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US4054611A Expired / Lapsed US ⏱️ 0.0 years remaining

Method for the preparation of p-isopropenyl phenol

Assignee: Mitsui Toatsu Chemicals Inc
•
Filing: 1974-07-30
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Granted: 1977-10-18
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Expires: 1994-07-30
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Abstract

Abstract Chemically stable p-isopropenyl phenol is produced in the form of a solution by contacting p-isopropenyl phenol, in the form of a gas or a liquid obtained immediately after condensation of said gas, with a polar solvent such as an alcohol, an ester, or an acid amide. The resultant solution of p-isopropenyl phenol can be used as the starting material for subsequent reaction to obtain useful compounds such as hydroquinone. Alternatively, p-isopropenyl phenol may be isolated in crystalline form by adding to the solution a poor solvent for the phenol such as water, or by cooling the solution.

Inventors

  • 👤 Kosuke Mimaki
  • 👤 Tsutomu Takase
  • 👤 Mitsuhiro Iwasa
  • 👤 Tomitaka Yamamori

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-28 13:08
CPC Classifications
C; C07; C07C; C07C37/00; C07C37/68; C07C37/70; C07C37/72

Claims Analysis

Total Claims: 9
Claim 1
Independent Claim 353 words
A method for the recovery of p-isopropenyl phenol in the form of a stable solution which comprises contacting p-isopropenyl phenol, in the form of a gas or of a liquid obtained immediately after condensation of said gas, said p-isopropenyl phenol gas being generated by thermal decomposition at a temperature of from 150° to 260° C. and at a pressure up to normal pressure of: a. bisphenol A in the presence of a catalytic amount of a base catalyst; or b. oligomers of p-isopropenyl phenol in the absence of catalyst or in the presence of a catalytic amount of a basic catalyst, directly with a solvent selected from the group consisting of: a monohydric alcohol expressed by the formula ROH wherein R is alkyl containing from 5 to 14 carbon atoms, cycloalkyl containing from 5 to 6 carbon atoms, or aralkyl containing from 7 to 10 carbon atoms; a dihydric alcohol or derivative thereof expressed by the formula ##STR6## wherein R 1 and R 2 are independently hydrogen or alkyl containing from 1 to 4 carbon atoms, R 3 is hydrogen, alkyl containing from 1 to 4 carbon atoms or acetyl and m is an integer of from 1 to 4; a dihydric alcohol or derivative thereof expressed by the formula HOC.sub.n H.sub.2n OR.sub.4 wherein R 4 is hydrogen, alkyl containing from 1 to 4 carbon atoms or acetyl, and n is an integer of from 3 to 6; and a trihydric alcohol or derivative thereof expressed by the formula HOC.sub.3 H.sub.5 (OR.sub.5).sub.2 wherein R 5 is hydrogen, alkyl containing from 1 to 4 carbon atoms or acetyl; an ester expressed by the formula R.sub.6 COOR.sub.7 wherein R 6 and R 7 are independently alkyl or cycloalkyl and the total number of carbon atoms in one molecule of the ester is within the range of from 6 to 20; and an acid amide expressed by the formula ##STR7## wherein R 8 , R 9 and R 9 ' are independently hydrogen or alkyl containing from 1 to 4 carbon atoms, and collecting said p-isopropenyl phenol in the form of a solution in said solvent.
Claim 2
Independent Claim 353 words
A method for the recovery of p-isopropenyl phenol in the form of a stable solution which comprises contacting p-isopropenyl phenol, in the form of a gas or of a liquid obtained immediately after condensation of said gas, said p-isopropenyl phenol gas being generated by thermal decomposition at a temperature of from 150° to 260° C. and at a pressure up to normal pressure of: a. bisphenol A in the presence of a catalytic amount of a base catalyst; or b. oligomers of p-isopropenyl phenol in the absence of catalyst or in the presence of a catalytic amount of a basic catalyst, directly with a solvent selected from the group consisting of: a monohydric alcohol expressed by the formula ROH wherein R is alkyl containing from 5 to 14 carbon atoms, cycloalkyl containing from 5 to 6 carbon atoms, or aralkyl containing from 7 to 10 carbon atoms; a dihydric alcohol or derivative thereof expressed by the formula ##STR6## wherein R 1 and R 2 are independently hydrogen or alkyl containing from 1 to 4 carbon atoms, R 3 is hydrogen, alkyl containing from 1 to 4 carbon atoms or acetyl and m is an integer of from 1 to 4; a dihydric alcohol or derivative thereof expressed by the formula HOC.sub.n H.sub.2n OR.sub.4 wherein R 4 is hydrogen, alkyl containing from 1 to 4 carbon atoms or acetyl, and n is an integer of from 3 to 6; and a trihydric alcohol or derivative thereof expressed by the formula HOC.sub.3 H.sub.5 (OR.sub.5).sub.2 wherein R 5 is hydrogen, alkyl containing from 1 to 4 carbon atoms or acetyl; an ester expressed by the formula R.sub.6 COOR.sub.7 wherein R 6 and R 7 are independently alkyl or cycloalkyl and the total number of carbon atoms in one molecule of the ester is within the range of from 6 to 20; and an acid amide expressed by the formula ##STR7## wherein R 8 , R 9 and R 9 ' are independently hydrogen or alkyl containing from 1 to 4 carbon atoms, and collecting said p-isopropenyl phenol in the form of a solution in said solvent.
Claim 3
Dependent Claim 43 words
The method according to claim 10 wherein said p-isopropenyl phenol gas is generated by thermal decomposition of bisphenol A at a temperature of from 150° to 260° C. and at a pressure up to normal pressure in the presence of a basic catalyst.
Claim 4
Dependent Claim 88 words
The method according to claim 10 wherein said p-isopropenyl phenol gas is generated by thermal decomposition of oligomers of p-isopropenyl phenol at a temperature of from 150° to 260° C. and at a pressure up to normal pressure, said oligomers having been obtained by condensation of a gas generated by thermal decomposition of bisphenol A at a temperature of from 150° to 260° C. and at a pressure up to normal pressure in the presence of a basic catalyst followed by removing phenol from the resultant condensation product.
Claim 5
Dependent Claim 72 words
The method according to claim 10 wherein said p-isopropenyl phenol gas is generated by thermal decomposition of oligomers of p-isopropenyl phenol at a temperature of from 150° to 260° C. and at a pressure up to normal pressure, said oligomers having been obtained by decomposition of hydroxyhydroperoxide having the formula ##STR8## in the presence of an acid catalyst followed by removing acetone, water and the acid catalyst from the resultant decomposition product.
Claim 6
Dependent Claim 44 words
The method according to claim 1 wherein said solvent is a polar solvent having a boiling point higher than room temperature under a reduced pressure below 200 mm Hg and above 100° C. at normal pressure and a melting point lower than 50° C.
Claim 7
Dependent Claim 20 words
The method according to claim 1 wherein said solvent is an alcohol selected from said monohydric, dihydric and polyhydric alcohols.
Claim 8
Dependent Claim 12 words
The method according to claim 1 wherein said solvent is said ester.
Claim 9
Dependent Claim 13 words
The method according to claim 1 wherein said solvent is said acid amide.

References Cited (Backward Citations)

US2736753A Cited
US3043882A Cited
US3043883A Cited
GB905994A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1980-10-17 1981-04-18 1981-10-18 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1984-10-17 1985-04-18 1985-10-18 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1988-10-17 1989-04-18 1989-10-18 $7700.00 Window Closed / Lapsed

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