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

Acrylic acid, and methods of producing thereof Download PDF

Info

Publication number
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
Authority
US
United States
Prior art keywords
acrylic acid
propiolactone
beta
zeolite
produced
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Abandoned
Application number
US16/087,051
Other languages
English (en)
Inventor
Sadesh H. Sookraj
Alexander Tseitlin
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Novomer Inc
Original Assignee
Novomer Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Novomer Inc filed Critical Novomer Inc
Priority to US16/087,051 priority Critical patent/US20200325093A1/en
Assigned to NOVOMER, INC. reassignment NOVOMER, INC. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: SOOKRAJ, Sadesh H., TSEITLIN, ALEXANDER
Publication of US20200325093A1 publication Critical patent/US20200325093A1/en
Abandoned legal-status Critical Current

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/09—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.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Materials Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Analytical Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Catalysts (AREA)
  • Polyesters Or Polycarbonates (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
US16/087,051 2016-03-21 2017-03-21 Acrylic acid, and methods of producing thereof Abandoned US20200325093A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US16/087,051 US20200325093A1 (en) 2016-03-21 2017-03-21 Acrylic acid, and methods of producing thereof

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201662311262P 2016-03-21 2016-03-21
PCT/US2017/023302 WO2017165344A1 (en) 2016-03-21 2017-03-21 Acrylic acid, and methods of producing thereof
US16/087,051 US20200325093A1 (en) 2016-03-21 2017-03-21 Acrylic acid, and methods of producing thereof

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2017/023302 A-371-Of-International WO2017165344A1 (en) 2016-03-21 2017-03-21 Acrylic acid, and methods of producing thereof

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US17/152,248 Continuation US11827590B2 (en) 2016-03-21 2021-01-19 Acrylic acid, and methods of producing thereof

Publications (1)

Publication Number Publication Date
US20200325093A1 true US20200325093A1 (en) 2020-10-15

Family

ID=59855298

Family Applications (3)

Application Number Title Priority Date Filing Date
US16/087,051 Abandoned US20200325093A1 (en) 2016-03-21 2017-03-21 Acrylic acid, and methods of producing thereof
US15/464,346 Active 2037-11-20 US10662139B2 (en) 2016-03-21 2017-03-21 Acrylic acid production process
US17/152,248 Active 2037-10-02 US11827590B2 (en) 2016-03-21 2021-01-19 Acrylic acid, and methods of producing thereof

Family Applications After (2)

Application Number Title Priority Date Filing Date
US15/464,346 Active 2037-11-20 US10662139B2 (en) 2016-03-21 2017-03-21 Acrylic acid production process
US17/152,248 Active 2037-10-02 US11827590B2 (en) 2016-03-21 2021-01-19 Acrylic acid, and methods of producing thereof

Country Status (14)

Country Link
US (3) US20200325093A1 (zh)
EP (2) EP3433226B1 (zh)
JP (2) JP2019509307A (zh)
KR (2) KR20180118797A (zh)
CN (3) CN109153628B (zh)
AU (2) AU2017238018A1 (zh)
BR (2) BR112018069019A2 (zh)
CA (2) CA3018208A1 (zh)
CO (1) CO2018010877A2 (zh)
MX (2) MX2018011485A (zh)
SA (2) SA518400053B1 (zh)
TW (1) TW201802061A (zh)
WO (2) WO2017165323A1 (zh)
ZA (1) ZA201807001B (zh)

Families Citing this family (29)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012158573A1 (en) 2011-05-13 2012-11-22 Novomer, Inc. Catalytic carbonylation catalysts and methods
JP2017506286A (ja) 2013-12-07 2017-03-02 ノボマー， インコーポレイテッド ナノろ過膜および使用の方法
US10858329B2 (en) 2014-05-05 2020-12-08 Novomer, Inc. Catalyst recycle methods
SG11201610058QA (en) 2014-05-30 2016-12-29 Novomer Inc Integrated methods for chemical synthesis
WO2016015019A1 (en) 2014-07-25 2016-01-28 Novomer, Inc. Synthesis of metal complexes and uses thereof
MA41513A (fr) 2015-02-13 2017-12-19 Novomer Inc Procédé de distillation pour la production d'acide acrylique
MA41510A (fr) 2015-02-13 2017-12-19 Novomer Inc Procédé de production d'acide acrylique
MX2017010408A (es) 2015-02-13 2018-02-23 Novomer Inc Procesos continuos de carbonilacion.
MA41514A (fr) 2015-02-13 2017-12-19 Novomer Inc Procédés intégrés de synthèse chimique
MA41507A (fr) 2015-02-13 2017-12-19 Novomer Inc Systèmes et procédés de production de polymères
MA41508A (fr) 2015-02-13 2017-12-19 Novomer Inc Systèmes et procédés de production d'acide polyacrylique
CN111944130B (zh) 2015-02-13 2022-10-25 诺沃梅尔公司 聚丙内酯生产方法和系统
WO2016130988A1 (en) 2015-02-13 2016-08-18 Novomer, Inc. Flexible chemical production platform
JP7029804B2 (ja) 2015-07-31 2022-03-04 ノボマー， インコーポレイテッド アクリル酸およびその前駆体のための生成系／生成プロセス
CA3018208A1 (en) 2016-03-21 2017-09-28 Novomer, Inc. Improved acrylic acid production process
WO2017165345A1 (en) 2016-03-21 2017-09-28 Novomer, Inc. Systems and methods for producing superabsorbent polymers
MA46720A (fr) 2016-11-02 2019-09-11 Novomer Inc Polymères absorbants, procédés et systèmes de production et utilisations correspondantes
US10144802B2 (en) 2016-12-05 2018-12-04 Novomer, Inc. Beta-propiolactone based copolymers containing biogenic carbon, methods for their production and uses thereof
US10500104B2 (en) 2016-12-06 2019-12-10 Novomer, Inc. Biodegradable sanitary articles with higher biobased content
US10940059B2 (en) * 2016-12-19 2021-03-09 The Procter & Gamble Company Article with zeolites
US10065914B1 (en) 2017-04-24 2018-09-04 Novomer, Inc. Thermolysis of polypropiolactone to produce acrylic acid
US10676426B2 (en) 2017-06-30 2020-06-09 Novomer, Inc. Acrylonitrile derivatives from epoxide and carbon monoxide reagents
US10590099B1 (en) 2017-08-10 2020-03-17 Novomer, Inc. Processes for producing beta-lactone with heterogenous catalysts
WO2019070981A1 (en) 2017-10-05 2019-04-11 Novomer, Inc. ISOCYANATES, DERIVATIVES, AND THEIR PRODUCTION PROCESSES
JP2021528478A (ja) * 2018-06-29 2021-10-21 ノボマー， インコーポレイテッド ベータ−ラクトンから有機酸を直接に生成するためのシステム及びプロセス
CN112423962A (zh) 2018-07-13 2021-02-26 诺沃梅尔公司 聚内酯发泡体及其制造方法
CN113614064A (zh) 2019-03-08 2021-11-05 诺沃梅尔公司 用于产生酰胺和腈化合物的集成方法和系统
FR3110570B1 (fr) 2020-05-19 2022-05-20 Commissariat Energie Atomique PROCEDE DE PREPARATION D’ACIDE ACRYLIQUE A PARTIR DE β-PROPIOLACTONE
WO2024063412A1 (ko) * 2022-09-19 2024-03-28 주식회사 엘지화학 불포화 카르복실산 및 그 유도체 제조용 촉매

Family Cites Families (79)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3037346A (en) * 1958-05-29 1962-06-05 Scient Design Co Heat storage in chemical processes
US3176042A (en) * 1959-10-20 1965-03-30 Celanese Corp Treating propiolactone with heated phosphoric acid to produce acrylic acid
US3462484A (en) * 1959-10-20 1969-08-19 Celanese Corp Condensation of acrylic acid
US3849457A (en) 1969-01-27 1974-11-19 Mobil Oil Corp Preparation of carboxylic acids by hydrogenolysis of esters
US3647680A (en) 1969-09-25 1972-03-07 Universal Oil Prod Co Continuous reforming-regeneration process
US3689533A (en) 1971-03-15 1972-09-05 Monsanto Co Production of carboxylic acids and esters
BE786398A (fr) * 1971-07-21 1973-01-18 Basf Ag Procede de preparation de l'acide acrylique anhydre
US3885155A (en) 1973-11-01 1975-05-20 Stanford Research Inst Mass spectrometric determination of carbon 14
US4427884A (en) 1982-01-25 1984-01-24 The Research Foundation Of State University Of New York Method for detecting and quantifying carbon isotopes
JPS601205A (ja) * 1983-06-20 1985-01-07 Kao Corp 高吸水性ポリマ−の製造法
JPS61213206A (ja) * 1985-03-20 1986-09-22 Mitsubishi Petrochem Co Ltd 高吸水性ポリマ−の製造方法
DK160599C (da) * 1986-06-04 1991-09-02 Jydsk Varmekedelfab As Fremgangsmaade og apparat til rensning af roeggas samt genvinding af varme herfra
US5198578A (en) 1986-07-17 1993-03-30 Union Carbide Chemicals Anhydrous diluents for the propylene oxidation reaction to acrolein and acrolein oxidation to acrylic acid
US4973841A (en) 1990-02-02 1990-11-27 Genus, Inc. Precision ultra-sensitive trace detector for carbon-14 when it is at concentration close to that present in recent organic materials
DE4123912A1 (de) * 1991-07-18 1993-01-21 Klaus Oesterle Fuer tensid- bzw. salzhaltiges wasser geeignete vorrichtung zur trennung von wasser und oel
SG45321A1 (en) 1992-10-02 1998-01-16 Rhone Poulenc Chimie Process for isomerization of lactones to pentenoic acids by acidic or basic catalysts
US5438194A (en) 1993-07-30 1995-08-01 High Voltage Engineering Europa B.V. Ultra-sensitive molecular identifier
US5661299A (en) 1996-06-25 1997-08-26 High Voltage Engineering Europa B.V. Miniature AMS detector for ultrasensitive detection of individual carbon-14 and tritium atoms
JP2003173088A (ja) 2001-12-07 2003-06-20 Pfu Ltd トナーリサイクルシステムのトナー濃度調整方式
EP1732874A1 (en) * 2004-04-02 2006-12-20 Ciba Speciality Chemicals Water Treatments Limited Preparation of acrylic acid derivatives from alpha or beta-hydroxy carboxylic acids
DE102005039156B4 (de) * 2005-08-17 2014-12-24 Evonik Degussa Gmbh Verfahren zur Herstellung von (Meth)Acrylsäure mit Schwersiedeaufarbeitung durch Kristallisation
US7902416B2 (en) * 2006-12-28 2011-03-08 Uop Llc Fluidized bed reactor with back-mixing for dehydrogenation of light paraffins
WO2009155086A2 (en) 2008-05-30 2009-12-23 E. I. Du Pont De Nemours And Company Renewably resourced chemicals and intermediates
JP5339845B2 (ja) 2008-10-14 2013-11-13 Ｊｘ日鉱日石エネルギー株式会社 流動接触分解方法
CA2757835A1 (en) 2009-04-08 2010-10-14 Novomer, Inc. Process for beta-lactone production
EP2533753B1 (en) 2009-11-10 2022-07-06 Laboratory Skin Care, Inc. Sunscreen compositions comprising uniform, rigid, spherical, nanoporous calcium phosphate particles, and methods of making and using the same
WO2011100608A1 (en) 2010-02-11 2011-08-18 Metabolix, Inc. Process for producing a monomer component from a genetically modified polyhydroxyalkanoate biomass
SG188323A1 (en) 2010-08-28 2013-04-30 Novomer Inc Succinic anhydride from ethylene oxide
DE102010040757A1 (de) 2010-09-14 2012-03-15 Man Diesel & Turbo Se Rohrbündelreaktor
ES2746204T3 (es) 2010-10-11 2020-03-05 Novomer Inc Mezclas de polímeros
FR2966161B1 (fr) 2010-10-15 2013-12-20 Total Raffinage Marketing Procede de reaction et de stripage etage dans une unite de fcc pour maximisation de la production d'olefines
MY175358A (en) * 2010-11-11 2020-06-22 Lucite Int Uk Ltd A process for the production of ethylenically unsaturated carboxylic acids or esters and a catalyst therefor
SG193629A1 (en) * 2011-03-28 2013-11-29 Agency Science Tech & Res Synthesis of diacids
WO2012158573A1 (en) 2011-05-13 2012-11-22 Novomer, Inc. Catalytic carbonylation catalysts and methods
US20110319849A1 (en) * 2011-07-01 2011-12-29 Dimitris Ioannis Collias Absorbent article comprising a synthetic polymer derived from a renewable resource and methods of producing said article
HUE039449T2 (hu) * 2011-10-26 2018-12-28 Novomer Inc Eljárás akrilátok elõállítására epoxidokból
JP2015511947A (ja) 2012-02-13 2015-04-23 ノボマー， インコーポレイテッド エポキシドから酸無水物を生成するためのプロセス
SG11201405138SA (en) 2012-02-22 2014-11-27 Novomer Inc Acrylic acid production methods
JP5818716B2 (ja) * 2012-02-24 2015-11-18 株式会社日本触媒 不飽和カルボン酸類製造用触媒及びその触媒を用いた不飽和カルボン酸製造方法
US9850192B2 (en) 2012-06-08 2017-12-26 Cj Cheiljedang Corporation Renewable acrylic acid production and products made therefrom
KR20150036034A (ko) 2012-06-27 2015-04-07 노보머, 인코포레이티드 폴리에스터 제조를 위한 촉매 및 방법
CA2878028A1 (en) 2012-07-02 2014-01-09 Novomer, Inc. Process for acrylate production
DE102012212424A1 (de) 2012-07-16 2014-01-16 Basf Se Verfahren zur Herstellung von Acrylsäure durch eine mit wenigstens einer molekularen Wirkverbindung katalysierte Thermolyse von Poly-3-hydroxypropionat
JP2017506286A (ja) 2013-12-07 2017-03-02 ノボマー， インコーポレイテッド ナノろ過膜および使用の方法
US9238210B2 (en) 2013-12-20 2016-01-19 Kellogg Brown & Root Llc Baffle system for fluid catalytic cracking
AU2015229061A1 (en) 2014-03-14 2016-09-22 Novomer, Inc. Catalysts for epoxide carbonylation
US10858329B2 (en) 2014-05-05 2020-12-08 Novomer, Inc. Catalyst recycle methods
SG11201610058QA (en) 2014-05-30 2016-12-29 Novomer Inc Integrated methods for chemical synthesis
WO2016015019A1 (en) 2014-07-25 2016-01-28 Novomer, Inc. Synthesis of metal complexes and uses thereof
MA41510A (fr) 2015-02-13 2017-12-19 Novomer Inc Procédé de production d'acide acrylique
CN111944130B (zh) 2015-02-13 2022-10-25 诺沃梅尔公司 聚丙内酯生产方法和系统
MA41508A (fr) 2015-02-13 2017-12-19 Novomer Inc Systèmes et procédés de production d'acide polyacrylique
MA41514A (fr) 2015-02-13 2017-12-19 Novomer Inc Procédés intégrés de synthèse chimique
MX2017010408A (es) 2015-02-13 2018-02-23 Novomer Inc Procesos continuos de carbonilacion.
WO2016130988A1 (en) 2015-02-13 2016-08-18 Novomer, Inc. Flexible chemical production platform
MA41507A (fr) 2015-02-13 2017-12-19 Novomer Inc Systèmes et procédés de production de polymères
MA41513A (fr) 2015-02-13 2017-12-19 Novomer Inc Procédé de distillation pour la production d'acide acrylique
WO2017004455A1 (en) 2015-07-01 2017-01-05 Novomer, Inc. Polymer compositions produced from biobased ethanol
JP7029804B2 (ja) 2015-07-31 2022-03-04 ノボマー， インコーポレイテッド アクリル酸およびその前駆体のための生成系／生成プロセス
WO2017165345A1 (en) 2016-03-21 2017-09-28 Novomer, Inc. Systems and methods for producing superabsorbent polymers
CA3018208A1 (en) 2016-03-21 2017-09-28 Novomer, Inc. Improved acrylic acid production process
US20180305286A1 (en) 2016-03-21 2018-10-25 Novomer, Inc. Systems and Processes for Producing Organic Acids Direct from Beta-Lactones
US20180282251A1 (en) 2017-03-21 2018-10-04 Novomer, Inc. Systems and processes for producing organic acids direct from beta-lactones
MX2019005095A (es) 2016-11-02 2019-08-12 Novomer Inc Polimeros absorbentes y metodos para producir y usar los mismos.
MA46720A (fr) 2016-11-02 2019-09-11 Novomer Inc Polymères absorbants, procédés et systèmes de production et utilisations correspondantes
US10144802B2 (en) 2016-12-05 2018-12-04 Novomer, Inc. Beta-propiolactone based copolymers containing biogenic carbon, methods for their production and uses thereof
US10500104B2 (en) 2016-12-06 2019-12-10 Novomer, Inc. Biodegradable sanitary articles with higher biobased content
CN106831389B (zh) 2016-12-12 2020-03-31 中国科学技术大学 羧酸类化合物的制备方法
AR110833A1 (es) 2017-01-19 2019-05-08 Novomer Inc Métodos y sistemas para el tratamiento de óxido de etileno
BR112019019313A2 (pt) 2017-03-17 2020-04-14 Novomer Inc poliamidas e métodos de produção das mesmas
US10065914B1 (en) 2017-04-24 2018-09-04 Novomer, Inc. Thermolysis of polypropiolactone to produce acrylic acid
US20190002385A1 (en) 2017-06-30 2019-01-03 Novomer, Inc. Compositions for improved production of acrylic acid
US10781156B2 (en) 2017-06-30 2020-09-22 Novomer, Inc. Compositions for improved production of acrylic acid
US10961209B2 (en) 2017-08-10 2021-03-30 Novomer, Inc. Processes for producing beta-lactone and beta-lactone derivatives with heterogenous catalysts
KR102529865B1 (ko) 2017-09-09 2023-05-09 노보머, 인코포레이티드 아마이드 및 니트릴 화합물 및 이의 제조 및 사용 방법
US20190076834A1 (en) 2017-09-11 2019-03-14 Novomer, Inc. Processes Using Multifunctional Catalysts
US20190076835A1 (en) 2017-09-11 2019-03-14 Novomer, Inc. Processses using multifunctional catalysts
WO2019070981A1 (en) 2017-10-05 2019-04-11 Novomer, Inc. ISOCYANATES, DERIVATIVES, AND THEIR PRODUCTION PROCESSES
WO2020133191A1 (zh) 2018-12-28 2020-07-02 深圳市柔宇科技有限公司 纸沓厚度识别装置、纸沓厚度识别方法及手写输入装置

Also Published As

Publication number Publication date
US20170267618A1 (en) 2017-09-21
JP2019512527A (ja) 2019-05-16
CA3018208A1 (en) 2017-09-28
US11827590B2 (en) 2023-11-28
JP2019509307A (ja) 2019-04-04
ZA201807001B (en) 2019-07-31
BR112018069019A2 (pt) 2019-01-22
AU2017238018A1 (en) 2018-11-08
MX2018011139A (es) 2018-11-21
EP3433226B1 (en) 2021-12-15
EP3433222B1 (en) 2023-03-08
MX2018011485A (es) 2019-03-14
WO2017165344A1 (en) 2017-09-28
CN109153628A (zh) 2019-01-04
CO2018010877A2 (es) 2018-10-22
JP6997459B2 (ja) 2022-02-04
KR20180128018A (ko) 2018-11-30
US20210139402A1 (en) 2021-05-13
BR112018069337A2 (pt) 2019-01-22
KR20180118797A (ko) 2018-10-31
EP3433222A1 (en) 2019-01-30
AU2017236914A1 (en) 2018-11-08
CN114736111A (zh) 2022-07-12
SA518400104B1 (ar) 2022-06-22
EP3433222A4 (en) 2019-11-06
TW201802061A (zh) 2018-01-16
EP3433226A4 (en) 2019-11-06
CN108884000A (zh) 2018-11-23
CN109153628B (zh) 2022-04-26
SA518400053B1 (ar) 2022-04-19
CA3018118A1 (en) 2017-09-28
EP3433226A1 (en) 2019-01-30
WO2017165323A1 (en) 2017-09-28
US10662139B2 (en) 2020-05-26

Similar Documents

Publication Publication Date Title
US11827590B2 (en) Acrylic acid, and methods of producing thereof
KR20100102658A (ko) 프로필렌 글리콜 모노알킬 에테르의 제조
CN113891875B (zh) 联萘类的制造方法
WO2012125218A1 (en) Processes for producing terephthalic acid and terephthalic esters
WO2013069630A1 (ja) イソブタノールからｔ－ブタノールを製造する方法、イソブタノールからメタクロレイン及びメタクリル酸を製造する方法、並びにそれらの製造装置
JP5848819B2 (ja) アダマンチル（メタ）アクリレートの製造方法
KR101679717B1 (ko) 알릴 알코올의 제조방법 및 이에 의하여 제조된 알릴 알코올
WO2014050810A1 (ja) エステル化合物の製造方法及びその方法に用いるパラジウム触媒
KR20170115068A (ko) (메트)아크릴 에스테르 제조 방법에서의 귀중 생성물의 재생
CN107540520B (zh) 一种由频那醇制备均苯四甲酸或偏苯三甲酸的方法
TW202208317A (zh) 生物基丙烯酸的製造方法
CN103232325B (zh) 一种由环己烯制备环己醇的方法
JPH02193944A (ja) （メタ）アクリル酸エステルの製造方法
CN110590555A (zh) 双(2-羟基乙基)对苯二甲酸酯的制法
EP2994450A1 (en) Process of production of dehydrolinalyl acetate (ii)
KR101990384B1 (ko) 고순도 알릴 알코올의 제조 방법 및 고순도 알릴 알코올 제조 공정 시스템
US10570081B2 (en) Process for making formic acid utilizing lower-boiling formate esters
CN112225683B (zh) 一种季戊四醇四巯基羧酸酯的制备方法及其应用
US20170197948A1 (en) Method for producing carboxylic anhydride
KR20170001088A (ko) 아크릴산의 제조 방법
JP6350102B2 (ja) （メタ）アクリル酸エステルの製造方法
EP3268344B1 (en) Bicomponent catalyst and method for dehydrating lactic acid to acrylic acid
JP2016160224A (ja) 第３級アルキル基を有する非対称アルキルエーテルの製造方法
CN109180550A (zh) 一种以铁氧化合物为催化剂制备过氧化酮的方法
CN101100424A (zh) 制备混合碳酸烷基酯的方法

Legal Events

Date Code Title Description
AS Assignment

Owner name: NOVOMER, INC., MASSACHUSETTS

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:SOOKRAJ, SADESH H.;TSEITLIN, ALEXANDER;SIGNING DATES FROM 20180913 TO 20180927;REEL/FRAME:048400/0581

STPP Information on status: patent application and granting procedure in general

Free format text: RESPONSE TO NON-FINAL OFFICE ACTION ENTERED AND FORWARDED TO EXAMINER

STPP Information on status: patent application and granting procedure in general

Free format text: FINAL REJECTION MAILED

STPP Information on status: patent application and granting procedure in general

Free format text: ADVISORY ACTION MAILED

STCB Information on status: application discontinuation

Free format text: ABANDONED -- FAILURE TO RESPOND TO AN OFFICE ACTION