EP1023255A1 - Procede pour la preparation d'aldehydes et d'acides carboxyliques par oxydation d'alcools primaires - Google Patents

Procede pour la preparation d'aldehydes et d'acides carboxyliques par oxydation d'alcools primaires

Info

Publication number
EP1023255A1
EP1023255A1 EP98959700A EP98959700A EP1023255A1 EP 1023255 A1 EP1023255 A1 EP 1023255A1 EP 98959700 A EP98959700 A EP 98959700A EP 98959700 A EP98959700 A EP 98959700A EP 1023255 A1 EP1023255 A1 EP 1023255A1
Authority
EP
European Patent Office
Prior art keywords
primary alcohols
alcohols
reaction
primary
oxidation
Prior art date
Legal status (The legal status 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 status listed.)
Withdrawn
Application number
EP98959700A
Other languages
German (de)
English (en)
Inventor
Albert Thomas Herrmann
Ernst Tönsen
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sasol Germany GmbH
Original Assignee
RWE Dea AG fuer Mineraloel und Chemie
RWE Dea AG
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 RWE Dea AG fuer Mineraloel und Chemie, RWE Dea AG filed Critical RWE Dea AG fuer Mineraloel und Chemie
Publication of EP1023255A1 publication Critical patent/EP1023255A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
    • B01J23/54—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
    • B01J23/56—Platinum group metals
    • B01J23/64—Platinum group metals with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • B01J23/644—Arsenic, antimony or bismuth
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
    • C07C45/37—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of >C—O—functional groups to >C=O groups
    • C07C45/38—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of >C—O—functional groups to >C=O groups being a primary hydroxyl group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/78—Separation; Purification; Stabilisation; Use of additives
    • C07C45/81—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
    • C07C45/82—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
    • C07C45/84—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation by azeotropic distillation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
    • C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
    • C07C51/23—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of oxygen-containing groups to carboxyl groups
    • C07C51/235—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of oxygen-containing groups to carboxyl groups of —CHO groups or primary alcohol groups

Definitions

  • the invention relates to a process for the oxidation of alcohols in
  • RCH 2 OH + '/ 2 O 2 ⁇ RCHO + H 2 O is known and is used extensively in technology. A large number of other catalysts / catalyst systems are also known. Silver and iron-molybdenum mixed oxides, which are technical catalysts, should also be mentioned here Have gained importance
  • the oxidation of primary alcohols (without another secondary hydroxyl group) by palladium or platinum catalysts supported on aluminum oxide or aluminum silicates in the presence of atmospheric oxygen without oxygen activators is either not known in the art or such catalyst systems are described as inactive (Fat Sei Tech 15, (94), 1992)
  • the object of the present invention is to provide a highly specific catalyst system which enables the oxidation of primary, preferably long-chain alcohols, which need not contain any further activating groups, by atmospheric oxygen in the liquid phase at low temperatures and pressures, and at the same time those known from the prior art Disadvantages such as the use of high temperatures, pressures, oxygen activators, alkali, acid or solvents are overcome
  • the metals used according to the invention can of course also be in the form of compounds, in particular in the form of their oxides.
  • the catalysts used according to the invention are also active in the presence of water.
  • the catalysts used according to the invention are activated without oxygen in the presence of the alcohol before the start of the oxidation
  • reaction is preferably carried out continuously and the primary alcohol is brought into contact with the catalyst several times.
  • the preferred oxidizing agent is molecular oxygen, which is used as a mixture in the form of atmospheric oxygen for reasons of cost
  • Preferred starting materials are primary alcohols with 4 to 32, particularly preferably 4 to 16 carbon atoms, where - if the primary alcohol is an alcohol with a
  • Branch is used in the 2 position - the carbon number is preferably 8 to 32, particularly preferably 8 to 22 or 8 to 24
  • the oxidation reaction is advantageously carried out in a fixed bed reactor. Space velocity and residence time are strongly dependent on the reactor design, but space velocities of 0.5 to 10 h "1 and residence times of 1 to 10 min are generally set
  • the primary alcohol is oxidized in a first reaction up to the aldehyde stage, the conversion of the primary alcohol to the aldehyde preferably being kept below 40% for each contacting (passage) and further preferably the aldehyde is removed by distillation
  • the oxidation to the aldehydes according to the invention is advantageously followed by an azeotropic distillation.
  • the mixture for the azeotropic distillation is preferably further
  • aldehydes form an azeotrope with water.
  • hexanal forms an azeotrope with water, which boils at 91 ° C.
  • Hexanol and hexanoic acid also form azeotropes with water. This boils at 97.8 and 99.9 ° C respectively.
  • the runs Distillation surprisingly easy.
  • Salts of transition metals such as cobalt, manganese, iron, nickel, silver, cerium or vanadium are, for example, catalytically active.
  • transition metals such as cobalt, manganese, iron, nickel, silver, cerium or vanadium
  • alkali metal salts of weak acids but also barium salts of the metals, it is known that these improve the selectivity

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

L'invention concerne un procédé pour l'oxydation d'alcools primaires en vue d'obtenir des aldéhydes et/ou des acides carboxyliques, en présence d'un catalyseur supporté sur des oxydes d'aluminium ou des silicates d'aluminium, contenant du palladium, du platine, du cobalt, du rhodium, du ruthénium, de l'iridium, du rhénium, éventuellement avec des cocatalyseurs.
EP98959700A 1997-10-02 1998-09-26 Procede pour la preparation d'aldehydes et d'acides carboxyliques par oxydation d'alcools primaires Withdrawn EP1023255A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19743621A DE19743621C1 (de) 1997-10-02 1997-10-02 Verfahren zur Herstellung von Aldehyden und Carbonsäuren durch Oxidation primärer Alkohole
DE19743621 1997-10-02
PCT/DE1998/002917 WO1999018058A1 (fr) 1997-10-02 1998-09-26 Procede pour la preparation d'aldehydes et d'acides carboxyliques par oxydation d'alcools primaires

Publications (1)

Publication Number Publication Date
EP1023255A1 true EP1023255A1 (fr) 2000-08-02

Family

ID=7844425

Family Applications (1)

Application Number Title Priority Date Filing Date
EP98959700A Withdrawn EP1023255A1 (fr) 1997-10-02 1998-09-26 Procede pour la preparation d'aldehydes et d'acides carboxyliques par oxydation d'alcools primaires

Country Status (6)

Country Link
US (1) US6476260B1 (fr)
EP (1) EP1023255A1 (fr)
JP (1) JP2001519323A (fr)
CA (1) CA2305676A1 (fr)
DE (1) DE19743621C1 (fr)
WO (1) WO1999018058A1 (fr)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4250954B2 (ja) * 2002-04-26 2009-04-08 住友化学株式会社 ルテニウム担持アルミナの製造方法およびアルコールの酸化方法
US8669397B2 (en) * 2009-06-13 2014-03-11 Rennovia, Inc. Production of adipic acid and derivatives from carbohydrate-containing materials
NZ596975A (en) * 2009-06-13 2014-04-30 Rennovia Inc Production of adipic acid and derivatives from carbohydrate-containing materials
EP2440513B1 (fr) * 2009-06-13 2018-08-22 Archer-Daniels-Midland Company Production d'acide glutarique et de dérivés à partir de matières contenant des glucides
US8669393B2 (en) * 2010-03-05 2014-03-11 Rennovia, Inc. Adipic acid compositions
US9770705B2 (en) 2010-06-11 2017-09-26 Rennovia Inc. Oxidation catalysts
KR101716563B1 (ko) * 2015-03-27 2017-03-15 지에스칼텍스 주식회사 메틸에틸케톤 및 이소부틸알데하이드를 포함하는 공비 혼합물로부터 메틸에틸케톤을 분리하는 방법
US10532970B2 (en) 2016-06-29 2020-01-14 Basf Se Process for the preparation of alpha, beta unsaturated aldehydes by oxidation of alcohols in the presence of a liquid phase
MX2019011258A (es) 2017-03-20 2019-12-05 Basf Se Proceso para la preparacion de aldehidos alfa, beta insaturados mediante oxidacion de alcoholes en presencia de una fase liquida.
EP3728173A1 (fr) 2017-12-21 2020-10-28 Basf Se Procédé de préparation d'aldéhydes alpha,bêta-insaturés par oxydation d'alcools en présence d'une phase liquide
US11046632B2 (en) * 2017-12-21 2021-06-29 Basf Se Process for the preparation of 3-methyl-2-buten-1-al
WO2020048855A1 (fr) 2018-09-07 2020-03-12 Basf Se Procédé de préparation d'aldéhydes alpha,bêta-insaturés par oxydation d'alcools en présence d'une phase liquide
WO2020048852A1 (fr) * 2018-09-07 2020-03-12 Basf Se Procédé de préparation d'aldéhydes alpha, bêta insaturés par oxydation d'alcools en présence d'une phase liquide

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2537576B1 (fr) * 1982-12-08 1987-07-10 Rhone Poulenc Sa Procede d'oxydation d'alcools en composes carbonyles correspondants
JPS62265243A (ja) 1986-05-13 1987-11-18 Showa Denko Kk １，４−シクロヘキサンジオンの製造方法
JP2950851B2 (ja) * 1989-06-23 1999-09-20 三菱レイヨン株式会社 鉄・アンチモン・リン含有金属酸化物触媒組成物およびその製法
US4996007A (en) 1990-01-19 1991-02-26 Shell Oil Company Process for the oxidation of alcohols to aldehydes/acids/esters
DE4228487A1 (de) * 1991-08-30 1993-03-04 Kao Corp Verfahren zur herstellung einer eine carbonyl- und/oder carboxylgruppe aufweisenden verbindung

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9918058A1 *

Also Published As

Publication number Publication date
JP2001519323A (ja) 2001-10-23
US6476260B1 (en) 2002-11-05
WO1999018058A1 (fr) 1999-04-15
CA2305676A1 (fr) 1999-04-15
DE19743621C1 (de) 1999-03-25

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