JP6464105B2 - 一体型膜反応器を用いたオレフィン水和プロセス - Google Patents
一体型膜反応器を用いたオレフィン水和プロセス Download PDFInfo
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- JP6464105B2 JP6464105B2 JP2016011848A JP2016011848A JP6464105B2 JP 6464105 B2 JP6464105 B2 JP 6464105B2 JP 2016011848 A JP2016011848 A JP 2016011848A JP 2016011848 A JP2016011848 A JP 2016011848A JP 6464105 B2 JP6464105 B2 JP 6464105B2
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- 239000012528 membrane Substances 0.000 title claims description 93
- 150000001336 alkenes Chemical class 0.000 title claims description 72
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 title claims description 48
- 238000006703 hydration reaction Methods 0.000 title claims description 24
- 238000000034 method Methods 0.000 title claims description 24
- 230000008569 process Effects 0.000 title claims description 23
- 230000036571 hydration Effects 0.000 title claims description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 51
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 49
- 238000006243 chemical reaction Methods 0.000 claims description 45
- 239000012466 permeate Substances 0.000 claims description 30
- 239000003054 catalyst Substances 0.000 claims description 26
- 239000000047 product Substances 0.000 claims description 20
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims description 19
- 238000000926 separation method Methods 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 17
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 14
- 230000004907 flux Effects 0.000 claims description 12
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical group CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 10
- 239000007789 gas Substances 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 239000012530 fluid Substances 0.000 claims description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 3
- 229910052786 argon Inorganic materials 0.000 claims description 2
- 239000001307 helium Substances 0.000 claims description 2
- 229910052734 helium Inorganic materials 0.000 claims description 2
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 claims description 2
- 230000000887 hydrating effect Effects 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 238000010408 sweeping Methods 0.000 claims 2
- 239000002253 acid Substances 0.000 description 9
- 238000012360 testing method Methods 0.000 description 8
- 150000001298 alcohols Chemical class 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 239000000376 reactant Substances 0.000 description 7
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- 239000012465 retentate Substances 0.000 description 6
- 239000011949 solid catalyst Substances 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 239000010457 zeolite Substances 0.000 description 5
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 229920005597 polymer membrane Polymers 0.000 description 4
- 229910021536 Zeolite Inorganic materials 0.000 description 3
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 3
- 238000006555 catalytic reaction Methods 0.000 description 3
- 239000003729 cation exchange resin Substances 0.000 description 3
- 229940023913 cation exchange resins Drugs 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 3
- 238000005373 pervaporation Methods 0.000 description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 239000000126 substance 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
- -1 PTMSP Polymers 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 239000003456 ion exchange resin Substances 0.000 description 2
- 229920003303 ion-exchange polymer Polymers 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000002033 PVDF binder Substances 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000013590 bulk material Substances 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000004231 fluid catalytic cracking Methods 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 230000009972 noncorrosive effect Effects 0.000 description 1
- CXQXSVUQTKDNFP-UHFFFAOYSA-N octamethyltrisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C CXQXSVUQTKDNFP-UHFFFAOYSA-N 0.000 description 1
- 238000000614 phase inversion technique Methods 0.000 description 1
- 238000004987 plasma desorption mass spectroscopy Methods 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000004230 steam cracking Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000032258 transport Effects 0.000 description 1
- DCGLONGLPGISNX-UHFFFAOYSA-N trimethyl(prop-1-ynyl)silane Chemical compound CC#C[Si](C)(C)C DCGLONGLPGISNX-UHFFFAOYSA-N 0.000 description 1
- 238000004065 wastewater treatment Methods 0.000 description 1
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J8/00—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes
- B01J8/005—Separating solid material from the gas/liquid stream
- B01J8/006—Separating solid material from the gas/liquid stream by filtration
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J8/00—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes
- B01J8/008—Details of the reactor or of the particulate material; Processes to increase or to retard the rate of reaction
- B01J8/009—Membranes, e.g. feeding or removing reactants or products to or from the catalyst bed through a membrane
-
- 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
-
- 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
- B01J19/18—Stationary reactors having moving elements inside
- B01J19/1893—Membrane reactors
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J8/00—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes
- B01J8/02—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes with stationary particles, e.g. in fixed beds
- B01J8/0242—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes with stationary particles, e.g. in fixed beds the fluid flow within the bed being predominantly vertical
- B01J8/0257—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes with stationary particles, e.g. in fixed beds the fluid flow within the bed being predominantly vertical in a cylindrical annular shaped bed
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J8/00—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes
- B01J8/02—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes with stationary particles, e.g. in fixed beds
- B01J8/0278—Feeding reactive fluids
-
- 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
- C07C29/03—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by addition of hydroxy groups to unsaturated carbon-to-carbon bonds, e.g. with the aid of H2O2
- C07C29/04—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by addition of hydroxy groups to unsaturated carbon-to-carbon bonds, e.g. with the aid of H2O2 by hydration of carbon-to-carbon double bonds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
- B01D53/22—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by diffusion
-
- 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
- B01J2208/00—Processes carried out in the presence of solid particles; Reactors therefor
- B01J2208/00008—Controlling the process
- B01J2208/00017—Controlling the temperature
- B01J2208/00106—Controlling the temperature by indirect heat exchange
- B01J2208/00265—Part of all of the reactants being heated or cooled outside the reactor while recycling
- B01J2208/00274—Part of all of the reactants being heated or cooled outside the reactor while recycling involving reactant vapours
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Physics & Mathematics (AREA)
- Fluid Mechanics (AREA)
- Analytical Chemistry (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Separation Using Semi-Permeable Membranes (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Devices And Processes Conducted In The Presence Of Fluids And Solid Particles (AREA)
- Catalysts (AREA)
Description
および他のヘテロポリ酸等の水溶性酸を指す。固体触媒は、イオン交換樹脂、酸性形態のゼオライト、および固体担体上で支持される酸等の不溶性触媒を指す。
102 反応器シェル
108 膜チューブ
112 触媒床
114 水供給ライン
116 水噴霧ヘッド
124 生成物流
126 分離器
208 水和反応器
210 選択性膜
222 生成物分離器
228 分離器
302 反応器入口
308 透過出口
310 保持出口
Claims (7)
- 低級オレフィンを水和してアルコールを生成するためのプロセスであって、
アルコール生成物を生成するのに十分な反応条件下で、第1の固形のオレフィン水和触媒を含み、且つ透過膜を含まない反応器の第1の反応区域にて低級オレフィン供給原料と水を接触させるステップであって、反応温度70℃〜250℃、反応圧力5バール〜100バールで反応させるステップと、
アルコールの透過に対して選択的である透過膜を用いて、第2の反応区域から前記アルコール生成物を加熱及び加圧しながら少なくとも一部を選択的に除去するステップと、を含み、
前記第2の反応区域は、前記第1の反応区域の下流で、前記第1の反応区域に流体的に結合されており、前記第2の反応区域は前記透過膜によって分離され、前記透過膜は前記第2の反応区域を透過側と保持側とに分離し、前記保持側は第2の固形のオレフィン水和触媒を含み、
前記反応器は、更に、
前記第2の反応区域の前記透過側から透過流体を通過させるように動作可能である第1の出口と、
前記第2の反応区域の前記保持側から保持流体を通過させるように動作可能である第2の出口と、を備え、
前記第2の反応区域における前記透過膜は、オレフォン水和生成物の少なくとも1種を選択的に除去するように動作可能であり、
前記アルコール生成物の一部を除去する前記ステップが、反応平衡を移動させ、
前記透過膜は、
n−ヘプタン、sec−ブタノール、tert−ブタノールおよび水の混合物の70℃における平均流束が8.24kg/m2h〜32.38kg/m2h、90℃における平均流束が14.75kg/m2h〜47.39kg/m2hであり、sec−ブタノール7.1重量%〜44.6重量%、tert−ブタノール7.1重量%〜44.6重量%および水10.8重量%〜85.8重量%の混合物の70℃における平均流束が19.62kg/m2h〜36.45kg/m2h、sec−ブタノール7.1重量%〜44.6重量%、tert−ブタノール7.1重量%〜44.6重量%および水10.8重量%〜85.8重量%の混合物の90℃における平均流束が27.48kg/m2h〜49.17kg/m2hであり、
70℃におけるn−ヘプタン/水の分離係数が0.3〜0.33、70℃におけるsec−ブタノール/水の分離係数が0.25〜0.47、70℃におけるアルコール/水の分離係数が0.41〜0.79であり、
70℃におけるn−ヘプタン/水の濃縮係数が0.15〜0.23、sec−ブタノール/水の濃縮係数が0.27〜0.65である、プロセス。 - 前記オレフィンは、2〜6個の炭素原子を有するオレフィンから選択される、請求項1に記載のプロセス。
- 前記オレフィンは、3〜5個の炭素原子を有するオレフィンから選択される、請求項1に記載のプロセス。
- 前記選択的に除去するステップは、70℃〜90℃で、圧力2.8バールで行われる、請求項1に記載のプロセス。
- 前記選択的に除去するステップは、前記透過膜の前記透過側の圧力が真空下または供給側より低圧に維持されるように行われる、請求項1〜4のいずれか一項に記載のプロセス。
- 前記オレフィン供給原料と水とを接触させるステップは、アルコール生成物を生成するのに十分な反応条件下で、前記反応区域にてオレフィン供給原料および水とスウィーピングガスとを接触させることをさらに含む、請求項1〜5のいずれか一項に記載のプロセス。
- 前記スウィーピングガスは、窒素、アルゴン、ヘリウム、およびこれらの組み合わせからなる群から選択される、請求項6に記載のプロセス。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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US13/207,122 US8865950B2 (en) | 2011-08-10 | 2011-08-10 | Olefin hydration process with an integrated membrane reactor |
US13/207,122 | 2011-08-10 |
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JP2016153392A JP2016153392A (ja) | 2016-08-25 |
JP6464105B2 true JP6464105B2 (ja) | 2019-02-06 |
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JP2016011848A Active JP6464105B2 (ja) | 2011-08-10 | 2016-01-25 | 一体型膜反応器を用いたオレフィン水和プロセス |
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US (2) | US8865950B2 (ja) |
EP (1) | EP2741848B1 (ja) |
JP (2) | JP2014534163A (ja) |
KR (1) | KR101854955B1 (ja) |
CN (1) | CN103764268B (ja) |
WO (1) | WO2013022565A1 (ja) |
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US8865950B2 (en) * | 2011-08-10 | 2014-10-21 | Saudi Arabian Oil Company | Olefin hydration process with an integrated membrane reactor |
KR101876612B1 (ko) | 2011-12-05 | 2018-07-09 | 사우디 아라비안 오일 컴퍼니 | 친수성 멤브레인 통합형 올레핀 수화 공정 |
DE102014209413A1 (de) * | 2014-05-19 | 2015-11-19 | Evonik Degussa Gmbh | Membrangestützte Katalysatorabtrennung bei der Epoxidierung von Fettsäurealkylestern |
CN105498646B (zh) * | 2015-12-31 | 2019-04-05 | 成都易态科技有限公司 | 反应釜和应用该反应釜的三相流催化反应方法 |
US10570071B1 (en) * | 2018-12-12 | 2020-02-25 | Saudi Arabian Oil Company | Membrane-based process for butanols production from mixed butenes |
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WO2013022565A8 (en) | 2014-03-13 |
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US9233349B2 (en) | 2016-01-12 |
US20130041186A1 (en) | 2013-02-14 |
KR20140054198A (ko) | 2014-05-08 |
EP2741848A1 (en) | 2014-06-18 |
JP2014534163A (ja) | 2014-12-18 |
CN103764268A (zh) | 2014-04-30 |
US20150004073A1 (en) | 2015-01-01 |
CN103764268B (zh) | 2017-03-29 |
KR101854955B1 (ko) | 2018-05-04 |
US8865950B2 (en) | 2014-10-21 |
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