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US3872173A Expired / Lapsed US ⏱️ 0.0 years remaining

Process of manufacturing para-tert-butyl-phenol

Assignee: Progil SARL
•
Filing: 1970-07-06
•
Granted: 1975-03-18
•
Expires: 1990-07-06
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Abstract

Abstract Para-tert-butyl-phenol is prepared by introducing a gaseous mixture of isomer butenes into phenol in the presence of an acidactivated clay catalyst.

Inventors

  • 👤 Jean Berthoux
  • 👤 Ghislain Schwachhofer

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-27 10:50
CPC Classifications
C; C07; C07C; C07C37/00; C07C37/11; C07C37/14; Y; Y02; Y02P; Y02P20/00; Y02P20/50; Y02P20/52

Claims Analysis

Total Claims: 11
Claim 1
Independent Claim 162 words
IN A PROCESS OF MANUFACTURING PARA-TERBUTYLPHENOL FROM PHENOL AND ISOBUTENE WHICH COMPRISES REACTING SAID ISOBUTENE WITH LIQUID PHENOL MIXED WITH AN ACID-ACTIVATED CLAY, THE IMPROVEMENT COMPRISING PROVIDING SAID ISOBUTENE IN THE FORM OF A GASEOUS MIXTURE WITH NORMAL BUTENES, AND WHEREIN THE REACTION MIXTURE CONTAINS A QUANTITY OF MOISTURE REPRESENTING 0.5 TO 5 PERCENT BY WEIGHT OF WATER WITH RESPECT TO PHENOL, THE REACTION BEING CARRIED OUT IN TWO STAGES COMPRISING (1) MAINTAINING THE LIQUID MIXTURE AT A TEMPERATURE NOT EXCEEDING 55*C. IN THE PRESENCE OF SAID ACID-ACTIVATED CLAY AND SAID WATER AND DURING FEEDING OF SAID GASEOUS MIXTURE AND (2) THEN, STOPPING THE INTRODUCTION OF SAID GASEOUS MIXTURE AT A POINT SUCH THAT AFTER THE OLEFIN INTRODUCTION STEP THE MOLAR RATIO OF FREE OR COMBINED PHENOL IN THE REACTION MASS TO FIXED ISOBUTENE IS NOT LOWER THAN 1.5, AND SUBMITTING THE REACTION MIXTURE WITHOUT INTERMEDIATE TREATMENT TO A TEMPERATURE OF ABOUT 110*C, TO ABOUT 120*C. WHILE DEHYDRATING IT BY AZEOTROPIC DISTILLATION.
Claim 2
Dependent Claim 162 words
IN A PROCESS OF MANUFACTURING PARA-TERBUTYLPHENOL FROM PHENOL AND ISOBUTENE WHICH COMPRISES REACTING SAID ISOBUTENE WITH LIQUID PHENOL MIXED WITH AN ACID-ACTIVATED CLAY, THE IMPROVEMENT COMPRISING PROVIDING SAID ISOBUTENE IN THE FORM OF A GASEOUS MIXTURE WITH NORMAL BUTENES, AND WHEREIN THE REACTION MIXTURE CONTAINS A QUANTITY OF MOISTURE REPRESENTING 0.5 TO 5 PERCENT BY WEIGHT OF WATER WITH RESPECT TO PHENOL, THE REACTION BEING CARRIED OUT IN TWO STAGES COMPRISING (1) MAINTAINING THE LIQUID MIXTURE AT A TEMPERATURE NOT EXCEEDING 55*C. IN THE PRESENCE OF SAID ACID-ACTIVATED CLAY AND SAID WATER AND DURING FEEDING OF SAID GASEOUS MIXTURE AND (2) THEN, STOPPING THE INTRODUCTION OF SAID GASEOUS MIXTURE AT A POINT SUCH THAT AFTER THE OLEFIN INTRODUCTION STEP THE MOLAR RATIO OF FREE OR COMBINED PHENOL IN THE REACTION MASS TO FIXED ISOBUTENE IS NOT LOWER THAN 1.5, AND SUBMITTING THE REACTION MIXTURE WITHOUT INTERMEDIATE TREATMENT TO A TEMPERATURE OF ABOUT 110*C, TO ABOUT 120*C. WHILE DEHYDRATING IT BY AZEOTROPIC DISTILLATION.
Claim 3
Dependent Claim 52 words
Process according to claim 1 wherein an activated clay is used, which contains 10 to 30 percent of water, with regard to its anhydrous weight and that said clay is present in a quantity of between 5 and 15 percent by weight of dry matter, with respect to the initial phenol charge.
Claim 4
Dependent Claim 23 words
Process according to claim 1 wherein gas introduction is conducted while maintaining the liquid phase at a temperature of between 40* and 50*C.
Claim 5
Dependent Claim 14 words
Process according to claim 1 wherein gas introduction is conducted at a decreasing speed.
Claim 6
Dependent Claim 13 words
Process according to claim 1 wherein the thermal treatment is made at 110*-115*C.
Claim 7
Dependent Claim 22 words
Process according to claim 1 wherein dehydration is conducted by distillation of water/phenol azeotrope under a reduced pressure of 30-40 mm. Hg.
Claim 8
Dependent Claim 25 words
Process according to claim 1 wherein an aliphatic hydrocarbon is added to the mixture and dehydration is conducted by distillation of the azeotrope water/aliphatic hydrocarbon.
Claim 9
Dependent Claim 11 words
Process according to claim 7 wherein the aliphatic hydrocarbon is hexane.
Claim 10
Dependent Claim 21 words
Process according to claim 7 wherein gas introduction is conducted while maintaining the liquid medium at a temperature lower than 40*C.
Claim 11
Dependent Claim 17 words
Process according to claim 1 wherein gaseous mixture contains at least 30 percent by weight of isobutene.

References Cited (Backward Citations)

US2732408A Cited
US2054270A Cited
US2051473A Cited
US2091565A Cited
US2140782A Cited
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US3211670A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1978-03-17 1978-09-16 1979-03-18 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1982-03-17 1982-09-16 1983-03-18 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1986-03-17 1986-09-16 1987-03-18 $7700.00 Window Closed / Lapsed

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