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The effect of the molecular structure of feedstock on the cracking reaction of C10 hydrocarbons to ethylene and propylene over H-ZSM-5 zeolite was investigated. To better compare the effect of decane on the production of light olefins, the thermal cracking and catalytic cracking performance of decane were first investigated. As a comparison, the thermal cracking and catalytic cracking of decane were studied by cracking over quartz sand and H-ZSM-5. Compared with the thermal cracking reaction over quartz sand, the catalytic cracking reaction of decane over H-ZSM-5 has a significantly higher conversion and light olefins selectivity, especially when the reaction temperature was lower than 600 °C. On this basis, the catalytic cracking reactions of decane and decene over H-ZSM-5 were further compared. It was found that decene with a double bond structure had high reactivity over H-ZSM-5 and was almost completely converted, and the product was mainly olefin. Compared with decane as feedstock, it has a lower methane yield and higher selectivity of light olefins. Therefore, decene was more suitable for the production of light olefins than decane. To this end, we designed a new light olefin production process. Through olefin cracking, the yield of light olefins in the product can be effectively improved, and the proportion of different light olefins such as ethylene, propylene and butene can be flexibly adjusted.

Covering: 2000 to 2020. trans-Bicyclo[4.4.0]decane/decene (such as trans-decalin and trans-octalin)-containing natural products display a wide range of structural diversity and frequently exhibit potent and selective antibacterial activities. With one of the major factors in combatting antibiotic resistance being the discovery of novel scaffolds, the efficient construction of these natural products is an attractive pursuit in the development of novel antibiotics. This highlight aims to provide a critical analysis on how the presence of dense architectural and stereochemical complexity necessitated special strategies in the synthetic pursuits of these natural trans-bicyclo[4.4.0]decane/decene antibiotics.

A two-carbon bridged diphosphine (PCCP) ligand bearing an ortho-methoxy substituent in the phosphine phenyl group has been synthesised and applied in Cr-catalysed ethylene oligomerization. Compared to previous catalysts, the Cr catalytic system exhibited a higher selectivity toward the C10 fraction of up to 28.4 wt%, achieving a high reactivity of up to 1530 kg/(g Cr/h). The major product produced by the Cr/PCCP catalyst is 1-hexene with a selectivity of 64.1%. A detailed theoretical investigation by DFT calculations on the co-trimerization of ethylene and 1-hexene shows that the coordination of the oxygen atom of a methoxy moiety to the chromium center might be a key factor for the highly selective formation of 1-hexene. Moreover, the calculation results are consistent with the experimental observations on the distribution of decene isomers.

Tungstate catalysts are well established for olefin epoxidation reactions, while their catalytic activity for CO2 insertion in epoxides is a more recent discovery. This dual reactivity of tungstate prompted the present development of a catalytic tandem process for the direct conversion of olefins into the corresponding cyclic organic carbonates (COCs). Each of the two steps was studied in the presence of the ammonium tungstate ionic liquid catalyst – [N8,8,8,1]2[WO4] – obtained via a benign procedure starting from ammonium methylcarbonate ionic liquids. The catalytic epoxidation first step was optimised on 1-decene as model substrate, using H2O2 as benign oxidant, [N8,8,8,1]2[WO4] as catalyst and phosphoric acid as promoter affording quantitative conversion with 92% selectivity towards decene oxide. Unfortunately, the addition of CO2 from the start (auto-tandem catalysis) gave low yields of decene carbonate (

Significant progresses have been made in the performance of homogeneous catalysts in the oligomerization of 1-decene to polyalphaolefin (PAO), whereas it remains a big challenge to design heterogeneous catalysts with high catalytic activity in the PAO synthesis. Herein, a series of heterogeneous mesoporous catalysts with different acidity were successfully synthesized by the in situ incorporation of Al in the channels of mesoporous silica under room temperature and atmospheric pressure. These samples were characterized by various techniques including XRD (X-ray diffraction), SEM (scanning electron microscopy), TEM (transmission electron microscopy), BET (N2 adsorption–desorption analyses), Py-IR (pyridine-adsorbed IR) and XPS (X-ray photoelectron spectroscopy). The obtained samples exhibit a high surface area, high ordering, and controllable Bronsted and Lewis acid sites. The results indicated that the increasing acidity promotes oligomer selectivity, especially for the trimer (C30). The resulting heterogeneous catalyst exhibited excellent performance with high conversion (70.7%) and high oligomer selectivity (96.7%) due to the suitable acid sites. Moreover, the spent heterogeneous catalyst could be regenerated and its catalytic activity maintained after five cycles.

Linear alkylcresols were synthesized in high yield by the alkylation of m-cresols with 1-decene in the presence of 25%HPW/SBA-15 catalyst. The physicochemical properties of the catalyst were investigated by means of N2 adsorption/desorption measurements (textural properties: surface area, pore volume and average pore diameter) and thermal desorption of diethyl-amine (acidity and the acid strength distribution). HPW-loaded acid as well as the SBA-15 support displayed a mesoporous structure. The effects of the reaction time and the catalyst amount on the reaction were studied. The main monitored parameters were the conversion of m-cresol, yield of decylcresol isomers (ortho- and para-) and yield of polyakylated cresol. The results indicates that 25%HPW/SBA-15 catalyst has high catalytic activity, with the m-cresol conversion of 93.8% , at 160 °C with a reaction time of 150 min and a catalyst loading of 0.5 wt% m-Cresol was alkylated preferably in the para-position, the yield of 4-(decan-2yl)-3-methylphenol, after 150 min reaction time was 54.5%.

Comparative studies (gel permeation chromatography and evaluation of turbulent drag reduction effectiveness on a turbulence rheometer) of ultra-high molecular weight polymers from a series of higher alpha-olefins (hexene, octene, decene, dodecene) used as hydrodynamic drag agents have been carried out. It was found that the activity of hexene in the polymerization on a titanium magnesium catalyst, if all other relevant factors remain unaltered, significantly exceeds the activity of octene, decene, and dodecene (the conversion of hexene in 24 h is almost 1.5 times higher than the conversion of other monomers over the same time), and the rates of polymerization of the latter differ slightly. The average molecular weights of all polymers differ only slightly: ~6 millions Da for polyhexene and ~5 millions Da for all the others. At the same time, the drag reduction effectiveness of the polymers showed a significant dependence on the nature of the initial monomers: the drag reduction effectiveness rapidly diminishes with an increase in the molecular weight of the corresponding alpha-olefin (3–4 times upon transition from polyhexene to polydodecene).

Progress toward a convergent approach for the enantioselective synthesis of the Veratrum alkaloid jervine is presented. The two requisite fragments were stereoselectively and efficiently fashioned from economical and readily available reagents. Key reactions include (a) a highly diastereoselective Ireland—Claisen rearrangement to establish the necessary cis-relationship between the amine and methyl group on the tetrahydrofUran E-ring; (b) a diastereoselective selenoetherification reaction that enabled the assembly of the D/E oxaspiro [4.5] decene in the needed configuration; and (c) an enzymatic desymmetrization of an abundant achiral diol en route to a key four-carbon building block as a practical alternative to a protected Roche ester reduction.

Cyclic carbonate compounds are valuable for a range of applications and can be synthesized by a one-pot reaction involving epoxidation of olefin followed by reaction of the epoxide with CO2. This study used supported ruthenium catalysts for the epoxidation step (first step), where a combination of tetrapropylammonium bromide and zinc bromide was used for the cycloaddition of carbon dioxide. The supported ruthenium catalyst, prepared by a sol-immobilization method, allowed the effective epoxidation of 1-decene in air (using oxygen as the main oxidant) at 90 ºC in the presence of a catalytic quantity of radical initiator. This approach was applied to the one-pot multi-step oxidative carboxylation of 1-decene in the presence of 1 % Ru/support-Pr4NBr/ZnBr2 catalyst

In this paper, poly-α-olefins oil base stocks with medium kinematic viscosity and high viscosity index were prepared by 1-decene oligomerization catalyzed using the alkylaluminum chloride catalyst ...

A Ti-based diamine bis(phenolate) catalyst, [Ti{2,2′-(OC6H2-4,6-tBu2)2NHMePhMeNH}Cl2], was synthesized and fully characterized by elemental analysis and NMR spectroscopy. Very effective, fast, and reversible chain transfer was achieved between an active transition metal-based propagating center and diethylzinc, which acted as a chain transfer agent, in the coordinative chain transfer polymerization (CCTP) of 1-decene. The molecular weight of the obtained oligomers was efficiently regulated and decreased by the addition of ZnEt2 to the oligomerization system. The kinetic results disclosed that ZnEt2, besides its primary role as a chain transfer agent, also significantly reduced the catalyst consumption. DFT calculations were performed to reveal the reaction mechanism. Notably, the CCTP technique led to the occurrence of fast and reversible chain transfer, bypassing the β-H termination pathway, so oligomer chains without any unsaturated bonds were obtained. Finally, a linear relationship between the ZnEt2 content and the tacticity characteristic of the resulting oligomers was detected. The viscosity results showed that the obtained oligomers had a viscosity index in the range of 131.7–159.7 and pour point values less than −48 °C, which were comparable with the properties of commercial polyalfaolefin-based oils. Our proposed green approach for producing low viscosity polyalphaolefins (PAO4 and PAO6) can replace the industrially-used and hazardous BF3 catalyst system with great success.

The BF3/n-BuOH complexes were investigated as active species in catalyzing n-decene polymerization reaction. The structures of BF3/n-BuOH complexes were characterized not only by modern spectrum but also by calculation at theoretical level. The results confirmed that BF3/n-BuOH complexes changed from BF3·(n-BuOH)2 complexes to BF3·n-BuOH complexes with the mass fraction of BF3 increasing. These two complexes have different catalytic activity, but BF3·n-BuOH was superior. The highest n-decene conversion could reach 99% and the most excellent selectivity of n-decene trimer and tetramer could reach up to 80% yield by a series of controlled conditions. This work can help to understand the catalytic active species of n-decene polymerization and provide support for industrialization of poly-alpha-olefins (PAOs).

A series of α-diimine nickel complexes bearing para-benzhydryl groups, {[(2,6-R2-4-CHPh2C6H2N = C)2Nap]NiBr2, Nap: 1,8-naphthdiyl, R = Me (C1); R = Et (C2); R = iPr (C3)}, were synthesized and characterized. Upon activation with AlEt2Cl, these para-benzhydryl substituted catalysts conducted the ethylene and 1-decene polymerizations via controlled chain-walking process. These nickel complexes exhibited good thermal stability and high activities (up to 106 g PE (mol Ni h)−1) towards ethylene polymerization, producing high molecular weight polyethylenes with a relatively low degree of branching and narrow polydispersities (Mw/Mn ≤ 2.01). The catalytic activities [(0.81–2.42) × 106 g PE (mol Ni·h)−1], polyethylene molecular weights [Mn: (7.9–29.3) × 104 g mol−1] and total branching densities (57–102/1000C) can be tuned over a wide range. These controlled branching degrees of the obtained polyethylenes were decreased with increasing the bulkiness of the ligand and decreasing the polymerization temperature. Polymerization of 1-decene using these cationic nickel complexes generated branched poly(1-decene)s (69–87/1000C) with high molecular weights and narrow polydispersities (Mw/Mn = 1.18–1.55).

Homo- and copolymers of propylene and 1-decene were synthesized by controlled chain-walking (co)polymerization using phenyl substituted &alpha, diimine nickel complexes activated with modified methylaluminoxane (MMAO). This catalytic system was found to polymerize propylene in a living fashion to furnish high molecular weight ethylene-propylene (EP) copolymers. The copolymerizations proceeded to give high molecular weight P/1-decene copolymers with narrow molecular weight distribution (Mw/Mn &asymp, 1.2), which indicated a living nature of copolymerization at room temperature. The random copolymerization results indicated the possibility of precise branched structure control, depending on the polymerization temperature and time.

For the first time, randomly methylated β-cyclodextrin was applied as the mass transfer agent in a continuous process. Considering the example of the Rh-catalyzed hydroformylation of 1-decene, process development was shown, where cyclodextrin was used together with a catalyst system that was continuously recovered and recycled using an aqueous biphasic system. In initial experiments, water-soluble and commercially available Rh/TPPTS and Rh/sulfoxantphos catalyst systems were scaled up from 50 ml into 1000 ml high-pressure autoclave systems to demonstrate their scalability. Both these systems were compared, and they afforded excellent chemoselectivity (>99%) toward the desired linear aldehyde product. In particular, higher regioselectivity (up to 31) was achieved for the Rh/sulfoxantphos system. Investigations regarding the long-term stability of the mass transfer agent and both catalyst systems were carried out in a continuously operated miniplant process. It was shown that the process could be successfully operated under the steady state for over 200 h with chemoselectivity of >97% toward the desired aldehyde product. Simultaneously, extremely low Rh leaching (total: 0.59%) was observed over the entire period of 200 h.

1-Phenylphosphol-2-ene 1-oxide is effectively resolved by L-menthyl bromoacetate to afford both SP and RP enantiomers of 1-phenylphosphol-2-ene 1-oxide on a multigram scale. The resolved 1-phenylphosphol-2-ene oxide has been found to undergo face-selective and endo-selective cycloadditions with a series of acyclic and cyclic dienes to produce enantiopure P-stereogenic C-P heterocycles of hexahydrophosphindole and hexahydrobenzophosphindole as well as phospha[5 .2.1.02,6]decene and phospha[5.2.2.02,6]undecene structures. Conversions of these cycloadducts to the fully saturated heterocyclic systems as well as to their P (III), P = S, P = Se and P-BH3 derivatives have been demonstrated to occur with retention of configuration and preservation of configurational homogeneity at P. A perplexing case of stereomutation at P during reduction of a tricyclic &beta, hydroxy phosphine oxide by PhSiH3 at 80 &deg, C has been recorded.

Spectrokinetic measurements have shown that in the reaction media benzene – decene-1 and toluene – decene- 1 at a temperature of 80 °C and helium pressures of 0.2-0.3 MPa, Al-Cu alloys activated with a liquid Ga-In eutectic at a temperature of 150 °C for 2 h in vacuum, 1.2 times more reactive with respect to a 4-fold molar excess of CCl4 than Al- Cu alloys activated with liquid Ga-In eutectic at a temperature of 24 °C for 36 h in air. Activated Al-Cu alloys are 1.4 times more reactive with respect to CCl4 in a toluene – decene-1 reaction medium than in a benzene – decene-1 reaction medium. A comparison of the catalytic studies with the structure of the metal chloride complexes formed in situ has been carried out. Using infrared spectroscopy and UV-visible spectrophotometry, it was found that benzene – decene-1 in the reaction medium at a temperature of 80 °C and helium pressures of 0.2-0.3 MPa from Al-Cu alloys activated by liquid Ga-In eutectic at a temperature of 24 °C for 36 h in air, and a 4-fold molar excess of CCl4, ionic complexes (C6H5)3C+ − [AlCl4]− are formed, which are predominantly active in the catalytic reaction of benzene alkylation with decene-1. Under identical conditions, molecular complexes of AlCl3 with organochlorine hydrocarbons, which are predominantly catalytically active in the decene-1 telomerization reaction, are formed from Al-Cu alloys activated with liquid Ga-In eutectic at a temperature of 150 °C for 2 h in vacuum, and a 4-fold molar excess of CCl4. The activity of ionic complexes is 2.1 times higher than that of molecular ones. In the reaction medium toluene – decene-1, regardless of the conditions of activation of Al-Cu alloys by liquid Ga-In eutectic, molecular complexes of Al2Cl6 with organochlorine hydrocarbons are formed in situ, which are catalytically active both in the telomerization reaction of decene-1 and in the alkylation of toluene with decene-1. The activity of the complexes obtained from Al-Cu alloys activated by liquid Ga-In eutectic at a temperature of 150 °C for 2 h in vacuum is 23.8 times higher.

Polyα-olefin oil (PAO) was synthesized via cationic oligomerization of 1-decene as monomer, aluminum chloride as catalyst, ethanol as coactivator and toluene as solvent. Oligomer product was fractionated by distillation in vacuum and each fraction was characterized using viscometry, HNMR and GPC techniques. Analyses results showed that the fractions with higher boiling point and molecular weights had lower aromatic contents and higher viscosity index (VI).

In this research, poly1-decene was synthesized by Silica/AlCl3/H2O catalytic system in the presence as well as absence of toluene as a solvent. The effect of solvent amount on the final product properties was explored. The obtained oligomers were characterized with GPC, TGA, Kinematic Viscosity at 40 and 100 ℃ (KV40, KV100), Viscosity Index (VI) and 1H NMR methods. The results showed that the molecular weight and kinematic viscosity of 1-decene oligomer decreased as the toluene amount increased. TGA analysis demonstrated that thermal stability of the synthesized oil decreased in the poly1-decene samples synthesized in the presence of toluene. 1H NMR spectroscopy revealed the presence of aromatic ring in the structure of oligomer chains synthesized in the presence of toluene while that for the chains without solvent, the characteristic peaks of aliphatic and alkene type hydrogens were detected.

The liquid phase oligomerization reaction of 1-decene to produce dimers and trimers was performed in a semi-batch autoclave reactor over a tungstated-zirconia catalyst at different reaction temperatures. While dimers can be used as a synthetic transportation fuel, trimers and higher compounds can be used as a base oil which can be blended with additives to make synthetic base oil. The conversion of 1-decene increased from 9 to 70% as the reaction temperature was increased from 423 to 483 K. At 483 K, product compositions after 11 h consisted of 50% dimers and 23% trimers. Apparent activation energies for dimerization and trimerization were found to be 21.0 ± 0.5 and 33.0 ± 0.6 kJ/mol, respectively. Kinetic interpretation has been made by studying the kinetic and equilibrium constants. The results of the oligomerization of 1-decene suggest that two active sites are responsible for dimerization. Trimerization proceeds through a combination of dimer with another monomer involving three active sites. According to the mathematical equation, an increase in active sites required for both reactions at higher temperature is necessary to compensate for catalyst deactivation.

Several new solid oxo-rhenium and oxo-molybdenum catalysts were tested for the deoxydehydration (DODH) of 1,2-diols to terminal olefins employing aromatic solvents and reaction temperatures of 150–200 °C. A catecholato oxo-rhenium catalyst tethered to silica was prepared and found to have comparably high DODH activity to its soluble analog with triphenylphosphine as the reductant. Catalyst re-use and leach-test experiments show significant leaching into the liquid phase. Silica, ceria and, for the first time, alumina and iron oxide were tested as supports for perrhenate, with ceria producing the least active material in 1,2-decane diol DODH. Decene yields obtained with ReOx/SiO2, ReOx/Fe2O3, ReOx/Al2O3 were highest when triphenylphosphine was the reductant and reached 70 − 78% (at 90–100% conversion) at 150 °C. These three catalysts were also effective with gaseous reductants H2 or CO. Leaching of rhenium species occurred for all supports and was most pronounced for SiO2. New solid oxo-molybdenum catalysts were synthesized. At 200 °C, decene yields observed using MoOx/Fe2O3, MoOx/SiO2, MoOx/Al2O3, MoOx/TiO2 and MoOx/ZrO2 were comparable and did not exceed 20%. There were homogeneous contributions through leached molybdenum species.

Immobilization of active components on support materials is an effective strategy to minimize the negative environmental and health impacts of hazardous Lewis acid catalysts. In this study, we synthesized immobilized Al–Ti bimetallic catalysts supported on MgO–Al2O3–SiO2 ternary oxide (Al–Ti/MAS) with accurately controlled compositions and pore structures. We also characterized supports and catalysts using various techniques. Further, we examined their catalytic activity and stability using a fixed-bed reactor. Compared with γ-Al2O3-derived catalyst, the Al–Ti/MAS catalysts feature more Lewis acid sites and better pore structure accessibility, which lead to much higher activity and stability. Among these MAS samples, M-3 (Si/Al molar ratio = 9.76) presents the highest loading of active species with a chlorine content of 16.7%, leading to the highest PAO yield of 94.6% and the best stability. In addition, the deactivation of the MAS-derived Al–Ti bimetallic catalysts is mainly ascribed to the loss of activ...

The authors acknowledge the KAUST ACL Core Lab. This work was supported by funds from King Abdullah University of Science and Technology

Described herein is a synthetic strategy for the total synthesis of (±)-phomoidride D. This highly efficient and stereoselective approach provides rapid assembly of the carbocyclic core by way of a tandem phenolic oxidation/intramolecular Diels-Alder cycloaddition. A subsequent SmI2 -mediated cyclization cascade delivers an isotwistane intermediate poised for a Wharton fragmentation that unveils the requisite bicyclo[4.3.1]decene skeleton and sets the stage for synthesis completion.

The synthesis of propellanes containing bicyclo[2.2.2]octene via olefin metathesis approach is less explored. Herein, we describe a simple and convenient method to synthesize propellane derivatives containing a bicyclo[2.2.2]octene unit which are structurally similar to 11β-HSD1 inhibitors by sequential usage of the Diels–Alder reaction, C-allylation and ring-closing metathesis (RCM) as the key steps. Additionally, we expanded this approach to an endo-tricyclo[4.2.2.02,5]decene derivative which is a useful monomer for polymer synthesis and we have also synthesized basketene and anthracene-based propellanes using the same strategy.

An original approach to α-olefin oligomerization as well as novel thermally stable zirconocene catalysts for use in such reactions has been elaborated. The method reported allows the achievement of fractions of lightweight α-olefin oligomers up to 90% yields without considerable formation of byproducts like internal alkenes, alkanes, and higher oligomers. Trimers, tetramers, and pentamers of 1-hexene, 1-octene, and 1-decene were isolated as individual compounds and were hydrogenated. Viscosity characteristics of the isolated saturated and unsaturated hydrocarbons have been studied at various temperatures. The isolated saturated oligomers of 1-octene and 1-decene outperform the traditional electrophilic oligomerization products in terms of viscosity indexes, pour points, and low-temperature viscosity.

A promising production route for a high-quality base stock for lubricants is the oligomerization of high molecular-weight olefins in a high energy efficiency system. Oligomerization of 1-decene (C10) was conducted in a microwave-assisted system over a HY zeolite catalyst at different reaction temperatures and times. Higher reaction temperature resulted in increasing formation of dimers and trimers. The oligomerization reaction yielded 80% conversion, 54.2% dimer product, 22.3% trimer product and 3.4% heavier product at 483 K for a reaction time of 3 h. The best fit kinetic model for the dimerization reaction was formulated from an assumption of no vacant reaction sites. For the trimerization reaction, a molecule of dimer (C20) formed on the active site, interacted with a molecule of 1-decene in the bulk solution to form a molecule of trimer (C30). Apparent activation energies for the dimerization and trimerization reactions were 70.8 ± 0.8 and 83.6 ± 0.9 kJ/mol, respectively. The C13-NMR spectrum indicated that the oligomer product contained a significant portion of highly branched hydrocarbons, causing a substantial reduction in the viscosity index compared to conventional poly-alpha olefin lubricant (PAO).

The polymerization of 1-decene catalyzed by rac-Me2Si(1-indenyl)2ZrCl2/AliBu3/[C6H5NH(CH3)2][B(C6F5)4] system with hydrogen has been carried out in the paper. The influence of reaction conditions o...

We report ignition delay time measurements carried out in both constant-volume spray and homogeneous gas-phase shock-tube environments at high pressures (1–4 MPa) for 1-decene, trans-5-decene, and n-decane. These measurements provide quantitative kinetic targets for the development of reaction mechanisms and assessment of the relative reactivity of these compounds under low-temperature, negative-temperature-coefficient (NTC), and high-temperature conditions. Derived cetane number (DCN) measurements carried out in spray ignition experiments are shown to be well-correlated with shock-tube ignition delay measurements in the NTC region, both of which show substantially reduced oxidative reactivity for the compounds containing double bonds (n-decane versus n-decenes) and lower reactivity for centrally located double bonds (trans-5-decene) compared to a double bond at the end of the carbon chain (1-decene). Ignition delays in both the shock tube and spray show differences of factors of 2–4 for NTC and low-tempe...

The construction of tricyclo[5.2.1.01,6]decene skeleton was achieved by cyclobutane ring formation via improved radical reaction using SmI2-H2O-HFIP and SmI2-LiCl conditions in good yields. Those additives were studied to increase the reactivity of SmI2. Two interesting reactions via neighboring group participations are described for introducing the C4 oxygen functionality by the assistance of C6 substituent in a regioselective manner.

The density and viscosity of a ternary 1-hexene(1) + 1-octene(2) +1-decene(3) mixture ( $$ w_{1} = w_{2} = w_{3} = 0.333 $$ weight fractions or $$ x_{1} = 0.4257 $$ , $$ x_{2} = 0.3190 $$ , $$ x_{3} = 0.2553 $$ mole fractions of 1-hexene, 1-octene, and 1-decene, respectively) have been simultaneously measured over the temperature range from (298 to 471) K and at pressures up to 196 MPa using a combined method of hydrostatic weighing and falling-body techniques, respectively. The combined expanded uncertainties of the density, pressure, temperature, concentration, and viscosity measurements at the 95% confidence level with a coverage factor of k = 2 are estimated to be (0.15 to 0.30)%, 0.05%, 0.02 K, 0.005 mol%, and (1.5 to 2.0)%, respectively. The measured densities and viscosities were used to calculate the excess molar volumes and viscosity differences. The excess molar properties ( $$ G_{\text{m}}^{\text{E}} , \, H_{\text{m}}^{\text{E}} , \, S_{\text{m}}^{\text{E}} $$ and $$ C_{\text{pm}}^{\text{E}} $$ ) and their pressure derivatives as a function of temperature and pressure have been calculated using the derived excess molar volumes. The measured viscosities were used to develop a theoretically based viscosity correlation model (Arrhenius–Andrade type equation) for the mixture.

The three-factor Box-Behnken design and the response surface methodology (RSM) were used to optimize the production of C20 (transportation fuel) and C30 + (lubricant oil) hydrocarbons obtained from 15 different oligomerization reactions of 1-decene over sulfated alumina catalysts in batch operation mode. The physiochemical properties of the sulfated alumina catalysts were characterized by N2 sorption, XRD and NH3-TPD. The formulated quadratic models as a function of three independent variables of reaction temperature (448–473 K), sulfuric acid concentration (2.5–4.5 M) and catalyst amount (5–15 wt%) were verified by the experimental results (1-decene conversion and product composition) with a coefficient of determination higher than 0.97 for all dependent variables (conversion, amount of C20 and C30 +). The optimal amount of C20 (65.4 wt%) was achieved at 473 K, using 3.5 M sulfated alumina and 8.8 wt% of catalyst. Similarly, the optimization of C30 + (47.7 wt%) was revealed at 473 K, using 3.5 M sulfated alumina and 15 wt% of catalyst. It was concluded that oligomerization over sulfated alumina was successfully optimized using Box-Behnken design.

Herein we report about an efficient isomerization/hydroformylation tandem reaction to convert a technical mixture of decene isomers selectively into the linear undecanal in a thermomorphic solvent system. By applying a rhodium/BIPHEPHOS catalyst a high turnover frequency of 375 h−1 and high regioselectivity of 92% for the linear product are achieved. Yields up to 70% of the linear aldehyde are obtained. The catalyst can be successfully separated from the product using a thermomorphic solvent system consisting of dimethyl formamide (catalyst phase) and dodecane (product phase). The leaching of the rhodium (0.6% of the initial amount) and phosphorus (1.2% of the initial amount) is very low. The catalyst was successfully recycled five times.

The article was dedicated to the copolymerization reaction of decylmethacrylate with decene-1. The copolymerizaion was realized with the participation of the inisiator the radical mechanism—izooil acid dinitrilyne. The learning of the polymerizaion reaction of decylmethacrylate with decene-1 shows that, it is possible to analyse the polymer connections having any molecular mass and content with the way of changing the monomers correlation and reaction temperature, that, it is possible to manage it knowing the regularities of the process. The effect of decylmethacrylate decene-1 copolymers to the viscosity-temperature properties has been learnt. As the result it has been showed that, using the joint polymers of decylmethacrylate—decene-1 in the content of the limpid oils as the thickener additive, it is possible to get the base oils with good viscosity-temperature properties.

Cyclic carbonates are valuable chemicals for the chemical industry and thus, their efficient synthesis is essential. Commonly, cyclic carbonates are synthesised in a two-step process involving the epoxidation of an alkene and a subsequent carboxylation to the cyclic carbonate. To couple both steps into a direct oxidative carboxylation reaction would be desired from an economical view point since additional work-up procedures can be avoided. Furthermore, the efficient sequestration of CO2, a major greenhouse gas, would also be highly desirable. In this work, the oxidative carboxylation of 1-decene is investigated using supported gold catalysts for the epoxidation step and tetrabutylammonium bromide in combination with zinc bromide for the cycloaddition of carbon dioxide in the second step. The compatibility of the catalysts for both steps is explored and a detailed study of catalyst deactivation using X-ray photoelectron spectroscopy and scanning electron microscopy is reported. Promising selectivity of the 1,2-decylene carbonate is observed using a one-pot two-step approach. Electronic supplementary material The online version of this article (10.1007/s11244-018-0900-y) contains supplementary material, which is available to authorized users.

Emeriones A–C (1–3), three highly methylated polyketides with bicyclo[4.2.0]octene and 3,6-dioxabicyclo[3.1.0]hexane functionalities, were isolated from Emericella nidulans. An additional peroxide bridge in compound 3 led to the construction of an unexpected 7,8-dioxatricyclo[4.2.2.02,5]decene scaffold. The structures of 1–3 were elucidated by comprehensive spectroscopic techniques, and their absolute configurations were confirmed by single-crystal X-ray crystallographic analyses and ECD calculations. Compound 1 shows weak inhibitory effects on NO production in LPS-induced RAW264.7 cells.

A variety of supported bimetallic catalysts were prepared through immobilization of AlCl 3 and TiCl 4 on different porous materials and used for the oligomerization of 1-decene in a fixed-bed reactor. The supported catalysts were characterized by various techniques including X-ray photoelectron spectroscopy (XPS), 27 Al MAS NMR, N 2 adsorption, adsorbed pyridine infrared (Py-IR), thermogravimetry and differential scanning calorimetry (TG–DSC), energy-dispersive spectrometry (EDS), and content measurement of active species. Their catalytic activity was examined and the underlying deactivation mechanism was explored. The initial catalytic activity was observed to be a linear function of the chlorine content of the supported catalyst. A catalyst using a coal-derived activated carbon support has the highest loading and exhibits the highest yield of polyalphaolefin (PAO), while a γ-Al 2 O 3 -supported catalyst gives higher stability. In addition, thermal treatment of the γ-Al 2 O 3 -supported catalyst results in reduced initial activity but enhanced stability. Both the loss of active species and the blockage and coverage of the pore structure by oligomers account for the deactivation of the supported catalyst.

The mechanism of selective co-oligomerization of ethylene and 1-hexene by the catalyst [CrCl3(PNPOMe)] (a, PNPOMe = N,N-bis(bis(o-methoxyphenyl)phosphine)methylamine) has been explored in detail using the density functional theory (DFT) method. The full catalytic cycles for the formation of 1-hexene and 1-decenes were calculated on the basis of the metallacyclic mechanism, and the distribution of all decene isomers was explained by locating Gibbs free energy surfaces of various pathways, which is in good agreement with the experimental results. A spin surface crossing through a minimum energy crossing point (MECP) from a sextet to a quartet surface takes place before the formation of metallacyclopentane, which opens up a much lower energy pathway and thus facilitates the following co-oligomerization reactions. It is worth noting that β-hydrogen agostic-assisted hydrogen transfer is of crucial importance for the decomposition of the metallacycle intermediates to give 1-hexene or decenes. Moreover, an analy...

A series of distillable alkyl carbamate ionic liquids (ALKCARB ILs) have been prepared from CO 2 and an amine, and then treated with silver (I) oxide to give the task specific ionic liquids. The synthesized ionic liquids have been used for the separation of 1-decene selectively from the mixture of n-decane/1-decene at room temperature. Presence of CO 2 to form carbamate with alkyl amine in the synthesis of ionic liquids remarkably enhanced the separation of olefin from mixture; however in its absence silver containing amine solvent provided very poor separation under identical conditions.