CN1042220C - 狄尔斯-阿德尔方法 - Google Patents
狄尔斯-阿德尔方法 Download PDFInfo
- Publication number
- CN1042220C CN1042220C CN93101192A CN93101192A CN1042220C CN 1042220 C CN1042220 C CN 1042220C CN 93101192 A CN93101192 A CN 93101192A CN 93101192 A CN93101192 A CN 93101192A CN 1042220 C CN1042220 C CN 1042220C
- Authority
- CN
- China
- Prior art keywords
- adducts
- product
- mole
- vinyl cyclohexene
- heavy
- 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 33
- 238000005698 Diels-Alder reaction Methods 0.000 title description 4
- BBDKZWKEPDTENS-UHFFFAOYSA-N 4-Vinylcyclohexene Chemical compound C=CC1CCC=CC1 BBDKZWKEPDTENS-UHFFFAOYSA-N 0.000 claims abstract description 37
- 239000000203 mixture Substances 0.000 claims abstract description 24
- 238000004519 manufacturing process Methods 0.000 claims abstract description 5
- 238000004821 distillation Methods 0.000 claims description 7
- 230000006353 environmental stress Effects 0.000 claims description 3
- 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 15
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 abstract description 6
- 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 1
- 238000004064 recycling Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 description 28
- 238000006116 polymerization reaction Methods 0.000 description 8
- 239000000463 material Substances 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 229920001187 thermosetting polymer Polymers 0.000 description 6
- 241000219495 Betulaceae Species 0.000 description 5
- 238000004132 cross linking Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000005865 alkene metathesis reaction Methods 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- -1 polycyclic olefin Chemical class 0.000 description 4
- 239000004634 thermosetting polymer Substances 0.000 description 4
- SDRZFSPCVYEJTP-UHFFFAOYSA-N 1-ethenylcyclohexene Chemical compound C=CC1=CCCCC1 SDRZFSPCVYEJTP-UHFFFAOYSA-N 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000005194 fractionation Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000013638 trimer Substances 0.000 description 3
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- LDLDYFCCDKENPD-UHFFFAOYSA-N ethenylcyclohexane Chemical compound C=CC1CCCCC1 LDLDYFCCDKENPD-UHFFFAOYSA-N 0.000 description 2
- OTTZHAVKAVGASB-UHFFFAOYSA-N hept-2-ene Chemical compound CCCCC=CC OTTZHAVKAVGASB-UHFFFAOYSA-N 0.000 description 2
- 238000005649 metathesis reaction Methods 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- VGLHILPZFIDIJH-UHFFFAOYSA-N 2-cyclohex-2-en-1-ylbicyclo[2.2.1]hept-2-ene Chemical group C1CC2CC1C=C2C1CCCC=C1 VGLHILPZFIDIJH-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
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 229940123457 Free radical scavenger Drugs 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
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000003965 capillary gas chromatography Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 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
- 229920001577 copolymer Polymers 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 230000002349 favourable effect Effects 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
- 238000013007 heat curing Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000005574 norbornylene group Chemical group 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000012856 packing Methods 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
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 238000007152 ring opening metathesis polymerisation reaction Methods 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 239000003566 sealing material Substances 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
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
Landscapes
- 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 | |
| US819,037 | 1992-01-10 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1076924A CN1076924A (zh) | 1993-10-06 |
| CN1042220C true CN1042220C (zh) | 1999-02-24 |
Family
ID=25227050
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN93101192A Expired - Fee Related CN1042220C (zh) | 1992-01-10 | 1993-01-09 | 狄尔斯-阿德尔方法 |
Country Status (2)
| Country | Link |
|---|---|
| CN (1) | CN1042220C (enrdf_load_stackoverflow) |
| TW (1) | TW229214B (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1308305C (zh) * | 2005-04-21 | 2007-04-04 | 浙江工业大学 | 合成酰亚胺基取代的桥环化合物的方法 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1449053A (en) * | 1973-02-21 | 1976-09-08 | Ici Ltd | Propenylnorbornen separation process |
| EP0229987A1 (en) * | 1986-01-18 | 1987-07-29 | Sumitomo Chemical Company, Limited | A continuous process for producing 5-vinyl-2-norbornene |
-
1993
- 1993-01-06 TW TW82100052A patent/TW229214B/zh active
- 1993-01-09 CN CN93101192A patent/CN1042220C/zh not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1449053A (en) * | 1973-02-21 | 1976-09-08 | Ici Ltd | Propenylnorbornen separation process |
| EP0229987A1 (en) * | 1986-01-18 | 1987-07-29 | Sumitomo Chemical Company, Limited | A continuous process for producing 5-vinyl-2-norbornene |
Also Published As
| Publication number | Publication date |
|---|---|
| TW229214B (enrdf_load_stackoverflow) | 1994-09-01 |
| CN1076924A (zh) | 1993-10-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| C19 | Lapse of patent right due to non-payment of the annual fee | ||
| CF01 | Termination of patent right due to non-payment of annual fee |