DE3035549A1 - Verfahren zur chemischen umsetzung von cyclopentadien mit (alpha) - (beta) -ungesaettigten, organischen verbindungen nach der diels-alder-reaktion und zur gewinnung der hierbei entstehenden addukt-verbindungen - Google Patents
Verfahren zur chemischen umsetzung von cyclopentadien mit (alpha) - (beta) -ungesaettigten, organischen verbindungen nach der diels-alder-reaktion und zur gewinnung der hierbei entstehenden addukt-verbindungenInfo
- Publication number
- DE3035549A1 DE3035549A1 DE19803035549 DE3035549A DE3035549A1 DE 3035549 A1 DE3035549 A1 DE 3035549A1 DE 19803035549 DE19803035549 DE 19803035549 DE 3035549 A DE3035549 A DE 3035549A DE 3035549 A1 DE3035549 A1 DE 3035549A1
- Authority
- DE
- Germany
- Prior art keywords
- adduct
- cyclopentadiene
- endo
- acrylic acid
- exo
- 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.)
- Granted
Links
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 title claims abstract description 44
- 239000007787 solid Substances 0.000 title claims abstract description 21
- 238000005698 Diels-Alder reaction Methods 0.000 title claims abstract description 8
- 239000002245 particle Substances 0.000 title claims abstract description 6
- 239000003960 organic solvent Substances 0.000 title claims abstract description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 title abstract 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 title abstract 2
- 238000010828 elution Methods 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 21
- 238000006243 chemical reaction Methods 0.000 claims abstract description 15
- 239000000203 mixture Substances 0.000 claims description 28
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 16
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 claims description 13
- 239000000741 silica gel Substances 0.000 claims description 11
- 229910002027 silica gel Inorganic materials 0.000 claims description 11
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 10
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 9
- 239000000376 reactant Substances 0.000 claims description 8
- 239000004576 sand Substances 0.000 claims description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 6
- 239000001913 cellulose Substances 0.000 claims description 6
- 229920002678 cellulose Polymers 0.000 claims description 6
- 229910052593 corundum Inorganic materials 0.000 claims description 6
- 229910001845 yogo sapphire Inorganic materials 0.000 claims description 6
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 150000002894 organic compounds Chemical class 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- LCMDGWVEJOWHOY-UHFFFAOYSA-N cyclopenta-1,3-diene;methyl prop-2-enoate Chemical compound C1C=CC=C1.COC(=O)C=C LCMDGWVEJOWHOY-UHFFFAOYSA-N 0.000 claims description 2
- AEUHGYNMKYDZKZ-UHFFFAOYSA-N cyclopenta-1,3-diene;prop-2-enal Chemical compound C=CC=O.C1C=CC=C1 AEUHGYNMKYDZKZ-UHFFFAOYSA-N 0.000 claims description 2
- TYLPEEKJMNOMSF-UHFFFAOYSA-N cyclopenta-1,3-diene;prop-2-enenitrile Chemical compound C=CC#N.C1C=CC=C1 TYLPEEKJMNOMSF-UHFFFAOYSA-N 0.000 claims description 2
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 229910052901 montmorillonite Inorganic materials 0.000 claims description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 2
- 238000006073 displacement reaction Methods 0.000 claims 3
- 238000000605 extraction Methods 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 239000000417 fungicide Substances 0.000 abstract description 2
- 238000005984 hydrogenation reaction Methods 0.000 abstract description 2
- 230000008707 rearrangement Effects 0.000 abstract description 2
- 238000006467 substitution reaction Methods 0.000 abstract description 2
- FYGUSUBEMUKACF-UHFFFAOYSA-N bicyclo[2.2.1]hept-2-ene-5-carboxylic acid Chemical compound C1C2C(C(=O)O)CC1C=C2 FYGUSUBEMUKACF-UHFFFAOYSA-N 0.000 abstract 1
- 239000004009 herbicide Substances 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 238000011084 recovery Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 description 10
- 239000012071 phase Substances 0.000 description 6
- 239000007788 liquid Substances 0.000 description 5
- 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 4
- 238000007259 addition reaction Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- -1 cyclic dienes Chemical class 0.000 description 2
- 150000001993 dienes Chemical class 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000008241 heterogeneous mixture Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- RMAZRAQKPTXZNL-UHFFFAOYSA-N methyl bicyclo[2.2.1]hept-2-ene-5-carboxylate Chemical compound C1C2C(C(=O)OC)CC1C=C2 RMAZRAQKPTXZNL-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000006462 rearrangement reaction Methods 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000001149 thermolysis Methods 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
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/69—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by addition to carbon-to-carbon double or triple bonds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803035549 DE3035549A1 (de) | 1980-09-20 | 1980-09-20 | Verfahren zur chemischen umsetzung von cyclopentadien mit (alpha) - (beta) -ungesaettigten, organischen verbindungen nach der diels-alder-reaktion und zur gewinnung der hierbei entstehenden addukt-verbindungen |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803035549 DE3035549A1 (de) | 1980-09-20 | 1980-09-20 | Verfahren zur chemischen umsetzung von cyclopentadien mit (alpha) - (beta) -ungesaettigten, organischen verbindungen nach der diels-alder-reaktion und zur gewinnung der hierbei entstehenden addukt-verbindungen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3035549A1 true DE3035549A1 (de) | 1982-04-29 |
| DE3035549C2 DE3035549C2 (enrdf_load_stackoverflow) | 1989-02-09 |
Family
ID=6112452
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19803035549 Granted DE3035549A1 (de) | 1980-09-20 | 1980-09-20 | Verfahren zur chemischen umsetzung von cyclopentadien mit (alpha) - (beta) -ungesaettigten, organischen verbindungen nach der diels-alder-reaktion und zur gewinnung der hierbei entstehenden addukt-verbindungen |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE3035549A1 (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0860421A4 (enrdf_load_stackoverflow) * | 1995-06-22 | 1998-09-30 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3359285A (en) * | 1963-07-03 | 1967-12-19 | Mobil Oil Corp | Production of cyclic addition products |
| US3444253A (en) * | 1967-09-20 | 1969-05-13 | Union Carbide Corp | Addition reactions of butadiene catalyzed by copper (i) zeolites |
-
1980
- 1980-09-20 DE DE19803035549 patent/DE3035549A1/de active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3359285A (en) * | 1963-07-03 | 1967-12-19 | Mobil Oil Corp | Production of cyclic addition products |
| US3444253A (en) * | 1967-09-20 | 1969-05-13 | Union Carbide Corp | Addition reactions of butadiene catalyzed by copper (i) zeolites |
Non-Patent Citations (1)
| Title |
|---|
| Chem. Abstr. 90, 1979, 25 123 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0860421A4 (enrdf_load_stackoverflow) * | 1995-06-22 | 1998-09-30 |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3035549C2 (enrdf_load_stackoverflow) | 1989-02-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |