DK2925706T3 - METHOD OF LOW ENERGY CONSUMPTION FOR DEHYDRATION OF ETHANOL TO ETHYLENE - Google Patents
METHOD OF LOW ENERGY CONSUMPTION FOR DEHYDRATION OF ETHANOL TO ETHYLENE Download PDFInfo
- Publication number
- DK2925706T3 DK2925706T3 DK13803148.9T DK13803148T DK2925706T3 DK 2925706 T3 DK2925706 T3 DK 2925706T3 DK 13803148 T DK13803148 T DK 13803148T DK 2925706 T3 DK2925706 T3 DK 2925706T3
- Authority
- DK
- Denmark
- Prior art keywords
- feedstock
- ethanol
- effluent
- dehydration
- mpa
- Prior art date
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 title claims description 361
- 238000006297 dehydration reaction Methods 0.000 title claims description 79
- 238000000034 method Methods 0.000 title claims description 74
- 230000018044 dehydration Effects 0.000 title claims description 67
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 title claims description 51
- 239000005977 Ethylene Substances 0.000 title claims description 48
- 238000005265 energy consumption Methods 0.000 title description 8
- 230000008569 process Effects 0.000 claims description 63
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 52
- 239000003054 catalyst Substances 0.000 claims description 45
- 230000002378 acidificating effect Effects 0.000 claims description 20
- 239000007787 solid Substances 0.000 claims description 18
- 239000010457 zeolite Substances 0.000 claims description 17
- 238000000746 purification Methods 0.000 claims description 15
- GNFTZDOKVXKIBK-UHFFFAOYSA-N 3-(2-methoxyethoxy)benzohydrazide Chemical compound COCCOC1=CC=CC(C(=O)NN)=C1 GNFTZDOKVXKIBK-UHFFFAOYSA-N 0.000 claims description 14
- 238000004064 recycling Methods 0.000 claims description 13
- FGUUSXIOTUKUDN-IBGZPJMESA-N C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 Chemical compound C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 FGUUSXIOTUKUDN-IBGZPJMESA-N 0.000 claims description 12
- 238000011144 upstream manufacturing Methods 0.000 claims description 11
- 229910021536 Zeolite Inorganic materials 0.000 claims description 10
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 239000003377 acid catalyst Substances 0.000 claims description 7
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- 238000001704 evaporation Methods 0.000 claims description 3
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- 235000019441 ethanol Nutrition 0.000 description 115
- 230000008016 vaporization Effects 0.000 description 58
- 238000009834 vaporization Methods 0.000 description 51
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 46
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- 238000006243 chemical reaction Methods 0.000 description 30
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
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- 239000011159 matrix material Substances 0.000 description 7
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- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 125000002091 cationic group Chemical group 0.000 description 6
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- 150000001298 alcohols Chemical class 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
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- 230000002829 reductive effect Effects 0.000 description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
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- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- -1 sulphated zirconias Substances 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 239000005864 Sulphur Substances 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000000571 coke Substances 0.000 description 2
- 238000002485 combustion reaction Methods 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 230000009849 deactivation Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
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- 229920003303 ion-exchange polymer Polymers 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
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- 230000003472 neutralizing effect Effects 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 235000011007 phosphoric acid Nutrition 0.000 description 2
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- 238000004313 potentiometry Methods 0.000 description 2
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- 238000001179 sorption measurement Methods 0.000 description 2
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- 229960004793 sucrose Drugs 0.000 description 2
- 235000000346 sugar Nutrition 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- VTPNYMSKBPZSTF-UHFFFAOYSA-N 1-ethenyl-2-ethylbenzene Chemical compound CCC1=CC=CC=C1C=C VTPNYMSKBPZSTF-UHFFFAOYSA-N 0.000 description 1
- WAEOXIOXMKNFLQ-UHFFFAOYSA-N 1-methyl-4-prop-2-enylbenzene Chemical group CC1=CC=C(CC=C)C=C1 WAEOXIOXMKNFLQ-UHFFFAOYSA-N 0.000 description 1
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical compound C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 description 1
- ISRGONDNXBCDBM-UHFFFAOYSA-N 2-chlorostyrene Chemical compound ClC1=CC=CC=C1C=C ISRGONDNXBCDBM-UHFFFAOYSA-N 0.000 description 1
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241000269350 Anura Species 0.000 description 1
- 235000016068 Berberis vulgaris Nutrition 0.000 description 1
- 241000335053 Beta vulgaris Species 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 229930091371 Fructose Natural products 0.000 description 1
- 239000005715 Fructose Substances 0.000 description 1
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 1
- 108010068370 Glutens Proteins 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
- 239000004793 Polystyrene Substances 0.000 description 1
- 240000000111 Saccharum officinarum Species 0.000 description 1
- 235000007201 Saccharum officinarum Nutrition 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 description 1
- 150000004645 aluminates Chemical class 0.000 description 1
- ILRRQNADMUWWFW-UHFFFAOYSA-K aluminium phosphate Chemical class O1[Al]2OP1(=O)O2 ILRRQNADMUWWFW-UHFFFAOYSA-K 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 1
- 230000001174 ascending effect Effects 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000002551 biofuel Substances 0.000 description 1
- 229910052810 boron oxide Inorganic materials 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 230000006315 carbonylation Effects 0.000 description 1
- 238000005810 carbonylation reaction Methods 0.000 description 1
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- 235000013339 cereals Nutrition 0.000 description 1
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- 239000013078 crystal Substances 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- JKWMSGQKBLHBQQ-UHFFFAOYSA-N diboron trioxide Chemical compound O=BOB=O JKWMSGQKBLHBQQ-UHFFFAOYSA-N 0.000 description 1
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- 238000005516 engineering process Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- 238000011066 ex-situ storage Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 229960002737 fructose Drugs 0.000 description 1
- 229930182830 galactose Natural products 0.000 description 1
- 229960001031 glucose Drugs 0.000 description 1
- 235000021312 gluten Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000002029 lignocellulosic biomass Substances 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 238000005461 lubrication Methods 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 239000003345 natural gas Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- 125000001477 organic nitrogen group Chemical group 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
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- 239000002243 precursor Substances 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
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- 238000010517 secondary reaction Methods 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
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- 239000005720 sucrose Substances 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- JUWGUJSXVOBPHP-UHFFFAOYSA-B titanium(4+);tetraphosphate Chemical class [Ti+4].[Ti+4].[Ti+4].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O JUWGUJSXVOBPHP-UHFFFAOYSA-B 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- LEHFSLREWWMLPU-UHFFFAOYSA-B zirconium(4+);tetraphosphate Chemical class [Zr+4].[Zr+4].[Zr+4].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LEHFSLREWWMLPU-UHFFFAOYSA-B 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/20—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms
- C07C1/24—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms by elimination of water
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/09—Preparation of ethers by dehydration of compounds containing hydroxy groups
-
- 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
- C07C2527/16—Phosphorus; Compounds thereof containing oxygen
- C07C2527/167—Phosphates or other compounds comprising the anion (PnO3n+1)(n+2)-
- C07C2527/173—Phosphoric acid or other acids with the formula Hn+2PnO3n+1
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2529/00—Catalysts comprising molecular sieves
- C07C2529/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites, pillared clays
- C07C2529/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- C07C2529/40—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the pentasil type, e.g. types ZSM-5, ZSM-8 or ZSM-11
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2529/00—Catalysts comprising molecular sieves
- C07C2529/82—Phosphates
- C07C2529/84—Aluminophosphates containing other elements, e.g. metals, boron
- C07C2529/85—Silicoaluminophosphates (SAPO compounds)
-
- 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
- Y02P30/00—Technologies relating to oil refining and petrochemical industry
- Y02P30/40—Ethylene production
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Treatment Of Liquids With Adsorbents In General (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR1203201A FR2998568B1 (fr) | 2012-11-27 | 2012-11-27 | Procede de deshydratation de l'ethanol en ethylene a basse consommation |
| PCT/FR2013/052767 WO2014083260A1 (fr) | 2012-11-27 | 2013-11-18 | Procede de déshydratation de l'éthanol en éthylene a basse consommation énergétique |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DK2925706T3 true DK2925706T3 (en) | 2017-05-01 |
Family
ID=47594850
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK13803148.9T DK2925706T3 (en) | 2012-11-27 | 2013-11-18 | METHOD OF LOW ENERGY CONSUMPTION FOR DEHYDRATION OF ETHANOL TO ETHYLENE |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US9663414B2 (enExample) |
| EP (1) | EP2925706B1 (enExample) |
| JP (1) | JP6186444B2 (enExample) |
| KR (1) | KR102114515B1 (enExample) |
| CN (1) | CN104981447B (enExample) |
| BR (1) | BR112015011707B1 (enExample) |
| CA (1) | CA2891127C (enExample) |
| DK (1) | DK2925706T3 (enExample) |
| ES (1) | ES2623488T3 (enExample) |
| FR (1) | FR2998568B1 (enExample) |
| PL (1) | PL2925706T3 (enExample) |
| RU (1) | RU2641105C2 (enExample) |
| UA (1) | UA116224C2 (enExample) |
| WO (1) | WO2014083260A1 (enExample) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR3001969B1 (fr) * | 2013-02-12 | 2015-08-21 | IFP Energies Nouvelles | Procede de production d'oxyde d'ethylene a partir d'un flux d'ethanol thermiquement integre |
| FR3001968B1 (fr) * | 2013-02-12 | 2015-02-27 | IFP Energies Nouvelles | Procede de production d'oxyde d'ethylene a partir d'un flux d'ethanol thermo-mecaniquement integre |
| FR3026406B1 (fr) * | 2014-09-26 | 2016-12-09 | Ifp Energies Now | Procede de deshydratation isomerisante d'une charge alcool primaire substitue en position 2 par un groupement alkyl sur un catalyseur comprenant une zeolithe de type fer |
| FR3054219B1 (fr) | 2016-07-22 | 2018-08-03 | IFP Energies Nouvelles | Nouveaux procedes d'obtention de composes aromatiques a partir de composes furaniques et d'ethanol. |
| FR3089973B1 (fr) | 2018-12-14 | 2020-12-25 | Ifp Energies Now | Procédé de déshydratation de l'éthanol en éthylène à basse consommation énergétique |
| FR3090393B1 (fr) | 2018-12-20 | 2021-04-23 | Ifp Energies Now | Procédé de traitement d’une charge alcool pour la production d’oléfines |
| CN115322068B (zh) * | 2022-08-30 | 2023-03-28 | 天津大学 | 乙醇脱水制乙烯热耦合方法及装置 |
| US12435013B2 (en) | 2022-08-30 | 2025-10-07 | Uop Llc | Ethanol to ethylene process |
| WO2025058997A1 (en) * | 2023-09-11 | 2025-03-20 | Scientific Design Llc | Improved ethanol dehydration process |
| FR3153004A1 (fr) | 2023-09-15 | 2025-03-21 | Axens | Ensemble de collecte d'un fluide gazeux |
| FR3153613B1 (fr) | 2023-09-29 | 2025-10-10 | Ifp Energies Now | Procede de production de distillats moyens en particulier de kerosene a partir d’une charge alcoolique |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR7705256A (pt) | 1977-08-09 | 1979-04-03 | Petroleo Brasileiro Sa | Processo e preparacao de eteno |
| BR8101487A (pt) * | 1981-03-13 | 1982-10-26 | Petroleo Brasileiro Sa | Processo de desidratacao de um alcool de baixo peso molecular |
| JPH01163137A (ja) * | 1987-12-21 | 1989-06-27 | Jgc Corp | エタノールの脱水反応方法 |
| DE602006008619D1 (de) * | 2005-07-06 | 2009-10-01 | Bp Chem Int Ltd | Reaktive destillation zur dehydratisierung gemischter alkohole |
| BRPI0601803A (pt) | 2006-05-18 | 2008-02-19 | Helcio Valladares Barrocas | processo para produção de eteno a partir de álcool etìlico |
| MX2010008722A (es) | 2008-02-07 | 2010-11-30 | Total Petrochemicals Res Feluy | Deshidratacion de alcoholes en presencia de un componente inerte. |
| MX2010008723A (es) | 2008-02-07 | 2010-11-30 | Total Petrochemicals Res Feluy | Deshidratacion de alcoholes en silicatos cristalinos. |
| KR101227221B1 (ko) | 2008-02-07 | 2013-01-28 | 토탈 리서치 앤드 테크놀로지 펠루이 | 에탄올로부터의 올레핀의 제조 방법 |
| US20110137096A1 (en) | 2008-02-07 | 2011-06-09 | Total Petrochemicals Research Feluy | Process to Make Olefins from Ethanol |
| MX2011005459A (es) * | 2008-11-28 | 2011-06-16 | Total Petrochemicals Res Feluy | Purificacion de alcoholes antes de su uso en presencia de un catalizador acido. |
| CN102471198B (zh) | 2009-07-01 | 2015-03-11 | 陶氏环球技术有限责任公司 | 由脂族醇制备烯烃的工艺 |
| WO2011161045A1 (en) * | 2010-06-23 | 2011-12-29 | Total Petrochemicals Research Feluy | Dehydration of alcohols on poisoned acidic catalysts |
| FR2978146B1 (fr) * | 2011-07-21 | 2013-08-30 | IFP Energies Nouvelles | Procede de deshydratation de l'ethanol en ethylene a basse consommation energetique |
| TWI605868B (zh) * | 2012-09-14 | 2017-11-21 | Ｂｐ有限公司 | 醇類的處理（二） |
-
2012
- 2012-11-27 FR FR1203201A patent/FR2998568B1/fr not_active Expired - Fee Related
-
2013
- 2013-11-18 DK DK13803148.9T patent/DK2925706T3/en active
- 2013-11-18 CA CA2891127A patent/CA2891127C/fr active Active
- 2013-11-18 KR KR1020157016541A patent/KR102114515B1/ko active Active
- 2013-11-18 BR BR112015011707-4A patent/BR112015011707B1/pt active IP Right Grant
- 2013-11-18 EP EP13803148.9A patent/EP2925706B1/fr active Active
- 2013-11-18 WO PCT/FR2013/052767 patent/WO2014083260A1/fr not_active Ceased
- 2013-11-18 ES ES13803148.9T patent/ES2623488T3/es active Active
- 2013-11-18 CN CN201380061953.2A patent/CN104981447B/zh active Active
- 2013-11-18 US US14/646,877 patent/US9663414B2/en active Active
- 2013-11-18 JP JP2015543496A patent/JP6186444B2/ja active Active
- 2013-11-18 RU RU2015125580A patent/RU2641105C2/ru active
- 2013-11-18 PL PL13803148T patent/PL2925706T3/pl unknown
- 2013-11-18 UA UAA201506352A patent/UA116224C2/uk unknown
Also Published As
| Publication number | Publication date |
|---|---|
| RU2015125580A (ru) | 2017-01-10 |
| EP2925706A1 (fr) | 2015-10-07 |
| JP6186444B2 (ja) | 2017-08-23 |
| CA2891127C (fr) | 2021-03-23 |
| CA2891127A1 (fr) | 2014-06-05 |
| KR102114515B1 (ko) | 2020-05-25 |
| JP2015535528A (ja) | 2015-12-14 |
| BR112015011707B1 (pt) | 2020-12-01 |
| PL2925706T3 (pl) | 2017-07-31 |
| ES2623488T3 (es) | 2017-07-11 |
| KR20150088293A (ko) | 2015-07-31 |
| CN104981447B (zh) | 2018-02-02 |
| EP2925706B1 (fr) | 2017-02-01 |
| UA116224C2 (uk) | 2018-02-26 |
| CN104981447A (zh) | 2015-10-14 |
| US20150299068A1 (en) | 2015-10-22 |
| BR112015011707A2 (pt) | 2017-07-11 |
| FR2998568B1 (fr) | 2015-01-23 |
| RU2641105C2 (ru) | 2018-01-16 |
| FR2998568A1 (fr) | 2014-05-30 |
| US9663414B2 (en) | 2017-05-30 |
| WO2014083260A1 (fr) | 2014-06-05 |
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