RU2312851C2 - Способ получения акролеина, или акриловой кислоты, или их смесей из пропана - Google Patents
Способ получения акролеина, или акриловой кислоты, или их смесей из пропана Download PDFInfo
- Publication number
- RU2312851C2 RU2312851C2 RU2003100831/04A RU2003100831A RU2312851C2 RU 2312851 C2 RU2312851 C2 RU 2312851C2 RU 2003100831/04 A RU2003100831/04 A RU 2003100831/04A RU 2003100831 A RU2003100831 A RU 2003100831A RU 2312851 C2 RU2312851 C2 RU 2312851C2
- Authority
- RU
- Russia
- Prior art keywords
- gas mixture
- propane
- stage
- propylene
- contained
- Prior art date
Links
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 title claims abstract description 283
- 239000000203 mixture Substances 0.000 title claims abstract description 205
- 239000001294 propane Substances 0.000 title claims abstract description 141
- 238000000034 method Methods 0.000 title claims abstract description 108
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 title claims abstract description 66
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 title claims abstract description 32
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 title claims abstract description 31
- 239000007789 gas Substances 0.000 claims abstract description 173
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims abstract description 120
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 115
- 230000003647 oxidation Effects 0.000 claims abstract description 111
- 238000006356 dehydrogenation reaction Methods 0.000 claims abstract description 87
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims abstract description 64
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 53
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims abstract description 35
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 34
- 229910001882 dioxygen Inorganic materials 0.000 claims abstract description 34
- 238000011068 loading method Methods 0.000 claims abstract description 16
- 238000002955 isolation Methods 0.000 claims abstract 2
- 239000003054 catalyst Substances 0.000 claims description 105
- 238000006243 chemical reaction Methods 0.000 claims description 83
- 239000012495 reaction gas Substances 0.000 claims description 48
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 31
- 239000003085 diluting agent Substances 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 238000002485 combustion reaction Methods 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 238000003795 desorption Methods 0.000 claims description 2
- 239000000047 product Substances 0.000 abstract description 23
- 239000006227 byproduct Substances 0.000 abstract description 16
- 230000015572 biosynthetic process Effects 0.000 abstract description 14
- 239000000126 substance Substances 0.000 abstract description 5
- 230000000694 effects Effects 0.000 abstract description 3
- 230000003247 decreasing effect Effects 0.000 abstract description 2
- 238000005516 engineering process Methods 0.000 abstract description 2
- 239000008246 gaseous mixture Substances 0.000 abstract 6
- 239000007795 chemical reaction product Substances 0.000 abstract 2
- 238000003786 synthesis reaction Methods 0.000 abstract 2
- 238000007865 diluting Methods 0.000 abstract 1
- 239000007792 gaseous phase Substances 0.000 abstract 1
- 239000012071 phase Substances 0.000 abstract 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 34
- 229910052760 oxygen Inorganic materials 0.000 description 20
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 17
- 239000001301 oxygen Substances 0.000 description 17
- 235000019260 propionic acid Nutrition 0.000 description 17
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 17
- 230000008569 process Effects 0.000 description 16
- 238000000926 separation method Methods 0.000 description 16
- 239000000243 solution Substances 0.000 description 16
- 229910002091 carbon monoxide Inorganic materials 0.000 description 15
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 12
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- 229910044991 metal oxide Inorganic materials 0.000 description 10
- 150000004706 metal oxides Chemical class 0.000 description 10
- 239000000843 powder Substances 0.000 description 9
- 230000008929 regeneration Effects 0.000 description 9
- 238000011069 regeneration method Methods 0.000 description 9
- 238000001179 sorption measurement Methods 0.000 description 9
- 238000009835 boiling Methods 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 8
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 230000008901 benefit Effects 0.000 description 7
- 238000001354 calcination Methods 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 7
- 239000007921 spray Substances 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- 239000005977 Ethylene Substances 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- -1 methane Chemical class 0.000 description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-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
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 5
- 229910004298 SiO 2 Inorganic materials 0.000 description 5
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 5
- 238000009833 condensation Methods 0.000 description 5
- 230000005494 condensation Effects 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 238000011049 filling Methods 0.000 description 5
- 229930195733 hydrocarbon Natural products 0.000 description 5
- 150000002430 hydrocarbons Chemical class 0.000 description 5
- 239000011261 inert gas Substances 0.000 description 5
- 229910052756 noble gas Inorganic materials 0.000 description 5
- 150000002835 noble gases Chemical class 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 4
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 4
- 238000010790 dilution Methods 0.000 description 4
- 239000012895 dilution Substances 0.000 description 4
- 238000002407 reforming Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 229910000831 Steel Inorganic materials 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 125000006267 biphenyl group Chemical group 0.000 description 3
- 239000003245 coal Substances 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 230000002209 hydrophobic effect Effects 0.000 description 3
- 239000003701 inert diluent Substances 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- 229910000510 noble metal Inorganic materials 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
- 229910052697 platinum Inorganic materials 0.000 description 3
- MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical compound CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 description 3
- 239000010959 steel Substances 0.000 description 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 2
- 239000002250 absorbent Substances 0.000 description 2
- 230000002745 absorbent Effects 0.000 description 2
- 239000006096 absorbing agent Substances 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 239000001273 butane Substances 0.000 description 2
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 2
- 238000007084 catalytic combustion reaction Methods 0.000 description 2
- 229910000423 chromium oxide Inorganic materials 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 238000005336 cracking Methods 0.000 description 2
- 238000005485 electric heating Methods 0.000 description 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- OVBPIULPVIDEAO-LBPRGKRZSA-N folic acid Chemical compound C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-LBPRGKRZSA-N 0.000 description 2
- 238000002309 gasification Methods 0.000 description 2
- 229910002804 graphite Inorganic materials 0.000 description 2
- 239000010439 graphite Substances 0.000 description 2
- 229910052734 helium Inorganic materials 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 238000012856 packing Methods 0.000 description 2
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- 239000004014 plasticizer Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000012552 review Methods 0.000 description 2
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- 238000003756 stirring Methods 0.000 description 2
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- 229910052721 tungsten Inorganic materials 0.000 description 2
- 238000005406 washing Methods 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
- RXWOHFUULDINMC-UHFFFAOYSA-N 2-(3-nitrothiophen-2-yl)acetic acid Chemical compound OC(=O)CC=1SC=CC=1[N+]([O-])=O RXWOHFUULDINMC-UHFFFAOYSA-N 0.000 description 1
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- MJBPUQUGJNAPAZ-UHFFFAOYSA-N Butine Natural products O1C2=CC(O)=CC=C2C(=O)CC1C1=CC=C(O)C(O)=C1 MJBPUQUGJNAPAZ-UHFFFAOYSA-N 0.000 description 1
- SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 description 1
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 1
- OVBPIULPVIDEAO-UHFFFAOYSA-N N-Pteroyl-L-glutaminsaeure Natural products C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)NC(CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-UHFFFAOYSA-N 0.000 description 1
- 206010063493 Premature ageing Diseases 0.000 description 1
- 208000032038 Premature aging Diseases 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
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- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 239000003570 air Substances 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- UNTBPXHCXVWYOI-UHFFFAOYSA-O azanium;oxido(dioxo)vanadium Chemical compound [NH4+].[O-][V](=O)=O UNTBPXHCXVWYOI-UHFFFAOYSA-O 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- WXBLLCUINBKULX-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1.OC(=O)C1=CC=CC=C1 WXBLLCUINBKULX-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001722 carbon compounds Chemical class 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000012018 catalyst precursor Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007809 chemical reaction catalyst Substances 0.000 description 1
- 125000001309 chloro group Chemical class Cl* 0.000 description 1
- UFMZWBIQTDUYBN-UHFFFAOYSA-N cobalt dinitrate Chemical compound [Co+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O UFMZWBIQTDUYBN-UHFFFAOYSA-N 0.000 description 1
- 229910001981 cobalt nitrate 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
- 239000002826 coolant Substances 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical class CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 1
- FBSAITBEAPNWJG-UHFFFAOYSA-N dimethyl phthalate Natural products CC(=O)OC1=CC=CC=C1OC(C)=O FBSAITBEAPNWJG-UHFFFAOYSA-N 0.000 description 1
- 229960001826 dimethylphthalate Drugs 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
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- 230000002349 favourable effect Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 229960000304 folic acid Drugs 0.000 description 1
- 235000019152 folic acid Nutrition 0.000 description 1
- 239000011724 folic acid Substances 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 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
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 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 1
- 238000009434 installation Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- MVFCKEFYUDZOCX-UHFFFAOYSA-N iron(2+);dinitrate Chemical compound [Fe+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O MVFCKEFYUDZOCX-UHFFFAOYSA-N 0.000 description 1
- 230000002262 irrigation Effects 0.000 description 1
- 238000003973 irrigation Methods 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
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- 239000002609 medium Substances 0.000 description 1
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- 239000002184 metal Substances 0.000 description 1
- 229930182817 methionine Natural products 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229910052754 neon Inorganic materials 0.000 description 1
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluenecarboxylic acid Natural products CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 238000005839 oxidative dehydrogenation reaction Methods 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- GPRIERYVMZVKTC-UHFFFAOYSA-N p-quaterphenyl Chemical group C1=CC=CC=C1C1=CC=C(C=2C=CC(=CC=2)C=2C=CC=CC=2)C=C1 GPRIERYVMZVKTC-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 238000005453 pelletization Methods 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 150000003021 phthalic acid derivatives Chemical class 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
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- 230000005855 radiation Effects 0.000 description 1
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- 230000011514 reflex Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
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- 238000005029 sieve analysis Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
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- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
Classifications
-
- 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
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
- C07C51/215—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of saturated hydrocarbyl groups
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/32—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with formation of free hydrogen
- C07C5/327—Formation of non-aromatic carbon-to-carbon double bonds only
- C07C5/333—Catalytic processes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
- C07C51/25—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of unsaturated compounds containing no six-membered aromatic ring
- C07C51/252—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of unsaturated compounds containing no six-membered aromatic ring of propene, butenes, acrolein or methacrolein
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10028582.1 | 2000-06-14 | ||
| DE10028582A DE10028582A1 (de) | 2000-06-14 | 2000-06-14 | Verfahren zur Herstellung von Acrolein oder Acrylsäure oder deren Gemischen aus Propan |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2003100831A RU2003100831A (ru) | 2004-07-10 |
| RU2312851C2 true RU2312851C2 (ru) | 2007-12-20 |
Family
ID=7645236
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2003100831/04A RU2312851C2 (ru) | 2000-06-14 | 2001-06-08 | Способ получения акролеина, или акриловой кислоты, или их смесей из пропана |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US6781017B2 (enExample) |
| EP (1) | EP1289920B1 (enExample) |
| JP (1) | JP5021139B2 (enExample) |
| KR (1) | KR100696330B1 (enExample) |
| CN (1) | CN1211339C (enExample) |
| AT (1) | ATE276224T1 (enExample) |
| AU (1) | AU2001281823A1 (enExample) |
| BR (1) | BR0111607B1 (enExample) |
| CZ (1) | CZ304023B6 (enExample) |
| DE (2) | DE10028582A1 (enExample) |
| ES (1) | ES2228925T3 (enExample) |
| MY (1) | MY123581A (enExample) |
| RU (1) | RU2312851C2 (enExample) |
| SA (1) | SA01220159B1 (enExample) |
| TW (1) | TWI268920B (enExample) |
| WO (1) | WO2001096270A2 (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2678847C2 (ru) * | 2013-09-17 | 2019-02-04 | Басф Се | Катализатор для синтеза ненасыщенной карбоновой кислоты путем газофазного окисления ненасыщенного альдегида |
| RU2715605C1 (ru) * | 2016-07-25 | 2020-03-03 | Мицубиси Кемикал Корпорейшн | Катализатор, способ получения акриловой кислоты и способ получения катализатора |
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| DE10240129B4 (de) | 2002-08-30 | 2004-11-11 | Basf Ag | Integriertes Verfahren zur Synthese von Propylenoxid |
| US7326802B2 (en) * | 2002-09-27 | 2008-02-05 | Basf Aktiengesellschaft | Preparation of at least one partial oxidation and/or ammoxidation product of propylene |
| DE10245585A1 (de) * | 2002-09-27 | 2004-04-08 | Basf Ag | Verfahren zur Herstellung von wenigstens einem partiellen Oxidations- und/oder Ammoxidationsprodukt des Propylens |
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| US7589046B2 (en) * | 2003-06-04 | 2009-09-15 | Basf Aktiengesellschaft | Thermal treatment of the precursor material of a catalytically active material |
| JP2007501193A (ja) | 2003-08-06 | 2007-01-25 | ビーエーエスエフ アクチェンゲゼルシャフト | 少なくとも１の有機化合物を不均一系触媒により連続的に気相部分酸化する方法 |
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| US8431743B2 (en) * | 2004-07-01 | 2013-04-30 | Basf Aktiengesellschaft | Preparation of acrylic acid by heterogeneously catalyzed partial gas phase oxidation of propylene |
| DE102004059355A1 (de) * | 2004-12-09 | 2006-06-14 | Basf Ag | Verfahren zur Herstellung von Propan zu Propen |
| DE102004061772A1 (de) * | 2004-12-22 | 2006-07-06 | Basf Ag | Verfahren zur Herstellung von Propen aus Propan |
| US7439389B2 (en) | 2005-03-01 | 2008-10-21 | Basf Aktiengesellschaft | Process for preparing at least one organic target compound by heterogeneously catalyzed gas phase partial oxidation |
| 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 |
| US7705181B2 (en) * | 2005-03-01 | 2010-04-27 | Basf Akiengesellschaft | Process for removing methacrylic acid from liquid phase comprising acrylic acid as a main constituent and target product, and methacrylic acid as a secondary component |
| DE102005019911A1 (de) | 2005-04-27 | 2006-11-02 | Basf Ag | Verfahren der rektifikativen Auftrennung einer Acrylsäure und/oder Methacrylsäure enthaltenden Flüssigkeit |
| US7388106B2 (en) * | 2005-10-14 | 2008-06-17 | Basf Aktiengesellschaft | Process for preparing acrolein or acrylic acid or a mixture thereof from propane |
| RU2429218C2 (ru) * | 2005-10-14 | 2011-09-20 | Басф Се | Способ получения акролеина, акриловой кислоты или их смеси из пропана |
| KR101278795B1 (ko) * | 2005-11-03 | 2013-06-25 | 바스프 에스이 | 프로판으로부터 아크롤레인 또는 아크릴산 또는 그의혼합물을 수득하기 위한 안정한 연속 제조 방법 |
| DE102005052923A1 (de) * | 2005-11-03 | 2007-05-10 | Basf Ag | Verfahren zum stabilen Betreiben eines kontinuierlich ausgeübten Herstellprozesses zur Erzeugung von Acrolein, oder Acrylsäure oder deren Gemisch aus Propan |
| RU2430083C9 (ru) * | 2005-11-24 | 2012-09-20 | Басф Се | Способ получения акриловой кислоты из пропана |
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| DE102005062010A1 (de) | 2005-12-22 | 2007-06-28 | Basf Ag | Verfahren der heterogen katalysierten partiellen Gasphasenoxidation von Propylen zu Acrylsäure |
| DE102005062026A1 (de) * | 2005-12-22 | 2007-06-28 | Basf Ag | Verfahren der heterogen katalysierten partiellen Gasphasenoxidation von Propylen zu Acrylsäure |
| DE102006000996A1 (de) | 2006-01-05 | 2007-07-12 | Basf Ag | Verfahren der heterogen katalysierten Gasphasen-Partialoxidation wenigstens einer organischen Ausgangsverbindung |
| EP1734030A1 (de) | 2006-01-18 | 2006-12-20 | BASF Aktiengesellschaft | Verfahren zum Langzeitbetrieb einer heterogen katalysierten partiellen Gasphasenoxidation einer organischen Ausgangsverbindung |
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| WO2018080333A1 (en) * | 2016-10-31 | 2018-05-03 | Public Joint Stock Company "Sibur Holding" | Process for production of acrylic acid, process for the selective oxidation of carbon monoxide, catalyst for the selective oxidation of carbon monoxide, process for producing the same |
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| CN115335354A (zh) | 2020-03-26 | 2022-11-11 | 巴斯夫欧洲公司 | 抑制存在于液相p中的丙烯酸的不期望的自由基聚合的方法 |
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- 2000-06-14 DE DE10028582A patent/DE10028582A1/de not_active Withdrawn
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- 2001-05-24 TW TW090112528A patent/TWI268920B/zh not_active IP Right Cessation
- 2001-06-08 KR KR1020027017044A patent/KR100696330B1/ko not_active Expired - Fee Related
- 2001-06-08 RU RU2003100831/04A patent/RU2312851C2/ru not_active IP Right Cessation
- 2001-06-08 ES ES01960291T patent/ES2228925T3/es not_active Expired - Lifetime
- 2001-06-08 CN CNB018110975A patent/CN1211339C/zh not_active Expired - Fee Related
- 2001-06-08 DE DE50103645T patent/DE50103645D1/de not_active Expired - Lifetime
- 2001-06-08 US US10/297,602 patent/US6781017B2/en not_active Expired - Lifetime
- 2001-06-08 WO PCT/EP2001/006528 patent/WO2001096270A2/de not_active Ceased
- 2001-06-08 EP EP01960291A patent/EP1289920B1/de not_active Expired - Lifetime
- 2001-06-08 JP JP2002510416A patent/JP5021139B2/ja not_active Expired - Fee Related
- 2001-06-08 CZ CZ20024057A patent/CZ304023B6/cs not_active IP Right Cessation
- 2001-06-08 AT AT01960291T patent/ATE276224T1/de not_active IP Right Cessation
- 2001-06-08 BR BRPI0111607-0A patent/BR0111607B1/pt not_active IP Right Cessation
- 2001-06-08 AU AU2001281823A patent/AU2001281823A1/en not_active Abandoned
- 2001-06-11 SA SA01220159A patent/SA01220159B1/ar unknown
- 2001-06-14 MY MYPI20012796 patent/MY123581A/en unknown
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4453006A (en) * | 1979-09-17 | 1984-06-05 | The Standard Oil Company | Oxidation of propylene or isobutylene with attrition resistant catalysts |
| GB2118939A (en) * | 1982-04-14 | 1983-11-09 | Halcon Sd Group Inc | Conversion of alkanes to unsaturated aldehydes |
| US5198578A (en) * | 1986-07-17 | 1993-03-30 | Union Carbide Chemicals | Anhydrous diluents for the propylene oxidation reaction to acrolein and acrolein oxidation to acrylic acid |
| US5183936A (en) * | 1986-08-21 | 1993-02-02 | Union Carbide Chemicals & Plastics Technology Corporation | Anhydrous diluent process for the propylene oxidation reaction to acrolein and acrolein oxidation to acrylic acid |
| US5705684A (en) * | 1995-03-10 | 1998-01-06 | Basf Aktiengesellschaft | Preparation of acrolein, acrylic acid or a mixture thereof from propane |
| DE19837517A1 (de) * | 1998-08-19 | 2000-02-24 | Basf Ag | Verfahren zur Herstellung von Acrolein und/oder Acrylsäure aus Propan |
| DE19837518A1 (de) * | 1998-08-19 | 2000-02-24 | Basf Ag | Verfahren zur Herstellung von Acrolein und/oder Acrylsäure aus Propan |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2678847C2 (ru) * | 2013-09-17 | 2019-02-04 | Басф Се | Катализатор для синтеза ненасыщенной карбоновой кислоты путем газофазного окисления ненасыщенного альдегида |
| RU2715605C1 (ru) * | 2016-07-25 | 2020-03-03 | Мицубиси Кемикал Корпорейшн | Катализатор, способ получения акриловой кислоты и способ получения катализатора |
| US11084029B2 (en) | 2016-07-25 | 2021-08-10 | Mitsubishi Chemical Corporation | Catalyst, acrylic acid production method, and catalyst production method |
Also Published As
| Publication number | Publication date |
|---|---|
| CZ304023B6 (cs) | 2013-08-28 |
| BR0111607B1 (pt) | 2012-01-24 |
| ES2228925T3 (es) | 2005-04-16 |
| US20030181762A1 (en) | 2003-09-25 |
| DE50103645D1 (de) | 2004-10-21 |
| ATE276224T1 (de) | 2004-10-15 |
| CN1436160A (zh) | 2003-08-13 |
| KR100696330B1 (ko) | 2007-03-21 |
| TWI268920B (en) | 2006-12-21 |
| BR0111607A (pt) | 2003-07-01 |
| SA01220159B1 (ar) | 2006-10-29 |
| EP1289920B1 (de) | 2004-09-15 |
| WO2001096270A3 (de) | 2002-04-25 |
| MY123581A (en) | 2006-05-31 |
| DE10028582A1 (de) | 2001-12-20 |
| EP1289920A2 (de) | 2003-03-12 |
| JP2004503516A (ja) | 2004-02-05 |
| KR20030009525A (ko) | 2003-01-29 |
| CN1211339C (zh) | 2005-07-20 |
| US6781017B2 (en) | 2004-08-24 |
| WO2001096270A2 (de) | 2001-12-20 |
| JP5021139B2 (ja) | 2012-09-05 |
| CZ20024057A3 (cs) | 2003-05-14 |
| AU2001281823A1 (en) | 2001-12-24 |
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| MM4A | The patent is invalid due to non-payment of fees |
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