WO2010059770A1 - Agent anti-encrassement pour l'acrylonitrile - Google Patents

Agent anti-encrassement pour l'acrylonitrile Download PDF

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Publication number
WO2010059770A1
WO2010059770A1 PCT/US2009/065057 US2009065057W WO2010059770A1 WO 2010059770 A1 WO2010059770 A1 WO 2010059770A1 US 2009065057 W US2009065057 W US 2009065057W WO 2010059770 A1 WO2010059770 A1 WO 2010059770A1
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WO
WIPO (PCT)
Prior art keywords
styrene sulfonate
water
sulfonate polymer
added
acrylonitrile
Prior art date
Application number
PCT/US2009/065057
Other languages
English (en)
Inventor
David Youdong Tong
Original Assignee
Nalco Company
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 Nalco Company filed Critical Nalco Company
Priority to CN200980146776.1A priority Critical patent/CN102216261B/zh
Priority to KR1020117014080A priority patent/KR101680914B1/ko
Priority to DE112009003654T priority patent/DE112009003654T5/de
Priority to JP2011537599A priority patent/JP5762300B2/ja
Publication of WO2010059770A1 publication Critical patent/WO2010059770A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C253/00—Preparation of carboxylic acid nitriles
    • C07C253/32—Separation; Purification; Stabilisation; Use of additives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C253/00—Preparation of carboxylic acid nitriles
    • C07C253/32—Separation; Purification; Stabilisation; Use of additives
    • C07C253/34—Separation; Purification
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S203/00—Distillation: processes, separatory
    • Y10S203/03—Acrylonitrile
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S977/00—Nanotechnology
    • Y10S977/70—Nanostructure
    • Y10S977/734—Fullerenes, i.e. graphene-based structures, such as nanohorns, nanococoons, nanoscrolls or fullerene-like structures, e.g. WS2 or MoS2 chalcogenide nanotubes, planar C3N4, etc.
    • Y10S977/753—Fullerenes, i.e. graphene-based structures, such as nanohorns, nanococoons, nanoscrolls or fullerene-like structures, e.g. WS2 or MoS2 chalcogenide nanotubes, planar C3N4, etc. with polymeric or organic binder

Definitions

  • This invention relates to a process for the preparation of acrylonitrile and, more particularly, to a process wherein an antifoulant comprising a polymer of styrene sulfonate is added to at least one step in the quench, the recovery and the wastewater process of an acrylonitrile manufacturing process .
  • the manufacture of acrylonitrile comprises three stages, the reaction stage, the recovery stage, and the purification stage.
  • the reaction stage propylene undergoes ammoxidation to form acrylonitrile by reaction with ammonia and oxygen. This often is a gas- phase catalytic reaction at an elevated temperature.
  • the resulting acrylonitrile-containing effluent is then quenched with water and unreacted ammonia is neutralized with sulfuric acid.
  • the quenched product of the reaction stage undergoes a water absorption process to capture acrylonitrile and a recovery process to separate the acrylonitrile from water and other heavy components that also formed during the reaction stage. Water is recycled within the recovery stage.
  • Recovered acrylonitrile is then passed on to the purification stage.
  • fouling compounds tend to form and collect in the recycled water.
  • the fouling compounds include both inorganic and organic compounds in the form of monomers, oligomers, prepolymers, and polymers in various combinations. These fouling compounds form deposits along some of the recovery stage equipment such as heat exchangers, reboilers, and columns. When deposited on the heat exchange surfaces of the heat exchangers and reboilers, the fouling compounds reduce the efficiency of heat transfer equipment. Furthermore, the deposition of foulant creates flow resistance through effected equipment, and even causes blockages in the process flow.
  • Known methods of addressing this problem include adding a dispersant antifoulant to problematic equipment.
  • the dispersant functions as a colloidal stabilizer which keeps foulant suspended in the process stream and prevents foulant from becoming deposited on equipment surfaces.
  • US Patent Number 3,691,226 which describes the use of lignosulfonate metal salts to minimize foulant deposition on the heat transfer surface of the heater exchangers used to cool recycled water.
  • US Patent Number 5,650,072 which teaches the use of naphthalene sulfonate formaldehyde condensate polymer to prevent fouling of heat exchangers in an acrylonitrile stripper.
  • This dispersant prevents the fouling compounds from depositing on the quench and recovery stage equipment.
  • Experimental data has proven that the dispersant is superior to the prior art.
  • FIG. 1 is a general illustration of the manufacturing process of acrylonitrile in which the inventive dispersant is used
  • FIG. 2 is a more detailed illustration of one design in a recovery stage of acrylonitrile manufacture in which the inventive dispersant is used
  • FIG. 3 is a more detailed illustration of another design in a recovery stage of acrylonitrile manufacture in which the inventive dispersant is used.
  • FIG. 1 there is shown a general illustration of the three common stages of the manufacture of acrylonitrile process that the inventive dispersant is added to.
  • the three stages are the reaction stage (25), the recovery stage (24), and the purification stage (23).
  • input propylene (15) reacts with oxygen or air (16) and ammonia (14) within a reactor (1) during an ammoxidation reaction to form acrylonitrile.
  • the reaction effluent then passes on to a quench tower (2) where it is quenched with circulation water (18), and where unreacted ammonia is neutralized with sulfuric acid.
  • the products pass on to the recovery stage where the products enter an absorber column (3).
  • acrylonitrile and heavy components are scrubbed with lean water (26) from light components (such as O % , CO, CO 2 , and unreacted propylene etc.).
  • the acrylonitrile- containing absorber bottom known as rich water (27), is sent to the recovery column (4), while the light components are off gassed (17) through the top of the absorber column (3) and incinerated.
  • the rich water undergoes extraction distillation.
  • Acrylonitrile and hydrogen cyanide are taken off through an overhead portion of the recovery column (4) along with their azeotropes and water.
  • the majority of the water coming with the rich water stream is taken out of the lower section of the recovery column (4) and recycled as lean water to the absorber column (3).
  • Solvent water passes on to the overhead portion as well.
  • a small portion of the water from the recovery column (4) is purged through the bottom of the recovery column (4), and it is either sent back to the quench column or to a waste water process for disposal.
  • the recovery column distillation operation is sustained by reboiler heat exchangers associated with the recovery column (4).
  • the acrylonitrile bearing stream in the overhead portion then passes on to the purification stage (23) where hydrogen cyanide (19), water (20), and heavy materials are separated from the acrylonitrile product (21).
  • the purification stage (23) comprises a recovery overhead decanter (5), heads column (6), dry column (7), heads/dry decanter (8) and product column (9). More information on the ammoxidation reaction to form acrylonitrile can be found in US Patent 3,691,226.
  • rich water water that passes from the absorber column to the recovery column and is concentrated in acrylonitrile.
  • lean water is what remains after the rich water has passed down a recovery column and no longer has acrylonitrile in it.
  • Lean water is recycled back into the absorber column and passes down the column in a countercurrent flow relative to the off-gassed components.
  • solvent water (26) is what remains after the rich water that has also passed down a recovery column and therefore no longer has acrylonitrile in it. The solvent water is fed into the recovery column top section to reduce contamination of the acrylonitrile stream that passes into the decanter (5).
  • FIGs. 2 and 3 show two different designs in the recovery and wastewater handling.
  • a separate stripping column (10) is added, which strips off acetonitrile (22) and light components from the solvent water (26).
  • a multistage evaporation wastewater process (11 and 12) is used to strip water off the recovery bottom purge stream in order to minimize wastewater disposal.
  • the overhead water (28) is recycled back to quench, and the bottom (29) is sent to the wastewater treatment facility.
  • foulant is a material deposit that accumulates on equipment during the operation of a manufacturing and/or chemical process which may be unwanted and which may impair the operation and/or efficiency of the process. Foulant accumulation impedes and blocks liquid throughput in particular through recovery columns.
  • At least one embodiment of the invention is the addition of a styrene sulfonate polymer into one or more of the fluid streams of the acrylonitrile manufacturing process.
  • the styrene sulfonate polymer is a polymeric material comprising the following repeating units:
  • M is hydrogen, alkali metals or ammonium or a mix of them
  • R is hydrogen, alkyl, aryl, alkylaryl, arylalkyl, R may contain heteroatoms, n is an integral ,
  • the styrene sulfonate polymer is introduced into one or more of the fluid streams of the quench column and the recovery stage as well as the wastewater process where it acts as a dispersant that prevents foulant deposition and even facilitates the removal of previously deposited foulant.
  • Previous examples of dispersants used in various manufacturing processes include: sulfonated oils, sulfonated fatty acids, sulfated oils, sulfated fatty acids, naphthalene sulfonate formaldehyde, sulfonic acids, dodecylbenzene sulfonic acid, and lignosulfate metal salts (as described in US Patents 5,650,072, 4,650,072, 5,746,924, and 3,691,226). Experimental data however, proves that in the recovery stage of acrylonitrile manufacture, styrene sulfonate polymer has superior dispersant properties over all of these previous dispersants.
  • the styrene sulfonate polymer provides superior dispersion performance.
  • the dispersant has a molecular weight of 50,000 to 2,000,000 Dalton. In at least one embodiment the dispersant has a molecular weight of at least 100,000 to 1,000,000 Dalton.
  • styrene sulfonate polymer dispersant can be introduced. These include, but are not limited to, the circulation streams of the quench column, the lean water circuit before the lean water cooler exchanger, the solvent water circuit before or after the solvent water cooler exchanger, the feed line to the reboiler, the feed to the stripper column and the feed to the multistage distillation wastewater process.
  • introduction of the dispersant immediately prior to a heat exchanger or reboiler is effective because it provides intact and sufficient amounts of dispersant to the exchanger or reboiler.
  • the effective dosage ranges from 1 to 10,000 ppm by weight, depending upon fouling severity and treatment economics. In practice, a preferred dosage ranges from 5 to 1000 ppm, and the most preferred dosage is from 10 to 200 ppm.
  • the styrene sulfonate polymer dispersant by itself is generally present as solid, and a solvent is generally used to dissolve it and to prepare a liquid formulation. This is generally done when the styrene sulfonate polymer is made. Though styrene sulfonate polymer is soluble in many solvents, water is the solvent most often used for obvious reasons. For economic consideration, highly concentrated styrene sulfonate polymer formulation is generally desirable. Co-solvents may be used with water to enhance solubility and improve product stability and handling.
  • a sample of foulant deposit material was taken from the recovery solvent water cooling exchanger of an acrylonitrile plant.
  • the foulant sample was dried and ground into powder.
  • a foulant solution was prepared by dissolving the foulant powder in an organic solvent.
  • 15 mL of the recovery column solvent water stream of a recovery column from the same acrylonitrile plant was added. 1 mL of the above prepared foulant solution was added to the centrifugal tube. The content in the tube was well shaken and then the tube was allowed to stand at ambient temperature. Precipitation was seen in the tube. After 2.5 hours about 0.5 mL of precipitate was recorded at the bottom of the tube.
  • Example 2A Sample treated with the inventive styrene sulfonate polymer:
  • Example IA The same procedure as in Example IA was performed except that before adding the foulant solution, the contents of the tube were dosed with 39 ppm of the invention styrene sulfonate polymer. This tube did not show any precipitation during the 2-day period of this experiment. This example demonstrates that the inventive styrene sulfonate polymer is an effective dispersant for the fouling situation.
  • Example 3A Sample treated with prior art dispersants: The same procedure as in Example IA was performed except that before adding the foulant solution, the contents of the tube were dosed with 57 ppm of a naphthalene sulfonate polymer. Precipitation did not occur until 20 hours of the settlement. Three days later about 0.2 mL solid precipitate was measured at the bottom of the tube. The naphthalene suflonate polymer is effective only to a certain degree toward this fouling situation.
  • Example IB Dispersion test simulating recovery bottom fouling:
  • a sample of foulant deposit material was taken from the recovery reboiler of an acrylonitrile plant.
  • the foulant sample was dried and ground into powder.
  • a foulant solution was prepared by dissolving the foulant powder in an organic solvent.
  • 15 mL of the bottom purge stream of a recovery column from the same acrylonitrile plant was added. This recovery column bottom stream contained a higher concentration of contaminates and exhibited a lower pH than the solvent water stream.
  • An aliquant of the above prepared foulant solution was added to the same centrifugal tube. The tube contents were shaken well and then the tube was allowed to stand at ambient temperature. Precipitation occurred in less than 5 minutes. After 30 minutes about 3 mL precipitate was recorded at the bottom of the tube.
  • Example 2B Sample treated with styrene sulfonate polymer:
  • Example IB The same procedure as in Example IB was performed except that before adding the foulant solution, the tube content was dosed with 39 ppm of the inventive styrene sulfonate polymer. This tube did not show any precipitation during the 3 -day period of this experiment. This example demonstrates that the inventive styrene sulfonate polymer is an effective dispersant for fouling situations.
  • Example 3B Sample treated with prior art dispersants
  • Example IB The same procedure as in Example IB was performed except that before adding the foulant solution, the tube contents were dosed with 57 ppm of a naphthalene sulfonate polymer. Precipitation occurred after a few minutes. After 30 minutes about 3 mL precipitate was recorded at the bottom of the tube. The naphthalene suflonate polymer is ineffective toward this fouling situation.
  • Example 1C Dispersion test simulating fouling of the recovery reboiler
  • a sample of foulant deposit material was taken from the recovery column reboiler of an acrylonitrile plant. The foulant sample was dried and ground into powder.
  • a foulant solution was prepared by dissolving the foulant powder in an organic solvent.
  • 8 mL of the recovery column bottom purge stream from an acrylonitrile plant was added.
  • 2 microliters of glacial acetic acid was added to the content to lower its pH.
  • 50 microliters of the above prepared foulant solution was added to the same centrifugal tube. The tube was well shaken and then the tube was allowed to stand at elevated temperatures. At about 70 0 C, precipitation occurred in the untreated tube.
  • Example 2C Sample treated with prior art lignosulfonate dispersant: The same procedure as in Example 1C was performed except that before adding the foulant solution, the tube contents were dosed with 39 ppm of a lignosulfonate dispersant. This tube did not show any precipitation at 70° C. However, precipitation was observed when the temperature was raised to 90° C. This example demonstrates the limited effectiveness of the lignosulfonate dispersant.
  • Example 3C Sample treated with prior art naphthalene sulfonate resin dispersant:
  • Example 1C The same procedure as in Example 1C was performed except that before adding the foulant solution, the tube was dosed with 57 ppm of a naphthalene sulfonate polymer. No precipitation was seen at 70 and 90 0 C. Then, an additional 3 microliters of acetic acid was added to the content. Immediately, precipitation was observed. This example shows that the naphthalene suflonate polymer has limited dispersion effect toward this fouling situation.
  • Example 4C Sample treated with the invention styrene sulfonate polymer dispersant :
  • Example 3C The same procedure as in Example 3C was performed except that the tube content was treated with 57 ppm of the inventive styrene sulfonate polymer dispersant. No precipitation was seen at 70 and 90 0 C. No precipitation was observed either with the addition of 3 microliters of acetic acid. This example demonstrates that the styrene suflonate polymer is a more effective dispersant toward this fouling situation than prior art.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

La présente invention concerne un polymère de sulfonate de styrène très efficace pour empêcher l'encrassement d'un équipement utilisé dans le procédé de fabrication de l'acrylonitrile. Ce polymère est particulièrement efficace quand il est introduit dans la colonne de désactivation, l'étage de récupération et la section de traitement des eaux usées du procédé de fabrication de l'acrylonitrile.
PCT/US2009/065057 2008-11-19 2009-11-19 Agent anti-encrassement pour l'acrylonitrile WO2010059770A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
CN200980146776.1A CN102216261B (zh) 2008-11-19 2009-11-19 用于丙烯腈的防污分散剂
KR1020117014080A KR101680914B1 (ko) 2008-11-19 2009-11-19 아크릴로나이트릴용 방오 분산제
DE112009003654T DE112009003654T5 (de) 2008-11-19 2009-11-19 Dispergierendes anti foulj ngmittel für acrylnitril
JP2011537599A JP5762300B2 (ja) 2008-11-19 2009-11-19 アクリロニトリルの製造プロセスにおいて汚損物堆積を防ぐ方法

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US12/274,036 2008-11-19
US12/274,036 US8067629B2 (en) 2008-11-19 2008-11-19 Dispersant antifoulant for acrylonitrile

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WO2010059770A1 true WO2010059770A1 (fr) 2010-05-27

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US (1) US8067629B2 (fr)
JP (1) JP5762300B2 (fr)
KR (1) KR101680914B1 (fr)
CN (1) CN102216261B (fr)
DE (1) DE112009003654T5 (fr)
TW (1) TWI453170B (fr)
WO (1) WO2010059770A1 (fr)

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WO2013027042A1 (fr) 2011-08-19 2013-02-28 Nufarm Uk Limited Nouvelles compositions inhibitrices et procédés d'utilisation
WO2021203256A1 (fr) * 2020-04-08 2021-10-14 Ecolab Usa Inc. Compositions et procédés pour inhiber l'encrassement par sels d'ammonium

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US9656914B2 (en) 2013-05-01 2017-05-23 Ecolab Usa Inc. Rheology modifying agents for slurries
US9034145B2 (en) 2013-08-08 2015-05-19 Ecolab Usa Inc. Use of nanocrystaline cellulose and polymer grafted nanocrystaline cellulose for increasing retention, wet strength, and dry strength in papermaking process
US9410288B2 (en) 2013-08-08 2016-08-09 Ecolab Usa Inc. Use of nanocrystaline cellulose and polymer grafted nanocrystaline cellulose for increasing retention in papermaking process
US9303360B2 (en) 2013-08-08 2016-04-05 Ecolab Usa Inc. Use of nanocrystaline cellulose and polymer grafted nanocrystaline cellulose for increasing retention in papermaking process
US9834730B2 (en) 2014-01-23 2017-12-05 Ecolab Usa Inc. Use of emulsion polymers to flocculate solids in organic liquids
EP3347333B1 (fr) 2015-09-07 2023-07-19 Rhodia Operations Compositions inhibitrices de polymérisation
WO2017066540A1 (fr) 2015-10-15 2017-04-20 Ecolab Usa Inc. Cellulose nanocristalline et cellulose nanocristalline greffée avec un polymère comme agents de modification de la rhéologie pour suspensions d'oxyde de magnésium et de chaux
WO2019018150A1 (fr) 2017-07-17 2019-01-24 Ecolab USA, Inc. Agents de modification de rhéologie pour bouillies
CN113149862B (zh) * 2020-01-07 2022-11-04 中国石油天然气股份有限公司 丙烯腈装置用阻垢分散剂及其评价方法
KR102454907B1 (ko) 2020-06-16 2022-10-17 태광산업주식회사 증류장치 및 증류방법
KR102454912B1 (ko) 2020-06-16 2022-10-17 태광산업주식회사 증류장치 및 증류방법
KR102482497B1 (ko) 2020-06-16 2022-12-29 태광산업주식회사 증류 장치 및 이의 용도
CN114790041A (zh) 2021-01-26 2022-07-26 埃科莱布美国股份有限公司 防冻分散剂及其制造工艺
CN114574225A (zh) * 2022-04-12 2022-06-03 浙江汉景环保化学材料科技有限公司 一种水溶性分散剂

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013027042A1 (fr) 2011-08-19 2013-02-28 Nufarm Uk Limited Nouvelles compositions inhibitrices et procédés d'utilisation
WO2021203256A1 (fr) * 2020-04-08 2021-10-14 Ecolab Usa Inc. Compositions et procédés pour inhiber l'encrassement par sels d'ammonium
EP4132904A4 (fr) * 2020-04-08 2023-12-27 Ecolab USA, Inc. Compositions et procédés pour inhiber l'encrassement par sels d'ammonium

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KR20110087326A (ko) 2011-08-02
CN102216261A (zh) 2011-10-12
US20100125147A1 (en) 2010-05-20
JP5762300B2 (ja) 2015-08-12
CN102216261B (zh) 2014-11-19
JP2012509341A (ja) 2012-04-19
DE112009003654T5 (de) 2012-10-11
US8067629B2 (en) 2011-11-29
KR101680914B1 (ko) 2016-11-29
TW201022161A (en) 2010-06-16
TWI453170B (zh) 2014-09-21

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