EP1404647A1 - Procede de production de nitriles insatures a partir d'alcanes - Google Patents

Procede de production de nitriles insatures a partir d'alcanes

Info

Publication number
EP1404647A1
EP1404647A1 EP02762301A EP02762301A EP1404647A1 EP 1404647 A1 EP1404647 A1 EP 1404647A1 EP 02762301 A EP02762301 A EP 02762301A EP 02762301 A EP02762301 A EP 02762301A EP 1404647 A1 EP1404647 A1 EP 1404647A1
Authority
EP
European Patent Office
Prior art keywords
alkane
alkene
gas stream
ammonia
dehydrogenation
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Withdrawn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
EP02762301A
Other languages
German (de)
English (en)
Inventor
Frieder Borgmeier
Frank Rosowski
Götz-Peter SCHINDLER
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.)
BASF SE
Original Assignee
BASF SE
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
Priority claimed from DE10131297A external-priority patent/DE10131297A1/de
Priority claimed from DE10211275A external-priority patent/DE10211275A1/de
Priority claimed from DE2002117844 external-priority patent/DE10217844A1/de
Application filed by BASF SE filed Critical BASF SE
Publication of EP1404647A1 publication Critical patent/EP1404647A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C253/00—Preparation of carboxylic acid nitriles
    • C07C253/24—Preparation of carboxylic acid nitriles by ammoxidation of hydrocarbons or substituted hydrocarbons
    • C07C253/26—Preparation of carboxylic acid nitriles by ammoxidation of hydrocarbons or substituted hydrocarbons containing carbon-to-carbon multiple bonds, e.g. unsaturated aldehydes
    • 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
    • B01J27/186—Phosphorus; Compounds thereof with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • B01J27/195—Phosphorus; Compounds thereof with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium with vanadium, niobium or tantalum
    • B01J27/198—Vanadium
    • B01J27/199—Vanadium with chromium, molybdenum, tungsten or polonium
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
    • C07C45/33—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
    • C07C45/33—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties
    • C07C45/34—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties in unsaturated compounds
    • C07C45/35—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties in unsaturated compounds in propene or isobutene
    • 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
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts

Definitions

  • the dehydrogenation temperature is generally 400 to 1100 ° C.
  • the pressure in the last catalyst bed of the tray reactor is generally 0.2 to 5 bar, preferably 1 to 3 bar.
  • the load (GHSV) is generally 500 to 2000 h "1 , in high-load operation
  • 1 1 also up to 100,000 h “ , preferably 4000 to 16,000 h " , based on the alkane to be dehydrogenated.
  • Suitable absorbents are comparatively non-polar organic solvents, for example a iphatician Cg to Cig alkenes, or aromatic hydrocarbons such as the middle oil fractions from paraffin distillation, or ethers with bulky groups, or mixtures of these solvents, these being a polar solvent such as 1,2-dimethylphthalate can be added.
  • a iphatician Cg to Cig alkenes or aromatic hydrocarbons such as the middle oil fractions from paraffin distillation, or ethers with bulky groups, or mixtures of these solvents, these being a polar solvent such as 1,2-dimethylphthalate can be added.
  • a feed gas stream B is obtained which contains the alkane and the alkene and is essentially freed from the other gas components.
  • the feed gas stream B contains the stripping gas in addition to the alkane and the alkene.
  • an oxygen-containing gas is used as the stripping gas in the amounts in which it is required in the subsequent ammoxidation.
  • ammonia is separated off separately by bringing the hot product gas stream C from the ammoxidation into contact with aqueous sulfuric acid in a quench tower and thus washing ammonia out of the product gas stream C as ammonium sulfate.
  • An aqueous ammonium sulfate solution is obtained, which can contain dissolved unsaturated nitrile and by-products of ammoxidation. These can be steamed in a downstream steam stripper are stripped out of the aqueous ammonium sulfate solution and sent for further distillative workup.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Procédé de production de nitriles insaturés à partir des alcanes correspondants, qui consiste (a) à introduire un alcane dans une zone de déshydrogénation et à déshydrogéner l'alcane par catalyse pour obtenir l'alcène correspondant, un flux gazeux A étant obtenu qui contient l'alcène, de l'alcane n'ayant pas réagi et éventuellement un ou plusieurs autres constituants gazeux, choisis dans le groupe constitué par la vapeur d'eau, l'hydrogène, des oxydes de carbone, des hydrocarbures à point d'ébullition plus bas que celui de l'alcane et de l'alcène (à point d'ébullition bas), l'azote et des gaz nobles, (b) à séparer au moins partiellement les autres constituants gazeux du flux gazeux A, ce qui permet d'obtenir un flux gazeux d'alimentation B qui contient l'alcane et l'alcène, (c) à introduire le flux gazeux d'alimentation B, de l'ammoniac, du gaz contenant de l'oxygène et éventuellement de la vapeur d'eau dans une zone d'oxydation et à ammoxyder par catalyse l'alcène pour obtenir le nitrile insaturé correspondant, un flux gazeux C étant obtenu qui contient le nitrile insaturé, des sous-produits de l'ammoxydation, de l'alcane et de l'alcène n'ayant pas réagi et éventuellement un ou plusieurs constituants gazeux choisis dans le groupe constitué par la vapeur d'eau, l'oxygène, des oxydes de carbone, l'ammoniac, l'azote et des gaz nobles, (d) éventuellement à séparer l'ammoniac du flux gazeux C, ce qui permet d'obtenir un flux gazeux D appauvri en ammoniac, (e) à séparer le nitrile insaturé et les sous-produits de l'ammoxydation du flux gazeux C ou D par absorption dans un milieu d'absorption aqueux, un flux de gaz E étant obtenu qui contient l'alcane et l'alcène n'ayant pas réagi et éventuellement un ou plusieurs autres constituants gazeux choisis dans le groupe constitué par l'oxygène, des oxydes de carbone, l'ammoniac, l'azote et des gaz nobles, et un flux aqueux étant également obtenu qui contient le nitrile et les sous-produits, et à récupérer le nitrile insaturé du flux aqueux et (f) à renvoyer le flux gazeux E dans la zone de déshydrogénation.
EP02762301A 2001-06-29 2002-06-25 Procede de production de nitriles insatures a partir d'alcanes Withdrawn EP1404647A1 (fr)

Applications Claiming Priority (7)

Application Number Priority Date Filing Date Title
DE10131297 2001-06-29
DE10131297A DE10131297A1 (de) 2001-06-29 2001-06-29 Verfahren zur Herstellung von partiellen Oxidationsprodukten und/oder partiellen Ammoxidationsprodukten wenigstens eines olefinischen Kohlenwasserstoffs
DE10211275A DE10211275A1 (de) 2002-03-13 2002-03-13 Verfahren der kontinuierlichen heterogen katalysierten partiellen Dehydrierung
DE10211275 2002-03-13
DE2002117844 DE10217844A1 (de) 2002-04-22 2002-04-22 Verfahren zur Herstellung von ungesättigten Nitrilen aus Alkanen
DE10217844 2002-04-22
PCT/EP2002/007024 WO2003002520A1 (fr) 2001-06-29 2002-06-25 Procede de production de nitriles insatures a partir d'alcanes

Publications (1)

Publication Number Publication Date
EP1404647A1 true EP1404647A1 (fr) 2004-04-07

Family

ID=27214489

Family Applications (1)

Application Number Title Priority Date Filing Date
EP02762301A Withdrawn EP1404647A1 (fr) 2001-06-29 2002-06-25 Procede de production de nitriles insatures a partir d'alcanes

Country Status (7)

Country Link
US (1) US7271279B2 (fr)
EP (1) EP1404647A1 (fr)
JP (1) JP2004532283A (fr)
KR (1) KR20040034619A (fr)
CN (1) CN1229338C (fr)
SA (1) SA02230243B1 (fr)
WO (1) WO2003002520A1 (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10217845A1 (de) * 2002-04-22 2003-11-06 Basf Ag Verfahren zur Herstellung von ungesättigten Nitrilen
WO2005113123A1 (fr) * 2004-05-07 2005-12-01 Basf Aktiengesellschaft Procede de remplissage structure de tubes de contact d'un faisceau de tubes de contact
US7601866B2 (en) 2005-03-01 2009-10-13 Basf Aktiengesellschaft Process for removing methacrolein from liquid phase comprising acrylic acid as a main constituent and target product, and methacrolein as a secondary component
DE102006000996A1 (de) 2006-01-05 2007-07-12 Basf Ag Verfahren der heterogen katalysierten Gasphasen-Partialoxidation wenigstens einer organischen Ausgangsverbindung
DE102008044946B4 (de) * 2008-08-29 2022-06-15 Evonik Superabsorber Gmbh Einsatz von Schaumkörpern in Oxidations-Reaktoren zur Herstellung ungesättigter Carbonsäuren

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4609502A (en) 1985-02-14 1986-09-02 The Halcon Sd Group, Inc. Process for preparing unsaturated nitriles from alkanes
US4849537A (en) 1988-02-09 1989-07-18 The Boc Group, Inc. Process for the production of nitriles
US4849538A (en) 1988-03-23 1989-07-18 The Boc Group, Inc. Process for the production of nitriles
US4870201A (en) * 1988-12-08 1989-09-26 The Boc Group, Inc. Process for the production of nitriles
US5008414A (en) 1988-12-08 1991-04-16 The Boc Group, Inc. Process for the production of oxides
US4943650A (en) * 1989-01-30 1990-07-24 The Boc Group, Inc. Process for the production of nitriles
US5268497A (en) 1992-02-24 1993-12-07 The Boc Group, Inc. Process for the production of nitriles

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO03002520A1 *

Also Published As

Publication number Publication date
CN1522243A (zh) 2004-08-18
JP2004532283A (ja) 2004-10-21
KR20040034619A (ko) 2004-04-28
WO2003002520A1 (fr) 2003-01-09
SA02230243B1 (ar) 2008-09-07
CN1229338C (zh) 2005-11-30
US7271279B2 (en) 2007-09-18
US20040199000A1 (en) 2004-10-07

Similar Documents

Publication Publication Date Title
EP1453778B1 (fr) Procede pour produire du 1,2-dichloroethane
EP1682468B1 (fr) Procede de fabrication de 1-butene
EP1831134B1 (fr) Procede de production de butadiene a partir de n-butane
EP1523462B1 (fr) Procede de production de butadiene a partir de n-butane
EP1708977B1 (fr) Procede de production de butadiene et 1-butene
EP1708978B1 (fr) Procede de production de butadiene
EP1833776A1 (fr) Procede de production de propene a partir de propane
EP1824803B1 (fr) Procede de fabrication de propene a partir de propane
EP1858831A2 (fr) Procede de production de propene a partir de propane
EP1836146B1 (fr) Procede de production de propene a partir de propane
EP1701928B1 (fr) Procede de production de butadiene
DE102005000798A1 (de) Verfahren zur Herstellung von Propen aus Propan
EP1404647A1 (fr) Procede de production de nitriles insatures a partir d'alcanes
EP1678105B1 (fr) Procede de fabrication du 1-butene
DE10217844A1 (de) Verfahren zur Herstellung von ungesättigten Nitrilen aus Alkanen
DE102005012291A1 (de) Verfahren zur Herstellung von Propen aus Propan
WO2003089407A1 (fr) Procede de preparation de nitriles insatures
WO2003029171A1 (fr) Procede de production de composes aromatiques alkyles

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 20040129

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AT BE CH CY DE DK ES FI FR GB GR IE IT LI LU MC NL PT SE TR

AX Request for extension of the european patent

Extension state: AL LT LV MK RO SI

RAP1 Party data changed (applicant data changed or rights of an application transferred)

Owner name: BASF SE

17Q First examination report despatched

Effective date: 20090129

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN

18D Application deemed to be withdrawn

Effective date: 20090811