WO2025201986A1 - Compositions de monopropylène glycol - Google Patents

Compositions de monopropylène glycol

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Publication number
WO2025201986A1
WO2025201986A1 PCT/EP2025/057501 EP2025057501W WO2025201986A1 WO 2025201986 A1 WO2025201986 A1 WO 2025201986A1 EP 2025057501 W EP2025057501 W EP 2025057501W WO 2025201986 A1 WO2025201986 A1 WO 2025201986A1
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WO
WIPO (PCT)
Prior art keywords
composition
distillation
wood
weight
fraction
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Pending
Application number
PCT/EP2025/057501
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English (en)
Inventor
Sebastian FUNTAN
Konrad GEBAUER
Isko Kajanto
Peter RÖGER
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UPM Kymmene Oy
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UPM Kymmene Oy
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Publication of WO2025201986A1 publication Critical patent/WO2025201986A1/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C31/18—Polyhydroxylic acyclic alcohols
    • C07C31/20—Dihydroxylic alcohols
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C31/18—Polyhydroxylic acyclic alcohols
    • C07C31/20—Dihydroxylic alcohols
    • C07C31/205—1,3-Propanediol; 1,2-Propanediol

Definitions

  • Monopropylene glycol is an important raw material that is used in a multitude of applications and industrial processes.
  • monopropylene glycol is used to produce polymers such as polyesters and polyurethanes.
  • Monopropylene glycol is made on an industrial scale from petrochemicals derived from crude oil, but due to environmental concerns there is a strong interest in obtaining the compound from renewable resources. In this regard, it is known that sugars contained in plant mass can be converted to monopropylene glycol by catalytic hydrogenolysis.
  • the present disclosure provides a composition comprising: monopropylene glycol in an amount of at least 98.0% by weight of the composition; and 2,3-pentanediol.
  • the disclosure is directed to uses and methods involving the compositions described herein.
  • the disclosure is also directed to processes for preparing the compositions, as well as compositions obtainable by said processes.
  • glycol refers to an aliphatic compound containing two hydroxy groups attached to different carbon atoms, wherein said carbon atoms may or may not be adjacent.
  • the composition comprises monopropylene glycol (also known as MPG, 1,2-propanediol or propane-1, 2-diol) and 2,3-pentanediol (also known as pentane-2,3-diol).
  • MPG monopropylene glycol
  • 2,3-pentanediol also known as pentane-2,3-diol
  • the composition comprises monopropylene glycol in an amount of at least 98.0% by weight of the composition, 2,3-pentanediol in an amount of from 0.1% to 1.5% by weight of the composition, and 1,2-butanediol in an amount of from 0.1% to 0.5% by weight of the composition.
  • the composition comprises monopropylene glycol in an amount of at least 98.1% by weight of the composition, 2,3-pentanediol in an amount of from 0.1% to 1.5% by weight of the composition, and 1,2-butanediol in an amount of from 0.1% to 0.3% by weight of the composition.
  • the composition comprises monopropylene glycol in an amount of at least 98.1% by weight of the composition, 2,3-pentanediol in an amount of from 0.1% to 1.5% by weight of the composition, 1,2-butanediol in an amount of from 0.1% to 0.3% by weight of the composition, and 2,3-butanediol in an amount of from 0.001% to 0.1% by weight of the composition.
  • the composition is substantially anhydrous, by which is meant that the composition contains less than 0.2% of water by weight of the composition. In an embodiment, the composition contains less than 0.1%, more preferably less than 0.05%, of water by weight of the composition. More preferably, the composition is anhydrous.
  • the composition is a bio-based composition that is obtained from a renewable resource.
  • bio-based refers to a composition or compound having a percent modern carbon (pMC) of at least 80% as measured using the ASTM D6866-21 test method. This test method is a standard method for experimentally determining the biobased carbon content of solid, liquid and gaseous samples using radiocarbon analysis, and it distinguishes carbon resulting from contemporary bio-based materials versus those derived from fossil-based materials.
  • the composition has a pMC of at least 80% as measured using the ASTM D6866-21 test method.
  • the composition has a pMC of at least 90%, more preferably 95%. More preferably, the composition has a pMC of at least 99%, for example 100%.
  • the composition is a bio-based composition that is prepared from a wood-based raw material, such as hardwood or softwood.
  • the wood-based raw material may originate from, e.g., pine, poplar, beech, aspen, spruce, eucalyptus, ash, oak, maple, chestnut, willow or birch.
  • the wood-based raw material may also be any combination or mixture of these.
  • compositions of the disclosure may be obtained by any suitable means known in the art.
  • the compositions may be prepared by mixing the glycol compounds in the desired quantities.
  • a composition of the disclosure is obtained via a process comprising catalytic hydrogenolysis of a carbohydrate composition.
  • the composition is obtained by a process which comprises: contacting a carbohydrate composition with hydrogen in a reactor in the presence of water and a catalyst under conditions such that the carbohydrate composition undergoes catalytic hydrogenolysis to produce an aqueous mixture comprising monopropylene glycol, monoethylene glycol and 2,3-pentanediol; subjecting the aqueous mixture to a distillation procedure such that a portion of the monoethylene glycol is removed from the aqueous mixture, thereby forming a first fraction comprising monopropylene glycol and 2,3-pentanediol and a second fraction comprising purified monoethylene glycol; subjecting the first fraction to a distillation procedure and recovering the composition of the disclosure therefrom as a product.
  • a carbohydrate composition comprising a particular combination of sugars.
  • the carbohydrate composition comprises glucose, xylose and one or more sugars selected from galactose, arabinose, mannose and fructose. More preferably, the carbohydrate composition comprises each of glucose, xylose, galactose, arabinose, mannose and fructose.
  • the amounts of the sugars in the carbohydrate composition may be expressed as a percentage by weight of the total dry matter content of the carbohydrate composition.
  • total dry matter content refers to the total amount of solids including suspended solids and soluble or dissolved solids in the carbohydrate composition.
  • the total dry matter content may be determined after removing the liquid from a sample followed by drying at a temperature of 105 °C for 24 hours. The effectiveness of the liquid removal may be assured by weighing the sample, drying for a further two hours at the specified temperature, and reweighing the sample. If the measured weights are the same, the drying has been complete, and the total weight may be recorded.
  • the carbohydrate composition comprises from 90% to 95% by weight of glucose; from 4% to 8% by weight of xylose; from 0.1% to 1% by weight of galactose; from 0.1% to 1% by weight of arabinose; from 0.1% to 1% by weight of mannose; and from 0.1% to 2% by weight of fructose, wherein said amounts are based on the total dry matter content of the carbohydrate composition.
  • sugars may exist in monomeric and oligomeric forms.
  • the term "monomeric” as used herein refers to a sugar molecule that is not coupled or connected to any other sugar molecule(s). Monomeric sugars are also known as monosaccharides.
  • oligomeric refers to a sugar molecule consisting of two or more monomers coupled or connected to each other. Examples of oligomeric sugars include disaccharides and trisaccharides.
  • the carbohydrate composition has a total monomeric sugar content of at least 90% by weight based on the total dry matter content of the carbohydrate composition. More preferably, the monomeric sugar content of the carbohydrate composition is at least 94% by weight, for example at least 95% by weight, based on the total dry matter content of the carbohydrate composition.
  • the carbohydrate composition is obtained from a wood-based raw material, such as hardwood or softwood.
  • wood-based raw materials are composed essentially of cellulose, hemicellulose, lignin, and extractives.
  • Cellulose is a polysaccharide consisting of a chain of glucose units.
  • Hemicellulose comprises polysaccharides, such as xylan, mannan, and glucan.
  • the wood-based raw material may originate from, e.g., pine, poplar, beech, aspen, spruce, eucalyptus, ash, oak, maple, chestnut, willow or birch.
  • the wood-based raw material may also be any combination or mixture of these.
  • the carbohydrate composition may be prepared by a process comprising: subjecting a wood-based feedstock comprising wood chips to at least one pretreatment to form a liquid fraction and a fraction comprising solid cellulose particles; and subjecting the fraction comprising solid cellulose particles to enzymatic hydrolysis to form a lignin fraction and a carbohydrate fraction.
  • the carbohydrate fraction may be optionally purified and then used as the carbohydrate composition in the catalytic hydrogenolysis process.
  • pretreating and pretreatment refer to a process conducted to convert a wood-based feedstock to a fraction comprising solid cellulose particles.
  • a liquid fraction may be formed.
  • the liquid fraction may be separated from the fraction comprising solid cellulose particles.
  • the fraction comprising solid cellulose particles may further include an amount of lignocellulose particles as well as lignin particles in free form.
  • Lignocellulose comprises lignin chemically bonded to the cellulose particles.
  • the wood-based feedstock may be provided by subjecting a wood-based raw material to a mechanical treatment selected from debarking, chipping, dividing, cutting, beating, grinding, crushing, splitting, screening, and/or washing to form the wood-based feedstock.
  • a mechanical treatment selected from debarking, chipping, dividing, cutting, beating, grinding, crushing, splitting, screening, and/or washing to form the wood-based feedstock.
  • the wood-based feedstock may be purchased.
  • Pretreatment of the wood-based feedstock may comprise one or more different pretreatment processes. During the different pretreatment processes the wood-based feedstock as such changes.
  • the aim of the at least one pretreatment processes is to form a fraction comprising solid cellulose particles for further processing.
  • the pretreatment may comprise subjecting the wood-based feedstock to pre-steaming.
  • the pretreatment may comprise subjecting the wood-based feedstock received from the mechanical treatment to pre-steaming.
  • the pretreatment may comprise an impregnation treatment and/or a steam explosion and comprise, before subjecting the wood-based feedstock to impregnation treatment and/or to steam explosion, subjecting the wood-based feedstock to pre-steaming, wherein the pre-steaming of the wood-based feedstock is carried out with steam having a temperature of from 100 to 130 °C at atmospheric pressure. During the pre-steaming the wood-based feedstock is treated with steam of low pressure.
  • the pre-steaming may be also carried out with steam having a temperature of below 100 °C, or below 98 °C, or below 95 °C.
  • the pre-steaming has the added utility of reducing or removing air from inside of the wood-based feedstock.
  • the pre-steaming may take place in at least one pre-steaming reactor.
  • a pre-steaming reactor is operationally arranged before the impregnation reactor and/or the pressurised reactor and configured to subject the wood-based feedstock to presteaming with steam having a temperature of from 100 to 130 °C at atmospheric pressure.
  • Pretreatment may also comprise subjecting the wood-based feedstock to at least one impregnation treatment with an impregnation liquid.
  • the impregnation treatment may be carried out to the wood-based feedstock received from the mechanical treatment and/or from the pre-steaming.
  • the pretreatment may comprise, before subjecting to the steam explosion, subjecting the wood-based feedstock to at least one impregnation treatment with an impregnation liquid selected from water, at least one acid, at least one alkali, at least one alcohol, or any combination or mixture thereof.
  • the impregnation liquid may comprise water, at least one acid, at least one alkali, at least one alcohol, or any combination or mixture thereof.
  • the at least one acid may be selected from a group consisting of inorganic acids, such as sulphuric acid (H2SO4), nitric acid, phosphoric acid; organic acids, such as acetic acid, lactic acid, formic acid, carbonic acid; and any combination or mixture thereof.
  • the impregnation liquid comprises sulphuric acid, e.g. dilute sulphuric acid.
  • the concentration of the acid may be from 0.3% to 5.0% by weight, from 0.5% to 3.0% by weight, from 0.6% to 2.5% by weight, from 0.7% to 1.9% by weight, or from 1.0% to 1.6% by weight.
  • the impregnation liquid may act as a catalyst for the hydrolysis of the hemicellulose in the wood-based feedstock. In one embodiment, the impregnation is conducted by using only water, i.e. by autohydrolysis. In one embodiment, the wood-based feedstock may be impregnated through alkaline hydrolysis. NaOH and Ca2(OH)3 can be mentioned as examples to be used as the alkali in the alkaline hydrolysis.
  • the impregnation treatment may be performed using an impregnation reactor configured to subject the wood-based feedstock to at least one impregnation treatment with an impregnation liquid.
  • the impregnation reactor may be configured to subject the woodbased feedstock to at least one impregnation treatment with an impregnation liquid selected from water, at least one acid, at least one alcohol, or any combination or mixture thereof.
  • the impregnation treatment may thus be conducted in at least one impregnation reactor or vessel. In one embodiment, two or more impregnation reactors are used.
  • the impregnation treatment may be carried out by conveying the wood-based feedstock through at least one impregnation reactor, i.e. the wood-based feedstock may be transferred into the impregnation reactor, interspersed inside the impregnation reactor, and transferred out of the impregnation reactor such that the wood-based feedstock is homogenously impregnated with the impregnation liquid.
  • the impregnation treatment may be carried out as a batch process or in a continuous manner.
  • Pretreatment may comprise subjecting the wood-based feedstock to steam explosion.
  • steam explosion refers to a process of hemihydrolysis in which the wood-based feedstock is treated in a reactor with steam under conditions which result in a sudden, explosive decompression of the wood-based feedstock that causes rupture of the fiber structure of the wood-based feedstock.
  • the steam explosion process may be conducted in a pressurized reactor.
  • the steam explosion may be carried out in the pressurized reactor by treating the wood-based feedstock with steam having a temperature of from 130 to 240 °C under a pressure of from 0.17 to 3.25 MPaG followed by a sudden, explosive decompression of the wood-based feedstock.
  • the wood-based feedstock may be treated with the steam for e.g. from 1 to 20 minutes, from 2 to 16 minutes, from 4 to 13 minutes, from 3 to 10 minutes, or from 3 to 8 minutes, before the sudden, explosive decompression of the wood-based feedstock.
  • the wood-based feedstock may be introduced into the pressurized reactor with a compressing conveyor, e.g. a screw feeder.
  • part of the impregnation liquid absorbed by the wood-based feedstock is removed as a pressate while some of it remains in the feedstock.
  • the wood-based feedstock may be introduced into the pressurized reactor along with steam and/or gas.
  • the pressure of the pressurized reactor can be controlled by the addition of steam.
  • the pressurized reactor may operate in a continuous manner or as a batch process.
  • the wood-based feedstock for example the wood-based feedstock that has been subjected to an impregnation treatment, may be introduced into the pressurized reactor at a temperature of from 25 to 140 °C.
  • the residence time of the wood-based feedstock in the pressurized reactor may be from 0.5 to 120 minutes.
  • the term "residence time" as used in this context refers to the time between the wood-based feedstock being introduced into or entering the pressurized reactor and the wood-based feedstock being exited or discharged from the same.
  • the water containing C5 sugars may be recycled water from separation and/or washing the fraction comprising solid cellulose particles before enzymatic hydrolysis.
  • the output stream may be mixed with the liquid and the resulting mass may be homogenized mechanically to break up agglomerates.
  • the method may comprise separating and recovering the liquid fraction and the fraction comprising solid cellulose particles.
  • the separated or recovered fraction comprising solid cellulose particles may be washed before being subjected to enzymatic hydrolysis.
  • the fraction comprising solid cellulose particles may be diluted with water and/or other liquid containing at least soluble carbohydrates.
  • the enzymatic hydrolysis is carried out at a temperature of from 30 to 70 °C, from 35 to 65 °C, from 40 to 60 °C, from 45 to 55 °C, or from 48 to 53 °C while keeping the pH of the fraction comprising solid cellulose particles at a pH value of from 3.5 to 6.5, from 4.0 to 6.0, or from 4.5 to 5.5, and wherein the enzymatic hydrolysis is allowed to continue for from 20 to 120 h, from 30 to 90 h, or from 40 to 80 h.
  • the enzymatic hydrolysis may be carried out as a two-step hydrolysis process or as a multi-step hydrolysis process.
  • the fraction comprising solid cellulose particles may first be subjected to a first enzymatic hydrolysis in at least one first hydrolysis reactor.
  • the formed liquid carbohydrate fraction may be separated from the solid lignin fraction, which may also comprise unhydrolyzed cellulose.
  • the solid fraction may then be subjected to a second or any latter enzymatic hydrolysis, e.g. in at least one second hydrolysis reactor.
  • the enzymes are catalysts for the enzymatic hydrolysis.
  • the enzymatic reaction decreases the pH and by shortening the length of the cellulose fibers it may also decrease the viscosity.
  • Subjecting the fraction comprising solid cellulose particles to enzymatic hydrolysis may result in cellulose being transformed into sugar monomers with enzymes. Lignin present in the fraction comprising solid cellulose particles may remain essentially in solid form.
  • At least one enzyme is used for carrying out the enzymatic hydrolysis.
  • the at least one enzyme may be selected from a group consisting of cellulases, hemicellulases, laccases, and lignolytic peroxidases.
  • Enzymatic hydrolysis may result in the formation of a lignin fraction and a carbohydrate fraction.
  • the lignin fraction is in solid form.
  • the carbohydrate fraction is in liquid form. The lignin fraction and the carbohydrate fraction formed may be separated and recovered before conducting the catalytic conversion.
  • Separation(s) conducted during the preparation process may be carried out by filtration and/or by centrifugal treatment.
  • the filtration may be vacuum filtration, filtration based on the use of underpressure, filtration based on the use of overpressure, or filter pressing.
  • the carbohydrate composition is obtained from a wood-based raw material
  • sugars obtained from other sources may also be used in the catalytic hydrogenolysis process.
  • a carbohydrate composition derived from corn starch may be used.
  • the catalytic conversion process involves contacting the carbohydrate composition with hydrogen in a reactor in the presence of water and a catalyst under conditions such that the carbohydrate composition undergoes catalytic hydrogenolysis to produce an aqueous mixture comprising monopropylene glycol, monoethylene glycol and 2,3-pentanediol.
  • the catalytic conversion may be carried out in the presence of a catalyst system comprising one or more catalysts.
  • the catalyst system comprises or consists of a first catalyst.
  • the catalyst system comprises or consists of at least a first catalyst and at least a second catalyst.
  • the catalyst system comprises or consists of a first catalyst and a second catalyst.
  • the first catalyst may be a heterogenous, solid catalyst.
  • the second catalyst may be a homogenous catalyst.
  • the first and second catalysts may be heterogenous catalysts e.g. supported on a carrier.
  • composition of the disclosure may then be recovered from the first fraction by subjecting the first fraction to a distillation procedure.
  • a “theoretical stage”, a “theoretical plate” or a “distillation stage” as it may also be called can be considered as a hypothetical zone or stage in which two phases, such as the liquid and vapor phases of a substance, establish an equilibrium with each other. Such equilibrium stages may also be referred to as an equilibrium stage, ideal stage, or a theoretical tray.
  • the distillation solvent is a diol or a sugar alcohol having a boiling point that is at least 80 °C higher than the boiling point of monopropylene glycol at atmospheric pressure.
  • the distillation solvent may have a boiling point that is at least 85 °C, or at least 90 °C, higher than the boiling point of monopropylene glycol at atmospheric pressure.
  • the distillation solvent may have a boiling point that is from 80 to 100 °C, from 82 to 98 °C, or from 85 to 95 °C, higher than the boiling point of monopropylene glycol at atmospheric pressure.
  • the distillation solvent may have a boiling point of from 265 to 350 °C, from 265 to 300 °C, or from 275 to 300 °C.
  • the distillation solvent is a diol having a boiling point that is at least 80 °C higher than the boiling point of monopropylene glycol at atmospheric pressure.
  • the mixture feed may be fed into the first distillation column at a point which is below the point at which the distillation solvent is fed into the first distillation column.
  • the mixture feed may be fed into the first distillation column at a point which is situated below, above, or on at least one theoretical stage.
  • the mixture feed may be fed on a theoretical stage or above a theoretical stage.
  • the distillation solvent is fed into the first distillation column at any point between 1st and 10th, or 2nd and 9th, or 3rd and 7th, theoretical stages as calculated from the top of the first distillation column.
  • the distillation solvent may be fed into the first distillation column above the topmost theoretical stage as calculated from the top of the first distillation column.
  • the first distillation process is carried out at a top temperature of from 75 to 135 °C, or from 90 to 130 °C, or from 100 to 120 °C.
  • the first distillation process is carried out at a bottom temperature of from 150 to 230 °C, or from 160 to 200 °C, or from 170 to 190 °C.
  • the pressure drop over the distillation column is from 0.05 to 0.2 bar, or from 0.07 to 0.15 bar, or from 0.08 to 0.1 bar.
  • the residence time of the mixture feed and the distillation solvent in the first distillation column is from 1 to 10 minutes, or from 1.2 to 7 minutes, or from 1.5 to 6 minutes, or from 1.8 to 5.4 minutes.
  • the bottom temperature of the first distillation column may be kept at a temperature of at most 230 °C. Maintaining the bottom temperature of the distillation column at a temperature of at most 230 °C has the added utility of hindering or reducing compound degradation to take place.
  • top temperature refers to the temperature at the vapor space in the distillation column that is above the topmost packed bed or stage and below the vapor pipe of the distillation column. It is clear to the person skilled in the art that the temperature in the distillation column as such may differ from the temperature in e.g. the condenser or the reboiler that may be operationally connected to the distillation column.
  • bottom temperature refers to the temperature of the liquid in the column sump.
  • top pressure refers to the pressure at the vapor space in the distillation column that is above the topmost packed bed or stage and below the vapor pipe of the distillation column.
  • At least one condenser is used in the distillation process.
  • the distillation arrangement comprises at least one condenser.
  • the condenser(s) used may be selected from partial condensers, total condensers and combinations thereof.
  • the condenser(s) may be heat integrated or they may use a cooling medium, such as cooling water, or they may function with air cooling.
  • a reboiler is used in the distillation process.
  • the distillation arrangement comprises a reboiler.
  • the reboiler may be operated at a vapor pressure of from 0.06 to 0.4 bar, or from 0.1 to 0.2 bar.
  • the process comprises: removing impurities together with the distillation solvent in a bottom stream from the first distillation column; and removing monopropylene glycol and 2,3-pentanediol in a top stream from the first distillation column.
  • the process comprises recycling the distillation solvent removed in the bottom stream from the first distillation process back into the first distillation column.
  • the distillation solvent may be led into a recovery column.
  • lighter components may be removed in a top stream from the recovery column and the distillation solvent may be removed in a bottom stream from the recovery column.
  • the bottom stream comprising mainly the distillation solvent may then be led back into the first distillation column and thus reused. If needed, a part of the recycled flow of distillation solvent may be continuously purged in order to reduce or limit the accumulation of heavier degradation compounds if these appear.
  • the process comprises providing the monopropylene glycol and 2,3- pentanediol removed in a top stream from the first distillation process into a second distillation column, wherein a second distillation process is carried out.
  • the second distillation process is carried out at a top temperature of from 104 to 140 °C, or from 90 to 130 °C, or from 100 to 120 °C.
  • the second distillation process is carried out at a bottom temperature of from 134 to 170 °C, or from 145 to 165 °C, or from 150 to 160 °C.
  • the second distillation process is carried out at a top pressure of from 0.1 to 0.5 bar.
  • compositions of the disclosure exhibit desirable properties and may be used in various applications.
  • bio-based compositions described herein may be used as a low carbon footprint alternative to fossil-based monopropylene glycol compositions.
  • compositions of the disclosure are liquid compositions.
  • the compositions are liquid at standard ambient temperature and pressure (1.013 bar, 25 °C).
  • compositions find particular application in the manufacture of polymers.
  • polyesters are typically prepared by the condensation polymerisation of glycols with dicarboxylic acids or their derivatives, while polyurethanes are typically prepared by reacting glycols with diisocyanates.
  • the compositions of the disclosure may therefore be used as a source of glycol monomers for the preparation of these and other polymers.
  • the resulting polymers may have characteristic structures and properties due to the specific glycols present in the compositions.
  • the composition has an electrical conductivity of less than 0.01 pS/cm, more preferably less than 0.002 pS/cm, even more preferably less than 0.001 pS/cm.
  • the electrical conductivity can be measured using a conductivity meter such as a SevenExcellence S700 conductivity meter (Mettler Toledo). The electrical conductivity is measured at a temperature of 25 °C.
  • compositions may also be used in other applications.
  • the compositions may be used in coolant and heat transfer fluids, de-icing agents, food products, pharmaceutical compositions, cosmetic compositions and detergent compositions.
  • the low electrical conductivity of the compositions renders them especially useful in fluids for cooling systems, such as those used in data centers, electronics, and industrial machinery, for which it is important to minimise the risk of electrical damage to sensitive components and circuits.
  • GC Gas chromatography
  • RRF relative response factors
  • the amounts of the individual components in the composition are determined in area percent (Ar.%).
  • the corresponding RRF values are applied using the following equation: (100 - Water [Wt. %]
  • RRF Retention times (RT), relative retention times (RRT; relative to monopropylene glycol) and RRF values for selected components are given in the table below (an RRF value of 1 is used for any unknown components):
  • a sample of the glycol mixture was analysed using the methods described in Example 1.
  • the composition of the sample was determined to be as follows:
  • a feedstock comprising hardwood chips was pretreated and then subjected to an enzymatic hydrolysis procedure as described herein to produce a carbohydrate composition.
  • a sample of the carbohydrate composition was analysed and found to contain mainly (>89 wt%) glucose, as well as minor amounts of xylose, galactose, arabinose, mannose and fructose.
  • the distillation process was performed in two steps.
  • the first step was an extractive distillation step in which mainly monoethylene glycol and other heavy boiling components were removed in the bottom product.
  • the extracting agent used in the first step contained 99.4 wt% triethylene glycol (TEG), 0.5 wt% diethylene glycol and 0.1 wt% water.
  • TOG triethylene glycol
  • the second step the distillate of the first step was further processed and the low boiling components were removed as the distillate.
  • the final product was separated as a side draw.
  • the experiments were performed on a distillation column with an inner diameter of 250 mm and with structured packing as internals for both steps.
  • the column was equipped with 3.86 m of structured packing below the feed position.
  • the column was equipped with 3.54 m of structured packing between the feed position and the TEG feed position.
  • An additional 0.96 m structured packing was used above the TEG feed position.
  • the column was equipped with 3.54 m structured packing below the feed position and 2.57 m of structuring packing above the feed position.
  • the liquid side draw was 1.12 m above the bottom vessel.
  • CYPIusTM structured packing was used in all cases.
  • the first distillation step was conducted under the following conditions: Monoethylene glycol was removed in the bottom product and in all distillate samples the monoethylene glycol concentration was ⁇ 1 wt.-%.
  • the second distillation step was conducted under the following conditions:
  • the sample was found to have the following composition:
  • Example 4 The product of Example 4 and a fossil-based monopropylene glycol composition (>99.5% MPG; obtained from Carl Roth GmbH & Co. KG) were evaluated for various physical and chemical properties. A comparison of their properties is presented in the following table:

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Abstract

La présente invention concerne une composition comprenant du monopropylène glycol et du 2,3-pentanediol, le monopropylène glycol étant présent en une quantité d'au moins 98,0 % en poids de la composition. Les compositions de l'invention ont des propriétés souhaitables et peuvent être utilisées en tant qu'alternative à faible empreinte carbone pour les compositions de glycol d'origine fossile dans diverses applications.
PCT/EP2025/057501 2024-03-25 2025-03-19 Compositions de monopropylène glycol Pending WO2025201986A1 (fr)

Applications Claiming Priority (2)

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FI20245334A FI20245334A1 (en) 2024-03-25 2024-03-25 MONOPROPYLENE GLYCOL COMPOSITIONS
FI20245334 2024-03-25

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WO2025201986A1 true WO2025201986A1 (fr) 2025-10-02

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