US20200325093A1 - Acrylic acid, and methods of producing thereof - Google Patents

Acrylic acid, and methods of producing thereof Download PDF

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US20200325093A1
US20200325093A1 US16/087,051 US201716087051A US2020325093A1 US 20200325093 A1 US20200325093 A1 US 20200325093A1 US 201716087051 A US201716087051 A US 201716087051A US 2020325093 A1 US2020325093 A1 US 2020325093A1
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acrylic acid
propiolactone
beta
zeolite
produced
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Sadesh H. Sookraj
Alexander Tseitlin
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Novomer Inc
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Novomer Inc
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Publication of US20200325093A1 publication Critical patent/US20200325093A1/en
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
    • B01J20/26—Synthetic macromolecular compounds
    • B01J20/265—Synthetic macromolecular compounds modified or post-treated polymers
    • B01J20/267—Cross-linked polymers
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/30—Processes for preparing, regenerating, or reactivating
    • B01J20/3085—Chemical treatments not covered by groups B01J20/3007 - B01J20/3078
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • B01J27/14—Phosphorus; Compounds thereof
    • B01J27/16—Phosphorus; Compounds thereof containing oxygen, i.e. acids, anhydrides and their derivates with N, S, B or halogens without carriers or on carriers based on C, Si, Al or Zr; also salts of Si, Al and Zr
    • B01J27/18—Phosphorus; Compounds thereof containing oxygen, i.e. acids, anhydrides and their derivates with N, S, B or halogens without carriers or on carriers based on C, Si, Al or Zr; also salts of Si, Al and Zr with metals other than Al or Zr
    • B01J27/1802—Salts or mixtures of anhydrides with compounds of other metals than V, Nb, Ta, Cr, Mo, W, Mn, Tc, Re, e.g. phosphates, thiophosphates
    • B01J27/1806—Salts or mixtures of anhydrides with compounds of other metals than V, Nb, Ta, Cr, Mo, W, Mn, Tc, Re, e.g. phosphates, thiophosphates with alkaline or alkaline earth metals
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J29/00—Catalysts comprising molecular sieves
    • B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
    • B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
    • B01J29/08—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the faujasite type, e.g. type X or Y
    • B01J29/084—Y-type faujasite
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J29/00—Catalysts comprising molecular sieves
    • B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
    • B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
    • B01J29/40—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the pentasil type, e.g. types ZSM-5, ZSM-8 or ZSM-11, as exemplified by patent documents US3702886, GB1334243 and US3709979, respectively
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J4/00—Feed or outlet devices; Feed or outlet control devices
    • B01J4/001—Feed or outlet devices as such, e.g. feeding tubes
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J8/00—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes
    • B01J8/02—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes with stationary particles, e.g. in fixed beds
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J8/00—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes
    • B01J8/02—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes with stationary particles, e.g. in fixed beds
    • B01J8/0278—Feeding reactive fluids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/42—Separation; Purification; Stabilisation; Use of additives
    • C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
    • C07C51/44—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation by distillation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/42—Separation; Purification; Stabilisation; Use of additives
    • C07C51/50—Use of additives, e.g. for stabilisation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
    • C07C57/03—Monocarboxylic acids
    • C07C57/04—Acrylic acid; Methacrylic acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D305/00—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms
    • C07D305/02—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D305/10—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings having one or more double bonds between ring members or between ring members and non-ring members
    • C07D305/12—Beta-lactones
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F120/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
    • C08F120/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F120/04—Acids; Metal salts or ammonium salts thereof
    • C08F120/06—Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
    • C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
    • C08F20/04—Acids, Metal salts or ammonium salts thereof
    • C08F20/06—Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2208/00—Processes carried out in the presence of solid particles; Reactors therefor
    • B01J2208/00008—Controlling the process
    • B01J2208/00017—Controlling the temperature
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2208/00—Processes carried out in the presence of solid particles; Reactors therefor
    • B01J2208/00008—Controlling the process
    • B01J2208/00539—Pressure
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2208/00—Processes carried out in the presence of solid particles; Reactors therefor
    • B01J2208/00743—Feeding or discharging of solids
    • B01J2208/00752—Feeding

Definitions

  • the present disclosure relates generally to production of acrylic acid, and more specifically to production of acrylic acid from beta-propiolactone.
  • SAPs acrylic acid-based superabsorbent polymers
  • acrylic acid is typically derived from propylene oxidation.
  • Propylene is primarily a product of oil refining and its price and availability are closely tied to crude oil prices. Because of this, acrylic acid prices have risen dramatically in recent years. Thus, there exists a need in the art for alternative methods to synthesize acrylic acid.
  • a method of producing acrylic acid from beta-propiolactone by combining beta-propiolactone, a heterogeneous catalyst, a polymerization inhibitor, and optionally a solvent; and producing acrylic acid from at least a portion of the beta-propiolactone.
  • the heterogeneous catalyst is a zeolite.
  • the zeolite is an acidic zeolite.
  • FIG. 1 depicts an exemplary process to produce acrylic acid from beta-propiolactone in the presence of a zeolite and a polymerization inhibitor.
  • FIG. 2 depicts an exemplary reaction system to produce acrylic acid from beta-propiolactone according to the methods described herein.
  • Such methods produce acrylic acid from beta-propiolactone in a one-pot reaction. Such methods may also produce acrylic acid in high yields, by minimizing other products that may form, such as polypropiolactone and polyacrylic acid.
  • process 100 is an exemplary process to produce acrylic acid.
  • Beta-propiolactone 102 is combined with zeolite 104 and polymerization inhibitor 106 to produce acrylic acid 110 .
  • process 100 is performed neat.
  • process 100 is performed in the presence of a solvent.
  • the method further includes continuously isolating the acrylic acid produced.
  • the acrylic acid is isolated by distillation.
  • beta-propiolactone The beta-propiolactone, catalysts, polymerization inhibitors, solvents and reaction conditions, as well as acrylic acid produced, are described in further detail below.
  • the beta-propiolactone used in the methods described herein may be produced by epoxide carbonylation.
  • the beta-propiolactone may be produced from ethylene oxide and carbon monoxide via a carbonylation reaction. See e.g., WO 2010/118128.
  • the beta-propiolactone is produced by reacting ethylene oxide with carbon monoxide in the presence of a carbonylation catalyst and optionally a solvent.
  • the carbonylation catalyst comprises [(TPP)Al][Co(CO) 4 ], [(ClTPP)Al][Co(CO) 4 ], [(TPP)Cr][Co(CO) 4 ], [(ClTPP)Cr][Co(CO) 4 ], [(salcy)Cr][Co(CO) 4 ], [(salph)Cr][Co(CO) 4 ], or [(salph)Al][Co(CO) 4 ].
  • TPP refers to tetraphenylporphyrin
  • ClTPP refers to meso-tetra(4-chlorophenyl)porphyrin
  • sicy refers to (N,N′-bis(3,5-di-tert-butylsalicylidene)-1,2-diaminocyclohexane)
  • siph refers to (N,N′-bis(salicylidene)-o-phenylenediamine).
  • the beta-propiolactone is added to the reaction with an initial pressure of carbon monoxide. In other variations where the method is continuous, no initial pressure is required to add the beta-propiolactone.
  • the catalyst used in the conversion of beta-propiolactone to acrylic acid is a heterogeneous catalyst.
  • the catalyst is a zeolite.
  • the catalyst is an acidic zeolite.
  • the zeolite may be Zeolite Y or Zeolite ZSM-5.
  • the zeolite is Zeolite Y hydrogen in powder form.
  • the Zeolite Y hydrogen has a 80:1 mole ratio SiO 2 /Al 2 O 3 , and has a powder surface area of 780 m 2 /g.
  • the zeolite may be dried using any suitable methods or techniques known in the art (e.g., using heat and/or vacuum) prior to use.
  • a combination of any of the catalysts described herein may also be used.
  • the polymerization inhibitor used in the conversion of beta-propiolactone to acrylic acid is a radical polymerization inhibitor.
  • Suitable polymerization inhibitors may include, for example, phenothiazine.
  • the conversion of beta-propiolactone to acrylic acid is performed neat. In other embodiments, the conversion of beta-propiolactone to acrylic acid is performed in the presence of a solvent.
  • the solvent selected (i) dissolves, or at least partially dissolves, the beta-propiolactone, but does not react, or minimally reacts, with the beta-propiolactone; or (ii) has a high boiling point so that the acrylic acid produced may be distilled while solvent remains in the reactor, or a combination of (i) and (ii).
  • the solvent is a polar aprotic solvent.
  • the solvent may be a high boiling polar aprotic solvent.
  • the solvent includes sulfolane.
  • the amount of solvent used may be varied to balance the metering of beta-propiolactone added and the overall concentration of reagents in the reaction mixture.
  • the ratio of beta-propiolactone to solvent in the reaction is about 1:1.
  • the solvent may be dried using any suitable methods or techniques known in the art prior to use.
  • the methods described herein may be carried out batch-wise or continuously. Various factors may affect the conversion of beta-propiolactone to acrylic acid according to the methods described herein.
  • the rate of beta-propiolactone addition may affect the yield of acrylic acid.
  • the method further includes controlling the rate of addition of beta-propiolactone. A slower rate of beta-propiolactone addition was unexpectedly observed to increase the yield of acrylic acid produced.
  • the beta-propiolactone is provided at a rate of less than 1.5 g/min, less than 1.4 g/min, less than 1.3 g/min, less than 1.2 g/ min, less than 1.1 g/min, less than 1 g/min, less than 0.9 g/min, or less than 0.8 g/ min; or between 0.5 g/min and 1.5 g/min, or between 0.75 g/min and 1.25 g/min; or about 1 g/min.
  • the method further includes minimizing or suppressing production of polypropiolactone from at least a portion of the beta-propiolactone. In one variation, little or no polypropiolactone is produced. In other variations that may be combined with the foregoing, the method further includes minimizing or supressing production of polyacrylic acid from at least a portion of the acrylic acid produced. In one variation, little or no polyacrylic acid is produced.
  • beta-propiolactone added may be metered by any suitable methods or techniques in the art.
  • beta-propiolactone may be metered or slowly added to the reactor via a needle valve.
  • the removal of acrylic acid produced may also affect the yield of acrylic acid. Stripping off of the acrylic acid produced was also unexpectedly observed to increase - yield of the acrylic acid produced.
  • the method further includes stripping off at least a portion of the acrylic acid produced (e.g., by distillation). In certain variations of the foregoing, stripping off at least a portion of the acrylic acid produced minimizes polymerization of the acrylic acid, and thus, formation of polyacrylic acid.
  • the acrylic acid may be produced at a pressure that strips off of at least a portion of the acrylic acid produced.
  • the method may be performed at subatmospheric pressure of 100 mm Hg. In other variations, vacuum may be applied in the range of 200 to 20 mm Hg.
  • the acrylic acid may be produced at elevated temperatures according to the methods described herein.
  • the temperature is at least 100° C., at least 105° C., at least 110° C., at least 115° C., at least 120° C., at least 125° C., at least 130° C., at least 135° C., at least 140° C., at least 145° C., at least 150° C., at least 155° C., at least 160° C., at least 165° C., at least 170° C., at least 175° C., at least 180° C., at least 185° C., at least 190° C., at least 195° C., at least 200° C., at least 205° C., at least 210° C., at least 215° C., or at least 220° C.; or between 100° C.
  • the reactor in which the method is performed is heated to the temperatures described herein.
  • the beta-propiolactone, polymerization inhibitor, catalyst, and/or solvent is provided to the reactor at the temperatures described herein.
  • acrylic acid is produced at a yield of at least 50%, at least 55%, at least 60%, at least 65%, at least 70%, at least 75%, at least 80%, at least 85%, at least 90%, or at least 95%.
  • the acrylic acid produced has a purity of at least 95%, at least 96%, at least 97%, or at least 98%.
  • the acrylic acid produced is isolated, e.g., by distillation, the acrylic acid has a purity of at least 98%, at least 98.5%, at least 99%, at least 99.1%, at least 99.2%, at least 99.3%, at least 99.4%, at least 99.5%, at least 99.6%, at least 99.7%, at least 99.8%, or at least 99.9%.
  • acrylic acid produced according to the methods described herein may be used for various applications.
  • acrylic acid may be used to make polyacrylic acid for superabsorbent polymers (SAPs).
  • SAPs superabsorbent polymers
  • the SAPs find use in diapers, adult incontinence products, and feminine hygiene products among other things.
  • a method for producing a superabsorbent polymer by: polymerizing the acrylic acid produced according to any of the methods described herein in the presence of a cross-linker to produce the superabsorbent polymer.
  • System 200 is configured to produce acrylic acid from beta-propiolactone, according to the methods described herein.
  • System 200 includes reactor 210 , configured to receive beta-propiolactone, a zeolite, and a polymerization inhibitor, and to produce acrylic acid from at least a portion of the beta-propiolactone according to the methods described herein.
  • Reactor 210 is configured to produce acrylic acid at an elevated temperature. Any of the temperatures described herein for the methods may be employed in the system.
  • reactor 210 is configured to produce acrylic acid at a temperature between 170° C. and 200° C. Suitable reactors may include, for example, a Parr reactor.
  • reactor 210 is configured to control the rate of addition of one or more of the beta-propiolactone, the zeolite, and the polymerization inhibitor added.
  • a mixture of the beta-propiolactone and the polymerization inhibitor may be slowly added using a needle valve to a mixture of catalyst in a solvent.
  • reactor 210 further includes vapor port 214 .
  • reactor 210 is configured to continuously strip off at least a portion of the acrylic acid produced, and vapor port 214 is configured to pass acrylic acid vapors to collection vessel 220 .
  • system 200 further includes acid/base scrubber 230 , configured to receive acrylic acid from collection vessel 220 .
  • acid/base scrubber 230 may be omitted.
  • elements 212 , 216 and 222 are dip tubes.
  • the systems provided herein may be configured for batch-wise or continuous production of acrylic acid.
  • This Example demonstrates the production of acrylic acid from beta-propiolactone using a zeolite.
  • a mixture of beta-propiolactone (3.0 g) and phenothiazine (9.0 mg) was added using a needle value to a mixture of sulfolane (40.0g) and Zeolite Y hydrogen (20.0 g) at 165° C. with 50 psi of carbon monoxide.
  • Zeolite Y hydrogen (80:1 mole ratio SiO 2 /Al 2 O 3 , powder S.A. 780 m 2 /g) was dried under vacuum at 100° C. for one day before use.
  • Phenothiazine was the polymerization inhibitor used.
  • Sulfolane was the solvent used, and was dried over 3 ⁇ molecular sieves prior to use.
  • the beta-propiolactone was added slowly using the needle valve over about 8.6 minutes. The reaction mixture was heated to 170° C. to produce acrylic acid.
  • the reaction was monitored by infrared spectroscopy (IR). The reaction was observed to be completed after about 3 hours, when no beta-propiolactone was detectable by IR.
  • the zeolite was then filtered off from the reaction mixture, and a sample of the resulting mixture was dissolved in deuterium (D 2 O) and chloroform (CDCl 3 ) for nuclear magnetic resonance (NMR) analysis. The observed vinyl peaks between ⁇ 5.80 and 6.47 ppm in the 1 H NMR confirmed the production of acrylic acid.

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