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WO2015095879A1 - Procédé de fabrication de 2-méthyl-1,3-dioxolane par un procédé de polycondensation à l'état solide - Google Patents

Procédé de fabrication de 2-méthyl-1,3-dioxolane par un procédé de polycondensation à l'état solide Download PDF

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Publication number
WO2015095879A1
WO2015095879A1 PCT/US2014/071956 US2014071956W WO2015095879A1 WO 2015095879 A1 WO2015095879 A1 WO 2015095879A1 US 2014071956 W US2014071956 W US 2014071956W WO 2015095879 A1 WO2015095879 A1 WO 2015095879A1
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Prior art keywords
acid
ethylene glycol
catalysts
dioxolane
process gas
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PCT/US2014/071956
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English (en)
Inventor
Clive Alexander Hamilton
Robert Edward Neate
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INVISTA TECHNOLOGIES Sarl
Invista Technologies SARL USA
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INVISTA TECHNOLOGIES Sarl
Invista Technologies SARL USA
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/12—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms

Definitions

  • the invention is related to methods for manufacturing 2-methyl-1,3-dioxolane ("MDO"). It is also related to systems implementing such methods in a solid state polycondensation process.
  • MDO 2-methyl-1,3-dioxolane
  • polyoxymethylene resins polyoxymethylene resins. These copolymers have a better hydro lytic stability than the homopolymers. MDO can be manufactured using several techniques (See U.S. Patent No. 3027352), including acetalization of aldehydes and ketalization of ketones with ethylene glycol.
  • Polyester resins such as poly(ethyIene terephthalate) (PET) resins are widely produced and used, for example, in beverage and food containers, thermofoiming applications, textiles, and engineering resins.
  • PET poly(ethyIene terephthalate)
  • the production of PET is based on a reaction between tereplithalic acid and/or dimethyl terephthalate with ethylene glycol (via esterification and/or transesterification, respectively).
  • the resulting bis-hydroxyethyl terepthalate pre-polymers are then joined by means of polycondensation reactions to give a polymeric product.
  • SSP solid state polycondensation
  • PET polycondensation cleavage products
  • AA acetaldehyde
  • the presence of AA is often of significant importance in PET production and its content is rigorously controlled for certain uses.
  • PET is used to produce bottles as containers for beverages
  • AA in the bottle can migrate to the beverage, causing an undesirable flavor in the beverage (which is particularly noticeable in water). It is therefore desirable to minimize the content of AA in the final PET product.
  • reaction byproducts such as AA are removed via a process gas that is at least partially re-circulated through the system.
  • the process gas takes up impurities ⁇ e.g., reaction byproducts) from the system and the impurity-rich gas is subsequently purified to remove those impurities and render the gas available for reuse in the system.
  • impurities e.g., reaction byproducts
  • Various means are known for purifying process gases.
  • One common gas purification system utilizes a gas scrubber containing an aqueous or organic fluid that is brought into contact with the impurity-rich gas and which purifies the gas via a liquid-gas exchange process. This process, however, does not convert the A A into a useful product.
  • acetaidehyde (as may be present in the process gas circulating within a solid state polycondensation (SSP) system for the production of polyethylene terepthalate (PET)) and ethylene glycol (EG) (as may be present as a washing liquid in a gas scrubber for the process gas) reversibly react to fonn 2-methyl-1,3-dioxolane (“MDO”) and water.
  • SSP solid state polycondensation
  • EG ethylene glycol
  • MDO 2-methyl-1,3-dioxolane
  • MDO 2-methyl-1,3-dioxolane
  • MDO 2-methyl-1,3-dioxolane
  • a catalyst can be incorporated within the gas scrubber to facilitate this reaction to form MDO.
  • the conversion of AA to MDO is beneficial as it effectively results in removal of AA from the system and creates a stream of MDO for use in manufacturing other chemicals.
  • a method of manufacturing 2-methyl-l ,3-dioxoJane ("MDO") in a polyester solid state polycondensation process comprising: (a) introducing a process gas inlet stream from a polyester polycondensation process comprising a first concentration of acetaidehyde into a gas scrubbing unit; (b) introducing a liquid ethylene glycol inlet stream into the gas scrubbing unit; (c) contacting the process gas inlet stream with the liquid ethylene glycol inlet stream in the presence of one or more acid catalysts in the gas scrubbing unit, wherein the acetaidehyde reacts with the ethylene glycol to form 2-methyI-1,3-dioxolane during said contacting step, the contacting step producing a liquid ethylene glycol outlet stream containing 2-methyl- 1,3-dioxolane; (d) removing at least part of the ethylene glycol outlet stream from the gas scrubbing unit; and
  • the process gas is selected from the group consisting of nitrogen, argon, carbon dioxide, and mixtures thereof
  • the method can further comprise recycling and/or using the purified process gas stream, for example, as a process gas stream in a further method of preparing a high molecular weight polymer.
  • the ethylene glycol stream after removal of MDO can be recirculated back to the gas scrubber.
  • the acid catalysts used in the method can vary and can be, in certain embodiments, homogeneous or heterogeneous acid catalysts.
  • the acid catalysts can be selected from the group consisting of mineral acids, sulfonic acids, carboxylic acids, and mixtures thereof.
  • the one or more acid catalysts are selected from the group consisting of a boron trihalide, an organoborane, an aluminum trihalide, methanesulfonic acid, ethanesulfonic acid, benzenesulfonic acid, p-toluene sulfonic acid, trifluoromethanesulfonic acid, a boric acid, hydrochloric acid, hydroiodic acid, hydrobromic acid, perchloric acid, nitric acid, sulfuric acid, fluorosulfuric acid, oxalic acid, acetic acid, phosphoric acid, citric acid, carbonic acid, formic acid, benzoic acid, and mixtures and derivatives thereof.
  • the one or more acid catalysts comprise a solid support having an acidic functionality attached thereto, wherein the acidic functionality is selected from the group consisting of a boron trihalide, an organoborane, an aluminum trihalide, methanesulfonic acid, ethanesulfonic acid, benzenesulfonic acid, p-toluene sulfonic acid, trifluoromethanesulfonic acid, a boric acid, hydrochloric acid, hydroiodic acid, hydrobromic acid, perchloric acid, nitric acid, sulfuric acid, fluorosulfuric acid, oxalic acid, acetic acid, phosphoric acid, citric acid, carbonic acid, formic acid, benzoic acid, and mixtures and derivatives thereof.
  • the acidic functionality is selected from the group consisting of a boron trihalide, an organoborane, an aluminum trihalide, methanesulfonic acid, ethanesulf
  • the temperature at which the contacting step is conducted is about 50 °C or less.
  • MDO separation step in certain aspects, comprises neutralizing the ethylene glycol, filtering the ethylene glycol, distilling the ethylene glycol, or a combination thereof.
  • the clean ethylene glycol outlet stream may be used as a reactant to produce poly(ethylene terephthalate) via melt condensation polymerization.
  • an apparatus for manufacturing MDO comprising: a housing enclosing a chamber adapted to provide contact between a process gas and a scrubbing liquid, the chamber containing one or more solid acid catalysts; a supply of process gas from a polyester solid state polycondensation process comprising acetaldehyde; a first inlet in fluid communication with the chamber and in fluid communication with the supply of process gas comprising acetaldehyde and adapted to introduce the process gas comprising acetaldehyde into the chamber; a supply of ethylene glycol; a second inlet in fluid communication with the chamber and in fluid communication with the supply of ethylene glycol and adapted to introduce the ethylene glycol into the chamber; a first outlet in fluid communication with the chamber and adapted to remove an ethylene glycol stream containing 2-methyl-1,3-dioxolane from the chamber; and a separation device for receiving the ethylene glycol stream containing 2-methyl-1,3-dioxolane.
  • the one or more acid catalysts are heterogeneous acid catalysts, present in a packed tray within the manufacturing unit.
  • the operation of the unit can vaiy and may comprise, for example, a centrifugal-type scrubber, spray scrubber, impingement-type scrubber, packed tower-based scrubber, venturi- type scrubber, eductor venturi-type scrubber, film tower-based scrubber, scrubber with rotating elements, or a combination thereof.
  • FIG. 1 is a depiction of an apparatus for manufacturing MDO according to the invention.
  • FIG. 2 is a depiction of an exemplary SSP system according to the invention.
  • the present invention provides a method for manufacturing 2-methyI-1,3-dioxolane ("MDO") in a polyester solid state polycondensation (SSP) system using process gas containing acetaldehyde.
  • MDO 2-methyI-1,3-dioxolane
  • SSP polyester solid state polycondensation
  • the manufacture of MDO is facilitated by means of an ethylene glycol washing liquid in the presence of an acid catalyst, wherein the acid catalyst functions to convert acetaldehyde to MDO which can be more readily removed from the SSP system in the ethylene glycol stream.
  • the invention provides an apparatus for manufacturing MDO, which is equipped to receive the process gas and a washing fluid and bring the gas and fluid into contact with one another, wherein the gas purification system also contains one or more acid catalysts.
  • the SSP process is commonly used to produce high molecular weight polyethylene terephthalate (PET), which is known to produce acetaldehyde (AA) as an undesirable byproduct.
  • PET polyethylene terephthalate
  • AA acetaldehyde
  • the AA content in the final PET resin produced via SSP is advantageously minimized, as AA can subsequently leach out of PET, and has been noted to negatively impact the taste of beverages and/or foods contained in PET containers.
  • the inventors have found that AA present in the process gas can reversibly react with EG present in the gas scrubber to form 2-methyl-1,3-dioxolane ("MDO") and water.
  • MDO 2-methyl-1,3-dioxolane
  • one or more acid catalysts are incorporated within the gas scrubber to promote and/or enhance this reaction of AA and EG to form MDO.
  • the present disclosure focuses on methods and systems for the production of PET, it may be applicable to the production of other polymers, such as other polyesters, as well. In particular, it may be applicable to the production of various polymers wherein AA is produced as an undesirable reaction byproduct.
  • the SSP gas can be provided in a cleaner form ⁇ i.e., with decreased AA content), such that it can be more readily re-used in the SSP process. Using this cleaner SSP gas may effectively reduce AA contamination in the PET preparation process and thereby reduce the AA content of the subsequently produced PET.
  • the limit on AA content in the PET resin introduced to the SSP process can be increased (i.e.
  • the process may, in certain embodiments, be capable of more effectively decreasing the AA content throughout the SSP process. Further, by converting the AA to MDO, it may be possible to provide smaller, more efficiently designed scrubbers for use in the SSP system.
  • a catalyst can, in some embodiments, increase the rate of and/or percent conversion of AA to MDO.
  • a catalyst can shift the equilibrium of a reversible reaction to the product side.
  • FIG. 1 provides a schematic depiction of a MDO manufacturing apparatus 10, exemplified in the form of a gas scrubber unit.
  • Figure 1 depicts a general gas scrubber setup, it is to be understood that a variety of gas scrubbers are known in the art and can be modified for use according to the present invention. Scrubbers can vary widely in size, capacity, operation, and complexity, and all such types are intended to be encompassed by the disclosure provided herein.
  • scrubbers are designed so as to bring a dirty process gas into intimate contact with a washing fluid that can remove certain contaminants therefrom (e.g., by adsorption).
  • Certain scrubbers operate by means of directing dirty process gas through a tortuous path (e.g., using baffles and other restrictions) and/or provide for some degree of turbulence to ensure significant contact with a washing fluid, wherein contaminants are removed by contact between the gas and the washing fluid.
  • the washing fluid may be flowed, e.g., concurrently to the process gas within the scrubber or counter- currently to the process gas within the scrubber (as shown in Figures 1 and 2), although the scrubber may operate in other ways.
  • Scrubbers may be, for example, centrifugal-type scrubbers, spray scrubbers, impingement-type scrubbers, packed towers, venturi-type scrubbers, eductor venturi-type scrubbers, film towers, scrubbers with rotating elements, or scrubbers comprising multiple of these and other types.
  • gas scrubbers many types and design configurations of gas scrubbers are known and intended to be included within the present disclosure, exemplary types and design configurations are described for example, in U.S. Patent Nos.
  • the MDO manufacturing apparatus shown in Figure 1 is configured with a gas inlet, through which dirty process gas 20 (e.g., from the SSP process) enters the unit. It is noted that although the gas inlet is shown on the bottom of the unit, the dirty process gas may enter from the top or side of the unit.
  • the dirty process gas generally comprises various byproducts of the polycondensation reaction, including, but not limited to, cleavage products such as water, ethylene glycol, methyl dioxolane, and aldehydes (e.g., acetaldehyde).
  • the process gas entering the scrubber e.g., the process gas of the SSP system
  • the process gas may, in some embodiments, comprise nitrogen, argon, helium, carbon dioxide, or mixtures thereof.
  • the temperature of the process gas (if discharged from the polyester melt phase reactor) prior to entering the MDO manufacturing apparatus can vary from about 100°C to greater than 250°C, including from 100°C to about 500°C, from about 100°C to about 400°C, from about 100°C to about 300°C, from about 100°C to about 200°C, and from about 250°C to about 310°C. If the process gas is discharged from a condensing system for reaction by-products of a polyester melt phase reactor, than the temperature can vary from about 0°C to about 100°C, including 0°C to about 50°C.
  • the dirty process gas comes into contact with the washing liquid containing ethylene glycol (EG).
  • a clean EG supply 30 is in fluid contact with the unit, takes up aldehydes in the dirty process gas, and the reaction of EG and aldehydes produces: (1) an MDO stream 40, comprising EG and MDO; and (2) a clean process gas stream 50.
  • the ethylene glycol / MDO stream can be recirculated back to the gas scrubber to react with more acetaldehyde.
  • a portion of the recycled ethylene glycol stream can be purged to control the concentration of MDO in the unit.
  • the glycol is supplied from the glycol-driven ejector system of a melt phase polyester process.
  • the emissions reduction can vary from 30% - 100%, including 30% - 90%, 30% - 80%, 30% - 70%, 30% - 60%, 30% - 50%, 40% - 90%, 40% - 80%, 40% - 70%, 40% - 60%, 50% - 80%, and 50% - 70%, compared to a scrubbing unit not using the process described in the various aspects.
  • the ethylene glycol / MDO stream 40 can go to a separation device to separate out the MDO.
  • various acid catalysts can be incorporated within the gas scrubber.
  • Acid catalysts that may be used according to the invention to promote the reaction of A A and EG to fonn MDO include, but are not limited to, Lewis acids and Bronsted acids. Acid catalysts may be, for example, mineral (i.e., inorganic) acids, sulfonic acids, or carboxylic acids.
  • Certain specific acids include, but are not limited to, boron trihalides, organoboranes, aluminum trihalides, other various metal cations or compounds (which generally can serve as Lewis acids only after dissociating a Lewis base bound thereto); methanesulfonic acid, ethanesulfonic acid, benzenesulfonic acid, p-toluene sulfonic acid (TsOH), trifiuoromethanesulfonic acid, boric acids, hydrochloric acid, hydroiodic acid, hydrobromic acid, perchloric acid, nitric acid, sulfuric acid, fluorosulfuric acid, oxalic acid, acetic acid, phosphoric acid, citric acid, carbonic acid, formic acid, and benzoic acid.
  • heterogeneous acid catalysts may be effective in enhancing the conversion of AA and EG to MDO
  • one or more heterogeneous catalysts are used (generally in solid form).
  • Heterogeneous acid catalysts generally comprise one or more acid functional groups immobilized on a solid support that is insoluble in the liquid or gas in which the reaction is to be conducted.
  • Heterogeneous catalysts are advantageous in their ease of implementation, ease of removal, and the ability to maintain EG in neutral form.
  • Various acidic functionalities can be provided on solid supports to provide the desired functionality in a solid form, such as those acidic moieities noted above.
  • Various solid supports can be used as well, including, but not limited to, silica, clay, synthetic or natural polymers.
  • Certain exemplary heterogeneous catalysts include AmberlystTM polymeric catalysts and ion exchange resins, which generally display a sulfuric acid functional group.
  • Other exemplary heterogeneous acid catalysts are described, for example, in U.S. Patent Nos. 5,294,576 to Ho et al; 5,481,0545, 563,313, 5,409,873, and 5,571,885 to Chung et at, 5,663,470, 5,770,539, 5,877,371, and 5,874,380 to Chen et ah; and 6,436,866 to Nishikido, which are all incorporated herein by reference.
  • a MDO manufacturing device for example a gas scrubber, may have a temperature of between about 5°C and around 60°C, such as about 8°C at the top, about 12°C in the middle, and about 45°C at the bottom of the scrubber.
  • a MDO manufacturing device for example a gas scrubber
  • At ambient temperature there is generally no appreciable reaction between AA and EG to produce MDO.
  • the reaction is enhanced.
  • an added acidic catalyst allows for an efficient reaction of AA and EG to produce MDO at temperatures typically associated with a gas scrubber.
  • the high temperatures generally required for reaction of A A and EG in the absence of an added catalyst to form MDO are not required and the methods of the invention can be readily implemented into existing scrubber systems with little to no modification or control of temperature within the scrubber.
  • reaction of AA and EG to form MDO is reversible and both the forward reaction and the reverse reaction are acid-catalyzed. It is preferr ed that, under the conditions of use, the reaction of AA and EG to form MDO is favored over the reverse reaction.
  • the reverse reaction requires water; therefore, in some embodiments, it may be advantageous to limit the water content in the washing fluid.
  • the latter (reverse) reaction is described in further detail, for example, in U.S. Patent Application Publication No. 201 1/0097243 to Reimann et al, which is incorporated herein by reference.
  • the acidic catalyst can be incorporated within the MDO manufacturing apparatus in various ways.
  • the apparatus comprises a multi-stage setup (e.g., the 3 -stage setup of Figure 1, comprising stages A, B, and C).
  • a heterogeneous catalyst may be packed within a vessel (e.g., a packed tray/bed) held within the unit to provide one or more layers of material through which the ethylene glycol washing solution passes.
  • the catalyst may thus be provided in one or more of the three stages A, B, and C, depicted in scrubber 10 (i.e., at the top, middle, or bottom of the unit).
  • multi-stage units can have vaiying numbers of stages and the catalyst can be incorporated within any of these stages.
  • the heterogeneous catalyst can be provided at vaiying levels within the unit; however, it is advantageously toward the bottom of the unit (i.e., a portion of the unit that is at a higher temperature, as increased temperature promotes the conversion of AA and EG to MDO).
  • the catalyst can be provided in any one or more of stages A, B, and C, catalyst may be provided, at least in part, in stage C.
  • use of an acidic catalyst as described herein allows for the reaction to occur with good conversion of reactants to product, even at lower temperatures than generally required for such a reaction.
  • Other physical means for ensuring contact between the acid catalyst and the dirty ethylene glycol are intended to be encompassed by the present invention as well.
  • the amount of catalyst added to the gas scrubber system can vary, but may generally be any amount sufficient to catalyze the reaction of at least a portion, and including at least a substantial portion, of the AA with EG to produce MDO. Specifically, the amount of catalyst can vary from 1 kg per tonne per hour of EG scrubber liquid (1 kg/tph) to 1000 kg/tph; including 2 kg/tph to 100 kg/tph; 2 kg/tph to 10 kg/tph; and 5 kg/tph.
  • the MDO manufacturing apparatus as described herein is advantageously incorporated within an SSP system for polyester production, although application of the methods of the invention may be useful in other applications utilizing a unit (e.g. gas scrubber) wherein AA is beneficially minimized.
  • the SSP system generally operates according to methods known in the art, as described for example, in U.S. Patent No. 7,819,942 to Christel ei at, which is incorporated herein by reference.
  • Figure 2 of the present application illustrates one exemplary SSP system 6 ⁇ , although the components within the system can vary.
  • the SSP process typically begins with the introduction of a substantially amorphous PET base chip, such as a base chip having an intrinsic viscosity of about 0.6 iV.
  • the acetaldehyde content in the base chip can vary, but is advantageously reduced to or maintained at a low level through the SSP process.
  • the base chip is crystallized to about 40 or 45% crystalline content in a crystallizer unit 70 by application of heat.
  • the chip then typically passes through a preheater 80 and then can then be further heated in a reactor unit 90, which generally increases the crystallinity of the PET even further (e.g., to about 65-70% crystalline). It is within the reactor unit that the PET generally exhibits the greatest desirable buildup of intrinsic viscosity.
  • the PET then passes into a cooler 100 to give an SSP PET chip having a higher intrinsic viscosity than the base chip (e.g., about 0.8 iV) and having a relatively low AA content (e.g., about 100 ppm or less, about 50 ppm or less, about 10 ppm or less, about 9 ppm or less, about S ppm or less, about 7 ppm or less, about 6 ppm or less, about 5 ppm or less, about 4 ppm or less, about 3 ppm or less, or about 2 ppm or less, in some embodiments, even lower AA values are obtainable, such as about 1 ppm or less.
  • AA content e.g., about 100 ppm or less, about 50 ppm or less, about 10 ppm or less, about 9 ppm or less, about S ppm or less, about 7 ppm or less, about 6 ppm or less, about 5 ppm or less, about 4 ppm or less, about
  • the reactor units within the SSP system can vaiy and may, in certain embodiments, include devices ranging from fixed-bed, solid-air jet, or fluidized bed reactors, and/or reactors having agitating implements or reactors that move. Various temperatures and pressures can be utilized in the various stages of the SSP process.
  • FIG. 2 illustrates an exemplary flow system of the process gas, which then enters the unit (as "Dirty N2 in”).
  • Ethylene glycol the reacting fluid cycled through the unit, reacts with the aldehyde in the process gas, providing: (1) a EG and MDO stream; and (2) process gas in "clean" form, at which point it can be subsequently reused (e.g., within the reactor 90, as shown in Figure 2).
  • the unit 110 according to the invention, further comprises an acid catalyst as provided herein. It is to be understood that Figure 2 provides one exemplary system in which an acid catalyst can be used; this disclosure is not intended to be limiting, and the methods and materials described herein can be applied to various methods and systems wherein AA and EG may be present.
  • the ethylene glycol containing the MDO can be cleaned for reuse for various purposes.
  • the MDO can be separated, for example, by filtration, decantation, and/or distillation, and the cleaned EG recycled back into the system.
  • homogeneous catalysts can be used according to the invention, their use generally results in the production of acidified glycol, which must be neuti'alized in addition to being filtered and/or distilled.
  • the cleaned EG can beneficially be used, for example, as an input material for melt phase condensation polymerization to produce additional PET.
  • a single EG stream may be used in the various steps in preparing high molecular weight PET.
  • EG recycled from the SSP process can be fed into a reaction with terephthalic acid and/or dimethyl terephthalate to give PET monomer units which are joined by melt phase condensation polymerization and which may be furtlier subjected to SSP to increase the intrinsic viscosity thereof.
  • Table 1 AA and MDO concentrations at 50°C as a function of time
  • the data illustrates that at 50°C, the % AA decreases slowly and the % MDO rises slowly over the time period displayed.
  • the data illustrates that at 85°C, the % AA decreases more quickly and the % MDO rises more quickly over the time period displayed than at 50 °C.
  • the data illustrates that at 130°C, the % AA decreases even more quickly and the % MDO rises even more quickly over the time period displayed than at 85 °C.

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  • Organic Chemistry (AREA)
  • Polyesters Or Polycarbonates (AREA)

Abstract

L'invention concerne un procédé de fabrication de 2-méthyl-1,3-dioxolane par un système de polymérisation à l'état solide de polyester. Le procédé comprend l'utilisation d'un catalyseur acide pour effectuer la conversion d'acétaldéhyde présent dans le système en 2-méthyl-1,3-dioxolane, qui peut être facilement retiré dans le courant d'éthylèneglycol.
PCT/US2014/071956 2013-12-18 2014-12-22 Procédé de fabrication de 2-méthyl-1,3-dioxolane par un procédé de polycondensation à l'état solide Ceased WO2015095879A1 (fr)

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