US3711562A
Expired / Lapsed
US
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Process for preparing brominated styrene halocyclopentadiene compounds
Assignee: Hooker Chemical Corp
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Filing: 1970-06-29
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Granted: 1973-01-16
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Expires: 1990-06-29
Abstract
Abstract Compounds of the structure ARE PREPARED BY REACTING THE Diels-Alder adduct of a styrene compound and a halocyclopentadiene compound with a halogenating agent which is a mixture of chlorine and bromine in a two reactor process, wherein X is a halogen independently selected from the group consisting of fluorine, chlorine and bromine; Y is independently selected from the group consisting of alkyl of one to 10 carbon atoms, alkoxy of one to 10 carbon atoms, monohaloalkyl of one to 10 carbon atoms and halogen, wherein said halo- and halogen are independently selected from the group consisting of fluorine, chlorine and bromine; R and R'' are independently selected from the group consisting of hydrogen and lower alkyl of one to six carbon atoms; a ranges from about 3 to 4, c 0 to 1 and b is 0 to 1.
Inventors
- 👤 J Maul
- 👤 J Stevens
- 👤 R Schendel
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 14:50
CPC Classifications
C; C08; C08K; C08K5/00; C08K5/02; C08K5/03; C07; C07C; C07C17/00; C07C17/093; C07C17/10; C07C17/12; Y; Y10; Y10S; Y10S260/00; Y10S260/24
Claims Analysis
Total Claims: 25
Claim 1
Independent Claim
24 words
The process of claim 1 wherein the temperature in said first vessel is maintained within the range of about 0* to about 80* C.
Claim 2
Dependent Claim
12 words
charging a second vessel with a styrene halocyclopentadiene adduct of Formula II,
Claim 3
Dependent Claim
28 words
distilling unreacted brominating agent from said first vessel to said second vessel which is maintained at a temperature within the range of about -10* to about 150* C.,
Claim 4
Dependent Claim
18 words
The process of claim 2 wherein the temperature in said first vessel is maintained at about 25* C.
Claim 5
Dependent Claim
24 words
The process of claim 1 wherein the temperature in said second vessel is maintained within the range of about 0* to about 80* C.
Claim 6
Dependent Claim
8 words
recovering the brominated product from said first vessel,
Claim 7
Dependent Claim
16 words
introducing into said first vessel at least a portion of the mixture from said second vessel,
Claim 8
Dependent Claim
18 words
The process of claim 4 wherein the temperature in said second vessel is maintained at about 25* C.
Claim 9
Dependent Claim
27 words
The process of claim 1 wherein the brominating agent distilled from said first vessel to said second vessel comprises a mixture of bromine chloride, bromine and chlorine.
Claim 10
Dependent Claim
12 words
recharging said second vessel with a styrene halocyclopentadiene adduct of Formula II,
Claim 11
Dependent Claim
12 words
reacting the mixture in said first vessel with additional brominating agent, and
Claim 12
Dependent Claim
23 words
The process of claim 1 wherein distillation of the unreacted brominating agent is assisted by a slight nitrogen purge of said first vessel.
Claim 13
Dependent Claim
28 words
The process of claim 1 comprising passing the liquid mixture from said second vessel to said first vessel after the reaction in said first vessel has substantially ceased.
Claim 14
Dependent Claim
5 words
repeating steps 3 through 7.
Claim 15
Dependent Claim
56 words
The process of claim 1 wherein after the reaction in said first vessel has substantially ceased, the contents of said first vessel are heated to a temperature within the range of from about 100* to about 180* C. to distill a mixture comprising bromine chloride, bromine and chlorine from said first vessel to said second vessel.
Claim 16
Dependent Claim
17 words
The process of claim 1 wherein R'' is hydrogen, a is 4, b 1 and c 0.
Claim 17
Dependent Claim
17 words
The process of claim 1 wherein R'' is hydrogen, a is 3, b 1 and c 1.
Claim 18
Dependent Claim
26 words
The process of claim 1 wherEin the mixture of bromine and chlorine contains from about 1.0 to about 1.1 moles of chlorine per mol of bromine.
Claim 19
Dependent Claim
11 words
The process of claim 1 wherein X and Y are chlorine.
Claim 20
Dependent Claim
12 words
The process of claim 8 wherein R and R'' are both hydrogen.
Claim 21
Dependent Claim
9 words
The process of claim 1 wherein R is hydrogen.
Claim 22
Dependent Claim
9 words
The process of claim 1 wherein R'' is hydrogen.
Claim 23
Dependent Claim
36 words
A process of claim 1 wherein the styrene halocyclopentadiene adduct is reacted in the presence of a solvent which is selected from the group consisting of carbon tetrachloride, methylene chloride, trichloroethane, trichloromethane, acetylene tetrachloride, and hexachlorobutadiene.
Claim 24
Dependent Claim
11 words
The process of claim 17 wherein the solvent is acetylene tetrachloride.
Claim 25
Dependent Claim
15 words
The process of claim 1 wherein the halogenated styrene halocyclopentadiene adduct is recovered by crystallization.
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) | 1976-01-16 | 1976-07-17 | 1977-01-16 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1980-01-16 | 1980-07-17 | 1981-01-16 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1984-01-16 | 1984-07-17 | 1985-01-16 | $7700.00 | Window Closed / Lapsed |