In Situ Formation Of The Organic Peracid From Carboxylic Acid And Hydrogen Peroxide Patents (Class 549/526)
  • Patent number: 10005742
    Abstract: 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: Grant
    Filed: August 11, 2015
    Date of Patent: June 26, 2018
    Assignee: NISSAN CHEMICAL INDUSTRIES, LTD.
    Inventors: Kazuki Hirasada, Yutaro Tsuda
  • Patent number: 9334252
    Abstract: 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: Grant
    Filed: October 16, 2012
    Date of Patent: May 10, 2016
    Assignee: BLUE CUBE IP LLC
    Inventors: Robert J. Wright, Kevin A. Frazier, Gyongyi Gulyas
  • Patent number: 8633327
    Abstract: 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: Grant
    Filed: March 23, 2011
    Date of Patent: January 21, 2014
    Assignee: Dow Global Technologies Inc.
    Inventors: Gyongyi Gulyas, Robert J. Wright, Martha P. Hernandez, Eric P. Ripplinger
  • Publication number: 20130267720
    Abstract: 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: Application
    Filed: December 7, 2011
    Publication date: October 10, 2013
    Applicant: DOW GLOBAL TECHNOLOGIES LLC
    Inventors: Leming Gu, William W. Fan, David Jean, Eric B. Ripplinger, Bruce D. Hook, David H. West
  • Publication number: 20130006000
    Abstract: 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: Application
    Filed: March 23, 2011
    Publication date: January 3, 2013
    Inventors: Gyongyi Gulyas, Robert J. Wright, Martha P. Hernandez, Eric P. Ripplinger
  • Patent number: 7932409
    Abstract: 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: Grant
    Filed: March 28, 2008
    Date of Patent: April 26, 2011
    Assignee: Malaysian Palm Oil Board
    Inventors: 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
  • Patent number: 7741410
    Abstract: 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: Grant
    Filed: August 28, 2006
    Date of Patent: June 22, 2010
    Assignee: BASF Aktiengesellschaft
    Inventors: Hans Peter Rath, Arno Lange, Helmut Mach, J. Richard Blackborow
  • Patent number: 7091365
    Abstract: 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: Grant
    Filed: March 8, 2004
    Date of Patent: August 15, 2006
    Assignee: ABB Lummus Global Inc.
    Inventors: Zhiping Shan, Chuen Y. Yeh, Philip J. Angevine, Frits M. Dautzenberg, Jacobus Cornelis Jansen
  • Patent number: 6740763
    Abstract: 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: Grant
    Filed: June 27, 2003
    Date of Patent: May 25, 2004
    Assignee: The C.P. Hall Company
    Inventors: James A. Nowak, Thomas A. Zillner, Leslie Patrick Mullin, III
  • Patent number: 6504040
    Abstract: 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: Grant
    Filed: June 7, 2001
    Date of Patent: January 7, 2003
    Assignee: Bayer Aktiengesellschaft
    Inventors: Peter Vogtel, Ernst-Ulrich Dorf, Gerhard Wegener, Markus Weisbeck
  • Patent number: 6448418
    Abstract: 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: Grant
    Filed: April 25, 2001
    Date of Patent: September 10, 2002
    Assignee: BASF Aktiengesellschaft
    Inventor: Christian Ott
  • Patent number: 6043383
    Abstract: 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: Grant
    Filed: April 12, 1999
    Date of Patent: March 28, 2000
    Assignee: Ube Industries, Ltd.
    Inventors: Nobuyuki Kuroda, Mitsuo Yamanaka, Osamu Yamazaki, Hirofumi Takemoto, Kohei Ninomiya, Junichi Kugimoto, Koji Kaiso, Hideo Shimomura
  • Patent number: 5599955
    Abstract: 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: Grant
    Filed: February 22, 1996
    Date of Patent: February 4, 1997
    Assignee: UOP
    Inventors: Bipin V. Vora, Peter R. Pujado
  • Patent number: 5569773
    Abstract: 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: Grant
    Filed: July 15, 1994
    Date of Patent: October 29, 1996
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Takaaki Fujiwa, Tomohisa Isobe
  • Patent number: 5510428
    Abstract: 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: Grant
    Filed: November 21, 1994
    Date of Patent: April 23, 1996
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Yoshiyuki Harano, Sozo Namai, Katsuyuki Maeda, Takaaki Murai
  • Patent number: 5420313
    Abstract: 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: Grant
    Filed: May 2, 1994
    Date of Patent: May 30, 1995
    Assignee: BP Chemicals Limited
    Inventors: Malcolm J. Cunnington, Matthew M. Miller, David C. Sherrington, Sydney Simpson, Gunnar Olason
  • Patent number: 5268489
    Abstract: 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: Grant
    Filed: February 5, 1993
    Date of Patent: December 7, 1993
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Joseph V. Koleske, John N. Argyropoulos, Oliver W. Smith
  • Patent number: 5268493
    Abstract: 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: Grant
    Filed: December 3, 1992
    Date of Patent: December 7, 1993
    Assignee: Nippon Peroxide Co., Ltd.
    Inventors: Ryuichi Kayama, Hiroshi Igarashi, Toshio Suzuki
  • Patent number: 5157131
    Abstract: Epoxides represented by the formula: ##STR1## in which A represents a methylene or oxirane group and a process for their preparation.
    Type: Grant
    Filed: October 24, 1991
    Date of Patent: October 20, 1992
    Assignee: Rhone-Poulenc Nutrition Animale
    Inventors: Pierre Chabardes, Bernard Delmond, Claude Filliatre, Michel Pereyre, Dominique Serramedan
  • Patent number: 4855465
    Abstract: 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: Grant
    Filed: March 2, 1988
    Date of Patent: August 8, 1989
    Assignee: Degussa Aktiengesellschaft
    Inventors: Andreas Grund, Guenter Prescher, Georg Boehme, Willi Hofen, Heinrich Petsch
  • Patent number: 4851556
    Abstract: 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: Grant
    Filed: March 2, 1988
    Date of Patent: July 25, 1989
    Assignee: Degussa Aktiengesellschaft
    Inventors: Rainer Siegmeier, Andreas Grund, Guenter Prescher, Udo Brandt
  • Patent number: 4849532
    Abstract: 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: Grant
    Filed: March 2, 1988
    Date of Patent: July 18, 1989
    Assignee: Degussa Aktiengesellschaft
    Inventors: Georg Boehme, Willi Hofen, Andreas Grund, Heinrich Petsch, Guenter Prescher
  • Patent number: 4590286
    Abstract: 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: Grant
    Filed: October 28, 1985
    Date of Patent: May 20, 1986
    Assignee: FMC Corporation
    Inventor: Randy A. Bull
  • Patent number: 4584390
    Abstract: 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: Grant
    Filed: May 30, 1984
    Date of Patent: April 22, 1986
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Gerhard Dieckelmann, Klemens Eckwert, Lutz Jeromin, Eberhard Peukert, Udo Steinberner
  • Patent number: 4503259
    Abstract: 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: Grant
    Filed: May 24, 1983
    Date of Patent: March 5, 1985
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Richard M. Boden, Lambert Dekker, Frederick L. Schmitt, Augustinus G. Van Loveren
  • Patent number: 4476314
    Abstract: 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: Grant
    Filed: September 7, 1982
    Date of Patent: October 9, 1984
    Assignee: Mitsubishi Gas Chemical Co., Inc.
    Inventors: Yasuhisa Kuriyama, Minoru Kakuda, Shoichi Nitoh
  • Patent number: 4423239
    Abstract: 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: Grant
    Filed: September 28, 1982
    Date of Patent: December 27, 1983
    Assignee: Nippon Petrochemicals Company, Limited
    Inventors: Kazuo Miyazaki, Hajime Hara, Kojiro Teramoto, Hideo Horii, Humiaki Oshimi, Yoshihiko Araki
  • Patent number: 4337360
    Abstract: Methylvanillyl ketone is prepared from a "through process" involving oxidation of isoeugenol followed by subsequent acidic hydrolysis.
    Type: Grant
    Filed: September 28, 1979
    Date of Patent: June 29, 1982
    Assignee: Merck & Co., Inc.
    Inventor: Meyer Sletzinger
  • Patent number: RE30945
    Abstract: 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: Grant
    Filed: February 14, 1980
    Date of Patent: May 25, 1982
    Assignees: Bayer AG, Deutsche Gold-und Silver Scheideanstalt Vormals Roessler
    Inventors: Guter Prescher, Gerd Schreyer, Otto Weiberg, Rolf Wirthwein, Helmut Waldmann, Hermann Seifert, Wulf Schwerdtel, Wolf Swodenk
  • Patent number: RE31381
    Abstract: 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: Grant
    Filed: February 14, 1980
    Date of Patent: September 13, 1983
    Assignees: Bayer Aktiengesellschaft, Deutsche Gold-und Silber-Scheideanstalt
    Inventors: Gunter Prescher, Gerd Schreyer, Otto Weiberg, Rolf Wirthwein, Helmut Waldmann, Hermann Seifert, Wulf Schwerdtel, Wolf Swodenk