KR20080035183A - 금속이 도핑된 술폰화 양이온교환 수지 촉매 및 이를 이용한 메틸이소부틸케톤의 제조방법 - Google Patents
금속이 도핑된 술폰화 양이온교환 수지 촉매 및 이를 이용한 메틸이소부틸케톤의 제조방법 Download PDFInfo
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- KR20080035183A KR20080035183A KR1020060101508A KR20060101508A KR20080035183A KR 20080035183 A KR20080035183 A KR 20080035183A KR 1020060101508 A KR1020060101508 A KR 1020060101508A KR 20060101508 A KR20060101508 A KR 20060101508A KR 20080035183 A KR20080035183 A KR 20080035183A
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- Prior art keywords
- exchange resin
- catalyst
- weight
- cation exchange
- palladium
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- 239000003054 catalyst Substances 0.000 title claims abstract description 101
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 title claims abstract description 38
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 title claims abstract description 33
- 238000004519 manufacturing process Methods 0.000 title claims description 16
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 112
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 67
- 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 claims abstract description 58
- 238000006243 chemical reaction Methods 0.000 claims abstract description 53
- 229910052763 palladium Inorganic materials 0.000 claims abstract description 48
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims abstract description 26
- 238000005342 ion exchange Methods 0.000 claims abstract description 19
- 239000003729 cation exchange resin Substances 0.000 claims abstract description 18
- 229910052751 metal Inorganic materials 0.000 claims abstract description 18
- 239000002184 metal Substances 0.000 claims abstract description 18
- 238000000034 method Methods 0.000 claims abstract description 17
- 239000010949 copper Substances 0.000 claims abstract description 15
- 239000010931 gold Substances 0.000 claims abstract description 12
- 239000003456 ion exchange resin Substances 0.000 claims abstract description 12
- 229920003303 ion-exchange polymer Polymers 0.000 claims abstract description 12
- 229910052709 silver Inorganic materials 0.000 claims abstract description 12
- 239000004332 silver Substances 0.000 claims abstract description 12
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229910052759 nickel Inorganic materials 0.000 claims abstract description 10
- 229910052707 ruthenium Inorganic materials 0.000 claims abstract description 10
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229910017052 cobalt Inorganic materials 0.000 claims abstract description 9
- 239000010941 cobalt Substances 0.000 claims abstract description 9
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229910052802 copper Inorganic materials 0.000 claims abstract description 9
- 229910052737 gold Inorganic materials 0.000 claims abstract description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 18
- 239000011347 resin Substances 0.000 claims description 13
- 229920005989 resin Polymers 0.000 claims description 13
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 10
- 239000011148 porous material Substances 0.000 claims description 8
- 239000002245 particle Substances 0.000 claims description 6
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- 239000003607 modifier Substances 0.000 claims description 3
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 3
- 230000000694 effects Effects 0.000 abstract description 14
- 239000000463 material Substances 0.000 abstract description 6
- 238000002360 preparation method Methods 0.000 abstract description 5
- 230000002194 synthesizing effect Effects 0.000 abstract description 2
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 28
- 238000005984 hydrogenation reaction Methods 0.000 description 20
- OZXIZRZFGJZWBF-UHFFFAOYSA-N 1,3,5-trimethyl-2-(2,4,6-trimethylphenoxy)benzene Chemical compound CC1=CC(C)=CC(C)=C1OC1=C(C)C=C(C)C=C1C OZXIZRZFGJZWBF-UHFFFAOYSA-N 0.000 description 16
- SHOJXDKTYKFBRD-UHFFFAOYSA-N mesityl oxide Natural products CC(C)=CC(C)=O SHOJXDKTYKFBRD-UHFFFAOYSA-N 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 238000006297 dehydration reaction Methods 0.000 description 13
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- 239000006227 byproduct Substances 0.000 description 12
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 10
- 230000001965 increasing effect Effects 0.000 description 10
- 230000018044 dehydration Effects 0.000 description 9
- 239000007864 aqueous solution Substances 0.000 description 8
- 150000002500 ions Chemical group 0.000 description 8
- 230000003197 catalytic effect Effects 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- 239000012153 distilled water Substances 0.000 description 7
- 230000007774 longterm Effects 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 238000009833 condensation Methods 0.000 description 6
- 230000005494 condensation Effects 0.000 description 6
- 239000002243 precursor Substances 0.000 description 6
- 230000002829 reductive effect Effects 0.000 description 6
- WVYWICLMDOOCFB-UHFFFAOYSA-N 4-methyl-2-pentanol Chemical compound CC(C)CC(C)O WVYWICLMDOOCFB-UHFFFAOYSA-N 0.000 description 5
- 238000005882 aldol condensation reaction Methods 0.000 description 5
- 239000011324 bead Substances 0.000 description 5
- 238000010348 incorporation Methods 0.000 description 5
- 239000003377 acid catalyst Substances 0.000 description 4
- 229920001429 chelating resin Polymers 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 229960004592 isopropanol Drugs 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 4
- YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 3
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical group CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 229940023913 cation exchange resins Drugs 0.000 description 3
- -1 ketone compound Chemical class 0.000 description 3
- 150000002823 nitrates Chemical class 0.000 description 3
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- UWNADWZGEHDQAB-UHFFFAOYSA-N 2,5-dimethylhexane Chemical group CC(C)CCC(C)C UWNADWZGEHDQAB-UHFFFAOYSA-N 0.000 description 2
- WFRBDWRZVBPBDO-UHFFFAOYSA-N 2-methyl-2-pentanol Chemical compound CCCC(C)(C)O WFRBDWRZVBPBDO-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 238000001994 activation Methods 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 238000011049 filling Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 230000001737 promoting effect Effects 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 229910001961 silver nitrate Inorganic materials 0.000 description 2
- VADUDTKCGJKNDY-UHFFFAOYSA-N 4-Methyl-4-penten-2-one Chemical compound CC(=C)CC(C)=O VADUDTKCGJKNDY-UHFFFAOYSA-N 0.000 description 1
- 101710134784 Agnoprotein Proteins 0.000 description 1
- 229910017944 Ag—Cu Inorganic materials 0.000 description 1
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 1
- 229910017709 Ni Co Inorganic materials 0.000 description 1
- 229910003267 Ni-Co Inorganic materials 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 229910003262 Ni‐Co Inorganic materials 0.000 description 1
- OUUQCZGPVNCOIJ-UHFFFAOYSA-M Superoxide Chemical class [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- UFMZWBIQTDUYBN-UHFFFAOYSA-N cobalt dinitrate Chemical compound [Co+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O UFMZWBIQTDUYBN-UHFFFAOYSA-N 0.000 description 1
- 229910001981 cobalt nitrate Inorganic materials 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 229910001431 copper ion Inorganic materials 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- KBJMLQFLOWQJNF-UHFFFAOYSA-N nickel(ii) nitrate Chemical compound [Ni+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O KBJMLQFLOWQJNF-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical compound [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 description 1
- GPNDARIEYHPYAY-UHFFFAOYSA-N palladium(ii) nitrate Chemical compound [Pd+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O GPNDARIEYHPYAY-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000012508 resin bead Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 230000002441 reversible effect Effects 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
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000003313 weakening effect Effects 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
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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
- B01J39/00—Cation exchange; Use of material as cation exchangers; Treatment of material for improving the cation exchange properties
- B01J39/08—Use of material as cation exchangers; Treatment of material for improving the cation exchange properties
- B01J39/10—Oxides or hydroxides
-
- 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
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
- B01J23/42—Platinum
-
- 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
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y40/00—Manufacture or treatment of nanostructures
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Abstract
Description
Claims (9)
- 다음 화학식 1로 표시되는 것을 특징으로 하는 이온교환수지 촉매;[화학식 1]Pd(a)M1(b)M2(c)/다공성 술폰화 양이온교환수지상기 화학식 1에서, Pd는 팔라듐을 나타내고; M1은 니켈(Ni), 코발트(Co) 및 은(Ag) 중에서 선택된 하나 또는 그 이상의 성분을 나타내고; M2는 개량제 성분으로서 구리(Cu), 금(Au) 및 루테늄(Ru) 중에서 선택된 하나 또는 그 이상의 성분을 나타내며; (a), (b), (c)는 다공성 양이온 교환수지의 건조중량을 기준으로 각 금속 성분의 중량을 백분율로 나타낸 것으로 (a)는 0.3 ~ 1.5 중량%, (b)는 0.005 ~ 0.5 중량%, (c)는 0 ~ 0.5 중량% 범위의 수이다.
- 제 1 항에 있어서, 상기 다공성 양이온 교환수지의 건조중량을 기준으로 (a)는 0.5 ~ 1.2 중량%, (b)는 0.01 ~ 0.25 중량%, (c)는 0 ~ 0.36 중량% 인 것을 특징으로 하는 촉매.
- 제 1 항에 있어서, 상기 다공성 양이온 교환수지는 평균 입자 직경이 100 ㎛ ~ 2 ㎜이고, 평균 기공크기가 5 ~ 250 ㎚이며, 비표면적은 10 ~ 100 ㎡/g이고, 건 조중량을 기준으로 총 공극율이 0.1 ~ 0.9 ㎤/g이고, 술폰산기 함량은 4.0 ~ 7.0 meq/g인 것을 특징으로 하는 촉매.
- 제 3 항에 있어서, 상기 다공성 양이온 교환수지는 평균 입자 직경이 0.2 ~ 1.4 ㎜이고, 평균 기공크기가 15 ~ 100 ㎚이며, 비표면적은 20 ~ 50 ㎡/g이고, 건조중량을 기준으로 총 공극율이 0.15 ~ 0.5 ㎤/g이고, 술폰산기 함량은 4.2 ~ 6.0 meq/g인 것을 특징으로 하는 촉매.
- H+형 다공성 술폰화 양이온 교환수지에, 다음 화학식 1에서 제시된 M1 및 M2에서 선택된 금속 성분을 일차적으로 이온 교환시킨 뒤, 팔라듐 성분을 이온 교환시켜 제조되는 것을 특징으로 하는 다음 화학식 1로 표시되는 이온교환수지 촉매의 제조방법;[화학식 1]Pd(a)M1(b)M2(c)/다공성 술폰화 양이온교환수지상기 화학식 1에서, Pd는 팔라듐을 나타내고; M1은 코발트(Co),니켈(Ni) 및 은(Ag) 중에서 선택된 하나 또는 그 이상의 성분을 나타내고; M2는 개량제 성분으로서 구리(Cu), 금(Au) 및 루테늄(Ru) 중에서 선택된 하나 또는 그 이상의 성분을 나타내며; (a), (b), (c)는 다공성 양이온 교환수지의 건조중량을 기준으로 각 금속 성분의 중량을 백분율로 나타낸 것으로 (a)는 0.3 ~ 1.5 중량%, (b)는 0.005 ~ 0.5 중량%, (c)는 0 ~ 0.5 중량% 범위의 수이다.
- 촉매 존재 하에서 아세톤과 수소를 접촉시켜 메틸이소부틸케톤을 제조하는 방법에 있어서,상기 촉매는 청구항 1 내지 4 중에서 선택된 어느 한 항의 이온교환 수지 촉매를 사용하는 것을 특징으로 하는 메틸이소부틸케톤의 제조방법.
- 제 6 항에 있어서, 상기 아세톤은 반응온도 90 ~ 150 ℃ 및 10 ~ 35기압에서 촉매 존재 하에서 수소와 접촉되는 것을 특징으로 하는 방법.
- 제 6 항에 있어서, 상기 아세톤과 수소의 접촉은 수소/아세톤 몰 비가 0.15 ~ 0.5/1인 흐름 조건하에서 진행됨을 특징으로 하는 방법.
- 제 6 항에 있어서, 상기 아세톤과 수소는 고정층 반응기에서 연속반응조건하 에서 접촉됨을 특징으로 하는 방법.
Priority Applications (1)
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US8471069B2 (en) | 2010-06-30 | 2013-06-25 | Rohm And Haas Company | Mixed bed polymeric catalyst |
KR101323632B1 (ko) * | 2010-06-30 | 2013-11-14 | 롬 앤드 하아스 컴패니 | 불균일계 촉매의 제조 방법 |
KR101416603B1 (ko) * | 2010-06-30 | 2014-07-08 | 롬 앤드 하아스 컴패니 | 다반응 이기능성 폴리머 촉매 |
EP2332649A3 (en) * | 2009-11-25 | 2017-09-06 | Rohm and Haas Company | Catalyst composition comprising a metal alloy as nanometric cluster |
CN110180589A (zh) * | 2019-05-30 | 2019-08-30 | 丹东明珠特种树脂有限公司 | 合成mibk用树脂催化剂及其制备方法 |
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DE4343453A1 (de) | 1993-12-20 | 1995-06-22 | Bayer Ag | Verfahren zur Herstellung von Alkyl-tert.-alkyl-ether enthaltenden Kohlenwasserstoffgemischen |
US5684207A (en) | 1994-05-06 | 1997-11-04 | Industrial Technology Research Institute | Preparation of methyl isobutyl ketone |
JP2004224743A (ja) | 2003-01-24 | 2004-08-12 | Japan Energy Corp | ケトン化合物の製造方法 |
JP2005255419A (ja) | 2004-03-09 | 2005-09-22 | Kuraray Co Ltd | パラジウム−バイメタルカチオン交換モンモリロナイトおよびその用途 |
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EP2332649A3 (en) * | 2009-11-25 | 2017-09-06 | Rohm and Haas Company | Catalyst composition comprising a metal alloy as nanometric cluster |
US8471069B2 (en) | 2010-06-30 | 2013-06-25 | Rohm And Haas Company | Mixed bed polymeric catalyst |
KR101323632B1 (ko) * | 2010-06-30 | 2013-11-14 | 롬 앤드 하아스 컴패니 | 불균일계 촉매의 제조 방법 |
KR101416603B1 (ko) * | 2010-06-30 | 2014-07-08 | 롬 앤드 하아스 컴패니 | 다반응 이기능성 폴리머 촉매 |
CN110180589A (zh) * | 2019-05-30 | 2019-08-30 | 丹东明珠特种树脂有限公司 | 合成mibk用树脂催化剂及其制备方法 |
CN110180589B (zh) * | 2019-05-30 | 2022-02-18 | 丹东明珠特种树脂有限公司 | 合成mibk用树脂催化剂及其制备方法 |
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