Preparing By Catalytic Alkylation Patents (Class 568/790)
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Patent number: 4849569Abstract: Aromatic compounds are alkylated in a catalytic distillation, wherein the catalyst structure also serves as a distillation component by contacting the aromatic compound with a C.sub.2 to C.sub.10 olefin in the catalyst bed under 0.25 to 50 atmospheres of pressure and at temperatures in the range of 80.degree. C. to 500.degree. C., using as the catalyst a mole sieve characterized as acidic or an acidic cation exchange resin. For example, ethyl benzene is produced by feeding ethylene below the catalyst bed while benzene is conveniently added through the reflux in molar excess to that required to react with ethylene, thereby reacting substantially all of the ethylene and recovering benzene as the principal overhead and ethyl benzene in the bottoms.Type: GrantFiled: October 17, 1988Date of Patent: July 18, 1989Assignee: Chemical Research & Licensing CompanyInventor: Lawrence A. Smith, Jr.
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Patent number: 4739040Abstract: A method of producing surfactants from lignin is disclosed by reducing lignin in the presence of a carbon monoxide or hydrogen reducing agent at high temperature and pressure to produce low molecular weight lignin phenols and subjecting the lignin phenols to one or a combination of several reactions such as alkoxylation, alkylation, sulfonation, sulfation, alkoxysulfation, and sulfomethylation. The lignin surfactants so produced can be employed in a surfactant system to recover oil from underground formations.Type: GrantFiled: December 24, 1986Date of Patent: April 19, 1988Assignee: Texaco Inc.Inventors: Douglas G. Naae, Lawrence E. Whittington, Will A. Ledoux, Francis E. Debons
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Patent number: 4731492Abstract: A process of ortho-alkylating arylhydroxides, e.g., phenol, by passing a mixture of arylhydroxide, olefin and an inert hydrocarbon diluent in the liquid phase through a bed of activated alumina at an elevated temperature and pressure. Conversion and selectivity is improved over that obtained without the diluent.Type: GrantFiled: March 4, 1987Date of Patent: March 15, 1988Assignee: Ethyl CorporationInventors: Steven L. Wiker, S. Wendell Holmes, Jr., Dixie E. Goins
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Patent number: 4665238Abstract: Alkylaromatic compounds may be synthesized by reacting an aromatic compound with an alkylating agent comprising a mixture of gases, including carbon monoxide and hydrogen at alkylation conditions in the presence of a dual-function-catalyst. The catalyst system which is employed for this reaction will comprise (1) a composite of oxides of copper and chromium and (2) an aluminosilicate which may be either in crystalline or amorphous form.Type: GrantFiled: September 9, 1985Date of Patent: May 12, 1987Assignee: UOP Inc.Inventors: Tamotsu Imai, Paul T. Barger
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Patent number: 4599465Abstract: A process for producing an orthoalkylphenol which comprises reacting phenol with an olefin in a liquid phase in the presence of an alumina catalyst, characterized in that the water content in the liquid phase of the reaction system is maintained at a level of not higher than 250 ppm.Type: GrantFiled: June 5, 1985Date of Patent: July 8, 1986Assignee: Mitsubishi Chemical Industries, Ltd.Inventors: Akio Tamaru, Yoshiaki Izumisawa, Hidekichi Hashimoto, Kiyoji Kuma, Takashi Komaya, Masanobu Minagawa
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Patent number: 4554388Abstract: This invention relates to a process for isomerization and transalkylation of alkylphenols and for phenol-derivatives in the presence of a catalyst comprising ironoxide (s) and at least one additional oxide and in the case of 2,4,6-trimethylphenol and 2,4-dimethylphenol as alkylphenol feed, of ironoxide (s) or of a catalyst comprising ironoxide (s) and at least one additional oxide.Type: GrantFiled: February 7, 1984Date of Patent: November 19, 1985Assignee: Rheinische Braunkohlenwerke AktiengesellschaftInventors: Karl-Heinz Keim, Joachim Korff
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Patent number: 4484011Abstract: The process for preparing 4-isopropylphenol (4-IPP) from 2-isopropylphenol (2-IPP) comprising contacting phenol with 2-IPP in the presence of a catalyst system selected from: (1) the combination of sulfuric acid on comminuted acid clay and a molecular sieve; and (2) trifluoromethane sulfonic acid (TFMSA); at a temperature of from about 90.degree. C. to about 250.degree. C., preferably from about 110.degree. C. to about 200.degree. C., wherein the initial mole ratio of phenol/2-IPP is from about 6 to about 2, preferably from about 4 to about 2.5, for a sufficient period to give a mole ratio of 4-IPP/2-IPP in the reaction system of from about 0.6 to about 1.5, and preferably from about 0.8 to about 1.2, without significant meta-isopropylphenol formation, i.e., less than about 10 mole %. In the isolation procedure, distillation separates the reaction mixture into phenol, 2-IPP, and 4-IPP.Type: GrantFiled: December 2, 1983Date of Patent: November 20, 1984Assignee: Eastman Kodak CompanyInventor: Dale E. Van Sickle
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Patent number: 4451676Abstract: p-Alkenyl phenols are prepared by reacting an alkylated phenol having a replaceable hydrogen atom at the 4- position with an aliphatic aldehyde having two carbon atoms up to at least 20 carbon atoms in the molecule and a secondary amine.Type: GrantFiled: August 27, 1982Date of Patent: May 29, 1984Assignee: Ethyl CorporationInventor: Charles R. Everly
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Patent number: 4418222Abstract: A continuous process is provided for the production of para alkyl phenols. In the process a mixture of phenol, olefin and strong organic acid, is reacted for a brief period of time. The resulting reaction mixture is quenched, and the para alkyl phenol recovered.Type: GrantFiled: May 26, 1981Date of Patent: November 29, 1983Assignee: Chevron Research CompanyInventor: Lewis R. Honnen
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Patent number: 4398048Abstract: Substantially improved yields of 2,4,6-trialkylphenols result from alkylating a mixture of phenol and 2,6-dialkylphenol, the latter being a by-product of the alkylation reaction. This results flows from an unexpected synergistic effect accompanying transalkylation. The continuous method of making 2,4,6-trialkylphenol based on this property affords the highly desirable trialkylated phenols in high yield.Type: GrantFiled: October 21, 1981Date of Patent: August 9, 1983Assignee: UOP Inc.Inventor: Bruce E. Firth
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Patent number: 4391998Abstract: Phenol is catalytically alkylated with an isopropanol or propylene alkylating agent to form high yields of an isopropylphenol product enriched in the para-isomer of isopropylphenol. Such an alkylation process is carried out under catalytic alkylation conditions including a temperature of from about 200.degree. C. to 300.degree. C. and contact with a crystalline zeolite catalyst having a silica to alumina molar ratio of at least about 12 and a constraint index of about 1 to 12.Type: GrantFiled: October 21, 1981Date of Patent: July 5, 1983Assignee: Mobil Oil CorporationInventor: Margaret M. Wu
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Patent number: 4390735Abstract: A process for the preparation of a p-allylphenol of the formula I, which comprises reacting a phenol of the formula II with an allyl halide of the formula III ##STR1## in which the symbols R.sub.1 to R.sub.6 and X are as defined in the description, in the presence of a base and a phase transfer catalyst.p-Allylphenols are valuable intermediates and lubricant additives.Type: GrantFiled: October 13, 1981Date of Patent: June 28, 1983Assignee: Ciba-Geigy CorporationInventor: Siegfried Rosenberger
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Patent number: 4359591Abstract: This invention relates to a process for reacting phenol, mono- and di-alkyl phenols having at least one free o-position with methanol and/or dimethyl ether in the gas phase to form o-substituted phenols in the presence of a catalyst of oxides of iron, chromium, silicon and at least one oxide of an alkaline-earth metal, lanthanum and manganese or in the presence of a catalyst of oxides of iron, chromium, a metal from the group comprising germanium, titanium, zirconium, tin, lead, and at least one oxide of an alkali metal, alkaline-earth metal, lanthanum and manganese.Type: GrantFiled: March 30, 1981Date of Patent: November 16, 1982Assignee: Union Rheinische Braunkohlen Kraftstoff AktiengesellschaftInventors: Max Fremery, Karl-Heinz Keim, Joachim Korff
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Patent number: 4323713Abstract: Hydroquinone is subjected to an alkylation reaction utilizing isobutylene or t-butyl alcohol as the alkylating agent to obtain t-butyl hydroquinone. The alkylation reaction is effected in the presence of an acidic catalyst such as phosphoric acid at temperatures ranging from about 75.degree. to about 200.degree. C. and a pressure in the range of from about atmospheric to about 100 atmospheres. By employing a mixture of a nonpolar hydrocarbon solvent such as xylene and an aliphatic ketone such as 2-heptanone, it is possible to obtain a greater ratio of mono-alkylated product to di-alkylated product.Type: GrantFiled: November 20, 1980Date of Patent: April 6, 1982Assignee: UOP Inc.Inventor: Dusan J. Engel
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Patent number: 4322566Abstract: Amorphorus titanium, uranium, chromium ions and zirconium together with sulfate ions are effective promoters for magnesium oxide catalysts. These catalysts are active for the ortho methylation of phenols in the vapor phase to yield 2,6-xylenol.Type: GrantFiled: November 3, 1980Date of Patent: March 30, 1982Assignee: Conoco Inc.Inventor: Bruce E. Leach
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Patent number: 4316996Abstract: Detrimental color change of phenolic antioxidants during production, storage and use in rubbers is inhibited by adding during the synthesis of the phenolic antioxidant a disubstituted hydroxylamine to the catalyst neutralization solution and a substituted oxime together with a disubstituted hydroxylamine to the reaction mixture prior to filtration.Type: GrantFiled: November 17, 1980Date of Patent: February 23, 1982Assignee: The Goodyear Tire & Rubber CompanyInventors: Jacques H. Collonge, Hans Widmer
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Patent number: 4283514Abstract: Butylation of a mixture of xylenols and trimethylphenols gives a product which is suitable for use as a stabilizer for polyvinyl chloride. The material can be added to the reactor during polymerization as a shortstopper and retain effectiveness as a stabilizer in the finished polymer.Type: GrantFiled: August 22, 1979Date of Patent: August 11, 1981Assignee: Conoco, Inc.Inventors: Dean R. Weimer, Charles M. Starks
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Patent number: 4260832Abstract: There is a process disclosed for alkylating the nucleus of a phenol, said process comprising reacting an .alpha., .omega.alkanediol containing from 3 to 8 carbon atoms with a phenol having an unsubstituted nuclear position para to the phenolic hydroxyl group; said phenol being selected from the group of alkylated phenols having tertiary alkyl groups of 4 to 8 carbon atoms in both positions ortho to the phenolic hydroxyl group, in the presence of an alkali metal hydroxide or alkoxide or alkali metal at a temperature from 200.degree. to 300.degree. C. while continuously removing the water by-product as it forms and obtaining as a product said phenol having a primary hydroxy terminated alkyl group of 3 to 8 carbon atoms in said para position.Type: GrantFiled: October 29, 1979Date of Patent: April 7, 1981Assignee: The Goodyear Tire & Rubber CompanyInventors: Dane K. Parker, Richard H. Kline
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Patent number: 4259486Abstract: The present invention relates to the aminoalkylation of phenol with 4-(alkenyl)morpholines, preferably in the presence of lithium chloride. The present invention further relates to the p-(morpholinoalkyl)phenols obtained by the above method.Type: GrantFiled: February 4, 1980Date of Patent: March 31, 1981Assignee: American Cyanamid CompanyInventor: Tatao Luo
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Patent number: 4229356Abstract: A process for producing hydro-precursors for vitamin K.sub.1 and vitamin K.sub.2 which comprises reacting (A) 2-methylhydronaphthoquinone-1,4 with (B) a compound selected from the group consisting of phytyl bromide, isophytyl bromide, geranyl bromide, farnesyl bromide, geranylgeranyl bromide and the corresponding chlorides in a reaction system which comprises an aqueous phase comprising an aqueous solution of an alkali and an oily phase comprising a hydrophobic organic solvent, in the presence of a salt comprising a quaternary ammonium ion or a tetraalkyl phosphonium ion represented by the formula (I) or formula (II): ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 each represent an alkyl or aralkyl group containing from 1 to 20 carbon atoms and the sum of the carbons in R.sub.1, R.sub.2, R.sub.3 and R.sub.4 groups is at least 12. The resultant hydro-precursor is oxidized to convert it into vitamin K.sub.1 or vitamin K.sub.2.Type: GrantFiled: February 27, 1979Date of Patent: October 21, 1980Assignee: Wakunaga Yakuhin Kabushiki KaishaInventors: Iwao Tabushi, Hiroyuki Sugimoto, Akira Yazaki
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Patent number: 4092367Abstract: A process of preparing an alkylated phenol which is substantially monoalkylated and para oriented which comprises reacting phenol with a C.sub.4 -C.sub.9 olefin and wherein said olefin is utilized in about 5-10% stoichiometric excess. The broad reaction temperature utilized is about 60.degree.-105.degree. C and the time of reaction is at least 30 minutes. The catalyst utilized is anhydrous H.sub.3 PO.sub.4 which is used in a value of at least 8% based upon the weight of reactant phenol. The preferred products are p-t-amylphenol and p-t-butylphenol, and in the process of preparing these preferred phenols, the olefin may be reacted in 5-8% stoichiometric excess and the reaction temperature utilized may be 95.degree.-115.degree. C. An additional preferred product is p-nonylphenol derived from a branched propylene trimer.Type: GrantFiled: September 3, 1976Date of Patent: May 30, 1978Assignee: Nalco Chemical Co.Inventors: Billy W. Bridwell, Carl E. Johnson