DE2725041C3 - Katalysator und Verfahren zur Herstellung von ungesättigten Nitrilen - Google Patents

Katalysator und Verfahren zur Herstellung von ungesättigten Nitrilen

Info

Publication number: DE2725041C3
Authority: DE; Germany
Prior art keywords: catalyst; propylene; production; ammoxidation; oxides
Prior art date: 1976-06-04
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.): Expired

Application number

DE2725041A

Other languages

German (de)

English (en)

Other versions

DE2725041B2 (de

DE2725041A1 (de

Inventor

Jacques Marion

Christian Pralus

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.)

PRODUITS CHIMIQUES UGINE KUHLMANN PARIS

Original Assignee

PRODUITS CHIMIQUES UGINE KUHLMANN PARIS

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.)

1976-06-04

Filing date

1977-06-03

Publication date

1979-05-03

1977-06-03 Application filed by PRODUITS CHIMIQUES UGINE KUHLMANN PARIS filed Critical PRODUITS CHIMIQUES UGINE KUHLMANN PARIS

1977-12-08 Publication of DE2725041A1 publication Critical patent/DE2725041A1/de

1978-08-24 Publication of DE2725041B2 publication Critical patent/DE2725041B2/de

1979-05-03 Application granted granted Critical

1979-05-03 Publication of DE2725041C3 publication Critical patent/DE2725041C3/de

Status Expired legal-status Critical Current

Links

239000003054 catalyst Substances 0.000 title claims description 28
238000004519 manufacturing process Methods 0.000 title claims description 10
150000002825 nitriles Chemical class 0.000 title claims description 8
238000000034 method Methods 0.000 title description 3
150000001336 alkenes Chemical class 0.000 claims description 12
239000011135 tin Substances 0.000 claims description 12
239000010949 copper Substances 0.000 claims description 11
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 8
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 6
WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims description 6
238000010438 heat treatment Methods 0.000 claims description 6
150000001875 compounds Chemical class 0.000 claims description 4
229910000410 antimony oxide Inorganic materials 0.000 claims description 3
230000001590 oxidative effect Effects 0.000 claims description 3
238000002156 mixing Methods 0.000 claims description 2
238000001556 precipitation Methods 0.000 claims description 2
150000003839 salts Chemical class 0.000 claims description 2
238000005979 thermal decomposition reaction Methods 0.000 claims description 2
229910001887 tin oxide Inorganic materials 0.000 claims description 2
229910001930 tungsten oxide Inorganic materials 0.000 claims description 2
229910000431 copper oxide Inorganic materials 0.000 claims 1
QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 claims 1
229910052845 zircon Inorganic materials 0.000 claims 1
GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 claims 1
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 22
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 22
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 14
239000000203 mixture Substances 0.000 description 13
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 8
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 8
LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 8
229910021529 ammonia Inorganic materials 0.000 description 7
238000006243 chemical reaction Methods 0.000 description 6
238000003756 stirring Methods 0.000 description 6
229910052718 tin Inorganic materials 0.000 description 6
229910052802 copper Inorganic materials 0.000 description 5
229910052760 oxygen Inorganic materials 0.000 description 5
229910052721 tungsten Inorganic materials 0.000 description 5
QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 4
229910052787 antimony Inorganic materials 0.000 description 4
ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
230000003197 catalytic effect Effects 0.000 description 4
239000007789 gas Substances 0.000 description 4
239000007788 liquid Substances 0.000 description 4
239000001301 oxygen Substances 0.000 description 4
239000000843 powder Substances 0.000 description 4
WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 4
239000010937 tungsten Substances 0.000 description 4
229910052726 zirconium Inorganic materials 0.000 description 4
238000001914 filtration Methods 0.000 description 3
VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
238000001816 cooling Methods 0.000 description 2
XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 description 2
XAYGUHUYDMLJJV-UHFFFAOYSA-Z decaazanium;dioxido(dioxo)tungsten;hydron;trioxotungsten Chemical compound [H+].[H+].[NH4+].[NH4+].[NH4+].[NH4+].[NH4+].[NH4+].[NH4+].[NH4+].[NH4+].[NH4+].O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.[O-][W]([O-])(=O)=O.[O-][W]([O-])(=O)=O.[O-][W]([O-])(=O)=O.[O-][W]([O-])(=O)=O.[O-][W]([O-])(=O)=O.[O-][W]([O-])(=O)=O XAYGUHUYDMLJJV-UHFFFAOYSA-Z 0.000 description 2
229910017604 nitric acid Inorganic materials 0.000 description 2
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
239000000047 product Substances 0.000 description 2
239000000376 reactant Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
238000007669 thermal treatment Methods 0.000 description 2
238000005406 washing Methods 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
GLAKNHGQBRSLIO-UHFFFAOYSA-N azane;prop-1-ene Chemical compound N.CC=C GLAKNHGQBRSLIO-UHFFFAOYSA-N 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
238000010908 decantation Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
-1 ethane and propane Natural products 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000011521 glass Substances 0.000 description 1
229910002804 graphite Inorganic materials 0.000 description 1
239000010439 graphite Substances 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
239000011872 intimate mixture Substances 0.000 description 1
238000004898 kneading Methods 0.000 description 1
238000011031 large-scale manufacturing process Methods 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
229910044991 metal oxide Inorganic materials 0.000 description 1
150000004706 metal oxides Chemical class 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
VTRUBDSFZJNXHI-UHFFFAOYSA-N oxoantimony Chemical compound [Sb]=O VTRUBDSFZJNXHI-UHFFFAOYSA-N 0.000 description 1
VVRQVWSVLMGPRN-UHFFFAOYSA-N oxotungsten Chemical class [W]=O VVRQVWSVLMGPRN-UHFFFAOYSA-N 0.000 description 1
RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
239000001294 propane Substances 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
QHGNHLZPVBIIPX-UHFFFAOYSA-N tin(ii) oxide Chemical class [Sn]=O QHGNHLZPVBIIPX-UHFFFAOYSA-N 0.000 description 1
239000012808 vapor phase Substances 0.000 description 1
229910001928 zirconium oxide Inorganic materials 0.000 description 1

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
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/84—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/85—Chromium, molybdenum or tungsten
- 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

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)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Catalysts (AREA)

DE2725041A 1976-06-04 1977-06-03 Katalysator und Verfahren zur Herstellung von ungesättigten Nitrilen Expired DE2725041C3 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR7616926A FR2353523A1 (fr)	1976-06-04	1976-06-04	Catalyseurs et procede pour la fabrication de nitriles insatures

Publications (3)

Publication Number	Publication Date
DE2725041A1 DE2725041A1 (de)	1977-12-08
DE2725041B2 DE2725041B2 (de)	1978-08-24
DE2725041C3 true DE2725041C3 (de)	1979-05-03

Family

ID=9174000

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DE2725041A Expired DE2725041C3 (de)	1976-06-04	1977-06-03	Katalysator und Verfahren zur Herstellung von ungesättigten Nitrilen

Country Status (12)

Country	Link
JP (1)	JPS52148023A (pt)
BE (1)	BE855195A (pt)
BR (1)	BR7703566A (pt)
DE (1)	DE2725041C3 (pt)
ES (1)	ES459490A1 (pt)
FR (1)	FR2353523A1 (pt)
GB (1)	GB1551525A (pt)
IT (1)	IT1083409B (pt)
MX (1)	MX4062E (pt)
NL (1)	NL7706133A (pt)
SU (1)	SU692544A3 (pt)
TR (1)	TR19237A (pt)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS57134454A (en) *	1981-02-12	1982-08-19	Takeda Chem Ind Ltd	Preparation of unsaturated aliphatic dinitrile

1976
- 1976-06-04 FR FR7616926A patent/FR2353523A1/fr active Granted
1977
- 1977-04-26 MX MX77100555U patent/MX4062E/es unknown
- 1977-04-29 GB GB18079/77A patent/GB1551525A/en not_active Expired
- 1977-05-09 TR TR19237A patent/TR19237A/xx unknown
- 1977-05-23 JP JP5889277A patent/JPS52148023A/ja active Pending
- 1977-05-31 BE BE1008166A patent/BE855195A/xx unknown
- 1977-06-02 BR BR7703566A patent/BR7703566A/pt unknown
- 1977-06-03 SU SU772489901A patent/SU692544A3/ru active
- 1977-06-03 IT IT68294/77A patent/IT1083409B/it active
- 1977-06-03 ES ES459490A patent/ES459490A1/es not_active Expired
- 1977-06-03 DE DE2725041A patent/DE2725041C3/de not_active Expired
- 1977-06-03 NL NL7706133A patent/NL7706133A/xx not_active Application Discontinuation

Also Published As

Publication number	Publication date
IT1083409B (it)	1985-05-21
JPS52148023A (en)	1977-12-08
SU692544A3 (ru)	1979-10-15
ES459490A1 (es)	1978-08-16
NL7706133A (nl)	1977-12-06
GB1551525A (en)	1979-08-30
BR7703566A (pt)	1978-03-21
DE2725041B2 (de)	1978-08-24
BE855195A (fr)	1977-11-30
DE2725041A1 (de)	1977-12-08
FR2353523A1 (fr)	1977-12-30
MX4062E (es)	1981-11-30
FR2353523B1 (pt)	1979-07-13
TR19237A (tr)	1978-07-19

Publication	Publication Date	Title
DE69505336T2 (de)	1999-03-04	Verfahren zur Herstellung von Acrylsäure
DE69012450T2 (de)	1995-03-02	Verfahren zur Herstellung von Eisen-Phosphor und Antimon enthaltenden Metalloxid-Oxidationskatalysatoren.
DE2441109A1 (de)	1975-03-06	Verfahren zur katalytischen oxydation von tert.-butylalkohol in der dampfphase
DE1468669A1 (de)	1969-01-23	Katalytisches Verfahren zur Herstellung von Nitrilen
DE1197446B (de)	1965-07-29	Verfahren zur Herstellung von Acrylsaeurenitril durch Umsetzung von Propylen mit Ammoniak und Sauerstoff
DE2620554C3 (de)	1984-05-24	Verfahren zur Herstellung eines Kupfer-Nickel-Siliciumoxid-Katalysators und seine Verwendung
DE68907642T2 (de)	1993-11-04	Verfahren zur herstellung von cyanwasserstoff durch katalytische ammoxidierung in der gasphase von methanol.
DE68902042T2 (de)	1992-12-10	Vanadium und antimon enthaltender katalysator und katalysatorvorlaeufer.
DE2941341C2 (de)	1982-11-04	Verfahren zur Herstellung von Methacrolein
DE69119925T2 (de)	1996-11-28	Verfahren zur Herstellung von Katalysatoren für die Herstellung von Methakrylsäure
DE69622692T2 (de)	2003-04-03	Verfahren zur herstellung von ungesättigten nitrilen
DD231298A5 (de)	1985-12-24	Antimon enthaltende metalloxid-katalysatoren und verfahren zu deren herstellung
DE2527489C2 (de)	1986-11-13	Katalysator und dessen Verwendung zur Herstellung von Acrylnitril
DE2600802C3 (de)	1979-08-09	Verfahren zur Herstellung von Methacrylsäure durch Oxidation von Methacrolein
DE2725041C3 (de)	1979-05-03	Katalysator und Verfahren zur Herstellung von ungesättigten Nitrilen
DE2543520A1 (de)	1976-04-22	Katalysatorzusammensetzungen
DE2513320C3 (de)	1979-03-29	Katalysator zur Herstellung von ungesättigten Nitrilen
DE69221561T2 (de)	1998-02-26	Verfahren zur Ammoxydation von gesättigten Kohlenwasserstoffen
DE69309106T2 (de)	1997-10-16	Prozess zur herstellung von (meth)acrylnitril durch ammoxidation
DE2449387B2 (de)	1976-09-16	Verfahren zur herstellung eines oxydationskatalysators und dessen verwendung
DE2641846A1 (de)	1977-07-07	Uranoxid-antimonoxidverbindung sowie herstellung und verwendung derselben als katalysator
DE69718777T2 (de)	2003-06-26	Verfahren zur Herstellung von verbesserten Vanadium Antimonoxid Oxidierungs- und Ammoxidierungskatalysatoren
DE2720946A1 (de)	1977-12-01	Verfahren zur katalytischen herstellung von acrylnitril
DE2244264A1 (de)	1973-03-15	Herstellung von nitrilen durch ammoxydation von butadien
DE2706271C3 (de)	1979-04-26	Katalysator zur Herstellung von ungesättigten Nitrilen

Legal Events

Date	Code	Title
1978-01-26	OD	Request for examination
1979-05-03	C3	Grant after two publication steps (3rd publication)
1982-10-07	8339	Ceased/non-payment of the annual fee