CA2127692C - Diels-alder process - Google Patents
Diels-alder process Download PDFInfo
- Publication number
- CA2127692C CA2127692C CA002127692A CA2127692A CA2127692C CA 2127692 C CA2127692 C CA 2127692C CA 002127692 A CA002127692 A CA 002127692A CA 2127692 A CA2127692 A CA 2127692A CA 2127692 C CA2127692 C CA 2127692C
- Authority
- CA
- Canada
- Prior art keywords
- vinylcyclohexene
- cyclopentadiene
- adduct
- product
- adducts
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 238000000034 method Methods 0.000 title claims abstract description 30
- 238000005698 Diels-Alder reaction Methods 0.000 title description 16
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims abstract description 103
- BBDKZWKEPDTENS-UHFFFAOYSA-N 4-Vinylcyclohexene Chemical compound C=CC1CCC=CC1 BBDKZWKEPDTENS-UHFFFAOYSA-N 0.000 claims abstract description 45
- 239000000203 mixture Substances 0.000 claims abstract description 32
- 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 abstract description 37
- 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 abstract description 18
- 238000004519 manufacturing process Methods 0.000 abstract description 13
- 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 abstract description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 229920001187 thermosetting polymer Polymers 0.000 description 7
- 239000000463 material Substances 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 4
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 4
- SDRZFSPCVYEJTP-UHFFFAOYSA-N 1-ethenylcyclohexene Chemical compound C=CC1=CCCCC1 SDRZFSPCVYEJTP-UHFFFAOYSA-N 0.000 description 3
- 238000005865 alkene metathesis reaction Methods 0.000 description 3
- 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
- 238000006116 polymerization reaction Methods 0.000 description 3
- 239000000376 reactant Substances 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
- 238000005649 metathesis reaction Methods 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
- 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
- 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
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 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
- 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
- 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
- 238000002360 preparation method Methods 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 (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US81903792A | 1992-01-10 | 1992-01-10 | |
| US819,037 | 1992-01-10 | ||
| US07/987,096 US5260498A (en) | 1992-01-10 | 1992-12-07 | Diels-Alder process |
| US987,096 | 1992-12-07 | ||
| PCT/US1993/000127 WO1993014050A1 (en) | 1992-01-10 | 1993-01-08 | Diels-alder process |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2127692A1 CA2127692A1 (en) | 1993-07-22 |
| CA2127692C true CA2127692C (en) | 2003-11-11 |
Family
ID=27124327
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002127692A Expired - Fee Related CA2127692C (en) | 1992-01-10 | 1993-01-08 | 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 |
| NZ246801A (en) | 1996-05-28 |
| EP0620807A1 (en) | 1994-10-26 |
| JP3210339B2 (ja) | 2001-09-17 |
| KR100278930B1 (ko) | 2001-01-15 |
| EP0620807B1 (en) | 1997-06-18 |
| US5260498A (en) | 1993-11-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |