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US4258175A Expired / Lapsed US ⏱️ 0.0 years remaining

Process for preparing an aryl ether

Assignee: Great Lakes Chemical Corp
•
Filing: 1979-07-06
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Granted: 1981-03-24
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Expires: 1999-07-06
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Abstract

Abstract There is provided a process for preparing a compound of the formula <IMAGE> wherein X1, X2, X3, and X4 are independently selected from the group consisting of fluorine, chlorine, bromine and iodine; n is an integer of from 1 to about 100; a, b, c, and d are each integers of from about 0 to about 4; Z1 and Z2 are independently selected from the group consisting of halogen and alkyl of from about 1 to about 15 carbon atoms; R1 and R2 are independently selected from the group consisting of alkylene containing from about 1 to about 12 carbon atoms, alkylenyl containing from about 2 to about 12 carbon atoms, cycloalkylene of the formula <IMAGE> wherein R3, R4 and R5 are independently selected from the group consisting of alkylene of from about 1 to about 5 carbon atoms, and cycloalkylenyl of the formula <IMAGE> and A is selected from the group consisting of R3CR4, <IMAGE> and O; comprising the steps of: (a) reacting a halogenated diphenoxy compound of the formula <IMAGE>

Inventors

  • 👤 Sun-Mao Chen

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-03 13:27
CPC Classifications
C; C08; C08G; C08G65/00; C08G65/34; C08G65/38; C08G65/40; C08G65/4006; C08G65/48; C08K; C08K5/00; C08K5/04; C08K5/06; C08G2650/00; C08G2650/28; C08G2650/46; C08G2650/48

Claims Analysis

Total Claims: 11
Claim 1
Independent Claim 322 words
A process for preparing a compound of the formula ##STR16## wherein X 1 , X 2 , X 3 and X 4 are independently selected from the group consisting of fluorine, chlorine, bromine, and iodine; n is an integer of from 1 to about 10; a, b, c, and d are each integers of from about 1 to about 4; Z 1 and Z 2 are independently selected from the group consisting of halogen and alkyl of from about 1 to about 15 carbon atoms; R 1 and R 2 are independently selected from the group consisting of alkylene containing from about 1 to about 12 carbon atoms, alkylene containing from about2 to about 12 carbon atoms, cycloalkylene of the formula ##STR17## wherein R 3 , R 4 and R 5 are independently selected from the group consisting of alkylene of from about 1 to about 5 carbon atoms, and cycloalkylenyl of the formula ##STR18## and A is selected from the group consisting of R 3 CR 4 , ##STR19## and O; comprising the steps of: (a) reacting a halogenated diphenoxy compound of the formula ##STR20## with from about 2 to about 12 moles per mole of said halogenated diphenoxy compound of an alkylene dihalide of the formula X 1 R 1 X 2 at a temperature of from about 50 to about 200 degrees centigrade for from about 30 to about 300 minutes in the presence of an inorganic base, whereby a halogenated aryl ether is produced; and sequentially (b) reacting the halogenated aryl ether produced in step (a) with a halogenated phenol of the formula ##STR21## at a temperature of from about 50 to about 200 degrees centigrade in the presence of an inorganic base for from about 1 to about 10 hours, wherein from about 0.1 to about 2.0 moles of said halogenated phenol per mole of said halogenated diphenoxy compound are charged to the reaction mixture and reacted.
Claim 2
Dependent Claim 322 words
A process for preparing a compound of the formula ##STR16## wherein X 1 , X 2 , X 3 and X 4 are independently selected from the group consisting of fluorine, chlorine, bromine, and iodine; n is an integer of from 1 to about 10; a, b, c, and d are each integers of from about 1 to about 4; Z 1 and Z 2 are independently selected from the group consisting of halogen and alkyl of from about 1 to about 15 carbon atoms; R 1 and R 2 are independently selected from the group consisting of alkylene containing from about 1 to about 12 carbon atoms, alkylene containing from about2 to about 12 carbon atoms, cycloalkylene of the formula ##STR17## wherein R 3 , R 4 and R 5 are independently selected from the group consisting of alkylene of from about 1 to about 5 carbon atoms, and cycloalkylenyl of the formula ##STR18## and A is selected from the group consisting of R 3 CR 4 , ##STR19## and O; comprising the steps of: (a) reacting a halogenated diphenoxy compound of the formula ##STR20## with from about 2 to about 12 moles per mole of said halogenated diphenoxy compound of an alkylene dihalide of the formula X 1 R 1 X 2 at a temperature of from about 50 to about 200 degrees centigrade for from about 30 to about 300 minutes in the presence of an inorganic base, whereby a halogenated aryl ether is produced; and sequentially (b) reacting the halogenated aryl ether produced in step (a) with a halogenated phenol of the formula ##STR21## at a temperature of from about 50 to about 200 degrees centigrade in the presence of an inorganic base for from about 1 to about 10 hours, wherein from about 0.1 to about 2.0 moles of said halogenated phenol per mole of said halogenated diphenoxy compound are charged to the reaction mixture and reacted.
Claim 3
Dependent Claim 27 words
The process of claim 1, wherein n is 1 and said inorganic base is selected from the group consisting of metal carbonates, metal hydroxides, and metal oxides.
Claim 4
Dependent Claim 13 words
The process of claim 2, wherein A is R 3 CR 4 .
Claim 5
Dependent Claim 48 words
The process of claim 3, wherein R 1 and R 2 are independently selected from the group consisting of alkylene containing from about 1 to about 12 carbon atoms, and said metal is selected from the group consisting of lithium, sodium, potassium, rubidium, magnesium, calcium, strontium, and barium.
Claim 6
Dependent Claim 61 words
The process of claim 4, wherein Z 1 , Z 2 , X 1 , X 2 , X 3 , and X 4 are bromine; a, b, c, and d are from about 1 to about 4; R 1 and R 2 are alkylene of from about 1 to about 5 carbon atoms; and said metal is sodium or potassium.
Claim 7
Dependent Claim 13 words
The process of claim 5, wherein R 1 and R 2 are ethylene.
Claim 8
Dependent Claim 21 words
The process of claim 6, wherein R 3 and R 4 are methyl and said base is an alkali metal carbonate.
Claim 9
Dependent Claim 13 words
The process of claim 7, wherein a, b, c, and d are 2.
Claim 10
Dependent Claim 29 words
The process of claim 8, wherein from about 0.5 to about 2.0 moles of said halogenated phenol per mole of diphenoxy compound are reacted with said halogenated aryl ether.
Claim 11
Dependent Claim 29 words
The process of claim 9, wherein from about 1.0 to about 2.0 moles of said halogenated phenol per mole of diphenoxy compound are reacted with said halogenated aryl ether.

References Cited (Backward Citations)

US2060715A Cited
US3069386A Cited
US4136087A Cited
US4163833A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1984-03-23 1984-09-22 1985-03-24 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1988-03-23 1988-09-22 1989-03-24 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1992-03-23 1992-09-22 1993-03-24 $7700.00 Window Closed / Lapsed

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