- Synthesis of 5-vinyl-2-norbornene through Diels–Alder reaction of cyclopentadiene with 1,3-butadiene in supercritical carbon dioxide
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An efficient method for the synthesis of 5-vinyl-2-norbornene from cyclopentadiene and 1,3-butadiene was developed. The Diels–Alder reaction of cyclopentadiene with 1,3-butadiene proceeded smoothly in supercritical carbon dioxide in the absence of any pol
- Meng, Fan-Qiang,Feng, Xiu-Juan,Wang, Wan-Hui,Bao, Ming
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- Method for Preparation of 5-Vinyl-2-Norbornene
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The present invention relates to a method for preparing 5-vinyl-2-norbornene (VNB) by making cyclopentadiene (CPD) react with butadiene. The present invention uses a non-polar solvent having a relative polarity of 0.15 or less for a reaction, and thus can reduce selectivity of oligomers and THI, which are non-reusable byproducts, and increase the selectivity of 5-vinyl-2-norbornene.(AA) DCP pyrolysis(BB) VNB synthesis(CC) THI separation(DD) BD/CPD separation(EE) VCH separation(FF) VNB separationCOPYRIGHT KIPO 2020
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Paragraph 0027-0038
(2020/09/02)
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- Method for Production of 5-Vinyl-2-Norbornene Using Porous Titanosilicate Catalyst
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The present invention relates to a method for manufacturing 5-vinyl-2-norbornene (VNB) by conducting reaction of cyclopentadiene (CPD) with 1,3-butadiene (BD). The method uses a porous titanosilicate catalyst, thereby providing an effect of increasing the selectivity of VNB and reducing the selectivity of by-product oligomer.(AA) CPD conversion ratio (%)(BB) VNB selectivity (%)(CC) THI selectivity (%)(DD) DCPD selectivity (%)(EE) Oligomer selectivity (%)(FF) Conversion ratio and selectivity (%)COPYRIGHT KIPO 2020
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Paragraph 0036-0040; 0045-0046
(2020/09/10)
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- METHOD OF PREPARING 5-VINYL-2-NORBORNENE THROUGH ALKOXYLATION
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The present invention provides a method for producing 5-vinyl-2-norbornene with excellent selectivity and in high yield from cyclopentadiene and 1,3-butadiene using an alkoxylation reaction.COPYRIGHT KIPO 2020
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Paragraph 0035; 0038
(2020/09/01)
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- Method for Production of 5-Vinyl-2-Norbornene Using Zeolite Catalyst substituted with Sn
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The present invention relates to a method for producing 5-vinyl-2-norbornene (VNB) by inducing a Diels-Alder reaction of cyclopentadiene (CPD) and 1,3-butadiene (BD). The present invention provides an effect of increasing selectivity of 5-vinyl-2-norbornene and decreasing selectivity of an oligomer which is a byproduct by using a zeolite catalyst substituted with tin.(AA) CDP conversion ratio (%)(BB) VNB selectivity (%)(CC) THI selectivity (%)(DD) DCPD selectivity (%)(EE) Oligomer selectivity (%)(FF) Conversion ratio and selectivity (%)COPYRIGHT KIPO 2020
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Paragraph 0037-0038; 0048
(2020/09/01)
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- METHOD OF PREPARING 5-VINYL-2-NORBORNENE USING XYLENE AS SOLVENT
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The present invention provides a method for preparing 5-vinyl-2-norbornene, comprising a step of making cyclopentadiene react with 1,3-butadiene in the presence of a xylene solvent. According to the present invention, the selectivity of 5-vinyl-2-norbornene and the yield thereof can be remarkably improved by using the xylene solvent.COPYRIGHT KIPO 2020
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Paragraph 0019-0023
(2020/09/01)
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- A multi-out live pressure tubular reactor synthetic vinyl norbornene
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The invention discloses a method for synthesizing vinyl norbornene by using a one-inlet and multiple-outlet variable pressure type tubular reactor, wherein more than two discharge openings are formed in a reaction channel of the tubular reactor in the flowing direction of a material and the pressure is gradually decreased. The method comprises the following step: jointly inputting a cyclopentadiene solution and 1, 3-butadiene from a feed inlet at one time into the reaction channel of the tubular reactor so as to obtain the vinyl norbornene, wherein the reaction temperature of the reaction channel is 120-220 DEG C, the pressure is 20-2MPa and the standing time is 24-120 minutes, and the cyclopentadiene solution consists of cyclopentadiene, dicyclopentadiene and possible inert organic solvents. The invention belongs to a method for safely and efficiently synthesizing vinyl norbornene by using the one-inlet and multiple-outlet variable pressure type tubular reactor.
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Paragraph 0044-0046
(2017/07/05)
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- Through the multi-side live pressure tubular reactor synthesis method of the ethylidene norbornene
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The invention discloses a method for synthesizing ethylidene norbornene by virtue of a multi-lateral-line pressure-variable tubular reactor. The reaction channel of the tubular reactor is provided with a starting material inlet and at least two lateral-line material inlets and the pressure is reduced gradually. The method comprises the following steps: 1) feeding a cyclopentadiene solution into the reaction channel of the tubular reactor from the starting material inlet and feeding 1,3-butadiene into the reaction channel of the tubular reactor from the starting material inlet and any one or more lateral-line material inlets, enabling the cyclopentadiene solution and 1,3-butadiene to have a Diels-Alder addition reaction in the reaction channel of the tubular reactor to obtain vinyl norbornene; 2) performing isomerization on the obtained vinyl norbornene in the tubular reactor subsequently filled with a super basic catalyst to obtain ethylidene norbornene, wherein the reaction temperature is between -10 DEG C and 50 DEG C and the dwell time is 10-69min.
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Paragraph 0043; 0044; 0045; 0046
(2017/08/02)
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- 5-ethylidene-2-norborene ENB method for the production of (by machine translation)
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The invention relates to a production method for ENB (5-ethylene-2-norbornylene) and mainly aims to solve the problems in the prior art that the purity of a product is low and the energy consumption is high. The adopted production method for the ENB comprises the following steps: (1) raw materials and a solvent are sent to a first reaction vessel through a static mixer; (2) the reaction product in the first reaction vessel enters into a light component removing tower, tower top light components return to the first reaction vessel and tower kettle heavy components enter into a heavy component removing tower; (3) the kettle components of the heavy component removing tower enter into a DCPD tower, and tower top distilled liquid is purified to obtain a DCPD product; (4) the heavy component removing tower kettle components enter into a VCH tower, the VCH is obtained at the tower top; tower kettle components enter into a VNB tower, THI is obtained in a VNB tower kettle and the VNB is obtained at the tower top; (5) VNB enters into an isomerization reaction vessel to obtain ENB. The problems are better solved by the technical scheme and the production method can be applied in the ENB production.
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Paragraph 0020-0026
(2017/05/26)
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- Ultrahigh Tg Epoxy Thermosets Based on Insertion Polynorbornenes
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Thermosetting materials (thermosets) are widely used organic materials derived from 3D-network forming monomers. Achieving high glass transition temperature (Tg) thermosets is often a challenging task due to the complexity of designing efficiently and cheaply monomers which are rigid enough to prevent molecular motions within the thermoset. We report here a very simple route to prepare epoxy thermosets with Tg as high as 350 °C, based on insertion polynorbornenes. The epoxy monomer (PNBE(epoxy)) is prepared by the epoxidation of poly(5-vinylnorbornene) obtained by catalytic insertion polymerization of 5-vinylnorbornene. PNBE(epoxy) can be cross-linked with simple biosourced compounds. Alternatively, polar insertion polynorbornene can also be used as cross-linker in the formulation of an epoxy resin, once again resulting in epoxy resins with Tg higher than 300 °C and devoid of degradation at this temperature. Thus, this study clearly demonstrates the viability of catalytic polymerization to access epoxy thermosets with ultrahigh Tg.
- Commarieu, Basile,Potier, Jonathan,Compaore, Moubarak,Dessureault, Sylvain,Goodall, Brian L.,Li, Xu,Claverie, Jerome P.
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p. 920 - 925
(2016/03/09)
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- Method for synthesizing vinyl norbornene through multi-lateral-lines feed type tubular reactor
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The invention discloses a method for synthesizing vinyl norbornene through a multi-lateral-lines feed type tubular reactor. Dicyclopentadiene of high-concentration cyclopentadiene and 1,3-butadiene are used as raw materials and a tubular reactor is adopted to synthesize vinyl norbornene. The tubular reactor adopts a process route of simultaneous multi-lateral-lines feeding of 1,3-butadiene and dicyclopentadiene of high-concentration cyclopentadiene. Dicyclopentadiene of high-concentration cyclopentadiene and 1,3-butadiene are poured into a reaction channel of a reaction section through a feed inlet and any one or more lateral-lines. According to the reaction conditions, temperature is 120-220 DEG C; pressure is 2-15 MPa; retention time is 24-120 min; and the molar ratio of 1,3-butadiene to dicyclopentadiene of high-concentration cyclopentadiene is (0.1-2):1. The method is continuously operated under conditions of high temperature and high pressure. The method has strong controllability, high safety and high yield of vinyl norbornene.
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Paragraph 0035; 0036
(2016/11/17)
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- METHOD OF PRODUCING 5-VINYL-2-NORBORNENE AND METHOD OF RECOVERING POLYMERIZATION INHIBITOR USED IN THE METHOD
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PROBLEM TO BE SOLVED: To provide a method of recovering a polymerization inhibitor which recovers continuously a polymerization inhibitor used in producing 5-vinyl-2-norbornene by a Diels-Alder reaction on an industrial scale and, when the recovered polymerization inhibitor is recycled, does not cause deterioration of quality of 5-vinyl-2-norbornene due to ingredients accompanying the polymerization inhibitor and lowering of productivity. SOLUTION: A method of producing 5-vinyl-2-norbornene includes a reaction step of producing 5-vinyl-2-norbornene by a Diels-Alder reaction of reacting cyclopentadiene with 1,3-butadiene in the presence of a polymerization inhibitor, a purification step of obtaining 5-vinyl-2-norbornene from the reaction product by distillation and a step of extracting the polymerization inhibitor from the distillation residue of the purification step, which contains the polymerization inhibitor, by using an extraction solvent comprising 100-50 mass% of methyl alcohol and 0-50 mass% of water with a total of 100 mass%. COPYRIGHT: (C)2015,JPOandINPIT
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Paragraph 0052
(2016/12/26)
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- Liquid-phase synthesis of cyclic diene diepoxides using metal halides and hydrogen peroxide
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Optimal conditions were found for induced hydroxyhalogenation of cyclic dienes (tetrahydroindene, 4-vinylcyclohexene and 5-vinyl- and 5-cyclohexenylbicyclo[2.2.1]hept-2-enes) in the system [MHlg-HA or HHlg]-H 2O2 (or NaClO). Dehydrohalogenation of the chloro- and bromohydrins thus obtained with powdered potassium carbonate gave the corresponding diepoxy derivatives, and their hydrolysis led to mixtures of stereoisomeric tetrahydric alcohols. Pleiades Publishing, Ltd., 2012.
- Alimardanov, Kh. M.,Sadygov,Garibov,Abdullaeva, M. Ya.
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p. 1302 - 1308
(2013/02/21)
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- PROCESS FOR PRODUCING HIGH PURITY EXO-ALKENYLNORBORNENE
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Embodiments of the present invention are directed generally to methods for producing high purity exo-alkenylnorbornenes from a mixture of conformational isomers thereof.
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Page/Page column 13-14
(2009/07/02)
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- Isomerization of olefins in the presence of reactive impurities
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A process and catalyst for isomerizing olefins are disclosed. The process and catalyst are particularly useful for isomerizing alkenyl bridged ring compounds to the corresponding alkyladiene bridged ring compounds. In one embodiment, the isomerization catalyst comprises an oxygen treated mixture of an alkali metal on a dried support having a surface area of 125 to 195 m2 /g when the support consists essentially of alumina wherein the alumina precursor is a large crystallite pseudoboehmite. The catalyst is particularly useful for isomerizing 5-vinyl-2-norbornene to 5-ethylidiene-2-norbornene. The catalyst is very active and highly selective and resistant to catalyst poisons. The process contacts the catalyst with an alkenyl bridged ring compound and yields the corresponding alkyladiene bridged ring compound.
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- Application of molecular dynamics to chromatographic-spectral identification of isomeric products of organic reactions
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Isomeric products of [2+4]-cycloaddition reactions can be identified by gas chromatography-mass spectrometry on the basis of their experimental retention parameters and intramolecular vibrational and rotational energies (E) calculated by molecular mechanics for all possible isomers. The Chromatographic parameters change in the opposite direction with respect to E. The proposed approach allows unambiguous identification of four products formed by each of the reactions of butadiene with cyclopentadiene, of isoprene with 2,3-dimethylbutadiene, of cyclopentadiene with isoprene, and dimerization of isoprene and two of the four products formed by the reaction of 1,3-cyclohexadiene with cyclopentadiene. Both structural and steric isomers (exo, endo) can be distinguished. 1998 MAHK "Hayka/Interperiodica".
- Zenkevich
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p. 1403 - 1409
(2007/10/03)
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- Catalyst and process for the isomerization of olefins in the presence of reactive impurities
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A process and catalyst for isomerizing olefins are disclosed. The process and catalyst are particularly useful for isomerizing alkenyl bridged ring compounds to the corresponding alkyladiene bridged ring compounds. In one embodiment, the isomerization catalyst comprises an oxygen treated mixture of an alkali metal on a dried support having a surface area of 125 to 195 m2 /g when the support consists essentially of alumina wherein the alumina precursor is a large crystallite pseudoboehmite. The catalyst is particularly useful for isomerizing 5-vinyl-2-norbornene to 5-ethylidiene-2-norbornene. The catalyst is very active and highly selective and resistant to catalyst poisons. The process contacts the catalyst with an alkenyl bridged ring compound and yields the corresponding alkyladiene bridged ring compound.
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- Multi-stage olefin isomerization
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A multi-stage process for isomerizing olefin compounds to the corresponding product olefin compounds is provided. The isomerization catalyst comprises an oxygen treated mixture of an alkali metal on a calcined support. The multi-stage process is particularly useful for isomerizing 5-vinyl-2-norbornene to 5-ethylidiene-2-norbornene. The catalyst is very active and highly selective and resistent to catalyst poisons. The process contacts the catalyst with an isomerizable olefin in at least two reaction stages to yield the corresponding product olefin compound. The reaction stages differ in temperature, catalyst activity or both.
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- Useful Synthetic Routes to Pure exo-5-Vinyl-2-norbornene and endo-5-Vinyl-2-norbornene
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Hydroboration of 5-vinyl-2-norbornene (1) with 9-BBN mainly affords 5-(2-hydroxyethyl)-2- norbornene (2).The iodo ether cyclization of 2 can convert only endo-5-(2-hydroxyethyl)-2-norbornene (2b) to iodo ether 10, followed by reductive elimination and subsequent dehydration to furnish endo-5-vinyl-2-norbornene (1b) which has not been isolated in pure form.Meanwhile, unreacted exo-5-(2-hydroxyethyl)-2-norbornene (2a) produces exo-5-vinyl-2-norbornene (1a) via dehydration.
- Inoue, Yoshiharu
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p. 1954 - 1956
(2007/10/02)
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- Traction drive fluid
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A traction drive fluid comprising as a base stock at least one hydrocarbon selected from the group consisting of compounds of the following general formulae (I) to (V) STR1 wherein R1, R2 and R3, independently from each other, represent a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and R4, R5, R6, R7, R8, R9 and R10, independently from each other, represent a hydrogen atom or a methyl group.
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- Preparation of New Solid Superbase and Its Catalityc Activity
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A solid superbase whose basicity (H-) was higher than 37 was prepared by the successive treatment of γ-alumina with sodium hydroxyde and sodium at 280-350 deg C under nitrogen.The base was highly effective in the catalytic isomerization of 5-vinylbicyclohept-2-ene to 5-ethylidenebicyclohept-2-ene.
- Suzukamo, Gohfu,Fukao, Masami,Minobe, Masao
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p. 585 - 588
(2007/10/02)
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