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EP2027066A1 - Procédé pour séparer du monoxyde de carbone d'un gaz contenant du chlorure d'hydrogène - Google Patents

Procédé pour séparer du monoxyde de carbone d'un gaz contenant du chlorure d'hydrogène

Info

Publication number
EP2027066A1
EP2027066A1 EP07725286A EP07725286A EP2027066A1 EP 2027066 A1 EP2027066 A1 EP 2027066A1 EP 07725286 A EP07725286 A EP 07725286A EP 07725286 A EP07725286 A EP 07725286A EP 2027066 A1 EP2027066 A1 EP 2027066A1
Authority
EP
European Patent Office
Prior art keywords
phosgene
hydrogen chloride
carbon monoxide
gas
separation
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.)
Withdrawn
Application number
EP07725286A
Other languages
German (de)
English (en)
Inventor
Michel Haas
Dietmar Wastian
Tim Loddenkemper
Bernd RÜFFER
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.)
Covestro Deutschland AG
Original Assignee
Bayer MaterialScience AG
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 Bayer MaterialScience AG filed Critical Bayer MaterialScience AG
Publication of EP2027066A1 publication Critical patent/EP2027066A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B7/00—Halogens; Halogen acids
    • C01B7/01—Chlorine; Hydrogen chloride
    • C01B7/07—Purification ; Separation
    • C01B7/0706—Purification ; Separation of hydrogen chloride
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B7/00—Halogens; Halogen acids
    • C01B7/01—Chlorine; Hydrogen chloride
    • C01B7/07—Purification ; Separation
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
    • B01D53/34—Chemical or biological purification of waste gases
    • B01D53/46—Removing components of defined structure
    • B01D53/62—Carbon oxides
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B13/00—Oxygen; Ozone; Oxides or hydroxides in general
    • C01B13/14—Methods for preparing oxides or hydroxides in general
    • C01B13/16—Purification
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B32/00—Carbon; Compounds thereof
    • C01B32/80—Phosgene
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D2251/00—Reactants
    • B01D2251/50—Inorganic acids
    • B01D2251/502—Hydrochloric acid
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D2257/00—Components to be removed
    • B01D2257/50—Carbon oxides
    • B01D2257/502—Carbon monoxide
    • 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
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/20—Air quality improvement or preservation, e.g. vehicle emission control or emission reduction by using catalytic converters

Definitions

  • the present invention relates to a process for the separation of carbon monoxide from a hydrogen chloride-containing gas, which comprises the reaction of the carbon monoxide with chlorine to form phosgene and the subsequent separation of the phosgene from the hydrogen chloride-containing gas.
  • the hydrogen chloride-containing gas used preferably originates from the phosgenation or isocyanate formation reaction.
  • the process according to the invention is preferably used as part of the chlorine cycle of the isocyanate formation reaction.
  • CO carbon monoxide
  • a greater amount of carbon monoxide (CO) may be present as an impurity in the HCl exhaust gas.
  • CO contents in the range from 0 to 3% by volume are generally found in the HCl offgas of the phosgene wash-off column.
  • gas-phase phosgenation DE 42 17 019 A1, DE 103 07 141 A1
  • higher amounts of CO (0 to more than 5% by volume) are to be expected, since in this process preferably no condensation of phosgene, and one with it Connected separation of carbon monoxide, before the phosgenation is performed.
  • a cause for the Catalyst deactivation lies in the known microstructural change of the catalyst surface, for example by sintering processes, due to the hot-spot formation. Furthermore, the adsorption of carbon monoxide on the surface of the catalyst can not be excluded.
  • the formation of metal carbonyls can be reversible or irreversible and thus be in direct competition with HCl oxidation. In fact, carbon monoxide with some elements, such as osmium, rhenium, ruthenium (see Chem. Rev. 103, 3707-3732, 2003), can form very stable bonds even at high temperatures and thus cause an inhibition of the desired target reaction. Another disadvantage could arise from the volatility of these metal carbonyls (see Chem. Rev., 21, 3-38, 1937), whereby not inconsiderable amounts of catalyst are lost and, in addition, require a complicated purification step, depending on the application.
  • JP-A-62-270404 (EP-A-0233773) describes a method for HCl oxidation with oxygen, wherein the carbon monoxide content of the gas used is previously adjusted to less than 10 vol .-% by
  • the exhaust gas containing hydrogen chloride is passed into an aqueous alkaline absorption system and the exhaust gas freed of hydrogen chloride and phosgene is fed to a combustion plant.
  • the inventive method dispenses in particular with the separation of CO from the phosgene, in whose synthesis it is used in excess, by the particularly energy-consuming condensation of the phosgene.
  • the carbon monoxide can be left in the phosgene during the isocyanate formation, and is subsequently separated from the exhaust gas before the HCl oxidation by the process according to the invention.
  • the formation of hotspots and the associated catalyst deactivation due to the exothermic formation of CO from CO are not to be feared. Furthermore, there is no accumulation of carbon dioxide in the recycle stream in the Deacon process.
  • the present invention thus provides a process for separating carbon monoxide from a hydrogen chloride-containing gas, which comprises reacting the carbon monoxide with chlorine to form phosgene.
  • the separation of the phosgene then takes place from the gas containing hydrogen chloride, which is subsequently subjected to the hydrogen chloride oxidation by the Deacon process.
  • all gases containing hydrogen chloride (HCl) and carbon monoxide (CO) can be used in the process according to the invention. Preference is given to process gases resulting from isocyanate production by reaction of organic amines with phosgene or gases resulting from the chlorination of hydrocarbons.
  • the hydrogen chloride-containing gases used have, for example, from about 0.1 to about 20% by volume, preferably from about 0.5 to 15% by volume, of carbon monoxide.
  • the content of hydrogen chloride is, for example, from 20 to 99.5% by volume, preferably from 50 to 99.5% by volume.
  • the remaining gases of the hydrogen chloride-containing gas are, for example, nitrogen, oxygen, carbon dioxide and noble gases. They form, for example, from about 0.5 to 80% by volume of the hydrogen chloride-containing gas.
  • the reaction of the carbon monoxide in the hydrogen chloride-containing gas used takes place in a manner known per se, in particular by the reaction of the carbon monoxide with chlorine to form phosgene, for example on an activated carbon catalyst.
  • Alternative catalysts can also be used.
  • Reference may be made to the prior art eg DE 3327274; GB 583477; WO 97/30932; WO 96/16898; US 6713035), the content of which belongs to the Offenbamngsgehalt the present patent application.
  • ⁇ pressure range from 1 to about 20 bar
  • the separation of the carbon monoxide can be carried out with a molar excess of chlorine in order to remove the carbon monoxide as completely as possible
  • an excess of carbon monoxide is used to prevent residual chlorine in the phosgene formed.
  • the phosgene formed is generally separated by at least one operation selected from the group consisting of:
  • the liquefaction may optionally after previous drying of the gas mixture, such as in DE-A-1,567,599, GB 737 442 describes take place (the content of which is part of the disclosure of the present application).
  • the separation of the phosgene by condensation or distillation.
  • the thus separated phosgene is preferably recycled to a phosgenation reaction, in particular the isocyanate production.
  • the separated phosgene is recycled to the same phosgenation reaction in which the hydrogen chloride-containing gas used according to the invention was formed.
  • the resulting hydrogen chloride-containing gas has a CO content which is in particular less than 1% by volume, more preferably less than 0.5% by volume.
  • the hydrogen chloride-containing gas is preferably subjected to the catalytic oxidation with oxygen in a conventional manner after the separation of the phosgene. This process is commonly referred to as the "Deacon process.” Reference may be made to the relevant prior art for the performance of HCl oxidation.
  • ⁇ pressure range from 1 to about 100 bar
  • the phosgene can be removed from the gas after HCl oxidation.
  • FIG. 2 illustrates a conventional process in which the CO formed in the phosgene synthesis is first separated by condensation of the phosgene and converted into phosgene in a subsequent combination with CI 2 .
  • the disadvantage of this process is that the entire phosgene is condensed, which is very energy-consuming.
  • FIG. 1 shows schematically the method according to the invention.
  • the HC1 / CO feed gas which preferably originates from a phosgenation or isocyanate preparation process, is first preferably reacted on an activated carbon catalyst using chlorine to form a HCl / phosgene gas mixture.
  • the separation of the phosgene which is preferably fed again into the phosgenation or isocyanate production process takes place.
  • the reaction of the remaining HCl gas in the HCl oxidation according to the Deacon process expediently takes place in a manner known per se, the process gas optionally being able to be returned to the Deacon reactor after removal of the chlorine.
  • FIG. 3 shows the incorporation of the process according to the invention in the course of an isocyanate synthesis.
  • the CO used in excess in the phosgene synthesis does not need to be separated initially, as a result of which an energy-consuming condensation of the phosgene is eliminated. Also no Nachverier is needed.
  • the CO-containing phosgene will be so in the
  • Phosgenation reaction can be attributed.
  • the CO-depleted HCl gas which preferably has less than about 0.5% CO by volume, is then preferably added to the deaconate.
  • Process ie, subjected to the catalytic oxidation of hydrogen chloride with oxygen to form Ch.
  • the formed Cl 2 is separated and recycled to the phosgene synthesis process. If appropriate, the residual gas can be recirculated to the Deacon process.
  • the isocyanate synthesis is carried out in a conventional manner.
  • Phosgene obtained by the process according to the invention can then be used according to the processes known from the prior art for the preparation of TDI or MDI from TDA or MDA.
  • the hydrogen chloride which is formed in turn during the phosgenation of TDA and MDA can then be converted to chlorine by the processes described.
  • the carbon monoxide content is significantly reduced in the HCl stream, whereby a deactivation of the Deacon catalyst is slowed down at the next stage by uncontrolled temperature increase.
  • the precious carbon monoxide will be reused by conversion to phosgene.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Environmental & Geological Engineering (AREA)
  • Biomedical Technology (AREA)
  • Health & Medical Sciences (AREA)
  • Analytical Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Carbon And Carbon Compounds (AREA)
  • Separation By Low-Temperature Treatments (AREA)

Abstract

La présente invention concerne un procédé pour séparer du monoxyde de carbone d'un gaz contenant du chlorure d'hydrogène, ce procédé consistant à faire réagir le monoxyde de carbone avec du chlore pour former du phosgène, puis à séparer le phosgène du gaz contenant du chlorure d'hydrogène. Le gaz contenant du chlorure d'hydrogène utilisé provient de préférence de la réaction de phosgénation ou de la réaction de formation d'isocyanates.
EP07725286A 2006-05-23 2007-05-16 Procédé pour séparer du monoxyde de carbone d'un gaz contenant du chlorure d'hydrogène Withdrawn EP2027066A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102006024542A DE102006024542A1 (de) 2006-05-23 2006-05-23 Verfahren zur Abtrennung von Kohlenmonoxid aus einem chlorwasserstoffhaltigen Gas
PCT/EP2007/004370 WO2007134773A1 (fr) 2006-05-23 2007-05-16 Procédé pour séparer du monoxyde de carbone d'un gaz contenant du chlorure d'hydrogène

Publications (1)

Publication Number Publication Date
EP2027066A1 true EP2027066A1 (fr) 2009-02-25

Family

ID=38320935

Family Applications (1)

Application Number Title Priority Date Filing Date
EP07725286A Withdrawn EP2027066A1 (fr) 2006-05-23 2007-05-16 Procédé pour séparer du monoxyde de carbone d'un gaz contenant du chlorure d'hydrogène

Country Status (9)

Country Link
US (1) US7612234B2 (fr)
EP (1) EP2027066A1 (fr)
JP (1) JP2009537450A (fr)
KR (1) KR20090009897A (fr)
CN (1) CN101448739A (fr)
DE (1) DE102006024542A1 (fr)
RU (1) RU2008150594A (fr)
TW (1) TW200811042A (fr)
WO (1) WO2007134773A1 (fr)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2965490B1 (fr) 2010-09-30 2013-01-11 Aet Group Dispositif et procede pour la phosgenation en continu
CN102060295B (zh) * 2010-11-06 2012-08-08 青岛科技大学 一种低氯化氢含量的高纯光气的生产工艺
WO2012130788A1 (fr) * 2011-03-31 2012-10-04 Basf Se Procédé de production d'isocyanates
EP2559658A1 (fr) * 2011-08-19 2013-02-20 Huntsman International LLC Procédé de séparation de chlorure de carbonyle et de chlorure d'hydrogène d'un flux fluide comportant du chlorure de carbonyle et du chlorure d'hydrogène
EP2559659A1 (fr) * 2011-08-19 2013-02-20 Huntsman International Llc Procédé de séparation de gaz de chlorure d'hydrogène d'un mélange de chlorure de carbonyle et de chlorure d'hydrogène
CN104492237A (zh) * 2014-12-28 2015-04-08 甘肃银光聚银化工有限公司 一种光气合成尾气的回收方法
EP3421426A1 (fr) * 2017-06-29 2019-01-02 Covestro Deutschland AG Procédé à haute performance énergétique destiné à produire de la vapeur de phosgène
CN111111432B (zh) * 2019-12-31 2022-05-27 南京工大环境科技有限公司 一种光气化反应尾气的处理方法

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Also Published As

Publication number Publication date
JP2009537450A (ja) 2009-10-29
US7612234B2 (en) 2009-11-03
RU2008150594A (ru) 2010-06-27
WO2007134773A1 (fr) 2007-11-29
DE102006024542A1 (de) 2007-11-29
TW200811042A (en) 2008-03-01
KR20090009897A (ko) 2009-01-23
US20070276158A1 (en) 2007-11-29
WO2007134773A8 (fr) 2008-12-11
CN101448739A (zh) 2009-06-03

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