In Situ Formation Of The Organic Peracid From Carboxylic Acid And Hydrogen Peroxide Patents (Class 549/526)
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Patent number: 10005742Abstract: The present invention provides a method for producing an epoxy compound by a reaction of an olefin compound with hydrogen peroxide, wherein the epoxy compound is stably and safely produced using a hydrogen peroxide stabilizer for reducing an oxygen gas generated from hydrogen peroxide. A method for producing an epoxy compound by a reaction of an olefin compound with hydrogen peroxide, wherein the reaction is carried out in the presence of an organophosphorus compound in such a reaction medium that the pH is maintained within a range of more than 7.5 and less than 12.0. The olefin compound may be 1,3,5-tris-(alkenyl)-isocyanurate. The alkenyl group in the olefin compound may be 3-butenyl group, 4-pentenyl group, 5-hexenyl group, 6-heptenyl group, or 7-octenyl group. The epoxy compound may be 1,3,5-tris-(epoxyalkyl)-isocyanurate. The reaction medium may be such a reaction medium that the pH is maintained within a range of 8.0 to 10.5.Type: GrantFiled: August 11, 2015Date of Patent: June 26, 2018Assignee: NISSAN CHEMICAL INDUSTRIES, LTD.Inventors: Kazuki Hirasada, Yutaro Tsuda
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Patent number: 9334252Abstract: A process for preparing a divinylarene dioxide including reacting (a) at least one divinylarene, (b) hydrogen peroxide, (c) at least one iron-containing catalyst, and (d) an excess of amine hydrogen halide, under conditions to form a divinylarene dioxide.Type: GrantFiled: October 16, 2012Date of Patent: May 10, 2016Assignee: BLUE CUBE IP LLCInventors: Robert J. Wright, Kevin A. Frazier, Gyongyi Gulyas
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Patent number: 8633327Abstract: A process for preparing a divinylarene dioxide including reacting (a) at least one divinylarene; and (b) at least one peracid oxidant compound, under conditions to form a divinylarene dioxide product; wherein the peracid oxidant compound is capable of providing an increased yield of a divinylarene dioxide product.Type: GrantFiled: March 23, 2011Date of Patent: January 21, 2014Assignee: Dow Global Technologies Inc.Inventors: Gyongyi Gulyas, Robert J. Wright, Martha P. Hernandez, Eric P. Ripplinger
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Publication number: 20130267720Abstract: A process for preparing a divinylarene oxide including (a) reacting (i) at least one divinylarene; (ii) at least one peroxycarboximidic acid; (iii) at least one solvent; and (iv) at least one basic compound, under reaction conditions to form a reaction of fluent containing a divinylarene oxide product; and then (b) evaporating the reaction effluent of step (a) to form a concentrate containing the divinylarene oxide product; and wherein the concentrate separates into two liquid phases.Type: ApplicationFiled: December 7, 2011Publication date: October 10, 2013Applicant: DOW GLOBAL TECHNOLOGIES LLCInventors: Leming Gu, William W. Fan, David Jean, Eric B. Ripplinger, Bruce D. Hook, David H. West
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Publication number: 20130006000Abstract: A process for preparing a divinylarene dioxide including reacting (a) at least one divinylarene; and (b) at least one peracid oxidant compound, under conditions to form a divinylarene dioxide product; wherein the peracid oxidant compound is capable of providing an increased yield of a divinylarene dioxide product.Type: ApplicationFiled: March 23, 2011Publication date: January 3, 2013Inventors: Gyongyi Gulyas, Robert J. Wright, Martha P. Hernandez, Eric P. Ripplinger
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Patent number: 7932409Abstract: A process for producing oleochemical polyols comprises the steps of epoxidizing unsaturated oil using an organic acid together with oxygenated water or a per-acid to obtain epoxidized oil; washing the epoxidized oil with salt water to remove unused organic acid together with oxygenated water or a per-acid; neutralizing acidic condition of the washed epoxidized oil with a base; washing the neutralized epoxidized oil with a salt solution until the pH of the neutralized epoxidized oil reaching 6.5 to 7.5 to removed the base residue; drying the washed neutralized epoxidized oil under vacuum; and reacting the washed neutralized dried epoxidized oil with polyhydric alcohol in the presence of boron trifluoride-diethylether complex to produce the oleochemical polyols. The oleochemical polyols are then subjected to the same washing, neutralizing, washing and drying process as in preparing the washed neutralized dried epoxidized oil.Type: GrantFiled: March 28, 2008Date of Patent: April 26, 2011Assignee: Malaysian Palm Oil BoardInventors: Hazimah Abu Hassan, Tuan Noor Maznee Tuan Ismail, Mohd Norhisham Sattar, Seng Soi Hoong, Tian Lye Ooi, Salmiah Ahmad, Kosheela Devi a/p Poo Palam, Mei Yee Cheong
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Patent number: 7741410Abstract: A process is described for epoxidizing an ethylenically unsaturated isobutene polymer, in which an organic phase comprising the isobutene polymer is contacted with an aqueous phase which comprises formic acid and hydrogen peroxide. The process affords essentially quantitative conversions after a short reaction time.Type: GrantFiled: August 28, 2006Date of Patent: June 22, 2010Assignee: BASF AktiengesellschaftInventors: Hans Peter Rath, Arno Lange, Helmut Mach, J. Richard Blackborow
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Patent number: 7091365Abstract: An integrated process combines olefin epoxidation with production of cyclohexanone and cyclohexanol for nylon. Cyclohexanone and cyclohexanol normally produced by the oxidation of cyclohexane, in which cyclohexyl hydroperoxide is generated and is removed or decomposed down stream. However, this invention utilizes the intermediate of cyclohexyl hydroperoxide as an oxidant for the olefin epoxidation and meanwhile generates a valuable product.Type: GrantFiled: March 8, 2004Date of Patent: August 15, 2006Assignee: ABB Lummus Global Inc.Inventors: Zhiping Shan, Chuen Y. Yeh, Philip J. Angevine, Frits M. Dautzenberg, Jacobus Cornelis Jansen
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Patent number: 6740763Abstract: A method of epoxidizing an unsaturated compound having a carbon-to-carbon double bond to form an oxirane ring across the double bond comprising adding to said unsaturated compound (a) an organic acid capable of being oxidized to form a peracid; (b) an oxidizing agent selected from hydrogen peroxide or acetaldehyde monoperacetate, or a combination thereof; and (c) with or without an acid catalyst selected from a mineral acid or styrene sulfonic acid, or a combination thereof to form a reactant mixture; and forming the reactant mixture in a film against a wall of a thin-film reactor that is at a temperature sufficient to form a peracid from the organic acid, and contacting the film of reactant mixture against the film reactor wall for a time sufficient for reaction of a portion of the peracid with the unsaturated compound to form an oxirane ring across a double bond of the unsaturated compound. In another embodiment, preformed peracid and unsaturated compound are added directly to the thin-film reactor.Type: GrantFiled: June 27, 2003Date of Patent: May 25, 2004Assignee: The C.P. Hall CompanyInventors: James A. Nowak, Thomas A. Zillner, Leslie Patrick Mullin, III
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Patent number: 6504040Abstract: The invention relates to an integrated process for the preparation of epoxidised olefins. In the first stage, dilute hydrogen peroxide solutions are prepared from the elements hydrogen and oxygen and are reacted in a subsequent liquid-phase epoxidation with olefin in the presence of titanium silicalite to form epoxidised olefins, and the solvents are returned to the H2O2 process again.Type: GrantFiled: June 7, 2001Date of Patent: January 7, 2003Assignee: Bayer AktiengesellschaftInventors: Peter Vogtel, Ernst-Ulrich Dorf, Gerhard Wegener, Markus Weisbeck
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Patent number: 6448418Abstract: A process is provided for the epoxidation of olefins with percarboxylic acid in a reaction mixture consisting of an aqueous phase and an organic phase, the percarboxylic acid being formed in situ in the aqueous phase from hydrogen peroxide and a carboxylic acid or a carboxylic anhydride, and the olefins being dissolved in an organic solvent in the organic phase, wherein the epoxidation is carried out in several steps, each step being carried out with a fresh aqueous phase and the aqueous phase being separated off after each step.Type: GrantFiled: April 25, 2001Date of Patent: September 10, 2002Assignee: BASF AktiengesellschaftInventor: Christian Ott
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Patent number: 6043383Abstract: 1,2-epoxy-5,9-cyclododecadiene is produced with a high selectivity thereto by epoxidizing 1,5,9-cyclododecatriene in a continuous multi-stage oxidation apparatus having a plurality of reactors connected to each other in series in such a manner that (1) in a first reactor, 1,5,9-cyclododecatriene, hydrogen peroxide, catalyst components and optionally a mineral acid are subjected to an epoxidation reaction; (2) the resultant reaction mixture delivered from the first reactor is passed through one or more succeeding reactors to further epoxidize the non-reacted 1,5,9-cyclododecatriene with the non-reacted hydrogen peroxide; and (3) the final reaction mixture produced in a rearend reactor is delivered from the oxidation apparatus, and optionally subjected to an isolation-refining procedure wherein the target 1,2-epoxy-5,9-cyclododecadiene is refined and collected and the non-reacted 1,5,9-cyclododecatriene is recovered and recycled to the epoxidation procedure.Type: GrantFiled: April 12, 1999Date of Patent: March 28, 2000Assignee: Ube Industries, Ltd.Inventors: Nobuyuki Kuroda, Mitsuo Yamanaka, Osamu Yamazaki, Hirofumi Takemoto, Kohei Ninomiya, Junichi Kugimoto, Koji Kaiso, Hideo Shimomura
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Patent number: 5599955Abstract: The present invention provides an integrated process for the production of propylene oxide from an alternate feedstream such as synthesis gas. In the process, propylene oxide is produced from a feedstream comprising hydrogen and a carbon oxide. A portion of the feedstream is passed to an oxygenate production zone to produce an oxygenate stream comprising methanol and dimethyl ether, and the oxygenate stream is passed to an olefin production zone containing a metal aluminophosphate catalyst to produce a propylene stream. The propylene stream is epoxidized with hydrogen peroxide which has been produced from hydrogen separated from a portion of the feedstream. The spent water stream produced by the epoxidation reaction is treated to remove heavy components and returned to the hydrogen peroxide production zone. The return of the unreacted propylene from the epoxidation reaction zone for its subsequent recovery and recycle permits a less complicated, lower energy propylene separation.Type: GrantFiled: February 22, 1996Date of Patent: February 4, 1997Assignee: UOPInventors: Bipin V. Vora, Peter R. Pujado
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Patent number: 5569773Abstract: The present invention provides a composition represented by the formula ##STR1## (wherein x is an integer of 3 to 7, y is an integer of 0 to 50, and R.sub.a and R.sub.b are H, methyl group, or propyl group and each of the R.sub.a and R.sub.b groups may be replaced with any of the other groups simultaneously) and useful as a raw material or modifier for resins for use in coating compositions, adhesives, epoxy resins, and the like, and further provides a process for producing a composition comprising compounds represented by the above formula (I) which process is characterized in that a compound represented by the formula ##STR2## is reacted with a lactone at 30.degree. to 20.degree. C. or compounds represented by the formula ##STR3## (wherein x, y, R.sub.a, and R.sub.b have the meanings as defined above) are epoxidized at 0.degree. to 80.degree. C. using a peroxide.Type: GrantFiled: July 15, 1994Date of Patent: October 29, 1996Assignee: Daicel Chemical Industries, Ltd.Inventors: Takaaki Fujiwa, Tomohisa Isobe
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Patent number: 5510428Abstract: Compositions (I), (II) and (III) comprising compounds having vinyl groups as side chains and epoxidized compositions (XI), (XII) and (XIII) thereof, which can be prepared by the various reaction combinations of (a) with (b) or (b)+(c), and or (d), where(a) is at least one compound having at least one vinyl group and one epoxy group in the molecule; (b) is at least one of a polybasic compound, an anhydride thereof, a polymer having carboxylic groups at terminals and a polymer having carboxylic groups as side chains; (c) is at least one organic compound having at least one active hydrogen atom; and (d) is at east one of an unsaturated monocarboxylic compound or an unsaturated monocarboxylic ester having a hydroxyl group.Type: GrantFiled: November 21, 1994Date of Patent: April 23, 1996Assignee: Daicel Chemical Industries, Ltd.Inventors: Yoshiyuki Harano, Sozo Namai, Katsuyuki Maeda, Takaaki Murai
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Patent number: 5420313Abstract: A catalyst composition having high epoxidation activity and resistant to leaching of its metal comprises molybdenum, vanadium, tungsten and/or titanium complexed to an organic or inorganic support through the intermediacy of an imidazole ligand. The catalyst may be used in epoxidation of olefinic compounds.Type: GrantFiled: May 2, 1994Date of Patent: May 30, 1995Assignee: BP Chemicals LimitedInventors: Malcolm J. Cunnington, Matthew M. Miller, David C. Sherrington, Sydney Simpson, Gunnar Olason
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Patent number: 5268489Abstract: Unsaturated cycloaliphatic esters like higher hydrocarbyl, functionally substituted or polyunsaturated cyclohex-3-ene carboxylates, made directly by cycloaddition of dienes with dienophillic (meth/eth)acrylates, and their derivatives like epoxides and urethanes, provide useful thermal and radiation curable coatings, inks, sealants, adhesives, solvents, acid scavengers, and intermediates for other uses.Type: GrantFiled: February 5, 1993Date of Patent: December 7, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Joseph V. Koleske, John N. Argyropoulos, Oliver W. Smith
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Patent number: 5268493Abstract: An .alpha.-olefin oxide is produced with an enhanced reaction selectivity by a method in which an .alpha.-olefin having 6 to 30 carbon atoms is epoxidized in an aqueous solution containing hydrogen peroxide, acetic acid, an acid catalyst, for example, sulfuric acid, and a side reaction-inhibiting agent consisting of a water-soluble neutral salt, for example, sodium sulfate, in an amount of 2 to 30% based on the total weight of the aqueous solution, by an in-situ method, while maintaining the pH of the aqueous solution at a level of 0 to 1, and the resultant reaction product is collected.Type: GrantFiled: December 3, 1992Date of Patent: December 7, 1993Assignee: Nippon Peroxide Co., Ltd.Inventors: Ryuichi Kayama, Hiroshi Igarashi, Toshio Suzuki
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Patent number: 5157131Abstract: Epoxides represented by the formula: ##STR1## in which A represents a methylene or oxirane group and a process for their preparation.Type: GrantFiled: October 24, 1991Date of Patent: October 20, 1992Assignee: Rhone-Poulenc Nutrition AnimaleInventors: Pierre Chabardes, Bernard Delmond, Claude Filliatre, Michel Pereyre, Dominique Serramedan
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Patent number: 4855465Abstract: Aliphatic epoxides of the formula: ##STR1## can be prepared in a technically efficient manner from the corresponding olefins by means of perpropionic acid in a benzene solution. The benzene solution can also be 1.5 weight percent of hydrogen peroxide, 1.5 weight percent of water and about 800 ppm of mineral acid.Type: GrantFiled: March 2, 1988Date of Patent: August 8, 1989Assignee: Degussa AktiengesellschaftInventors: Andreas Grund, Guenter Prescher, Georg Boehme, Willi Hofen, Heinrich Petsch
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Patent number: 4851556Abstract: Epoxidized polybutadienes with an average molecular weight of 500 to 100,000 and a certain content of epoxide oxygen were prepared from the corresponding polybutadienes with use of perpropionic acid in a benzene solution. The solution can also be employed in unpurified form with maximum contents of 1.5 weight percent hydrogen peroxide 1.5 weight percent of water, and about 800 ppm of mineral acid.Type: GrantFiled: March 2, 1988Date of Patent: July 25, 1989Assignee: Degussa AktiengesellschaftInventors: Rainer Siegmeier, Andreas Grund, Guenter Prescher, Udo Brandt
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Patent number: 4849532Abstract: The diepoxide of the formula: ##STR1## can be prepared from the corresponding diolefin in a technically simple manner by means of perpropionic acid in a benzene solution. The solution can also be employed in unpurified form with certain maximum contents of 1.5 weight percent of hydrogen peroxide, 1.5 weight percent of water, and of about 800 ppm of mineral acid.Type: GrantFiled: March 2, 1988Date of Patent: July 18, 1989Assignee: Degussa AktiengesellschaftInventors: Georg Boehme, Willi Hofen, Andreas Grund, Heinrich Petsch, Guenter Prescher
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Patent number: 4590286Abstract: The present invention concerns a process for epoxidizing an olefin to an oxirane by forming a monopercarboxylic acid in-situ by reacting a cyclic anhydride of a polybasic acid with hydrogen peroxide in the presence of a basic catalyst and recovering the oxirane as a distillate.Type: GrantFiled: October 28, 1985Date of Patent: May 20, 1986Assignee: FMC CorporationInventor: Randy A. Bull
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Patent number: 4584390Abstract: In a multistage process for the continuous epoxidation of double bonds of terminal and non-terminal olefins containing more than 12 carbon atoms, unsaturated higher fatty acids and their lower alkanol and lower alkanediol esters and also unsaturated fatty alcohols containing from 8 to 18, preferably 18, carbon atoms and triglycerides of higher fatty acids including unsaturated fatty acids, preferably soyabean oil, using performic acid formed in situ from hydrogen peroxide and formic acid, the reactants, olefin and hydrogen peroxide/formic acid, are passed at ambient pressure in cross-counter flow through an at least three-stage reaction cascade. The olefinic phase is introduced into the first reaction stage, the hydrogen peroxide and the formic acid are introduced in separate streams into the penultimate reaction stage and the olefin phase and the hydrogen peroxide/formic acid phase (acid water phase) are separated from one another in a phase separator after each reaction stage.Type: GrantFiled: May 30, 1984Date of Patent: April 22, 1986Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Gerhard Dieckelmann, Klemens Eckwert, Lutz Jeromin, Eberhard Peukert, Udo Steinberner
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Patent number: 4503259Abstract: Described are methods for augmenting or enhancing the aroma of perfumes and perfumed articles by adding thereto perfume aroma augmenting or enhancing quantities of novel methyl substituted-2-oxohexane derivatives produced by dimerizing isoamylene (2-methyl-2-butene) and then oxidizing the resulting product using formic acid and hydrogen peroxide; and optionally reacting the resulting product with a methyl Grignard reagent such as methyl magnesium chloride followed by hydrolysis; as well as perfume compositions, colognes and perfumed articles including solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions, hair preparations, perfumed polymers and deodorant compositions as well as bleaching compositions containing same.Also covered is the genus of compounds defined according to the structure: ##STR1## wherein R.sub.1 and R.sub.2 taken together represent oxygen; or wherein, taken separately, R.sub.1 is hydroxyl and R.sub.2 is methyl or R.sub.Type: GrantFiled: May 24, 1983Date of Patent: March 5, 1985Assignee: International Flavors & Fragrances Inc.Inventors: Richard M. Boden, Lambert Dekker, Frederick L. Schmitt, Augustinus G. Van Loveren
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Patent number: 4476314Abstract: A process for producing olefin oxides comprising epoxidizing olefins with hydrogen peroxide in the presence of an inorganic or organic antimony compound or organotin compound as a catalyst is disclosed.Type: GrantFiled: September 7, 1982Date of Patent: October 9, 1984Assignee: Mitsubishi Gas Chemical Co., Inc.Inventors: Yasuhisa Kuriyama, Minoru Kakuda, Shoichi Nitoh
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Patent number: 4423239Abstract: In a method for purifying a crude epoxidation product of a liquid conjugated diolefin polymer or a vegetable oil which comprises the steps of adding an aqueous washing agent to a crude epoxidation product which is obtained by the reaction of a liquid conjugated diolefin polymer or a vegetable oil with an organic peracid or an epoxidizing agent capable of generating an organic peracid in situ, stirring the mixture, leaving the mixture to stand to induce phase separation and thereafter withdrawing the organic layer, the improvement wherein 50 to 300 parts by weight, per 100 parts by weight of the crude epoxidation product, of a 10-80% by weight aqueous solution of isopropanol is used as the washing agent.Type: GrantFiled: September 28, 1982Date of Patent: December 27, 1983Assignee: Nippon Petrochemicals Company, LimitedInventors: Kazuo Miyazaki, Hajime Hara, Kojiro Teramoto, Hideo Horii, Humiaki Oshimi, Yoshihiko Araki
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Patent number: 4337360Abstract: Methylvanillyl ketone is prepared from a "through process" involving oxidation of isoeugenol followed by subsequent acidic hydrolysis.Type: GrantFiled: September 28, 1979Date of Patent: June 29, 1982Assignee: Merck & Co., Inc.Inventor: Meyer Sletzinger
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Patent number: RE30945Abstract: Process for continuous production of propylene oxide (FIG. 1) from propylene and aqueous hydrogen peroxide. The aqueous hydrogen peroxide is first reacted with propionic acid in the presence of acid catalyst to form perpropionic acid (1). The perpropionic acid is taken up by extraction in benzene (5, 12), and following drying of the benzene solution (16), the perpropionic acid in the solution is reacted with propylene (18) for oxidation of the propylene to propylene oxide and conversion of the perpropionic acid back to propionic acid. The reaction mixture is worked up to separate propylene oxide, propionic acid and benzene (25, 27, 31, 33), and the latter two are recycled. In the benzene extraction (5, 12), an aqueous raffinate (7) is formed containing hydrogen peroxide and acid catalyst. Water is removed from the aqueous raffinate (8) and the concentrate is recycled to the propionic acid reactor. Make-up hydrogen peroxide can be added to the aqueous raffinate before the removal of water.Type: GrantFiled: February 14, 1980Date of Patent: May 25, 1982Assignees: Bayer AG, Deutsche Gold-und Silver Scheideanstalt Vormals RoesslerInventors: Guter Prescher, Gerd Schreyer, Otto Weiberg, Rolf Wirthwein, Helmut Waldmann, Hermann Seifert, Wulf Schwerdtel, Wolf Swodenk
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Patent number: RE31381Abstract: Process for continuous production of propylene oxide (FIG. 1) from propylene and aqueous hydrogen peroxide. The aqueous hydrogen peroxide is first reacted with propionic acid in the presence of acid catalyst to form perpropionic acid (1). The perpropionic acid is taken up by extraction in benzene (5, 18) and following drying of the benzene solution (21), the perpropionic acid in the solution is reacted with propylene (24) for oxidation of the propylene to propylene oxide and conversion of the perpropionic acid back to propionic acid. The reaction mixture is worked up to separate propylene oxide, propionic acid and benzene (30, 32, 37, 39), and the latter two are recycled. In the benzene extraction (5, 18), an aqueous raffinate (7) is formed containing hydrogen peroxide and acid catalyst.Type: GrantFiled: February 14, 1980Date of Patent: September 13, 1983Assignees: Bayer Aktiengesellschaft, Deutsche Gold-und Silber-ScheideanstaltInventors: Gunter Prescher, Gerd Schreyer, Otto Weiberg, Rolf Wirthwein, Helmut Waldmann, Hermann Seifert, Wulf Schwerdtel, Wolf Swodenk