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Alkenes

Alkenes, also known as olefins, are unsaturated hydrocarbon compounds containing at least one carbon-carbon double bond.
These versatile organic molecules are widely used in a variety of chemical processes, including polymerization, hydrogenation, and oxidation reactions.
Alkenes display unique reactivity and physical properties that make them valuable intermediates in the synthesis of a wide range of pharmaceuticals, fuels, and other important chemicals.
Researchers optimizing alkene-based protocols can leverage PubCompare.ai's AI-powered tools to easily locate the best experimental protocols from literature, preprints, and patents, facilitating improved reproducability and efficincy in their alkene research.

Most cited protocols related to «Alkenes»

The Methods section is divided into three subsections. In the first, lipid molecule and atom names are briefly reviewed to avoid confusion among several commonly used conventions. Section 2.2 describes the QM methods used in justifying modifications to the partial charges for certain atoms in the head group of the lipid molecules along with the optimization procedure used to produce optimized non-bond parameters for the ester moieties in the glycerol linker region. This subsection also describes the QM methods used to obtain highly accurate torsional profiles for certain head group and alkene dihedrals. The Section 2.3 describes the methods used in the molecular dynamics (MD) simulations. The C36 additive all-atom lipid force field may be downloaded from the MacKerell group web page at http://mackerell.umaryland.edu/CHARMM_ff_params.html.
Publication 2010
Alkenes Conferences Esters Glycerin Head Lipids
Gantrez® S-97 (Mw = 1.2 × 106), a copolymer obtained from the free acid of methyl vinyl ether and maleic anhydride polymers, was provided by Ashland (Tadworth, Surrey, UK). Poly(ethyleneglycol) (PEG) 10,000 Da was obtained from Sigma–Aldrich (Poole, Dorset, UK). Parafilm M®, a flexible thermoplastic sheet (127 μm thickness) made of olefin-type material, was used as skin simulant for insertion studies, was obtained from BRAND GMBH (Wertheim, Germany). Deka® poly(urethane) needle testing foil was provided by Melab GmbH (Leonberg, Germany).
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Publication 2014
Acids Alkenes Gantrez Glycol, Ethylene Maleic Anhydride Needles Poly A Polymers Skin Urethane vinyl ether
Force field-specific MATCH libraries were constructed via MATCH based on the CHARMM36 topology files: top_all22_prot, top_all27_na, top_all35_carb, top_all35_ethers, top_all36_cgenff and top_all36_lipid. For each force field the molecular fragments for each atom type were constructed through an iterative optimization procedure. Using a given force field the goal is to correctly assign types for all the atoms within the force field. The main concern in this process is to avoid mistyping by incorrectly making one type cover the space of another. To avoid this, atom types were grouped together by the atom element and bond number and were developed simultaneously. That is, each time there was a modification of a fragment, each atom that was of the group’s element and number of bonds was typed and if there were fewer mistypings this change was accepted. This was repeated until there were no mistypings. Most aliphatic atom types have rather distinct chemical space and, thus, required a few rounds of optimization. On the other hand, it was more difficult to create the optimal set of fragments for atom types that are exclusively based in rings and, thus, these atom types required multiple rounds of optimization. The Perl script TestBuildTypeStrings.t that is required for this optimization is provided in the MATCH package distribution for future optimizations and development of atom-type fragments for new force fields. Another challenge in this optimization scheme is keeping the atom-type fragments as general as possible while preserving their unique chemical environment.
For each force field that contained residue patches, each patch was applied if it increased the chemical space of the set (i.e., added new atom types or bond increment rules) or was necessary to correct polymer connectivity. By default, the NTER and CTER patches were applied to the protein force field residues and the 5TER and 3TER patches were applied to the nucleic acid force field residues. With the exception of CGENFF, all molecules in the topology files were included in the process of constructing the force field-specific MATCH libraries. In total, 53 of the 415 molecules in the CGENFF topology file were eventually excluded. There were 3 primary categories of molecules that were excluded: molecules containing a fused ring that would require all bond increments to be refined as a result of charge smearing; molecules containing a conjugated alkene chain which has alternating CG2DC1 and CG2DC2 atom type designations but the same chemical environment; and molecules that have a connectivity of two atom types A and B such that A – B – A – B – A, which would require simultaneous refinement of the A–B bond increment. The latter two categories of molecules have been incorporated into the most recent version of the CGENFF MATCH libraries, but were not used in this study.
Bond increments were extracted from each force field topology file in an automated fashion as discussed in the previous section, and can be reproduced in MATCH using GenerateBondIncrementRules.pl. Refinement bond increments were added to fix obvious exceptions to the BCIs, e.g., where the default BCIs could not reproduce the charge distributions in the molecules, and were usually small in number, with exception of CGENFF. In addition to the compounds that were excluded when constructing the CGENFF-specific MATCH libraries, several other compounds in the CGENFF topology file do not obey clear bond increment rules. With additional refinement rules, however, it was possible to reliably reproduce charges for these compounds.
Publication 2011
2-benzylidene-3-(cyclohexylamino)-2,3-dihydro-1H-inden-1-one Alkenes Ethers Lipids Nucleic Acids Polymers Proteins

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Publication 2010
Alkenes Aves Biotin Fluorescein-5-isothiocyanate High-Performance Liquid Chromatographies Peptide Biosynthesis
All peptides were synthesized on solid Rink-amide resin using fluorenylmethoxycarbonyl (Fmoc) chemistry on a model 433A peptide synthesizer (Applied Biosystems) or a Tribute peptide synthesizer (Protein Technologies). Lysines were added to the terminal positions of the peptide sequences to encourage aqueous solubility. The peptide CRGDSGK was synthesized as the others, but with the orthogonal protecting group 1-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethyl (Dde) on the C-terminal lysine. On resin, the N-terminus was capped with acetic anhydride and Dde was selectively removed with 2% hydrazine allowing labeling with 5(6)-carboxy rhodamine (Anaspec) by HATU coupling or with AlexaFluor 488 terafluorophenyl ester (AlexaFluor 488 5-TFP Invitrogen). Peptides were analyzed by reverse-phase high-performance liquid chromatography (HPLC) and matrix-assisted laser desorption ionisation (MALDI) mass spectrometry and purified by reverse-phase HPLC.
HRMAS 1H-NMR: HRMAS 1H-NMR spectroscopy was performed on a Varian Inova at 400mHz with a 4-mm GHX-Nano probe. Monomer solutions of 10 wt% in phosphate-buffered D2O and 0.05 wt% I2959 inside 40mL capacity nanotubes were exposed to 365-nm light at 10mW cm−2 and periodic NMR measurements were taken. It should be noted that the curvature of the nanotubes, in which polymerization occurs and spectra are taken, interferes with the light exposure, making this a poor technique to measure kinetics. It is, however, an appropriate means to determine the conversion of alkenes relative to the generation of thioethers, confirming the reaction mechanism.
Publication 2009
1H NMR acetic anhydride Alkenes Esters High-Performance Liquid Chromatographies hydrazine Kinetics Light Lysine Peptides Phosphates Polymerization Proteins Resins, Plant Rhodamine Rink amide resin Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization Spectroscopy, Nuclear Magnetic Resonance Thioethers

Most recents protocols related to «Alkenes»

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Example 8

Cyclohexene (1a) and polar organic solvent (as mentioned in Table 1) in (1:2 to 1:10 weight ratio with respect to the substrate) was taken in to a 60 ml vessel. Further, the hybrid photocatalyst was added and the resulting mixture was saturated with CO2 by purging at 1 atm pressure. The reaction vessel was sealed and irradiated with 20 W LED light (Model No. HP-FL-20 W-F, Hope LED Opto-Electric CO., Ltd) for 24 h. The conversion of the olefin and selectivity of the α,β-unsaturated hydroxyl or carbonyl compound as determined by GC-FID and GC-MS is mentioned in the Table 1 (entry 8-13).

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Patent 2024
Alkenes Blood Vessel cyclohexene Electricity Gas Chromatography-Mass Spectrometry Genetic Selection Hybrids Hydroxyl Radical Light Pressure Solvents
Not available on PMC !

Example 3

Cyclohexene (1a) and polar organic solvent, preferably acetonitrile in (1:2 to 1:10 weight ratio with respect to the substrate) was taken in to a 60 ml vessel. Further, the bare graphene oxide as photocatalyst (1 to 10 mol % of the substrate) was added and the resulting mixture was saturated with CO2 by purging at 1 atm pressure. The reaction vessel was sealed and irradiated with 20 W LED light (Model No. HP-FL-20 W-F, Hope LED Opto-Electric CO., Ltd) for 24 h. The intensity of the LED light at the reaction flask was measured to be 86 W/m2 by intensity meter. The conversion of the olefin was examined by GC-FID based on the unreacted substrate. The selectivity of the α,β-unsaturated hydroxyl or carbonyl compounds was determined by GC-MS. The conversion of olefin and the selectivity towards the corresponding α,β-unsaturated hydroxyl and ketone is given in the Table 1, entry 3.

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Patent 2024
acetonitrile Alkenes Blood Vessel cyclohexene cyclohexene oxide Electricity Gas Chromatography-Mass Spectrometry Genetic Selection Graphene graphene oxide Hydroxyl Radical Ketones Light Pressure Solvents
Not available on PMC !

Example 109

[Figure (not displayed)]

The alkene (2.91 mmol) was dissolved in MeOH (0.1 M) and Pd(OH)2/C (0.146 mmol) was added. A Parr Hydrogenator was used at 40 psi. The palladium catalyst was carefully filtered off through celite and rinsed with EtOAc. The crude material was used in the next step and provided quantitative yield.

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Patent 2024
Alkenes Celite Nucleosides Nucleotides Palladium Pharmaceutical Preparations Virus Diseases
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Example 1

An Arab light crude oil with an API gravity of 33.0 and a sulfur content of 1.6 wt. % was fractionated in a distillation column to form a light stream and a heavy stream. Properties of the feed crude oil stream and the resulting fractions (based on their percent composition in the crude oil fractions) are given in Table 1 below.

TABLE 1
Stream NameBoiling RangeNi (ppm)V (ppm)S (wt. %)N (ppm)
Hydrocarbon3.414.521.6444
Feed
Light StreamLess than<1<10.213
370° C.
Heavy StreamGreater than 4.414.21.4431
370° C.

Details of the un-hydrotreated heavy stream are shown below in Table 2, where the heavy stream is designated EX-1(A).

The same Arab light crude oil used in Example 1 was directly cracked in the same cracking reactor and under the same conditions as was used in Example 3(A), results are designated CE-1. Specifically, the temperature was 675° and the TOS was 75 seconds.

TABLE 4
3(A)3(B)3 (Combined)CE-1
(wt. %)(wt. %)(wt. %)(wt. %)
Dry Gas9.876.438.0610.80
Light Olefins39.1151.6743.4634.89
Ethylene11.8210.0610.6910.41
Propylene18.3425.7621.0516.51
Butylene8.9615.8411.727.96
Gasoline Range33.1224.6028.3824.21
Products
Coke4.926.615.5113.86
Conversion91.1494.4689.8687.38

As can be seen in Table 4, the combined yields of total light olefins from the present methods are significantly higher than the yields from the comparative methods. Further, each of examples 3(A), 3(B), and 3(Combined) show significantly decreased levels of coke formation relative to the comparative example CE-1.

Example 2

The heavy stream from Example 1 was hydrotreated in a three-stage hydrotreater. The reaction conditions were: a weighted average bed temperature of 400° C., a pressure of 150 bar, a liquid hourly space velocity (LHSV) of 0.5 h−1, an Hz/oil ratio 1200:1(v/v), an oil flowrate of 300 ml/h, and an H2 flowrate of 360 L/h.

The first stage of the hydrotreater used a KFR-22 catalyst from Albemarle Co. to accomplish hydro-demetallization (HDM). The second stage of the hydrotreater used a KFR-33 catalyst from Albemarle Co. to accomplish hydro-desulfurization (HDS). The third stage of the hydrotreater used a KFR-70 catalyst from Albemarle Co. to accomplish hydro-dearomatization (HDA). The first, second, and third stages were discrete beds placed atop one another in a single reaction zone. The heavy stream flowed downward to the first stage, then to the second stage, and then to the third stage. Properties of this hydrotreated heavy stream are shown in Table 2 below and are designated EX-2.

TABLE 2
EX-1(A)EX-2
Kinematic viscosity at 100° C. (mm2/s)6
Density (g/ml)0.9650.8402
Nitrogen (ppm)120868.5
Sulfur (wt. %)3.10.007
Ni (ppm)10<1
V (ppm)32<1
Aromatics68.625.6

The hydrotreated heavy stream from Example 2 was fed to the advanced cracking evaluation unit. A TOS of 75 seconds, a residence time of from 1 to 2 seconds, and a temperature of 645° C. was used. Characterization of the product is given in Table 5 below.

TABLE 5
CE-13(B)
Temp. ° C.645645
T.O.S.(s)7575
Steaming Cond.810° C. for 6 hours
CAT/OIL6.488.00
Conversion (%)82.7794.46
Yields (wt. %)
H2 (wt. %)0.600.93
C1 (wt. %)4.823.71
C2 (wt. %)2.741.79
C2═ (wt. %)8.0710.06
C3 (wt. %)2.262.25
C3═ (wt. %)17.1625.76
iC4 (wt. %)0.671.58
nC4 (wt. %)0.550.69
t2C4═ (wt. %)2.393.92
1C4═ (wt. %)1.672.78
iC4═ (wt. %)3.596.01
c2C4═ (wt.%)1.903.14
1,3-BD (wt. %)0.010.63
Total Gas (wt. %)46.4463.25
Gasoline (wt. %)18.0924.60
LCO (wt. %)9.843.95
HCO (wt. %)7.381.59
Coke (wt. %)18.246.61
Groups (wt. %)
H2—C2 (dry gas)16.2416.49
C3—C4 (LPG)30.1946.77
C2═−C4═ (Light34.7952.30
olefins)
C3═+C426.7142.24
C4═ (Butenes)9.5516.48
Molar Ratios
mol/mol)
C2═/C23.156.03
C3═/C37.9711.97
C4═/C48.067.52
iC4═/C40.380.36
iC4═/iC45.513.94

As can be seen in Table 5, utilizing a hydrotreated heavy stream as the feed to the catalytic reactor results in higher conversion; greater yield of C2, C3, and C4 olefins; greater yield of gasoline; and significantly decreased coke formation, among other advantages.

Example 3

The respective fractions of Arab light crude were cracked at the conditions described below. A catalyst with the composition shown in Table 3 below as used in all of the reactions.

TABLE 3
ComponentWeight %Notes
ZSM-520Phosphorus impregnated at 7.5 wt. %
P2O5 on zeolite
USY21Lanthanum impregnated at 2.5 wt. %
La2O3 on zeolite
Alumina8Pural SB from Sasol
Clay49Kaolin
Silica2Added as colloidal silica Ludox TM-40

An Advanced Cracking Evaluation (ACE) unit was used to simulate a commercial FCC process. The reaction was run two times with fresh catalyst to simulate two separate FCC reaction zones in parallel.

Prior to each experiment, the catalyst is loaded into the reactor and heated to the desired reaction temperature. N2 gas is fed through the feed injector from the bottom to keep catalyst particles fluidized. Once the catalyst bed temperature reaches within ±2° C. of the reaction temperature, the reaction can begin. Feed is then injected for a predetermined time (time-on-stream (TOS)). The desired catalyst-to-feed ratio is obtained by controlling the feed pump. The gaseous product is routed to the liquid receiver, where C5+ hydrocarbons are condensed and the remaining gases are routed to the gas receiver. After catalyst stripping is over, the reactor is heated to 700° C., and nitrogen was replaced with air to regenerate the catalyst. During regeneration, the released gas is routed to a CO2 analyzer. Coke yield is calculated from the flue gas flow rate and CO2 concentration. The above process was repeated for each of Examples 3(A) and 3(B). The weight ratio of catalyst to hydrocarbons was 8.

It should be understood that time-on-stream (TOS) is directly proportional to residence time.

The light stream from Example 1 was fed to the advanced cracking evaluation unit. A time-on-stream (TOS) of 75 seconds, a residence time of from 1 to 2 seconds, and a temperature of 675° C. was used.

The hydrotreated heavy stream from Example 2 was fed to the advanced cracking evaluation unit. A TOS of 75 seconds, a residence time of from 1 to 2 seconds, and a temperature of 645° C. was used. Characterization is shown in both Table 4 and Table 5.

The streams of Examples 3(A) and 3(B) were combined to form a single stream. The single stream simulates the output of processing a whole crude according to the methods of the present disclosure.

Example 3(Combined) is a weighted average of Examples 3(A) and 3(B). Example 3(A) represented 53 wt. % of Example 3(Combined). Example 3(B) represented 44 wt. % of Example 3 (Combined).

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Patent 2024
Adjustment Disorders Alkenes Arabs butylene Catalysis Clay Cocaine Distillation ethylene GAS6 protein, human Gravity Hutterite cerebroosteonephrodysplasia syndrome Hydrocarbons Kaolin Lanthanum Light Molar Neoplasm Metastasis Nitrogen Oxide, Aluminum Petroleum phosphoric anhydride Phosphorus Pressure propylene Regeneration Silicon Dioxide Simulate composite resin Sulfur Viscosity Vision Zeolites

Example 1

An Arab light crude oil with an API gravity of 33.0 and a sulfur content of 1.6 wt. % was fractionated in a distillation column to form a light stream and a heavy stream. Properties of the feed crude oil stream and the resulting fractions (based on their wt. % composition in the crude oil) are given in Table 1 below.

TABLE 1
Boiling Ni VS N
Stream NameRange(ppm)(ppm)(wt. %)(ppm)
Hydrocarbon4.414.21.6444
Feed
Light StreamLess than <1<10.8136
540° C.
Heavy StreamGreater than4.414.20.8308
540° C.

The same Arab light crude oil used in Example 3 was directly cracked in the same cracking reactor and under the same conditions as was used in Example 3.

TABLE 4
EX-3CE-1
Constituent(wt. %)(wt. %)
H20.680.72
C16.476.86
C23.103.23
C2 = (ethylene)10.8510.41
C31.671.65
C3 = (propylene)18.2016.51
iC40.460.42
nC40.410.56
t2C4 =2.221.93
1C4 =1.651.40
iC4 =3.573.09
c2C4 =1.791.54
1,3-BD1.110.99
Butenes9.227.96
Total Gas52.1749.31
Dry Gas10.2410.80
Total Light Olefins38.2734.89
Gasoline27.9224.21
LCO8.439.43
HCO2.043.20
Coke9.4413.86
Total Gas + Coke61.6163.17

As can be seen in Table 4, the yield of total light olefins from the inventive EX-3 is significantly higher than the yield of light olefins in the comparative CE-1. Additionally, EX-3 shows significantly lower coke formation than the comparative CE-1.

Example 2

The heavy stream from Example 1 was hydrotreated in a three-stage hydrotreater. The reaction conditions were: a weighted average bed temperature of 400° C., a pressure of 150 bar, a liquid hourly space velocity (LHSV) of 0.5 h−1, an H2/oil ratio 1200:1 (v/v), an oil flowrate of 300 ml/h, and an H2 flowrate of 360 L/h.

The first stage of the hydrotreater used a KFR-22 catalyst from Albemarle Co. to accomplish hydro-demetallization (HDM). The second stage of the hydrotreater used a KFR-33 catalyst from Albemarle Co. to accomplish hydro-desulfurization (HDS). The third stage of the hydrotreater used a KFR-70 catalyst from Albemarle Co. to accomplish hydro-dearomatization (HDA). The first, second, and third stages were discrete beds placed atop one another in a single reaction zone. The heavy stream flowed downward to the first stage, then to the second stage, and then to the third stage. Properties of this hydrotreated heavy stream are shown in Table 2 below.

TABLE 2
Kinematic viscosity at 100° C.67.6 mm2/s
Density at 60° C.0.9 g/cm3
Sulfur (wt. %)0.36
Ni (ppm)1
V (ppm)3
Fe (ppm)<1
Na (ppm)<10

Example 3

A catalyst with the composition shown in Table 3 below as used in all of the reactions.

TABLE 3
ComponentWeight %Notes
ZSM-520Phosphorus impregnated at 7.5 wt. % P2O5
on zeolite
USY21Lanthanum impregnated at 2.5 wt. % La2O3
on zeolite
Alumina8Pural SB from Sasol
Clay49Kaolin
Silica2Added as colloidal silica Ludox TM-40

An Advanced Cracking Evaluation (ACE) unit was used to simulate a down-flow FCC reaction zone with multiple inlet points. The ACE unit emulates commercial FCC process.

Prior to each experiment, the catalyst is loaded into the reactor and heated to the desired reaction temperature. N2 gas is fed through the feed injector from the bottom to keep catalyst particles fluidized. Once the catalyst bed temperature reaches within ±2° C. of the reaction temperature, the reaction can begin. Feed is then injected for a predetermined time (time-on-stream (TOS)). The desired catalyst-to-feed ratio is obtained by controlling the feed pump. The gaseous product is routed to the liquid receiver, where C5+ hydrocarbons are condensed and the remaining gases are routed to the gas receiver. After catalyst stripping is over, the reactor is heated to 700° C., and nitrogen was replaced with air to regenerate the catalyst. During regeneration, the released gas is routed to a CO2 analyzer. Coke yield is calculated from the flue gas flow rate and CO2 concentration. The above process was repeated for each of Examples 3(A) and 3(B).

The light stream from Example 1 was combined with the hydrotreated heavy stream from Example 2 to form a combined feed stream. The combined feed stream was fed to the ACE unit. A time-on-stream (TOS) of 75 seconds and a temperature of 675° C. was used. Fresh catalyst was steamed deactivated at 810° C. for 6 hours to resemble the equilibrium catalyst in the actual process. The steam deactivated catalyst was used in this reaction. It should be understood that TOS is directly proportional to residence time.

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Patent 2024
43-63 Adjustment Disorders Alkenes Arabs BD-38 butylene Catalysis Clay Cocaine Distillation ethylene Gravity Hydrocarbons Kaolin Lanthanum Light Neoplasm Metastasis Nitrogen Oxide, Aluminum Petroleum phosphoric anhydride Phosphorus Pressure propylene Regeneration Silicon Dioxide Steam Sulfur Viscosity Vision Zeolites

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More about "Alkenes"

Alkenes, also known as olefins, are a class of unsaturated hydrocarbon compounds characterized by the presence of at least one carbon-carbon double bond.
These versatile organic molecules have a wide range of applications in various chemical processes, including polymerization, hydrogenation, and oxidation reactions.
Alkenes display unique reactivity and physical properties that make them valuable intermediates in the synthesis of a diverse array of pharmaceuticals, fuels, and other important chemicals.
Researchers working on alkene-based protocols can leverage the AI-powered tools offered by PubCompare.ai to easily locate and compare the best experimental procedures from literature, preprints, and patents.
This can help improve the reproducability and effeciency of their alkene research.
Some related terms and subtopics to consider include: di-tert-butyl peroxide (a radical initiator used in alkene polymerization), Solvesso 150 (a solvent mixture used in alkene-based formulations), Irganox® 1076 (an antioxidant used to stabilize alkene-containing products), 5-norbornene-2-carboxylic acid (a cyclic alkene used in polymer synthesis), Gantrez® S-97 (a copolymer of methyl vinyl ether and maleic anhydride), silica gel (a common desiccant used in alkene purification), HP-INNOWAX (a stationary phase used in gas chromatography of alkenes), DMSO (a solvent used in alkene reactions), and 5-vinyl-2-norbornene (a cyclic alkene monomer).