WO2024089647A1 - Configuration de procédé pour la production d'alcool isopropylique - Google Patents

Configuration de procédé pour la production d'alcool isopropylique Download PDF

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Publication number
WO2024089647A1
WO2024089647A1 PCT/IB2023/060820 IB2023060820W WO2024089647A1 WO 2024089647 A1 WO2024089647 A1 WO 2024089647A1 IB 2023060820 W IB2023060820 W IB 2023060820W WO 2024089647 A1 WO2024089647 A1 WO 2024089647A1
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Prior art keywords
isopropyl alcohol
storage tank
gas
crude
reactor
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PCT/IB2023/060820
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English (en)
Inventor
Robert BROEKHUIS
Flaiyh Farhan N. AL-ANAZI
Talal Khaled AL-SHAMMARI
Andrei Merenov
Vinodkumar Vasudevan
Khalid AL-AHAMADI
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Sabic Global Technologies B.V.
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Publication of WO2024089647A1 publication Critical patent/WO2024089647A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/143—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones
    • C07C29/145—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones with hydrogen or hydrogen-containing gases
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
    • C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment

Definitions

  • the present disclosure relates to the production of isopropyl alcohol. More specifically, the disclosure relates to systems and processes for the production of isopropyl alcohol via acetone hydrogenation.
  • Isopropyl alcohol or isopropanol has an array of industrial applications and is useful in the manufacture of many chemicals including isopropyl amine and a variety of ethers.
  • For the hydrogenation of acetone typically an acetone containing feedstream is contacted with hydrogen in the presence of a hydrogenation catalyst to produce a crude product.
  • the hydrogenation of acetone feedstream in the reactor generates a crude IPA stream at a high flow rate and high temperature.
  • the present disclosure provides processes, apparatuses, and systems for the production of a purified isopropyl alcohol product. Integrated processes of acetone hydrogenation are described. Aspects of the present disclosure allow for a generated crude isopropyl alcohol product to be stored and ultimately isolated and purified. Further aspects may incorporate recycling of generated light ends and hydrogen gas streams to more efficiently conduct acetone hydrogenation.
  • the disclosed processes and systems featuring a storage vessel, liquid recycle, and gas-liquid separators may enable flexible operation modes as well as the capacity to mitigate process disruptions with minimal impact on anticipated production capacities.
  • a method of producing a purified isopropyl alcohol product may comprise reacting acetone and hydrogen in the presence of a solid catalyst in an adiabatic reactor to provide a reactor effluent comprising crude isopropyl alcohol and hydrogen.
  • the reactor effluent may be directed to a gas-liquid separator to provide a crude isopropyl alcohol.
  • At least a first portion of the crude isopropyl alcohol may be directed to the adiabatic reactor.
  • At least a portion of the crude isopropyl alcohol may be directed to a storage tank to provide an isolated crude isopropyl alcohol.
  • the isolated crude isopropyl alcohol may be directed from the storage tank (a) to the adiabatic reactor or (b) to one or more separation processes to yield a purified isopropyl alcohol product.
  • a method of producing a purified isopropyl alcohol product may comprise (a) directing a liquid reactor feed comprising acetone and a hydrogen feed to a single gas-liquid reactor comprising a solid catalyst to form a reactor effluent comprising isopropyl alcohol, wherein the acetone is present in the liquid reactor feed in an amount from 5% to 15% by weight, (b) directing at least a first fraction of the reactor effluent comprising isopropyl alcohol to a gas-liquid separator to separate a gaseous stream comprising hydrogen and a cmde isopropyl alcohol stream; (c) directing at least a fraction of the crude isopropyl alcohol stream to the single gas-liquid reactor; (d) directing at least another fraction of the crude isopropyl alcohol stream to a storage tank to provide a stored crude isopropyl alcohol; and (e) directing at least a fraction of the stored crude isopropyl alcohol from the storage tank to one or more
  • the present disclosure relates to further systems and processes that facilitate the method of acetone hydrogenation described herein.
  • Embodiment 1 A method of producing a purified isopropyl alcohol product, the method comprising: directing a liquid reactor feed comprising acetone and a hydrogen feed to a single gas-liquid reactor comprising a solid catalyst to form a reactor effluent comprising isopropyl alcohol; directing the reactor effluent comprising isopropyl alcohol to at least one gas-liquid separator to separate a gaseous stream comprising hydrogen and a crude isopropyl alcohol stream; directing at least a fraction of the crude isopropyl alcohol stream to the single gas-liquid reactor; directing at least another fraction of the crude isopropyl alcohol stream to an intermediate storage tank to provide a stored crude isopropyl alcohol; accumulating crude isopropyl alcohol in the intermediate storage tank until the crude isopropyl alcohol fills at least 20% by volume of the intermediate storage tank; and after the crude isopropyl alcohol fills at least 20% by volume of the intermediate storage tank, directing at least a fraction
  • Embodiment 2 The method of Embodiment 1, wherein accumulating crude isopropyl alcohol in the intermediate storage tank comprises accumulating crude isopropyl alcohol until the crude isopropyl alcohol fills at least 30%, at least 40%, at least 50%, at least 60%, at least 70%, at least 80%, at least 85%, at least 90%, at least 95%, or at least 98% by volume of the intermediate storage tank.
  • Embodiment 3 The method of Embodiment 1 or 2, wherein the intermediate storage tank is maintained at a temperature sufficiently low to suppress isopropyl alcohol vapor pressure, such as a temperature below 40 °C, below 30 °C, or below 25 °C, and/or wherein a non-flammable inert gas atmosphere is present in a head space of the intermediate storage tank.
  • a temperature sufficiently low to suppress isopropyl alcohol vapor pressure such as a temperature below 40 °C, below 30 °C, or below 25 °C, and/or wherein a non-flammable inert gas atmosphere is present in a head space of the intermediate storage tank.
  • Embodiment 4 The method of any one of Embodiments 1-3, wherein the intermediate storage tank does not receive a gaseous effluent from the at least one gas-liquid separator.
  • Embodiment 5 The method of any one of Embodiments 1-4, further comprising directing the crude isopropyl alcohol stream to a second storage tank downstream from the at least one gas-liquid separator, and wherein the directing at least a fraction of the crude isopropyl alcohol stream to the single gas-liquid reactor comprises directing crude isopropyl alcohol from the second storage tank to the single gas-liquid reactor.
  • Embodiment 6 The method of any one of Embodiments 1-5, wherein the directing at least another fraction of the crude isopropyl alcohol stream to the intermediate storage tank to provide a stored crude isopropyl alcohol comprises directing crude isopropyl alcohol from the second storage tank to the intermediate storage tank.
  • Embodiment 7 The method of any one of Embodiments 1-6, wherein the at least one gas-liquid separator comprises a high pressure gas-liquid separator, optionally operating at a pressure of 15-30 bar, and a low pressure gas-liquid separator downstream from the high pressure gas-liquid separator, optionally operating at a pressure of from 1 bar to about 6 bar.
  • the at least one gas-liquid separator comprises a high pressure gas-liquid separator, optionally operating at a pressure of 15-30 bar, and a low pressure gas-liquid separator downstream from the high pressure gas-liquid separator, optionally operating at a pressure of from 1 bar to about 6 bar.
  • Embodiment 8 The method of any one of Embodiments 1-7, further comprising directing the gaseous stream comprising hydrogen from the at least one gas-liquid separator to a condenser to separate a hydrogen-rich gas from condensed crude isopropyl alcohol.
  • Embodiment 9 The method of any one of Embodiments 1-8, characterized by one or more of the following: the acetone is present in the liquid reactor feed in an amount from 5% to 15% by weight; the liquid reactor feed has a water content of less than 1%, such as less than 0.5%, less than 0.1%, or less than 0.005%; the single gas-liquid reactor is adiabatic and has an inlet to outlet temperature differential of 15 °C to 40 °C; the crude isopropyl alcohol stream contains less than 0.5 wt.
  • the single gasliquid reactor operates at a pressure of from 5 to 40 bar; the single gas-liquid reactor operates at a temperature from 60 °C to 200 °C, such as from 60 °C to 120 °C, or from 70 °C to 140 °C; a molar ratio of hydrogen to acetone in the single gas-liquid reactor is maintained at 1 : 1 to 1.5 : 1 ; the solid catalyst comprises copper or nickel; the single gas-liquid reactor achieves an acetone conversion of at least 95 %; at least 80%, such as 80-95%, of the crude isopropyl alcohol is directed to the single gas-liquid reactor; and the one or more separation processes comprises directing at least a fraction of the stored crude isopropyl alcohol from the intermediate storage tank to a first separation column to yield at least a first light end and an intermediate isopropyl alcohol product, and directing the intermediate isopropyl alcohol to a second separation column to yield a second light end and a purified isopropyl alcohol product
  • Embodiment 10 A system for producing a purified isopropyl alcohol product, the system comprising: a single gas-liquid reactor comprising a solid catalyst in fluid communication with a liquid reactor feed comprising acetone and a hydrogen feed, the single gas-liquid reactor adapted to produce a reactor effluent comprising isopropyl alcohol; at least one gas-liquid separator adapted to separate a gaseous stream comprising hydrogen and a crude isopropyl alcohol stream, and in fluid communication with the reactor effluent comprising isopropyl alcohol, wherein at least a fraction of the crude isopropyl alcohol stream is in fluid communication with the single gas-liquid reactor; an intermediate storage tank in fluid communication with a fraction of the crude isopropyl alcohol stream to provide a stored crude isopropyl alcohol, wherein the intermediate storage tank is adapted to accumulate crude isopropyl alcohol until the crude isopropyl alcohol fills at least 20% by volume of the intermediate storage tank, such as at least 30%, at least 40%
  • Embodiment 11 The system of Embodiment 10, wherein the intermediate storage tank is temperature controlled to suppress isopropyl alcohol vapor pressure, and/or wherein a non-flammable inert gas atmosphere is present in a head space of the intermediate storage tank.
  • Embodiment 12 The system of Embodiment 10 or 11, further comprising a second storage tank in fluid communication with the at least one gas-liquid separator and adapted to receive the crude isopropyl alcohol stream, wherein the second storage tank is in fluid communication with the single gas-liquid reactor for recycle of crude isopropyl alcohol.
  • Embodiment 13 The system of any one of Embodiments 10-12, wherein the second storage tank is in fluid communication with the intermediate storage tank and adapted to direct crude isopropyl alcohol to the intermediate storage tank.
  • Embodiment 14 The system of any one of Embodiments 10-13, further comprising a condenser adapted to separate a hydrogen-rich gas from condensed crude isopropyl alcohol and in fluid communication with the gaseous stream comprising hydrogen from the at least one gas-liquid separator.
  • Embodiment 15 The system of any one of Embodiments 10-14, wherein the at least one gasliquid separator comprises a high pressure gas-liquid separator, optionally adapted to operate at a pressure of 15-30 bar, and a low pressure gas-liquid separator downstream from the high pressure gas-liquid separator and in fluid communication with the high pressure gas-liquid separator, optionally adapted to operate at a pressure of from 1 bar to about 6 bar.
  • the at least one gasliquid separator comprises a high pressure gas-liquid separator, optionally adapted to operate at a pressure of 15-30 bar, and a low pressure gas-liquid separator downstream from the high pressure gas-liquid separator and in fluid communication with the high pressure gas-liquid separator, optionally adapted to operate at a pressure of from 1 bar to about 6 bar.
  • FIG. 1 shows a reaction scheme for hydrogenation of acetone.
  • FIG. 2 shows a schematic diagram of an acetone hydrogenation system in accordance with an embodiment of the present disclosure with hydrogen and cmde IPA recycle.
  • FIG. 3 shows a schematic diagram of an acetone hydrogenation system in accordance with an embodiment of the present disclosure with a condenser for gas-liquid phase separation.
  • FIG. 4 shows a schematic diagram of an acetone hydrogenation system in accordance with an embodiment of the present disclosure with a condenser for gas-liquid phase separation and recycle of light ends.
  • Acetone hydrogenation is a highly exothermic reaction that presents a challenge to maintain an acceptable temperature range and high flow rate.
  • the high flow rate and high exothermicity may complicate further purification of the crude IPA stream and may require elaborate alterations in the separation unit of the reactor system, thereby increasing the cost of running the separation column.
  • the processes and systems of the present disclosure mitigate the difficulties caused by the exothermic nature and high flow rate of the hydrogenation reaction system.
  • An acetone containing feedstream may be contacted with hydrogen in the presence of a hydrogenation catalyst to produce a crude product.
  • a process for production of IPA via hydrogenation of acetone The hydrogenation of feedstream in the reactor may generate a crude IPA stream having extremely high flow rate and high temperature.
  • the disclosed hydrogenation may proceed in a trickle-bed reactor to form a crude IPA.
  • Acetone and recycled crude IPA diluent may be introduced to a hydrogenation reactor equipped with heterogeneous catalyst in the presence of hydrogen gas.
  • An effluent comprising cmde IPA may be fed from the reactor to a gas-liquid separator to separate hydrogen gas and non-condensable gases (including IPA and acetone vapors) from the crude IPA.
  • a stream of hydrogen gas and non-condensable gasses may be further separated into the respective gases.
  • the hydrogen gas stream may be recycled to the hydrogenation reactor while other gases may proceed to a flare or fuel system.
  • a second stream comprising crude IPA may be divided as a recycled stream to the hydrogenation reactor and as a stored stream that is transferred to a storage tank.
  • Crude IPA from the storage tank(s) may then be supplied as feed to a fractionation section, which may comprise separation columns, for further purification.
  • Light ends and heavy ends may be separated from crude IPA to yield a purified IPA product in the separation columns.
  • Light ends, heavy ends (residue) and purified IPA product may be transferred to respective storage tanks.
  • a storage tank as used herein may refer to as an “internal” storage tank where the tank is configured to be within the recycle loop for the reactor system or an “intermediate” storage tank where the tank is configured to store crude IPA for downstream purification processes. As such, the contents of the storage tank may be for recycle or for downstream purification. It has been found that the incorporation of the storage tank(s) to the reactor system as well as the incorporation of the hydrogen recycle stream may optimize system performance. Stored crude IPA may arrest the flow rate of the crude IPA flow streams. The storage tank(s) thus allows for an inventory of crude IPA to build in the system for downstream separation or reagent recycle. Liquid recycle in the reactor system and heat exchange strategies for the high and low pressure gas-liquid separators downstream of the reactor further enhance efficiency of the disclosed reactor system.
  • the present disclosure provides processes and systems for the hydrogenation of acetone.
  • the process may comprise combining hydrogen and acetone in a reactor with a hydrogenation catalyst and IPA as a solvent to form crude IPA.
  • the crude IPA may be directed through a gas-liquid separation chamber to remove unreacted hydrogen and other gases.
  • the isolated crude IPA may be directed to a storage tank configured to accumulate a stored inventory of the crude IPA to further propagate the acetone hydrogenation reaction.
  • the stored crude IPA may be subjected to one or more separation processes to provide a purified IPA product.
  • a number of recycling streams may accompany the foregoing processes. For example, at least a fraction of crude IPA from the gas-liquid separation chamber may be directed to the initial acetone hydrogenation reactor.
  • a feed stream comprising acetone may be subjected to a hydrogenation process in the presence of a catalyst and hydrogen in a reactor to form a crude IPA.
  • Acetone may be present in the reactor feed in an amount from about 5% to about 20% by volume.
  • At least a first fraction of the crude IPA may be directed to a gas-liquid separator to separate gases from an effluent comprising IPA.
  • At least a fraction of the effluent from the gas-liquid separator may be recycled to the hydrogenation reactor.
  • At least another fraction of the effluent from the gas-liquid separator may be directed to a storage tank to provide the system a volume of stored crude IPA.
  • At least a portion of this stored crude IPA may be subjected to one or more separation processes to yield a purified IPA product.
  • the process comprises a recycle stream of IPA such that the IPA is a diluent for reagent acetone in the hydrogenation reactor.
  • directing at least a fraction of the effluent from the gas-liquid separator to the reactor comprises directing at least about 80-95% of the IPA to the hydrogenation reactor.
  • the integrated processes disclosed herein may comprise a gas-liquid phase hydrogenation. More specifically, the integrated processes and systems may comprise a gas-liquid hydrogenation of acetone to IPA.
  • a feed stream comprising acetone may be converted via a hydrogenation process to form at least crude IPA. At least a portion of generated isopropyl alcohol may be retained for further processing and recycle via the use of an intermediate storage tank.
  • isopropyl alcohol from acetone generates significant amounts of heat.
  • the conversion is a well known process and has been presented in a number of patents and publications.
  • Catalytic hydrogenation of acetone to isopropyl alcohol is a reversible reaction.
  • Potential side reactions may include the formation of diacetone alcohol (DAA), mesityl oxide (MO), and methyl isobutyl ketone (MIBK) as typified in FIG. 1 and according to the formulas shown below.
  • DAA diacetone alcohol
  • MO mesityl oxide
  • MIBK methyl isobutyl ketone
  • Hydrogenation of acetone may be carried out in the presence of a heterogeneous catalyst.
  • Suitable hydrogenation catalysts include catalysts comprising one or more metals, optionally on a catalyst support.
  • the metals may be selected from Group IB, IIB, IIIB, IVB, VB, VIB, VIIB, VIII transition metals, a lanthanide metal, an actinide metal or a metal selected from any of Groups IIIA, IVA, VA, and VIA.
  • Catalysts that have exhibited high IPA selectivity may include Raney nickel, nickel-copper alloys, supported noble metals (such as (platinum, palladium, ruthenium, or rhodium), and copper chromite.
  • Suitable catalysts may include copper- or nickel-based catalysts.
  • suitable catalysts for the process of the present disclosure may be selected from catalysts comprising metal as an active component on an inert support.
  • acceptable carriers may comprise carbon, zeolite, aluminum oxide, silicon oxide, zirconium oxide and titanium oxide.
  • media silicon oxide may provide a high selectivity in respect to the hydrogenation of acetone to IPA.
  • the catalyst may comprise nickel mainly supported on a carrier, such as silica.
  • the metals of the catalysts may be dispersed throughout the support, layered throughout the support, coated on the outer surface of the support (for example, eggshell), or decorated on the surface of the support.
  • Suitable catalysts may comprise from 0.5 wt. % to 80 wt. % metal.
  • the hydrogenation of acetone by the present process may achieve favorable conversion of acetone and favorable selectivity and productivity to IPA.
  • conversion may refer to the fraction of acetone in the feed that is converted to a compound other than acetone. Conversion is expressed as a mole percentage based on acetone in the feed. The conversion may be at least at least 70%, at least 80%, at least 90%, at least 95%, or at least 99%.
  • catalysts that have high conversions are desirable, such as at least 90% or at least 95%, in some aspects, a lower conversion may be acceptable at high selectivity for IPA. It is, of course, well understood that in many cases, it is possible to compensate for conversion by appropriate recycle streams or use of larger reactors.
  • the disclosed reactor system and processes may provide that the hydrogenation process has a conversion rate of at least about 95%.
  • Selectivity is expressed as a mole percent based on converted acetone.
  • selectivities are provided on a carbon molar basis. It should be understood that each compound converted from acetone has an independent selectivity and that selectivity is independent from conversion. For example, if 90 mole % of the converted acetone is converted to IPA, the IPA selectivity is 90%. In some aspects, the selectivity to IPA is at least 90%, e.g., at least 95% or at least 98%.
  • Certain embodiments of the hydrogenation process may also have low selectivity to undesirable products, such as MO, MIBK, DAA. The selectivity to these undesirable products may be less than 4%, for example, less than 2% or less than 1%. In specific examples, these undesirable products are present in undetectable amounts.
  • the method according to the present disclosure may be carried out using a reactor in which liquidphase and gas-phase reactants flow in contact with a suitable catalyst, such as a trickle-bed reactor or wallflow reactor.
  • a suitable catalyst such as a trickle-bed reactor or wallflow reactor.
  • the catalyst may be present in the form of randomly packed particles (for example, pellets) of various shapes (for example, spheres, cylinders, hollow or multi-hole cylinders, saddles, or monoliths) or of a structured body, such as a monolith or structured packing.
  • Methods of contacting are appropriate so long as the reactant stream and catalyst are contacted under conditions suitable for hydrogenation and at a pressure and temperature sufficient to maintain the liquid phase.
  • the hydrogenation reactor is a trickle bed reactor or a single gas-liquid reactor.
  • the hydrogenation process may be carried out in a wide range of temperatures, pressures in the reactor and used velocities of liquid and gas along the surface. Depending on the type of catalyst, reaction conditions may be optimized in such a way as to obtain optimum hydrogenation (in terms of conversion and selectivity) of acetone.
  • the liquid phase hydrogenation may be performed at a temperature of 60 °C to 200 °C, or from 60 °C to 120 °C, or from 70 °C to 140 °C, and a pressure of about 5 to 40 bar (70 pounds per square inch (gauge, psi) to 590 psi, 500 kilopascals kPa to about 4000 kPa).
  • the product stream Depending on the temperature of the product stream, exiting the reactor or downstream vessel, the product stream must be cooled to a temperature of 60 to 100 °C at the point of entry of the subsequent reaction stage. Said cooling, if necessary, can be carried out by any means known to the person skilled in the art, such as by means of a heat exchanger.
  • an excess of hydrogen may be employed.
  • the molar ratio of hydrogen to acetone may range from 5: 1 to 1:1, from 3: 1 to 1: 1, or from 1.5: 1 to 1.05:1, or from 1.5: 1 to 1: 1.
  • the acetone may be present in the reactor feed in an amount from 5% to 20% by volume based on the total volume of the reactor.
  • a liquid stream comprising acetone may be directed co-currently with a hydrogen stream through the hydrogenation reactor.
  • a co-current flow of both streams may be maintained.
  • the process according to the present disclosure may be conducted continuously, but a batchwise process regime is also possible.
  • the reaction may proceed in discrete stages (campaigns) rather than a generally continuous mode.
  • a liquid reactor feed comprising acetone and a hydrogen feed may be directed to a single gas-liquid reactor comprising a solid catalyst to form a reactor effluent comprising IPA.
  • the acetone and hydrogen may be present in the liquid reactor feed such that the hydrogen is in excess and the acetone is present in an amount from 5% to 20% by volume.
  • the liquid reactor feed may have a water content of less than 1%, less than 0.5%, less than 0.1%, or less than 0.005%.
  • At least a portion of crude IPA produced during the hydrogenation process may be separated from the product stream and diverted to the hydrogenation reactor as a solvent for the acetone hydrogenation.
  • Generated crude IPA product may be processed in a separator to provide an effluent comprising IPA.
  • the resulting effluent comprising IPA may be used to further propagate the hydrogenation reaction of the hydrogenation reactor, or may be amassed in a storage tank of the reactor system configured to store crude IPA.
  • the storage tank may be configured to collect an amount of crude IPA that may then be subjected to one or more separation processes to provide a purified IPA product.
  • a gas-liquid separator may be used to separate the liquid fraction of the effluent comprising primarily IPA from the vapor fraction comprising primarily hydrogen.
  • the gas-liquid separator may comprise one or more of a high pressure gas-liquid separator and a low pressure gas-liquid separator. High pressure separation may proceed at a pressure close to that of the reactor, for example about 20 bar, while low pressure separation may proceed from 1 bar to about 6 bar.
  • the effluent may be cooled between the high-pressure and low-pressure gas-liquid separators.
  • the vapor fraction may comprise hydrogen and noncondensable gases (such as nitrogen or methane, which may be present as feed contaminants), and may also comprise vapors of the volatile liquid-phase components.
  • the effluent comprising IPA may be cooled for separation. That is, separation may proceed in a cold separator. Aspects of the present disclosure may incorporate both high pressure and low pressure cold separation. High pressure cooling may provide condensed isopropyl alcohol that may be transferred to the storage tank.
  • One or more recycle lines may be employed to further optimize the hydrogenation reactor system output.
  • at least a fraction of the liquid fraction from the gas-liquid separator may be directed as a recycle stream to the hydrogenation reactor.
  • at least about 80-95% of the crude IPA may be fed from the gas-liquid separator to the hydrogenation reactor as a liquid recycle stream.
  • Cmde IPA may be consolidated as an effluent stream from the gas-liquid separator and directed to the hydrogenation reactor as solvent for the acetone hydrogenation reaction.
  • recycled IPA may be adjusted. For example, as catalyst degrades over time a higher temperature of the reactor effluent may be required to maintain catalytic reactivity; accordingly, IPA recycle may be reduced to result in the temperature increase.
  • At least a portion of vapor fraction isolated from the gas-liquid separator may be directed to the hydrogenation reactor for the catalytic hydrogenation of acetone.
  • the hydrogen-rich vapor fraction from the low pressure separator may be directed to a fuel or flare system or recycled to the hydrogenation reactor.
  • the reaction process may include one or more compressors to aid in the recycle of the gas, and may additionally include means of cooling and gas-liquid separation to remove some of the organic vapors from the hydrogen-rich vapor fraction.
  • hydrogen may be recycled in the reactor system in a sufficient quantity to hydrogenate at least a portion of the acetone feedstream.
  • Isolated products from the one or more separation processes may be recycled to the intermediate storage tank.
  • generated light ends I and II may be recycled to the intermediate storage tank to facilitate the downstream processes.
  • at least a fraction of an unreacted acetone stream may be directed from the one or more separation processes to the storage tank.
  • At least a portion of generated crude IPA may be directed from the storage tank to the hydrogenation reactor.
  • the storage tank may comprise multiple storage tanks.
  • the storage tank may accrue contents until the one or more vessels reach a particular volume or capacity percentage in order to initiate downstream purification processes.
  • the storage tank may be at least 20 % full by volume for its contents to proceed to the separation.
  • the storage tank may be at least 30%, at least 40%, at least 50%, at least 60%, at least 70%, at least 80%, at least 85%, at least 90%, at least 95%, at least 98% full by volume for at least a portion of its stored content to proceed to subsequent downstream processing such as separation or recycle line processes.
  • a storage tank may be referred to as an “internal” storage tank where the tank is configured to be within the recycle loop for the reactor system. As such, the contents of the internal storage tank are not necessarily accrued for downstream purification and may be recycled instead.
  • a method of producing a purified IPA product may comprise reacting acetone and hydrogen in the presence of a solid catalyst in an adiabatic reactor to provide a reactor effluent comprising crude IPA and hydrogen.
  • the reactor effluent may be directed to a gas-liquid separator to provide a crude IPA.
  • At least a first portion of the crude IPA may be directed to the adiabatic reactor.
  • At least a portion of the crude IPA may be directed to a storage tank to provide an isolated crude IPA.
  • the isolated crude IPA may be directed from the storage tank (a) to the adiabatic reactor or (b) to one or more separation processes to yield a purified IP A.
  • one or more separation processes may be employed to split gaseous and liquid components generated during the hydrogenation process.
  • the isolation of gaseous components of the product mixture may also be performed according to a number of gas separation techniques commonly practiced by those skilled in the art.
  • the isolation of IPA may be achieved via flash separation, which is appropriate for gas-liquid separation.
  • the apparatuses used to accomplish this are well known in the art.
  • a product effluent comprising crude IPA may be subjected to one or more separation processes to provide purified IPA from light and heavy components.
  • the one or more separation processes may comprise directing at least a fraction of the stored crude IPA from the storage tank to a first separation column to yield at least a first light end and an IPA product.
  • the one or more separation processes may further comprise directing the IPA product to a second separation column to separate a heavy end, a second light end and to yield a purified IPA product.
  • a first column may remove lower-boiling byproducts and contaminants as a light end overhead stream.
  • the lower-boiling contaminants may include unconverted acetone as well as water, which is known to form an azeotrope with IPA.
  • the second separation column may remove higher- boiling byproducts and contaminants as a heavy -end bottoms stream, an additional amount of lower-boiling contaminants as an overhead stream, and a purified IPA product as a side stream.
  • the first or second separation columns may comprise a tray column or packed column.
  • the tray column may have from 5 to 70 trays, for example, from 15 to 50 trays or from 20 to 45 trays.
  • the second column may comprise a distillation column.
  • an extraction agent such as water, may be optionally added.
  • a method of converting an acetone feed stream to an IPA product may comprise combining the components in the presence of a suitable catalyst.
  • the method may also comprise separating a portion of products from the hydrogenation reactor for additional processing or recycle streams.
  • the method may further comprise storing a portion of generated IPA to provide a reservoir of IPA for recycle or further downstream processing or separation. Remaining reactive products and components generated throughout the processes may be recycled to different stages throughout the processes to facilitate efficient hydrogenation of acetone.
  • a system for the hydrogenation of acetone may comprise a hydrogenation reactor to effect at least a hydrogenation of an acetone feed stream in the presence of a catalyst to form a product mixture comprising at least crude IPA and hydrogen.
  • the system may further comprise a separator downstream from the hydrogenation reactor configured to effect a separation among components of the product mixture, wherein (a) crude IPA is separated from the product mixture, (b) hydrogen is separated from the product mixture, (c) or a combination thereof.
  • the system may further comprise a crude IPA vessel (an internal storage tank) downstream from the separator configured to control availability of crude IPA in system for recycle.
  • One or more separation columns may be configured downstream of the crude IPA vessel to effect at least a purification of the crude IPA.
  • the storage vessel may comprise one or more vessels and may also separately store other gases isolated in the reactor system.
  • additional product and byproduct storage vessels may store light ends recycled from the one or more separation processes.
  • the gas-liquid separator is configured to receive an effluent comprising IPA from the hydrogenation reactor.
  • the effluent may be cooled for high pressure and low pressure separation of IPA from hydrogen and other non-condensable gases in the effluent.
  • the gas-liquid separator which may be referred to as a flash drum, may be further configured to a chilled condenser to provide condensed IPA which may be recycled to the gas-liquid separator.
  • a chilled condenser may be used to return condensed organic gases to the reactor.
  • the disclosed storage tank may provide a discrete reservoir of crude IPA thereby assuring continuous processing and the appropriate hydrodynamics for downstream processing.
  • the storage tank may comprise one or more storage vessels configured to accommodate some volume of crude IPA.
  • the storage tank may be sized to accommodate, for example, the amount of crude IPA produced in a time span between 1 and 12 hours.
  • the intermediate storage tank may allow for flexible operation modes including full continuous operation mode to a staggered, or campaign-wise, mode.
  • the storage tank and the reservoir of crude IPA therein may optimize production and facilitate improved control over the full reactor system.
  • An inventory of cmde IPA may be accumulated that allows for minimal energy consumption.
  • the storage tank may include means of maintaining a temperature sufficiently low to suppress IPA vapor pressure, for example below 40 °C, below 30 °C, or below 25 °C.
  • the tank may include means of providing a non-flammable atmosphere in the head space, for example by providing a purge of nitrogen or other inert gas.
  • the storage tank may also support continuous operation.
  • a higher inventory of crude IPA may be accumulated at minimal energy consumption by maintaining an available volume in the reactor system.
  • Downstream processes may require high energy to maintain minimal flow in the two columns.
  • the storage tank may serve as a buffer to lessen the effects of acetone supply variability.
  • the intermediate storage tank may provide flexibility and efficient operation for the downstream by assuring a constant supply of crude IPA for recycle and downstream processing.
  • the intermediate storage tank is intended for storage of crude IPA in liquid form. Accordingly, in certain embodiments, the intermediate storage tank does not receive a gaseous effluent from the gas-liquid separator. In other words, the intermediate storage tank is not typically in fluid communication with a gaseous effluent from the gas-liquid separator.
  • portion may refer to a variable quantity ranging from none to all (i.e., 0% to 100%) with the specific quantity being dependent upon many factors, such as compositions, flows, operating parameters and the like as well as on factors external to the process such as desired products and byproducts, or availability of electrical power, fuel, or utilities.
  • acetone feed stream 1 may be combined with a crude IPA recycle stream 6 further defined herein to provide reagent stream 2.
  • the acetone feed stream 1 or reagent stream 2, as well as a hydrogen feed stream 13, may be conveyed to a hydrogenation reactor 200 for acetone hydrogenation in the presence of a heterogeneous catalyst.
  • hydrogenation reactor 200 may comprise a single device or multiple devices.
  • the reactant streams may be contacted with the catalyst(s) via any of the known reactor systems within the discretion of one skilled in the art, including for example trickle bed reactors, so long as the reactant stream and catalyst are contacted under conditions suitable for hydrogenation and at a pressure and temperature sufficient to maintain IPA in the liquid phase, with at least a portion of the acetone being hydrogenated, without departing from the scope of the disclosure.
  • the hydrogenation reactor may comprise a trickle bed reactor.
  • hydrogenation of acetone feed stream 1 may produce an effluent stream comprising crude IPA 3 which may proceed to a gas-liquid separator 202.
  • the gas-liquid separator 202 may isolate a crude IPA stream 5 from hydrogen and other products consolidated as a hydrogen and (non-condensable) gases stream 4.
  • the gas-liquid separator may comprise one or more of a high pressure or low pressure separator, one or more heat exchangers, as well as chilled condensers.
  • a portion of the hydrogen and gases stream 4 may be recycled to the hydrogenation reactor 200 to continue conversion of the acetone feed stream 1.
  • isolated crude IPA stream 5 may be split as a crude IPA recycle stream 6 and combined with acetone feed stream 1 for conversion in hydrogenation reactor 200.
  • At least a portion of crude IPA stream 5 may be directed to a storage tank 204.
  • the storage tank 204 may comprise one or more storage vessels configured to receive and collect an amount of crude IPA.
  • At least a portion of the crude IPA may be directed from the storage tank 204 as distillation feed stream 7 to separation processes in a first column 206.
  • First light ends stream 8 may be removed as a distillate.
  • the light ends stream 8 from the first column 206 comprises IPA, unreacted acetone, and water.
  • the bottoms stream 9 is introduced to the second column 208.
  • Second column 208 may be a tray column or packed column.
  • second column 208 is a tray column having from 5 to 70 trays, for example, from 15 to 50 trays or from 20 to 45 trays.
  • first column 206 and second column 208 may vary, when at atmospheric pressure, the temperature profiles of the first column 206, and second column 208 is typically varies from 60 °C to 90 °C. In certain aspects, both columns may operate at or near atmospheric pressure.
  • a final IPA product 11 may be separated as the side stream from a second light ends stream 10 and heavy ends stream 12.
  • a number of recycle streams may be incorporated to optimize operation of the disclosed hydrogenation reactor system.
  • one or more hydrogen recycle processes may be employed. From gas-liquid separator 202, at least a portion of a hydrogen and gases stream 4 may be combined with a pure hydrogen gas stream 13 for catalytic hydrogenation of acetone feed stream 1 in hydrogenation reactor 200. The unrecycled portion (stream 14) may be directed to a flare or fuel system. Furthermore, at least a portion of crude IPA stream 5 may be directed as a crude IPA recycle stream 6 and combined with acetone feed stream 1 for conversion in hydrogenation reactor 200, while the remainder of the crude IPA stream is diverted to the intermediate storage tank 204.
  • the gas-liquid separator may be configured to comprise or to be fluidly connected to one or more chilled condensers.
  • a hydrogen gas stream may be separated from the hydrogen and non-condensable gases obtained from the gas-liquid separator operating at high and low pressure.
  • IPA may be condensed from a stream in a chilled condenser and combined with the crude IPA.
  • gas-liquid separator 302 may isolate a crude IPA stream 5 from hydrogen and other products consolidated as a vapor fraction stream 4-1. At least a portion of the vapor fraction stream 4-1 may proceed to a condenser 305, which produces a hydrogen gas stream 4-II and an organic condensate stream 4-III, which is recycled to the gas-liquid separator.
  • the acetone feed stream 1 may be combined with a crude IPA recycle stream 9 to provide reagent stream 2.
  • the acetone feed stream 1 or reagent stream 2 may be conveyed to a hydrogenation reactor 400 for acetone hydrogenation in the presence of hydrogen gas 3 and a heterogeneous catalyst.
  • the hydrogenation of acetone feedstream 1 may provide an effluent stream comprising crude IPA 4 which may proceed to a high pressure gas-liquid separator 403.
  • High pressure gasliquid separator 403 may isolate hydrogen and other products consolidated as a hydrogen and (non- condensable) gases stream 5.
  • An effluent from the high pressure gas-liquid separator 503 may proceed to a low pressure cold separator/ chiller 407.
  • Hydrogen and gases stream 5 from the high pressure gas-liquid separator and hydrogen and gases stream 6 from the low pressure cold separator/chiller 407 may be directed to a condenser 405.
  • Condenser 407 allows venting of hydrogen and other non-condensable gases stream 8 while a stream of condensed IPA 7 may proceed to a crude IPA vessel 409.
  • Crude IPA vessel 409 is an internal storage tank. As an internal storage tank, its contents are not necessarily accrued for downstream purification.
  • a crude isopropyl recycle stream may be recycled to the hydrogenation reactor 400 to maintain conversion of the acetone feedstream 1.
  • at least a portion of isolated crude IPA stream 10 may be directed to an intermediate storage tank 404.
  • At least a portion of a crude IPA may be directed from the intermediate storage tank 404 as a stored stream 11 to separation processes in a first column 406.
  • the first light ends stream 12 may be removed or may be recycled to the intermediate storage tank 404.
  • a distillate stream 13 from the first column 506 is introduced to the second column 408.
  • a second light ends stream 14 may be removed or may be recycled to the intermediate storage tank 404.
  • a purified IPA stream 15 may be isolated from a second light ends stream 14 and heavies 16.
  • the disclosed systems and methods include at least the following aspects.
  • a method of producing a purified isopropyl alcohol product comprising: directing a liquid reactor feed comprising acetone and a hydrogen feed to a single gas-liquid reactor comprising a solid catalyst to form a reactor effluent comprising isopropyl alcohol, wherein the acetone is present in the liquid reactor feed in an amount from 5% to 15% by weight; directing the reactor effluent comprising isopropyl alcohol to a gas-liquid separator to separate a gaseous stream comprising hydrogen and a crude isopropyl alcohol stream; directing at least a fraction of the crude isopropyl alcohol stream to the single gas-liquid reactor; directing at least another fraction of the crude isopropyl alcohol stream to a storage tank to provide a stored crude isopropyl alcohol; and directing at least a fraction of the stored crude isopropyl alcohol from the storage tank to one or more separation processes to yield a purified isopropyl alcohol product, wherein the method is performed
  • Aspect 2 The method of aspect 1, wherein the storage tank comprises one or more storage vessels.
  • Aspect 3 The method of any one of aspects 1-2, wherein the gas-liquid separator comprises one or more of a high pressure gas-liquid separator and a low pressure gas-liquid separator.
  • Aspect 4 The method of any one of aspects 1-2, wherein the gas-liquid separator comprises one or more of a high pressure gas-liquid separator and a low pressure gas-liquid separator, and wherein the crude isopropyl alcohol stream proceeds from the one or more of the high pressure gas-liquid separator and the low pressure gas-liquid separator to the gas-liquid reactor or to the storage tank.
  • Aspect 5 The method of any one of aspects 1-4, wherein the hydrogenation process is carried out at a pressure of from 5 to 40 bar.
  • Aspect 6 The method of any one of aspects 1-5, wherein the hydrogenation is carried out at a temperature from 60 °C to 200 °C.
  • Aspect 7 The method of any one of aspects 1-5, wherein the hydrogenation proceeds at a temperature of from 60 °C to 120 °C.
  • Aspect 8 The method of any one of aspects 1-7, wherein the single gas-liquid reactor has an inlet and outlet temperature differential of 15 °C to 40 °C.
  • Aspect 9 The method of any one of aspects 1-8, wherein a molar ratio of hydrogen and acetone is maintained at 1:1 to 1.5: 1.
  • Aspect 10 The method of any one of aspects 1-9, wherein the solid catalyst comprises a heterogeneous catalyst.
  • Aspect 11 The method of any one of aspects 1-10, wherein the solid catalyst comprises copper or nickel.
  • Aspect 12 The method of any of aspects 1-8, wherein the hydrogenation process has an acetone conversion of at least 95 %.
  • Aspect 13 The method of any of aspects 1-9, wherein directing at least a fraction of the crude isopropyl alcohol stream to the single gas-liquid reactor from the gas-liquid separator comprises directing at least about 80-95% of the crude isopropyl alcohol to the single gas-liquid reactor.
  • Aspect 14 The method of any one of aspects 1-13, wherein the liquid reactor feed has a water content of less than 0.5 %.
  • Aspect 15 The method of any one of aspects 1-14, wherein the one or more separation processes comprises directing at least a fraction of the stored crude isopropyl alcohol from the storage tank to a first separation column to yield at least a first light end and an intermediate isopropyl alcohol product, and directing the intermediate isopropyl alcohol to a second separation column to yield a second light end and a purified isopropyl alcohol product.
  • Aspect 16 The method of any one of aspects 1-15, further comprising directing a hydrogen gas stream from the gas-liquid separator to the single gas-liquid reactor.
  • Aspect 17 The method of any one of aspects 1-15, further comprising (a) separating a hydrogen gas stream from the gas-liquid separator in a chilled condenser for recycling, or (b) condensing a crude isopropyl alcohol stream in a chilled condenser for recycling to the storage tank.
  • a method of producing a purified isopropyl alcohol product comprising: reacting acetone and hydrogen in the presence of a solid catalyst in an adiabatic reactor to provide a reactor effluent comprising crude isopropyl alcohol and hydrogen; directing the reactor effluent to a gas-liquid separator to provide a crude isopropyl alcohol; and directing at least a first portion of the crude isopropyl alcohol to the adiabatic reactor; directing at least a portion of the crude isopropyl alcohol to a storage tank to provide an isolated crude isopropyl alcohol, wherein the isolated crude isopropyl alcohol is directed from the storage tank (a) to the adiabatic reactor or (b) to one or more separation processes to yield a purified isopropyl alcohol product.
  • Aspect 19 The method of aspect 18, wherein at least a portion of the hydrogen is directed to the adiabatic reactor.
  • Aspect 20 The method of aspect 18, wherein a molar ratio of hydrogen to acetone in the reactor system is less than 0.1%.
  • Ranges can be expressed herein as from “about” one particular value, and/or to “about” another particular value. When such a range is expressed, another aspect includes from the one particular value and/or to the other particular value. Similarly, when values are expressed as approximations, by use of the antecedent ‘about,’ it will be understood that the particular value forms another aspect. It will be further understood that the endpoints of each of the ranges are significant both in relation to the other endpoint, and independently of the other endpoint. It is also understood that there are a number of values disclosed herein, and that each value is also herein disclosed as “about” that particular value in addition to the value itself. For example, if the value “10” is disclosed, then “about 10” is also disclosed. It is also understood that each unit between two particular units are also disclosed. For example, if 10 and 15 are disclosed, then 11, 12, 13, and 14 are also disclosed.
  • the terms “optional” or “optionally” means that the subsequently described event or circumstance can or cannot occur, and that the description includes instances where said event or circumstance occurs and instances where it does not.
  • the phrase “optionally substituted alkyl” means that the alkyl group can or cannot be substituted and that the description includes both substituted and un-substituted alkyl groups.
  • compositions disclosed herein have certain functions. Disclosed herein are certain structural requirements for performing the disclosed functions, and it is understood that there are a variety of structures that can perform the same function that are related to the disclosed structures, and that these structures will typically achieve the same result.
  • Cooled reactor effluent was transferred to a high pressure (HP) gas-liquid separator operating at a pressure of 15-30 bar and 35 °C to 55 °C.
  • HP high pressure
  • Some of the hydrogen rich vapors were flashed in a HP Cold Separator.
  • pressure control valve in the vapor outlet line were opened and the gases will pass to the fuel system or flared off.
  • Pressure in the HP cold separator liquid outlet line was reduced from to 1 bar in the level control valve.
  • the fluid was flashed in a low pressure (LP) cold separator/chiller (heat exchanger).
  • LP cold separator/chiller has tube bundle with continuous recirculation of chilled water in the vapor space.
  • Vapors separated in the LP cold separator were cooled in this cooler to about 25 to 35 °C. This condensed any IPA carry over in the vapor and enhance recovery.
  • the separated liquid in the LP cold separator was routed to crude IPA vessel under level control.
  • Vent gas from the LP cold separator/chiller was further cooled to about 10 °C in shell side of vent gas chiller using chilled water in the tube side. This cooling condensed any associated IPA content in the vapor.
  • Hydrogen rich vapors from vent gas chiller were routed either to fuel system or to the flared system or to the process side.

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

Abstract

L'invention concerne un procédé de production d'un produit d'alcool isopropylique purifié qui peut comprendre : l'acheminement d'une charge d'alimentation de réacteur liquide d'acétone et une charge d'alimentation d'hydrogène vers un réacteur gaz-liquide unique comprenant un catalyseur solide pour former un effluent de réacteur comprenant de l'alcool isopropylique ; l'acheminement de l'effluent de réacteur vers un séparateur gaz-liquide pour séparer un flux gazeux comprenant de l'hydrogène et un flux d'alcool isopropylique brut ; l'acheminement d'au moins une fraction du flux d'alcool isopropylique brut vers le réacteur gaz-liquide unique ; l'acheminement d'au moins une autre fraction du flux d'alcool isopropylique brut vers un réservoir de stockage pour obtenir un alcool isopropylique brut stocké ; et l'acheminement d'au moins une fraction de l'alcool isopropylique brut stocké du réservoir de stockage vers un ou plusieurs procédés de séparation pour produire un produit d'alcool isopropylique purifié.
PCT/IB2023/060820 2022-10-28 2023-10-26 Configuration de procédé pour la production d'alcool isopropylique WO2024089647A1 (fr)

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