CA1043357A - Synthese catalysee de nitriles insatures - Google Patents

Synthese catalysee de nitriles insatures

Info

Publication number: CA1043357A
Authority: CA; Canada
Prior art keywords: catalyst; catalysts; mixture; methacrylonitrile; nitrate
Prior art date: 1973-06-04
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

CA201,363A

Other languages

English (en)

Other versions

CA201363S (en

Inventor

Robert K. Grasselli

Dev D. Suresh

Arthur F. Miller

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.)

Standard Oil Co

Original Assignee

Standard Oil Co

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.)

1973-06-04

Filing date

1974-05-31

Publication date

1978-11-28

1974-05-31 Application filed by Standard Oil Co filed Critical Standard Oil Co

1978-11-28 Application granted granted Critical

1978-11-28 Publication of CA1043357A publication Critical patent/CA1043357A/fr

Status Expired legal-status Critical Current

Links

239000003054 catalyst Substances 0.000 title claims abstract description 72
238000004519 manufacturing process Methods 0.000 title abstract description 5
150000002825 nitriles Chemical class 0.000 title abstract description 3
229910052751 metal Inorganic materials 0.000 title abstract 2
239000002184 metal Substances 0.000 title abstract 2
150000002739 metals Chemical class 0.000 title abstract 2
239000000203 mixture Substances 0.000 claims abstract description 17
GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 claims abstract description 14
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims abstract description 10
229910052790 beryllium Inorganic materials 0.000 claims abstract description 6
229910052804 chromium Inorganic materials 0.000 claims abstract description 6
239000011651 chromium Substances 0.000 claims abstract description 6
229910052759 nickel Inorganic materials 0.000 claims abstract description 6
229910052709 silver Inorganic materials 0.000 claims abstract description 6
229910052721 tungsten Inorganic materials 0.000 claims abstract description 6
229910052796 boron Inorganic materials 0.000 claims abstract description 5
229910052802 copper Inorganic materials 0.000 claims abstract description 5
239000010949 copper Substances 0.000 claims abstract description 5
229910052733 gallium Inorganic materials 0.000 claims abstract description 5
229910052732 germanium Inorganic materials 0.000 claims abstract description 5
229910052738 indium Inorganic materials 0.000 claims abstract description 5
WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims abstract description 5
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims abstract description 4
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims abstract description 4
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims abstract description 4
ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 claims abstract description 4
229910052793 cadmium Inorganic materials 0.000 claims abstract description 4
229910052791 calcium Inorganic materials 0.000 claims abstract description 4
GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims abstract description 4
229910052749 magnesium Inorganic materials 0.000 claims abstract description 4
239000004332 silver Substances 0.000 claims abstract description 4
239000010936 titanium Substances 0.000 claims abstract description 4
229910052719 titanium Inorganic materials 0.000 claims abstract description 4
239000010937 tungsten Substances 0.000 claims abstract description 4
229910052725 zinc Inorganic materials 0.000 claims abstract description 4
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims abstract description 3
GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 claims abstract description 3
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims abstract description 3
APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 claims abstract description 3
229910052707 ruthenium Inorganic materials 0.000 claims abstract description 3
238000006243 chemical reaction Methods 0.000 claims description 32
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 14
238000000034 method Methods 0.000 claims description 14
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 9
VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 9
229910021529 ammonia Inorganic materials 0.000 claims description 6
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 6
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 6
229910052783 alkali metal Inorganic materials 0.000 claims description 4
150000001340 alkali metals Chemical class 0.000 claims description 4
238000002360 preparation method Methods 0.000 claims description 4
229910052698 phosphorus Inorganic materials 0.000 claims description 3
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
150000001342 alkaline earth metals Chemical class 0.000 claims description 2
229910052785 arsenic Inorganic materials 0.000 claims description 2
229910001882 dioxygen Inorganic materials 0.000 claims description 2
229910052758 niobium Inorganic materials 0.000 claims description 2
229910052761 rare earth metal Inorganic materials 0.000 claims description 2
150000002910 rare earth metals Chemical class 0.000 claims description 2
239000010944 silver (metal) Substances 0.000 claims description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 abstract description 5
ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 abstract description 4
229910017052 cobalt Inorganic materials 0.000 abstract description 4
239000010941 cobalt Substances 0.000 abstract description 4
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 abstract description 4
229910052750 molybdenum Inorganic materials 0.000 abstract description 4
239000011733 molybdenum Substances 0.000 abstract description 4
229910052718 tin Inorganic materials 0.000 abstract description 4
239000011135 tin Substances 0.000 abstract description 4
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 abstract description 3
239000011575 calcium Substances 0.000 abstract description 3
239000011777 magnesium Substances 0.000 abstract description 3
239000011701 zinc Substances 0.000 abstract description 3
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 abstract description 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 abstract description 2
BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 abstract description 2
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract description 2
229910052797 bismuth Inorganic materials 0.000 abstract description 2
JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 abstract description 2
BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 abstract description 2
229910052742 iron Inorganic materials 0.000 abstract description 2
230000000052 comparative effect Effects 0.000 description 19
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 18
239000000243 solution Substances 0.000 description 18
239000002002 slurry Substances 0.000 description 15
239000002585 base Substances 0.000 description 13
VCJMYUPGQJHHFU-UHFFFAOYSA-N iron(3+);trinitrate Chemical compound [Fe+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O VCJMYUPGQJHHFU-UHFFFAOYSA-N 0.000 description 10
FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 9
239000000377 silicon dioxide Substances 0.000 description 8
150000001336 alkenes Chemical class 0.000 description 7
KBJMLQFLOWQJNF-UHFFFAOYSA-N nickel(ii) nitrate Chemical compound [Ni+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O KBJMLQFLOWQJNF-UHFFFAOYSA-N 0.000 description 7
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 7
239000000376 reactant Substances 0.000 description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
QGAVSDVURUSLQK-UHFFFAOYSA-N ammonium heptamolybdate Chemical compound N.N.N.N.N.N.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.[Mo].[Mo].[Mo].[Mo].[Mo].[Mo].[Mo] QGAVSDVURUSLQK-UHFFFAOYSA-N 0.000 description 6
UFMZWBIQTDUYBN-UHFFFAOYSA-N cobalt dinitrate Chemical compound [Co+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O UFMZWBIQTDUYBN-UHFFFAOYSA-N 0.000 description 5
229910001981 cobalt nitrate Inorganic materials 0.000 description 5
229910052681 coesite Inorganic materials 0.000 description 5
229910052906 cristobalite Inorganic materials 0.000 description 5
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 5
235000012239 silicon dioxide Nutrition 0.000 description 5
229910052682 stishovite Inorganic materials 0.000 description 5
229910052905 tridymite Inorganic materials 0.000 description 5
RXPAJWPEYBDXOG-UHFFFAOYSA-N hydron;methyl 4-methoxypyridine-2-carboxylate;chloride Chemical compound Cl.COC(=O)C1=CC(OC)=CC=N1 RXPAJWPEYBDXOG-UHFFFAOYSA-N 0.000 description 4
229910001960 metal nitrate Inorganic materials 0.000 description 4
239000004323 potassium nitrate Substances 0.000 description 4
235000010333 potassium nitrate Nutrition 0.000 description 4
229910000147 aluminium phosphate Inorganic materials 0.000 description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
229910052760 oxygen Inorganic materials 0.000 description 3
239000001301 oxygen Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
229910002012 Aerosil® Inorganic materials 0.000 description 2
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
150000001450 anions Chemical class 0.000 description 2
CHPZKNULDCNCBW-UHFFFAOYSA-N gallium nitrate Chemical compound [Ga+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O CHPZKNULDCNCBW-UHFFFAOYSA-N 0.000 description 2
YBMRDBCBODYGJE-UHFFFAOYSA-N germanium dioxide Chemical compound O=[Ge]=O YBMRDBCBODYGJE-UHFFFAOYSA-N 0.000 description 2
239000007787 solid Substances 0.000 description 2
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
239000004327 boric acid Substances 0.000 description 1
YZYDPPZYDIRSJT-UHFFFAOYSA-K boron phosphate Chemical compound [B+3].[O-]P([O-])([O-])=O YZYDPPZYDIRSJT-UHFFFAOYSA-K 0.000 description 1
229910000149 boron phosphate Inorganic materials 0.000 description 1
239000012876 carrier material Substances 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
PPNKDDZCLDMRHS-UHFFFAOYSA-N dinitrooxybismuthanyl nitrate Chemical compound [Bi+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O PPNKDDZCLDMRHS-UHFFFAOYSA-N 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000012530 fluid Substances 0.000 description 1
229940044658 gallium nitrate Drugs 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
PSCMQHVBLHHWTO-UHFFFAOYSA-K indium(iii) chloride Chemical compound Cl[In](Cl)Cl PSCMQHVBLHHWTO-UHFFFAOYSA-K 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
239000011949 solid catalyst Substances 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
229910052716 thallium Inorganic materials 0.000 description 1
BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
230000035899 viability Effects 0.000 description 1

Landscapes

Catalysts (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA201,363A 1973-06-04 1974-05-31 Synthese catalysee de nitriles insatures Expired CA1043357A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US36704273A	1973-06-04	1973-06-04
US38052773A	1973-07-19	1973-07-19

Publications (1)

Publication Number	Publication Date
CA1043357A true CA1043357A (fr)	1978-11-28

Family

ID=27003650

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA201,363A Expired CA1043357A (fr)	1973-06-04	1974-05-31	Synthese catalysee de nitriles insatures

Country Status (2)

Country	Link
CA (1)	CA1043357A (fr)
PH (1)	PH11704A (fr)

1974
- 1974-05-31 CA CA201,363A patent/CA1043357A/fr not_active Expired
- 1974-05-31 PH PH15883A patent/PH11704A/en unknown

Also Published As

Publication number	Publication date
PH11704A (en)	1978-05-24

Publication	Publication Date	Title
US3956181A (en)	1976-05-11	Oxidation catalyst
US4040978A (en)	1977-08-09	Production of (amm)oxidation catalyst
US4162234A (en)	1979-07-24	Oxidation catalysts
US5132269A (en)	1992-07-21	Iron-antimony-molybdenum-containing oxide catalyst composition and process for preparing the same
US4467113A (en)	1984-08-21	Process for producing methacrylic acid
US5144090A (en)	1992-09-01	Method for preparing acrolein or methacrolein
JPS6242654B2 (fr)	1987-09-09
US5840648A (en)	1998-11-24	Catalyst for the manufacture of acrylonitrile and hydrogen cyanide
US4414133A (en)	1983-11-08	Catalytic composition
US4766232A (en)	1988-08-23	Production of unsaturated nitriles using catalysts containing boron, gallium or indium
US4168246A (en)	1979-09-18	Production of (amm)oxidation catalyst
JPS6214535B2 (fr)	1987-04-02
US5139988A (en)	1992-08-18	Iron-antimony-containing metal oxide catalyst composition and process for producing the same
US4377534A (en)	1983-03-22	Production of unsaturated nitriles
US4745217A (en)	1988-05-17	Process for producing methacrylic acid
US4190556A (en)	1980-02-26	Production of unsaturated nitriles using catalysts promoted with various metals
US4139552A (en)	1979-02-13	Production of unsaturated nitriles
US5470815A (en)	1995-11-28	Multicomponent oxide catalyst
NO143740B (no)	1980-12-29	Fremgangsmaate for fremstilling av akrylnitril eller metakrylnitril.
US4495109A (en)	1985-01-22	Production of unsaturated nitriles using catalysts promoted with various metals
US4246421A (en)	1981-01-20	Oxydehydrogenation process for alkylaromatics
US4174354A (en)	1979-11-13	Oxidative dehydrogenation using chromium-containing catalysts
US3907859A (en)	1975-09-23	Coproduction of acrylonitrile and acrylic acid
US3993680A (en)	1976-11-23	Ammoxidation using chromium-containing catalysts
JPS6230177B2 (fr)	1987-07-01