Oxy Containing Aldehyde Formed Patents (Class 568/432)
  • Patent number: 9650322
    Abstract: Processes may include producing at least one alkoxyhydroxybenzaldehyde compound from at least one hydroxyphenol compound, wherein processes include the steps of: (i) synthetizing at least one alkoxyphenol from said at least one hydroxyphenol in the presence of at least one O-alkylating agent; (ii) recovering said at least one alkoxyphenol and impurities, wherein said impurities includes a dialkoxybenzene compound; (iii) separating said dialkoxybenzene from the alkoxyphenol; (iv) condensing the alkoxyphenol with glyoxylic acid and obtaining the corresponding mandelic compound; (v) oxidizing said mandelic compound to give the corresponding alkoxyhydroxy-benzaldehyde; and (vi) recovering said alkoxyhydroxybenzaldehyde.
    Type: Grant
    Filed: May 9, 2016
    Date of Patent: May 16, 2017
    Assignee: Rhodia Operations
    Inventor: Laurent Garel
  • Patent number: 9586869
    Abstract: The invention is directed to processes for treating biosolids that result in high-value, nitrogen-containing, slow-release, organically-augmented inorganic fertilizer that are competitive with less valuable or more costly conventional commercially manufactured fertilizers. The process involves conditioning traditional waste-water biosolids and processing the conditioned biosolids continuously in a high throughput manufacturing facility. The exothermic design and closed loop control of the primary reaction vessel decreases significantly the amount of power necessary to run a manufacturing facility. The process utilizes green technologies to facilitate decreased waste and enhanced air quality standards over traditional processing plants. The fertilizer produced from recovered biosolid waste is safe and meets or exceeds the United States Environment Protection Agency (USEPA) Class A and Exceptional Quality standards and is not subject to restrictions or regulations.
    Type: Grant
    Filed: April 15, 2016
    Date of Patent: March 7, 2017
    Assignee: Anuvia Plant Nutrients Corporation
    Inventors: Jeffrey C. Burnham, James P. Carr, Gary L. Dahms
  • Patent number: 9334216
    Abstract: The invention relates to a method for producing alkoxyphenol from hydroxyphenol, comprising an O-alkylation reaction of at least one hydroxyphenol into at least one alkoxyphenol, said reaction being carried out using an O-alkylating agent, an aqueous solvent containing a Bröensted base, and an organic solvent, with a base/O-alkylating agent ratio of between 0.5 and 1.5 in moles of base per mole of O-alkylating agent, an O-alkylating agent/hydroxyphenol ratio of between 0.5 and 2 moles of O-alkylating agent per mole of hydroxyphenol, and an organic solvent/hydroxyphenol ratio of less than 280 mL, preferably between 10 and 250 mL and more preferably still between 50 and 150 mL of organic solvent per mole of hydroxyphenol. The invention also relates to a method for producing at least one alkoxy-hydroxybenzaldehyde from at least one hydroxyphenol compound.
    Type: Grant
    Filed: July 12, 2013
    Date of Patent: May 10, 2016
    Assignee: Rhodia Operations
    Inventor: Laurent Garel
  • Patent number: 9328030
    Abstract: The invention is directed to processes for treating biosolids that result in high-value, nitrogen-containing, slow-release, organically-augmented inorganic fertilizer that are competitive with less valuable or more costly conventional commercially manufactured fertilizers. The process involves conditioning traditional waste-water biosolids and processing the conditioned biosolids continuously in a high throughput manufacturing facility. The exothermic design and closed loop control of the primary reaction vessel decreases significantly the amount of power necessary to run a manufacturing facility. The process utilizes green technologies to facilitate decreased waste and enhanced air quality standards over traditional processing plants. The fertilizer produced from recovered biosolid waste is safe and meets or exceeds the United States Environment Protection Agency (USEPA) Class A and Exceptional Quality standards and is not subject to restrictions or regulations.
    Type: Grant
    Filed: November 20, 2014
    Date of Patent: May 3, 2016
    Assignee: Anuvia Plant Nutrients Corporation
    Inventors: Jeffrey C. Burnham, James P. Carr, Gary L. Dahms
  • Patent number: 9006496
    Abstract: The subject of the present invention is a method for separating phenolic compounds in salified form from a reaction medium comprising them. The method of the invention for separating phenolic compounds in salified form from an aqueous reaction medium resulting from the reaction of a phenolic compound and of glyoxylic acid in the presence of a base leading to a reaction medium comprising at least the excess of initial phenolic compound in salified form and the various mandelic compounds in salified form resulting from the reaction, is characterized by the fact that said reaction medium is brought into contact with a basic anion-exchange resin that leads to the selective attachment of the initial phenolic compound to said resin and to the recovery of an aqueous stream comprising the mandelic compounds in salified form resulting from the reaction, and that the phenolic compound in salified form attached to the resin is separated by a resin regeneration treatment.
    Type: Grant
    Filed: December 6, 2013
    Date of Patent: April 14, 2015
    Assignee: Rhodia Operations
    Inventor: Magali Desouhant-Massacret
  • Patent number: 8609903
    Abstract: The present invention therefore relates to a process for preparing an aldehyde of the formula (I) where one, two or all three radicals from the group of R1, R3 and R5 are hydroxyl, and that radical or those radicals from the group of R1, R3 and R5 which are not hydroxyl are each independently hydrogen, C1-C8-alkyl or C6-C14-aryl, and R2 and R4 are each independently hydrogen, C1-C8-alkyl, C1-C8-alkoxy or C6-C14-aryl, which comprises converting an aldehyde of the formula (II) in which one, two or all three radicals from the group of R?1, R?3 and R?5 are C1-C8-alkoxy, and that radical or those radicals from the group of R?1, R?3 and R?5 which are not C1-C8-alkoxy are each independently hydrogen, C1-C8-alkyl or C6-C14-aryl, and R2 and R4 are each as defined for formula (I), at elevated temperature and elevated pressure in the presence of (C1-C4-alkyl)2-amine, and then isolating the reaction product of the formula (I).
    Type: Grant
    Filed: April 1, 2011
    Date of Patent: December 17, 2013
    Assignee: BASF SE
    Inventors: Ebel Klaus, Stefan Rüdenauer
  • Publication number: 20130316938
    Abstract: Provided is class of compounds of formula (I) wherein X, R1, R2 and R3 have the same meaning as given in the specification capable of releasing fragrant compounds in a controlled manner into the surroundings.
    Type: Application
    Filed: December 23, 2011
    Publication date: November 28, 2013
    Applicant: GIVAUDAN S.A.
    Inventors: Corinne Baumgartner, Felix Flachsmann, Philip Kraft
  • Patent number: 8431750
    Abstract: Hydroxyaromatic aldehydes are prepared by oxidation of a corresponding mandelic derivative carried out in a basic medium and in the presence of a catalytic system containing at least two metal elements.
    Type: Grant
    Filed: June 3, 2008
    Date of Patent: April 30, 2013
    Assignee: Rhodia Operations
    Inventors: Christian Maliverney, Jean-Christophe Bigouraux, Laurent Garel
  • Publication number: 20120232279
    Abstract: The invention concerns processes for oxidizing an alcohol to produce a carbonyl compound. The processes comprise contacting the alcohol with (i) a gaseous mixture comprising oxygen; and (ii) an amine compound in the presence of a catalyst, having the formula: where each of R1-R12 are independently H, alkyl, aryl, CF3, halogen, OR13, SO3R14, C(O)R15, CONR16R17 or CO2R18; each of R13-R18 is independently alkyl or aryl; and Z is alkl or aryl.
    Type: Application
    Filed: March 8, 2012
    Publication date: September 13, 2012
    Applicant: LOS ALAMOS NATIONAL SECURITY, LLC
    Inventors: Susan Kloek Hanson, Louis A. Silks, Ruilian Wu
  • Publication number: 20120220792
    Abstract: Provided is a process for producing aldehydes or ketones by oxidizing alcohols with oxygen, which comprises oxidizing alcohols to aldehydes or ketones in an organic solvent at room temperature with oxygen or air as an oxidant, wherein ferric nitrate (Fe(NO3)3.9H2O), 2,2,6,6-tetramethylpiperidine N-oxyl (TEMPO) and an inorganic chloride are used as catalysts, the reaction time is 1-24 hours, and the molar ratio of said alcohols, 2,2,6,6-tetramethylpiperidine N-oxyl and the inorganic chloride is 100:1˜10:1˜10:1˜10. The present process has the advantages of high yield, mild reaction conditions, simple operation, convenient separation and purification, recoverable solvents, substrates used therefor being various and no pollution, and therefore it is adaptable to industrialization.
    Type: Application
    Filed: July 30, 2010
    Publication date: August 30, 2012
    Inventors: Shengming Ma, Jinxian Liu, Jinqiang Kuang, Yu Liu, Yuli Wang, Qiong Yu, Weiming Yuan, Suhua Li, Bo Chen, Jiajia Cheng, Baoqiang Wan, Juntao Ye, Shichao Yu
  • Publication number: 20110306802
    Abstract: Hydroxyaromatic aldehydes are prepared by oxidation of a corresponding mandelic derivative carried out in a basic medium and in the presence of a catalytic system containing at least two metal elements.
    Type: Application
    Filed: June 3, 2008
    Publication date: December 15, 2011
    Inventors: Christian Maliverney, Jean-Christophe Bigouraux, Laurent Garel
  • Patent number: 7538253
    Abstract: The present invention relates to a novel method for preparing a catalyst of the formula (1), WOx wherein, W represents tungsten atom, O represents oxygen atom x represents a value determined by oxidative state of W, for partial oxidation of methylbenzenes, the method comprising: (a) a step of preparing tungsten oxide slurry by wet milling; (b) a step of supporting the slurry obtained in the step (a) on fire-resistance inorganic carrier by impregnation; (c) a step of drying the catalyst obtained in the step (b); and (d) a step of calcining the dried catalyst obtained in the step (c), and can reduce the reaction temperature on the basis of equivalent yield in the preparation of corresponding aromatic aldehyde from methylbenzenes since the catalyst has increased the surface areas compared to the conventional one, and thus has high conversion rate.
    Type: Grant
    Filed: November 21, 2006
    Date of Patent: May 26, 2009
    Assignee: LG Chem Ltd.
    Inventors: Won Ho Lee, Dong Il Lee, Jong Hyun Chae, Hyun Kyung Yoon
  • Patent number: 7417171
    Abstract: The present invention relates to a method for preparing an aromatic dialdehyde, comprising, a) a step of gas phase oxidation reaction for preparing aromatic dialdehyde from dimethyl benzene; b) a step of separation for selectively recovering crude aromatic dialdehyde of molten phase from the reaction product of the step (a); and c) a step of purification for obtaining highly pure aromatic dialdehyde by purifying said crude aromatic dialdehyde, and a manufacturing system used for the preparation method. The method for preparation of the aromatic dialdehyde according to the present invention is simple, effective, and advantageous in that highly pure aromatic dialdehyde can be continuously prepared.
    Type: Grant
    Filed: December 13, 2006
    Date of Patent: August 26, 2008
    Assignee: LG Chem, Ltd.
    Inventors: Jong Hyun Chae, Won Ho Lee, Dong Il Lee, In Kyu Park, Yong Jin Choe, Sung Kyu Lee, Yeong Dae Kim, Jong Suh Park, Seong Hoon Kang
  • Patent number: 7402709
    Abstract: A new high-yield, easily industrialized process for synthesizing compounds of formula (IV), in which X1 and X2, the same or different, are linear or branched C1-C8 alkyls, n and m are 0, 1 or 2, with the proviso that n and m are not simultaneously 0; or (OX1)n and (OX2)m taken together form an O-T-O group where T is chosen from —CH2—, —CH2CH2, —CH2CH2CH2—, —C(CH3)2—. The process comprises treating a chloromethyl derivative (I) with an alkaline acetate to form the intermediate acetylderivative (II); the intermediate (II) is to hydrolysed to form the alcohol (III); the alcohol (III) is then oxidised in the presence of air and catalysts to obtain the desired derivative (IV). The process runs its course within a short period of time, with high yields and high selectivity; in addition, the process does not require purification and separation of the intermediates and can therefore be favourably conducted in a single batch.
    Type: Grant
    Filed: October 28, 2004
    Date of Patent: July 22, 2008
    Assignee: Endura S.p.A.
    Inventors: Valerio Borzatta, Elisa Capparella, Carlotta Gobbi, Elisa Poluzzi
  • Patent number: 7094925
    Abstract: A process for the oxidation of an alkyl-aromatic compound, wherein the aromatic compound is admixed with an oxidising agent or sulfur compound in the presence of an ionic liquid is described. In this process, air, dioxygen, peroxide, superoxide, any other form of active oxygen, nitrite, nitrate, nitric acid or other oxides (or oxyhalides) of nitrogen (hydrate or anhydrous) are preferably used as the oxidising agent. The process is usually under Bronsted acidic conditions. The product of the oxidation reaction is preferably a carboxylic acid or ketone or an intermediate compound in the oxidation such as an aldehyde, or alcohol. The oxidation is preferably performed in an ionic liquid containing an acid promoter such as methanesulfonic acid.
    Type: Grant
    Filed: October 5, 2001
    Date of Patent: August 22, 2006
    Assignee: The Queen's University of Belfast
    Inventors: Martyn John Earle, Suhas Prabhakar Katdare
  • Patent number: 6797844
    Abstract: A process for producing a phthalaldehyde which comprises reacting at least one compound selected between o-xylylene glycol and o-xylylene oxide with nitric acid. The nitric acid is used in an amount of about 0.2 to 20 mol per mol of the compound selected between o-xylylene glycol and o-xylylene oxide. The process enables a phthalaldehyde to be efficiently produced from easily available materials.
    Type: Grant
    Filed: June 11, 2003
    Date of Patent: September 28, 2004
    Assignee: Daicel Chemical Industries, Ltd.
    Inventor: Tohru Nakai
  • Patent number: 6608229
    Abstract: A simplified process for oxidizing starch and other polysaccharides in an aqueous solution or suspension using hypochlorite in the presence of a catalytic amount of a nitroxyl compound is described. The oxidation is process is bromide-free and is carried out at a pH between 7 and 8.3 and at a temperature between 15 and 25° C.
    Type: Grant
    Filed: April 25, 2001
    Date of Patent: August 19, 2003
    Assignee: SCA Hygiene Products Zeist B.V.
    Inventors: Petter Bragd, Arie Cornelis Besemer, Jeffrey Wilson Thornton
  • Patent number: 6518419
    Abstract: Primary alcohols, especially in carbohydrates, can be selectively oxidized to aldehydes and carboxylic acids in a low-halogen process by using a peracid in the presence of a catalytic amount of a di-tertiary-alkyl nitroxyl (TEMPO) and a catalytic amount of halide. The halide is preferably bromide and the process can be carried out at nearly neutral to moderately alkaline pH (5-11). The peracid can be produced or regenerated by means of hydrogen peroxide or oxygen. The process is advantageous for producing uronic acids and for introducing aldehyde groups which are suitable for crosslinking and derivatization.
    Type: Grant
    Filed: November 7, 2000
    Date of Patent: February 11, 2003
    Assignee: Nederlandse Organisatie voor Toegepast-Natuurwetenschappelijk Onderzoek TNO
    Inventors: Jan Pieter Van Der Lugt, Jan Matthijs Jetten, Arie Cornelis Besemer, Hendrik Arend Van Doren
  • Patent number: 6495726
    Abstract: The present invention relates to an improved process for the production of benzaldehyde with 40-50% selectivity comprising by catalytic liquid phase air oxidation of toluene. The process involves providing a continuous flow of air in the presence of a catalyst such as salts of Fe, Co, Mo and Ni, and preferably a co-catalyst such as salts of manganese or copper, a promoter which may also be a bromine source, and a carboxylic acid solvent selected from the group consisting of acetic, propionic, benzoic acids ranging between 0.05 to 0.3 wt. times with respect to toluene, at a temperature ranging between 60-130° C. and pressures in the range of 1-10 bars for a period of 0.5-1.5 hours to obtain benzaldehyde (40-50%) along with other by-products.
    Type: Grant
    Filed: October 7, 1999
    Date of Patent: December 17, 2002
    Assignee: Council of Scientific and Industrial Research
    Inventors: Mannepalli Lakshmi Kantam, Boyapati Manoranjan Choudary, Pentlavally Sreekanth, Kottapalli Koteswara Rao, Kantarao Naik, Thella Prathap Kumar, Asad Ali Khan
  • Patent number: 6458737
    Abstract: The present invention has for its object to provide a novel catalyst by use of which methylbenzenes can be oxidized in gaseous phase in the presence of molecular oxygen to give the corresponding aromatic aldehydes in high yields, a process for producing an aromatic aldehyde from the corresponding methylbenzene in a high yield by use of said catalyst, and a process for producing cyclohexanedimethanol which comprises hydrogenating phthalaldehyde among the aromatic aldehydes which can be obtained as above.
    Type: Grant
    Filed: November 13, 2000
    Date of Patent: October 1, 2002
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Nobuji Kishimoto, Isao Nakamura, Yusei Nagamura, Akiyoshi Nakajima, Masashi Hashimoto, Kunika Takahashi
  • Patent number: 6399838
    Abstract: A process for preparing 2,6-dimethylphenol from 2,4,6-trimethylphenol is provided. The process includes two steps: (1) selective oxidation of 2,4,6-trimethylphenol to 3,5-dimethyl-4-hydroxybenzaldehyde and (2) deformylation of the resulting benzaldehyde to 2,6-dimethylphenol. In step (1), the 2,4,6-trimethylphenol is reacted with oxygen-containing gases at temperatures of 20 to 200° C. in the presence of an iron-containing catalyst, which has higher 3,5-dimethyl-4-hydroxybenzaldehyde selectivity than the known copper-based catalysts. In step (2), a copper-containing catalyst is used to replace the customarily used precious metal catalysts for the effective deformylation of the 3,5-dimethyl-4-hydroxybenzaldehyde to 2,6-dimethylphenol.
    Type: Grant
    Filed: February 2, 2001
    Date of Patent: June 4, 2002
    Assignee: National Science Council
    Inventors: Kuo-Tseng Li, Pang Yih Liu
  • Patent number: 6245936
    Abstract: The present invention concerns a process for the preparation of a 2-hydroxybenzoic acid and of a 4-hydroxybenzaldehyde and derivatives thereof from a mixture of two phenolic compounds, one carrying a formyl or hydroxymethyl group in the 2 position, and the other carrying a formyl or hydroxymethyl group in the 4 position. The invention also concerns the preparation of a 4-hydroxybenzaldehyde from said mixture. The invention more particularly concerns the preparation of 3-methoxy-4-hydroxybenzaldehyde and of 3-ethoxy4-hydroxybenzaldehyde, respectively known as “vanillin” and ethylvanillin”.
    Type: Grant
    Filed: April 12, 1999
    Date of Patent: June 12, 2001
    Assignee: Rhodia Chimie
    Inventors: Pascal Metivier, Christian Maliverney, Philippe Denis
  • Patent number: 6184421
    Abstract: The present invention concerns a process for the preparation of a 4-hydroxybenzaldehyde and its derivatives. More particularly, the invention concerns the preparation of 3-methoxy-4-hydroxybenzaldehyde and 3-ethoxy-4-hydroxybenzaldehyde, respectively known as vanillin and ethylvanillin.
    Type: Grant
    Filed: May 13, 1999
    Date of Patent: February 6, 2001
    Assignee: Rhodia Chimie
    Inventor: Pascal Metivier
  • Patent number: 5877330
    Abstract: Vanadium-containing catalysts are obtained by using polyvanadic acid as a source of vanadium. Vanadium-containing catalysts are obtained by mixing catalyst components other than vanadium, or their precursors, with a polyvanadic acid sol which is formed by ion-exchanging a metavanadic acid aqueous solution with a proton-type cation-exchange resin and performing polycondensation, and by drying and/or calcining the mixture.
    Type: Grant
    Filed: January 29, 1997
    Date of Patent: March 2, 1999
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Nobuji Kishimoto, Etsushige Matsunami
  • Patent number: 5877355
    Abstract: Process for making an alkyl-substituted salicylaldehyde wherein the alkyl substitution amounts to at least 8 alkyl carbon atoms per molecule, and preferably not more than 25, comprising ozonolizing an alkyl-substituted 2-hydroxy beta-methylstyrene wherein said alkyl substitution amounts to at least 8 carbon atoms per molecule. Upon oximation of the products, useful metal extractants are produced, particularly for the extraction of copper.
    Type: Grant
    Filed: August 15, 1997
    Date of Patent: March 2, 1999
    Assignee: Henkel Corporation
    Inventor: Leroy Krbechek
  • Patent number: 5861286
    Abstract: The present invention relates to a process for the preparation of aromatic substances having formula (I), characterized in that a substrate having formula (II) is subjected to an oxydation in the presence of at least one protein and at least one metal ion, formula wherein R.sub.1 may be a radical --H, --CH.sub.3, --CH.sub.2 OH, --CHO, --COOH, --OCH.sub.3, or --COO--CH(COOH)--CH.sub.2 --C.sub.6 H.sub.3 (OH).sub.2 ; R.sub.2 may be a radical --H, --OH, or --OCH.sub.3 ; R.sub.3 may be a radical --H, --OH, --OCH.sub.3, or O-glucosid; R.sub.4 may be a radical --H, --OH, or --OCH.sub.3.
    Type: Grant
    Filed: September 25, 1997
    Date of Patent: January 19, 1999
    Assignee: V. Mane Fils
    Inventors: Jean Mane, Joseph Zucca
  • Patent number: 5856583
    Abstract: A method for the preparation of 2-hydroxyarylaldehydes from an aryloxy magnesium compound and formaldehyde, which comprises reacting at a temperature from 40.degree.-120.degree. C., an aryloxy magnesium compound having an aryloxy anion and a non-aryloxy anion and in which (a) the non-aryloxy anion is more basic than the aryloxy anion such that when the aryloxy magnesium compound is brought into contact with an acidic species, the acid reacts more preferentially with the non-aryloxy anion to form an aryloxy magnesium salt and (b) the aryloxy anion has at least one free position ortho to the hydroxyl group in the aryloxy anion, with formaldehyde or a compound capable of giving rise to formaldehyde under the reaction conditions in the presence of a polar co-solvent capable of providing the non-aryloxy anion in the aryloxy magnesium compound characterized in that the non-aryloxy anion is selected from the group consisting of an oxide, a hydroxide, a carboxylate, a sulphate and a nitrate.
    Type: Grant
    Filed: May 21, 1997
    Date of Patent: January 5, 1999
    Assignee: Allco Chemical Corp.
    Inventors: Jeffrey Howard Dimmit, Mark Alan Kearns, William H. Chambless
  • Patent number: 5811559
    Abstract: Hydroxybenzaldehydes, for example salicylaldehyde, are prepared in high yields by oxidizing the corresponding hydroxybenzyl alcohols, e.g., saligenol, with molecular oxygen or an oxygen-containing gas, in liquid phase, in an aqueous reaction medium containing an alkali, in the presence of (i) a catalytically effective amount of a platinum catalyst and (ii) a cocatalytically effective amount of boron and bismuth compounds.
    Type: Grant
    Filed: November 18, 1997
    Date of Patent: September 22, 1998
    Assignee: Rhone-Poulenc Chimie
    Inventor: Helene LeFranc
  • Patent number: 5811587
    Abstract: The present invention concerns a process for the hydroxyalkylation of a carbocyclic aromatic ether.The invention preferably relates to the preparation of 3-methoxy-4-hydroxybenzyl alcohol by the hydroxymethylation of guaiacol.It also concerns the oxidation of the hydroxyalkylated ethers obtained, in particular the oxidation of 3-methoxy-4-hydroxybenzyl alcohol to 3-methoxy-4-hydroxybenzaldehyde, commonly known as "vanillin".The process for the hydroxyalkylation of a carbocyclic aromatic ether of the invention consists of reacting the aromatic ether with a carbonyl compound in the presence of a catalyst and is characterized in that the hydroxyalkylation reaction is carried out in the presence of an effective quantity of a zeolite.
    Type: Grant
    Filed: January 23, 1997
    Date of Patent: September 22, 1998
    Assignee: Rhone-Poulenc Chimie
    Inventors: Claude Moreau, Sylvie Razigade-Trousselier, Annie Finiels, Francois Fajula, Laurent Gilbert
  • Patent number: 5783737
    Abstract: The present invention concerns a process for the preparation of 3-carboxy-4-hydroxybenzaldehydes and derivatives thereof from phenolic compounds carrying formyl and/or hydroxymethyl groups in the 2 and 4 positions.The invention also concerns the preparation of 4-hydroxybenzaldehydes from 3-carboxy-4-hydroxybenzaldehydes.More particularly, the invention concerns the preparation of 3-methoxy-4-hydroxybenzaldehyde and 3-ethoxy-4-hydroxybenzaldehyde, respectively known as "vanillin" and "ethylvanillin".The process for the preparation of 3-carboxy-4-hydroxybenzaldehyde is characterized in that the group in the 2 position in a phenolic compound carrying formyl and/or hydroxymethyl groups in the 2 and 4 positions is selectively oxidized to a carboxy group, and optionally a hydroxymethyl group in the 4 position is selectively oxidized to a formyl group.A successive decarboxylation step for a 3-carboxy-4-hydroxybenzaldehyde produces a 4-hydroxybenzaldehyde.
    Type: Grant
    Filed: January 24, 1997
    Date of Patent: July 21, 1998
    Assignee: Rhone-Poulenc Chimie
    Inventor: Pascal Metivier
  • Patent number: 5773664
    Abstract: A process for separating off poorly soluble by-products from reaction mixtures which are produced in the oxidation of p-cresol with oxygen or an oxygen-containing gas in methanol as solvent in the presence of alkali metal hydroxide and in the presence of metal compounds as catalyst, is characterized in that, after the oxidation, excess alkali is neutralized to the extent that a salt precipitate forms and this salt precipitate is separated off together with the poorly soluble by-products.
    Type: Grant
    Filed: January 26, 1996
    Date of Patent: June 30, 1998
    Assignee: Bayer Aktiengesellschaft
    Inventors: Albert Schnatterer, Helmut Fiege, Frank Jelitto, Peter Skornia, Karl-Heinz Theisen
  • Patent number: 5693869
    Abstract: This invention relates to an improved process for the single step oxidation of 3-phenoxytoluene to 3-phenoxybenzaldehyde using molecular oxygen as the oxidant by employing a Ti.sub.2 VMoP.sub.6 O.sub.24 catalyst having particular infrared spectral bands.
    Type: Grant
    Filed: December 9, 1994
    Date of Patent: December 2, 1997
    Assignee: Council of Scientific & Industrial Research
    Inventors: Joseph Kuruvilla, Changaramponnath Gopinathan, Sarada Gopinathan, Paul Ratnasamy
  • Patent number: 5689009
    Abstract: Hydroxybenzaldehydes, for example salicylaldehyde, are prepared in high yields by oxidizing the corresponding hydroxybenzyl alcohols, e.g., saligenol, with molecular oxygen or an oxygen-containing gas, in liquid phase, in an aqueous reaction medium containing an alkali, in the presence of (i) a catalytically effective amount of a platinum catalyst and (ii) a cocatalytically effective amount of boron and bismuth compounds.
    Type: Grant
    Filed: February 13, 1995
    Date of Patent: November 18, 1997
    Assignee: Rhone-Poulenc Chimie
    Inventor: Helene Lefranc
  • Patent number: 5475156
    Abstract: A method is provided for converting a 2,4,6-trialkylphenol, such as mesitol, to a dialkylphenol, for example 2,6-dimethylphenol, by effecting the selective oxidation of the 2,4,6-trialkylphenol, followed by the deformylation of the resulting 3, 5-dialkyl-4-hydroxybenzaldehyde.
    Type: Grant
    Filed: June 6, 1994
    Date of Patent: December 12, 1995
    Assignee: General Electric Company
    Inventors: Andrew J. Caruso, Julia L. Lee
  • Patent number: 5354920
    Abstract: A method for the preparation of a 2-hydroxyarylaldehyde which comprises reacting an aryloxymagnesium halide derived from a phenol having at least one free ortho position relative to the phenolic hydroxy group with formaldehyde or a formaldehyde-liberating compound under substantially anhydrous conditions in the presence of a polar organic solvent other than hexamethylphosphoramide or 1,3-dimethyl-3,4,5,6-2(1H)-pyrimidone.
    Type: Grant
    Filed: August 10, 1993
    Date of Patent: October 11, 1994
    Assignee: Zeneca Limited
    Inventors: Brian G. Cox, Daniel Levin
  • Patent number: 5354919
    Abstract: Aromatic compounds bearing oxidizable alkyl substituents, e.g., alkoxylated and/or hydroxylated such substrates, notably the phenolics/cresols, are selectively oxidized, e.g., into hydroxybenzaldehydes, by reacting same with appropriate oxidizing agents, in an aqueous reaction medium, in the presence of a catalytically effective amount of a solid, palladium-containing oxidation catalyst (optionally containing a cocatalytically effective amount of tin, germanium, tellurium and/or copper).
    Type: Grant
    Filed: June 29, 1993
    Date of Patent: October 11, 1994
    Assignee: Rhone-Poulenc Chimie
    Inventors: Michel Costantini, Dominique Laucher, Eric Fache
  • Patent number: 5304685
    Abstract: A process for preparing 3-(hydroxyphenyl)propionaldehydes of the formula I ##STR1## and, where appropriate, for preparing 3-(hydroxyphenyl)propanols of the formula II ##STR2## where R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are each hydrogen, C.sub.1 -C.sub.20 -alkyl, C.sub.3 -C.sub.20 -cycloalkyl, C.sub.4 -C.sub.20 -alkylcycloalkyl, C.sub.4 -C.sub.20 -cycloalkylalkyl or C.sub.5 -C.sub.20 -alkylcycloalkylalkyl,R.sup.3 and R.sup.4 are each aryl, C.sub.7 -C.sub.20 -aralkyl, heterocycloalkyl or C.sub.3 -C.sub.20 -heterocycloalkylalkyl, entailsa) reacting phenols of the formula III ##STR3## where R.sup.1 and R.sup.2 have the abovementioned meanings, with 3-hydroxypropionaldehydes of the formula IV ##STR4## where R.sup.3 and R.sup.4 have the abovementioned meanings, in the presence of a basic catalyst at from 90.degree. to 230.degree. C. and under from 0.01 to 50 bar and, where appropriate,b) treating the resulting 3-(hydroxyphenyl)propionaldehydes of the formula I ##STR5## where R.sup.1, R.sup.2, R.sup.3 and R.sup.
    Type: Grant
    Filed: March 26, 1993
    Date of Patent: April 19, 1994
    Assignee: BASF Aktiengesellschaft
    Inventors: Franz Merger, Martin Schmidt-Radde
  • Patent number: 5248816
    Abstract: A method for the preparation of a 2-hydroxymandelic acid of the formula ##STR1## wherein R represents an alkyl radical containing from 7 to 12 carbon atoms which comprises reacting glyoxylic acid with a phenol of the formula: ##STR2## under acid conditions. Oxidation of the 2-hydroxymandelic acid to the corresponding 2-hydroxybenzaldehyde is also described.
    Type: Grant
    Filed: October 8, 1992
    Date of Patent: September 28, 1993
    Assignee: Imperial Chemical Industries PLC
    Inventors: Ralph Shuttleworth, Jan M. Fielden, Daniel Levin
  • Patent number: 5136104
    Abstract: From a methoxy-, tertiary butyl-, or phenoxy-substituted toluene, a corresponding substituted benzaldehyde is obtained by the catalytic gas-phase oxidation of the substituted toluene with a molecular oxygen-containing gas in the presence of a catalyst composition represented by the formula, V.sub.a X.sub.b Y.sub.c O.sub.d, wherein X stands for at least one element from among Na, K, Rb, Cs, and Tl (with the exception of a case wherein K is used alone), Y for at least one element from among Mg, Ca, Sr, Ba, Nb, Ta, P, Sb, Bi, Cu, Ag, Ti, Fe, Co, Ni, Sn, Ce, and Zn, and a, b, c, and d jointly represent an atomic ratio of the relevant elements.
    Type: Grant
    Filed: January 12, 1987
    Date of Patent: August 4, 1992
    Assignee: Nippon Shokubai Kagaku Kogyo Co. Ltd.
    Inventors: Noboru Saito, Isao Nakamura, Michio Ueshima, Kazuhiro Takatsu, Isao Nagai
  • Patent number: 5130493
    Abstract: o-Hydroxy-benzaldehydes can be obtained by oxidation of the o-cresols, on which they are based, with oxygen in the presence of substances having a base reaction in a solvent if chelate complexes of iron, manganese or a mixuture of both with polyaza-macrocycles as chelating agents are employed as catalysts. Copper or a copper compound is advantageously added as a co-catalyst.
    Type: Grant
    Filed: April 5, 1991
    Date of Patent: July 14, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Albert Schnatterer, Helmut Fiege, Karl-Heinz Neumann
  • Patent number: 4978802
    Abstract: Aromatic aldehydes are produced by oxidation with oxygen of a para-cresol derivative in a solvent, in the presence of a base and a catalytic amount of a cobalt compound. The catalyst is a chelated complex of cobalt with a rigid structure that is slightly oxidizable selected from the group consisting of bis-(4-methylpyridine isoindolinato)cobalt(II) acetate, phthalocyaninatocobalt(II), and sulfophthalocyaninanatocobalt(II). The process is particularly suited to the production of p-hydroxy benzaldehydes.
    Type: Grant
    Filed: December 20, 1988
    Date of Patent: December 18, 1990
    Assignee: L'Air Liquide, Societe Anonyme pour l'Etude et l'Exploitation des Procedes Georges Claude
    Inventors: Philippe Campo, Panayotis Cocolios, Paul Dognin, Henry Ledon
  • Patent number: 4929766
    Abstract: p-Hydroxy-benzaldehydes can be obtained by oxidation of the corresponding p-cresols with oxygen in the presence of basic substances in a solvent, the reaction being carried out in the additional presence of a chelate complex of iron and/or manganese. If desired, the reaction can be carried out in the presence of further metal salts.
    Type: Grant
    Filed: February 16, 1989
    Date of Patent: May 29, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventors: Albert Schnatterer, Helmut Fiege
  • Patent number: 4915875
    Abstract: Paramethyl-substituted hindered phenols are selectively oxidized by contacting with an oxidizing agent at elevated temperatures in the presence of a heterogeneous oxidative coupling catalyst. In the absence of an optional nucleophile the products comprise carbon-carbon oxidative coupling products. In the presence of a nucleophile, addition products result that may be further oxidized by continued exposure to the oxidizing agent to yield substituted p-hydroxybenzaldehydes.
    Type: Grant
    Filed: November 4, 1986
    Date of Patent: April 10, 1990
    Assignee: The Dow Chemical Company
    Inventors: Timothy R. Diephouse, Robert M. Strom
  • Patent number: 4814512
    Abstract: A method for the production of p-methoxybenzaldehyde by the vapor-phase catalytic oxidation of p-methoxytoluene, which method comprises cooling and condensing a mixed gas formed by said reaction of oxidation thereby preparing a solution containing p-methoxybenzaldehyde, treating said solution in the presence of at least one alkali selected from the group consisting of an alkali metal compound and an ammonium compound soluble in water and alkaline in nature, and subsequently distilling the resultant treated solution.
    Type: Grant
    Filed: December 19, 1986
    Date of Patent: March 21, 1989
    Assignee: Nippon Shokubai Kagaku Kogyo
    Inventors: Michio Ueshima, Yoshiyuki Takahashi, Masatoshi Tsuchino, Noboru Saito
  • Patent number: 4772754
    Abstract: The invention relates to a process for the isolation of p-hydroxybenzaldehyde from the reaction mixture obtained by oxidizing p-cresol with oxygen or oxygen-containing gases in methanol in the presence of Na or K hydroxide and an Mn, Ni, Cr or Co salt. The procedure in this process is optionally to add water to the reaction mixture, to heat the resulting solution and to filter off the precipitated Mn, Ni, Cr or Co oxide-hydrate, to remove the methanol from the filtrate by distillation, to cool the residual aqueous solution and thus to allow the p-hydroxybenzaldehyde to crystallize out in the form of the Na or K salt.Alternatively, the reaction mixture is first dried by atomization, the soluble constituents of the dry substance are then dissolved in hot water, the undissolved Mn, Ni, Cr or Co oxide-hydrate is filtered off and the salt of p-hydroxybenzaldehyde is again allowed to crystallize out by cooling the filtrate.
    Type: Grant
    Filed: November 30, 1987
    Date of Patent: September 20, 1988
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Freimund Rohrscheid
  • Patent number: 4748278
    Abstract: The invention relates to a process for the isolation of p-hydroxybenzaldehyde from the reaction mixture obtained by oxidizing p-cresol with oxygen or oxygen-containing gases in methanol in the presence of Na or K hydroxide and an Mn, Ni, Cr or Co salt. The procedure in this process is optionally to add water to the reaction mixture, to heat the resulting solution and to filter off the precipitated Mn, Ni, Cr or Co oxide-hydrate, to remove the methanol from the filtrate by distillation, to cool the residual aqueous solution and thus to allow the p-hydroxybenzaldehyde to crystallize out in the form of the Na or K salt.Alternatively, the reaction mixture is first dried by atomization, the soluble constituents of the dry substance are then dissolved in hot water, the undissolved Mn, Ni, Cr or Co oxide-hydrate is filtered off and the salt of p-hydroxybenzaldehyde is again allowed to crystallize out by cooling the filtrate.
    Type: Grant
    Filed: July 17, 1986
    Date of Patent: May 31, 1988
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Freimund Rohrscheid
  • Patent number: 4709088
    Abstract: A process for producing 2,6-naphthalenedicarboxylic acid which comprises oxidizing 2,6-diisopropylnaphthalene or its oxidation product as a starting material with molecular oxygen in a reaction medium containing at least 50% by weight of an aliphatic monocarboxylic acid having not more than 3 carbon atoms in the presence of an oxidation catalyst comprising (A) at least one heavy metal element selected from the group consisting of cobalt and manganese, and (B) bromine element, the 2,6-diisopropylnaphthalene and/or its oxidation product being used in a proportion of 0.1 to 5 moles per gram-atom of the heavy metal element of the oxidation catalyst.
    Type: Grant
    Filed: July 15, 1986
    Date of Patent: November 24, 1987
    Assignee: Teijin Petrochemical Industries, Ltd.
    Inventors: Isao Hirose, Tamio Amemiya, Tokuji Sakai
  • Patent number: 4700009
    Abstract: The present disclosure is concerned with a novel process for the manufacture of substituted benzaldehydes, namely of benzaldehydes of the formula ##STR1## wherein R represents a methoxy or tert.butyl group. The compounds of formula I are known substances, useful as, e.g. intermediates.
    Type: Grant
    Filed: January 28, 1986
    Date of Patent: October 13, 1987
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Nosberger, Paul
  • Patent number: 4691061
    Abstract: Vanillin is produced from alkaline oxidation treatment of acetovanillone or acetovanillone-rich internal waste streams of lignin processes without the need for utilizing nitrobenzene as an oxidizing agent.
    Type: Grant
    Filed: September 10, 1986
    Date of Patent: September 1, 1987
    Assignee: Monsanto Company
    Inventors: Bill S. K. Fung, Bjorn F. Hrutfiord
  • Patent number: 4562297
    Abstract: 3,5-Dihydrocarbyl-4-hydroxybenzaldehydes are prepared by intimately contacting a 4-(1-alkenyl)-2,5-dihydrocarbylphenol, such as 1,1-dimethyl-2-(3,5-di-t-butyl-4-hydroxyphenyl)ethene, with at least a stoichiometric amount of an oxygen-containing gas at about 50.degree.-25.degree. C. in the presence of an alcohol solvent and a catalytic amount of an alkali or alkaline earth metal hydroxide.
    Type: Grant
    Filed: November 2, 1984
    Date of Patent: December 31, 1985
    Assignee: Ethyl Corporation
    Inventor: Jerry M. Roper