DE2124472A1 - Verfahren zur Herstellung von ungesättigten Nitrilen - Google Patents
Verfahren zur Herstellung von ungesättigten NitrilenInfo
- Publication number
- DE2124472A1 DE2124472A1 DE19712124472 DE2124472A DE2124472A1 DE 2124472 A1 DE2124472 A1 DE 2124472A1 DE 19712124472 DE19712124472 DE 19712124472 DE 2124472 A DE2124472 A DE 2124472A DE 2124472 A1 DE2124472 A1 DE 2124472A1
- Authority
- DE
- Germany
- Prior art keywords
- zone
- ammonia
- reaction
- catalyst
- olefin
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 29
- 150000002825 nitriles Chemical class 0.000 title claims description 12
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 78
- 239000003054 catalyst Substances 0.000 claims description 56
- 150000001336 alkenes Chemical class 0.000 claims description 44
- 238000006243 chemical reaction Methods 0.000 claims description 42
- 229910021529 ammonia Inorganic materials 0.000 claims description 40
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 36
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 29
- 239000001301 oxygen Substances 0.000 claims description 29
- 229910052760 oxygen Inorganic materials 0.000 claims description 29
- 230000008929 regeneration Effects 0.000 claims description 24
- 238000011069 regeneration method Methods 0.000 claims description 24
- 239000002245 particle Substances 0.000 claims description 10
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 10
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 10
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 9
- 238000007254 oxidation reaction Methods 0.000 claims description 7
- 239000007795 chemical reaction product Substances 0.000 claims description 6
- 230000003647 oxidation Effects 0.000 claims description 6
- 150000005673 monoalkenes Chemical class 0.000 claims description 2
- 239000000047 product Substances 0.000 description 7
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 6
- 229910052787 antimony Inorganic materials 0.000 description 6
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 6
- 229910001882 dioxygen Inorganic materials 0.000 description 6
- 230000004048 modification Effects 0.000 description 5
- 238000012986 modification Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 4
- 229910052797 bismuth Inorganic materials 0.000 description 4
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 229910052770 Uranium Inorganic materials 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
- 239000010419 fine particle Substances 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 1
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical compound CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 1
- ZSLUVFAKFWKJRC-IGMARMGPSA-N 232Th Chemical compound [232Th] ZSLUVFAKFWKJRC-IGMARMGPSA-N 0.000 description 1
- YHQXBTXEYZIYOV-UHFFFAOYSA-N 3-methylbut-1-ene Chemical compound CC(C)C=C YHQXBTXEYZIYOV-UHFFFAOYSA-N 0.000 description 1
- UZPWKTCMUADILM-UHFFFAOYSA-N 3-methylcyclohexene Chemical compound CC1CCCC=C1 UZPWKTCMUADILM-UHFFFAOYSA-N 0.000 description 1
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- 241000282346 Meles meles Species 0.000 description 1
- 229910052776 Thorium Inorganic materials 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 150000001462 antimony Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- -1 cyclic Olefins Chemical class 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical group [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
- VLAPMBHFAWRUQP-UHFFFAOYSA-L molybdic acid Chemical class O[Mo](O)(=O)=O VLAPMBHFAWRUQP-UHFFFAOYSA-L 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 1
- QMMOXUPEWRXHJS-UHFFFAOYSA-N pentene-2 Natural products CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 description 1
- JTJMJGYZQZDUJJ-UHFFFAOYSA-N phencyclidine Chemical class C1CCCCN1C1(C=2C=CC=CC=2)CCCCC1 JTJMJGYZQZDUJJ-UHFFFAOYSA-N 0.000 description 1
- DHRLEVQXOMLTIM-UHFFFAOYSA-N phosphoric acid;trioxomolybdenum Chemical class O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.OP(O)(O)=O DHRLEVQXOMLTIM-UHFFFAOYSA-N 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000011027 product recovery Methods 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 1
- 239000012808 vapor phase Substances 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
- B01J8/00—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes
- B01J8/005—Separating solid material from the gas/liquid stream
- B01J8/0055—Separating solid material from the gas/liquid stream using cyclones
-
- 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
- B01J8/00—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes
- B01J8/18—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes with fluidised particles
- B01J8/24—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes with fluidised particles according to "fluidised-bed" technique
- B01J8/26—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes with fluidised particles according to "fluidised-bed" technique with two or more fluidised beds, e.g. reactor and regeneration installations
- B01J8/28—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes with fluidised particles according to "fluidised-bed" technique with two or more fluidised beds, e.g. reactor and regeneration installations the one above the other
-
- 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
- Y02P20/584—Recycling of catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Combustion & Propulsion (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US3959270A | 1970-05-22 | 1970-05-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2124472A1 true DE2124472A1 (de) | 1971-12-02 |
Family
ID=21906300
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712124472 Pending DE2124472A1 (de) | 1970-05-22 | 1971-05-17 | Verfahren zur Herstellung von ungesättigten Nitrilen |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE765858A (enExample) |
| DE (1) | DE2124472A1 (enExample) |
| FR (1) | FR2093545A5 (enExample) |
| GB (1) | GB1304665A (enExample) |
| NL (1) | NL145846B (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2435031A1 (de) * | 1973-08-20 | 1975-02-27 | Standard Oil Co Ohio | Verfahren zur oxydativen umwandlung von kohlenwasserstoffverbindungen |
| DE2724093A1 (de) * | 1976-05-29 | 1977-12-08 | Nissan Motor | Verfahren und vorrichtung zum bestimmen der winkelverschiebung eines vor einem motorfahrzeug befindlichen objektes |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5534650A (en) * | 1994-01-12 | 1996-07-09 | Mitsubishi Chemical Corporation | Method for producing a nitrile |
| UA54409C2 (uk) * | 1997-07-16 | 2003-03-17 | Асахі Касеі Кабусікі Кайся | Спосіб одержання акрилонітрилу або метакрилонітрилу з пропану або ізобутану шляхом амоксидування |
| CN114181114B (zh) * | 2021-12-17 | 2023-09-29 | 中国五环工程有限公司 | 分步法氨氧化反应生产甲基丙烯腈的工艺及系统 |
-
1971
- 1971-04-16 BE BE765858A patent/BE765858A/xx unknown
- 1971-04-19 GB GB2617271*A patent/GB1304665A/en not_active Expired
- 1971-05-17 DE DE19712124472 patent/DE2124472A1/de active Pending
- 1971-05-19 FR FR7118278A patent/FR2093545A5/fr not_active Expired
- 1971-05-21 NL NL717106992A patent/NL145846B/xx not_active IP Right Cessation
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2435031A1 (de) * | 1973-08-20 | 1975-02-27 | Standard Oil Co Ohio | Verfahren zur oxydativen umwandlung von kohlenwasserstoffverbindungen |
| DE2724093A1 (de) * | 1976-05-29 | 1977-12-08 | Nissan Motor | Verfahren und vorrichtung zum bestimmen der winkelverschiebung eines vor einem motorfahrzeug befindlichen objektes |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1304665A (enExample) | 1973-01-24 |
| NL7106992A (enExample) | 1971-11-24 |
| FR2093545A5 (enExample) | 1972-01-28 |
| BE765858A (fr) | 1971-10-18 |
| NL145846B (nl) | 1975-05-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE3886708T2 (de) | Verfahren zur Herstellung von Nitrilen und Anhydriden. | |
| DE19832033B4 (de) | Verfahren zur Herstellung von Arcylnitril oder Methacrylnitril aus Propan oder Isobutan durch Ammoxidation | |
| DE1127351B (de) | Verfahren zur Herstellung von ª, ª-ungesaettigten aliphatischen Nitrilen durch Umsetzen von Olefinen mit Ammoniak und Sauerstoff | |
| DE2528599A1 (de) | Verfahren zur herstellung von vanadium-phosphor-sauerstoff-komplexkatalysatoren und deren verwendung | |
| DE2441109A1 (de) | Verfahren zur katalytischen oxydation von tert.-butylalkohol in der dampfphase | |
| DE69029432T2 (de) | Verfahren zur katalytischen Dehydrierung von Kohlenwasserstoffen | |
| EP0555697B1 (de) | Verfahren zur Herstellung von Dialkylcarbonaten | |
| EP0947493B1 (de) | Verfahren zur selektiven Flüssigphasenhydrierung von alpha,beta-ungesättigten Carbonylverbindungen | |
| DE69712157T2 (de) | Verfahren zur Herstellung von Acrylnitril | |
| DE1162830B (de) | Verfahren zur Herstellung von Acrylsaeurenitril und Methacrylsaeurenitril aus Propylen oder Isobutylen | |
| DE2421407B1 (de) | Verfahren zur Herstellung von Butindiol | |
| DE1568969C3 (de) | Verfahren zur Herstellung von aromatischen Polynitrilen | |
| DE69511637T2 (de) | Wiederverwendung von Ausgangsgassen in der n-Butankonversion zum Maleinsäureanhydrid | |
| DE69309106T2 (de) | Prozess zur herstellung von (meth)acrylnitril durch ammoxidation | |
| DE2703049C2 (de) | Verfahren zur Herstellung von Pyridin und 3-Methylpyridin | |
| DE19643154A1 (de) | Verfahren zur Herstellung von Oxidationsprodukten des Cyclohexans im Gegenstrom | |
| DE1301320B (de) | Verfahren zur katalytischen Synthese von Melamin aus Harnstoff | |
| DE2641846A1 (de) | Uranoxid-antimonoxidverbindung sowie herstellung und verwendung derselben als katalysator | |
| DE2248498C3 (de) | Verfahren zur Herstellung von olefinisch ungesättigten Nitrilen | |
| DE882402C (de) | Reaktionsgefaess und Verfahren zur Durchfuehrung chemischer Reaktionen | |
| DE2461184C2 (de) | Antimon, Eisen, Wismut und Molybdän, sowie gegebenenfalls Kobalt und Nickel enthaltender Katalysator und seine Verwendung | |
| DE69908442T2 (de) | Verfahren zum Herstellen von Maleinsäureanhydrid | |
| DE2248498B2 (de) | Verfahren zur herstellung von olefinisch ungesaettigten nitrilen | |
| DE1593332A1 (de) | Verfahren zur Herstellung von Acrolein | |
| DE2264528A1 (de) | Verfahren zur synthese ungesaettigter aldehyde |