RU2628519C2 - Способ окислительного дегидрирования с улучшенной регулируемостью для получения бутадиена - Google Patents
Способ окислительного дегидрирования с улучшенной регулируемостью для получения бутадиена Download PDFInfo
- Publication number
- RU2628519C2 RU2628519C2 RU2014143515A RU2014143515A RU2628519C2 RU 2628519 C2 RU2628519 C2 RU 2628519C2 RU 2014143515 A RU2014143515 A RU 2014143515A RU 2014143515 A RU2014143515 A RU 2014143515A RU 2628519 C2 RU2628519 C2 RU 2628519C2
- Authority
- RU
- Russia
- Prior art keywords
- butene
- oxidative dehydrogenation
- catalyst
- butadiene
- layer
- Prior art date
Links
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 title claims abstract description 176
- 238000000034 method Methods 0.000 title claims abstract description 55
- 230000018044 dehydration Effects 0.000 title 1
- 238000006297 dehydration reaction Methods 0.000 title 1
- 230000001590 oxidative effect Effects 0.000 title 1
- 239000003054 catalyst Substances 0.000 claims abstract description 134
- 238000005839 oxidative dehydrogenation reaction Methods 0.000 claims abstract description 68
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 53
- 239000001301 oxygen Substances 0.000 claims abstract description 53
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 53
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 48
- 238000006243 chemical reaction Methods 0.000 claims abstract description 47
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 44
- 230000003197 catalytic effect Effects 0.000 claims abstract description 35
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 33
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims abstract description 32
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 claims abstract description 32
- 239000007789 gas Substances 0.000 claims abstract description 22
- 238000001704 evaporation Methods 0.000 claims abstract description 7
- 238000002156 mixing Methods 0.000 claims abstract description 5
- 239000008188 pellet Substances 0.000 claims abstract 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 33
- 239000002245 particle Substances 0.000 claims description 25
- 238000004519 manufacturing process Methods 0.000 claims description 19
- 238000007254 oxidation reaction Methods 0.000 claims description 17
- 230000003647 oxidation Effects 0.000 claims description 16
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 14
- 150000001345 alkine derivatives Chemical class 0.000 claims description 12
- 238000006356 dehydrogenation reaction Methods 0.000 claims description 11
- 235000016709 nutrition Nutrition 0.000 claims description 11
- 230000035764 nutrition Effects 0.000 claims description 11
- 239000008187 granular material Substances 0.000 claims description 9
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 8
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 8
- 238000011068 loading method Methods 0.000 claims description 8
- 229910000859 α-Fe Inorganic materials 0.000 claims description 7
- 229910052742 iron Inorganic materials 0.000 claims description 5
- 239000002243 precursor Substances 0.000 claims description 5
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 4
- 239000011575 calcium Substances 0.000 claims description 4
- 238000013021 overheating Methods 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 229910052791 calcium Inorganic materials 0.000 claims description 3
- 235000014106 fortified food Nutrition 0.000 claims description 3
- 239000012535 impurity Substances 0.000 claims description 3
- 235000013305 food Nutrition 0.000 claims 17
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 5
- 229910002651 NO3 Inorganic materials 0.000 claims 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims 4
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims 2
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims 2
- 229910052759 nickel Inorganic materials 0.000 claims 2
- 229910052698 phosphorus Inorganic materials 0.000 claims 2
- 239000011574 phosphorus Substances 0.000 claims 2
- 239000011701 zinc Substances 0.000 claims 2
- 229910052725 zinc Inorganic materials 0.000 claims 2
- 241001026509 Kata Species 0.000 claims 1
- 230000008569 process Effects 0.000 abstract description 23
- 239000000126 substance Substances 0.000 abstract description 6
- 230000000694 effects Effects 0.000 abstract 2
- 230000003993 interaction Effects 0.000 abstract 1
- 150000001299 aldehydes Chemical class 0.000 description 36
- 239000003921 oil Substances 0.000 description 32
- 239000000047 product Substances 0.000 description 28
- 150000001875 compounds Chemical class 0.000 description 23
- 239000000203 mixture Substances 0.000 description 23
- 238000010521 absorption reaction Methods 0.000 description 20
- 238000010791 quenching Methods 0.000 description 17
- 239000002904 solvent Substances 0.000 description 11
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 10
- 239000007788 liquid Substances 0.000 description 10
- 229910052751 metal Inorganic materials 0.000 description 10
- 239000002184 metal Substances 0.000 description 10
- 239000007795 chemical reaction product Substances 0.000 description 9
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 8
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 8
- 229910044991 metal oxide Inorganic materials 0.000 description 7
- 150000004706 metal oxides Chemical class 0.000 description 7
- 238000012545 processing Methods 0.000 description 7
- 239000006096 absorbing agent Substances 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- 238000009826 distribution Methods 0.000 description 6
- 150000002739 metals Chemical class 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 230000008859 change Effects 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 238000010586 diagram Methods 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 150000001336 alkenes Chemical class 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 230000006378 damage Effects 0.000 description 4
- -1 dehydrogenated C 4 hydrocarbons Chemical class 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 239000007791 liquid phase Substances 0.000 description 4
- AMWRITDGCCNYAT-UHFFFAOYSA-L manganese oxide Inorganic materials [Mn].O[Mn]=O.O[Mn]=O AMWRITDGCCNYAT-UHFFFAOYSA-L 0.000 description 4
- 239000003345 natural gas Substances 0.000 description 4
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 238000012546 transfer Methods 0.000 description 4
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000004939 coking Methods 0.000 description 3
- 238000007872 degassing Methods 0.000 description 3
- 150000001993 dienes Chemical class 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 239000003595 mist Substances 0.000 description 3
- 150000002894 organic compounds Chemical class 0.000 description 3
- 238000012856 packing Methods 0.000 description 3
- 238000005191 phase separation Methods 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical group CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 229910001308 Zinc ferrite Inorganic materials 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical compound C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- VSGNNIFQASZAOI-UHFFFAOYSA-L calcium acetate Chemical compound [Ca+2].CC([O-])=O.CC([O-])=O VSGNNIFQASZAOI-UHFFFAOYSA-L 0.000 description 2
- 239000001639 calcium acetate Substances 0.000 description 2
- 229960005147 calcium acetate Drugs 0.000 description 2
- 235000011092 calcium acetate Nutrition 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 150000001728 carbonyl compounds Chemical class 0.000 description 2
- 239000012876 carrier material Substances 0.000 description 2
- 238000005266 casting Methods 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 238000005194 fractionation Methods 0.000 description 2
- 239000012634 fragment Substances 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 235000013980 iron oxide Nutrition 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
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 239000011572 manganese Substances 0.000 description 2
- 150000005673 monoalkenes Chemical class 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000005201 scrubbing Methods 0.000 description 2
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- 229910052720 vanadium Inorganic materials 0.000 description 2
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 2
- WGEATSXPYVGFCC-UHFFFAOYSA-N zinc ferrite Chemical compound O=[Zn].O=[Fe]O[Fe]=O WGEATSXPYVGFCC-UHFFFAOYSA-N 0.000 description 2
- 229910052726 zirconium Inorganic materials 0.000 description 2
- BBDKZWKEPDTENS-UHFFFAOYSA-N 4-Vinylcyclohexene Chemical compound C=CC1CCC=CC1 BBDKZWKEPDTENS-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-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
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 1
- 239000005751 Copper oxide Substances 0.000 description 1
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 229910052768 actinide Inorganic materials 0.000 description 1
- 150000001255 actinides Chemical class 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 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
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
- 229910001863 barium hydroxide Inorganic materials 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- WFYPICNXBKQZGB-UHFFFAOYSA-N butenyne Chemical group C=CC#C WFYPICNXBKQZGB-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 229940043430 calcium compound Drugs 0.000 description 1
- 150000001674 calcium compounds Chemical class 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229910000431 copper oxide Inorganic materials 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000000407 epitaxy Methods 0.000 description 1
- LDLDYFCCDKENPD-UHFFFAOYSA-N ethenylcyclohexane Chemical compound C=CC1CCCCC1 LDLDYFCCDKENPD-UHFFFAOYSA-N 0.000 description 1
- 238000000895 extractive distillation Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 1
- 229910052735 hafnium Inorganic materials 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000002638 heterogeneous catalyst Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- VBMVTYDPPZVILR-UHFFFAOYSA-N iron(2+);oxygen(2-) Chemical class [O-2].[Fe+2] VBMVTYDPPZVILR-UHFFFAOYSA-N 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 150000002602 lanthanoids Chemical class 0.000 description 1
- 229910052746 lanthanum Inorganic materials 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 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
- 230000007257 malfunction Effects 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- PPNAOCWZXJOHFK-UHFFFAOYSA-N manganese(2+);oxygen(2-) Chemical class [O-2].[Mn+2] PPNAOCWZXJOHFK-UHFFFAOYSA-N 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 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
- 229910000480 nickel oxide Inorganic materials 0.000 description 1
- 229910052758 niobium Inorganic materials 0.000 description 1
- 239000010955 niobium Substances 0.000 description 1
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- GNRSAWUEBMWBQH-UHFFFAOYSA-N oxonickel Chemical compound [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- CHWRSCGUEQEHOH-UHFFFAOYSA-N potassium oxide Chemical compound [O-2].[K+].[K+] CHWRSCGUEQEHOH-UHFFFAOYSA-N 0.000 description 1
- 229910001950 potassium oxide Inorganic materials 0.000 description 1
- UMPKMCDVBZFQOK-UHFFFAOYSA-N potassium;iron(3+);oxygen(2-) Chemical compound [O-2].[O-2].[K+].[Fe+3] UMPKMCDVBZFQOK-UHFFFAOYSA-N 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 229910052706 scandium Inorganic materials 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910001923 silver oxide Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052596 spinel Inorganic materials 0.000 description 1
- 239000011029 spinel Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 229910001866 strontium hydroxide Inorganic materials 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 239000012855 volatile organic compound Substances 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Images
Classifications
-
- 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
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/24—Stationary reactors without moving elements inside
-
- 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
- C07C5/02—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation
- C07C5/08—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation of carbon-to-carbon triple bonds
- C07C5/09—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation of carbon-to-carbon triple bonds to carbon-to-carbon double bonds
-
- 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
- C07C5/42—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with a hydrogen acceptor
- C07C5/48—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with a hydrogen acceptor with oxygen as an acceptor
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/005—Processes comprising at least two steps in series
-
- 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
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00049—Controlling or regulating processes
- B01J2219/00051—Controlling the temperature
- B01J2219/00074—Controlling the temperature by indirect heating or cooling employing heat exchange fluids
- B01J2219/00087—Controlling the temperature by indirect heating or cooling employing heat exchange fluids with heat exchange elements outside the reactor
- B01J2219/00103—Controlling the temperature by indirect heating or cooling employing heat exchange fluids with heat exchange elements outside the reactor in a heat exchanger separate from the reactor
-
- 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
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/24—Stationary reactors without moving elements inside
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/84—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/889—Manganese, technetium or rhenium
- B01J23/8892—Manganese
-
- 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
- B01J2523/00—Constitutive chemical elements of heterogeneous catalysts
-
- 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
- B01J27/187—Phosphorus; Compounds thereof with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium with manganese, technetium or rhenium
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
- C07C2523/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of the iron group metals or copper
- C07C2523/74—Iron group metals
- C07C2523/745—Iron
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
- C07C2523/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of the iron group metals or copper
- C07C2523/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups C07C2523/02 - C07C2523/36
- C07C2523/80—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups C07C2523/02 - C07C2523/36 with zinc, cadmium or mercury
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- C07C2527/14—Phosphorus; Compounds thereof
- C07C2527/185—Phosphorus; Compounds thereof with iron group metals or platinum group metals
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Water Supply & Treatment (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261617535P | 2012-03-29 | 2012-03-29 | |
| US201261617506P | 2012-03-29 | 2012-03-29 | |
| US61/617,506 | 2012-03-29 | ||
| US61/617,535 | 2012-03-29 | ||
| PCT/US2013/034215 WO2013148913A1 (en) | 2012-03-29 | 2013-03-28 | Improved controllability oxidative dehydrogenation process for producing butadiene |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2014143515A RU2014143515A (ru) | 2016-05-20 |
| RU2628519C2 true RU2628519C2 (ru) | 2017-08-17 |
Family
ID=49261226
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2014143514A RU2619114C2 (ru) | 2012-03-29 | 2013-03-28 | Способ окислительного дегидрирования с низкими выбросами для получения бутадиена |
| RU2014143515A RU2628519C2 (ru) | 2012-03-29 | 2013-03-28 | Способ окислительного дегидрирования с улучшенной регулируемостью для получения бутадиена |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2014143514A RU2619114C2 (ru) | 2012-03-29 | 2013-03-28 | Способ окислительного дегидрирования с низкими выбросами для получения бутадиена |
Country Status (11)
| Country | Link |
|---|---|
| US (3) | US9908097B2 (enExample) |
| EP (2) | EP2831021B1 (enExample) |
| JP (2) | JP6157585B2 (enExample) |
| KR (2) | KR102051168B1 (enExample) |
| CN (2) | CN104507894B (enExample) |
| CA (2) | CA2867635A1 (enExample) |
| MX (2) | MX366150B (enExample) |
| MY (1) | MY166545A (enExample) |
| RU (2) | RU2619114C2 (enExample) |
| SG (2) | SG11201405984TA (enExample) |
| WO (2) | WO2013148908A1 (enExample) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2867635A1 (en) | 2012-03-29 | 2013-10-03 | Tpc Group Llc | Low emissions oxidative dehydrogenation process for producing butadiene |
| KR101676531B1 (ko) * | 2013-11-21 | 2016-11-15 | 주식회사 엘지화학 | 부타디엔 제조 공정 내 에너지 재활용 방법 |
| US10035136B2 (en) | 2014-03-25 | 2018-07-31 | Tpc Group Llc | Catalyst for reduced nitrogen oxide (NOx) emissions in an oxodehydrogenation process |
| KR101784047B1 (ko) | 2014-07-02 | 2017-10-10 | 주식회사 엘지화학 | 부타디엔 제조 공정 내 에너지 재활용 방법 |
| KR101782675B1 (ko) * | 2014-07-02 | 2017-09-27 | 주식회사 엘지화학 | 부타디엔 제조 공정 내 에너지 재활용 방법 |
| KR101782674B1 (ko) * | 2014-07-02 | 2017-09-27 | 주식회사 엘지화학 | 부타디엔 제조 공정 내 에너지 재활용 방법 |
| KR101784046B1 (ko) * | 2014-07-02 | 2017-10-10 | 주식회사 엘지화학 | 부타디엔 제조 공정 내 에너지 재활용 방법 |
| WO2016151008A1 (de) * | 2015-03-26 | 2016-09-29 | Basf Se | Verfahren zur herstellung von 1,3-butadien aus n-butenen durch oxidative dehydrierung |
| FR3040703B1 (fr) * | 2015-09-03 | 2017-10-06 | Ifp Energies Now | Procede integre de production de butadiene a partir de butanol |
| RU2674664C1 (ru) * | 2015-09-25 | 2018-12-12 | Юоп Ллк | Способы и установки для производства бутадиена |
| KR102088494B1 (ko) * | 2015-11-06 | 2020-03-13 | 유오피 엘엘씨 | 부타디엔 제조 목적으로 알데히드를 스트리핑하기 위한 c4 흡수기 오버헤드의 사용 |
| MX390283B (es) * | 2015-11-06 | 2025-03-20 | Uop Llc | Recuperación de calor en el proceso de producción de butadieno. |
| WO2018095776A1 (de) | 2016-11-22 | 2018-05-31 | Basf Se | Verfahren zur herstellung von 1,3-butadien aus n-butenen durch oxidative dehydrierung umfassend eine wässrige wäsche des c4-produktgasstroms |
| WO2018095856A1 (de) | 2016-11-22 | 2018-05-31 | Basf Se | Verfahren zur herstellung von 1,3-butadien aus n-butenen durch oxidative dehydrierung umfassend eine methacrolein-abtrennung bei der aufarbeitung |
| EP3323797A1 (de) | 2016-11-22 | 2018-05-23 | Basf Se | Verfahren zur herstellung von 1,3-butadien aus n-butenen durch oxidative dehydrierung umfassend eine saure wäsche des c4-produktgasstroms |
| KR102224278B1 (ko) | 2017-04-12 | 2021-03-08 | 주식회사 엘지화학 | 산화적 탈수소화 반응용 촉매 시스템, 이를 포함하는 산화적 탈수소화용 반응기 및 산화적 탈수소화 방법 |
| US10543470B2 (en) * | 2017-04-28 | 2020-01-28 | Intramicron, Inc. | Reactors and methods for processes involving partial oxidation reactions |
| WO2018234158A1 (de) | 2017-06-19 | 2018-12-27 | Basf Se | Verfahren zur herstellung von 1,3-butadien aus n-butenen durch oxidative dehydrierung umfassend eine wäsche des c4-produktgasstroms |
| JP7137920B2 (ja) * | 2017-11-02 | 2022-09-15 | 旭化成株式会社 | ブタジエンの製造方法 |
| KR102262896B1 (ko) * | 2017-11-30 | 2021-06-09 | 주식회사 엘지화학 | 산화적 탈수소화 반응용 촉매 시스템, 이를 포함하는 부타디엔 제조용 반응기 및 1,3-부타디엔의 제조방법 |
| CN110066212B (zh) * | 2018-01-22 | 2022-04-01 | 惠生工程（中国）有限公司 | 一种甲醇制烯烃工艺副产碳四烯烃氧化脱氢制丁二烯工艺 |
| KR102564959B1 (ko) * | 2018-08-23 | 2023-08-07 | 주식회사 엘지화학 | 1,3-부타디엔의 제조방법 |
| CN110237788B (zh) * | 2019-05-28 | 2020-05-05 | 宁波浙铁江宁化工有限公司 | 一种顺酐反应系统在线检测工艺及设备 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2093792A5 (enExample) * | 1970-05-27 | 1972-01-28 | Petro Tex Chem Corp | |
| US4658080A (en) * | 1974-02-19 | 1987-04-14 | Petro-Tex Chemical Corporation | Acetylene removal process |
| SU1216938A1 (ru) * | 1984-08-13 | 1999-10-20 | А.Л. Цайлингольд | Способ получения бутадиена |
Family Cites Families (60)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2444035A (en) * | 1943-12-31 | 1948-06-29 | Koppers Co Inc | Process for dehydrogenating hydrocarbons using as catalyst calcium oxide on calcium carbonate |
| US3159588A (en) * | 1960-06-15 | 1964-12-01 | Union Oil Co | Silica-zirconia-titania hydrocracking catalyst |
| US3207805A (en) | 1960-06-17 | 1965-09-21 | Petro Tex Chem Corp | Dehydrogenation in the presence of oxygen and an ammonium halide |
| BE615317A (enExample) * | 1961-03-22 | |||
| US3110746A (en) * | 1961-05-26 | 1963-11-12 | Shell Oil Co | Oxidative dehydrogenation of monoolefins |
| US3320330A (en) * | 1962-04-25 | 1967-05-16 | Standard Oil Co | Process for the catalytic oxidative dehydrogenation of olefins to diolefins |
| US3284536A (en) | 1964-01-02 | 1966-11-08 | Petro Tex Chem Corp | Dehydrogenation with magnesium ferrite |
| US4658074A (en) | 1965-05-28 | 1987-04-14 | Petro-Tex Chemical Corporation | Catalytic oxidative dehydrogenation process |
| US3322847A (en) * | 1965-09-02 | 1967-05-30 | Standard Oil Co | Oxidative dehydrogenation of monoolefins |
| US3496070A (en) | 1967-11-09 | 1970-02-17 | Petro Tex Chem Corp | Purification of unsaturated hydrocarbons by extractive distillation with addition of liquid solvent to stripper overhead |
| US3937746A (en) | 1969-09-19 | 1976-02-10 | Petro-Tex Chemical Corporation | Sulfur promoted oxidative dehydrogenation |
| US3849511A (en) * | 1970-10-07 | 1974-11-19 | Petro Tex Chem Corp | Oxidative dehydrogenation with manganese ferrite catalyst |
| US3745194A (en) | 1970-10-16 | 1973-07-10 | Phillips Petroleum Co | Oxidative dehydrogenation of paraffinic hydrocarbons |
| US3674887A (en) * | 1970-12-24 | 1972-07-04 | Phillips Petroleum Co | Oxidative dehydrogenation process |
| JPS495321B1 (enExample) * | 1970-12-25 | 1974-02-06 | ||
| US3801670A (en) * | 1970-12-25 | 1974-04-02 | Sumitomo Chemical Co | Catalytic process for the production of diolefins |
| US3828202A (en) | 1971-07-06 | 1974-08-06 | Burroughs Corp | Logic circuit using a current switch to compensate for signal deterioration |
| US3828101A (en) * | 1971-08-26 | 1974-08-06 | Petro Tex Chem Corp | Method of preparation of ferrite catalysts |
| BE794908A (fr) | 1972-02-03 | 1973-08-02 | Petro Tex Chem Corp | Purification de composes insatures |
| US3900525A (en) * | 1972-05-16 | 1975-08-19 | Petro Tex Chem Corp | Manganese ferrite catalyzed oxidative dehydrogenation |
| US3801671A (en) | 1972-05-30 | 1974-04-02 | Phillips Petroleum Co | Oxidative dehydrogenation of organic compounds |
| US4021500A (en) * | 1972-09-13 | 1977-05-03 | Phillips Petroleum Company | Oxidative dehydrogenation system |
| US3887631A (en) | 1973-05-14 | 1975-06-03 | Texaco Inc | Oxidative dehydrogenation of hydrocarbons |
| US4644088A (en) * | 1974-02-19 | 1987-02-17 | Petro-Tex Chemical Corporation | Acetylene removal process |
| CA1034148A (en) * | 1974-02-19 | 1978-07-04 | Petro-Tex Chemical Corporation | Acetylene removal process |
| US3943185A (en) | 1974-05-28 | 1976-03-09 | Petro-Tex Chemical Corporation | Diolefin production and purification |
| US3960767A (en) * | 1974-09-03 | 1976-06-01 | Petro-Tex Chemical Corporation | Modified zinc ferrite oxidative dehydrogenation catalysts |
| US3953370A (en) | 1974-10-16 | 1976-04-27 | Petro-Tex Chemical Corporation | Method of activating zinc ferrite oxidative dehydrogenation catalysts |
| US4083884A (en) * | 1976-07-19 | 1978-04-11 | Petro-Tex Chemical Corporation | Calcium oxide modified zinc ferrite oxidative dehydrogenation catalysts and use |
| US4067921A (en) * | 1976-12-06 | 1978-01-10 | The Dow Chemical Company | Primary adjunct, continuous diene process |
| FR2444019A1 (fr) * | 1978-12-15 | 1980-07-11 | Inst Neftekhimicheskikh Prot | Procede de preparation de butadiene-1,3 |
| US4266086A (en) | 1980-02-12 | 1981-05-05 | The B. F. Goodrich Company | Process for removing α-acetylenes from diolefins |
| JPS5879932A (ja) * | 1981-11-06 | 1983-05-13 | Japan Synthetic Rubber Co Ltd | ブタジエン又はイソプレンの精製方法 |
| US4479025A (en) * | 1982-11-22 | 1984-10-23 | Uop Inc. | Alkylaromatic hydrocarbon dehydrogenation process |
| JPS60126235A (ja) * | 1983-12-14 | 1985-07-05 | Nippon Zeon Co Ltd | ブタジエンの製造方法 |
| US4595788A (en) * | 1983-11-25 | 1986-06-17 | Nippon Zeon Co. Ltd. | Process for producing butadiene |
| US4740334A (en) | 1987-05-29 | 1988-04-26 | Norton Company | Tower packing element with embossed surfaces |
| FR2630662A1 (fr) | 1988-04-29 | 1989-11-03 | Shell Int Research | Catalyseur pour la deshydrogenation de composes organiques, procede pour sa preparation et son utilisation |
| US4973793A (en) | 1989-06-08 | 1990-11-27 | Texas Petrochemicals Corporation | Oxidative dehydrogenation of amylenes |
| JP3371112B2 (ja) | 1990-09-18 | 2003-01-27 | ダイヤニトリックス株式会社 | 鉄・アンチモン含有金属酸化物触媒組成物およびその製法 |
| US5214225A (en) * | 1991-12-05 | 1993-05-25 | Hall Stephen G | Dehydrogenation process with improved heat recovery |
| US5772898A (en) | 1994-12-21 | 1998-06-30 | Uop Llc | Hydrocarbon conversion process using novel metallo manganese oxides |
| US6403523B1 (en) | 2000-09-18 | 2002-06-11 | Union Carbide Chemicals & Plastics Technology Corporation | Catalysts for the oxidative dehydrogenation of hydrocarbons |
| CA2500867A1 (en) | 2002-10-03 | 2004-04-15 | Koch-Glitsch, Lp | Structured packing plate and element and method of fabricating same |
| US7402720B2 (en) | 2002-12-19 | 2008-07-22 | Exxonmobil Chemical Patents Inc. | Distillation process for removal of methyl acetylene and/or propadiene from an olefin stream |
| US7205447B2 (en) | 2002-12-23 | 2007-04-17 | Exxonmobil Chemical Patents Inc. | Process for removing aldehydes and/or ketones from an olefinic stream |
| DE10361822A1 (de) * | 2003-12-30 | 2005-08-11 | Basf Ag | Verfahren zur Herstellung von Butadien |
| DE102004061514A1 (de) * | 2004-12-21 | 2006-07-06 | Basf Ag | Verfahren zur Herstellung von Butadien aus n-Butan |
| DE102005002127A1 (de) * | 2005-01-17 | 2006-07-20 | Basf Ag | Verfahren zur Herstellung von Butadien aus n-Butan |
| DE102006029790A1 (de) * | 2006-06-27 | 2008-01-03 | Basf Ag | Verfahren der kontinuierlichen heterogen katalysierten partiellen Dehydrierung wenigstens eines zu dehydrierenden Kohlenwasserstoffs |
| KR100847206B1 (ko) | 2007-05-10 | 2008-07-17 | 에스케이에너지 주식회사 | 아연 페라이트 촉매, 이의 제조방법 및 이를 이용한1,3-부타디엔의 제조방법 |
| KR101508776B1 (ko) * | 2008-03-28 | 2015-04-10 | 에스케이이노베이션 주식회사 | 연속 흐름식 2중 촉매 반응 장치를 이용하여노르말-부텐으로부터 1,3-부타디엔을 제조하는 방법 |
| EP2288583A1 (en) * | 2008-04-09 | 2011-03-02 | Shell Internationale Research Maatschappij B.V. | A method of improving a dehydrogenation process |
| US20110245568A1 (en) | 2008-07-22 | 2011-10-06 | Fina Technology, Inc. | Dehydrogenation Reactions of N-Butene to Butadiene |
| JP5272657B2 (ja) * | 2008-10-31 | 2013-08-28 | 三菱化学株式会社 | プレート式反応器を用いた反応生成物の製造方法 |
| EP2417091A1 (en) * | 2009-04-10 | 2012-02-15 | University Of Southern California | Rendering natural gas as an environmentally carbon dioxide neutral fuel and a regenerative carbon source |
| CA2763317C (en) * | 2009-05-29 | 2016-12-20 | Mitsubishi Chemical Corporation | Production process of conjugated diene |
| JP5652151B2 (ja) | 2009-12-21 | 2015-01-14 | 三菱化学株式会社 | 共役ジエンの製造方法 |
| KR101713328B1 (ko) * | 2010-07-20 | 2017-03-08 | 에스케이이노베이션 주식회사 | 혼성 망간 페라이트가 코팅된 촉매, 이의 제조방법 및 이를 이용한 1,3-부타디엔의 제조방법 |
| CA2867635A1 (en) * | 2012-03-29 | 2013-10-03 | Tpc Group Llc | Low emissions oxidative dehydrogenation process for producing butadiene |
-
2013
- 2013-03-28 CA CA2867635A patent/CA2867635A1/en not_active Abandoned
- 2013-03-28 SG SG11201405984TA patent/SG11201405984TA/en unknown
- 2013-03-28 KR KR1020147030267A patent/KR102051168B1/ko active Active
- 2013-03-28 JP JP2015503552A patent/JP6157585B2/ja active Active
- 2013-03-28 MX MX2014011659A patent/MX366150B/es active IP Right Grant
- 2013-03-28 CN CN201380027362.3A patent/CN104507894B/zh active Active
- 2013-03-28 US US14/386,550 patent/US9908097B2/en active Active
- 2013-03-28 KR KR1020147030264A patent/KR102036398B1/ko active Active
- 2013-03-28 EP EP13768548.3A patent/EP2831021B1/en active Active
- 2013-03-28 WO PCT/US2013/034205 patent/WO2013148908A1/en not_active Ceased
- 2013-03-28 RU RU2014143514A patent/RU2619114C2/ru active
- 2013-03-28 RU RU2014143515A patent/RU2628519C2/ru active
- 2013-03-28 MX MX2014011658A patent/MX363244B/es unknown
- 2013-03-28 EP EP13769936.9A patent/EP2831022B1/en active Active
- 2013-03-28 SG SG11201405986VA patent/SG11201405986VA/en unknown
- 2013-03-28 JP JP2015503555A patent/JP6157586B2/ja active Active
- 2013-03-28 WO PCT/US2013/034215 patent/WO2013148913A1/en not_active Ceased
- 2013-03-28 US US14/386,617 patent/US9650316B2/en active Active
- 2013-03-28 CA CA2870209A patent/CA2870209A1/en not_active Abandoned
- 2013-03-28 MY MYPI2014002729A patent/MY166545A/en unknown
- 2013-03-28 CN CN201380027030.5A patent/CN104321294B/zh active Active
-
2017
- 2017-04-11 US US15/484,247 patent/US10052608B2/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2093792A5 (enExample) * | 1970-05-27 | 1972-01-28 | Petro Tex Chem Corp | |
| US4658080A (en) * | 1974-02-19 | 1987-04-14 | Petro-Tex Chemical Corporation | Acetylene removal process |
| SU1216938A1 (ru) * | 1984-08-13 | 1999-10-20 | А.Л. Цайлингольд | Способ получения бутадиена |
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| RU2628519C2 (ru) | Способ окислительного дегидрирования с улучшенной регулируемостью для получения бутадиена | |
| KR101188502B1 (ko) | 프로판으로부터 아크롤레인, 아크릴산, 또는 이들의혼합물의 제조 방법 | |
| RU2346928C2 (ru) | Способ получения, по меньшей мере, одного продукта частичного окисления и/или аммокисления пропилена | |
| KR101462049B1 (ko) | 프로판으로부터 아크롤레인 또는 아크릴산 또는 이의 혼합물을 제조하는 방법 | |
| JPH03501483A (ja) | プロセス | |
| JP6070825B2 (ja) | １，３−ブタジエンの製造方法 | |
| JP2011132218A (ja) | 共役ジエンの製造方法 | |
| JPWO2014168051A1 (ja) | １，３−ブタジエンの製造方法 | |
| JP6405857B2 (ja) | 共役ジエンの製造方法 | |
| EA009812B1 (ru) | Способ получения олефинов | |
| HK1204321B (en) | Improved controllability oxidative dehydrogenation process for producing butadiene | |
| JP2011241208A (ja) | 共役ジエンの製造方法 | |
| JP2012046509A (ja) | 共役ジエンの製造方法 | |
| US20180258008A1 (en) | Integrated method for producing butadiene from butanol |