(-)-Menthol, (-)-borneol, S-(+)-3-octanol, S-(-)-2-methylbutanol-1, the 2nd generation Grubbs catalysts, dicyclopentadiene, 1,2,4-trichlorbenzene, maleic anhydride, Et3N, SOCl2, and cis-5-norbornene-endo-2,3-dicarboxylic anhydride (endo-NDA) were purchased from commercial suppliers (Sigma-Aldrich, ABCR GmbH, and TCI) and used as received unless otherwise noted. Methylene chloride and 1,2-dichloroethane were distilled over CaH2 under argon atmosphere and stored over molecular sieves (4 Å). Toluene was distilled in argon atmosphere and stored over molecular sieves (4 Å). ((1R,2S,5R)-6,6-Dimethylbicyclo[3.1.1]heptan-2-yl)methanol (pinanol) was prepared according to the procedure described earlier [36 (link)].
Dicyclopentadiene
Manufactured by Merck Group
Sourced in United States
Dicyclopentadiene is a chemical compound used as a raw material in the production of various industrial and agricultural products. It is a colorless liquid with a distinctive odor. Dicyclopentadiene is primarily used as a monomer in the synthesis of other compounds, serving as a building block for the creation of more complex materials and substances.
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Lab products found in correlation
Pluronic p123, by Merck Group (2 mentions)
3 bromopyridine, by Merck Group (2 mentions)
Phenylcyclohexane, by Merck Group (2 mentions)
5 ethylidene 2 norbornene, by Merck Group (2 mentions)
Grubbs second generation catalyst, by Merck Group (2 mentions)
Hydrochloric acid (hcl), by Merck Group (2 mentions)
Sodium hydroxide (naoh), by Merck Group (2 mentions)
Urea, by Merck Group (2 mentions)
Maleic anhydride, by Merck Group (1 mentions)
Borneol, by Merck Group (1 mentions)
Methyl acrylate, by Merck Group (1 mentions)
Butylated hydroxytoluene, by Merck Group (1 mentions)
Hexane, by Merck Group (1 mentions)
Diisopropyl azodicarboxylate, by Merck Group (1 mentions)
Maleimide, by Merck Group (1 mentions)
Dichloromethane, by Thermo Fisher Scientific (1 mentions)
Triphenylphosphine, by Merck Group (1 mentions)
Thionyl chloride, by Merck Group (1 mentions)
Furan, by Merck Group (1 mentions)
N phenylmaleimide, by Merck Group (1 mentions)
15 protocols using dicyclopentadiene
1
Synthesis of Bicyclic Compounds
2
Purification of Organic Reagents
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Dicyclopentadiene, methyl acrylate (99%), pent-1-en-3-on (ethyl-vinyl ketone) (97%), were provided from Aldrich. methyl acrylate prior to use was sequentially washed with aqueous NaOH and distilled water. Then it was dried with CaCl2 and fractionally distilled under reduced pressure. It was stored under nitrogen at 0 °C in dark. Ethyl-vinyl ketone was dried with MgSO4 and distilled.
3
Hybrid Dendrimer-Based Catalysts Synthesis
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The following substances were used as substrates and reference compounds: phenylacetylene C6H5CH≡CH (Aldrich, 98 %); styrene C6H5CH=CH2 (Aldrich,≥99 %); ethylbenzene C6H5CH2CH3 (Reachim, Purum); p‐methylstyrene p‐CH3C6H4CH=CH2 (Aldrich, 96 %); p‐tert‐butylstyrene p‐(CH3)3CC6H4CH=CH2 (Aldrich, 94 %); 2,5‐dimethyl‐2,4‐hexadiene (CH3)2C=CH–CH=C(CH3)2 (Aldrich, 98 %); isoprene H2C=C(CH3)−CH=CH2 (Aldrich, 99 %); 1,3‐cyclohexadiene (Aldrich, 97 %); dicyclopentadiene C10H12 (Aldrich, 97 %).
Ethanol C2H5OH (IREA 2000, Analytical Grade), methanol (Acros Organics, 99.9 %), chloroform CHCl3 (Chimmed, Reagent Grade) and n‐hexane n‐C6H14 (Chimmed, Reagent Grade) were used as solvents.
For the synthesis of hybrid dendrimer‐based catalysts the following substances were used: Pd acetate (II) Pd(OAc)2 (Aldrich, 99.9 %); poly(propylene imine) (PPI) dendrimers of the 2nd generation with a diaminobutane core DAB(NH2)8, earlier prepared according to literature procedure;77 (3‐glycidoxypropyl)trimethoxysilane (Acros Organics,≥97 %); poly(ethylene glycol)‐block‐poly(propylene glycol)‐block‐poly(ethylene glycol) with the average number molecular weight Mn of 5800 HO(CH2CH2O)20(CH2CH(CH3)O)70(CH2CH2O)20H (Pluronic P123, Aldrich); microporous G3‐dendr‐SiO2 and mesoporous G2‐dendr‐meso‐SiO2 carriers, synthesized earlier according to the published procedure.46
Ethanol C2H5OH (IREA 2000, Analytical Grade), methanol (Acros Organics, 99.9 %), chloroform CHCl3 (Chimmed, Reagent Grade) and n‐hexane n‐C6H14 (Chimmed, Reagent Grade) were used as solvents.
For the synthesis of hybrid dendrimer‐based catalysts the following substances were used: Pd acetate (II) Pd(OAc)2 (Aldrich, 99.9 %); poly(propylene imine) (PPI) dendrimers of the 2nd generation with a diaminobutane core DAB(NH2)8, earlier prepared according to literature procedure;
4
Fabrication of Au-coated Si/SiO2 Wafers
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Gold shot (99.99%) (J&J Materials) and
silicon (100) wafers (University Wafers) were used in the preparation
of Au-coated Si/SiO2 wafers. trans-3,6-Endomethylene-1,2,3,6-tetrahydrophtaloyl
chloride (NBDAC) was purchased from Sigma-Aldrich and Santa Cruz Biotechnology.
5-Perfluoro-n-alkyl-norbornenes (NBFn; n = 4, 6, and 8 perfluorinated carbons) with a 3:1 endo:exo isomer
ratio were synthesized as previously reported.26 (link),27 (link) Norbornene (NB) and dicyclopentadiene (DCPD) were purchased from
Sigma-Aldrich and used as received. DCM, THF, n-pentane,
acetone, ethyl vinyl ether, and ethanol were purchased from ThermoFisher
and used as received. Porous supports of poly(acrylonitrile) (PAN)
and poly(ether sulfone) (PES) were purchased from Sterlitech, Inc.
with molecular weight cutoffs (MWCO) of 30 and 100 (PAN) and 50 kDa
(PES). Prior to use, PAN coupons were cut to a size of 4 or 36 cm2 and stored in D.I. water for ∼24 h to remove glycerol,
an additive to prevent pore collapse during shipment. After 24 h,
coupons were rinsed with D.I. water and stored in fresh D.I. water
at room temperature until used. Before use, the films were dried in
a stream of nitrogen to remove absorbed water.
silicon (100) wafers (University Wafers) were used in the preparation
of Au-coated Si/SiO2 wafers. trans-3,6-Endomethylene-1,2,3,6-tetrahydrophtaloyl
chloride (NBDAC) was purchased from Sigma-Aldrich and Santa Cruz Biotechnology.
5-Perfluoro-n-alkyl-norbornenes (NBFn; n = 4, 6, and 8 perfluorinated carbons) with a 3:1 endo:exo isomer
ratio were synthesized as previously reported.26 (link),27 (link) Norbornene (NB) and dicyclopentadiene (DCPD) were purchased from
Sigma-Aldrich and used as received. DCM, THF, n-pentane,
acetone, ethyl vinyl ether, and ethanol were purchased from ThermoFisher
and used as received. Porous supports of poly(acrylonitrile) (PAN)
and poly(ether sulfone) (PES) were purchased from Sterlitech, Inc.
with molecular weight cutoffs (MWCO) of 30 and 100 (PAN) and 50 kDa
(PES). Prior to use, PAN coupons were cut to a size of 4 or 36 cm2 and stored in D.I. water for ∼24 h to remove glycerol,
an additive to prevent pore collapse during shipment. After 24 h,
coupons were rinsed with D.I. water and stored in fresh D.I. water
at room temperature until used. Before use, the films were dried in
a stream of nitrogen to remove absorbed water.
5
Dicyclopentadiene-based Biobased Polymer Synthesis
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Dicyclopentadiene (Sigma-Aldrich),
butylated hydroxy toluene (BHT), boron trifluoride diethyl etherate
catalyst (BFE), and hexane were purchased from Sigma-Aldrich. Linseed
oil and soybean oil of supreme grade were obtained from Cargill. HOSO
was supplied by the Ohio Soybean Council (OSC). Chemical structures
of the reacting constituents are provided inFigure 1 .
butylated hydroxy toluene (BHT), boron trifluoride diethyl etherate
catalyst (BFE), and hexane were purchased from Sigma-Aldrich. Linseed
oil and soybean oil of supreme grade were obtained from Cargill. HOSO
was supplied by the Ohio Soybean Council (OSC). Chemical structures
of the reacting constituents are provided in
6
Synthesis of Functionalized Norbornene Derivatives
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Example 1
Materials: The following materials were purchased and used as received.
Dimethyl 5-norbornene-2,3-dicarboxylate (C3) was purchased from Alfa Aesar,
Dichloromethane (DCM) was stored over activated Alumina and purged with Argon before use, Isopropyl alcohol (IPA), dicyclopentadiene (DCPD), 1H,1H,2H-Perflouro-1-octene (PF6), 1H,1H,2H-Perflouro-1-dodecene (PF10), toluene, thionyl chloride, ethylacetate, dimethylformamide (DMF), Maleimide, furan, diisopropylazodicarboxylate (DIAD), triphenylphosphine (Ph3P), 1-haxadecanol, tetrahydrofuran (THF), ethyl acetate, N-phenylMaleimide, acetonitrile, methanol, Grubbs second generation catalyst, 3-bromopyridine, and pentane were obtained from Sigma-Aldrich Co. and used without further treatment. Dichloropentane, also obtained from Sigma-Aldrich Co., was treated with basic alumina before use. Cyclooctadiene (COD) was purified by vacuum distillation from boron trifluoride and used fresh.
7
Synthesis of Phosphorus-Containing Olefin Polymer
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Example 3
To a glass reaction bottle, 20 g toluene, 60 g DOPO-HQ terminal vinylated compound (i.e. vinylbenzyl-etherified-DOPO, synthesized by Elite Material Co., Ltd. and disclosed in U.S. Patent Application No.: U.S. Ser. No. 14/520,779, U.S. Patent Publication No.: 2015-0166788), 40 g Dicyclopentadiene monomer (Dicyclopentadiene available from Sigma-Aldrich) and 0.01 g Grubbs catalyst II (Grubbs Catalyst 2nd Generation available from Sigma-Aldrich) were added to obtain a solution. The solution was heated to 80° C. and stirred for 12 hours. Then, the solution was cooled to room temperature to obtain a light brown liquid solution, i.e., phosphorus-containing olefin polymer product C of the present invention (product C).
8
Synthesis of Epoxy-based Nanocomposites
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Ethylene maleic anhydride (EMA) copolymer, dicyclopentadiene, and Grubb's 2nd-generation were procured from Sigma-Aldrich, USA. Epoxy resin was purchased from Huntsman India Ltd. Ammonium chloride, urea, resorcinol, sodium hydroxide, hydrochloric acid, 37 wt% formaldehyde solution and 1-octanol were obtained from Merck India Pvt Ltd. Multi-walled CNT with an aspect ratio of 2000 : 1 was purchased from Nanoshel – Mumbai, India.
9
Facile Synthesis of Polymer Composites
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Dicyclopentadiene (DCPD), 5-ethylidene-2-norbonene (ENB), second-generation Grubbs’ catalyst (GC2), phenylcyclohexane (PCH), allyl chloride, urea, sodium hydroxide (NaOH), hydrochloric acid (HCl), and decylamine were purchased from Sigma-Aldrich and used as received. Tannic acid was obtained from Alfa Aesar and used without modification. Tributyl phosphite inhibitor (TBP) was purchased from TCI-Sejin CI. Acetone (99.5%) was purchased from Dae Jung Chemical and used without further purification. Cellulose nanocrystal (CNC) was acquired from Nanografi Nano Technology and used as received. A 26V-65W FX-8801 HAKO soldering iron was used to trigger FP. ISTEK Multimeter CP-500L was used to adjust pH levels. 15 × 150 mm glass test tubes (Tube 2, 15150) were purchased from Dai Han Scientific. 1.5 × 80 mm Borokapillaren capillary tubes were purchased from Muller GmbH. T-type welded thermocouples were purchased from Omega Engineering. TM947SD digital thermometer from Lutron Instruments was used to record temperature values during the FP reaction.
10
Rhodium-Catalyzed Olefin Hydroformylation
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Ligand TPPTS (sodium salt of sulfonated triphenylphosphine, Fig. 1 ) and rhodium precursor HRh(CO)(TPPTS)3 were prepared according to the literatures.29,30 (link) All the solvents were purchased from Kelong Chemical Co. of Chengdu and used without any additional purification. 1-Hexene, 1-octene, 1-decene, 1-dodecene, cyclohexene, norbornene and dicyclopentadiene were purchased from Sigma-Aldrich. Hydrogen (H2, 99.99%) and carbon monoxide (CO, 99.9%) were obtained from Southwest Institute. The composition of reaction mixture was determined by means of gas chromatography (PANNA A91, KB-1: 30 m × 0.25 mm × 0.50 μm, FID). Rhodium leaching in the product mixture was analyzed by inductively coupled plasma atomic emission spectroscopy (ICP-AES). 31P NMR spectra were recorded on the Bruker AVANCE III HD 400 M.
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