EP1404647A1 - Verfahren zur herstellung von ungesättigten nitrilen aus alkanen - Google Patents

Verfahren zur herstellung von ungesättigten nitrilen aus alkanen

Info

Publication number: EP1404647A1
Authority: EP; European Patent Office
Prior art keywords: alkane; alkene; gas stream; ammonia; dehydrogenation
Prior art date: 2001-06-29
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 Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Withdrawn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)

French (fr)

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.)

2001-06-29

Filing date

2002-06-25

Publication date

2004-04-07

2001-06-29 Priority claimed from DE10131297A external-priority patent/DE10131297A1/de

2002-03-13 Priority claimed from DE10211275A external-priority patent/DE10211275A1/de

2002-04-22 Priority claimed from DE2002117844 external-priority patent/DE10217844A1/de

2002-06-25 Application filed by BASF SE filed Critical BASF SE

2004-04-07 Publication of EP1404647A1 publication Critical patent/EP1404647A1/de

Status Withdrawn legal-status Critical Current

Links

150000001335 aliphatic alkanes Chemical class 0.000 title claims abstract description 84
238000000034 method Methods 0.000 title claims abstract description 45
150000002825 nitriles Chemical class 0.000 title claims abstract description 33
238000004519 manufacturing process Methods 0.000 title abstract description 9
239000007789 gas Substances 0.000 claims abstract description 133
238000006356 dehydrogenation reaction Methods 0.000 claims abstract description 85
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 76
239000000047 product Substances 0.000 claims abstract description 60
150000001336 alkenes Chemical class 0.000 claims abstract description 56
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 48
229910052760 oxygen Inorganic materials 0.000 claims abstract description 48
239000001301 oxygen Substances 0.000 claims abstract description 48
229910021529 ammonia Inorganic materials 0.000 claims abstract description 38
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 35
239000001257 hydrogen Substances 0.000 claims abstract description 35
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 34
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 28
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical class [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims abstract description 19
239000006227 byproduct Substances 0.000 claims abstract description 18
229910002090 carbon oxide Inorganic materials 0.000 claims abstract description 17
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 17
230000003197 catalytic effect Effects 0.000 claims abstract description 15
229910001868 water Inorganic materials 0.000 claims abstract description 15
238000009835 boiling Methods 0.000 claims abstract description 14
229930195733 hydrocarbon Natural products 0.000 claims abstract description 14
150000002430 hydrocarbons Chemical class 0.000 claims abstract description 14
230000003647 oxidation Effects 0.000 claims abstract description 14
238000007254 oxidation reaction Methods 0.000 claims abstract description 14
229910052756 noble gas Inorganic materials 0.000 claims abstract description 13
150000002835 noble gases Chemical class 0.000 claims abstract description 13
150000002431 hydrogen Chemical class 0.000 claims abstract description 10
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical group CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 30
238000010521 absorption reaction Methods 0.000 claims description 23
QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 20
239000001294 propane Substances 0.000 claims description 15
238000000926 separation method Methods 0.000 claims description 14
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical group C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 13
239000000470 constituent Substances 0.000 claims description 9
VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 6
NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 claims description 6
GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical group CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 claims description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 claims description 4
229910052921 ammonium sulfate Inorganic materials 0.000 claims description 4
235000011130 ammonium sulphate Nutrition 0.000 claims description 4
239000001282 iso-butane Substances 0.000 claims description 3
238000011084 recovery Methods 0.000 claims description 2
238000005406 washing Methods 0.000 claims description 2
238000002360 preparation method Methods 0.000 claims 1
239000003795 chemical substances by application Substances 0.000 abstract description 5
239000003054 catalyst Substances 0.000 description 52
239000000203 mixture Substances 0.000 description 35
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 27
238000006243 chemical reaction Methods 0.000 description 17
239000002250 absorbent Substances 0.000 description 13
230000002745 absorbent Effects 0.000 description 13
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 12
239000012495 reaction gas Substances 0.000 description 10
229910002091 carbon monoxide Inorganic materials 0.000 description 8
238000002485 combustion reaction Methods 0.000 description 7
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
229910002092 carbon dioxide Inorganic materials 0.000 description 6
239000001569 carbon dioxide Substances 0.000 description 6
238000004821 distillation Methods 0.000 description 6
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 6
NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 5
238000003795 desorption Methods 0.000 description 5
238000010438 heat treatment Methods 0.000 description 5
239000006096 absorbing agent Substances 0.000 description 4
238000010790 dilution Methods 0.000 description 4
239000012895 dilution Substances 0.000 description 4
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 4
LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 4
230000001590 oxidative effect Effects 0.000 description 4
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 3
MCMNRKCIXSYSNV-UHFFFAOYSA-N ZrO2 Inorganic materials O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
238000001816 cooling Methods 0.000 description 3
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 3
RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 3
230000008092 positive effect Effects 0.000 description 3
239000000377 silicon dioxide Substances 0.000 description 3
235000012239 silicon dioxide Nutrition 0.000 description 3
229910052718 tin Inorganic materials 0.000 description 3
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 2
229910019142 PO4 Inorganic materials 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
229910052768 actinide Inorganic materials 0.000 description 2
150000001255 actinides Chemical class 0.000 description 2
239000004305 biphenyl Substances 0.000 description 2
235000010290 biphenyl Nutrition 0.000 description 2
XSIFPSYPOVKYCO-UHFFFAOYSA-N butyl benzoate Chemical compound CCCCOC(=O)C1=CC=CC=C1 XSIFPSYPOVKYCO-UHFFFAOYSA-N 0.000 description 2
230000018044 dehydration Effects 0.000 description 2
238000006297 dehydration reaction Methods 0.000 description 2
239000002781 deodorant agent Substances 0.000 description 2
238000004332 deodorization Methods 0.000 description 2
FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 2
FBSAITBEAPNWJG-UHFFFAOYSA-N dimethyl phthalate Natural products CC(=O)OC1=CC=CC=C1OC(C)=O FBSAITBEAPNWJG-UHFFFAOYSA-N 0.000 description 2
229960001826 dimethylphthalate Drugs 0.000 description 2
230000000694 effects Effects 0.000 description 2
MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 2
239000002360 explosive Substances 0.000 description 2
230000002349 favourable effect Effects 0.000 description 2
229910052732 germanium Inorganic materials 0.000 description 2
GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 2
239000011261 inert gas Substances 0.000 description 2
229910052747 lanthanoid Inorganic materials 0.000 description 2
150000002602 lanthanoids Chemical class 0.000 description 2
MRELNEQAGSRDBK-UHFFFAOYSA-N lanthanum(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[La+3].[La+3] MRELNEQAGSRDBK-UHFFFAOYSA-N 0.000 description 2
239000003949 liquefied natural gas Substances 0.000 description 2
239000003915 liquefied petroleum gas Substances 0.000 description 2
239000012528 membrane Substances 0.000 description 2
QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
239000003921 oil Substances 0.000 description 2
238000005839 oxidative dehydrogenation reaction Methods 0.000 description 2
235000021317 phosphate Nutrition 0.000 description 2
150000003013 phosphoric acid derivatives Chemical class 0.000 description 2
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
229910052697 platinum Inorganic materials 0.000 description 2
238000005201 scrubbing Methods 0.000 description 2
239000000243 solution Substances 0.000 description 2
MHCVCKDNQYMGEX-UHFFFAOYSA-N 1,1'-biphenyl;phenoxybenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1.C=1C=CC=CC=1OC1=CC=CC=C1 MHCVCKDNQYMGEX-UHFFFAOYSA-N 0.000 description 1
YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
AIZXVIAKTHPYCS-UHFFFAOYSA-N 2-methylprop-1-ene;2-methylprop-2-enenitrile Chemical compound CC(C)=C.CC(=C)C#N AIZXVIAKTHPYCS-UHFFFAOYSA-N 0.000 description 1
ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 1
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
229910052684 Cerium Inorganic materials 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
STNJBCKSHOAVAJ-UHFFFAOYSA-N Methacrolein Chemical compound CC(=C)C=O STNJBCKSHOAVAJ-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
230000002411 adverse Effects 0.000 description 1
239000003570 air Substances 0.000 description 1
JYMITAMFTJDTAE-UHFFFAOYSA-N aluminum zinc oxygen(2-) Chemical compound [O-2].[Al+3].[Zn+2] JYMITAMFTJDTAE-UHFFFAOYSA-N 0.000 description 1
239000001099 ammonium carbonate Substances 0.000 description 1
235000012501 ammonium carbonate Nutrition 0.000 description 1
229910052787 antimony Inorganic materials 0.000 description 1
WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
229910052785 arsenic Inorganic materials 0.000 description 1
RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 1
ZCILODAAHLISPY-UHFFFAOYSA-N biphenyl ether Natural products C1=C(CC=C)C(O)=CC(OC=2C(=CC(CC=C)=CC=2)O)=C1 ZCILODAAHLISPY-UHFFFAOYSA-N 0.000 description 1
229910052797 bismuth Inorganic materials 0.000 description 1
JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
229910052796 boron Inorganic materials 0.000 description 1
239000001273 butane Substances 0.000 description 1
229910052792 caesium Inorganic materials 0.000 description 1
TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
GWXLDORMOJMVQZ-UHFFFAOYSA-N cerium Chemical compound [Ce] GWXLDORMOJMVQZ-UHFFFAOYSA-N 0.000 description 1
229910000420 cerium oxide Inorganic materials 0.000 description 1
239000000571 coke Substances 0.000 description 1
238000004939 coking Methods 0.000 description 1
239000000567 combustion gas Substances 0.000 description 1
230000006835 compression Effects 0.000 description 1
238000007906 compression Methods 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
239000000110 cooling liquid Substances 0.000 description 1
SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical class CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
229940052296 esters of benzoic acid for local anesthesia Drugs 0.000 description 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
239000010408 film Substances 0.000 description 1
239000000446 fuel Substances 0.000 description 1
239000002737 fuel gas Substances 0.000 description 1
229910052733 gallium Inorganic materials 0.000 description 1
238000002309 gasification Methods 0.000 description 1
229910002804 graphite Inorganic materials 0.000 description 1
239000010439 graphite Substances 0.000 description 1
NDJKXXJCMXVBJW-UHFFFAOYSA-N heptadecane Chemical class CCCCCCCCCCCCCCCCC NDJKXXJCMXVBJW-UHFFFAOYSA-N 0.000 description 1
DCAYPVUWAIABOU-UHFFFAOYSA-N hexadecane Chemical class CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 0.000 description 1
229910052738 indium Inorganic materials 0.000 description 1
APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
229910052746 lanthanum Inorganic materials 0.000 description 1
FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
239000000395 magnesium oxide Substances 0.000 description 1
CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
229910044991 metal oxide Inorganic materials 0.000 description 1
150000004706 metal oxides Chemical class 0.000 description 1
-1 methane Chemical class 0.000 description 1
229940095102 methyl benzoate Drugs 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
125000002560 nitrile group Chemical group 0.000 description 1
229910000510 noble metal Inorganic materials 0.000 description 1
239000012454 non-polar solvent Substances 0.000 description 1
RZJRJXONCZWCBN-UHFFFAOYSA-N octadecane Chemical class CCCCCCCCCCCCCCCCCC RZJRJXONCZWCBN-UHFFFAOYSA-N 0.000 description 1
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 1
238000012856 packing Methods 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
YCOZIPAWZNQLMR-UHFFFAOYSA-N pentadecane Chemical class CCCCCCCCCCCCCCC YCOZIPAWZNQLMR-UHFFFAOYSA-N 0.000 description 1
239000006069 physical mixture Substances 0.000 description 1
239000003495 polar organic solvent Substances 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical compound CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 description 1
238000010791 quenching Methods 0.000 description 1
238000004064 recycling Methods 0.000 description 1
238000002407 reforming Methods 0.000 description 1
230000008929 regeneration Effects 0.000 description 1
238000011069 regeneration method Methods 0.000 description 1
230000002040 relaxant effect Effects 0.000 description 1
229910052710 silicon Inorganic materials 0.000 description 1
239000010703 silicon Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
BGHCVCJVXZWKCC-UHFFFAOYSA-N tetradecane Chemical class CCCCCCCCCCCCCC BGHCVCJVXZWKCC-UHFFFAOYSA-N 0.000 description 1
239000010409 thin film Substances 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
IIYFAKIEWZDVMP-UHFFFAOYSA-N tridecane Chemical class CCCCCCCCCCCCC IIYFAKIEWZDVMP-UHFFFAOYSA-N 0.000 description 1
RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical class CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 1
238000011144 upstream manufacturing Methods 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1
239000011787 zinc oxide 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
- 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.

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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)

EP02762301A 2001-06-29 2002-06-25 Verfahren zur herstellung von ungesättigten nitrilen aus alkanen Withdrawn EP1404647A1 (de)

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
DE10211275		2002-03-13
DE10211275A DE10211275A1 (de)	2002-03-13	2002-03-13	Verfahren der kontinuierlichen heterogen katalysierten partiellen Dehydrierung
DE10217844		2002-04-22
DE2002117844 DE10217844A1 (de)	2002-04-22	2002-04-22	Verfahren zur Herstellung von ungesättigten Nitrilen aus Alkanen
PCT/EP2002/007024 WO2003002520A1 (de)	2001-06-29	2002-06-25	Verfahren zur herstellung von ungesättigten nitrilen aus alkanen

Publications (1)

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

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EP02762301A Withdrawn EP1404647A1 (de)	2001-06-29	2002-06-25	Verfahren zur herstellung von ungesättigten nitrilen aus alkanen

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

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DE10217845A1 (de) *	2002-04-22	2003-11-06	Basf Ag	Verfahren zur Herstellung von ungesättigten Nitrilen
BRPI0509632B1 (pt) *	2004-05-07	2015-09-08	Basf Aktiengesellschaft	processo para carregamento de tubos de contato de um feixe de tubos de contato de uma maneira estruturada
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

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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

2002
- 2002-06-25 WO PCT/EP2002/007024 patent/WO2003002520A1/de not_active Ceased
- 2002-06-25 JP JP2003508703A patent/JP2004532283A/ja active Pending
- 2002-06-25 EP EP02762301A patent/EP1404647A1/de not_active Withdrawn
- 2002-06-25 CN CNB028130286A patent/CN1229338C/zh not_active Expired - Fee Related
- 2002-06-25 KR KR10-2003-7017105A patent/KR20040034619A/ko not_active Ceased
- 2002-06-25 US US10/482,326 patent/US7271279B2/en not_active Expired - Fee Related
- 2002-08-11 SA SA02230243A patent/SA02230243B1/ar unknown

Non-Patent Citations (1)

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

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

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