WO2005118545A1 - Oxydation en phase gazeuse de composes heterocycliques substitues par alkyle - Google Patents

Oxydation en phase gazeuse de composes heterocycliques substitues par alkyle

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Publication number
WO2005118545A1
WO2005118545A1 PCT/EP2005/005926 EP2005005926W WO2005118545A1 WO 2005118545 A1 WO2005118545 A1 WO 2005118545A1 EP 2005005926 W EP2005005926 W EP 2005005926W WO 2005118545 A1 WO2005118545 A1 WO 2005118545A1
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WO
WIPO (PCT)
Prior art keywords
oxide
catalyst
active
gas
alkyl
Prior art date
Application number
PCT/EP2005/005926
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German (de)
English (en)
Inventor
Jochen Petzoldt
Hagen Wilmer
Frank Rosowski
Original Assignee
Basf Aktiengesellschaft
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Basf Aktiengesellschaft filed Critical Basf Aktiengesellschaft
Publication of WO2005118545A1 publication Critical patent/WO2005118545A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/79—Acids; Esters
    • C07D213/80—Acids; Esters in position 3

Definitions

  • the present invention relates to a process for the preparation of heterocyclic carboxylic acids and heterocyclic carboxylic acid anhydrides comprising the partial gas phase oxidation of alkyl-substituted heterocyclic compounds in the presence of coated catalysts, which is distinguished by high yields of valuable product at high catalyst loads with the starting product.
  • Nicotinic acid is widely used in the fields of medicine and agriculture as a B vitamin and as an intermediate for pharmaceutical products and for growth regulators of plants.
  • Nicotinic acid can be produced industrially by catalytic gas phase oxidation of 3-picoline in tube bundle reactors.
  • the starting material is a mixture of a gas containing molecular oxygen, for example air, water vapor and the 3-picoline to be oxidized.
  • the mixture is usually passed through a plurality of tubes arranged in a reactor (tube bundle reactor), in which there is a bed of at least one catalyst.
  • the active mass of the catalysts comprises 5 to 30% by weight of one or more compounds of the formula M x V 6 0 15 , where M is selected from Li, Na, K, Rb, Cs, Mg, Ca and mixtures of these elements and 0 ⁇ x ⁇ 1.
  • the carrier material consists of 90 to 100% by weight of SiO 2 and 0 to 10% by weight of Al 2 O 3 and / or ZrO 2 , the BET specific surface area being 1 to 50 m 2 / g.
  • the active mass is applied to grains of the carrier material with a diameter of 1 to 3 millimeters. The use of coated catalysts based on support bodies is not described.
  • CH 543 510 discloses a process for the preparation of pyridine carboxylic acids in the gas phase by contacting the methyl-substituted pyridine compound with an oxygen-containing gas.
  • the catalyst consists of a vanadium oxide-containing active material that is applied to grains of the carrier material silicon carbide with a diameter of approx. 2 millimeters. The use of coated catalysts based on support bodies is not described.
  • DE 2647 712 describes a process for the production of nicotinic acid from alkylpyridines with ⁇ -methyl or ethyl groups by gas phase oxidation on one solid catalyst phase with air and water vapor.
  • a V 2 O 5 catalyst which contains TiO 2 as a promoter and is heated to 1250 ° C. serves as the catalyst.
  • Pumice and zeolites are described as substrates.
  • EP-A 747 359 describes a process for the production of nicotinic acid by a single-stage gas-phase oxidation of ⁇ -picoline with oxygen in the presence of water vapor. The process is carried out at temperatures from 250 to 290 ° C. in the presence of a catalyst based on oxides of vanadium and titanium. The yield is at least 82%. V 2 O 5 is supported on TiO 2 . The use of coated catalysts based on support bodies is not described.
  • the catalyst used is a vanadium oxide-containing catalyst, the support of which consists of a titanium dioxide with a high surface area (> 100 m 2 / g) produced by the sulfate method, the vanadium oxide content being between 5 and 50% by weight.
  • the TiO 2 supported with vanadium oxide is pressed into tablets, these are then ground and sieved and one of the sieve fractions is used as a catalyst. The use of coated catalysts is not described.
  • CN 1 296 004 also describes a process for the production of nicotinic acid.
  • the active composition of the catalyst contains 58% by weight of NH 4 VO as the main constituent, as well as Sb 2 O 3 , Sm 2 O 3 , TiO 2 and (NH 4 ) 2 Cr 2 O 7 .
  • the active mass is carried by spraying onto Al 2 O 3 or silicon carbide balls.
  • the supported catalyst is activated at 400 to 450 ° C for 6 to 8 hours.
  • Japanese published patent application JP 2002-331239 describes a gas phase process for the production of nicotinic acid from 3-picoline in the presence of catalysts containing vanadium and chromium.
  • the active mass is applied to silica sol and the catalyst grains suitable for the reaction are obtained by sieving. The use of coated catalysts is not described.
  • J. Appl. Chem. Biotechnol. 27 (1977) 499-509 describes the oxidation of 3-methylpyridine to nicotinic acid using supported catalysts with a coating of vanadium pentoxide and titanium dioxide in a weight ratio V 2 O 5 to TiO 2 greater than 1: 4 on pumice stone, which according to 5 hour annealing at 400 ° C has a BET surface area of 15-100 m 2 / g, preferably 25-50 m 2 / g.
  • RZA space-time yield
  • the catalyst load gives the mass of the starting product, which is brought into contact with the total mass of the catalyst per unit of time.
  • the catalyst load is usually characterized by the specification of the WHSV (weight hourly space velocity):
  • the object of this invention was therefore to find a process for the preparation of heterocyclic carboxylic acids in which the space-time yield is increased compared to the known processes.
  • this object is achieved by a process for the preparation of heterocyclic carboxylic acids and heterocyclic carboxylic acid anhydrides comprising the partial gas phase oxidation of alkyl-substituted heterocyclic compounds by reacting the alkyl-substituted heterocyclic compounds with gas containing molecular oxygen in the presence of a supported catalyst, the vanadium and at least contains a support material in the active composition, characterized in that the supported catalyst is a coated catalyst, in which the active composition is applied in a shell shape to a support body and the vanadium content of the active composition, calculated as V 2 O 5 , is at most 20% by weight ,
  • GHSV gas hourly space velocity [I (gas) / l (cat) / h]
  • I (gas) / l (cat) / h] gas hourly space velocity
  • a high RZA can also be achieved by increasing the GHSV while maintaining the starting gas composition.
  • GHSV and WHSV correlate linearly.
  • the higher RZA reduces the reaction volume with a constant volume flow.
  • the WHSV is a measure of the catalyst load, ie the higher the WHSV, the greater the catalyst load.
  • the process according to the invention is preferred for a WHSV of at least 0.04 h "1 , particularly preferably at least 0.06 h " 1 , very particularly preferably at least 0.075 h "1 and in particular at least 0.09 h " 1 . It is most preferred to carry out the process at a WHSV of at least 0.1h '1 .
  • heterocyclic compounds which are oxidized to carboxylic acids or carboxylic anhydrides in the process according to the invention have an at least 5-membered ring, at least one ring atom being a heteroatom selected from nitrogen, oxygen or sulfur.
  • Examples which do not represent an enumeration limiting the invention are alkyl-substituted pyrroles, furans, thiophenes, imidazoles, oxazoles, thiazoles, pyrazoles, 3-pyrroline pyrrolidines, pyridines, pyrimidines, purines, quinolines, isoquinolines, carbazoles, indoles and benzofurans.
  • Preferred alkyl substituents are branched and unbranded Ci to C 6 alkyl radicals such as methyl, ethyl, n-propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2nd -Methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, -ethylpropyl, hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1, 1-dimethylbutyl, 1, 2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl,
  • alkyl radicals are methyl, ethyl and n-propyl.
  • heterocyclic compounds can be substituted at different ring positions with respect to the hetero atom (s) one or more times with the same or different alkyl radicals.
  • Preferred alkyl substituents are C 1 to C 4 alkyl, particularly preferably methyl, ethyl, n-propyl, particularly preferred is methyl.
  • Examples of special alkyl-substituted heterocyclic compounds which can be oxidized to carboxylic acids by the process according to the invention are methylpyrrole, ethylpyrroles, propylpyrroles, methylfurans, ethylfurans, propylfuran, methylthiophenes, ethylthiophenes, propylthiophenes, methylimidazoles, ethylimidazoles, propylimidazoles, propylimidazoles, propylimidazoles, Ethyloxazole, propyloxazole, methylthiazole, ethylthiazole, propylthiazole, methylpyrazole, ethylpyrazole, propylpyrazole, methyl-3-pyrroline-pyrolidine, ethyl-3-pyrrolinepyrolidine, propyl-3-pyrrolinepyrolidine, picoline, ethyl
  • 3-Picolin is very particularly preferred.
  • nicotinic acid (3-pyridinecarboxylic acid) from 3-picoline (3-methylpyridine) is particularly preferred.
  • the carrier material is a component of the active composition (active composition).
  • active composition In the case of a coated catalyst, this active composition is applied to the carrier body.
  • the carrier body preferably consists of a material which is essentially inert and essentially non-porous under the reaction conditions of the process according to the invention.
  • Shell catalysts are understood to mean catalysts which consist of support bodies, the outer surface of which are partially or completely covered with a catalytically active composition.
  • the outer surface of a carrier body is the surface that can be wetted by liquid water under normal conditions by completely immersing the body in the water.
  • Oxidized supported catalysts are suitable as catalysts.
  • the active composition contains at least one carrier material.
  • the carrier materials can be titanium dioxide, zirconium dioxide, silicon oxide, aluminum oxide, magnesium oxide, silicon carbide, titanium dioxide and zirconium dioxide are preferred, in particular titanium dioxide is used.
  • the titanium dioxide used is preferably in anatase form and advantageously has a BET surface area of 5 to 50 m / g, preferably 10 to 35 m 2 / g, in particular 13 to 28 m 2 / g.
  • Mixtures of titanium dioxide in anatase form with different BET surface areas can also be used, with the proviso that the resulting BET surface area has a value of 5 to 50 m 2 / g, preferably 10 to 35 m / g, in particular 13 to 28 m 2 / g.
  • commercially available TiO 2 with a BET surface area of approximately 20 m 2 / g can be used.
  • Vanadium oxides or vanadium compounds which convert to vanadium oxide when heated in air are preferably used as the component of the active composition containing vanadium.
  • V 2 O 5 or NH V0 3 are preferably used.
  • the amount of vanadium, calculated as V 2 O 5 and related is preferably in the range from 0.5 to 15, particularly preferably in the range from 1 to 12,% by weight.
  • a preferred embodiment of the invention is accordingly a process for the preparation of heterocyclic carboxylic acids and heterocyclic carboxylic acid anhydrides comprising the partial gas phase oxidation of alkyl-substituted heterocyclic compounds by reacting the alkyl-substituted heterocyclic compounds with molecular oxygen-containing gas in the presence of a supported catalyst which contains vanadium in the active composition characterized in that the supported catalyst is a coated catalyst in which the active mass is applied in a shell shape on a support body and 90 to 99% by weight of titanium, calculated as TiO 2 , 1 to 10% by weight of vanadium, calculated as V 2 O 5 , and optionally contains further constituents in an amount of up to 1% by weight.
  • the catalytically active composition can contain a large number of other oxidic compounds in small amounts which, as promoters, influence the activity and selectivity of the catalyst, for example by reducing or increasing its activity.
  • promoters are, for example, the alkali metal oxides, thallium (l) oxide, aluminum oxide, zirconium oxide, iron oxide, nickel oxide, cobalt oxide, manganese oxide, tin oxide, silver oxide, copper oxide, chromium oxide, molybdenum oxide, tungsten oxide, iridium oxide, tantalum oxide, niobium oxide, arsenic oxide, antimony oxide, cerium oxide, gold -, platinum and palladium compounds and phosphorus compounds such as phosphorus pentoxide.
  • the alkali metal oxides act, for example, as promoters which reduce activity and increase selectivity. Based on the total mass of the catalyst, the proportion of active mass is 5 to 50, preferably 5 to 40, particularly preferably 10 to 35% by weight.
  • the active composition of the catalyst accordingly contains further constituents selected from alkali metal oxides, thallium (l) oxide, aluminum oxide, zirconium oxide, iron oxide, nickel oxide, cobalt oxide, manganese oxide, tin oxide, silver oxide, copper oxide, chromium oxide, molybdenum oxide, tungsten oxide, Iridium oxide, tantalum oxide, niobium oxide, arsenic oxide, antimony oxide, cerium oxide and phosphorus oxide.
  • alkali metal oxides thallium (l) oxide, aluminum oxide, zirconium oxide, iron oxide, nickel oxide, cobalt oxide, manganese oxide, tin oxide, silver oxide, copper oxide, chromium oxide, molybdenum oxide, tungsten oxide, Iridium oxide, tantalum oxide, niobium oxide, arsenic oxide, antimony oxide, cerium oxide and phosphorus oxide.
  • an aqueous and / or organic solvent-containing solution or suspension of the active composition constituents and / or their precursor compounds which are hereinafter referred to as "mash" is used in the processes of DE-A 1642938 and DE-A 17 69 998 is, on a generally inert under the reaction conditions in a heated coating drum at elevated Sprayed on temperature until the desired proportion of active mass in total catalyst weight is reached.
  • the coating can also be carried out in fluidized coaters, as are given, for example, in DE 12 80 756.
  • organic binders preferably copolymers, advantageously in the form of an aqueous dispersion, of vinyl acetate / vinyl laurate, vinyl acetate / acrylate, styrene / acrylate, vinyl acetate maleate and vinyl acetate / ethylene to the mash, binder quantities of 10-20% by weight, based on the solids content of the mash, were used (EP-A 744214). If the mash is applied to the carrier without organic binders, coating temperatures above 150 ° C are advantageous.
  • the usable coating temperatures are between 50 and 450 ° C., depending on the binder used (DE 21 06 796).
  • the applied binders burn out within a short time after the catalyst has been introduced into the reactor and the reactor has been started up.
  • the addition of the binder also has the advantage that the active composition adheres well to the support, so that transport and filling of the catalyst are made easier.
  • Regularly shaped, mechanically stable carriers are suitable as carrier bodies, such as preferably spherical, ring-shaped, semi-ring-shaped, saddle-shaped, bowl-shaped, cube-shaped, cuboid, truncated cone or truncated cone, pyramid or truncated pyramid, prism-shaped or cylindrical carrier bodies. Ring-shaped carrier bodies are particularly preferred.
  • DE-A 3445289 (US-A 4,656, 157) describes, for example, a ring carrier which differs from “normal rings” in that its end faces are rounded.
  • EP-A 220933 describes a catalyst which has a "four-winged" shape, as a result of which the catalyst has better physical properties with regard to breaking strength and pressure build-up.
  • GB-A 21 93907 describes a catalyst in cylindrical shape, the outer shell of which is provided in the longitudinal direction with ribs which are dimensioned and arranged in such a way that the individual catalyst bodies cannot get caught.
  • US-A 4,328,130 also describes a catalytic converter form in which a cylinder is traversed in the longitudinal direction with a plurality of channels and ribs, the recesses being narrower than the ribs in order to avoid snagging.
  • Catalyst forms are known from EP-A 004 079 (USA 4,370,492 and US-A 4,370,261), which are strand sections with a star-shaped cross section or ribbed strands.
  • EP-A 1 108470 discloses inert carrier bodies in the form of rings, characterized in that the rings have one or more notches on the upper and / or lower flat side of the ring. On pages 8 to 12 of EP-A 1 108470 numerous possible embodiments of this type of support body are shown.
  • EP-A 552 287 discloses geometric structures provided with cavities which are suitable as support bodies for the coated catalysts of the process according to the invention. Specifically, the cylinders, cubes, cones, truncated cones, pyramids, truncated pyramids, spheres and prisms.
  • the cavities can be evenly spaced on the outer surface in which such cavities are located and can be of the type of grooves, holes and troughs.
  • the size of the support bodies is mainly determined by the dimension, especially by the inner diameter of the reaction tubes, when the catalyst is used in tube or tube bundle reactors.
  • the carrier diameter should then be between 1/2 and 1/10 of the inside diameter.
  • Steatite in the form of spheres with a diameter of 3 to 6 mm or rings with an outer diameter of 5 to 9 mm and a length of 4 to 7 mm is preferably used, the size being selected in accordance with the inner diameter of the reactor tube.
  • suitable materials for the carrier body are silicate, silicon carbide, porcelain, aluminum oxide, magnesium oxide, tin dioxide, rutile, aluminum silicate, magnesium silicate (steatite), duranite, earthenware, silicon dioxide, aluminates, metals, metal alloys, zirconium silicate or cerium silicate or mixtures thereof , with steatite being preferred.
  • the catalysts coated with active composition are filled into reaction tubes which are thermostatted from the outside to the reaction temperature, for example by means of salt melting, and the reaction gas at temperatures of generally above 290 ° C. to 400 ° C., preferably from 300 to 380 ° C., via the catalyst bed prepared in this way C and particularly preferably from 310 to 350 ° C and at an overpressure of generally 0.1 to 2.5 bar, preferably from 0.3 to 1.5 bar with a space velocity of generally 750 to 5000 h-1.
  • the reaction gas fed to the catalyst is generally generated by mixing a gas containing molecular oxygen, which in addition to oxygen may also contain suitable reaction moderators and / or diluents, such as water vapor, carbon dioxide and / or nitrogen, with the heterocyclic compound to be oxidized, where the gas containing the molecular oxygen, for example 1 to 99 mol%, preferably 2 to 50 mol% and particularly preferably 6 to 20 mol% oxygen, 0 to 50 mol%, preferably 0 to 35 mol% water vapor and 0 to 50 mol%, preferably 0 to 1 mol% carbon dioxide, balance nitrogen.
  • a gas containing molecular oxygen for example 1 to 99 mol%, preferably 2 to 50 mol% and particularly preferably 6 to 20 mol% oxygen, 0 to 50 mol%, preferably 0 to 35 mol% water vapor and 0 to 50 mol%, preferably 0 to 1 mol% carbon dioxide, balance nitrogen.
  • the reaction zone located towards the gas inlet of the reaction gas which generally comprises 30 to 80 mol% of the total catalyst volume, is reduced to 1 to 20 ° C, preferably by 1 to 10 ° C and in particular by 2 to 8 ° C higher reaction temperature than the reaction zone located towards the gas outlet thermostatted.
  • the gas phase oxidation can also be carried out without division into temperature zones at a single reaction temperature.
  • catalysts can be used in the above-mentioned reaction zones of the catalyst bed which differ in their catalytic activity and / or chemical composition of their active composition.
  • a catalyst is preferably used which is somewhat less catalytic than the catalyst located in the second reaction zone, ie toward the gas outlet Has activity.
  • the reaction is controlled by the temperature setting in such a way that in the first zone most of the heterocyclic compound contained in the reaction gas is converted with maximum yield. It is also possible to carry out the process with three, four or more reaction zones, the catalysts in the individual zones differing in their catalytic activity and / or chemical composition of their active composition.
  • the catalyst system can consist of three to five layers.
  • shell catalysts can be used in all reaction zones.
  • Salt bath-cooled tube bundle reactors as are customary in other partial oxidation reactions are preferred as reactors for carrying out the process according to the invention.
  • Such reactors have reaction tubes with diameters in the range of typically 20 to 30 mm and lengths in the range of typically 2 to 7 m. Several thousand pipes can be installed in a reactor. reactors This type is used, for example, in the prior art in the synthesis of phthalic anhydride, acrylic acid and maleic anhydride.
  • a suspension containing 422.4 g of anatase (BET surface area 20 m 2 / g), 17.6 g of V 2 O 5 , 47.5 g of oxalic acid, 135.4 g of formamide and 1577.3 g of water was in a spray dryer transferred a powder.
  • the weight of the catalytically active composition was 20.4%, based on the total weight of the catalyst.
  • a suspension containing 470.5 g of anatase (BET surface area 20 m 2 / g), 19.7 g of V 2 O 5 , 53.0 g of oxalic acid, 150.6 g of formamide and 706.5 g of water was added together with 53 , 2 g of Acronal ® DS 2348 as binder within 52 min in a coating drum on 1300 g of steatite rings of dimensions 8 * 6 * 1, 5 (outer diameter * height * inner diameter).
  • the weight of the catalytically active composition thus applied was 19.8%, based on the total weight of the catalyst.
  • Example S1 The preparation was carried out analogously to Example S1, but 142.9 g of the spray powder together with 52.0 g of the binding liquid were applied to 300 g of steatite balls with a diameter of 3.5 to 4.5 mm.
  • compositions of the educt and product gas mixtures were analyzed by means of gas chromatography.
  • 02 1220 g of the catalyst prepared according to Example S2 were introduced into a reactor with an inner diameter of 26 mm and a centered thermal sleeve with a 4 mm outer diameter.
  • the starting materials were metered in and the gas mixtures were analyzed analogously to Example O1.
  • the temperature for the production of nicotinic acid using the process according to the invention using the catalyst according to S2 was 321 ° C. (02a), 328 ° C. (02b) and 347 ° C. (O2c).
  • Example S4 1160 g of the catalyst prepared according to Example S4 were introduced into a reactor with an inner diameter of 26 mm and a centered thermal sleeve with a 4 mm outer diameter.
  • the starting materials were metered in and the gas mixtures were analyzed analogously to Example 01.
  • the temperature for producing nicotinic acid using the process according to the invention using the catalyst according to S4 was 351 ° C. (04a), 325 ° C. (04b), 353 ° C. ( 04c), 331 ° C (O4d).

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Catalysts (AREA)

Abstract

L'invention concerne un procédé pour produire des acides carboxyliques hétérocycliques et des anhydrides d'acide carboxylique hétérocycliques, comprenant l'oxydation en phase gazeuse partielle de composés hétérocycliques substitués par alkyle en présence des catalyseurs recouverts. Ledit procédé est caractérisé par des rendements élevés de produit valable provenant d'un catalyseur à charge élevée de produit de départ.
PCT/EP2005/005926 2004-06-04 2005-06-02 Oxydation en phase gazeuse de composes heterocycliques substitues par alkyle WO2005118545A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102004027414.2 2004-06-04
DE200410027414 DE102004027414A1 (de) 2004-06-04 2004-06-04 Gasphasenoxidation von alkylsubstituierten heterozyklischen Verbindungen

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WO2005118545A1 true WO2005118545A1 (fr) 2005-12-15

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102399183A (zh) * 2010-09-13 2012-04-04 朱比兰特生命科学有限公司 一种制备吡啶羧酸的方法
CN109661443A (zh) * 2016-08-29 2019-04-19 信越化学工业株式会社 涂覆组合物和被覆物品

Families Citing this family (3)

* Cited by examiner, † Cited by third party
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RU2704137C1 (ru) * 2019-07-24 2019-10-24 Федеральное государственное бюджетное учреждение науки "Федеральный исследовательский центр "Институт катализа им. Г.К. Борескова Сибирского отделения Российской академии наук" (ИК СО РАН, Институт катализа СО РАН) Способ получения никотиновой кислоты
RU2704139C1 (ru) * 2019-07-24 2019-10-24 Федеральное государственное бюджетное учреждение науки "Федеральный исследовательский центр "Институт катализа им. Г.К. Борескова Сибирского отделения Российской академии наук" (ИК СО РАН, Институт катализа СО РАН) Способ получения никотиновой кислоты
RU2704138C1 (ru) * 2019-07-24 2019-10-24 Федеральное государственное бюджетное учреждение науки "Федеральный исследовательский центр "Институт катализа им. Г.К. Борескова Сибирского отделения Российской академии наук" (ИК СО РАН, Институт катализа СО РАН) Способ получения никотиновой кислоты

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WO1998037967A1 (fr) * 1997-02-27 1998-09-03 Basf Aktiengesellschaft Procede de preparation de catalyseurs sous forme de coque pour l'oxydation catalytique en phase gazeuse d'hydrocarbures aromatiques
DE19839559A1 (de) * 1998-09-01 2000-03-02 Degussa Verfahren zur Herstellung von Nikotinsäure
CN1296004A (zh) * 1999-11-10 2001-05-23 黑龙江省石油化学研究院 烟酸的生产方法

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WO1998037967A1 (fr) * 1997-02-27 1998-09-03 Basf Aktiengesellschaft Procede de preparation de catalyseurs sous forme de coque pour l'oxydation catalytique en phase gazeuse d'hydrocarbures aromatiques
DE19839559A1 (de) * 1998-09-01 2000-03-02 Degussa Verfahren zur Herstellung von Nikotinsäure
CN1296004A (zh) * 1999-11-10 2001-05-23 黑龙江省石油化学研究院 烟酸的生产方法

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102399183A (zh) * 2010-09-13 2012-04-04 朱比兰特生命科学有限公司 一种制备吡啶羧酸的方法
EP2428505A3 (fr) * 2010-09-13 2012-08-01 Jubilant Life Sciences Limited Procédé de production d'acides carboxyliques à pyridine
CN102399183B (zh) * 2010-09-13 2016-05-04 朱比兰特生命科学有限公司 一种制备吡啶羧酸的方法
CN109661443A (zh) * 2016-08-29 2019-04-19 信越化学工业株式会社 涂覆组合物和被覆物品

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