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US4886923A
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Process for the preparation of tricyclo 8.2.2.2 hexadeca 4,6,10,12,13,15 hexaene chlorinated in the benzene rings
Assignee: Montedison SpA
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Filing: 1988-09-16
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Granted: 1989-12-12
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Expires: 2008-09-16
Abstract
Abstract A process for the chlorination of the benzene rings of tricyclo 8.2.2.2 hexadeca 4,6,10,12,13,15 hexane (or (2,2)-paracyclophane) having the formula (I): ##STR1## by gaseous chlorine, by operating in the presence of at least one metal chloride as a catalyst, and at least one co-catalyst having the formula V: R--OH (V) wherein R=hydrocarbon or alkylcarboxylic radical with linear or branched chain, containing from 1 to 6 carbon atoms is taught.
Inventors
- 👤 Raffaele Ungarelli
- 👤 Maurizio A. Beretta
- 👤 Loris Sogli
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 12:55
CPC Classifications
C; C07; C07C; C07C13/00; C07C13/28; C07C13/32; C07C13/72; C07C17/00; C07C17/093; C07C17/10; C07C17/12
Claims Analysis
Total Claims: 10
Claim 1
Independent Claim
135 words
A process for preparing a chlorinated ( 2,2)-paracyclophane having formula II: ##STR5## comprise subjecting (2,2)-paracyclophane (PCP) to gaseous chlorination in a halogenated organic suspending or solvent medium and in the presence of at least one metal chloride catalyst having formula IV: Me--Clp (UV) where Me is selected from the group consisting of Fe, Sb, Al, I, Cu and Sn and p represents an integer from 1 to 5 and in the presence of at least one co-catalyst having formula R--OH, where R represents a hydrocarbyl or alkylcarboxylic radical, having a linear or a branched chain, containing from 1 to 6 C atoms, the temperature being substantially from -70° C. to 100 ° C., the pressure being substantially at an atmospheric level and the chlorine: (PCP) ratio being equal to or lower than 0.7 by weight.
Claim 2
Dependent Claim
135 words
A process for preparing a chlorinated ( 2,2)-paracyclophane having formula II: ##STR5## comprise subjecting (2,2)-paracyclophane (PCP) to gaseous chlorination in a halogenated organic suspending or solvent medium and in the presence of at least one metal chloride catalyst having formula IV: Me--Clp (UV) where Me is selected from the group consisting of Fe, Sb, Al, I, Cu and Sn and p represents an integer from 1 to 5 and in the presence of at least one co-catalyst having formula R--OH, where R represents a hydrocarbyl or alkylcarboxylic radical, having a linear or a branched chain, containing from 1 to 6 C atoms, the temperature being substantially from -70° C. to 100 ° C., the pressure being substantially at an atmospheric level and the chlorine: (PCP) ratio being equal to or lower than 0.7 by weight.
Claim 3
Dependent Claim
40 words
The process according to claim 1, wherein the reaction is carried out in a suspending medium selected from CCl 4 and CH 2 Cl 2 , at a temperature between 0° C. and +30° C. and at about atmospheric pressure.
Claim 4
Dependent Claim
32 words
The process according to claim 1, wherein the metal chloride catalyst having formula IV is prepared in situ by the action of gaseous chlorine on the metal in the reaction medium suspension
Claim 5
Dependent Claim
53 words
The process according to claim 1, wherein the molecular ratio of the metal chloride catalyst having formula IV with respect to the starting (2,2)-paracyclophane is between about 0.001 and 0.01 and the molar ratio of the co-catalyst with respect to the metal chloride catalyst having formula IV is between about 1 and 30.
Claim 6
Dependent Claim
17 words
The process according to claim 1, wherein the metal chloride catalyst having formula IV is ferric chloride.
Claim 7
Dependent Claim
27 words
The process according to claim 1, wherein the co-catalyst is selected from the class consisting of methyl alcohol, ethyl alcohol, isopropyl alcohol, acetic acid and mixtures thereof.
Claim 8
Dependent Claim
28 words
Chlorinated (2,2)-paracyclophane having formula II as defined in claim 1 that is mono-chlorinated in each of the benzene rings, when obtained by the process defined in claim 1.
Claim 9
Dependent Claim
28 words
Chlorinated (2,2)-paracyclophane having formula II as defined in claim 1 that is di-chlorinated in each of the benzene rings, when obtained by the process defined in claim 1.
Claim 10
Dependent Claim
31 words
The process according to claim 1, wherein the reaction is carried out in a chlorinated organic solvent at a temperature between 0° C. and +30° C. and at about atmospheric pressure.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1992-12-11 | 1993-06-12 | 1993-12-12 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1996-12-11 | 1997-06-12 | 1997-12-12 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2000-12-11 | 2001-06-12 | 2001-12-12 | $7700.00 | Window Closed / Lapsed |