KR970701686A - 메타크롤레인의 제조 방법(Method for Producing Methacrolein) - Google Patents
메타크롤레인의 제조 방법(Method for Producing Methacrolein)Info
- Publication number
- KR970701686A KR970701686A KR1019960705233A KR19960705233A KR970701686A KR 970701686 A KR970701686 A KR 970701686A KR 1019960705233 A KR1019960705233 A KR 1019960705233A KR 19960705233 A KR19960705233 A KR 19960705233A KR 970701686 A KR970701686 A KR 970701686A
- Authority
- KR
- South Korea
- Prior art keywords
- catalyst composition
- formula
- mixture
- methacrolein
- condition
- Prior art date
Links
- STNJBCKSHOAVAJ-UHFFFAOYSA-N Methacrolein Chemical compound CC(=C)C=O STNJBCKSHOAVAJ-UHFFFAOYSA-N 0.000 title claims abstract 7
- 238000004519 manufacturing process Methods 0.000 title claims abstract 7
- 239000000203 mixture Substances 0.000 claims abstract 15
- 239000003054 catalyst Substances 0.000 claims abstract 10
- 238000000034 method Methods 0.000 claims abstract 6
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims abstract 4
- 239000007789 gas Substances 0.000 claims abstract 4
- 230000003647 oxidation Effects 0.000 claims abstract 4
- 238000007254 oxidation reaction Methods 0.000 claims abstract 4
- 229910052742 iron Inorganic materials 0.000 claims abstract 3
- 229910052749 magnesium Inorganic materials 0.000 claims abstract 3
- 229910052700 potassium Inorganic materials 0.000 claims abstract 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims abstract 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims abstract 2
- 229910052792 caesium Inorganic materials 0.000 claims abstract 2
- 229910001882 dioxygen Inorganic materials 0.000 claims abstract 2
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 2
- 229910052701 rubidium Inorganic materials 0.000 claims abstract 2
- 239000011148 porous material Substances 0.000 claims 5
- 239000010941 cobalt Substances 0.000 claims 4
- 229910017052 cobalt Inorganic materials 0.000 claims 4
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims 2
- 239000011777 magnesium Substances 0.000 claims 2
- 229910052684 Cerium Inorganic materials 0.000 claims 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical group [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 claims 1
- GWXLDORMOJMVQZ-UHFFFAOYSA-N cerium Chemical compound [Ce] GWXLDORMOJMVQZ-UHFFFAOYSA-N 0.000 claims 1
- 229910052750 molybdenum Inorganic materials 0.000 claims 1
- 239000011733 molybdenum Substances 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical group [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 claims 1
- -1 Nb as a raw material Chemical class 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 230000007613 environmental effect Effects 0.000 abstract 1
- 239000002994 raw material Substances 0.000 abstract 1
- 231100000701 toxic element Toxicity 0.000 abstract 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
- C07C45/33—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties
- C07C45/34—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties in unsaturated compounds
- C07C45/35—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties in unsaturated compounds in propene or isobutene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
- C07C47/21—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
- C07C47/22—Acryaldehyde; Methacryaldehyde
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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
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/002—Mixed oxides other than spinels, e.g. perovskite
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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
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/84—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/85—Chromium, molybdenum or tungsten
- B01J23/88—Molybdenum
- B01J23/887—Molybdenum containing in addition other metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/8876—Arsenic, antimony or bismuth
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- 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
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- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/50—Catalysts, in general, characterised by their form or physical properties characterised by their shape or configuration
- B01J35/51—Spheres
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- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- 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
- B01J35/64—Pore diameter
- B01J35/651—50-500 nm
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- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- 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
- B01J35/64—Pore diameter
- B01J35/653—500-1000 nm
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- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- 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
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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
- B01J37/0009—Use of binding agents; Moulding; Pressing; Powdering; Granulating; Addition of materials ameliorating the mechanical properties of the product catalyst
- B01J37/0027—Powdering
- B01J37/0045—Drying a slurry, e.g. spray drying
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- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/02—Impregnation, coating or precipitation
- B01J37/03—Precipitation; Co-precipitation
- B01J37/031—Precipitation
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- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/02—Impregnation, coating or precipitation
- B01J37/03—Precipitation; Co-precipitation
- B01J37/036—Precipitation; Co-precipitation to form a gel or a cogel
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
- C07C45/37—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of >C—O—functional groups to >C=O groups
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- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01J2523/00—Constitutive chemical elements of heterogeneous catalysts
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- Engineering & Computer Science (AREA)
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- Chemical Kinetics & Catalysis (AREA)
- Dispersion Chemistry (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
본 발명은 이소부틸렌 및 3급-부탄올로 이루어지는 군으로부터 선택된 성분 1종 이상을, 산화 촉매 조성물의 존재 하에, 분자상 산소 함유 기체를 사용하여 기상 접촉 산화시켜 메타크롤레인을 제조하는 방법에 관한 것이고, 여기에서 상기 산화 촉매 조성물의 화학식(Ⅰ) Mo12BiaCebKcFedAeBfOg(여기에서, A는 Co 단독이거나, 또는 Co와 Mg와의 혼합물이고, 상기 혼합물 중에서 Mg의 Co에 대한 원자 비율은 0.7 이하이고, B는 Rb, Cs 또는 이들의 혼합물이고, a, b, c, d, e, f 및 g는 각각 Mo 12원자에 대한 Bi, Ce, K, Fe, A, B 및 O의 원자 비율을 나타낸다)로 나타내고, 각 원소의 원자비(a~f) 및 각 원소 Bi, Ce, K 및 Fe의 함유량 및 상대량비가 특정 범위에서 설정된 산화물 촉매 조성물을 사용함을 특징으로 하는 메타크롤레인의 제조 방법을 개시하고 있다. 본 발명의 방법에서 산화물 촉매 조성물은 비교적 간단한 조성을 갖고 따라서 그 제조가 간단해질 수 있으며, 환경 문제상 바람직하지 않은 원소 및 독성 원소를 함유하지 않으며, 또한 균일한 촉매의 제조상 불리한 용해도가 낮은 W, Sb 및 Nb 등의 화합물을 원료로서 함유하지 않지만, 이의 사용에 의해 열안정성 및 내환원성이 우수하기 때문에 촉매 수명이 연장될 뿐만 아니라, 메타크롤레인에 대한 선택률에서도 우수한 촉매 조성물을 사용하여 메타크롤레인을 안정하게 고수율로 제조하는 것이 가능해진다.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (6)
- 이소부틸렌 및 3급-부탄올로 이루어지는 군으로부터 선택된 원소 1종 이상을 분자상 산소 함유 기체를 사용하여 기상 접촉 산화시켜 메타크롤레인을 제조하는 방법에 있어서, 하기 화학식(Ⅰ)로 나타낸 산화물 촉매 조성물을 사용하는 것을 특징으로 하는 메타크롤레인의 제조방법 :Mo12BiaCebKcFedAeBfOg(Ⅰ)상기식에서, A는 코발트 단독이거나, 또는 코발트와 마그네슘과의 혼합물이고, 상기 혼합물 중에서 코발트에 대한 마그네슘의 원자 비율은 0.7 이하이고, B는 루비듐, 세슘 또는 이들의 혼합물이고, a, b, c, d, e, f 및 g는 각각 몰리브덴 12원자에 대한 비스푸드, 세륨, 칼륨, 철, A, B 및 산소의 원자 비율을 나타내고, a는 0<a≤8이고, b는 0<b≤8이고, c는 0<c≤1.2이고, d는 0<d≤2.5이고, e는 1.0<e≤12이고, f는 0<f≤2.0이고, g는 존재하는 나머지 원소의 원자가 조건을 만족시키는데 필요한 산소 원자 수이고, a, b, c 및 d는 하기식 : 0.05≤b(a+b+c)≤0.7, 0<c/(a+b+c)≤0.4 및 0<d/(a+b+d)≤0.9의 조건을 만족시킨다.
- 제1항에 있어서, 상기 A가 코발트 단독인 방법.
- 제1항에 있어서, 산화물 촉매 조성물이 다공질이고, 포어 직경 1㎛ 이하의 포어의 포어 용적이 합계가 상기 산화물 촉매 조성물의 총 포어 용적을 기준하여 95% 이상인 포어 직경 분포를 갖는 방법.
- 제1항에 있어서, 화학식(Ⅰ)에서 a, b 및 c가 식 0.1≤b/(a+b+c)≤0.5의 조건을 만족시키는 방법.
- 제1항에 있어서, 화학식(Ⅰ)에서 a, b 및 c가 식 0.02≤c/(a+b+c)≤0.2의 조건을 만족시키는 방법.
- 제1항에 있어서, 화학식(Ⅰ)에서 a, b 및 d가 식 0.1≤d/(a+b+d)≤0.5의 조건을 만족시키는 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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JP14015194 | 1994-06-22 | ||
JP94-140151 | 1994-06-22 | ||
PCT/JP1995/001234 WO1995035273A1 (fr) | 1994-06-22 | 1995-06-21 | Procede de production de methacroleine |
Publications (2)
Publication Number | Publication Date |
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KR970701686A true KR970701686A (ko) | 1997-04-12 |
KR100186659B1 KR100186659B1 (ko) | 1999-05-15 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019960705233A KR100186659B1 (ko) | 1994-06-22 | 1995-06-21 | 메타크롤레인의 제조 방법 |
Country Status (9)
Country | Link |
---|---|
US (1) | US5728894A (ko) |
EP (1) | EP0767161B1 (ko) |
KR (1) | KR100186659B1 (ko) |
CN (1) | CN1046499C (ko) |
DE (1) | DE69513172T2 (ko) |
ES (1) | ES2140684T3 (ko) |
MY (1) | MY117568A (ko) |
TW (1) | TW299316B (ko) |
WO (1) | WO1995035273A1 (ko) |
Families Citing this family (20)
Publication number | Priority date | Publication date | Assignee | Title |
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KR100579678B1 (ko) * | 2001-12-21 | 2006-05-15 | 아사히 가세이 케미칼즈 가부시키가이샤 | 산화물 촉매 조성물 |
KR100513664B1 (ko) * | 2002-05-16 | 2005-09-07 | 주식회사 엘지화학 | 프로필렌의 부분 산화 반응용 촉매의 제조 방법 |
KR100497175B1 (ko) * | 2003-03-26 | 2005-06-23 | 주식회사 엘지화학 | 프로필렌 및 이소부틸렌 부분산화 반응용 촉매의 제조방법 |
US7232788B2 (en) * | 2003-03-31 | 2007-06-19 | Saudi Basic Industries Corporation | Mixed metal oxide catalysts for the production of unsaturated aldehydes from olefins |
US7501377B2 (en) * | 2003-03-31 | 2009-03-10 | Saudi Basic Industries Corporation | Mixed metal oxide catalysts for the production of unsaturated aldehydes from olefins |
US20040192973A1 (en) * | 2003-03-31 | 2004-09-30 | Saudi Basic Industries Corporation | Mixed metal oxide catalysts for the production of unsaturated aldehydes from olefins |
US7229945B2 (en) * | 2003-12-19 | 2007-06-12 | Saudi Basic Industrics Corporation | Process of making mixed metal oxide catalysts for the production of unsaturated aldehydes from olefins |
US7732367B2 (en) | 2005-07-25 | 2010-06-08 | Saudi Basic Industries Corporation | Catalyst for methacrolein oxidation and method for making and using same |
US7851397B2 (en) | 2005-07-25 | 2010-12-14 | Saudi Basic Industries Corporation | Catalyst for methacrolein oxidation and method for making and using same |
US7649111B2 (en) | 2005-07-25 | 2010-01-19 | Saudi Basic Industries Corporation | Catalyst for the oxidation of a mixed aldehyde feedstock to methacrylic acid and methods for making and using same |
US7649112B2 (en) | 2005-07-25 | 2010-01-19 | Saudi Basic Industries Corporation | Integrated plant for producing 2-ethyl-hexanol and methacrylic acid and a method based thereon |
US7799946B2 (en) * | 2007-02-14 | 2010-09-21 | Saudi Basic Industries Corporation | Process for separating methacrolein from methacrylic acid in a gas phase product from the partial oxidation of isobutene |
CN101385978B (zh) * | 2007-09-12 | 2011-04-20 | 上海华谊丙烯酸有限公司 | 一种合成甲基丙烯醛的催化剂及其制备方法 |
WO2013002029A1 (ja) | 2011-06-28 | 2013-01-03 | 旭化成ケミカルズ株式会社 | 酸化物触媒 |
US8921257B2 (en) | 2011-12-02 | 2014-12-30 | Saudi Basic Industries Corporation | Dual function partial oxidation catalyst for propane to acrylic acid conversion |
US8722940B2 (en) | 2012-03-01 | 2014-05-13 | Saudi Basic Industries Corporation | High molybdenum mixed metal oxide catalysts for the production of unsaturated aldehydes from olefins |
RU2615762C2 (ru) * | 2012-09-28 | 2017-04-11 | Асахи Касеи Кемикалз Корпорейшн | Оксидный катализатор и способ его получения, а также способы получения ненасыщенного альдегида, диолефина и ненасыщенного нитрила |
CN103721722B (zh) * | 2012-10-10 | 2017-03-08 | 上海华谊丙烯酸有限公司 | 复合氧化物催化剂及其制备方法 |
CN110420643A (zh) * | 2019-08-16 | 2019-11-08 | 中国科学院过程工程研究所 | 一种蛋壳型复合金属催化剂的制备方法及其应用 |
US20220023837A1 (en) * | 2019-09-30 | 2022-01-27 | Lg Chem, Ltd. | Ammoxidation catalyst for propylene, manufacturing method of the same catalyst, ammoxidation method using the same catalyst |
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-
1995
- 1995-06-21 CN CN95192158A patent/CN1046499C/zh not_active Expired - Lifetime
- 1995-06-21 ES ES95922726T patent/ES2140684T3/es not_active Expired - Lifetime
- 1995-06-21 EP EP95922726A patent/EP0767161B1/en not_active Expired - Lifetime
- 1995-06-21 DE DE69513172T patent/DE69513172T2/de not_active Expired - Lifetime
- 1995-06-21 US US08/700,469 patent/US5728894A/en not_active Expired - Lifetime
- 1995-06-21 KR KR1019960705233A patent/KR100186659B1/ko not_active IP Right Cessation
- 1995-06-21 WO PCT/JP1995/001234 patent/WO1995035273A1/ja active IP Right Grant
- 1995-06-22 MY MYPI95001695A patent/MY117568A/en unknown
- 1995-06-22 TW TW084106431A patent/TW299316B/zh not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
CN1046499C (zh) | 1999-11-17 |
EP0767161A4 (en) | 1997-09-17 |
ES2140684T3 (es) | 2000-03-01 |
CN1143946A (zh) | 1997-02-26 |
DE69513172T2 (de) | 2000-08-24 |
MY117568A (en) | 2004-07-31 |
TW299316B (ko) | 1997-03-01 |
EP0767161A1 (en) | 1997-04-09 |
KR100186659B1 (ko) | 1999-05-15 |
US5728894A (en) | 1998-03-17 |
WO1995035273A1 (fr) | 1995-12-28 |
EP0767161B1 (en) | 1999-11-03 |
DE69513172D1 (de) | 1999-12-09 |
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