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)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Materials Engineering (AREA)
- Oil, Petroleum & Natural Gas (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 |
| IL55073A (en) * | 1977-07-28 | 1982-01-31 | Standard Oil Co | Catalysts for the oxidation and ammoxidation of olefins |
| CA1133505A (en) * | 1977-07-28 | 1982-10-12 | Andrew T. Guttmann | Process for the oxidation 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 |
| KR950006522B1 (ko) * | 1989-12-06 | 1995-06-16 | 가부시끼가이샤 닛뽕쇼꾸바이 | 메타크롤레인 및 메타크릴산의 제조방법 |
| 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 |
| KR950004031B1 (ko) * | 1991-02-27 | 1995-04-22 | 미쓰이도오아쓰가가꾸 가부시끼가이샤 | 메타크롤레인의 제조방법 및 메타크롤레인의 제조에 사용하는 촉매의 제조방법 |
| 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 PT PT64923A patent/PT64923B/pt unknown
- 1976-03-19 YU YU00728/76A patent/YU72876A/xx 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 BR BR2429/76A patent/BR7602429A/pt unknown
- 1976-04-20 NO NO761326A patent/NO146707C/no unknown
- 1976-04-20 NL NL7604153A patent/NL7604153A/xx not_active Application Discontinuation
- 1976-04-21 CS CS762622A patent/CS193541B2/cs unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DD124592A5 (de) | 1977-03-02 |
| BR7602429A (pt) | 1976-10-19 |
| YU72876A (en) | 1982-05-31 |
| RO69673A (ro) | 1981-08-17 |
| MX3250E (es) | 1980-08-06 |
| GB1529384A (en) | 1978-10-18 |
| PT64923B (en) | 1977-08-24 |
| ES446290A1 (es) | 1977-06-16 |
| NO761326L (enrdf_load_stackoverflow) | 1976-10-22 |
| FR2308609B1 (enrdf_load_stackoverflow) | 1980-10-03 |
| PT64923A (en) | 1976-04-01 |
| FR2308609A1 (fr) | 1976-11-19 |
| NO146707B (no) | 1982-08-16 |
| IT1058418B (it) | 1982-04-10 |
| NL7604153A (nl) | 1976-10-25 |
| CH619442A5 (en) | 1980-09-30 |
| CS193541B2 (en) | 1979-10-31 |
| ATA252676A (de) | 1977-09-15 |
| DE2611249A1 (de) | 1976-11-04 |
| IN142430B (enrdf_load_stackoverflow) | 1977-07-09 |
| BE839955A (fr) | 1976-07-16 |
| AT343091B (de) | 1978-05-10 |
| JPS51127013A (en) | 1976-11-05 |
| NO146707C (no) | 1982-11-24 |
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