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WO2019091792A1 - Procédé de production de méthylisobutylcétone - Google Patents

Procédé de production de méthylisobutylcétone Download PDF

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Publication number
WO2019091792A1
WO2019091792A1 PCT/EP2018/079295 EP2018079295W WO2019091792A1 WO 2019091792 A1 WO2019091792 A1 WO 2019091792A1 EP 2018079295 W EP2018079295 W EP 2018079295W WO 2019091792 A1 WO2019091792 A1 WO 2019091792A1
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WO
WIPO (PCT)
Prior art keywords
acetone
separation device
distillation column
liquid
stream
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.)
Ceased
Application number
PCT/EP2018/079295
Other languages
German (de)
English (en)
Inventor
Thomas Streich
Harald KÖMPEL
Jin GENG
Johanna Schmeinck
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.)
ThyssenKrupp AG
ThyssenKrupp Industrial Solutions AG
Original Assignee
ThyssenKrupp AG
ThyssenKrupp Industrial Solutions 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 ThyssenKrupp AG, ThyssenKrupp Industrial Solutions AG filed Critical ThyssenKrupp AG
Priority to EP18793641.4A priority Critical patent/EP3707119A1/fr
Publication of WO2019091792A1 publication Critical patent/WO2019091792A1/fr
Anticipated expiration legal-status Critical
Ceased 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
    • C07C45/73—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 hydrogenation
    • 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

Definitions

  • the present invention relates to a process for the preparation of methyl isobutyl ketone starting from acetone, wherein the process is carried out in one stage in a reactor section and a discharged from the reactor section crude product stream of methyl isobutyl ketone for treatment first at least a first distillation column is fed and the product from the bottom of this first distillation column Subsequently, a liquid-liquid separation device is supplied in which water is separated from an organic phase, wherein the water phase from the liquid-liquid separation device is fed to at least one further separation device in which a portion of the acetone contained in the water phase from the process stream is separated.
  • MIBK methyl isobutyl ketone
  • DAA diacetone alcohol
  • MSO mesityl oxide
  • a hydrogenation of mesityl oxide to methyl isobutyl ketone combines all three reaction steps in a single reactor (so-called "one-step synthesis") with a palladium-loaded ion exchange resin as a bifunctional catalyst.
  • MIBK recovered product
  • US Pat. No. 3,574,763 A describes a process for the preparation of methyl isobutyl ketone in which acetone reacts with hydrogen on a palladium-doped acidic cation exchange resin in a one-stage process. In this process, a yield of methyl isobutyl ketone of about 34% to 37% is obtained.
  • WO 2007/069109 A2 discloses a one-stage process for the preparation of methyl isobutyl ketone in which the crude product is purified in a first distillation in which acetone is recovered.
  • the bottom product from the first distillation is fed to a liquid-liquid separator in which an organic phase is separated, which is then introduced into the upper region of a second distillation column.
  • the resulting top product is condensed and is fed to the liquid-liquid separator.
  • the methyl isobutyl ketone-containing bottom product is withdrawn from the second distillation column.
  • This bottom product is fed to a third distillation column, are withdrawn from the high-boiling impurities as the bottom product and also purified MIBK is recovered.
  • MIBK purified MIBK
  • the water contains up to 8% by weight of organic components (MIBK, acetone, alcohol) and pollutes the wastewater treatment plant. 2. Valuable components (MIBK, acetone, alcohol) can not be recycled.
  • the residual acetone content in the decanter can be reduced by changing the operating conditions of the upstream column (acetone column), which, however, leads to a higher energy consumption and an increasing acetone loss in the by-product stream (stream 24 in the Figure 1 below), which is deducted from the head of this column.
  • the total loss of acetone in the by-product stream and in the wastewater stream) can not be significantly reduced by changing the operating conditions of the acetone column.
  • US Pat. No. 6,518,462 B2 discloses a process for the preparation of methyl isobutyl ketone from acetone which is carried out in several separate stages, the acetone first being converted into mesityl oxide in one column to give diacetone alcohol and further by-products. In a second reactor then mesityl oxide is reacted with hydrogen to methyl isobutyl ketone. H 2 is first separated from the product stream and discharged from the process, and the product stream containing the methyl isobutyl ketone (MIBK) is fed to a distillation column in which methyl isobutylcarbinol (MIBC) is separated from the product stream. It should be noted that the separation of MIBK and MIBC is difficult.
  • MIBK methyl isobutylcarbinol
  • the MIBC accumulates in the bottom of this distillation column while methyl isobutyl ketone is withdrawn as a side stream. From the top of this distillation column, an azeotropic mixture of water and MIBK is withdrawn, which is then condensed and separated in a decanter into an organic and an aqueous phase. The aqueous phase is passed to a second decanter whose aqueous phase is fed to a distillation column from which purified water is removed. The top product from this distillation column contains mesityl oxide and water and can be recycled to the second reaction stage of the process in which the production of methyl isobutyl ketone from mesityl oxide occurs.
  • the organic phase is prepared by distillation, wherein in addition to the product and acetone can be recovered by distillation from the organic phase and recycled as Recyclierstrom in the reaction.
  • a disadvantage of this method also that in the reaction in addition to the 6-methylheptanone as a by-product and methyl isobutyl ketone is formed, which must be separated from the product in the distillation of the organic phase.
  • the object of the present invention is to provide an improved one-step process for the production of methyl isobutyl ketone from acetone, which makes it possible to reduce acetone loss.
  • the water phase of the liquid-liquid separation device is fed to at least one further separation device in which a portion of the acetone contained in the aqueous phase is separated from the process stream.
  • the invention provides at least one further work-up step in this further separation device by which it is possible to recover acetone from the wastewater stream.
  • the total acetone loss via wastewater and low-boiling by-products can be reduced to well below 2% by weight, preferably to below 1.5% by weight, more preferably for example to about 1.2 to 1.3% by weight -%.
  • a wastewater stream with better compatibility for biological water treatment due to a significantly reduced hydrocarbon content in the wastewater stream.
  • the acetone-rich stream obtained by separation in the further separation device is recycled to the process of processing the crude product stream. This makes it possible to reduce the acetone used as starting material in the process.
  • the acetone is a low-boiling component compared with water and, if appropriate, other organic components in the wastewater stream, it is advantageous according to a preferred variant of the process according to the invention if the acetone is recovered in the head region of the further separating device.
  • the further separation device according to the invention is therefore preferably designed so that a purified water stream is obtained as the bottom product from this.
  • acetone recovered from wastewater in the further separation device can be returned to the process.
  • a preferred variant of the process according to the invention provides that the acetone-rich stream obtained in the further separation apparatus is recycled to the first distillation column or to a line leaving this first distillation column for an acetone recycle to the reactor and then the subsequent further separation steps again passes.
  • the recycling of the acetone can be carried out, for example, in a recycle line for acetone separated in the first distillation column and thus combined with the acetone stream separated there and returned to the reactor.
  • a third process stream is discharged as side stream from the further separation apparatus in addition to the acetone-rich stream, which is discharged in the head area and water, which is discharged from the sump, which apart from small proportions acetone of acetone contains organic components.
  • This variant thus provides for a separation of the water phase supplied to the further separation device into three further fluid streams, wherein the said side stream may be recycled with the organic components other than acetone to an earlier separation step and / or be processed in further subsequent separation processes.
  • a preferred variant of the method according to the invention provides that the further separation device is a fractionating device.
  • a fractionation takes place in the further separation apparatus, in which the acetone is obtained as a light fraction and the side stream discharged from the further separation apparatus is a middle fraction of the Fractionation is.
  • This middle fraction with organic components other than acetone can be utilized, for example, as a solvent mixture or as a liquid fuel.
  • This middle fraction may contain a proportion of, for example, up to 70% by weight, preferably up to 80% by weight, for example up to 85% by weight, of organic components.
  • a stream of more than 80% by weight, preferably more than 90% by weight, of acetone can be produced and recycled back into the reaction section.
  • the upstream first distillation column can be operated with relatively little separation effort and little acetone loss in the top product of the column.
  • the further separation device comprises a dividing wall column, a two-column system, a multi-column system or a distillation column with side draw.
  • a preferred further development of the method according to the invention provides that the organic phase from the liquid-liquid separation apparatus which contains methyl isobutyl ketone is subsequently fed to at least one second distillation column for further purification of the product stream.
  • the product stream withdrawn in the head region of this second distillation column can be returned to the liquid-liquid separation device or else directly further into the separation device according to the invention.
  • the liquid-liquid separation device is in particular a decanter.
  • the bottom product from the second distillation column contains the methyl isobutyl ketone and optionally high-boiling organic impurities and can be further processed and purified in subsequent process steps.
  • the product stream withdrawn from the bottom of the second distillation column can then be fed to a third distillation column in which separation of the high-boiling organic impurities is carried out, the latter being discharged from the bottom of the third distillation column and the lower-boiling purified methyl isobutyl ketone in the top region or as Obtain side stream from this third distillation column and can supply, for example, a tank or the like.
  • the single-stage reaction of acetone to methyl isobutyl ketone is a catalytic process
  • a preferred development of the invention provides that in this process the aging of the catalyst and the associated decreasing catalyst activity with respect to the conversion of acetone to methyl isobutyl ketone is determined and depending on this activity of the catalyst each optimized operating condition is determined and adjusted with the least possible loss of acetone.
  • This variant of the method according to the invention makes it possible to carry out a process optimization in this way.
  • the present invention furthermore relates to a plant for the preparation of methyl isobutyl ketone from acetone
  • a plant for the preparation of methyl isobutyl ketone from acetone comprising at least one reactor whose outlet line is in communication with at least one first distillation column in which acetone is separated from a crude methylisobutyl ketone-containing crude product stream obtained in the bottom of the first distillation column; Sump of this first distillation column is in operative connection with a liquid-liquid separator, suitable to separate water from an organic phase, wherein according to the invention, the water phase from the liquid-liquid separator laxative line is in operative connection with at least one further separation device, suitable, a Separate acetone-rich stream from the water phase.
  • the system according to the invention further provides that at least one return line originating from the top section of the further separating device is returned from the further separating device to the first distillation column or into a line which leads back to the first distillation column in the upper region.
  • acetone recovered from the water phase in the further separation apparatus can be recycled to the treatment process and ultimately also to the production process, for example if the acetone recovered in the top section of the first distillation column is returned to the reactor in which methyl acetobutyl ketone is catalytically produced from the acetone ,
  • Purified wastewater accumulates in the sump area of the further separation device and can be removed via a line emerging from the sump area of the further separation device.
  • a further line emerging from the further separating device in a side area is provided, by means of which a third process stream is removed as a side stream from the further separating device, which contains, in addition to small amounts of acetone of acetone, various organic components.
  • organic components can be supplied for further use and used, for example, as a solvent mixture or as a liquid fuel.
  • the organic phase including the methyl isobutyl ketone from the liquid-liquid separator laxative line is provided which leads from the liquid-liquid separator to a second distillation column.
  • a further treatment of the crude product stream can be carried out, which contains the methyl isobutyl ketone.
  • Lower boiling constituents can be recycled from the top section of the second distillation column via a line to the liquid-liquid separation device or to the further separation device according to the invention.
  • the product stream from the bottom of the second distillation column can be fed via a line to a third distillation column in which high-boiling organic components are separated from the product stream, which can then be removed from the bottom of this third distillation column via a line.
  • the purified methyl isobutyl ketone can be removed, for example, as a side stream from the third distillation column via a product line.
  • Figure 1 is a schematically simplified system diagram of a plant according to the invention for the production of methyl isobutyl ketone from acetone;
  • FIG. 1 a shows a slightly modified plant diagram relating to an exemplary variant of a plant for the production of methyl isobutyl ketone from acetone;
  • FIG. 1 b is a slightly modified plant diagram relating to a further exemplary variant of a plant for the production of methyl isobutyl ketone from acetone;
  • Figure 2 is a graph of the acetone loss in the various process streams depending on the operating conditions using the other waste stream separation apparatus of the present invention
  • FIG. 3 shows an exemplary embodiment of a further separating device according to the present invention
  • Figure 4 shows an alternative exemplary embodiment of another separation device according to the present invention
  • Figure 5 shows an alternative exemplary embodiment of another separation device according to the present invention.
  • FIG. 1 Via a first feed line 10, which passes at least one heat exchanger 1 1, acetone is fed to the inlet line 12, which feeds the educt stream to a reactor 13. Hydrogen is supplied from a tank 14 to the reactor via a second feed line 15, with the first feed line 10 opening into the second feed line 15, so that the two educt streams of acetone and hydrogen are combined and fed together to the reactor 13 via the input line 12.
  • an outlet line 16 passes through the heat exchanger 1 1, so that the product stream from the reactor 13, which was heated by the reaction in the reactor 13, undergoes a heat exchange with the acetone stream in the educt line 10 and preheats the acetone.
  • Product gas mixture the reactor 13 and is first fed to a separator 17, in which a separation of hydrogen takes place, which then passes through a first line 18, a heat exchanger 19 and then via a return line 20 and a Compressor 21 or a pump can be returned to the hydrogen tank 14 and used again in the manufacturing process as a reactant.
  • a partial flow of hydrogen can be diverted from the return line 20 and removed.
  • the product mixture obtained after the separation of hydrogen is fed via a line 22 to a first distillation column 23 in which on the one hand low-boiling components in the top region of the distillation column 23 can be separated and removed via a line 24.
  • this first distillation column 23 also acetone is separated from the product mixture and recycled via a return line 25, which emanates from the upper portion of the first distillation column 23, to the inlet line 10 for acetone, so that the acetone separated here used again in the manufacturing process and the Reactor 13 can be supplied.
  • the product stream 26 which is largely freed from the low-boiling components and which also contains the methyl isobutyl ketone, is fed to a liquid-liquid separator 27 via a product line 26.
  • This liquid-liquid separation device 27 may, for example, be a decanter in which a separation of an aqueous phase from an organic phase takes place.
  • the organic phase from this liquid-liquid separation device 27 is fed via a product line 28 to a second distillation column 29.
  • this second distillation column 29 a mixture of lower-boiling components is obtained in the top region, which contains in particular acetone, 2-propanol, water and optionally some methyl isobutyl ketone as a heterogeneous azeotropic mixture and via line 30 to the liquid-liquid separator or to the invention further Separating device 35 can be returned.
  • the product stream is obtained, which contains mainly methyl isobutyl ketone and higher-boiling by-products. This product stream can be passed via the outgoing from the bottom of the second distillation column line 31 to a third distillation column 32.
  • This third distillation column 32 From the bottom of this third distillation column 32 separated high-boiling impurities can be removed via line 33 from the system.
  • the purified methyl isobutyl ketone is discharged as product stream via line 34 from the third distillation column and, for example, transferred to a tank for storage or fed to further processing.
  • a further separation device 35 is now provided, into which the water phase accumulating in the liquid-liquid separation device 27 is transferred via the line 36 coming from this liquid-liquid separation device 27.
  • this further separation device 35 can be a treatment and separation of the water phase the liquid-liquid separation device 27 is carried out, being separated from the wastewater in the further separation device 35 for an acetone, which is obtained in the head region of the further separation device 35 and can be recycled via the return line 37 to the first distillation column 23.
  • the recirculation can, for example, as shown in Figure 1 can be seen such that the coming of the further separation device 35 return line 37 opens into the coming of the first distillation column 23 return line 25 in the flow path to the first distillation column 23, so that the obtained from the wastewater acetone with the acetone separated in the first distillation column 23 can be returned via line 25 to the educt line 10, in order then to supply this acetone again to the production process in the reactor 13.
  • this further separation device 35 By using this further separation device 35, the loss of acetone via the wastewater can thus be greatly reduced.
  • a middle fraction is removed as side stream, which contains various organic components other than acetone and can be removed from the system via line 38 and, if appropriate, fed to a further use.
  • This middle fraction can subsequently be used, for example, as a solvent mixture or liquid fuel.
  • a purified water phase is obtained, which at best still contains a very small proportion of organic constituents and can be removed from the system via the line 39 emerging from the bottom of the further separating device 35.
  • FIG. 1 a shows a variant of the system which is slightly modified compared to the embodiment of FIG.
  • the stream coming from the further separation device 35 is returned via the return line 37 directly into the distillation column 23 and not into the return line 25.
  • the plant parts and the process sequences are as described above in FIG.
  • FIG. 1 b a further compared to the embodiment of Figure 1 slightly modified variant of the system is shown.
  • the stream coming from the second distillation column 29 via the return line 30 is not passed into the liquid-liquid separation device 27, but into the further separation device (column) 35.
  • the plant parts and the process sequences are the same as in FIG. 1 described.
  • FIG. 2 is a graph of acetone loss in the various process streams depending on the Operating conditions when using the further separation device for the wastewater stream according to the present invention shows.
  • the ordinate indicates the acetone loss in the total process in% by weight.
  • a total of three curves are shown, a lower curve, a middle curve and an upper curve.
  • the lower curve represents the acetone loss in the wastewater
  • the middle curve the acetone loss over the light by-products
  • the upper curve represents the sum of the respective values of the other two curves, ie the upper curve corresponds to the total loss of acetone in the manufacturing process.
  • the abscissa indicates the change in the operating conditions at which the loss of acetone via the waste water or the loss of acetone can be controlled by the light by-products.
  • These variable operating conditions during operation of the system according to the invention include, for example, the bottom temperature and the reflux ratio of the first distillation column 23.
  • the residual acetone content in the waste water of the liquid-liquid separation device 27 can be reduced by changing the operating conditions of the first distillation column 23, which is connected upstream of the liquid-liquid separation device.
  • the total loss of acetone in the by-product stream 24 and in the waste water stream of the liquid-liquid separator 27
  • the further separation device comprises a two-column system.
  • a first column 35 a of the further separation device is fed via the line 36, which comes from the liquid-liquid separator 27, not shown here, a wastewater stream having a hydrocarbon content of, for example, 3 to 7 wt .-%.
  • a wastewater stream having a hydrocarbon content of, for example, 3 to 7 wt .-% In the top of this first column 35 a is a process stream with the lower-boiling organic components, which were contained in the supplied wastewater stream.
  • the further separation device comprises a
  • Separating device is connected via the line 36, the liquid-liquid from the not shown here.
  • a wastewater stream having a hydrocarbon content of, for example, 3 to 7 wt .-% fed In the top of this column 35 acetone accumulates, which via the return line 37 to the first not shown here Distillation column (see Figure 1) can be returned. In the bottom of the column 35, a purified waste water stream having a hydrocarbon content of, for example, less than 0.1 wt .-% is obtained and can be removed via line 39 from the system. As a side stream falls in the column 35, a middle fraction with the other organic components which were contained in the supplied wastewater stream and separated from the acetone on the one hand and the water phase on the other hand in the column 35. These organic components obtained as the middle fraction can be removed via the line 38 and fed to a further use, for example as a solvent mixture or as a liquid fuel.
  • the further separation device comprises a system with only one column, which is designed as a dividing wall column with an example vertical partition 35 c, wherein the partition wall 35 c is shown in Figure 5 only schematically.
  • This vertical partition divides the cross section of the column 35 into two sections. Above the partition 35 c, a liquid phase is collected and distributed in a selectable ratio to the two column cross-sections.
  • This column 35 of the further separation device is fed via the line 36, which comes from the liquid-liquid separation device 27, not shown here, a wastewater stream having a hydrocarbon content of, for example, 3 to 7 wt .-%. In the top of this column 35 falls to acetone, which over the

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

La présente invention concerne un procédé pour produire de la méthylisobutylcétone à partir d'acétone. Un courant de produit brut de méthylisobutylcétone est acheminé pour la préparation d'abord d'au moins une première colonne de distillation (23) et le produit est acheminé depuis le pied de ladite première colonne de distillation (23) après un dispositif de séparation liquide-liquide (27), séparé dans l'eau à partir d'une phase organique, selon l'invention, la phase aqueuse du dispositif de séparation liquide-liquide (27) étant acheminée au moins vers un autre dispositif de séparation (35), et la ou les fractions d'acétone contenue dans la phase aqueuse étant séparées du courant de traitement. Par l'intermédiaire de l'autre étape de traitement dans ledit autre dispositif de séparation (35), il est possible de recueillir de l'acétone à partir du courant résiduaire. Cela donne lieu à une optimisation du processus pour la production de méthylisobutylcétone permettant de réduire les pertes d'acétone.
PCT/EP2018/079295 2017-11-07 2018-10-25 Procédé de production de méthylisobutylcétone Ceased WO2019091792A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP18793641.4A EP3707119A1 (fr) 2017-11-07 2018-10-25 Procédé de production de méthylisobutylcétone

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102017219762.5 2017-11-07
DE102017219762.5A DE102017219762A1 (de) 2017-11-07 2017-11-07 Verfahren zur Herstellung von Methylisobutylketon

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WO2019091792A1 true WO2019091792A1 (fr) 2019-05-16

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3574763A (en) 1966-07-07 1971-04-13 Johannes Wollner Production of saturated carbonyl compounds
WO2002022542A1 (fr) * 2000-09-15 2002-03-21 Catalytic Distillation Technologies Procede de production de methylisobutyl-cetone par mise en oeuvre d'une technique de distillation catalytique
DE10112099A1 (de) 2001-03-14 2002-09-19 Degussa Verbessertes Verfahren zur Herstellung von 6-Methylheptanon
WO2007069109A2 (fr) 2005-12-14 2007-06-21 Sasol Technology (Pty) Limited Procede et appareil de production de methylisobutylcetone purifie

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3547763A (en) 1967-06-05 1970-12-15 Du Pont Bicomponent acrylic fiber having modified helical crimp

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3574763A (en) 1966-07-07 1971-04-13 Johannes Wollner Production of saturated carbonyl compounds
WO2002022542A1 (fr) * 2000-09-15 2002-03-21 Catalytic Distillation Technologies Procede de production de methylisobutyl-cetone par mise en oeuvre d'une technique de distillation catalytique
US6518462B2 (en) 2000-09-15 2003-02-11 Catalytic Distillation Technologies Process for production of MIBK using CD technology
DE10112099A1 (de) 2001-03-14 2002-09-19 Degussa Verbessertes Verfahren zur Herstellung von 6-Methylheptanon
WO2007069109A2 (fr) 2005-12-14 2007-06-21 Sasol Technology (Pty) Limited Procede et appareil de production de methylisobutylcetone purifie

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EP3707119A1 (fr) 2020-09-16

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