CA1065341A - Oxidation of propylene and isobutylene to obtain the corresponding unsaturated aldehydes and acids - Google Patents
Oxidation of propylene and isobutylene to obtain the corresponding unsaturated aldehydes and acidsInfo
- Publication number
- CA1065341A CA1065341A CA246,905A CA246905A CA1065341A CA 1065341 A CA1065341 A CA 1065341A CA 246905 A CA246905 A CA 246905A CA 1065341 A CA1065341 A CA 1065341A
- Authority
- CA
- Canada
- Prior art keywords
- catalyst
- catalytic material
- propylene
- oxidation
- isobutylene
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 title claims abstract description 14
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 title claims abstract description 12
- 150000001299 aldehydes Chemical class 0.000 title claims abstract description 8
- 239000002253 acid Substances 0.000 title claims abstract description 5
- 230000003647 oxidation Effects 0.000 title claims abstract 5
- 238000007254 oxidation reaction Methods 0.000 title claims abstract 5
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 title claims abstract 4
- 150000007513 acids Chemical class 0.000 title claims abstract 3
- 239000003054 catalyst Substances 0.000 claims abstract description 54
- 239000000463 material Substances 0.000 claims abstract description 12
- 230000003197 catalytic effect Effects 0.000 claims abstract description 10
- 239000000376 reactant Substances 0.000 claims abstract description 10
- 238000000034 method Methods 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 229910017052 cobalt Inorganic materials 0.000 claims description 5
- 239000010941 cobalt Chemical group 0.000 claims description 5
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical group [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 3
- 229910001882 dioxygen Inorganic materials 0.000 claims description 3
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical group [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052772 Samarium Inorganic materials 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- 229910052787 antimony Inorganic materials 0.000 claims description 2
- 229910052785 arsenic Inorganic materials 0.000 claims description 2
- 239000011248 coating agent Substances 0.000 claims description 2
- 238000000576 coating method Methods 0.000 claims description 2
- 229910052738 indium Inorganic materials 0.000 claims description 2
- 229910052748 manganese Inorganic materials 0.000 claims description 2
- 239000011572 manganese Chemical group 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical group [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims 4
- 229910052759 nickel Inorganic materials 0.000 claims 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical group [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 1
- 150000001342 alkaline earth metals Chemical class 0.000 claims 1
- 229910052749 magnesium Inorganic materials 0.000 claims 1
- 239000011777 magnesium Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- 150000001336 alkenes Chemical class 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- 241000282326 Felis catus Species 0.000 description 2
- 235000014676 Phragmites communis Nutrition 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- STNJBCKSHOAVAJ-UHFFFAOYSA-N Methacrolein Chemical compound CC(=C)C=O STNJBCKSHOAVAJ-UHFFFAOYSA-N 0.000 description 1
- 101100238304 Mus musculus Morc1 gene Proteins 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- IOVGROKTTNBUGK-SJCJKPOMSA-N ritodrine Chemical compound N([C@@H](C)[C@H](O)C=1C=CC(O)=CC=1)CCC1=CC=C(O)C=C1 IOVGROKTTNBUGK-SJCJKPOMSA-N 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
Classifications
-
- 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
-
- 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
-
- 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
- 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
-
- 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
-
- 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
- B01J2208/00256—Controlling the temperature by indirect heat exchange with heat exchange elements outside the bed of solid particles in a heat exchanger for the heat exchange medium separate from the reactor
-
- 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
- B01J2208/00796—Details of the reactor or of the particulate material
- B01J2208/00823—Mixing elements
- B01J2208/00858—Moving elements
- B01J2208/00876—Moving elements outside the bed, e.g. rotary mixer
-
- 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
- B01J2523/00—Constitutive chemical elements of heterogeneous catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US57012675A | 1975-04-21 | 1975-04-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1065341A true CA1065341A (en) | 1979-10-30 |
Family
ID=24278352
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA246,905A Expired CA1065341A (en) | 1975-04-21 | 1976-03-02 | Oxidation of propylene and isobutylene to obtain the corresponding unsaturated aldehydes and acids |
Country Status (20)
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1523772A (en) * | 1974-07-22 | 1978-09-06 | Standard Oil Co | Oxidation catalysts |
| CA1133505A (en) * | 1977-07-28 | 1982-10-12 | Andrew T. Guttmann | Process for the oxidation of olefins |
| IL55073A (en) * | 1977-07-28 | 1982-01-31 | Standard Oil Co | Catalysts for the oxidation and ammoxidation of olefins |
| JPS5517306A (en) * | 1978-07-20 | 1980-02-06 | Standard Oil Co | Olefin oxidation using catalyst containing various promoter elements |
| DE3125061C2 (de) * | 1981-06-26 | 1984-03-15 | Degussa Ag, 6000 Frankfurt | Verfahren zur Herstellung von Acrolein bzw. Methacrolein durch katalytische Oxidation von Propylen bzw. Isobutylen oder tertiär-Butanol in sauerstoffhaltigen Gasgemischen |
| US5276178A (en) * | 1989-12-06 | 1994-01-04 | Nippon Shokubai Co., Ltd. | Process for producing methacrolein and methacrylic acid |
| JPH0784400B2 (ja) * | 1990-04-03 | 1995-09-13 | 株式会社日本触媒 | 不飽和アルデヒドおよび不飽和酸の製造方法 |
| EP0460932B1 (en) * | 1990-06-06 | 1995-05-17 | MITSUI TOATSU CHEMICALS, Inc. | Method for preparing acrolein or methacrolein |
| DE4023239A1 (de) * | 1990-07-21 | 1992-01-23 | Basf Ag | Verfahren zur katalytischen gasphasenoxidation von propen oder iso-buten zu acrolein oder methacrolein |
| US5245083A (en) * | 1991-02-27 | 1993-09-14 | Mitsui Toatsu Chemicals, Inc. | Method for preparing methacrolein and method for preparing a catalyst for use in the preparation of methacrolein |
| DE4132263A1 (de) * | 1991-09-27 | 1993-04-01 | Basf Ag | Verfahren zur katalytischen gasphasenoxidation von acrolein zu acrylsaeure |
| DE4431957A1 (de) * | 1994-09-08 | 1995-03-16 | Basf Ag | Verfahren zur katalytischen Gasphasenoxidation von Propen zu Acrolein |
| JP3943311B2 (ja) | 2000-05-19 | 2007-07-11 | 株式会社日本触媒 | 不飽和アルデヒドおよび不飽和カルボン酸の製造方法 |
| JP4867129B2 (ja) | 2003-12-15 | 2012-02-01 | 三菱化学株式会社 | （メタ）アクリル酸または（メタ）アクロレインの製造方法 |
| JP2005213179A (ja) * | 2004-01-29 | 2005-08-11 | Mitsubishi Rayon Co Ltd | 触媒層およびその形成方法、固定床管型反応器、メタクロレインまたはメタクリル酸の製造方法 |
| US20050171365A1 (en) * | 2004-02-03 | 2005-08-04 | Grey Roger A. | Epoxidation process using a mixed catalyst system |
| JP5130562B2 (ja) * | 2007-11-06 | 2013-01-30 | 日本化薬株式会社 | メタクロレイン及び／又はメタクリル酸の製造方法 |
| JP2020093216A (ja) * | 2018-12-12 | 2020-06-18 | 株式会社Ihi | 触媒反応装置 |
-
1976
- 1976-02-26 IN IN346/CAL/1976A patent/IN142430B/en unknown
- 1976-02-27 GB GB7799/76A patent/GB1529384A/en not_active Expired
- 1976-03-02 CA CA246,905A patent/CA1065341A/en not_active Expired
- 1976-03-03 MX MX100287U patent/MX3250E/es unknown
- 1976-03-12 IT IT7621175A patent/IT1058418B/it active
- 1976-03-17 DE DE19762611249 patent/DE2611249A1/de not_active Withdrawn
- 1976-03-18 ES ES446290A patent/ES446290A1/es not_active Expired
- 1976-03-19 YU YU00728/76A patent/YU72876A/xx unknown
- 1976-03-19 PT PT64923A patent/PT64923B/pt unknown
- 1976-03-22 CH CH355076A patent/CH619442A5/de not_active IP Right Cessation
- 1976-03-24 BE BE165496A patent/BE839955A/xx unknown
- 1976-04-07 AT AT252676A patent/AT343091B/de not_active IP Right Cessation
- 1976-04-10 RO RO7685580A patent/RO69673A/ro unknown
- 1976-04-12 JP JP51041165A patent/JPS51127013A/ja active Pending
- 1976-04-15 FR FR7611259A patent/FR2308609A1/fr active Granted
- 1976-04-19 DD DD192421A patent/DD124592A5/xx unknown
- 1976-04-20 NL NL7604153A patent/NL7604153A/xx not_active Application Discontinuation
- 1976-04-20 NO NO761326A patent/NO146707C/no unknown
- 1976-04-20 BR BR2429/76A patent/BR7602429A/pt unknown
- 1976-04-21 CS CS762622A patent/CS193541B2/cs unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL7604153A (nl) | 1976-10-25 |
| NO761326L (enrdf_load_html_response) | 1976-10-22 |
| FR2308609A1 (fr) | 1976-11-19 |
| NO146707C (no) | 1982-11-24 |
| PT64923A (en) | 1976-04-01 |
| DD124592A5 (de) | 1977-03-02 |
| CH619442A5 (en) | 1980-09-30 |
| YU72876A (en) | 1982-05-31 |
| BR7602429A (pt) | 1976-10-19 |
| ES446290A1 (es) | 1977-06-16 |
| JPS51127013A (en) | 1976-11-05 |
| IT1058418B (it) | 1982-04-10 |
| ATA252676A (de) | 1977-09-15 |
| BE839955A (fr) | 1976-07-16 |
| IN142430B (enrdf_load_html_response) | 1977-07-09 |
| PT64923B (en) | 1977-08-24 |
| GB1529384A (en) | 1978-10-18 |
| CS193541B2 (en) | 1979-10-31 |
| DE2611249A1 (de) | 1976-11-04 |
| NO146707B (no) | 1982-08-16 |
| RO69673A (ro) | 1981-08-17 |
| MX3250E (es) | 1980-08-06 |
| AT343091B (de) | 1978-05-10 |
| FR2308609B1 (enrdf_load_html_response) | 1980-10-03 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1065341A (en) | Oxidation of propylene and isobutylene to obtain the corresponding unsaturated aldehydes and acids | |
| CA1048481A (en) | Chromium-containing catalysts useful for oxidation reactions | |
| KR100419705B1 (ko) | 촉매및불포화알데히드및불포화산의제조방법 | |
| US5198581A (en) | Process for producing unsaturated aldehydes and unsaturated acids | |
| KR100487883B1 (ko) | 아크롤레인및아크릴산의제조방법 | |
| US5144091A (en) | Preparation of acrolein or methacrolein by actalytic gas-phase oxidation of propene or isobutene | |
| US5276178A (en) | Process for producing methacrolein and methacrylic acid | |
| US5153162A (en) | Catalyst for the production of methacrylic acid | |
| CN101495229B (zh) | 多金属氧化物催化剂及采用该催化剂制备(甲基)丙烯酸的方法 | |
| JPS5946132A (ja) | メタクロレイン合成用触媒 | |
| JP2008535784A (ja) | 不飽和アルデヒド及び／または不飽和酸の製造法 | |
| CS226406B2 (en) | Method of preparing methacrolein and methacrylic acid | |
| US11084029B2 (en) | Catalyst, acrylic acid production method, and catalyst production method | |
| KR20050067096A (ko) | 불포화 알데히드 및/또는 불포화 지방산의 제조방법 | |
| KR102618400B1 (ko) | 촉매 및 그의 제조 방법, 그리고 당해 촉매를 이용한 직결 2단 접촉 기상 산화 방법 및 그의 이용 | |
| JP2001011010A (ja) | メタクリル酸の製造方法 | |
| BRPI0809545B1 (pt) | "processes for loading a longitudinal section of a catalytic tube with a uniform fixed catalytic layer section, and for hexedly catalyzed partial gas stage oxidation of an organic compound in a tube beam reactor, and tube beam reactor " | |
| US3919257A (en) | Catalytic vapor phase oxidation of n-butene to maleic anhydride using two different catalysts maintained in two distinct and separate portions of the reaction zone | |
| BRPI0802625B1 (pt) | método para preparar aldeído não-saturado e/ou ácido graxo não-saturado usando reator de oxidação parcial catalítica de leito fixo | |
| US3883573A (en) | Commercial fixed-bed acrylonitrile or methacrylonitrile | |
| DE3365122D1 (en) | Catalysts, their preparation and use in vapour phase oxidation of unsaturated aldehydes | |
| RU2646601C2 (ru) | Катализаторная компоновка с оптимизированной порозностью для получения фталевого ангидрида | |
| JP3502526B2 (ja) | バナジウム−リン系酸化物、その製造方法、該酸化物からなる気相酸化用触媒および炭化水素類の部分気相酸化方法 | |
| JP7551026B2 (ja) | 不飽和アルデヒドの製造方法および不飽和アルデヒドの製造装置 | |
| GB2037604A (en) | Process for producing methacrylic acid |