EP2456745A2 - Procédé de préparation d'acides décane-carboxyliques - Google Patents

Procédé de préparation d'acides décane-carboxyliques

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Publication number
EP2456745A2
EP2456745A2 EP10722067A EP10722067A EP2456745A2 EP 2456745 A2 EP2456745 A2 EP 2456745A2 EP 10722067 A EP10722067 A EP 10722067A EP 10722067 A EP10722067 A EP 10722067A EP 2456745 A2 EP2456745 A2 EP 2456745A2
Authority
EP
European Patent Office
Prior art keywords
mixture
aldehydes
oxidation
catalyst
aliphatic
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Withdrawn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
EP10722067A
Other languages
German (de)
English (en)
Inventor
Michael Grass
Alfred Kaizik
Hans-Gerd Lüken
Wilfried Büschken
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.)
Evonik Operations GmbH
Original Assignee
Evonik Oxeno GmbH and Co KG
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 Evonik Oxeno GmbH and Co KG filed Critical Evonik Oxeno GmbH and Co KG
Publication of EP2456745A2 publication Critical patent/EP2456745A2/fr
Withdrawn legal-status Critical Current

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Classifications

    • 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
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
    • C07C45/74—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with dehydration
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B61/00—Other general methods
    • 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
    • C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
    • C07C45/50—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide by oxo-reactions
    • 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
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/62—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by hydrogenation of carbon-to-carbon double or triple bonds
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
    • C07C53/126—Acids containing more than four carbon atoms

Definitions

  • the present invention relates to the preparation of decanecarboxylic acids, in particular of decanecarboxylic acid mixtures with a high proportion of 2-propylheptanoic acid.
  • Decanecarboxylic acids can be used, for example, as a precursor for the preparation of peresters, detergents and lubricants.
  • Patenschriften have in common that in at least one
  • a rhodium catalyst having a diphosphine ligand having a xanthene skeleton is used.
  • 2-butenes can be hydroformylated under isomeric conditions.
  • the ratio of n-pentanal to 2-methylbutanal is 85 to 15.
  • DE 101 08 474 and DE 101 08 475 disclose processes in which the
  • Hydroformylation is carried out in two stages.
  • first hydroformylation step using a catalyst consisting of rhodium and a
  • Decancarboxylic claimed.
  • a synthesis pathway is sketched, which comprises the following steps: Aldol condensation of the pentanal mixture to form a
  • 2-ethylhexanoic acid can be prepared by oxidation of 2-ethylhexanal, with additions of
  • Alkali metal salts of 2-ethylhexanoic acid increase the yields.
  • condensation mixture (decenal) can either be partially hydrogenated to give decanalen in the presence of palladium-containing catalysts or completely to give decanols.
  • the present invention had the object of specifying a method based on a linear C4-olefin-containing hydrocarbon mixture, which additionally contains isobutene, provides decanals in a few steps, which are oxidized with oxygen-containing gases in high yields to the corresponding decanecarboxylic acids, without that neither a
  • the invention therefore provides a process for the preparation of a
  • a mixture of isomeric decanecarboxylic acids the following steps being carried out: ⁇ a) hydroformylation of a hydrocarbon mixture containing linear C4 olefins using a rhodium-containing catalyst system; b) aldol condensation of a mixture of C5 aliphatic aldehydes,
  • the process according to the invention has the following advantages:
  • the oxidation is very selective even at very high conversions, so that only small losses of substance occur. Accordingly, even small amounts of by-products, which must be disposed of. Since no catalyst is used, there are no costs for catalyst, separation of the used catalyst or its derivatives and their disposal.
  • the decanal mixture which has been prepared starting from linear butenes in a three-stage synthesis and based on the Decanalanteil contains at least 80% by mass of 2-propylheptanal, oxidized to the corresponding Decancarbonklaren.
  • the oxidation is carried out neither with the addition of a catalyst, usually a transition metal compound, nor with the addition of a stabilizer, for example an alkali metal or alkaline earth metal salt of a carboxylic acid.
  • oxygen, air or other oxygen-containing gas mixtures can be used.
  • oxygen or oxygen / nitrogen mixtures with more than 10% by volume of oxygen are used in the process according to the invention.
  • the oxidation is carried out in the temperature range from 10 to 80 ° C., in particular in the temperature range from 20 to 50 ° C., very particularly in the temperature range from 25 to 35 ° C.
  • the absolute reaction pressure, measured in the gas phase at the top of the reactor, is 0.1 to 1 MPa, in particular 0.1 to 0.5 MPa.
  • the oxidation is carried out in the liquid / gas mixed phase.
  • Decanal mixture and / or the resulting Decancarbonklaregemisch is present as a continuous liquid phase, in which the oxidizing gas or gas mixture is introduced. Most of the gas mixture is present as a disperse phase.
  • Reactors which may be used are stirred tanks or bubble column reactors, into which gas is introduced near the bottom by means of a gas distribution device, for example a frit or a nozzle.
  • the oxidation may be carried out continuously or batchwise in one or more reactors. When using multiple reactors, these may be connected in series and / or in parallel.
  • the reaction mixture consists of decanecarboxylic acids with a content of 2-propylheptanoic acid of at least 70% by mass, unreacted Cio aldehydes, by-products and optionally of substances which were already present in the feed decanal.
  • the content of decanecarboxylic acids in this mixture is in the range of 50 to 98% by mass, in particular in the range of 80 to 93% by mass.
  • This mixture is preferably separated by distillation.
  • Separation can be done at atmospheric pressure or reduced pressure.
  • the distillative separation is carried out in vacuo.
  • the oxidation mixture is preferably separated into the following four fractions: a) A low-boiling fraction which is essentially oxidized
  • the distillative separation is continuous or
  • the low boilers are separated in the second column, the aldehydes and in the third column, the decanecarboxylic acids in each case as the top product.
  • the bottom product of the third column is the high boilers.
  • the separated low boilers and high boilers can be used thermally or used as starting material for a synthesis gas plant. If the high boiler fraction contains a large amount of decanecarboxylic acid ester, it can optionally be worked up to decanecarboxylic acids.
  • the separated aldehyde fraction can be completely or partially recycled to the oxidation state.
  • decanecarboxylic acids obtained can be used, for example, for the production of peresters, siccatives, detergents, plasticizers or lubricants.
  • Starting materials for the process according to the invention are
  • Hydrocarbon mixtures which have no polyunsaturated compounds and no acetylene compounds and contain at least one of the olefins cis-2-butene, trans-2-butene and 1-butene.
  • suitable mixtures of linear butenes can be obtained from the C 4 fraction of a steam cracker for the process according to the invention.
  • butadiene is removed in the first step. This is done either by extraction or extraction distillation of butadiene or its
  • the now isobutene-free C 4 cut , the raffinate II contains, as desired, the linear butenes and optionally butanes.
  • the 1-butene can be removed by distillation. Both Fractions containing but-1-ene or but-2-ene can be used in the process of the present invention.
  • raffinate I raffinate I
  • raffinate II a similar composition
  • a mixture can be obtained which consists of 2-butenes, small amounts of 1-butene and optionally n-butane and isobutane and isobutene.
  • Another feed mixture for the process according to the invention is the C 4 mixture remaining from the oligomerization of a mixture of linear olefins (for example raffinate II or raffinate III), butane, optionally from isobutene, 2-butenes and small amounts of 1-butene consists. Preference is given to using hydrocarbon mixtures with preferably at least 15% by mass of linear butenes.
  • the first step of the process according to the invention is hydroformylation.
  • n-pentanal is produced in a selectivity greater than 85%.
  • 1-butene is to be converted, this can be done, for example, with the aid of a catalyst system consisting of rhodium and a monophosphine, for example triphenylphosphine.
  • 2-butenes are to be implemented, the
  • Hydroformylation be carried out under isomerizing conditions. That is, a catalyst is used which under reaction conditions is able to shift both the double bonds in all linear butenes, i. H. to isomerize, as well as hydroformylate terminally. There are catalysts used, the linear butenes with any ratios of isomers with an n-selectivity (ratio of n-pentanal to sum of all
  • aromatic bisphosphites are used as ligands, as described, for example, in EP 0 213 639.
  • the second reaction step of the process according to the invention is the
  • the reaction product of the first stage consists after separation of the unreacted hydrocarbons from n-pentanal (valeraldehyde), 2-methylbutanal and small amounts of n-pentanol and 2-methylbutanol. If the feed hydrocarbon mixture contains isobutene, the first stage reaction mixture contains 3-methylbutanal.
  • the aldehyde fraction contains at least 85% by mass of n-pentanal, less than
  • Isomer composition in Aldolmaschines desired, it can be obtained for example via a distillation step upstream of the aldolization. In the distillation, n-valeraldehyde and 2-methylbutanal are separated according to the desired composition. If necessary, it can also be distilled sharper and the composition through
  • hydroxides, bicarbonates, carbonates, carboxylates or their mixtures in the form of their alkali metal or alkaline earth metal compounds or tertiary amines can be used in each case as aqueous solutions.
  • alkali metal alkalis such as, for example, are preferred
  • the concentration of the basic catalyst in the aqueous catalyst solution is generally between 0.1 and 10% by mass, in particular between 0.1 and y
  • Educt phase can vary within wide limits. If a tubular reactor is used in the process according to the invention, mass ratios of organic to catalyst phase of at least 1 to 2, preferably greater than 1 to 10, are suitable. The same applies to the use of stirred tanks.
  • the temperature of the reaction mixture at the reactor outlet is suitably above the boiling point of the aqueous catalyst solution between 80 0 C and 180 0 C, in particular between 120 and 150 0 C.
  • the pressure in the reaction device is due to the vapor pressures of the components in the reaction mixture at the appropriate temperatures.
  • the aldol condensation according to the invention is preferably carried out between 0.1 and 2.0 MPa, more preferably between 0.2 and 0.5 MPa.
  • the reaction apparatus of the aldol condensation can be at least one stirred tank or a stirred tank cascade or at least one tubular reactor or
  • the aldol condensation of the C 5 -aldehydes is preferably carried out in a tube reactor filled with static mixers, as described, for example, in DE 10 2009 001594.9.
  • the reaction mixture leaving the reaction mixture is separated into the catalyst phase and the organic product phase.
  • the reaction mixture leaving the reactor is poured into a
  • Short-distillation apparatus relaxed, preferably at atmospheric pressure. With high-boiling starting materials, it is possible to relax in a slight vacuum (0.01 to 0.1 MPa).
  • the short distillation can be flash distillation, as distillation in a
  • Falling film evaporator be carried out as a distillation in a thin-film evaporator or as a distillation in a combined falling film / thin film evaporator.
  • the flash distillation described below represents the preferred because technically simplest variant dar.
  • the short distillation is the
  • Comparable distillations have residence times of over 5 minutes.
  • the short distillation, especially the flash is preferably made adiabatic, thereby the
  • the reaction product is largely in a
  • Overhead product comprising water and C 5 aldehydes, and a bottom product comprising aldol condensation products, mainly decenals, and aqueous catalyst phase, separated.
  • the top product optionally contains other low boilers (eg pentanols) and small amounts of ⁇ , ⁇ -unsaturated aldehydes (decenals).
  • the bottom product contains, in addition to the mixture of decenals and catalyst phase, optionally higher condensation products, products from the Cannizarro reaction of the starting materials and small amounts of starting materials.
  • the preferably uncooled bottoms product from the short distillation can in a settling tank into an organic phase (product phase) and an aqueous phase, d. H. the aqueous catalyst phase are separated.
  • the organic product phase after leaching of traces of catalyst with water, preferably using the aqueous phase of
  • Crude product can be used directly for further in the third reaction stage, namely the selective hydrogenation.
  • high boilers high aldol addition and aldol condensation products
  • the aqueous catalyst phase is, if appropriate, together with the resulting wash water, returned to the aldol condensation reaction. From the catalyst phase can be discharged to keep the by-product level constant a small part and by an equivalent amount of
  • the overhead product of the short distillation is at a temperature which is below the boiling point of the water as well as below a minimum azeotrope, condensed.
  • the result is a liquid mixture which can be separated into an organic phase and an aqueous phase.
  • the organic phase of the top product is optionally pumped back into the aldol condensation reactor, optionally a part is discharged.
  • a portion of the aqueous lower phase may, for. B. for the washing of the product phase, as already mentioned above, are used.
  • the other part of the aqueous phase of the top product or the entire aqueous phase is used to discharge the water of reaction.
  • organic substances, especially educt, are still dissolved.
  • the wastewater can be added directly to the sewage treatment plant or after pre-treatment.
  • the pre-cleaning can be carried out by steam stripping or by azeotropic distillation of organic substances.
  • Aldol condensation product 2-propylheptalene If 2-methylbutanal is present in C 5 -aldehyde, 2-propyl-4-methylhex-2-enal is formed by crossed aldol condensation. If 3-methylbutanal in the C 5 aldehyde mixture is also present, the following unsaturated aldehydes can be formed as further primary aldol condensation products: 2-isopropyl-5-methylhex-2-enal, isopropyl 4-methylhex-2-enal, 2-propyl 5-methylhex-2-enal and 2-isopropyl-hept-2-enal. According to the invention, the proportion of 2-propylhept-2-enal based on the sum of all decenals is more than 90% by mass.
  • the crude aldol condensation product which in addition to the decenals mainly contains higher aldol condensates, can be purified before the next step, for example by distillation. Preference is given to using crude decene mixtures in the third stage, selective hydrogenation. ⁇
  • catalysts for selective hydrogenation, in which only the olefinic double bond is hydrogenated in decenal, catalysts are used, which may contain palladium, platinum, rhodium and / or nickel as hydrogenation-active component.
  • the metals can be used in pure form, as compounds with oxygen or as alloys.
  • Preferred catalysts are those in which the hydrogenation-active metal is supported on a support. Suitable carrier materials are
  • Alumina, magnesia, silica, titania and their mixed oxides, and activated carbon are particularly preferred.
  • Catalysts palladium on activated carbon and palladium on alumina Catalysts palladium on activated carbon and palladium on alumina.
  • Palladium content 0.1 to 5 mass%, preferably 0.2 to 1 mass%.
  • a catalyst consisting of aluminum oxide, preferably ⁇ -aluminum oxide with a Pd content of 0.3 to 0.7% by mass.
  • the catalyst may optionally contain moderating substances,
  • alkali components such as sodium compounds in concentrations up to 3% by mass.
  • the hydrogenation can be carried out continuously or discontinuously and both in the gas phase and in the liquid phase. Hydrogenation in the liquid phase is preferred because the gas phase process requires more energy because of the necessary circulation of large volumes of gas. For continuous liquid phase hydrogenation can be carried out continuously or discontinuously and both in the gas phase and in the liquid phase. Hydrogenation in the liquid phase is preferred because the gas phase process requires more energy because of the necessary circulation of large volumes of gas. For continuous liquid phase hydrogenation can be carried out continuously or discontinuously and both in the gas phase and in the liquid phase. Hydrogenation in the liquid phase is preferred because the gas phase process requires more energy because of the necessary circulation of large volumes of gas. For continuous liquid phase hydrogenation can be carried out continuously or discontinuously and both in the gas phase and in the liquid phase. Hydrogenation in the liquid phase is preferred because the gas phase process requires more energy because of the necessary circulation of large volumes of gas. For continuous liquid phase hydrogenation can be carried out continuously or discontinuously and both in the gas phase and in the liquid phase. Hydrogenation in the liquid phase is preferred because the gas phase process requires
  • the reactors are preferably high
  • a hydrogenation process for the production of decanals is, for example, the liquid-phase hydrogenation in two or more reactors, all of which are product-recycle, as described in US 5,831,135.
  • 2-Propylheptanal preferably at temperatures between 120 and 180 0 C, in particular between 140 and 160 0 C and a pressure of 1, 5 to 5 MPa, in particular at 2 to 3 MPa performed.
  • the hydrogenation product contains small amounts of decanols formed by overhydrogenation, small amounts of C 5 aldehydes and C 5 alcohols and high boilers, mainly higher ones
  • Hydheraustrag From the crude Hydheraustrag can be separated before the next reaction step, the oxidation, high boilers and / or low boilers. Preferably, a distillative workup is omitted.
  • the oxidation of the decanal mixture to the corresponding mixture of isomeric carboxylic acids can in principle be carried out in a manner known per se.
  • Oxidizing agents can be used oxygen, air or other oxygen-containing gas mixtures.
  • the oxidation can be carried out uncatalyzed or catalyzed. In the latter case, transition metal compounds, especially cobalt and manganese compounds, are used as the catalyst.
  • the oxidation can be carried out at atmospheric pressure or elevated pressure become.
  • the process of the invention, the oxidation is carried out without a catalyst and without further stabilizing additives.
  • the following examples are intended to illustrate the invention.
  • the crude product output from the n-valeraldehyde aldolization has the following composition in mass%, according to a GC analysis: 4.93%
  • n-Valeraldehyde 0.47% 2-methylbutanol, 0.30% pentanol, 0.51% 2-propyl-4-methyl-hexenal, 91, 81% 2-propylheptenal, and 1.98% residue.
  • Circuit apparatus selectively hydrogenated in the liquid phase on the palladium catalyst H 14535 (0.5% Pd on alumina), obtained from the company. Degussa, at 160 0 C and 2.5 MPa to 2-propylheptanal. For this purpose, 200 ml / h starting material continuously over 400 ml of catalyst, corresponding to a catalyst loading of 0.5 h "1 , passed.
  • reaction batch 5050 g of liquid educt were initially charged in the reactor.
  • a nitrogen-oxygen mixture was used, which was evenly distributed in the lower part of the reactor via a frit into the liquid.
  • the reactor were a constant nitrogen flow of 30 Nl / h and depending on the consumption by the reaction via an online measurement of the
  • Oxygen content in the exhaust regulated oxygen flow metered In the gas space of the reactor in the upper part of the reactor, a constant nitrogen flow of 330 Nl / h was metered. A maximum oxygen content in the exhaust gas of 6% by volume was permitted. The oxidation of the Cio-aldehyde mixture was at M
  • Cio-aldehyde mixtures to corresponding Cio-carboxylic acid carried out without catalyst.
  • results of the comparative oxidation of 2-propylheptanal in the presence of Cu and Mn salts as
  • composition of the product mixture determined by GC analysis.

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

Abstract

L'invention concerne un procédé de préparation d'un mélange d'acides décane-carboxyliques isomères, comportant les étapes suivantes: a) hydroformylation d'un mélange d'hydrocarbures contenant des C4-oléfines linéaires, au moyen d'un système catalytique contenant du rhodium; b) condensation aldolique d'un mélange de C5-aldéhydes aliphatiques obtenus à l'étape a); c) hydrogénation sélective du mélange de C10-aldéhydes insaturés obtenus à l'étape b) en C10-aldéhydes aliphatiques; et d) oxydation non-catalysée du mélange de C10-aldéhydes aliphatiques de l'étape c) de manière à obtenir un mélange ayant une teneur d'au moins 70 % en poids d'acide propylheptanoïque par rapport à la teneur totale en acides décane-carboxyliques isomères
EP10722067A 2009-07-23 2010-05-25 Procédé de préparation d'acides décane-carboxyliques Withdrawn EP2456745A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102009027978A DE102009027978A1 (de) 2009-07-23 2009-07-23 Verfahren zur Herstellung von Decancarbonsäuren
PCT/EP2010/057157 WO2011009657A2 (fr) 2009-07-23 2010-05-25 Procédé de préparation d'acides décane-carboxyliques

Publications (1)

Publication Number Publication Date
EP2456745A2 true EP2456745A2 (fr) 2012-05-30

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US (1) US8907129B2 (fr)
EP (1) EP2456745A2 (fr)
JP (1) JP5787886B2 (fr)
KR (1) KR20120038514A (fr)
CN (1) CN102548946A (fr)
BR (1) BR112012001274A2 (fr)
CA (1) CA2768604A1 (fr)
DE (1) DE102009027978A1 (fr)
MX (1) MX2012000840A (fr)
SG (1) SG178071A1 (fr)
TW (1) TW201125845A (fr)
WO (1) WO2011009657A2 (fr)
ZA (1) ZA201201237B (fr)

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DE102013020322B4 (de) 2013-12-05 2019-04-18 Oxea Gmbh Verfahren zur Gewinnung von 2-Methylbutanal aus den bei der Herstellung von Gemischen isomerer a,ß-ungesättigter Decenale anfallenden Nebenströmen
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KR20120038514A (ko) 2012-04-23
JP5787886B2 (ja) 2015-09-30
CN102548946A (zh) 2012-07-04
TW201125845A (en) 2011-08-01
ZA201201237B (en) 2012-10-31
BR112012001274A2 (pt) 2016-02-10
US20120172624A1 (en) 2012-07-05
MX2012000840A (es) 2012-02-28
DE102009027978A1 (de) 2011-01-27
JP2012533589A (ja) 2012-12-27
SG178071A1 (en) 2012-03-29
WO2011009657A3 (fr) 2011-04-21
CA2768604A1 (fr) 2011-01-27
US8907129B2 (en) 2014-12-09

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