GB1390271A - Process for the oxidation of olefins to aldehydes and acids - Google Patents
Process for the oxidation of olefins to aldehydes and acidsInfo
- Publication number
- GB1390271A GB1390271A GB524672A GB524672A GB1390271A GB 1390271 A GB1390271 A GB 1390271A GB 524672 A GB524672 A GB 524672A GB 524672 A GB524672 A GB 524672A GB 1390271 A GB1390271 A GB 1390271A
- Authority
- GB
- United Kingdom
- Prior art keywords
- weight per
- per cent
- phosphorus
- constituent
- silica
- 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
- 238000000034 method Methods 0.000 title abstract 3
- 230000003647 oxidation Effects 0.000 title abstract 3
- 238000007254 oxidation reaction Methods 0.000 title abstract 3
- 150000001336 alkenes Chemical class 0.000 title abstract 2
- 239000002253 acid Substances 0.000 title 1
- 150000007513 acids Chemical class 0.000 title 1
- 150000001299 aldehydes Chemical class 0.000 title 1
- 239000003054 catalyst Substances 0.000 abstract 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 abstract 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract 4
- 239000000470 constituent Substances 0.000 abstract 4
- 239000000203 mixture Substances 0.000 abstract 4
- 229910052698 phosphorus Inorganic materials 0.000 abstract 4
- 239000011574 phosphorus Substances 0.000 abstract 4
- 239000000377 silicon dioxide Substances 0.000 abstract 3
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 abstract 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 abstract 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 abstract 2
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 abstract 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 abstract 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 abstract 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 abstract 2
- 229910052785 arsenic Chemical group 0.000 abstract 2
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical group [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 abstract 2
- 229910052797 bismuth Inorganic materials 0.000 abstract 2
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 abstract 2
- 229910001882 dioxygen Inorganic materials 0.000 abstract 2
- 229910052742 iron Inorganic materials 0.000 abstract 2
- 239000011777 magnesium Substances 0.000 abstract 2
- 229910052749 magnesium Inorganic materials 0.000 abstract 2
- 239000000463 material Substances 0.000 abstract 2
- 229910052750 molybdenum Inorganic materials 0.000 abstract 2
- 239000011733 molybdenum Substances 0.000 abstract 2
- 239000003921 oil Substances 0.000 abstract 2
- 229910052700 potassium Inorganic materials 0.000 abstract 2
- 239000011591 potassium Substances 0.000 abstract 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 abstract 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 abstract 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 abstract 1
- STNJBCKSHOAVAJ-UHFFFAOYSA-N Methacrolein Chemical compound CC(=C)C=O STNJBCKSHOAVAJ-UHFFFAOYSA-N 0.000 abstract 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 150000004645 aluminates Chemical class 0.000 abstract 1
- ILRRQNADMUWWFW-UHFFFAOYSA-K aluminium phosphate Chemical compound O1[Al]2OP1(=O)O2 ILRRQNADMUWWFW-UHFFFAOYSA-K 0.000 abstract 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 abstract 1
- 229940001007 aluminium phosphate Drugs 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 150000001642 boronic acid derivatives Chemical class 0.000 abstract 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 abstract 1
- 239000003638 chemical reducing agent Substances 0.000 abstract 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 abstract 1
- 238000001125 extrusion Methods 0.000 abstract 1
- 229910052816 inorganic phosphate Inorganic materials 0.000 abstract 1
- 229910052901 montmorillonite Inorganic materials 0.000 abstract 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 239000008188 pellet Substances 0.000 abstract 1
- 239000000843 powder Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 abstract 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 abstract 1
- 239000008262 pumice Substances 0.000 abstract 1
- 150000004760 silicates Chemical class 0.000 abstract 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 abstract 1
- 229910010271 silicon carbide Inorganic materials 0.000 abstract 1
- 238000001694 spray drying Methods 0.000 abstract 1
Classifications
-
- 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
-
- 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
-
- 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
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/14—Phosphorus; Compounds thereof
- B01J27/186—Phosphorus; Compounds thereof with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J27/188—Phosphorus; Compounds thereof with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium with chromium, molybdenum, tungsten or polonium
- B01J27/19—Molybdenum
- B01J27/192—Molybdenum with bismuth
-
- 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
- B01J2523/00—Constitutive chemical elements of heterogeneous catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11278271A | 1971-02-04 | 1971-02-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1390271A true GB1390271A (en) | 1975-04-09 |
Family
ID=22345820
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB524672A Expired GB1390271A (en) | 1971-02-04 | 1972-02-04 | Process for the oxidation of olefins to aldehydes and acids |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS5623969B1 (enrdf_load_stackoverflow) |
| BE (1) | BE778914A (enrdf_load_stackoverflow) |
| CA (1) | CA982142A (enrdf_load_stackoverflow) |
| DE (1) | DE2203710C3 (enrdf_load_stackoverflow) |
| FR (1) | FR2124424B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1390271A (enrdf_load_stackoverflow) |
| IT (1) | IT948061B (enrdf_load_stackoverflow) |
| LU (1) | LU64718A1 (enrdf_load_stackoverflow) |
| NL (1) | NL179900C (enrdf_load_stackoverflow) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4186152A (en) * | 1976-08-06 | 1980-01-29 | Nippon Zeon Co., Ltd. | Oxidation of olefins |
| EP0442156A1 (en) | 1990-02-14 | 1991-08-21 | Luis Antonio Ruiz | Automatic corneal shaper |
| US5218146A (en) * | 1987-05-27 | 1993-06-08 | Nippon Shokubai Kagaku Kogyo Co., Ltd. | Process for production of acrylic acid |
| US6383973B1 (en) | 1999-05-25 | 2002-05-07 | Nippon Shokusai Co. Ltd. | Complex oxide catalysts and process for producing (meth) acrolein and (meth) acrylic acid |
| US6399818B2 (en) | 2000-05-19 | 2002-06-04 | Nippon Shokubai Co. Ltd. | Process for producing unsaturated aldehydes and unsaturated carboxylic acids |
| US7850928B2 (en) | 2001-01-25 | 2010-12-14 | Nippon Shokubai Co., Ltd. | Fixed-bed shell-and-tube reactor and its usage |
| CN114425379A (zh) * | 2020-10-15 | 2022-05-03 | 中国石油化工股份有限公司 | 一种丙烯氧化制备丙烯醛的催化剂及其制备方法和应用 |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4359401A (en) * | 1981-01-26 | 1982-11-16 | Ashland Oil, Inc. | Method of regeneration of an iron phosphate-type catalyst |
| JPS60217303A (ja) * | 1984-04-13 | 1985-10-30 | Mitsubishi Electric Corp | ホログラム封止体 |
| US5349109A (en) * | 1991-06-04 | 1994-09-20 | The Board Of Regents Of The University Of Oklahoma | Molybdenum-catalyzed amination of olefins |
| JP4242597B2 (ja) | 2002-02-28 | 2009-03-25 | 株式会社日本触媒 | 不飽和アルデヒド合成用触媒とその製造方法、およびその触媒を用いた不飽和アルデヒドの製造方法 |
| WO2010001732A1 (ja) | 2008-06-30 | 2010-01-07 | 株式会社日本触媒 | 固定床多管式反応器への固体粒状物の充填方法 |
| JP2011121048A (ja) | 2009-12-09 | 2011-06-23 | Rohm & Haas Co | 固体触媒物質をブレンドし、管状構造物に装填する方法 |
| JP6401391B2 (ja) | 2014-11-24 | 2018-10-10 | スリーディー システムズ インコーポレーテッド | ３ｄプリント用の液状ゴムを含むインク |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1125901B (de) * | 1959-12-19 | 1962-03-22 | Knapsack Ag | Verfahren zur Herstellung von Acrolein |
| DE1204659B (de) * | 1960-04-16 | 1965-11-11 | Bayer Ag | Verfahren zur Herstellung von Acrylsaeure oder Methacrylsaeure durch Oxydation von Propylen oder Isobutylen |
| US3387038A (en) * | 1962-09-26 | 1968-06-04 | Du Pont | Process for oxidizing propylene and isobutylene to unsaturated aldehyde |
| BE637830A (enrdf_load_stackoverflow) * | 1962-09-26 | 1900-01-01 | ||
| DE1667209A1 (de) * | 1964-10-06 | 1969-09-18 | Nippon Kayaku Kk | Neue Katalysatoren zur Oxydation von Olefinen |
| US3522299A (en) * | 1965-11-17 | 1970-07-28 | Nippon Kayaku Kk | Process for the oxidation of olefins to aldehydes and acids and catalyst therefor |
| GB1182824A (en) * | 1967-05-04 | 1970-03-04 | Daicel Ltd | A Process for Preparing Unsaturated Aldehydes. |
| US3642930A (en) * | 1968-12-30 | 1972-02-15 | Standard Oil Co Ohio | Process for the manufacture of isoprene from isoamylenes and methyl butanols and catalyst therefor |
-
1972
- 1972-01-10 CA CA132,024A patent/CA982142A/en not_active Expired
- 1972-01-27 DE DE19722203710 patent/DE2203710C3/de not_active Expired
- 1972-02-01 JP JP1101672A patent/JPS5623969B1/ja active Pending
- 1972-02-02 IT IT2013872A patent/IT948061B/it active
- 1972-02-03 LU LU64718D patent/LU64718A1/xx unknown
- 1972-02-03 FR FR7203569A patent/FR2124424B1/fr not_active Expired
- 1972-02-03 BE BE778914A patent/BE778914A/xx not_active IP Right Cessation
- 1972-02-04 GB GB524672A patent/GB1390271A/en not_active Expired
- 1972-02-04 NL NL7201503A patent/NL179900C/xx not_active IP Right Cessation
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4186152A (en) * | 1976-08-06 | 1980-01-29 | Nippon Zeon Co., Ltd. | Oxidation of olefins |
| US5218146A (en) * | 1987-05-27 | 1993-06-08 | Nippon Shokubai Kagaku Kogyo Co., Ltd. | Process for production of acrylic acid |
| EP0442156A1 (en) | 1990-02-14 | 1991-08-21 | Luis Antonio Ruiz | Automatic corneal shaper |
| US6383973B1 (en) | 1999-05-25 | 2002-05-07 | Nippon Shokusai Co. Ltd. | Complex oxide catalysts and process for producing (meth) acrolein and (meth) acrylic acid |
| US6399818B2 (en) | 2000-05-19 | 2002-06-04 | Nippon Shokubai Co. Ltd. | Process for producing unsaturated aldehydes and unsaturated carboxylic acids |
| US7850928B2 (en) | 2001-01-25 | 2010-12-14 | Nippon Shokubai Co., Ltd. | Fixed-bed shell-and-tube reactor and its usage |
| CN114425379A (zh) * | 2020-10-15 | 2022-05-03 | 中国石油化工股份有限公司 | 一种丙烯氧化制备丙烯醛的催化剂及其制备方法和应用 |
| CN114425379B (zh) * | 2020-10-15 | 2024-01-26 | 中国石油化工股份有限公司 | 一种丙烯氧化制备丙烯醛的催化剂及其制备方法和应用 |
Also Published As
| Publication number | Publication date |
|---|---|
| BE778914A (fr) | 1972-08-03 |
| FR2124424A1 (enrdf_load_stackoverflow) | 1972-09-22 |
| JPS5623969B1 (enrdf_load_stackoverflow) | 1981-06-03 |
| LU64718A1 (enrdf_load_stackoverflow) | 1973-09-04 |
| NL179900C (nl) | 1986-12-01 |
| IT948061B (it) | 1973-05-30 |
| NL7201503A (enrdf_load_stackoverflow) | 1972-08-08 |
| DE2203710B2 (de) | 1981-07-30 |
| DE2203710A1 (de) | 1972-08-17 |
| DE2203710C3 (de) | 1988-05-26 |
| CA982142A (en) | 1976-01-20 |
| FR2124424B1 (enrdf_load_stackoverflow) | 1976-03-05 |
| NL179900B (nl) | 1986-07-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |