SU338087A1 - Способ получени алкилидензамещенных норборненов - Google Patents
Способ получени алкилидензамещенных норборненов Download PDFInfo
- Publication number
- SU338087A1 SU338087A1 SU701466965A SU1466965A SU338087A1 SU 338087 A1 SU338087 A1 SU 338087A1 SU 701466965 A SU701466965 A SU 701466965A SU 1466965 A SU1466965 A SU 1466965A SU 338087 A1 SU338087 A1 SU 338087A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- reaction
- catalyst
- norbornene
- isomerization
- sodium
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 13
- 125000001118 alkylidene group Chemical group 0.000 title description 2
- 239000003054 catalyst Substances 0.000 claims abstract description 25
- INYHZQLKOKTDAI-UHFFFAOYSA-N 5-ethenylbicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(C=C)CC1C=C2 INYHZQLKOKTDAI-UHFFFAOYSA-N 0.000 claims abstract description 11
- 238000006317 isomerization reaction Methods 0.000 claims abstract description 11
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 10
- OJOWICOBYCXEKR-KRXBUXKQSA-N (5e)-5-ethylidenebicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(=C/C)/CC1C=C2 OJOWICOBYCXEKR-KRXBUXKQSA-N 0.000 claims abstract description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims abstract description 9
- -1 alkenyl norbornenes Chemical class 0.000 claims abstract description 9
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 7
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 7
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 6
- 229940072033 potash Drugs 0.000 claims abstract description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims abstract description 6
- 235000015320 potassium carbonate Nutrition 0.000 claims abstract description 6
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 5
- 150000001342 alkaline earth metals Chemical class 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 4
- 239000003513 alkali Substances 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 18
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 13
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 11
- 229910052708 sodium Inorganic materials 0.000 claims description 11
- 239000011734 sodium Substances 0.000 claims description 11
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 6
- 238000002474 experimental method Methods 0.000 claims description 5
- 230000035484 reaction time Effects 0.000 claims description 4
- 229910052786 argon Inorganic materials 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 239000003153 chemical reaction reagent Substances 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims 1
- 235000011114 ammonium hydroxide Nutrition 0.000 claims 1
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 claims 1
- 150000002848 norbornenes Chemical class 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- 229910018072 Al 2 O 3 Inorganic materials 0.000 abstract 1
- 239000005995 Aluminium silicate Substances 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract 1
- 229910021536 Zeolite Inorganic materials 0.000 abstract 1
- PZZYQPZGQPZBDN-UHFFFAOYSA-N aluminium silicate Chemical compound O=[Al]O[Si](=O)O[Al]=O PZZYQPZGQPZBDN-UHFFFAOYSA-N 0.000 abstract 1
- 229910000323 aluminium silicate Inorganic materials 0.000 abstract 1
- 235000012211 aluminium silicate Nutrition 0.000 abstract 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 239000000741 silica gel Substances 0.000 abstract 1
- 229910002027 silica gel Inorganic materials 0.000 abstract 1
- 239000010457 zeolite Substances 0.000 abstract 1
- 239000011521 glass Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 125000003518 norbornenyl group Chemical class C12(C=CC(CC1)C2)* 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- 150000001341 alkaline earth metal compounds Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 235000013601 eggs Nutrition 0.000 description 1
- 238000001030 gas--liquid chromatography Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
- 229910001948 sodium oxide Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 210000004243 sweat Anatomy 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/22—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by isomerisation
- C07C5/23—Rearrangement of carbon-to-carbon unsaturated bonds
- C07C5/25—Migration of carbon-to-carbon double bonds
- C07C5/2506—Catalytic processes
- C07C5/2556—Catalytic processes with metals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU701466965A SU338087A1 (ru) | 1970-07-28 | 1970-07-28 | Способ получени алкилидензамещенных норборненов |
| BE769324A BE769324A (fr) | 1970-07-28 | 1971-06-30 | Procede de preparation d'alcoylidenenorbornenes et produits obtenus |
| DE19712133414 DE2133414C3 (de) | 1970-07-28 | 1971-07-05 | Verfahren zur Herstellung alkylidensubstituierter Norbornene |
| GB3181971A GB1335138A (en) | 1970-07-28 | 1971-07-07 | Method of producing alkylidene-substituted norbornenes |
| IT748971A IT941576B (it) | 1970-07-28 | 1971-07-20 | Metodo di produzione di norborneni alchiliden sostituiti |
| NL7110080A NL159946C (nl) | 1970-07-28 | 1971-07-22 | Werkwijze voor het bereiden van alkylideen gesubstitueerde norbornenen, door isomerisatie van alkenylnorbornenen met behulp van een basische katalysator. |
| PL14958471A PL82185B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1970-07-28 | 1971-07-23 | |
| FR7127475A FR2103738A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1970-07-28 | 1971-07-27 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU701466965A SU338087A1 (ru) | 1970-07-28 | 1970-07-28 | Способ получени алкилидензамещенных норборненов |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU338087A1 true SU338087A1 (ru) | 1980-04-05 |
Family
ID=20456150
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU701466965A SU338087A1 (ru) | 1970-07-28 | 1970-07-28 | Способ получени алкилидензамещенных норборненов |
Country Status (8)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2721911C1 (ru) * | 2019-11-08 | 2020-05-25 | Общество с ограниченной ответственностью "Объединенный центр исследований и разработок" (ООО "РН-ЦИР") | Способ получения катализатора изомеризации 5-винил-2-норборнена в 5-этилиден-2-норборнен |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS53121753A (en) | 1977-03-31 | 1978-10-24 | Japan Synthetic Rubber Co Ltd | Preparation of 5-alkylidenenorbornene |
| EP0211448B1 (en) * | 1985-08-16 | 1990-11-14 | Sumitomo Chemical Company, Limited | Process for preparing solid base |
| EP0219637B1 (en) * | 1985-10-21 | 1990-10-31 | Sumitomo Chemical Company, Limited | Process for preparing 5-ethylidene-2-norbornene |
| MX169136B (es) * | 1985-12-20 | 1993-06-23 | Sumitomo Chemical Co | Procedimiento para preparar 5-etiliden-2-norborneno de alta calidad |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1495709A (fr) * | 1965-10-01 | 1967-09-22 | Union Carbide Corp | Procédé de production de 5-alkylidènebicyclo[2. 2. 1]hept-2-ènes |
| DE1568538A1 (de) * | 1966-06-07 | 1970-03-19 | Hoechst Ag | Verfahren zur Herstellung von 5-Alkyliden-norbornenen |
| DE1568543A1 (de) * | 1966-06-29 | 1970-05-06 | Hoechst Ag | Verfahren zur Herstellung von 5-Alkyliden-norbornenen |
| US3577473A (en) * | 1967-10-25 | 1971-05-04 | Sumitomo Chemical Co | Method for producing 5-isopropylidene-2-norbornene |
-
1970
- 1970-07-28 SU SU701466965A patent/SU338087A1/ru active
-
1971
- 1971-06-30 BE BE769324A patent/BE769324A/xx not_active IP Right Cessation
- 1971-07-05 DE DE19712133414 patent/DE2133414C3/de not_active Expired
- 1971-07-07 GB GB3181971A patent/GB1335138A/en not_active Expired
- 1971-07-20 IT IT748971A patent/IT941576B/it active
- 1971-07-22 NL NL7110080A patent/NL159946C/xx not_active IP Right Cessation
- 1971-07-23 PL PL14958471A patent/PL82185B1/pl unknown
- 1971-07-27 FR FR7127475A patent/FR2103738A5/fr not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2721911C1 (ru) * | 2019-11-08 | 2020-05-25 | Общество с ограниченной ответственностью "Объединенный центр исследований и разработок" (ООО "РН-ЦИР") | Способ получения катализатора изомеризации 5-винил-2-норборнена в 5-этилиден-2-норборнен |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2103738A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1972-04-14 |
| IT941576B (it) | 1973-03-10 |
| NL159946C (nl) | 1979-09-17 |
| DE2133414A1 (de) | 1972-02-03 |
| PL82185B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-10-31 |
| DE2133414B2 (de) | 1980-08-07 |
| BE769324A (fr) | 1971-12-30 |
| GB1335138A (en) | 1973-10-24 |
| NL159946B (nl) | 1979-04-17 |
| DE2133414C3 (de) | 1981-03-12 |
| NL7110080A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1972-02-01 |
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