CA1049040A - Dichloro-7,7 bicyclo (3.2.0) hept-2 en-6 one - Google Patents
Dichloro-7,7 bicyclo (3.2.0) hept-2 en-6 oneInfo
- Publication number
- CA1049040A CA1049040A CA75229121A CA229121A CA1049040A CA 1049040 A CA1049040 A CA 1049040A CA 75229121 A CA75229121 A CA 75229121A CA 229121 A CA229121 A CA 229121A CA 1049040 A CA1049040 A CA 1049040A
- Authority
- CA
- Canada
- Prior art keywords
- cyclopentadiene
- process according
- inert solvent
- dichloroacetyl chloride
- tertiary amine
- 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
Links
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims abstract description 60
- TVWWMKZMZALOFP-UHFFFAOYSA-N 2,2-dichloroethenone Chemical compound ClC(Cl)=C=O TVWWMKZMZALOFP-UHFFFAOYSA-N 0.000 claims abstract description 15
- FBCCMZVIWNDFMO-UHFFFAOYSA-N dichloroacetyl chloride Chemical compound ClC(Cl)C(Cl)=O FBCCMZVIWNDFMO-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000012442 inert solvent Substances 0.000 claims abstract description 12
- 239000000203 mixture Substances 0.000 claims abstract description 12
- 150000003512 tertiary amines Chemical class 0.000 claims abstract description 12
- 238000000034 method Methods 0.000 claims description 23
- 238000006243 chemical reaction Methods 0.000 claims description 17
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 4
- 238000001256 steam distillation Methods 0.000 claims description 4
- 238000011065 in-situ storage Methods 0.000 claims description 3
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 claims description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 2
- 150000001338 aliphatic hydrocarbons Chemical group 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 229940117389 dichlorobenzene Drugs 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- 239000012188 paraffin wax Substances 0.000 claims 1
- MDYOLVRUBBJPFM-UHFFFAOYSA-N tropolone Chemical compound OC1=CC=CC=CC1=O MDYOLVRUBBJPFM-UHFFFAOYSA-N 0.000 abstract description 6
- 239000000575 pesticide Substances 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- NWQWQKUXRJYXFH-UHFFFAOYSA-N 2,2-Dichloroacetaldehyde Chemical compound ClC(Cl)C=O NWQWQKUXRJYXFH-UHFFFAOYSA-N 0.000 abstract 2
- 239000000306 component Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000005292 vacuum distillation Methods 0.000 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 description 2
- IYFXXIUALYIKQR-UHFFFAOYSA-N 3-(cyclohepten-1-yl)cyclohept-2-en-1-one Chemical compound O=C1CCCCC(C=2CCCCCC=2)=C1 IYFXXIUALYIKQR-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 206010037660 Pyrexia Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000007033 dehydrochlorination reaction Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
Classifications
-
- 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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2428410A DE2428410C2 (de) | 1974-06-12 | 1974-06-12 | Verfahren zur Herstellung von 7 7-Dichlorbicyclo eckige Klammer auf 3.2.0 eckige Klammer zu hept-2-en-6-on |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1049040A true CA1049040A (fr) | 1979-02-20 |
Family
ID=5917965
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA75229121A Expired CA1049040A (fr) | 1974-06-12 | 1975-06-11 | Dichloro-7,7 bicyclo (3.2.0) hept-2 en-6 one |
Country Status (11)
| Country | Link |
|---|---|
| JP (1) | JPS518253A (fr) |
| AT (1) | AT337665B (fr) |
| BE (1) | BE830184A (fr) |
| CA (1) | CA1049040A (fr) |
| CH (1) | CH613179A5 (fr) |
| DE (1) | DE2428410C2 (fr) |
| FR (1) | FR2274594A1 (fr) |
| GB (1) | GB1452597A (fr) |
| IL (1) | IL47442A (fr) |
| IT (1) | IT1038852B (fr) |
| NL (1) | NL7506751A (fr) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3549769A (en) * | 1969-05-16 | 1970-12-22 | Ppg Industries Inc | Halogenated bicycloheptenones |
-
1974
- 1974-06-12 DE DE2428410A patent/DE2428410C2/de not_active Expired
-
1975
- 1975-06-06 NL NL7506751A patent/NL7506751A/xx not_active Application Discontinuation
- 1975-06-09 IL IL47442A patent/IL47442A/xx unknown
- 1975-06-09 CH CH741575A patent/CH613179A5/xx not_active IP Right Cessation
- 1975-06-10 AT AT439475A patent/AT337665B/de not_active IP Right Cessation
- 1975-06-10 GB GB2484775A patent/GB1452597A/en not_active Expired
- 1975-06-10 JP JP50069245A patent/JPS518253A/ja active Pending
- 1975-06-10 IT IT24217/75A patent/IT1038852B/it active
- 1975-06-11 FR FR7518222A patent/FR2274594A1/fr active Granted
- 1975-06-11 CA CA75229121A patent/CA1049040A/fr not_active Expired
- 1975-06-12 BE BE157291A patent/BE830184A/fr not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| AT337665B (de) | 1977-07-11 |
| ATA439475A (de) | 1976-11-15 |
| DE2428410A1 (de) | 1976-01-02 |
| BE830184A (fr) | 1975-12-12 |
| GB1452597A (en) | 1976-10-13 |
| JPS518253A (en) | 1976-01-23 |
| IT1038852B (it) | 1979-11-30 |
| IL47442A0 (en) | 1975-08-31 |
| CH613179A5 (en) | 1979-09-14 |
| IL47442A (en) | 1978-01-31 |
| NL7506751A (nl) | 1975-12-16 |
| FR2274594B1 (fr) | 1979-03-09 |
| FR2274594A1 (fr) | 1976-01-09 |
| DE2428410C2 (de) | 1982-08-19 |
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