Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
  • C07C51/083—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid anhydrides
  • C07C51/087—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid anhydrides by hydrolysis
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
  • C07C51/42—Separation; Purification; Stabilisation; Use of additives
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
  • C07C51/42—Separation; Purification; Stabilisation; Use of additives
  • C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
  • C07C51/44—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation by distillation
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C55/00—Saturated compounds having more than one carboxyl group bound to acyclic carbon atoms
  • C07C55/02—Dicarboxylic acids
  • C07C55/10—Succinic acid
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C55/00—Saturated compounds having more than one carboxyl group bound to acyclic carbon atoms
  • C07C55/02—Dicarboxylic acids
  • C07C55/12—Glutaric acid

Definitions

• the present invention relates to a process for preparing diacid compounds.
• It relates more particularly to a process for preparing diacid compounds implementing a hydrolysis reaction.
• branched diacid compounds such as 2-methylglutaric acid (also called MGA) and 2-ethylsuccinic acid (also called ESA).
• MGA has a promising future in the chemical industry. It is a mixture with functionalities that can replace adipic acid, which is used for the preparation of nylon. It can be used as a substitute for adipic acid, as a monomer for the preparation of polyurethanes, plasticizers, detergents or as a solvent.
• diacid compounds by hydrolysis of dinitrile compounds in the presence of an excess of basic hydroxyl compound, the carboxylate salt obtained being then reacted with a mineral acid to recover the diacid compound.
• One of the aims of the present invention is to propose a process for the preparation of diacid compounds with a conversion rate and yield equivalent to or even greater than that of the processes of the state of the art, which is easy to implement and inexpensive to manufacture. the industrial scale.
• Another object of the present invention is to provide a process that does not generate effluents or by-products that are important and harmful to the environment.
• Another object of the invention is to provide a method whose co-products are easily recoverable and valued.
• Another object of the present invention is to provide a method for upgrading the co-products of the hydrocyanation of butadiene.
• the subject of the invention is a process for the preparation of at least one diacid compound comprising a step of hydrolysis of at least one imide compound.
• the present invention relates to a process for preparing at least one diacid compound comprising a hydrolysis reaction step of at least one imide compound, carried out in the absence of catalyst.
• the yield ⁇ ( ⁇ ) of a product B at the end of the reaction is defined by the ratio of the number of moles of B formed ⁇ ( ⁇ ) at the end of the reaction to the number of moles of reagent.
• the selectivity S (B) of a product B at the end of the reaction is defined by the ratio of the number of moles of B formed ⁇ ( ⁇ ) at the end of the reaction to the number of moles of reagent.
• diacid compound means an organic chemical compound comprising two carboxylic acid functions (-C (O) OH).
• the diacid compounds are preferably C 4 -C 20 .
• the two carboxylic acid functions are preferably separated by at least 2 carbon atoms, typically 2 or 3. In other words, the two carboxylic acid functions are not carried by the same atom of carbon.
• the diacid compound is optionally in the form of ammonium monocarboxylate because of the presence of ammonia from the hydrolysis reaction in the reaction medium. Such compounds are especially useful as monomers for the preparation of polyurethanes.
• the term "imide compound” means a heterocyclic organic chemical compound comprising a cyclic imide (-C (O) -NH-C (O) -) function, that is to say which is included in a cycle.
• the imide compounds are preferably C 4 -C 20 .
• the heterocyclic ring of the imide compounds consists of carbon atoms, typically 2 to 12, and the nitrogen atom of the imide function.
• the imide compound is a compound or a mixture of compounds of general formula (I) below:
• the diacid compound is a compound or a mixture of compounds of the following general formula (II):
• -A- radical represents a divalent hydrocarbon radical comprising 2 to 12 carbon atoms, linear or branched, saturated or unsaturated.
• the -A- radical is typically a divalent alkylene group comprising on average at least 2 carbon atoms, preferably from 2 to 6, advantageously from 2 to 4, preferably 4 carbon atoms.
• the imide compound is for example a mixture of different compounds of formula (I), in which the various -A- radicals are preferably isomeric radicals comprising an identical number of carbon atoms.
• the method of the invention can be implemented from a single imide compound or a mixture of imide compounds, isomeric or not.
• the -A- radical is branched.
• the -A- radical is saturated.
• the -A- radical is linear.
• the radical -A- is unsaturated.
• the -A- radical is an unsubstituted hydrocarbon radical, that is to say only consisting of carbon atoms and hydrogen.
• the radical -A- is a linear alkyl chain substituted with side groups comprising heteroatoms, such as nitrogen, oxygen or sulfur atoms.
• the radical -A- may be substituted with one or more side groups selected from the group consisting of -CN, -OH, -Oalkyl (CrC 6 ), phenyl, -O-phenyl, halogen.
• the radical -A- represents a divalent saturated hydrocarbon radical comprising from 2 to 6 carbon atoms, in particular a C 2 -C 6 alkylene radical, preferably of general formula -C 4 H 8 -, branched preference.
• the radical -A- is preferably chosen from the group consisting of -CH 2 -CH 2 -CH (CH 3 ) - and -CH 2 -CH (CH 2 CH 3 ) - radicals.
• the process of the invention is implemented from 2-methylglutarimide, 2-ethylsuccinimide and mixtures thereof.
• composition of matter comprising branched imide compounds, more particularly:
• the starting imide of formula (I) is the
• MMI 2-methylglutarimide
• MGN methylglutaronitrile
• This mixture preferably corresponds to the distillation fraction making it possible to separate the branched dinitriles (2-methylglutaronitrile and 2-ethylsuccinonitrile) from adiponitrile.
• This mixture of dinitriles generally has the following composition by weight:
• 2-methylglutaronitrile from 70% to 95%, preferably from 80% to 85%;
• 2-ethylsuccinonitrile from 5% to 30%, preferably from 8% to 12%;
• adiponitrile from 0% to 10%, preferably from 1% to 5%,
• the starting imide compound of formula (I), especially in the case of 2-methylglutarimide (MGI), can be obtained from 2-methylglutaronitrile (MGN), or from a mixture of dinitriles such as described above, for example according to a method for reacting MGN or the mixture of dinitriles with an acid. It can also be obtained by a hydrolysis process of the MGN or the dinitrile mixture, in the presence of water and a catalyst, for example of the titanium oxide type.
• the process of the invention makes it possible to obtain 2-methylglutaric acid, 2-ethylsuccinic acid, as well as their mixtures.
• the -A- radical represents a divalent unsaturated hydrocarbon radical comprising from 2 to 6 carbon atoms, preferably chosen from the group consisting of the ethylenyl radical and the o-phenylene radical.
• ethylenyl radical is meant a radical of formula:
• the method of the invention can be implemented from maleimide or phthalimide.
• the process of the invention makes it possible to obtain maleic acid and phthalic acid respectively.
• the invention also relates to the products, including compositions of materials, obtainable or directly obtained by this method.
• the invention also relates to the use of these products or compositions of materials, especially as solvents, co-solvents, monomers and synthesis intermediates.
• the imide compounds are hydrolyzed to diacid compounds by reaction with water molecules. It is said that the diacid compounds are the products of the hydrolysis of the imide compounds.
• the starting imide compounds are hydrolysed to diacid compounds by hydrolysis of the imide functions of the imide compounds. Hydrolysis of the imide function causes the opening of the heterocyclic ring of the imide compounds.
• the carbon atoms of the two carboxylic acid functions of each diacid compound correspond to the carbon atoms of the imide function of the corresponding imide compound.
• hydrolysis reaction of an imide compound can be represented as a diacid compound of the process of the invention as follows:
• the diacid compound obtained is optionally in the form of ammonium monocarboxylate:
• the hydrolysis reaction step of the process of the invention is carried out essentially in the presence of water, preferably only in the presence of water.
• the hydrolysis reaction step of the process of the invention is carried out in the absence of catalyst.
• the imide compounds are hydrolyzed to diacid compounds without said imide compounds being in the presence of any catalyst, in any quantity whatsoever.
• no homogeneous catalyst or heterogeneous catalyst supported on a particulate material or on a fixed bed is used.
• catalyst means a compound that accelerates a chemical reaction, such as for example a hydrolysis reaction.
• a catalyst is used in a quantity that is substoichiometric with respect to the reactants (typically less than 5 mol%).
• It can be acidic or basic catalyst.
• acidic catalyst is meant an acid catalyst in the sense of Lewis, as defined in the literature, in particular by Jerry MARCH, Advanced Organic Chemistry, 3rd edition, John Wiley and Sons, 1985, pp. 227 and following.
• basic catalyst is meant a basic Lewis catalyst, as defined in the literature, in particular by Jerry MARCH, Advanced Organic Chemistry, 3rd edition, John Wiley and Sons, 1985, pp. 227 and following.
• catalyst in particular a heterogeneous catalyst based on hydroxides and / or alkali oxides, alkaline earth and / or lanthanides.
• he can in particular, be alumina, titanium oxide, magnesia (MgO), Mg (OH) 2 , CaO, Ca (OH) 2 , BaO, Ba (OH) 2 , heteropolyacids , pentasil and faujasite type zeolites, clays, metal phosphates, silica / alumina mixtures and the like.
• It may be in particular a catalyst chosen from oxides, hydroxides and basic salts of alkaline earth and / or rare earths having no degree of valence IV and among the minerals containing it.
• acid catalyst is also meant an aqueous solution of strong acid, such as an aqueous solution of hydrochloric acid, sulfuric acid or nitric acid.
• basic catalyst is also meant a strong aqueous base solution, such as a solution of soda or potash.
• the inventors have discovered that a hydrolysis reaction of an imide compound to a diacid compound does not require the presence of a catalyst. Even more surprisingly, the inventors have discovered a non-catalyst process which makes it possible to obtain a conversion rate, a yield, and a reaction time equivalent to a process using a catalyst.
• the method according to the invention has the other advantage of not generating salts, which usually need to be separated, treated and destroyed.
• the ammonia formed by the hydrolysis of the imide compound can be evacuated in gaseous form as and when it is formed and / or at the end of the reaction, by distillation. This particular aspect of the process will be detailed later.
• the process according to the invention comprises, before the hydrolysis reaction step, a step of placing at least one imide compound in contact with water to obtain a mixture of the imide compound and 'water.
• the starting reagents of the hydrolysis reaction are thus brought into contact.
• the only and unique reagents involved are the imide compound (or a mixture of imide compounds) and water.
• the placing step may consist of the preparation of a mixture comprising water and the imide compound.
• the hydrolysis reaction of the process according to the invention is typically carried out in a reactor, previously charged with at least one imide compound and water, which constitute the reaction medium of the hydrolysis reaction of the process of the invention.
• This mixture can be produced in the reactor, or outside the reactor and then introduced into the reactor.
• the presence of the imide compound and the water is generally carried out at the beginning of the process.
• the bringing into contact with the imide compound and water can be continued during the hydrolysis reaction, especially in the case of a continuous process.
• the imide compound and / or water are introduced continuously into the reactor.
• the molar ratio between water and the imide compound is from 10 to 100, preferably from 15 to 30, and preferably about equal at 20.
• Said molar ratio corresponds to the ratio of the amount of water (in moles) to the amount of imide compound (in moles) introduced into the reactor.
• the optimum conversion rate is obtained when the molar ratio is more particularly between 15 and 30, and preferably about 20.
• the hydrolysis reaction step of the process of the invention is carried out at a temperature of from about 10 ° C to about 220 ° C.
• the reaction medium in which the hydrolysis reaction of the imide compound takes place in diacid compound is brought to a temperature of 160 ° C to 220 °.
• This heating of the reaction medium may be carried out by any means known in the art, such as electric heating or heat transfer fluid heating.
• Heating the reaction medium accelerates the hydrolysis reaction and reduces the time required to obtain the diacid compound.
• the temperature is preferably 170 ° C to 200 ⁇ C, preferably about 180 ° C.
• the above temperature ranges make it possible to obtain conversion rates of the imide compounds to diacid compounds similar to the processes of the state of the art with catalyst.
• the optimum conversion rate is obtained when the temperature is more particularly between 170 ° C. and 200 ° C., preferably about 180 ° C.
• the hydrolysis reaction step is typically carried out in the liquid phase.
• reaction medium remains liquid during this step.
• the hydrolysis reaction is carried out at a pressure of 1 to 50 bar, preferably at the autogenous pressure, that is to say that the pressure in the reactor is generated solely by heating the reaction medium. .
• the reactor is provided with means for controlling and regulating the pressure, such as a valve through which water vapor and other compounds in gaseous form escape, such as Ammonia formed in particular.
• the method of the invention can be implemented in closed system, that is to say without exchange of material between the inside and the outside of the reactor during the reaction.
• the process of the invention can be carried out in an open system, that is to say that an exchange of material between the inside and the outside of the reactor is allowed during the reaction, typically by means pressure regulation or by point opening of the reactor.
• the duration of the hydrolysis reaction step is generally from 30 minutes to 6 hours, preferably from 2 hours to 4 hours.
• the process of the invention makes it possible to obtain a satisfactory degree of conversion with a reaction time equivalent to that of the processes of the state of the art using a catalyst.
• ammonia is formed.
• the process of the invention is preferably carried out in an open system, allowing an evacuation of the ammonia.
• the ammonia does not escape from the reaction medium and the diacid compound formed is found mainly in the form of ammonium monocarboxylate in solution in water: According to an advantageous embodiment of the invention, the proportion of ammonium monocarboxylate obtained at the end of the process is reduced.
• the ammonia produced by the hydrolysis reaction is discharged from the reaction medium, continuously or in a pointwise manner and possibly repeatedly,
• This embodiment has the advantage of reducing the concentration of ammonia in the medium and of promoting the hydrolysis reaction by displacing the equilibrium.
• the ammonia is removed by a steam drive.
• the ammonia is withdrawn from the reactor in gaseous form by steam stripping.
• This variant makes it possible to evacuate the ammonia continuously.
• Ammonia can in particular be withdrawn using a suitable device to maintain the constant pressure, releasing gas when the pressure exceeds a certain value, and possibly allowing liquefaction after exhaust.
• This device can be separated from the reactor by a pipe.
• the removal of ammonia may be accompanied by a simultaneous removal of water also in gaseous form. It is preferably sought to limit simultaneous water removal. For example, it is possible for this purpose to cool the gases along a pipe separating the device reactor, so as to liquefy at least a portion of the water and return it to the reactor.
• the removed gas (s) can be recovered and reused, if necessary after separation of ammonia and water. After separation, the water can be reused for the implementation of the hydrolysis step. Continuous water can also be fed back into the reactor to renew the evaporating water that results in ammonia.
• the ammonia is discharged by "stripping" with nitrogen.
• nitrogen stripping is meant a nitrogen sweep, that is to say a step during which a stream of nitrogen under pressure is passed into the reactor in which the reaction takes place.
• hydrolysis in order to entrain ammonia in gaseous form.
• in the reactor is meant in the reactor skies and / or in the reaction medium. It is a sort of gas / liquid extraction.
• This nitrogen stripping step can be carried out one or more times during the process, and preferably at least twice.
• the "stripping" with nitrogen can be carried out continuously during the hydrolysis reaction by regulating the flow rate of nitrogen injected into the process. reaction medium.
• Ammonia thus evacuated in gaseous form is advantageously recovered by condensation, and can thus be recovered.
• the evacuated ammonia can typically be recovered by passing the ammonia-containing gases in a refrigerated line.
• ammonia recovered is directly recoverable or can be purified, for example by distillation, to separate the residual water and obtain valuable ammonia, for example in the processes for preparing nitric acid or hydrocyanic acid.
• the products of the hydrolysis of the imide compound are recovered during a step of recovering the diacid compound formed.
• reaction mixture comprising water, the diacid compound (s), optionally partially in the form of ammonium monocarboxylate, optionally ammonia, and optionally the compound (s) imides not reacted.
• the diacid compounds obtained can be purified by standard techniques such as, for example, treatment with an ion exchange resin, treatment with activated carbon, distillation, crystallization, liquid / liquid extraction.
• the diacid compounds generally have a relatively high boiling point, greater than 300 ° C.
• the boiling point of the MGA under 1 atm is in particular 320 ⁇ C.
• the diacid compounds obtained are preferably purified during a distillation step.
• This step of purification of the diacid compounds obtained by distillation makes it possible to evacuate in gaseous form all or part of the compounds which are not diacid compounds, such as water, unreacted reagents, and co-products of the hydrolysis reaction, such as ammonia formed in particular.
• This step also makes it possible, by evacuating the ammonia, to convert the compounds in ammonium monocarboxylate form into compounds in acid form.
• This step has the advantage of reducing the proportion of compound in ammonium monocarboxylate form and increasing the proportion of compound in acid form.
• the mixture obtained by hydrolysis of the MGI is placed in a boiler, equipped with a distillation column trays or packed or other suitable equipment.
• the system is subjected to a reduced pressure of 0.1 to 70 mbar, typically 0.7 mbar.
• the mixture in the boiler is heated to a column head temperature of typically 140 to 200 ° C, preferably 145 to 180 ° C.
• the process of the invention can be implemented batchwise, batchwise or continuously.
• EXAMPLE 1 Preparation of an MGI / ESI Mixture From a MGN / ESN Mixture
• the mixture of imide compounds used in the examples was obtained according to the method described hereinafter, from a mixture of dinitrile compounds of following weight composition: 87% 2-methylglutaronitrile (MGN), 11% 2-ethylsuccinonitrile (ESN) and 0.5% adiponitrile (DNA).
• MGN 2-methylglutaronitrile
• ESN 2-ethylsuccinonitrile
• DNA 0.5% adiponitrile
• Example A A test is performed without a catalyst: Example A.
• Example B with 0.1 g of 13X zeolite catalyst (Zeolyst ⁇ ) and Example C with 0.1 g of MgO catalyst (Aldrich).
• the mixture After closing the reactor, the mixture is heated to 200 ° C. with shaking.
• the gaseous phase is purged hot (above the boiling point of water) after 1 hour of heating in order to eliminate the ammonia formed.
• the reactor is then warmed for a further 2 hours and again purged hot before complete cooling.
• reaction medium is then filtered if necessary to remove the catalyst and diluted for analysis by HPLC.
• the conversion rate is low.
• the degree of conversion is greater than 90%.
• the non-catalyst test gives the same performance as the MgO catalyst test.
• the mixture is heated for 4 hours at 180 ° C. under the autogenous pressure of 8 bar.
• reaction mixture is collected at room temperature.
• the resulting liquid weighs 90.7g.
• the water is evaporated under reduced pressure at 60 ° C. 17.48 g of a viscous brown mixture are recovered.
• This mixture comprises MGA and ESA, in acid form (diacid) and in the form of ammonium salt (monocarboxylate).
• the conversion rate is 97% and the yield of diacid + monocarboxylate is 80% (5% diacid and 75% monocarboxylate).
• the predominantly MGA is obtained in the form of carboxylate.
• the mixture is heated for 6 hours at 180 ° C. under the autogenous pressure of 8 bar.
• the reaction mixture is collected at room temperature.
• the resulting liquid weighs 80.04g.
• the water is evaporated under reduced pressure at 60 ° C. 21.3 g of a viscous brown mixture are recovered.
• This mixture comprises MGA and ESA, in acid form (diacid) and in the form of ammonium salt (monocarboxylate).
• the conversion rate is 96% and the yield of diacid + monocarboxylate is 84% (7% diacid and 77% monocarboxylate).
• the predominantly MGA is obtained in the form of carboxylate.
• the mixture is heated for 2 hours at 180 ° C. under the autogenous pressure of 8 bar.
• the temperature of the reactor is reduced to 70 ° C., and nitrogen is circulated in the air for 30 minutes to "stripper" the ammonia.
• the heating is resumed for 2 hours, always at 180 ° C. and under 8 bars.
• the mixture is cooled and the ammonia is stripped again by circulating nitrogen for 30 minutes.
• the reaction mixture is collected at room temperature.
• the resulting liquid weighs 77.8g.
• the water is evaporated under reduced pressure at 60 ° C. 13.5 g of a brown viscous mixture are recovered.
• This mixture comprises MGA and ESA, in acid form (diacid) and in the form of ammonium salt (monocarboxylate).
• the mixture is heated for 2 h and 30 min at 200 ° C. under the autogenous pressure of 14 bar.
• the temperature of the reactor is reduced to 70 ° C., and nitrogen is circulated in the air for 30 minutes to "stripper" the ammonia.
• the heating is resumed for 2 hours and 30 minutes, again at 200 ° C. and under 14 bars.
• the mixture is cooled and the ammonia is stripped again by circulating nitrogen for 30 minutes.
• the reaction mixture is collected at room temperature.
• the resulting liquid weighs 75.7g.
• the water is evaporated under reduced pressure at 60 ° C. 12.7 g of a viscous brown mixture are recovered.
• This mixture comprises MGA and ESA, in acid form (diacid) and in the form of ammonium salt (monocarboxylate).
• diacid + monocarboxylate 87% and the yield of diacid + monocarboxylate is 85% (25% diacid and 60% monocarboxylate).
• the mixture is heated for 3 hours at 180 ° C. under the autogenous pressure of 8 bar.
• the temperature of the reactor is reduced to 70 ° C., and nitrogen is circulated in the air for 30 minutes to "stripper" the ammonia.
• the heating is resumed for 3 hours, always at 180 ° C. and under 8 bars.
• the mixture is cooled and the ammonia is stripped again by circulating nitrogen for 30 minutes.
• the reaction mixture is collected at room temperature.
• the resulting green-colored liquid weighs 79.7g.
• This mixture comprises MGA and ESA, in acid form (diacid) and in the form of ammonium salt (monocarboxylate).
• the conversion rate is 93% and the yield of diacid + monocarboxylate is 83% (8% diacid and 75% monocarboxylate).
• the liquid obtained and recovered is then placed in a boiler, equipped with a condenser and a trap, and then distilled at a boiler temperature of 165 ° C under reduced vacuum of 2 mbar.
• Potentiometric content of the boiler (diacid) and the contents of the trap (ammonium salt) are determined by potentiometry.
• the mixture is heated for 5 hours at 200 ° C. under autogenous pressure of 16 bar. Water is added continuously (about 0.5-1 ml / min) with an HPLC pump.
• ammonia formed is entrained with the water vapor. Manually regulates the output flow of water with a micrometer valve. The pressure decreases slowly during the test. Ammonia is trapped in a vial containing acidified water and a spatula tip of phenolphthalein to visualize the passage of acidic to basic medium.
• the reaction mixture is collected at room temperature.
• the resulting liquid weighs 124.9 g.
• This mixture comprises MGA and ESA, in acid form (diacid) and in the form of ammonium salt (monocarboxylate).
• the conversion rate is 96% and the yield of diacid + monocarboxylate is 78% (42% diacid and 36% monocarboxylate).
• MGA in acid form is obtained in admixture with the MGA monocarboxylate in an equivalent amount.
• the amount of ammonia is also measured in the reaction mixture and in the trap, relative to the amount of starting MGI:
• the continuous steaming drive makes it possible to evacuate a large quantity of ammonia from the reaction medium.
• Tests were carried out, in a closed system, by varying the ratio of the number of moles of water to the number of moles of imides introduced.
• the optimum yield is for a molar ratio of approximately 20.
• an aqueous solution of mixture of imide compounds of Example 1 is charged continuously with a flow rate of 0.36 ml / min. at 16% by mass.
• the reaction temperature is 210 ° C. and the outlet pressure of the reactor is set at 20 bars.
• the residence time at this temperature is of the order of one hour.
• the conversion rate is 90% and the yield of diacid + monocarboxylate is 83% (17% diacid and 66% monocarboxylate).
• the reaction mixture is collected at room temperature.
• the brown liquid obtained weighs 6.21 g.
• the water is evaporated under reduced pressure at 60 ° C.
• This mixture essentially comprises succinic acid in the form of ammonium salt (monocarboxylate).
• the conversion is 91% and the monocarboxylate selectivity is 96%.
• This mixture essentially comprises phthalic acid in the form of ammonium salt (monocarboxylate).

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