribution coefficients. Better separation performance was obtained at 298.2 K than that at 318.2 K. Another three ternary systems with long-chain alkanes were also tested. Experimental LLE data of these studied ternary systems could be correlated adequately using the NRTL thermodynamic model.

研究领域: 化学工程 · 材料科学
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Soft Matter · 2017 ·Vol. 13 ·期 45 ·8636-8643 · IF 3.889

Interfacial rheological behaviors of inclusion complexes of cyclodextrin and alkanes

Ce Wang,Xulong Cao,Yangwen Zhu,Zhicheng Xu,Qingtao Gong,Lei Zhang,Lu Zhang,Sui Zhao

The transformation of cyclodextrins (CDs) and alkanes from separated monomers to inclusion complexes at the interface is illustrated by analyzing the evolution of interfacial tension along with the variation of interfacial area for an oscillating drop. Amphiphilic intermediates are formed by threading one CD molecule on one alkane molecule at the oil/aqueous interface. After that, the amphiphilic intermediates transform into non-amphiphilic supramolecules which further assemble through hydrogen bonding at the oil/aqueous interface to generate a rigid network. With the accumulation of supramolecules at the interface, microcrystals are formed at the interface. The supramolecules of dodecane@2α-CD grow into microrods which form an unconsolidated shell and gradually cover the drop. However, the microcrystals of dodecane@2β-CD are significantly smaller which fabricate into skin-like films at the interface. The amphiphilic intermediates during the transformation increase the feasibility of self-emulsification and the skin-like films enhance the stability of the emulsion. With these unique properties, CDs can be promising for application in hydrophobic drug delivery, food industry and enhanced oil recovery.

研究领域: 材料科学 · 药物传递系统 · 食品科学 · 石油工程
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ENVIRONMENTAL MICROBIOLOGY · 2022 ·Vol. 24 ·期 12 ·6307-6319 · IF 5.476

Wide distribution of the sad gene cluster for sub-terminal oxidation in alkane utilizers

Chao-Fan Yin,Ying Xu,Tao Li,Ning-Yi Zhou

Alkane constitutes major fractions of crude oils, and its microbial aerobic degradation dominantly follows the terminal oxidation and the sub-terminal pathways. However, the latter one received much less attention, especially since the related genes were yet to be fully defined. Here, we isolated a bacterium designated Acinetobacter sp. strain NyZ410, capable of growing on alkanes with a range of chain lengths and derived sub-terminal oxidation products. From its genome, a s econdary a lcohol d egradation gene cluster ( sad ) was identified to be likely involved in converting the aliphatic secondary alcohols (the sub-terminal oxidation products of alkanes) to the corresponding primary alcohols by removing two-carbon unit. On this cluster, sadC encoded an alcohol dehydrogenase converting the aliphatic secondary alcohols to the corresponding ketones; sadD encoded a Baeyer–Villiger monooxygenase catalysing the conversion of the aliphatic ketones to the corresponding esters; SadA and SadB are two esterases hydrolyzing aliphatic esters to the primary alcohols and acetic acids. Bioinformatics analyses indicated that the sad cluster was widely distributed in the genomes of probable alkane degraders, apparently coexisting (64%) with the signature enzymes AlkM and AlmA for alkane terminal oxidation in 350 bacterial genomes. It suggests that the alkane sub-terminal oxidation may be more ubiquitous than previously thought.

研究领域: 微生物学 · 环境科学 · 分子生物学
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Frontiers in Physiology · 2022 · IF 4.755

The role of tetradecane in the identification of host plants by the mirid bugs Apolygus lucorum and Adelphocoris suturalis and potential application in pest management

Yin Haichen,Li Wenjing,Xu Min,Xu Dong,Wan Peng

The mirid bugs Apolygus lucorum and Adelphocoris suturalis are considered serious pests of many crops in China, the host plant recognition of these pests remains unclear. The current study investigated the vital odor cues of two mirid bugs and evaluated the role of olfactory recognition in host recognition. The GC-EAD response of mirid bugs to volatiles of their host plant Phaseolus vulgaris was tested. Tetradecane, 2-propyl-1-pentanol, and dodecanal elicited strong EAG responses by mirid bugs and were tested with field experiments. The results indicated tetradecane was significantly more attractive than other attractants, yielding 30.33 ± 2.19 mirid bugs trapped during 7 days. The selected response rates to tetradecane were above 60%, which was most attractive to female A. lucorum at 1.5 mg/ml. Among seven tetradecane derivatives, tetradecane and tetradecanoic acid were the most potent attractants to A. lucorum and A. suturalis. Tetradecane was present in the volatiles of 10 common hosts, and their difference in relative content was significant. The presence of tetradecane seemed relevant to the olfactory response intensity of two mirid bugs towards the different host plants. The artificial supplement of tetradecane increased the attractive effect of host plants. These results suggested that tetradecane plays a vital role in the olfactory selection by two mirid bugs, and it can be made into field baits as a novel ecological strategy to manage these pests with widely reported pesticide resistance. However, results suggested host recognition is not entirely dependent on odor cues. We demonstrated that A. suturalis and A. lucorum adults have similar olfactory recognition mechanisms to their hosts in long-distance host selection. While, the differences in host plant selection between the two pests should occur in close range due to differences in gustatory or tactile sensory organs of A. lucorum and A. suturalis.

研究领域: 昆虫学 · 生态学 · 农业科学
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ACS Sustainable Chemistry & Engineering · 2015 · IF 4.642

One-Pot Catalytic Conversion of Raw Lignocellulosic Biomass into Gasoline Alkanes and Chemicals over LiTaMoO6 and Ru/C in Aqueous Phosphoric Acid

Yong Liu,Lungang Chen,Tiejun Wang,Qi Zhang,Chenguang Wang,Jinyue Yan,Longlong Ma

Lignocellulosic biomass is a renewable feedstock that has the potential to replace the diminishing fossil fuels. Herein, we reported the simultaneous conversion of cellulose, hemicellulose and lignin from raw biomass into gasoline alkanes (hexanes and pentanes) and monophenols and related hydrocarbons over layered LiTaMoO6 and Ru/C in aqueous phosphoric acid medium. Specifically, gasoline alkanes were directly yielded from the carbohydrate components, based on hemicellulose and cellulose, and the total yield could be up to 82.4%. Notably, the lignin fraction could also be transformed into monophenols, related alcohols and hydrocarbons by the one-pot reaction. It suggested that the hydrocracking of monophenol fraction could be performed in this catalytic system. The total yield of volatile products was 53% based on the lignin fraction. In this paper, the influences of phosphoric acid concentration, substrate ash and the amino acids derived from the biogenic impurities were investigated and different raw biomass substrates were tested. Furthermore, the catalysts could be reused for several runs to convert raw biomass without pretreatment.

研究领域: 能源生物学 · 催化化学
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FOOD CHEMISTRY · 2020 · IF 6.306

Cuticular wax composition changes of 10 apple cultivars during postharvest storage

Yifeng Chai,Ang Li,Su Chit Wai,Congcong Song,Yaoyao Zhao,Yuquan Duan,Baiqing Zhang,Qiong Lin

Cuticular wax chemicals differ among fruit cultivars and contribute to storage ability. However, wax analysis in apple cultivars, particularly during storage, has not been described. In this work, the chemicals and crystal structures of cuticular wax in 10 apple cultivars were analyzed to observe wax functions in apple during storage. Results showed that alkanes and primary alcohols decreased while fatty acids increased in stored fruits of all cultivars compared with the fruits before storage. Terpenoids , aldehydes, and phenols were observed in stored fruits but not in the fruits before storage in all cultivars except ‘Red Star’ fruit. The weight loss rate was significantly correlated with six components including C13 alcohol, C14 alkanes, total alkanes, total wax, C13 alkanes and C54 alkanes in 10 cultivar apple fruits during storage. Our findings indicate that the total wax, particularly alkanes, in the peel of apple fruits is essential for storage and quality control.

CAS / MDL: 25561-30-2 67-66-3
研究领域: 植物学 · 食品科学
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JOURNAL OF CHEMICAL THERMODYNAMICS · 2015 · IF 2.679

(Liquid + liquid) extraction of methanol from alkanes using dialkylphosphate-based ionic liquids as solvents

Fufeng Cai,Guomin Xiao

In this work, the feasibility of ionic liquids (ILs), 1,3-dimethylimidazolium dimethylphosphate ([MMIM][DMP]), 1-ethyl-3-methylimidazolium diethylphosphate ([EMIM][DEP]), and 1-butyl-3-methylimidazolium dibutylphosphate ([BMIM][DBP]), as solvents for the extraction of methanol from its mixtures with hexane and heptane was analyzed. The knowledge of (liquid   +   liquid) equilibria (LLE) of these mixtures is necessary for the design of the extraction separation process. Hence, the LLE data for the ternary systems, {methanol   +   hexane   +   ([MMIM][DMP], or [EMIM][DEP], or [BMIM][DBP])}, and {methanol   +   heptane   +   ([MMIM][DMP], or [EMIM][DEP], or [BMIM][DBP])}, were measured at T   =   298.2   K and atmospheric pressure. The experimental results were correlated with the thermodynamic nonrandom two-liquid (NRTL) model. The solute distribution ratios of methanol and methanol/alkane selectivities, derived from the experimental LLE data, were calculated and analyzed to evaluate the capability of the studied ILs to accomplish the separation target. Meanwhile, these capabilities were also compared with that of other ILs obtained from the literature.

CAS / MDL: 142-82-5 71-23-8
研究领域: 化学工程 · 材料科学
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