US2399976A - Production of isophorone and related products - Google Patents

Production of isophorone and related products Download PDF

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Publication number
US2399976A
US2399976A US474060A US47406043A US2399976A US 2399976 A US2399976 A US 2399976A US 474060 A US474060 A US 474060A US 47406043 A US47406043 A US 47406043A US 2399976 A US2399976 A US 2399976A
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water
isophorone
acetone
reaction
ketone
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Seaver A Ballard
Vernon E Haury
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Shell Development Co
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Shell Development Co
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Priority to US474060A priority Critical patent/US2399976A/en
Priority to GB60/44A priority patent/GB583863A/en
Priority to FR941124D priority patent/FR941124A/fr
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Publication of US2399976A publication Critical patent/US2399976A/en
Priority to DEN1889A priority patent/DE840842C/de
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    • 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

Definitions

  • This invention relates to a process for the production oi isophorone and related products. More particularly, the invention pertains to a method of manufacture wherein s. saturated ketone of trom Zi to carbon atoms undergoes condensation with cycliation in the presence of a dilute adueous solution of an alkali metal hydroxide to produce an unsaturated alicarbocyclic ketone like isophorone or homo-isophorones.
  • Another object is to provide a process yfor producing isophorone or homodsophorones from saturated ltetones containing between 3 and 5 can bon atoms.
  • a further object is to provide a process wherein a saturated ketone containing from 3 to 5 caroon atoms is effectively cyclized to isophorone or homo-isophcrones While the non-cycllc isomers oi the same number ai carbon atoms or higher condensation products than the primary unsaturated alicarbocyclic ketone product are formed in only small amounts.
  • An additional object is .to provide amethod of manufacture of isophorone and certain h'omoisonhoroncs which permits' the catalyst to be maintained at substantially initial activity without deterioration over very long periods of time.
  • l1l'he primary object of the invention is to provide a process for the manufacture of isophorone whichis highly eiiicient and economical.
  • the treatment of acetone with a condensation catalyst causes a number of condensation reactions to occur-i. e., the treatment does not resultV in a single and unique reaction of condensation.
  • severe conditions oi treatment have been employed by the use oi' strong anhydrous alkaline substances or concentrated solutions of certain of them. While the formation of isophorone is realized with such catalysts, the use of these strong condensing agents causes the formation of high condensation products like high-boiling condensates, resinous Asubstances and even terry materials, in some instances.
  • the formation o! thehigh condensate lay-products is responsible i'or a maior loss of yield of the isophorone in the processes.
  • Water is one of the products of reaction in the The formation of each molecule of isophorone liberates two molecules of water.
  • the formed or liberated water of reaction caused the catalyst to soon become ineective or destroyed it and when a concentrated solution was employed, the formed water soon diluted the catalyst solution to an inoperative state under the conditions utilized.
  • sodamide, sodium alcoholate or calcium carbide the formed water reacts with the catalyst to destroy it.
  • acetone is condensed to isophorone in the presence of a dilute aqueoussolution of an alkali metal hydroxide when liquid acetone is brought into intimate contact with the catalyst solution at a temperature above about 130 C. and that the use of the dilute catalyst solution enables those ,high-boiling byproducts to be maintained at a low value.
  • a temperature above about 130 C. is considerably above the normal boiling temperature of acetone and the acetone is maintained in a liquid state by the use of sumcient pressure to prevent boiling of the reaction mixture.
  • the organic phase contains a preponderance of acetone therein, wateris appreciably soluble in this phase and by continuously withdrawing a part of the phase from the reaction zone, the water of reaction is removed therefrom.
  • the operation f the property of appreciably dissolving water and they are thus operative in the process.
  • the process of our invention comprises continuously introducing and commingling a. saturated ketone containing between 3 and 5 carbon atoms in the liquid state with a dilute aqueous solution of an alkali meal hydroxide, the reaction zone being maintained at a temperature preferably between 150 C. and 200 C. and under at least suiiicient pressure to prevent boiling therein, and continuously withdrawing a portion of the organic phase from the reaction zone, the concentration of hydroxide in dilute aqueous solution being maintained substantially constant by the water of reaction being carried out of the reaction zone with the efiiuent organic phase and, if more water than that formed in the reaction is extracted, by feeding the ,needed water into the reaction zone along with the input ketone.
  • the ketones employed as reactants in the process of the invention are acetone, methyl ethyl ketone, methyl propyl ketone, diethyl ketone and methyl isopropyl ketone and each of these open-chain saturated ketones possesses the required structure in having at least' Aone hydrogen atom (some have two and some -have three) linked directly to each alpha carbon atom.
  • - Acetone is a preferred reactant in that it is most reactive of the ketones, the others requiring, in general, higher reaction temperatures and longer times of residence in the reaction zone for best results.
  • the temperature maintained in the reaction zone is from about C. to the critical temperature of the ketone reactant. Since the desired reaction is effected in the liquid phase, the upper limit is determined by the critical temperature of the ketone employed as reactant. In the case of acetone, the critical temperature is about 235 C.; with methyl ethyl ketone, it is about 261 C.; and with methyl propyl ketone it is about 282 C.
  • the process is preferably executed at a temperature between C. and 200 C., excellent results being obtained with acetone in the neighborhood of C.
  • the pressure required to be maintained will vary with the particular operating temperature and the particular ketone reactant employed in the process. As is well-known. the pressure needed will be higher for higher operating temperatures, and since the materials in the reaction zone are kept entirely in the liquid phase in the process, although the operating temperature is above the normal boiling temperature of some constituents therein, the pressure employed is considerably above atmospheric pressure, and at least equal to the sum of the partial pressures assumo of each of the components present in the reaction zone. Ordinarily a pressure ot say 15 lbs. per square inch above the required minimum is maintained so as to satisfactorily prevent any boiling in the reaction zone which might occur, owing to even' minor iiuctuations of temperature in the executionof the process.
  • the catalyst is a dilute aqueous solution of an alkali metal hydroxide.
  • a dilute aqueous solution is meant one containing between 15 per cent and 35 per cent by weight of the alkali metal hydroxide with respect to the aqueous solution.
  • the dilute aqueous solution contains a weight ratio of water to alkali metal hydroxide between 5.66:l and 136:1. 1n the operation oi the process the concentration of hydroxide in aqueous solution is maintained substantially constant at a value within the indicated range.
  • the ability ci the organic phase to extract water is primarily a function of the amount of ketone reactant present in the organic phase, and this is determined by the time of residence of the ketone in the reaction zone.
  • the longer the time of residence in the reaction zone the lesser will be the amount of unreacted ketone in the organic phase, a portion of which is withdrawn continuously in an amountequal tothe material fed to the reactor.
  • the time of residence is' in timeunits and equal to the volume ci organic phase present in the reactor divided by the volume of ketone per unit time fed tothe reactor.
  • any alkali metal hydroxide is ,suitable for use in the aqueous catalyst phase.
  • sodium hydroxide is a preferred catalyst although lithium, rubidiurn, or cesium hydroxides are employed, if desired.
  • the most preferred catalyst is potassium hydroxide which, although somewhat more expensive than sodium hydroxide, has greater activity than the hydroxide of sodium. Since substantially no catalyst is consumed in the process in contradistinction to prior art methods requiring comparatively large requirements of catalyst, our method has practically no cost for catalyst other than the original price. The life of the catalyst solution appears to be indefinite and the only loss is a few hundredths of a per cent carried out with the efiluent organic phase.
  • the organic phase is intimately contacted or coxnmingledy with the aqueous catalyst phase.
  • Any means for churning and mixing the two phases is satisfactory.
  • a suitable reactor is a turbo mixer which is a closed vessel iitted with revolving paddles.
  • Another suitable means of obtaining the required agitation and turbulence is to pump, at preferably high velocity. the mixture of two phases through a time tank iitte'd with bailes, perforated plates or the like, the exit of the tank ⁇ connecting to the intake of the pump.
  • Figure 1 which gives a simple arrangement of suitable apparatus for executing the process.
  • Figure 2 shows a combination of more preferred equipment for operation of the process.
  • the liquid ketone reactant is pumped into the system by ketone i'eed pump I through pipe 2 to input control valve 3, entering the reactor which is' a turbo mixer having an internally rotating paddle wheel .and fitted with heating means such as an internal steam coil (not shown) through pipes Ili and l. If needed, water is pumped into the system by means of water feed pump 1, passing through pipe 8 to control valve 9 and into the 'reactor by means of pipes IU and i.
  • reactor 6 is iilled with the desired quantity oi' the dilute aqueous solution of an alkali metal hydroxide.
  • One-half of the volume of the reactor is filled with thedilute aqueous catalyst solution when the preferred ratio of one volume of organic phase to one volume of aqueous phase is used.
  • the reaction mixture of catalyst solution. unconverted ketone and products is withdrawn upwards from the reactor 8 through conduit It to combined cooler and separator I3 wherein the material is partially cooled and stratification ci" the organic phase and aqueous phase occurs.
  • the upper layer ⁇ in cooler and separator I3 is the organic phase; the lower layer being the' aqueous phase which returns to turbo mixer by means oi pipe I2. Liquid organic present in the eilluent organic phase fed to the' recovery system. In the case of condensation. v 4of acetone.
  • the major "constituent 4 will be unreacted acetone along with which will be mesityl oxide, diacetone alcohol, the desired isophorone, phorone and higher condensation products.
  • ketones containing 4 carbon atoms' or'5 vcarbon atomsare employed as reactants the constituents will be similar homologues and owing to the more complex structure of the 4 and 5 carbon atom ketones, isomers of particular constituents will be present. For example, in the conden-saf tion of lmethyl ethyl ketone. according to the Il which water is removed from the reaction zone -stereo and optical isomers.
  • That process enables the crude organic mixture to be treated so that products like mesityl oxide and diacetone alcohol are selectively reverted back to parent acetone without changing isophorone present in the'mixture.
  • the recoveredacetone obtained by any method can be returned as feed to the condensation process.
  • Those higher condensation products which are not revertible to the parent ketone -by al now known method or are not of particular value in themselves are obtained in minimum amount by the process of the invention,
  • Ketone reactant by means of pump 2l, pipe 22 and control valve 2l, is fed to feed tank 24 which is an intermediate storage vessel for feed Y' to the reaction system.
  • Water if needed, is supplied to tank 26 through pump 25, pipe 2l and control valve 2T.
  • the feed is withdrawn from tank 24 through line 28 to pump i@ which pumps the feed into the reaction and supplies the necessary pressure needed to keep the materials in 45 the reaction system in the liquid state and prevent boiling therein.
  • the feed is passed through pipe 8
  • the feed passes from heater 34 by pipe 35 which is tapped into pipe 40.
  • the reaction zene is a circulating system consisting of pipe le, circulation pump 4
  • the adueousphase is returned from separator l! by means of pipe 4E to pipe 40 in the suction side of pump 4I in the circulating system.
  • Valve 4l connected in' pipe 46 is used to control the levell of the phases in separator 4I.
  • the eiiiuent orsanic phase passesvfrom separator 45 through pipe Il to cooler 4l where the phase is cooled and from which the material passes through linell to a conventional pressure regulatingyalve l2 which controls the pressure on the system and is actuated through connection B3 tapped into pipe l of the circulating system.
  • the efiiuent organic layer is taken 'from valve 52 and runto the recovery systeminot shown). 'The recovery and separation of the products is done in the same manner as described in the. system of flow shown in Figure l.
  • the unit is a continuous evaporator wherein the caustic solution is concentrated and the concentrated solution then returned continuously into the reaction zone.
  • a continuous liquid phase extraction unit can be used in which' a liquid extractant like a butyl alcohol which will remove water and concentrate the caustici solution is suitable.
  • Another methcd which is effective in obtaining the desired result with the process is to increase the ability of the organic'phase to extract water from the aquebus phase in the system by continuously feeding in a lower alcohol such as methyl alcohol, ethyl alcohol, normal propyl alcohol or isopropyl alcohol into the reaction zone.
  • Such a substance is inert in the reaction zone, but greatly assists the organic phase to extract water from the aqueous phase' so that the concentration of hydroxide in the aqueous solution will remain constant and not become diluted by failure of the organic phase to extract or remove .”sufiicient water from the reaction zone.
  • the saturated ketone employed as reactant and *Y condensed to the mono-unsaturated alicarbocyclic ketone is ordinarily the sole reactant fed to the system in the process of the invention.
  • Mixed isomeric products are obtained by using a plurality of the individual saturated ketones containing 3 to 5 carbonzatoms.
  • Example I l.acetone was condensed continuously in the 5 presence of a dilute aqueous solution of sodium accanto hydroxide, the hydroxide concentration in aqueous solution being maintained at about 25 per cient throughout the run.
  • the lacetone was processed in apparatus similar to that shown in Figure 1.
  • Acetone was continuously introduced at a rate of about 840 ce. per hour along with 6o cc. per hour of water which maintained the caustic concentration constant.
  • Equal volumes of organic layer to catalyst layer were used in the reaction Vzone andthe temperature therein was maintained at 170 C.
  • the size of the mixer was such that the residence time of the acetone therein was about 37 minutes.
  • the eiiiuent organic phase was iiowed from the reaction system' toa fractionating column in which the unreacted acetone was strippedfrom the mixture. The residue was permitted to accumulate and was later distilled to separate the constituents thereof.
  • Example III Acetone .was condensed in the presence of dilute aqueous potassium hydroxide in an apparatus similar to that shown in Figure 2. The run was continued for 178 hours and the catalyst was in no way deteriorated at the end of this time.
  • the run was continued for 178 hours and the catalyst was in no way deteriorated at the end of this time.
  • Acetone fed to reactor g. p. h. 175.9 Water fed to reactong. p. h. 18.3 Residence time,y min. 17.5 Wt. per cent water in emuent organic layer 14.1 Wt. per cent KGH in eiliuent organic layer 0.024
  • a process for. producing isophorone' which comprises continuously introducing acetone into a. reaction zone and intimately contacting said ketone with a dilute aqueous solution containing between 15 and 35 per cent by weight of an alkali metal hydroxide with respect to the hydroxide and water therein at a temperature of from 130 C. to the critical temperature of acetone of about 235 C.
  • a process for producing an isophorone whichy comprises continuously introducing and commingling a 3 to 5 carbon atom saturated ketone with a dilute aqueous solution of an alkali metal hydroxide at a temperature between 150 C. and 200 C. while maintaining the reaction mixture in the liquid state by application of sulcient the comminsling therewith, and continuously introducing into the reaction mixture sufiicient water with respect to water withdrawn therefrom in said eiiiuent organic phase so as to maintain the concentration of said hydroxide in said dilute aqueous solution substantially constant at a value between and 35 per cent by weight.
  • a process for producing isophorone which comprises continuously introducing and ccmmingling acetone with a dilute aqueous solution of potassium hydroxide at a temperature between 150 C. and 200 C. while maintaining the reaction mixture in the liquid state by application of sufficient pressure to prevent boiling thereof, continuously withdrawing from the reaction mixture a portion of liquid organic .phase containing water extracted from said dilute aqueous solution by the commingling therewith, and continuously introducing into the reaction mixture sufficient water with respect to water withdrawn therefrom in said eiiluent organic phase so as to maintain the concentration of said hydroxide in said dilute aqueous solution substantially constant l at a value between 15 and 35 per cent by weight.
  • a process for producing an isophorone which comprises continuously introducing into a reaction zone and intimately contacting therein a saturated ketone of 3 to 5 carbon atoms with a dilute aqueous solution of an alkali metal hydroxide at a temperature of from 130 C. to the critical temperature of said ketone; continuously transferring a portion of the reaction mixture from said reaction zone to a stratiiicationaonc wherein said transferred reaction mixture separates into an aqueous phase and an organic phase.
  • suiilcient pressure being maintained in said repressure to prevent boiling thereof, continuously withdrawing from the reaction mixture a portion of liquid organic phase containing water extracted from said dilute aqueous solution by the commingling therewith, and continuously introducing into the reaction mixture suiicient water with respect to water withdrawn .therefrom in said eiuent organic phase so as to maintain the concentration of said hydroxide in said dilute aqueous solution substantially constant at a value between 15 and 35 per cent by weight.
  • a process for producing isophorone winch comprises continuously introducing and commingling acetone with a, dilute aqueous solution of an alkali metal hydroxide at a temperature between 1509 C. and 200 C. While maintaining the reaction mixture in the liquid state byl application of suflicient pressure to prevent boiling thereof, continuously withdrawing from the reaction mixture a portion of liquid organic phase containing water extracted from said dilute aqueous solution by the commingling therewith, and continuously introducing into the reaction mixture sufficient water with respect to water withdrawn therefrom in said yeilluent organic phase so as to maintain the concentration of said hydroxide in said dilute aqueous solution substantially constant at a value between 15 and 35 per cent by weight.
  • a process for producing isophorone which comprises continuously introducing and commingling acetone with a dilute aqueous solution of sodium hydroxide at a temperature between 150 C. and 200 C. While maintaining the reaction mixture in the liquid state by application of suiiicient pressure to prevent boiling thereof, continuously withdrawing from the reaction mixture a portion of liquid organic phase containing water4 extracted from said dilute aqueous solution by action zone and in said stratification zone to keep the entire contents therein in the liquid state; continuously returning stratified aqueous phase from said stratification zone to said reaction zone: continuously withdrawing from said stratification zone stratied liquid organic phase containing water extracted from said dilute aqueous solution by the contacting therewith; and continuously introducing into said reaction zone suicient water with respect to the water withdrawn in said efnuent organic phase to maintain the weight ratio of water to said alkali metal hydroxide in said dilute aqueous solution substantially constant at a value between 5.66:1 to 1.86z1.
  • a process for producing isophorone which comprises continuously introducing into a reaction zone and intimately contacting therein acetone with a dilute aqueous solution of an alkali metal hydroxide at a temperature of from 130 C. tothecritical temperature of acetone of about 235 C.; continuously transferring a portion of the reaction mixture from said reaction zone to a stratication zone wherein said transferred reaction mixture separates into an aqueous phase and an organic phase, sufficient pressure being maintained in said reaction zone and in said stratification zone tc keep the entire contents therein in theliquid state; continuously returning stratified aqueous v phase from said stratiiication zone to said reaction zone; continuously withdrawing from said stratification zone stratiiied liquid organic phase containing water extracted from said dilute ,9.
  • a process ior producing isophorone whichv inirodueiu comprises continuously into a ne action zone and intimately contactinl therein acetone with a dilute aqueous solution ot sodium lhydroxide at a temperature oi .from 130. C. to the critical temperature 'foi acetone o! about- 235 C.; continuously .transierrinz aportionot tho ⁇ reaction mixture.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US474060A 1943-01-28 1943-01-28 Production of isophorone and related products Expired - Lifetime US2399976A (en)

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US474060A US2399976A (en) 1943-01-28 1943-01-28 Production of isophorone and related products
GB60/44A GB583863A (en) 1943-01-28 1944-01-03 Production of isophorone and homo-isophorones
FR941124D FR941124A (fr) 1943-01-28 1945-12-28 Procédé de préparation de l'isophorone et produits analogues
DEN1889A DE840842C (de) 1943-01-28 1950-09-16 Verfahren zur Herstellung ungesaettigter cyclischer Ketone, wie Isophoron und homologe Isophorone

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Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2566564A (en) * 1946-09-10 1951-09-04 Distillers Co Yeast Ltd Process for the manufacture of isophorone and homo-isophorones
US2883429A (en) * 1959-04-21 diethoxy-j
US2968677A (en) * 1961-01-17 Purification of isophorone
US4165339A (en) * 1976-02-12 1979-08-21 Union Carbide Corporation Catalytic aldol condensations
US5849957A (en) * 1996-02-29 1998-12-15 Elf Atochem S.A. Process for obtaining isophorone
DE102010062603A1 (de) 2010-12-08 2012-06-14 Evonik Degussa Gmbh Verfahren zur Herstellung von 3-Aminomethyl-3,5,5-trimethylcyclohexylamin
WO2012076314A1 (de) 2010-12-08 2012-06-14 Evonik Degussa Gmbh Verfahren zur herstellung von isophoron
DE102011075777A1 (de) 2011-05-13 2012-11-15 Evonik Degussa Gmbh Verfahren zur Herstellung von Isophoron in Gegenwart mindestens eines Entschäumers in der Abwasserkolonne im Aufarbeitungsteil
FR3143600A1 (fr) 2022-12-19 2024-06-21 Arkema France Procédé de synthèse d’isophorone en phase liquide avec recyclage du catalyseur alcalin par électrodialyse
FR3143601A1 (fr) 2022-12-19 2024-06-21 Arkema France Procédé de synthèse d’isophorone en phase liquide avec recyclage des sous-produits

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1095818B (de) * 1958-09-15 1960-12-29 Bergwerksgesellschaft Hibernia Verfahren zur Herstellung von Isophoron

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2883429A (en) * 1959-04-21 diethoxy-j
US2968677A (en) * 1961-01-17 Purification of isophorone
US2566564A (en) * 1946-09-10 1951-09-04 Distillers Co Yeast Ltd Process for the manufacture of isophorone and homo-isophorones
US4165339A (en) * 1976-02-12 1979-08-21 Union Carbide Corporation Catalytic aldol condensations
US5849957A (en) * 1996-02-29 1998-12-15 Elf Atochem S.A. Process for obtaining isophorone
WO2012076314A1 (de) 2010-12-08 2012-06-14 Evonik Degussa Gmbh Verfahren zur herstellung von isophoron
DE102010062603A1 (de) 2010-12-08 2012-06-14 Evonik Degussa Gmbh Verfahren zur Herstellung von 3-Aminomethyl-3,5,5-trimethylcyclohexylamin
WO2012076317A1 (de) 2010-12-08 2012-06-14 Evonik Degussa Gmbh Verfahren zur herstellung von 3-aminomethyl-3,5,5-trimethylcyclohexylamin
DE102010062587A1 (de) 2010-12-08 2012-06-14 Evonik Degussa Gmbh Verfahren zur Herstellung von Isophoron
DE102011075777A1 (de) 2011-05-13 2012-11-15 Evonik Degussa Gmbh Verfahren zur Herstellung von Isophoron in Gegenwart mindestens eines Entschäumers in der Abwasserkolonne im Aufarbeitungsteil
WO2012156187A1 (de) 2011-05-13 2012-11-22 Evonik Degussa Gmbh Verfahren zur herstellung von isophoron in gegenwart mindestens eines entschäumers in der abwasserkolonne im aufarbeitungsteil
FR3143600A1 (fr) 2022-12-19 2024-06-21 Arkema France Procédé de synthèse d’isophorone en phase liquide avec recyclage du catalyseur alcalin par électrodialyse
FR3143601A1 (fr) 2022-12-19 2024-06-21 Arkema France Procédé de synthèse d’isophorone en phase liquide avec recyclage des sous-produits
WO2024133119A1 (fr) 2022-12-19 2024-06-27 Arkema France Procédé de synthèse d'isophorone en phase liquide avec recyclage des sous-produits
WO2024133157A1 (fr) 2022-12-19 2024-06-27 Arkema France Procédé de synthèse d'isophorone en phase liquide avec recyclage du catalyseur alcalin par électrodialyse

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FR941124A (fr) 1948-01-03
GB583863A (en) 1947-01-01
DE840842C (de) 1952-06-05

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