JP7470096B2 - 触媒、その調製方法、及び選択的水素化プロセス - Google Patents
触媒、その調製方法、及び選択的水素化プロセス Download PDFInfo
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- JP7470096B2 JP7470096B2 JP2021504518A JP2021504518A JP7470096B2 JP 7470096 B2 JP7470096 B2 JP 7470096B2 JP 2021504518 A JP2021504518 A JP 2021504518A JP 2021504518 A JP2021504518 A JP 2021504518A JP 7470096 B2 JP7470096 B2 JP 7470096B2
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- 239000003054 catalyst Substances 0.000 title claims description 107
- 238000000034 method Methods 0.000 title claims description 69
- 238000002360 preparation method Methods 0.000 title description 12
- 238000005984 hydrogenation reaction Methods 0.000 title description 5
- 230000008569 process Effects 0.000 claims description 60
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 53
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical group [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 47
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 38
- 229910052684 Cerium Inorganic materials 0.000 claims description 28
- 229910052782 aluminium Inorganic materials 0.000 claims description 27
- 229910052751 metal Inorganic materials 0.000 claims description 26
- 239000002184 metal Substances 0.000 claims description 26
- GWXLDORMOJMVQZ-UHFFFAOYSA-N cerium Chemical group [Ce] GWXLDORMOJMVQZ-UHFFFAOYSA-N 0.000 claims description 25
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical group [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 23
- DLDJFQGPPSQZKI-UHFFFAOYSA-N but-2-yne-1,4-diol Chemical compound OCC#CCO DLDJFQGPPSQZKI-UHFFFAOYSA-N 0.000 claims description 22
- 229910052759 nickel Inorganic materials 0.000 claims description 20
- 239000006227 byproduct Substances 0.000 claims description 17
- 239000002245 particle Substances 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910045601 alloy Inorganic materials 0.000 description 33
- 239000000956 alloy Substances 0.000 description 33
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 22
- 239000000243 solution Substances 0.000 description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 229910000420 cerium oxide Inorganic materials 0.000 description 18
- 239000000203 mixture Substances 0.000 description 18
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 18
- 229910052802 copper Inorganic materials 0.000 description 15
- 239000010949 copper Substances 0.000 description 15
- 229910052742 iron Inorganic materials 0.000 description 13
- 238000004458 analytical method Methods 0.000 description 11
- 239000012527 feed solution Substances 0.000 description 11
- 229910052804 chromium Inorganic materials 0.000 description 10
- 239000011651 chromium Substances 0.000 description 10
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 229910052750 molybdenum Inorganic materials 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 8
- 230000003197 catalytic effect Effects 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 7
- 239000012670 alkaline solution Substances 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 238000002156 mixing Methods 0.000 description 7
- 239000011733 molybdenum Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 229910052718 tin Inorganic materials 0.000 description 7
- 239000011135 tin Substances 0.000 description 7
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 6
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 6
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 6
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 229910052719 titanium Inorganic materials 0.000 description 6
- 239000010936 titanium Substances 0.000 description 6
- 229910052720 vanadium Inorganic materials 0.000 description 6
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 6
- 229910052725 zinc Inorganic materials 0.000 description 6
- 239000011701 zinc Substances 0.000 description 6
- 229910052726 zirconium Inorganic materials 0.000 description 6
- 230000004913 activation Effects 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 4
- 150000001241 acetals Chemical class 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- CETPSERCERDGAM-UHFFFAOYSA-N ceric oxide Chemical compound O=[Ce]=O CETPSERCERDGAM-UHFFFAOYSA-N 0.000 description 3
- 229910000422 cerium(IV) oxide Inorganic materials 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 229910052746 lanthanum Inorganic materials 0.000 description 2
- 238000002386 leaching Methods 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 230000000737 periodic effect Effects 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- -1 2.1 wt.% to 2.8 wt.% Chemical compound 0.000 description 1
- NMPJHMFXHISVBR-UHFFFAOYSA-N 4-(oxolan-2-yloxy)butan-1-ol Chemical compound OCCCCOC1CCCO1 NMPJHMFXHISVBR-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- 229910003310 Ni-Al Inorganic materials 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 238000005275 alloying Methods 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 229910002056 binary alloy Inorganic materials 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000009904 heterogeneous catalytic hydrogenation reaction Methods 0.000 description 1
- 239000002815 homogeneous catalyst Substances 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 150000002602 lanthanoids Chemical class 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000010309 melting process Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 230000000979 retarding effect Effects 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 150000003377 silicon compounds Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229910002058 ternary alloy Inorganic materials 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- 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
- C07C29/17—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds
- C07C29/172—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds with the obtention of a fully saturated alcohol
-
- 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
- B01J25/00—Catalysts of the Raney type
- B01J25/02—Raney nickel
-
- 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
- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/02—Boron or aluminium; Oxides or hydroxides thereof
-
- 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
- B01J23/83—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 rare earths or actinides
-
- 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
- B01J35/40—Catalysts, in general, characterised by their form or physical properties characterised by dimensions, e.g. grain size
-
- 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
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/0009—Use of binding agents; Moulding; Pressing; Powdering; Granulating; Addition of materials ameliorating the mechanical properties of the product catalyst
- B01J37/0063—Granulating
-
- 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
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/009—Preparation by separation, e.g. by filtration, decantation, screening
-
- 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
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/04—Mixing
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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
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/08—Heat treatment
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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
- B01J8/02—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
- B01J8/025—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 shaped bed
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- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Thermal Sciences (AREA)
- Fluid Mechanics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
本出願は、「CATALYSTS,PREPARATION METHOD THEREOF,AND SELECTIVE HYDROGENATION PROCESSES」と題する、2018年8月8日出願の米国特許仮出願第62/715,926号の出願日の利益を主張し、その開示は参照により本明細書に組み込まれる。
本発明は、触媒に関し、より具体的には、1,4ブタンジオールを調製するための触媒、その調製方法、及び触媒を用いる選択的水素化プロセスに関する。
触媒の調製
触媒の試験
比較例2:La促進ニッケル触媒
実施例1:Ce促進ニッケル触媒
実施例2:Ce促進ニッケル触媒(より高いCe含有量)
実施例3:Ce促進ニッケル触媒。
[発明の態様]
[1]
1,4-ブタンジオールを作製するためのプロセスであって、
1,4-ブチンジオールを含む溶液を、触媒の存在下で水素と反応させることを含み、
前記触媒が、セリウムを含む、プロセス。
[2]
前記触媒が、固定床、懸濁液、又はそれらの組み合わせの形態である、1に記載のプロセス。
[3]
前記触媒が、前記固定床の形態であり、約1mm~約8mmの範囲の粒径を有する、2に記載のプロセス。
[4]
前記触媒が前記懸濁液の形態であり、約10~約100μmの範囲の中央粒径を有する、2に記載のプロセス。
[5]
前記触媒が、Ni、Co、Cu、Fe、及びそれらの混合物からなる群から選択される少なくとも第1の元素を更に含む、1に記載のプロセス。
[6]
前記第1の元素が、Niである、5に記載のプロセス。
[7]
前記触媒が、アルミニウム、モリブデン、クロム、鉄、銅、スズ、ジルコニウム、亜鉛、チタン、バナジウム、及びそれらの混合物からなる群から選択される少なくとも第2の元素を更に含む、5に記載のプロセス。
[8]
前記第2の元素が、アルミニウムである、7に記載のプロセス。
[9]
前記触媒が、骨格金属触媒である、1に記載のプロセス。
[10]
セリウムが、前記触媒の約1重量%~約5重量%の範囲の量で存在する、1に記載のプロセス。
[11]
セリウムが、前記触媒の約1.5重量%~約3.0重量%の範囲の量で存在する、1に記載のプロセス。
[12]
前記1,4-ブチンジオールを含む溶液が、約6.0~約11.0の範囲のpHを有する、1に記載のプロセス。
[13]
前記1,4-ブチンジオールを含む溶液が、約9.0~約10.0のpHを有する、1に記載のプロセス。
[14]
前記プロセスが、前記ブタノール及び前記1,4-ブタンジオールの総重量に基づいて、約3.0重量%未満の範囲のブタノールを副生成物として生成する、1に記載のプロセス。
[15]
1,4-ブタンジオールを作製するための触媒であって、
プロモータとしてセリウムを含む骨格金属触媒を含む、触媒。
[16]
セリウムが、前記触媒の約1重量%~約5.0重量%の範囲の量で存在する、15に記載の触媒。
[17]
セリウムが、前記触媒の約1.5重量%~約3.0重量%の範囲の量で存在する、15に記載の触媒。
[18]
触媒を調製するプロセスであって、
酸化セリウム、第1の元素、及び第2の元素を溶融及び混合して合金を形成することを含み、
前記第1の元素が、Ni、Co、Cu、Fe、及びそれらの混合物からなる群から選択され、前記第2の元素が、アルミニウム、モリブデン、クロム、鉄、銅、スズ、ジルコニウム、亜鉛、チタン、バナジウム、及びそれらの混合物からなる群から選択される、プロセス。
[19]
前記第1の元素が、Niであり、前記第2の元素が、アルミニウムである、18に記載のプロセス。
[20]
Niが、前記酸化セリウム、Ni、及びアルミニウムの総重量に基づいて、約40重量%~約60重量%の範囲の量で存在する、19に記載のプロセス。
[21]
アルミニウムが、前記酸化セリウム、Ni、及びアルミニウムの総重量に基づいて、約40重量%~約60重量%の範囲の量で存在する、19に記載のプロセス。
[22]
酸化セリウムが、前記酸化セリウム、前記第1の元素、及び前記第2の元素の総重量に基づいて、約1重量%~約5重量%の範囲の量で存在する、18に記載のプロセス。
[23]
前記第1の元素が、Niであり、前記第2の元素が、アルミニウムである、22に記載のプロセス。
[24]
酸化セリウムが、前記溶融及び混合中に前記合金中のセリウムに変換される、18に記載のプロセス。
[25]
前記合金をアルカリ水溶液と接触させて、前記触媒を生成することを更に含む、18に記載のプロセス。
[26]
前記触媒が、骨格金属触媒である、25に記載のプロセス。
[27]
18に記載のプロセスによって生成される、触媒。
Claims (7)
- 1,4-ブタンジオールを作製するためのプロセスであって、
前記プロセスが、1,4-ブチンジオールを含む溶液を、骨格金属触媒の存在下で水素と反応させることを含み、ここで前記骨格金属触媒が第1の元素、第2の元素およびプロモータからなり、
前記プロモータがセリウムであり、
前記第1の元素がニッケルであり、そして前記第2の元素がアルミニウムである、そして
前記触媒が、固定床の形態であり、かつ1mm~8mmの範囲の粒径を有する、
プロセス。 - 前記触媒が、2mm~5mmの範囲の粒径を有する、請求項1に記載のプロセス。
- セリウムが、前記触媒の1重量%~5重量%の範囲の量で存在する、請求項1に記載のプロセス。
- セリウムが、前記触媒の1.5重量%~3.0重量%の範囲の量で存在する、請求項1に記載のプロセス。
- 前記1,4-ブチンジオールを含む溶液が、6.0~11.0の範囲のpHを有する、請求項1に記載のプロセス。
- 前記1,4-ブチンジオールを含む溶液が、9.0~10.0のpHを有する、請求項1に記載のプロセス。
- 前記プロセスがブタノールを副生成物として生成し、前記ブタノールが、前記ブタノール及び前記1,4-ブタンジオールの総重量に基づいて、3.0重量%未満の範囲である、請求項1に記載のプロセス。
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Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2009507058A (ja) | 2005-09-06 | 2009-02-19 | ビーエーエスエフ ソシエタス・ヨーロピア | 1,4−ブチンジオールからのポリマーの副生成物の分離方法 |
US20100016643A1 (en) | 2007-02-15 | 2010-01-21 | Basf Se | Process for preparing 1,4-butanediol |
CN106861704A (zh) | 2017-02-28 | 2017-06-20 | 山西大学 | 一种镍‑助剂‑氧化铝‑氧化锆催化剂及制备方法和应用 |
CN106861701A (zh) | 2017-02-28 | 2017-06-20 | 山西大学 | 一种纳米粉体镍催化剂及制备方法和应用 |
CN107778137A (zh) | 2016-08-30 | 2018-03-09 | 中国石油化工股份有限公司 | 制备1,4‑丁二醇的方法 |
WO2018054759A1 (de) | 2016-09-23 | 2018-03-29 | Basf Se | Verfahren zur aktivierung eines katalysatorfestbetts, das monolithische katalysatorformkörper enthält oder aus monolithischen katalysatorformkörpern besteht |
WO2018060269A1 (en) | 2016-09-30 | 2018-04-05 | Evonik Degussa Gmbh | Process and catalyst for preparing 1,4-butanediol |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4153578A (en) * | 1978-07-31 | 1979-05-08 | Gaf Corporation | Catalyst comprising Raney nickel with adsorbed molybdenum compound |
DE19641707A1 (de) * | 1996-10-10 | 1998-04-16 | Basf Ag | Verfahren zur Herstellung von 1,4-Butandiol durch katalytische Hydrierung von 1,4-Butindiol |
DE19753501A1 (de) | 1997-12-03 | 1999-06-10 | Bayer Ag | Raney-Nickel-Katalysatoren, ein Verfahren zu deren Herstellung und deren Verwendung zur Hydrierung organischer Verbindungen |
US7183327B2 (en) * | 2004-03-18 | 2007-02-27 | Conocophillips Company | Optimized particle distribution for slurry bubble column reactors |
US7553517B1 (en) * | 2005-09-15 | 2009-06-30 | The United States Of America As Represented By The United States Department Of Energy | Method of applying a cerium diffusion coating to a metallic alloy |
CN101199930A (zh) | 2006-12-14 | 2008-06-18 | 马波 | 一种高碳多元醇加氢裂解催化剂,其制备方法和应用 |
CN101423775B (zh) * | 2007-11-01 | 2010-05-12 | 中国石油天然气股份有限公司 | 一种选择性镍系加氢催化剂及其制备方法 |
WO2013101969A1 (en) * | 2011-12-30 | 2013-07-04 | E. I. Du Pont De Nemours And Company | Process for preparing 1, 6-hexanediol |
CN107778138B (zh) * | 2016-08-30 | 2021-03-12 | 中国石油化工股份有限公司 | 一种1,4-丁炔二醇两段加氢制备1,4-丁二醇的方法 |
TWI787215B (zh) * | 2016-11-22 | 2022-12-21 | 美商W R 康格雷氏公司 | 降低損耗的催化劑及其製造方法 |
-
2019
- 2019-08-06 CN CN201980049535.9A patent/CN112469502A/zh active Pending
- 2019-08-06 EP EP19847556.8A patent/EP3833472A4/en active Pending
- 2019-08-06 JP JP2021504518A patent/JP7470096B2/ja active Active
- 2019-08-06 WO PCT/US2019/045228 patent/WO2020033358A1/en unknown
- 2019-08-06 TW TW108127895A patent/TWI829737B/zh active
- 2019-08-06 US US17/263,279 patent/US11498891B2/en active Active
-
2022
- 2022-10-11 US US17/963,698 patent/US20230051744A1/en active Pending
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2009507058A (ja) | 2005-09-06 | 2009-02-19 | ビーエーエスエフ ソシエタス・ヨーロピア | 1,4−ブチンジオールからのポリマーの副生成物の分離方法 |
US20100016643A1 (en) | 2007-02-15 | 2010-01-21 | Basf Se | Process for preparing 1,4-butanediol |
CN107778137A (zh) | 2016-08-30 | 2018-03-09 | 中国石油化工股份有限公司 | 制备1,4‑丁二醇的方法 |
WO2018054759A1 (de) | 2016-09-23 | 2018-03-29 | Basf Se | Verfahren zur aktivierung eines katalysatorfestbetts, das monolithische katalysatorformkörper enthält oder aus monolithischen katalysatorformkörpern besteht |
WO2018060269A1 (en) | 2016-09-30 | 2018-04-05 | Evonik Degussa Gmbh | Process and catalyst for preparing 1,4-butanediol |
CN106861704A (zh) | 2017-02-28 | 2017-06-20 | 山西大学 | 一种镍‑助剂‑氧化铝‑氧化锆催化剂及制备方法和应用 |
CN106861701A (zh) | 2017-02-28 | 2017-06-20 | 山西大学 | 一种纳米粉体镍催化剂及制备方法和应用 |
Non-Patent Citations (1)
Title |
---|
多羅間 公雄 他,ラネーニッケルに対するアルカリの促進作用の速度論的研究,工業化学雑誌,1958年,Vol. 61, No. 7,pp. 843-846,DOI: 10.1246/nikkashi1898.61.843 |
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