Of Alcohol Or Alcoholate Patents (Class 562/519)
  • Patent number: 10457622
    Abstract: Provided is a method for producing acetic acid that is capable of greatly improving the life of a silver-substituted ion exchange resin (IER) for removing organic iodine compounds in acetic acid. With the method for producing acetic acid according to the present invention, in a carbonylation process of a methanol method, a nickel base alloy or zirconium is used as a material of a distillation column in a dehydration step, and as metal ion concentrations in a charging mixture of the distillation column in the dehydration step, an iron ion concentration is less than 10,000 ppb by mass, a chromium ion concentration is less than 5,000 ppb by mass, a nickel ion concentration is less than 3,000 ppb by mass, and a molybdenum ion concentration is less than 2,000 ppb by mass.
    Type: Grant
    Filed: May 25, 2017
    Date of Patent: October 29, 2019
    Assignee: DAICEL CORPORATION
    Inventor: Masahiko Shimizu
  • Patent number: 10308581
    Abstract: There is provided a method allowing industrially efficient production of high quality acetic acid having a good potassium permanganate test value and a low impurity content without a large cost. The method for producing acetic acid according to the present invention has a carbonylation reaction step, an evaporation step and a lower boiling point component removal step, and wherein with heating of the evaporator, (i) an acetaldehyde concentration in the aqueous phase of an overhead condensate in a lower boiling point component removal column is controlled to not less than 2340 ppm by mass; and/or (ii) a methyl acetate concentration in the aqueous phase is controlled to less than 19.0% by mass and/or; (iii) a methyl acetate concentration in the organic phase of the overhead condensate in the lower boiling point component removal column is controlled to less than 38.
    Type: Grant
    Filed: May 25, 2017
    Date of Patent: June 4, 2019
    Assignee: DAICEL CORPORATION
    Inventor: Masahiko Shimizu
  • Patent number: 10293335
    Abstract: This invention relates to a heterogeneous catalyst represented by Rh/C3N4 configured such that a complex of a rhodium compound and 3-benzoylpyridine is immobilized on a carbon nitride support.
    Type: Grant
    Filed: August 24, 2015
    Date of Patent: May 21, 2019
    Assignees: KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY, RESEARCH BUSINESS FOUNDATION SUNGKYUNKWAN UNIVERSITY
    Inventors: Jae Hyun Park, Jong Wook Bae, Tae Sun Chang, Beom Sik Kim
  • Patent number: 10265639
    Abstract: A process for separating or removing permanganate reducing compounds (PRC's) from a first mixture containing at least one PRC, methyl iodide, and water comprises the steps of: feeding the first mixture to a feed port of a distillation column, and distilling and separating the first mixture into an upper stream and a lower stream, wherein the distillation of the first mixture forms a second mixture at an upper position than the feed port, and the process further comprises the steps of: withdrawing the second mixture as the upper stream, and withdrawing the lower stream from a lower position than the feed port.
    Type: Grant
    Filed: January 16, 2017
    Date of Patent: April 23, 2019
    Assignee: Daicel Corporation
    Inventors: Masahiko Shimizu, Yoshihisa Mizutani, Hiroyuki Miura
  • Patent number: 10246398
    Abstract: Processes for producing carboxylic acid are included herein. The processes include contacting an alcohol and carbon monoxide in the presence of a liquid reaction medium under carbonylation conditions sufficient to form a carbonylation product including the carboxylic acid and recovering the carboxylic acid from the carbonylation product. The liquid reaction medium may include a carbonylation catalyst selected from rhodium catalysts, iridium catalysts and palladium catalysts; water in a water concentration ranging from 1 wt. % to 14 wt. % based on the total liquid reaction medium weight; and an additive, one or more in situ generated derivatives of the additive or combinations thereof, wherein the additive includes one or more salts of one or more compounds, each compound including at least one amino group and at least one acid group, the at least one acid group capable of forming an alkali metal salt.
    Type: Grant
    Filed: November 1, 2016
    Date of Patent: April 2, 2019
    Assignee: LyondellBasell Acetyls, LLC
    Inventors: Noel C. Hallinan, David L. Ramage, Daniel F. White
  • Patent number: 10207260
    Abstract: Carbonylation process for producing methyl acetate, by contacting dimethyl ether and carbon monoxide under carbonylation conditions in the presence of a catalyst having a zeolite of micropore volume of 0.01 ml/g. The zeolite is an as-synthesized organic structure directing agent-containing zeolite and contains at least one channel which is defined by an 8-member ring.
    Type: Grant
    Filed: March 6, 2014
    Date of Patent: February 19, 2019
    Assignee: BP Chemicals Limited
    Inventor: John Glenn Sunley
  • Patent number: 10160714
    Abstract: Processes for purifying acetic acid by distilling a process stream in a column in which acetic anhydride is formed in the lower portion of the column. The product stream withdrawn from the column comprises acetic acid, water at a concentration of no more than 0.2 wt. %, and acetic anhydride at a concentration of no more than 600 wppm. The process further comprises hydrating the acetic anhydride in the product stream to form a purified acetic acid product comprising acetic anhydride at a concentration of no more than 50 wppm.
    Type: Grant
    Filed: January 5, 2018
    Date of Patent: December 25, 2018
    Assignee: CELANESE INTERNATIONAL CORPORATION
    Inventors: Ronald D. Shaver, Yaw-Hwa Liu, Mark O. Scates
  • Patent number: 10118885
    Abstract: A carbonylation process for producing acetic acid including: (a) carbonylating methanol or its reactive derivatives in the presence of a Group VIII metal catalyst and methyl iodide promoter to produce a liquid reaction mixture including acetic acid, water, methyl acetate and methyl iodide; and (b) feeding the liquid reaction mixture at a feed temperature to a flash vessel which is maintained at a reduced pressure.
    Type: Grant
    Filed: November 9, 2017
    Date of Patent: November 6, 2018
    Assignee: CELANESE INTERNATIONAL CORPORATION
    Inventor: Jeremy J. Patt
  • Patent number: 10118884
    Abstract: The present disclosure provides for a method for measuring the concentration of one or more components in a reactor or a separation unit of an acetic acid process by Raman spectroscopic analyses. In some embodiments, the conditions in the reactor or in any subsequent step of the acetic acid production process are adjusted in response to the measured concentration of one or more components.
    Type: Grant
    Filed: April 10, 2017
    Date of Patent: November 6, 2018
    Assignee: LyondellBasell Acetyls, LLC
    Inventors: Noel C. Hallinan, David L. Ramage, David A. Heaps
  • Patent number: 9957216
    Abstract: Process for producing acetic acid are disclosed in which a vapor sidedraw is withdrawn from the second column in the primary purification train. The vapor sidedraw comprises acetic acid and lithium-containing compounds at a concentration of no more than 100 wppb. A bottoms stream that is enriched in lithium-containing compounds, such as lithium acetate, or lithium acetate dihydrate, is also withdrawn from the second column. Advantageously, the vapor sidedraw, or a condensed portion thereof, is directly fed to a metal-exchanged ion exchange resin having acid cation exchange sites to produce purified acetic acid. This prevents displacement of the metals in the ion exchange resin.
    Type: Grant
    Filed: November 10, 2016
    Date of Patent: May 1, 2018
    Assignee: CELANESE INTERNATIONAL CORPORATION
    Inventors: Ronald D. Shaver, Yaw-Hwa Liu, Mark O. Scates
  • Patent number: 9862669
    Abstract: This invention relates to processes for producing acetic acid and, in particular, to improved processes for recovering C2+ alkyl halides and removing permanganate reducing compounds formed during the carbonylation of methanol in the presence of a Group VIII metal carbonylation catalyst to produce acetic acid.
    Type: Grant
    Filed: June 12, 2015
    Date of Patent: January 9, 2018
    Assignee: CELANESE INTERNATIONAL CORPORATION
    Inventors: G. Paull Torrence, Raymond J. Zinobile, Oyeyemi F. Oyerinde
  • Patent number: 9695101
    Abstract: A process for producing acetic acid comprising the steps of carbonylating methanol in a reaction medium to form a crude acetic acid product; conveying the crude acetic acid product to a flash vessel at a flash flow rate; flashing the crude acetic acid product to form a first vapor stream comprising acetic acid and a liquid residue stream comprising metal catalyst and halide salt; separating the flashed vapor stream to form a second vapor stream comprising methyl iodide a sidedraw comprising purified acetic acid and water, and a liquid residue stream. The process further comprises the steps of condensing at least a portion of the second vapor stream to form at least one liquid phase and refluxing to the light ends column at least a portion of the at least one liquid phase at a reflux rate. The reflux rate is adjusted based on changes in the flash flow rate.
    Type: Grant
    Filed: October 2, 2015
    Date of Patent: July 4, 2017
    Assignee: CELANESE INTERNATIONAL CORPORATION
    Inventors: Ronald D. Shaver, Yaw-Hwa Liu, Mark O. Scates
  • Patent number: 9611207
    Abstract: The present technology relates to the production and recovery of acetic acid. The recovery processes may include providing a first process stream including acetic acid and greater than 250 ppm of propionic acid; separating at least a portion of the propionic acid from the acetic acid within the first process stream to provide an acetic acid stream including acetic acid and less than 250 ppm of propionic acid and a bottoms stream including propionic acid and acetic acid; reacting the bottoms stream to form a product stream including components of respectively lower boiling points than corresponding components in the bottoms stream; and separating components of the product stream to form an overhead stream including one or more acetates and a bottoms stream including one or more propionates.
    Type: Grant
    Filed: January 27, 2016
    Date of Patent: April 4, 2017
    Assignee: LyondellBasell Acetyls, LLC
    Inventors: Brian A. Salisbury, Sanjeev Deshpande, Michael E. Fitzpatrick, Noel C. Hallinan, John D. Hearn
  • Patent number: 9598342
    Abstract: Processes for the production of acetic acid by carbonylation of methanol and reactive derivatives thereof in a liquid phase reaction medium, wherein the reaction medium comprises a finite amount of water, a homogeneous catalyst, an alkyl halide promoter, and a catalyst stabilizer/co-promoter comprising an imidazolium cation R1R2Im+ as an iodide salt, wherein R1 and R2 are each independently a substituted or unsubstituted alkyl or cycloalkyl, with the proviso that R1 and R2 are not the same.
    Type: Grant
    Filed: March 14, 2014
    Date of Patent: March 21, 2017
    Assignee: CELANESE INTERNATIONAL CORPORATION
    Inventors: Carole Marie Le Berre, Duc Hahn Nguyen, Philippe Gilles Serp, Philippe Kalck, G. Paull Torrence
  • Patent number: 9580377
    Abstract: Process for producing acetic acid is disclosed in which a lithium compound is added to the reaction medium to maintain a concentration of lithium acetate from 0.3 to 0.7 wt. %. The concentration of the rhodium catalyst is maintained from 300 to 3000 wppm in the reaction medium, the concentration of water is maintained from 0.1 to 4.1 wt. % in the reaction medium, and the concentration of methyl acetate is maintained from 0.6 to 4.1 wt. % in the reaction medium.
    Type: Grant
    Filed: February 24, 2016
    Date of Patent: February 28, 2017
    Assignee: CELANESE INTERNATIONAL CORPORATION
    Inventors: Mark O. Scates, Yaw-Hwa Liu
  • Patent number: 9567282
    Abstract: A process for producing acetic acid comprising the steps of reacting carbon monoxide and at least one of methanol and a methanol derivative in a first reactor under conditions effective to produce a crude acetic acid product; separating the crude acetic acid product into at least one derivative stream, at least one of the at least one derivative stream comprising residual carbon monoxide; and reacting at least a portion of the residual carbon monoxide with at least one of methanol and a methanol derivative over a metal catalyst in a second reactor to produce additional acetic acid.
    Type: Grant
    Filed: February 28, 2013
    Date of Patent: February 14, 2017
    Assignee: CELANESE INTERNATIONAL CORPORATION
    Inventors: G. Paull Torrence, Brian W. Hokkanen, Michael O. Nutt, Tianshu Pan, Ronald D. Shaver
  • Patent number: 9550714
    Abstract: The present invention relates to improved processes for the manufacture of acetic acid. A pump around reactor is used to produce additional heat for the production of steam. The pump around reactor receives a portion of the reaction solution produced by the carbonylation reactor and further reacts that portion with additional carbon monoxide and/or reactants.
    Type: Grant
    Filed: August 14, 2013
    Date of Patent: January 24, 2017
    Assignee: CELANESE INTERNATIONAL CORPORATION
    Inventor: Raymond J. Zinobile
  • Patent number: 9540302
    Abstract: Processes for the producing acetic acid and, in particular, to improved processes for removing a cation, such as lithium, and iodides from a low energy carbonylation process to produce purified acetic acid. In one embodiment, the cation, e.g., lithium, may be removed using a cationic exchanger prior to removing iodides using a metal-exchanged ion exchange resin. The present invention is suited for removing at least one cation selected from the group consisting of Groups IA and IIA of the periodic table, quaternary nitrogen cations, and phosphorous-containing cations.
    Type: Grant
    Filed: April 23, 2015
    Date of Patent: January 10, 2017
    Assignee: CELANESE INTERNATIONAL CORPORATION
    Inventors: Mark O. Scates, Sarah Lane Abrego, Yaw-Hwa Liu, Ronald D. Shaver
  • Patent number: 9540304
    Abstract: A process for producing an acetic acid product having low butyl acetate content via a carbonylation reaction. The carbonylation reaction is carried out at a temperature from 100 to 300° C., a hydrogen partial pressure from 0.3 to 2 atm, and a rhodium catalyst concentration from 100 to 3000 wppm, based on the weight of the reaction medium. The butyl acetate concentration in the acetic acid product may be controlled by removing acetaldehyde from a stream derived from the reaction medium and/or by adjusting at least one of reaction temperature, hydrogen partial pressure, and metal catalyst concentration.
    Type: Grant
    Filed: October 2, 2015
    Date of Patent: January 10, 2017
    Assignee: CELANESE INTERNATIONAL CORPORATION
    Inventors: Yaw-Hwa Liu, Mark O. Scates
  • Patent number: 9487464
    Abstract: The disclosure is directed to a carbonylation process for producing acetic acid which includes separating a vapor product stream from a carbonylation reactor to produce a crude acid product comprising acetic acid comprising lithium cations and contacting the crude acetic acid product with a cationic exchanger in the acid form within a first treatment device to produce an intermediate acid product; and contacting the intermediate acetic acid product with a metal-exchanged ion exchange resin having acid cation exchange sites within a second treatment device to produce a purified acetic acid. Embodiments directed to a treatment device comprising a plurality of sampling ports having a first open flow path and a second flow path comprising a porous element are disclosed.
    Type: Grant
    Filed: October 2, 2015
    Date of Patent: November 8, 2016
    Assignee: CELANESE INTERNATIONAL CORPORATION
    Inventors: Ronald David Shaver, Yaw-Haw Liu, Mark O Scates, Sarah Lane Abrego
  • Patent number: 9458077
    Abstract: Processes for producing acetic acid wherein at least one process vent stream is treated in an absorber column that utilizes a scrubber solvent, e.g., acetic acid, methanol, and/or methyl acetate to remove hydrogen iodide therefrom.
    Type: Grant
    Filed: October 2, 2015
    Date of Patent: October 4, 2016
    Assignee: CELANESE INTERNATIONAL CORPORATION
    Inventors: Ronald D. Shaver, Yaw-Hwa Liu, Mark O. Scates
  • Patent number: 9440902
    Abstract: To provide a production method for suppressing the reduction in production rate of a carbonyl compound due to transferring a noble metal component into liquid phase. A method for producing a carbonyl compound, including: a reaction step of reacting a carbonylation raw material with CO in liquid phase including a solid catalyst having noble metal complex on a resin carrier containing quaternized nitrogen to produce a carbonyl compound; a distillation step of distilling a reaction product liquid to recover gas phase distillate including the carbonyl compound; and a circulation step of circulating a bottom product from the distillation to reaction step. After part of the bottom product contacts with an acidic cation-exchange resin to remove nitrogen compound, liquid having higher moisture concentration than the bottom product contacts with the resin to extract noble metal complex captured by oligomer adsorbing the resin, and the complex is returned to the reaction step.
    Type: Grant
    Filed: June 3, 2014
    Date of Patent: September 13, 2016
    Assignee: CHIYODA CORPORATION
    Inventors: Zhixiong You, Yoichi Umehara, Tetsuro Matsumura, Takeshi Minami
  • Patent number: 9409848
    Abstract: Processes for the reduction and/or removal of permanganate reducing compounds (PRC'S) formed by the carbonylation of methanol in the presence of a Group VIII metal carbonylation catalyst to produce acetic acid are disclosed. More specifically, processes for reducing and/or removing PRC's or their precursors from intermediate streams during the formation of acetic acid by said carbonylation processes are disclosed. In particular, processes in which a low boiling overhead vapor stream from a light ends column is subjected to a distillation to obtain an overhead that is subjected to an extraction to selectively remove and/or reduce PRC's from the process is disclosed. The processes include steps of recycling one or more return streams derived from the distillation step and/or the extraction step to a light ends column and/or a drying column in order to improve water control in the overall reaction system.
    Type: Grant
    Filed: September 9, 2015
    Date of Patent: August 9, 2016
    Assignee: CELANESE INTERNATIONAL CORPORATION
    Inventors: Ronald D. Shaver, Mark O. Scates, Raymond J. Zinobile
  • Patent number: 9387469
    Abstract: Carbonylation catalysts and methods for using them are disclosed. In some embodiments, the carbonylation catalyst includes the contact product of: (a) a nitrogen compound selected from monomeric pyridines and imidazoles; (b) a Group VIII metal; and (c) an alkali metal compound; wherein the catalyst material is on a solid support.
    Type: Grant
    Filed: December 30, 2013
    Date of Patent: July 12, 2016
    Assignee: Eastman Chemical Company
    Inventors: Zhidong George Zhu, Gerald Charles Tustin, Joseph Robert Zoeller, Craig Steven Dunn, Larry Ronnie Lingerfelt, Mary Kathleen Moore
  • Patent number: 9346733
    Abstract: Eductor mixers are used to mix the reaction medium in a carbonylation reactor. A portion of the reaction solution withdrawn from the reactor and directed through a pump around loop. The pump around loop is fed back to the reactor through the eductor mixers. In addition, a pump around loop may pass through one or more steam generators and/or heat exchangers.
    Type: Grant
    Filed: September 19, 2013
    Date of Patent: May 24, 2016
    Assignee: CELANESE INTERNATIONAL CORPORATION
    Inventors: Raymond J. Zinobile, Michael Lakin, Ashok Rakhe, Ronald D. Shaver
  • Patent number: 9278346
    Abstract: A hydrodeoxygenation catalyst comprises a metal catalyst, an acid promoter, and a support. The metal catalyst is selected from platinum, palladium, ruthenium, rhenium rhodium, osmium, iridium, nickel, cobalt, molybdenum, copper, tin, or mixtures thereof. The support is a promoted-zirconium material including texture promoters and acid promoters. The hydrodeoxygenation catalyst may be used for hydrodeoxygenation (HDO) of sugar or sugar alcohol in an aqueous solution. In one embodiment the HDO catalyst may be used for HDO of fatty acids such as fatty acid methyl esters (FAME), triglycerols (in plant oil and animal fat), pyrolysis oil, or lignin. The hydrodeoxygenation catalyst for fatty acid process does not require the use of an acid promoter, it is optional.
    Type: Grant
    Filed: July 25, 2012
    Date of Patent: March 8, 2016
    Assignee: CLARIANT CORPORATION
    Inventors: Wenqin Shen, Alguo Liu, Wayne Turbeville
  • Patent number: 9216936
    Abstract: This invention relates to processes for producing acetic acid and, in particular, to improved processes for recovering C2+ alkyl halides and removing permanganate reducing compounds formed during the carbonylation of methanol in the presence of a Group VIII metal carbonylation catalyst to produce acetic acid.
    Type: Grant
    Filed: October 13, 2011
    Date of Patent: December 22, 2015
    Assignee: Celanese International Corporation
    Inventors: G. Paull Torrence, Raymond Zinobile, Oyeyemi Oyerinde
  • Patent number: 9149735
    Abstract: Processes for the reduction and/or removal of permanganate reducing compounds (PRC'S) formed by the carbonylation of methanol in the presence of a Group VIII metal carbonylation catalyst to produce acetic acid are disclosed. More specifically, processes for reducing and/or removing PRC's or their precursors from intermediate streams during the formation of acetic acid by said carbonylation processes are disclosed. In particular, processes in which a low boiling overhead vapor stream from a light ends column is subjected to a distillation to obtain an overhead that is subjected to an extraction to selectively remove and/or reduce PRC's from the process is disclosed. The processes include steps of recycling one or more return streams derived from the distillation step and/or the extraction step to a light ends column and/or a drying column in order to improve water control in the overall reaction system.
    Type: Grant
    Filed: September 17, 2014
    Date of Patent: October 6, 2015
    Assignee: Celanese International Corporation
    Inventors: Ronald D. Shaver, Mark O. Scates, Raymond J. Zinobile
  • Patent number: 9102612
    Abstract: A process for producing acetic acid includes: obtaining hydrogen iodide in an acetic acid production system; and continually introducing a complexing agent into the system, wherein the complexing agent and hydrogen iodide interact to form a complex.
    Type: Grant
    Filed: June 25, 2012
    Date of Patent: August 11, 2015
    Assignee: LyondellBasell Acetyls, LLC
    Inventors: Noel C. Hallinan, Brian A Salisbury, Wayne J Brtko, Michael E Fitzpatrick
  • Publication number: 20150148562
    Abstract: The invention relates to processes for removing aromatics from the reactants that are fed to a carbonylation reactor. The aromatics are removed using a guard bed that comprises an adsorbent.
    Type: Application
    Filed: February 3, 2015
    Publication date: May 28, 2015
    Applicant: CELANESE INTERNATIONAL CORPORATION
    Inventors: G. Paull Torrence, Ronald David Shaver, Yaw-Hwa Liu
  • Patent number: 9024061
    Abstract: A carbonylation process for making acetic acid using a metallic co-catalyst composition, effective as a rhodium stabilizer and/or rate promoter, at molar ratios of metal/rhodium of about 0.5 to 40. The process includes reacting methanol with carbon monoxide in the presence of a rhodium-based catalytic metal complex with about 1 to 20 weight percent methyl iodide, less than about 8 weight % water and about 0.5 to about 30 weight percent methyl acetate. The crude acetic acid is flashed and further purified.
    Type: Grant
    Filed: June 14, 2010
    Date of Patent: May 5, 2015
    Assignee: Celanese International Corporation
    Inventors: Carole M. Le Berre, Samuel Gautron, Philippe J. Kalck, Philippe G. Serp, Nicolas D. Lassauque, G. Paull Torrence
  • Patent number: 9006483
    Abstract: A production process of acetic acid according to the present invention inhibits concentration of hydrogen iodide and improves a liquid-liquid separation of an overhead from a distillation column. Acetic acid is produced by distilling a mixture containing hydrogen iodide, water, acetic acid and methyl acetate in a first distillation column (3) to form an overhead and a side cut stream or bottom stream containing acetic acid, cooling and condensing the overhead in a condenser (C3) to form separated upper and lower phases in a decanter (4). According to this process, a zone having a high water concentration is formed in the distillation column above the feed position of the mixture by feeding a mixture having a water concentration of not less than an effective amount to not more than 5% by weight (e.g., 0.5 to 4.5% by weight) and a methyl acetate concentration of 0.5 to 9% by weight (e.g., 0.5 to 8% by weight) as the mixture to the distillation column and distilling the mixture.
    Type: Grant
    Filed: March 12, 2013
    Date of Patent: April 14, 2015
    Assignee: Daicel Corporation
    Inventors: Masahiko Shimizu, Hiroyuki Miura, Takashi Ueno, Hidehiko Nakajima
  • Patent number: 8987512
    Abstract: A carbonylation process for producing acetic acid including: (a) carbonylating methanol or its reactive derivatives in the presence of a Group VIII metal catalyst and methyl iodide promoter to produce a liquid reaction mixture including acetic acid, water, methyl acetate and methyl iodide; (b) feeding the liquid reaction mixture at a feed temperature to a flash vessel which is maintained at a reduced pressure; (c) heating the flash vessel while concurrently flashing the reaction mixture to produce a crude product vapor stream, wherein the reaction mixture is selected and the flow rate of the reaction mixture fed to the flash vessel as well as the amount of heat supplied to the flash vessel is controlled such that the temperature of the crude product vapor stream is maintained at a temperature less than 90° F.
    Type: Grant
    Filed: July 8, 2014
    Date of Patent: March 24, 2015
    Assignee: Celanese International Corporation
    Inventor: Jeremy J. Patt
  • Publication number: 20150080604
    Abstract: Described herein are methods for preparing acrylic acid from biobased starting materials, e.g., ethanol.
    Type: Application
    Filed: September 16, 2014
    Publication date: March 19, 2015
    Inventor: JOSHUA LENSBOUER
  • Patent number: 8957248
    Abstract: A production process of acetic acid comprises a reaction step for continuously allowing at least one member selected from the group consisting of methanol, dimethyl ether, and methyl acetate to react with carbon monoxide in a catalyst system comprising a rhodium catalyst, an iodide salt, and methyl iodide in the presence of acetic acid and water in a plant compromising a reactor 1; a flasher 2; and a distillation column 3; wherein part of the vaporized stream is introduced into a heat exchanger 7. The process achieves a production of acetic acid with a high purity in a resource-saving and energy-saving equipment by efficiently removing a reaction heat even in a large-sized plant.
    Type: Grant
    Filed: July 11, 2011
    Date of Patent: February 17, 2015
    Assignee: Daicel Corporation
    Inventors: Hiroyuki Miura, Masahiko Shimizu, Takashi Ueno, Kazuo Yamaguchi, Kensuke Goto
  • Patent number: 8952196
    Abstract: The invention relates to processes for removing aromatics from the reactants that are fed to a carbonylation reactor. The aromatics are removed using a guard bed that comprises an adsorbent.
    Type: Grant
    Filed: May 3, 2012
    Date of Patent: February 10, 2015
    Assignee: Celanese International Corporation
    Inventors: G. Paull Torrence, Ronald David Shaver, Yaw-Hwa Liu
  • Patent number: 8940932
    Abstract: A process for stably producing high purity acetic acid comprising a condensation step for condensing and temporarily holding the lower boiling component in a decanter and discharging from the decanter; and a step for separating the lower boiling component discharged from the decanter into acetaldehyde and a liquid residue and recycling the liquid residue to the reaction system. In the condensation step, the amount of the lower boiling component to be held is controlled based on the fluctuating flow rate of the lower boiling component to be fed to the decanter.
    Type: Grant
    Filed: September 27, 2011
    Date of Patent: January 27, 2015
    Assignee: Daicel Corporation
    Inventor: Masahiko Shimizu
  • Publication number: 20150025270
    Abstract: A production process of acetic acid according to the present invention inhibits concentration of hydrogen iodide and improves a liquid-liquid separation of an overhead from a distillation column. Acetic acid is produced by distilling a mixture containing hydrogen iodide, water, acetic acid and methyl acetate in a first distillation column (3) to form an overhead and a side cut stream or bottom stream containing acetic acid, cooling and condensing the overhead in a condenser (C3) to form separated upper and lower phases in a decanter (4). According to this process, a zone having a high water concentration is formed in the distillation column above the feed position of the mixture by feeding a mixture having a water concentration of not less than an effective amount to not more than 5% by weight (e.g., 0.5 to 4.5% by weight) and a methyl acetate concentration of 0.5 to 9% by weight (e.g., 0.5 to 8% by weight) as the mixture to the distillation column and distilling the mixture.
    Type: Application
    Filed: March 12, 2013
    Publication date: January 22, 2015
    Applicant: DAICEL CORPORATION
    Inventors: Masahiko Shimizu, Hiroyuki Miura, Takashi Ueno, Hidehiko Nakajima
  • Patent number: 8916727
    Abstract: Processes for the production of acetic acid by carbonylation of methanol and reactive derivatives thereof in a liquid phase reaction medium, wherein the reaction medium comprises a finite amount of water, a homogeneous catalyst, an alkyl halide promoter, and a catalyst stabilizer/co-promoter comprising a dissymmetric phosphonium cation.
    Type: Grant
    Filed: December 14, 2012
    Date of Patent: December 23, 2014
    Assignee: Celanese International Corporation
    Inventors: Carole Marie Le Berre, Duc Hanh Nguyen, Phillipe Gilles Serp, Philippe Joseph Kalck, G. Paull Torrence
  • Publication number: 20140350296
    Abstract: An alcohol such as methanol is reacted with carbon monoxide in a liquid reaction medium including a catalyst, an alkyl iodide such as methyl iodide, alkyl acetate such as methyl acetate in specified proportions, an additive, and an effective amount of water, where the additive increases an ionic character of the hydrogen iodide bond and the effective amount of water is sufficient to facilitate carboxylic acid release after carbonylation at the catalyst and to reduce anhydride formation. The present reaction system not only provides an acid product at water levels considerable below levels currently used, but also provides unexpected reaction rates and unexpected high catalyst stability.
    Type: Application
    Filed: April 4, 2014
    Publication date: November 27, 2014
    Applicant: PRETIUM VENTURES AA, LLC
    Inventors: Ronnie M. Hanes, Peter P. Hanik, James A. Hinnenkamp
  • Patent number: 8877963
    Abstract: The present invention is to a process for producing acetic acid comprising the step of reacting a carbon monoxide feed and methanol and/or a methanol derivative in a first reactor to produce a crude acetic acid product. The carbon monoxide may comprise less than 99.5 mol % carbon monoxide. The process further comprises the step of purging a carbon monoxide purge stream comprising a first amount of residual carbon monoxide and one or more impurities. Preferably, the first amount is greater than 20 mol %. The process further comprises the step of separating the crude acetic acid product into at least one derivative stream comprising a second amount of residual carbon monoxide. The process further comprises the step of reacting at least a portion of the second amount of residual carbon monoxide and methanol and/or a methanol derivative in a second reactor to produce additional acetic acid.
    Type: Grant
    Filed: September 13, 2011
    Date of Patent: November 4, 2014
    Assignee: Celanese International Corporation
    Inventors: Brian W. Hokkanen, Michael Nutt, Tianshu Pan, Ronald David Shaver, G. Paull Torrence
  • Publication number: 20140323760
    Abstract: A carbonylation process for producing acetic acid including: (a) carbonylating methanol or its reactive derivatives in the presence of a Group VIII metal catalyst and methyl iodide promoter to produce a liquid reaction mixture including acetic acid, water, methyl acetate and methyl iodide; (b) feeding the liquid reaction mixture at a feed temperature to a flash vessel which is maintained at a reduced pressure; (c) heating the flash vessel while concurrently flashing the reaction mixture to produce a crude product vapor stream, wherein the reaction mixture is selected and the flow rate of the reaction mixture fed to the flash vessel as well as the amount of heat supplied to the flash vessel is controlled such that the temperature of the crude product vapor stream is maintained at a temperature less than 90° F.
    Type: Application
    Filed: July 8, 2014
    Publication date: October 30, 2014
    Inventor: Jeremy J. Patt
  • Publication number: 20140309455
    Abstract: Processes for the production of acetic acid by carbonylation of methanol and reactive derivatives thereof in a liquid phase reaction medium, wherein the reaction medium comprises a finite amount of water, a homogeneous catalyst, an alkyl halide promoter, and a catalyst stabilizer/co-promoter comprising an imidazolium cation R1R2Im+ as an iodide salt, wherein R1 and R2 are each independently a substituted or unsubstituted alkyl or cycloalkyl, with the proviso that R1 and R2 are not the same.
    Type: Application
    Filed: March 14, 2014
    Publication date: October 16, 2014
    Applicant: Celanese International Corporation
    Inventors: Carole Marie Le Berre, Duc Hahn Nguyen, Philippe Gilles Serp, Philippe Kalck, G. Paull Torrence
  • Publication number: 20140275620
    Abstract: The present invention is related to separating product gas using a carbonylation reactor in which the carbon monoxide is consumed to produce acetic acid, and hydrogen and carbon dioxide are recovered. The recovered hydrogen may be further purified to reduce the concentration of carbon oxides. The present invention provides improved methods for converting product gas or syngas to ethanol.
    Type: Application
    Filed: March 14, 2014
    Publication date: September 18, 2014
    Applicant: Celanese International Corporation
    Inventor: G. Paull Torrence
  • Patent number: 8835681
    Abstract: A carbonylation process for making acetic acid using a metallic co-catalyst composition, effective as a rhodium stabilizer and/or rate promoter, at molar ratios of metal/rhodium of about 0.5 to 40. The process includes reacting methanol with carbon monoxide in the presence of a rhodium-based catalytic metal complex with about 1 to 20 weight percent methyl iodide, less than about 8 weight % water and about 0.5 to about 30 weight percent methyl acetate. The crude acetic acid is flashed and further purified. This process is stable in the absence of a lithium iodide cocatalyst, or in low concentrations of lithium iodide, with an STY greater than 10 mol/L/hr.
    Type: Grant
    Filed: December 4, 2012
    Date of Patent: September 16, 2014
    Assignee: Celanese International Corporation
    Inventors: Carole M. Le Berre, Samuel Gautron, Philippe J. Kalck, Philippe G. Serp, Nicolas D. Lassauque, G. Paull Torrence
  • Patent number: 8802893
    Abstract: According to a method for producing acetic acid by carbonylation of methanol characterized in that an acid having an acid dissociation constant (pKa) smaller than the constant of acetic acid is allowed to be present in the reaction system, acetic acid can be produced by the reaction of methanol and carbon monoxide in a reaction liquid in the presence of a solid catalyst containing rhodium and alkyl iodide, to achieve an enhanced reaction rate of carbonylation of methanol in producing acetic acid in the region at a high carbonylation degree (Ca>0.8 mol/mol) for more efficient production of acetic acid.
    Type: Grant
    Filed: February 8, 2011
    Date of Patent: August 12, 2014
    Assignee: Chiyoda Corporation
    Inventors: Zhixiong You, Takeshi Minami, Chunji Yin, Yoichi Umehara, Tetsuro Matsumura, Chikako Hashimoto, Yasuo Hosono
  • Patent number: 8785684
    Abstract: A carbonylation process for making acetic acid uses a metallic co-catalyst composition effective as a rhodium stabilizer and rate promoter at molar ratios of metal/rhodium of from about 0.5 to 30. A preferred process includes: (a) reacting methanol with a carbon monoxide feedstock in a rhodium-based catalytic reaction mixture having: (i) a rhodium catalyst metal, (ii) methyl iodide maintained from about 1 to 20 weight percent, (iii) a lithium iodide co-catalyst, (iv) a metallic co-catalyst composition, (v) water maintained from 0.1 weight percent to less than 8 weight percent, (vi) methyl acetate maintained from about 0.5 to about 30 weight percent, and (vii) acetic acid; (b) flashing crude acetic acid from the reaction mixture; and (c) purifying the crude acetic acid. This process achieves stability and a STY greater than 10 mol/L/hr, with substantially less than a theoretically equivalent inorganic iodide content corresponding to the metallic co-catalyst and lithium iodide.
    Type: Grant
    Filed: December 4, 2012
    Date of Patent: July 22, 2014
    Assignee: Celanese International Corporation
    Inventors: Carole M. Le Berre, Samuel Gautron, Philippe J. Kalck, Philippe G. Serp, Nicolas D. Lassauque, G. Paull Torrence
  • Patent number: 8771616
    Abstract: A carbonylation process for producing acetic acid including: (a) carbonylating methanol or its reactive derivatives in the presence of a Group VIII metal catalyst and methyl iodide promoter to produce a liquid reaction mixture including acetic acid, water, methyl acetate and methyl iodide; (b) feeding the liquid reaction mixture at a feed temperature to a flash vessel which is maintained at a reduced pressure; (c) heating the flash vessel while concurrently flashing the reaction mixture to produce a crude product vapor stream, wherein the reaction mixture is selected and the flow rate of the reaction mixture fed to the flash vessel as well as the amount of heat supplied to the flash vessel is controlled such that the temperature of the crude product vapor stream is maintained at a temperature less than 90° F.
    Type: Grant
    Filed: November 5, 2012
    Date of Patent: July 8, 2014
    Assignee: Celanese International Corporation
    Inventor: Jeremy J. Patt
  • Publication number: 20140187812
    Abstract: The invention provides systems and processes for concentrating acetic acid and acetic anhydride streams. The systems allow operation of equipment used for such concentrations in two or more modes of operation. At least one mode is intended to produce a concentrated or purified acetic acid stream. At least one other mode is intended to produce a concentrated or purified acetic anhydride stream.
    Type: Application
    Filed: March 14, 2013
    Publication date: July 3, 2014
    Applicant: Eastman Chemical Company
    Inventors: Gregory Abbott Wellman, JR., Joseph Nathaniel Bays, Robert Sterling Kline
  • Patent number: 8742168
    Abstract: The disclosure relates to a process in which methanol is carbonylated in a reaction zone in the presence of a catalyst to obtain a reaction mixture (A) comprising acetic acid, hydrogen iodide, methyl iodide, water and the catalyst. At least a part of the reaction mixture (A) is withdrawn from the reaction zone. The withdrawn part of the reaction mixture (A) is introduced into a flash zone where it is brought into contact with an alkylimidazolium iodide to form a secondary mixture (B), and where the secondary mixture (B) is separated to obtain a vapor stream (BV) which comprises the acetic acid, water and methyl iodide, and a liquid stream (BL) which comprises the catalyst, the alkylimidazolium iodide and hydrogen iodide. The vapor stream (BV) is processed to purify the acetic acid, and the liquid stream (BL) is recycled to the reaction zone.
    Type: Grant
    Filed: May 31, 2011
    Date of Patent: June 3, 2014
    Assignee: Lyondell Chemical Technology, L.P.
    Inventors: Noel C. Hallinan, Brian Salisbury, Wayne Joseph Brtko