KR100942648B1 - 고정층 촉매 부분 산화 반응기를 이용한 불포화 알데히드및/또는 불포화 지방산의 제조방법 - Google Patents
고정층 촉매 부분 산화 반응기를 이용한 불포화 알데히드및/또는 불포화 지방산의 제조방법 Download PDFInfo
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- KR100942648B1 KR100942648B1 KR1020080031261A KR20080031261A KR100942648B1 KR 100942648 B1 KR100942648 B1 KR 100942648B1 KR 1020080031261 A KR1020080031261 A KR 1020080031261A KR 20080031261 A KR20080031261 A KR 20080031261A KR 100942648 B1 KR100942648 B1 KR 100942648B1
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- unsaturated fatty
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- 150000004670 unsaturated fatty acids Chemical class 0.000 title claims abstract description 42
- 235000021122 unsaturated fatty acids Nutrition 0.000 title claims abstract description 42
- 238000000034 method Methods 0.000 title claims abstract description 38
- 238000007254 oxidation reaction Methods 0.000 title abstract description 13
- 230000003647 oxidation Effects 0.000 title abstract description 9
- 230000003197 catalytic effect Effects 0.000 title abstract description 6
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 title 1
- 238000006243 chemical reaction Methods 0.000 claims abstract description 148
- 239000003054 catalyst Substances 0.000 claims abstract description 71
- 150000001299 aldehydes Chemical class 0.000 claims abstract description 53
- 238000004519 manufacturing process Methods 0.000 claims abstract description 8
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 46
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 46
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 claims description 30
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 14
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 12
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 11
- 239000002994 raw material Substances 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 9
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 7
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 7
- 239000001294 propane Substances 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 6
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 claims description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims description 4
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 claims description 2
- 229910052753 mercury Inorganic materials 0.000 claims description 2
- 150000002790 naphthalenes Chemical class 0.000 claims description 2
- 229920006389 polyphenyl polymer Polymers 0.000 claims description 2
- 235000010333 potassium nitrate Nutrition 0.000 claims description 2
- 239000004323 potassium nitrate Substances 0.000 claims description 2
- 235000010288 sodium nitrite Nutrition 0.000 claims description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 2
- 150000001336 alkenes Chemical class 0.000 abstract description 3
- 239000007789 gas Substances 0.000 description 9
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 239000000463 material Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 101100296544 Caenorhabditis elegans pbo-5 gene Proteins 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 239000011261 inert gas Substances 0.000 description 4
- 230000001590 oxidative effect Effects 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 101150042285 lgc-4 gene Proteins 0.000 description 3
- 229910052750 molybdenum Inorganic materials 0.000 description 3
- 239000011733 molybdenum Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 101100296545 Caenorhabditis elegans pbo-6 gene Proteins 0.000 description 2
- 238000009825 accumulation Methods 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 229910052797 bismuth Inorganic materials 0.000 description 2
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 2
- WUJISAYEUPRJOG-UHFFFAOYSA-N molybdenum vanadium Chemical compound [V].[Mo] WUJISAYEUPRJOG-UHFFFAOYSA-N 0.000 description 2
- 238000005245 sintering Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 102100025269 DENN domain-containing protein 2B Human genes 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 101000722264 Homo sapiens DENN domain-containing protein 2B Proteins 0.000 description 1
- BYUANIDVEAKBHT-UHFFFAOYSA-N [Mo].[Bi] Chemical compound [Mo].[Bi] BYUANIDVEAKBHT-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000007792 gaseous phase Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 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
- 239000003921 oil Substances 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 238000011020 pilot scale process Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 238000007039 two-step reaction Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 1
- 239000012808 vapor phase Substances 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
- B01J8/02—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
- B01J8/06—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 in tube reactors; the solid particles being arranged in tubes
- B01J8/067—Heating or cooling the reactor
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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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
- C07C51/25—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of unsaturated compounds containing no six-membered aromatic ring
- C07C51/252—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of unsaturated compounds containing no six-membered aromatic ring of propene, butenes, acrolein or methacrolein
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
- C07C57/03—Monocarboxylic acids
- C07C57/04—Acrylic acid; Methacrylic acid
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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
- 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
- B01J2208/00168—Controlling the temperature by indirect heat exchange with heat exchange elements outside the bed of solid particles
- B01J2208/00212—Plates; Jackets; Cylinders
- B01J2208/00221—Plates; Jackets; Cylinders comprising baffles for guiding the flow of the heat exchange medium
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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
- B01J2208/00—Processes carried out in the presence of solid particles; Reactors therefor
- B01J2208/00008—Controlling the process
- B01J2208/00017—Controlling the temperature
- B01J2208/0053—Controlling multiple zones along the direction of flow, e.g. pre-heating and after-cooling
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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
- B01J2208/00—Processes carried out in the presence of solid particles; Reactors therefor
- B01J2208/02—Processes carried out in the presence of solid particles; Reactors therefor with stationary particles
- B01J2208/023—Details
- B01J2208/024—Particulate material
- B01J2208/025—Two or more types of catalyst
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- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
Claims (9)
- 프로판, 프로필렌, 이소부틸렌, t-부틸알콜, 또는 메틸-t-부틸에테르로부터 불포화 알데히드, 불포화 지방산, 또는 불포화 알데히드 및 불포화 지방산을 제조하는 공정에 있어서, 프로판, 프로필렌, 이소부틸렌, t-부틸알콜, 또는 메틸-t-부틸에테르로부터 불포화 알데히드를 제조하는 반응영역은 원료가 투입되는 곳으로부터 순차적으로 첫 번째 반응영역과 두 번째 반응영역으로 구분되고, 상기 각각의 반응영역에 촉매를 충전하고 반응 개시 후, 적어도 반응을 위한 스타트업 기간 동안 상기 두 번째 반응영역에서의 촉매층 내의 열점의 온도가 상기 첫 번째 반응영역에서의 촉매층 내의 열점의 온도보다 높게 나타나도록 촉매층 내의 열점의 온도를 조절하는 것을 특징으로 하는 불포화 알데히드, 불포화 지방산, 또는 불포화 알데히드 및 불포화 지방산의 제조방법.
- 청구항 1에 있어서, 상기 촉매층 내의 열점의 온도를 조절하는 방법은 반응관 외부에서 순환되는 온도가 조절된 열전달 매체를 이용하는 것을 특징으로 하는 불포화 알데히드, 불포화 지방산, 또는 불포화 알데히드 및 불포화 지방산의 제조방법.
- 청구항 2에 있어서, 상기 열전달 매체는 용융염, 합성 오일, 디페닐 에테르,폴리페닐, 나프탈렌 유도체, 및 수은으로 구성되는 군으로부터 선택되는 것을 특징 으로 하는 불포화 알데히드, 불포화 지방산, 또는 불포화 알데히드 및 불포화 지방산의 제조방법.
- 청구항 3에 있어서, 상기 용융염은 질산 칼륨 및 아질산 나트륨의 혼합물인 것을 특징으로 하는 불포화 알데히드, 불포화 지방산, 또는 불포화 알데히드 및 불포화 지방산의 제조방법.
- 청구항 1에 있어서, 상기 스타트업 기간은 반응 개시 후 30일 이내인 것을 특징으로 하는 불포화 알데히드, 불포화 지방산, 또는 불포화 알데히드 및 불포화 지방산의 제조방법.
- 청구항 1에 있어서, 상기 스타트업 기간은 프로판, 프로필렌, 이소부틸렌, t-부틸알콜, 또는 메틸-t-부틸에테르의 공간속도가 100hr-1 이상 도달할 때까지의 기간인 것을 특징으로 하는 불포화 알데히드, 불포화 지방산, 또는 불포화 알데히드 및 불포화 지방산의 제조방법.
- 청구항 1에 있어서, 상기 첫 번째 반응영역에서의 촉매층 내의 열점의 온도와 상기 두 번째 반응영역에서의 촉매층 내의 열점의 온도 차이는 20℃ 이내인 것을 특징으로 하는 불포화 알데히드, 불포화 지방산, 또는 불포화 알데히드 및 불포 화 지방산의 제조방법.
- 청구항 1에 있어서, 상기 불포화 알데히드, 불포화 지방산, 또는 불포화 알데히드 및 불포화 지방산을 제조하는 공정은 쉘-앤드-튜브 열교환식 반응기에서 이루어지는 것을 특징으로 하는 불포화 알데히드, 불포화 지방산, 또는 불포화 알데히드 및 불포화 지방산의 제조방법.
- 청구항 1에 있어서, 상기 불포화 알데히드는 (메타)아크롤레인이고, 상기 불포화 지방산은 (메타)아크릴산인 것을 특징으로 하는 불포화 알데히드, 불포화 지방산, 또는 불포화 알데히드 및 불포화 지방산의 제조방법.
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KR20070032800 | 2007-04-03 | ||
KR1020070032800 | 2007-04-03 |
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KR20080090346A KR20080090346A (ko) | 2008-10-08 |
KR100942648B1 true KR100942648B1 (ko) | 2010-02-17 |
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KR1020080031261A KR100942648B1 (ko) | 2007-04-03 | 2008-04-03 | 고정층 촉매 부분 산화 반응기를 이용한 불포화 알데히드및/또는 불포화 지방산의 제조방법 |
Country Status (5)
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US (1) | US8013185B2 (ko) |
KR (1) | KR100942648B1 (ko) |
CN (1) | CN101657408B (ko) |
BR (1) | BRPI0802625B1 (ko) |
WO (1) | WO2008120956A1 (ko) |
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FR2961117B1 (fr) * | 2010-06-11 | 2012-06-08 | Inst Francais Du Petrole | Reacteur echangeur a tubes baionnettes et a tubes de fumees suspendus a la voute superieure du reacteur |
DE102011011895A1 (de) * | 2011-02-21 | 2012-08-23 | Lurgi Gmbh | Rohrreaktor |
KR101819465B1 (ko) * | 2013-07-18 | 2018-01-17 | 닛뽄 가야쿠 가부시키가이샤 | 불포화 알데히드 및/또는 불포화 카본산의 제조 방법 |
KR102084768B1 (ko) * | 2016-11-01 | 2020-03-04 | 주식회사 엘지화학 | 불포화 알데하이드 및 불포화 카르복실산의 제조 방법 |
EP3360611B1 (en) | 2017-02-10 | 2021-04-28 | Technobell D.O.O. Koper | Improved double zone tubular reactor and method for carrying out maleic anhydride production by n-butane oxidation |
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JP2005289919A (ja) | 2004-04-01 | 2005-10-20 | Mitsubishi Chemicals Corp | (メタ)アクリル酸または(メタ)アクロレインの製造方法 |
JP2005334786A (ja) | 2004-05-27 | 2005-12-08 | Mitsubishi Chemicals Corp | 反応装置、反応装置制御システム、及び接触気相酸化反応方法 |
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AU2003201861A1 (en) | 2002-01-11 | 2003-07-30 | Mitsubishi Chemical Corporation | Multipipe reactor, vapor phase catalytic oxidation method using multipipe reactor, and start-up method applied to multipipe reactor |
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US7326389B2 (en) | 2003-12-26 | 2008-02-05 | Lg Chem, Ltd. | Method of producing unsaturated aldehyde and/or unsaturated acid |
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JP2005289919A (ja) | 2004-04-01 | 2005-10-20 | Mitsubishi Chemicals Corp | (メタ)アクリル酸または(メタ)アクロレインの製造方法 |
JP2005334786A (ja) | 2004-05-27 | 2005-12-08 | Mitsubishi Chemicals Corp | 反応装置、反応装置制御システム、及び接触気相酸化反応方法 |
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BRPI0802625A2 (pt) | 2011-08-30 |
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