NZ246801A - Preparation of 5-(3-cyclohexen-1-yl)-2-norbornene; diels alder process - Google Patents
Preparation of 5-(3-cyclohexen-1-yl)-2-norbornene; diels alder processInfo
- Publication number
- NZ246801A NZ246801A NZ246801A NZ24680193A NZ246801A NZ 246801 A NZ246801 A NZ 246801A NZ 246801 A NZ246801 A NZ 246801A NZ 24680193 A NZ24680193 A NZ 24680193A NZ 246801 A NZ246801 A NZ 246801A
- Authority
- NZ
- New Zealand
- Prior art keywords
- cyclopentadiene
- adduct
- vinylcyclohexene
- product
- process according
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 33
- 238000005698 Diels-Alder reaction Methods 0.000 title description 17
- KKCXDWJDGRCIAB-UHFFFAOYSA-N 5-cyclohex-3-en-1-ylbicyclo[2.2.1]hept-2-ene Chemical compound C1=CC2CC1CC2C1CCC=CC1 KKCXDWJDGRCIAB-UHFFFAOYSA-N 0.000 title description 9
- 238000002360 preparation method Methods 0.000 title description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 101
- BBDKZWKEPDTENS-UHFFFAOYSA-N 4-Vinylcyclohexene Chemical compound C=CC1CCC=CC1 BBDKZWKEPDTENS-UHFFFAOYSA-N 0.000 claims description 41
- 239000000203 mixture Substances 0.000 claims description 31
- 238000000926 separation method Methods 0.000 claims description 12
- 238000004821 distillation Methods 0.000 claims description 7
- 238000004064 recycling Methods 0.000 claims 1
- 239000000047 product Substances 0.000 description 32
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 17
- 238000004519 manufacturing process Methods 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 7
- 229920001187 thermosetting polymer Polymers 0.000 description 7
- 239000000463 material Substances 0.000 description 6
- SDRZFSPCVYEJTP-UHFFFAOYSA-N 1-ethenylcyclohexene Chemical compound C=CC1=CCCCC1 SDRZFSPCVYEJTP-UHFFFAOYSA-N 0.000 description 4
- 238000005865 alkene metathesis reaction Methods 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 150000001336 alkenes Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 3
- 239000013638 trimer Substances 0.000 description 3
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 239000003431 cross linking reagent Substances 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- -1 polycyclic olefins Chemical class 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 229920001169 thermoplastic Polymers 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 1
- OTTZHAVKAVGASB-UHFFFAOYSA-N 2-heptene Natural products CCCCC=CC OTTZHAVKAVGASB-UHFFFAOYSA-N 0.000 description 1
- JIGUICYYOYEXFS-UHFFFAOYSA-N 3-tert-butylbenzene-1,2-diol Chemical compound CC(C)(C)C1=CC=CC(O)=C1O JIGUICYYOYEXFS-UHFFFAOYSA-N 0.000 description 1
- 241000566113 Branta sandvicensis Species 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 229940123457 Free radical scavenger Drugs 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000003965 capillary gas chromatography Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- LDLDYFCCDKENPD-UHFFFAOYSA-N ethenylcyclohexane Chemical compound C=CC1CCCCC1 LDLDYFCCDKENPD-UHFFFAOYSA-N 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- LJKNRSBEKUSSIE-UHFFFAOYSA-N hept-2-ene Chemical compound [CH2]CCCC=CC LJKNRSBEKUSSIE-UHFFFAOYSA-N 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 239000012035 limiting reagent Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000005649 metathesis reaction Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 125000003518 norbornenyl group Chemical group C12(C=CC(CC1)C2)* 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 238000007152 ring opening metathesis polymerisation reaction Methods 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/39—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with a bicyclo ring system containing seven carbon atoms
- C07C13/42—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with a bicyclo ring system containing seven carbon atoms with a bicycloheptene ring structure
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/02—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons
- C07C2/50—Diels-Alder conversion
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US81903792A | 1992-01-10 | 1992-01-10 | |
| US07/987,096 US5260498A (en) | 1992-01-10 | 1992-12-07 | Diels-Alder process |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ246801A true NZ246801A (en) | 1996-05-28 |
Family
ID=27124327
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ246801A NZ246801A (en) | 1992-01-10 | 1993-01-08 | Preparation of 5-(3-cyclohexen-1-yl)-2-norbornene; diels alder process |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US5260498A (online.php) |
| EP (1) | EP0620807B1 (online.php) |
| JP (1) | JP3210339B2 (online.php) |
| KR (1) | KR100278930B1 (online.php) |
| AU (1) | AU667873B2 (online.php) |
| CA (1) | CA2127692C (online.php) |
| DE (1) | DE69311699T2 (online.php) |
| NZ (1) | NZ246801A (online.php) |
| WO (1) | WO1993014050A1 (online.php) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5495051A (en) | 1994-08-22 | 1996-02-27 | Shell Oil Company | Phenolic allyl ethers |
| US6380447B1 (en) * | 2000-06-09 | 2002-04-30 | Wake Forest University | Diels-alder adducts of epoxybutene and epoxybutene derivatives |
| CN117164422A (zh) * | 2022-05-26 | 2023-12-05 | 万华化学集团股份有限公司 | 一种降冰片烯工艺副产物的回收方法及降冰片烯的生产方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1227894B (de) * | 1963-06-14 | 1966-11-03 | Consortium Elektrochem Ind | Verfahren zur Kondensation von 1-Vinylcyclohex-3-en mit Dicyclopentadien |
| JPS5138380B2 (online.php) * | 1972-07-05 | 1976-10-21 | ||
| JPS60190728A (ja) * | 1984-03-09 | 1985-09-28 | San Petoro Chem:Kk | アルキリデンノルボルネンの製造法 |
| JPS6392640A (ja) * | 1986-10-08 | 1988-04-23 | Teijin Ltd | 重合体、その成型物及び反応性溶液の組合せ |
| EP0287762A3 (en) * | 1987-02-16 | 1991-01-23 | Hercules Incorporated | Methathesis polymerized copolymer |
| US5196621A (en) * | 1991-04-19 | 1993-03-23 | The Dow Chemical Company | Process for the cyclodimerization of 1,3-butadienes to 4-vinylcyclohexenes |
| US5095082A (en) * | 1991-06-10 | 1992-03-10 | Shell Oil Company | Polymerization process employing mixture of Diels-Alder adducts of 4-vinylcyclohexene and cyclopentadiene |
| US5143992A (en) * | 1991-07-12 | 1992-09-01 | Shell Oil Company | Methathesis polymerizable adducts of a divinylcyclohydrocarbon and cyclopentadiene |
-
1992
- 1992-12-07 US US07/987,096 patent/US5260498A/en not_active Expired - Lifetime
-
1993
- 1993-01-08 AU AU34376/93A patent/AU667873B2/en not_active Ceased
- 1993-01-08 WO PCT/US1993/000127 patent/WO1993014050A1/en not_active Ceased
- 1993-01-08 NZ NZ246801A patent/NZ246801A/en unknown
- 1993-01-08 CA CA002127692A patent/CA2127692C/en not_active Expired - Fee Related
- 1993-01-08 DE DE69311699T patent/DE69311699T2/de not_active Expired - Fee Related
- 1993-01-08 KR KR1019940702386A patent/KR100278930B1/ko not_active Expired - Fee Related
- 1993-01-08 JP JP51257393A patent/JP3210339B2/ja not_active Expired - Fee Related
- 1993-01-08 EP EP93903002A patent/EP0620807B1/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| AU3437693A (en) | 1993-08-03 |
| JPH07503011A (ja) | 1995-03-30 |
| DE69311699T2 (de) | 1997-10-30 |
| DE69311699D1 (de) | 1997-07-24 |
| WO1993014050A1 (en) | 1993-07-22 |
| CA2127692A1 (en) | 1993-07-22 |
| KR940703796A (ko) | 1994-12-12 |
| AU667873B2 (en) | 1996-04-18 |
| EP0620807A1 (en) | 1994-10-26 |
| JP3210339B2 (ja) | 2001-09-17 |
| KR100278930B1 (ko) | 2001-01-15 |
| EP0620807B1 (en) | 1997-06-18 |
| CA2127692C (en) | 2003-11-11 |
| US5260498A (en) | 1993-11-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2110978C (en) | Polymerization process and products | |
| US3660516A (en) | Neohexene from isobutene and ethylene | |
| US5260498A (en) | Diels-Alder process | |
| US3258501A (en) | Production of polycyclic compounds | |
| EP0359186A2 (en) | Liquid dicyclopentadiene feedstock for bulk polymerization | |
| US3577473A (en) | Method for producing 5-isopropylidene-2-norbornene | |
| Darabi et al. | Synthesis, properties and molecular structure of a new isomer of [2.4]-paracyclophanetetraene:(E, Z, E, Z)-[2.4]-paracyclophanetetraene | |
| US3238251A (en) | Production of substituted naphthalene derivatives by rearrangement of substituted dicyclopentadiene derivatives with a friedel-crafts catalyst | |
| US3265749A (en) | Production of polycyclic compounds | |
| US4219688A (en) | Process for producing vinylnorbornene and/or tetrahydroindene | |
| US3418387A (en) | Process for the production of adamantane | |
| CA1110667A (en) | Process for the preparation of substituted norbornene derivatives | |
| CA1215399A (en) | Manufacture of norbornene | |
| US3766283A (en) | Preparation of norbornenes | |
| US3890402A (en) | Oligomerization process | |
| US3996262A (en) | Method of promoting the reaction of unsaturated nitriles with olefins to produce unsaturated nitriles of increased carbon number | |
| US3282663A (en) | Bicycloheptadiene oligomers | |
| EP0595979B1 (en) | Polymerization process for cycloolefins | |
| US3258502A (en) | Polycyclic hydrocarbon production | |
| US3629347A (en) | Cycloco-oligomerization to form multicyclic olefinic rings | |
| CN1042220C (zh) | 狄尔斯-阿德尔方法 | |
| US3565962A (en) | Production of a polycyclic diene | |
| US3417160A (en) | Dimerisation process | |
| US3440294A (en) | Oligomers of bicycloheptadiene | |
| JP2003082073A (ja) | 環状オレフィン単量体組成物およびその製造方法ならびに環状オレフィン重合体組成物および環状オレフィン重合体水素化組成物 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| RENW | Renewal (renewal fees accepted) |