DE2748050C2 - Verfahren zur Herstellung von Methacrylsäure - Google Patents
Verfahren zur Herstellung von MethacrylsäureInfo
- Publication number
- DE2748050C2 DE2748050C2 DE2748050A DE2748050A DE2748050C2 DE 2748050 C2 DE2748050 C2 DE 2748050C2 DE 2748050 A DE2748050 A DE 2748050A DE 2748050 A DE2748050 A DE 2748050A DE 2748050 C2 DE2748050 C2 DE 2748050C2
- Authority
- DE
- Germany
- Prior art keywords
- methacrolein
- oxidation
- methacrylic acid
- stage
- mol
- 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
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 title claims description 64
- 238000000034 method Methods 0.000 title claims description 29
- 238000002360 preparation method Methods 0.000 title claims description 3
- 238000007254 oxidation reaction Methods 0.000 claims description 94
- 230000003647 oxidation Effects 0.000 claims description 87
- STNJBCKSHOAVAJ-UHFFFAOYSA-N Methacrolein Chemical compound CC(=C)C=O STNJBCKSHOAVAJ-UHFFFAOYSA-N 0.000 claims description 82
- 238000000926 separation method Methods 0.000 claims description 38
- 239000000203 mixture Substances 0.000 claims description 31
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 21
- 239000007789 gas Substances 0.000 claims description 19
- 239000002904 solvent Substances 0.000 claims description 13
- 238000010521 absorption reaction Methods 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 10
- 230000003197 catalytic effect Effects 0.000 claims description 10
- 239000007795 chemical reaction product Substances 0.000 claims description 6
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 5
- 229910001882 dioxygen Inorganic materials 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 description 43
- 239000003054 catalyst Substances 0.000 description 19
- 239000011541 reaction mixture Substances 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
- 239000006227 byproduct Substances 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 4
- 230000003247 decreasing effect Effects 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- 239000001569 carbon dioxide Substances 0.000 description 3
- 229910002091 carbon monoxide Inorganic materials 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 239000011261 inert gas Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 229910052684 Cerium Inorganic materials 0.000 description 2
- 229910052779 Neodymium Inorganic materials 0.000 description 2
- 229910052770 Uranium Inorganic materials 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 229910052785 arsenic Inorganic materials 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- 229910052793 cadmium Inorganic materials 0.000 description 2
- 229910052804 chromium Inorganic materials 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 229910052732 germanium Inorganic materials 0.000 description 2
- 229910052738 indium Inorganic materials 0.000 description 2
- 229910052745 lead Inorganic materials 0.000 description 2
- 229910052748 manganese Inorganic materials 0.000 description 2
- 229910052758 niobium Inorganic materials 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 229910052714 tellurium Inorganic materials 0.000 description 2
- 229910052718 tin Inorganic materials 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- 229910052720 vanadium Inorganic materials 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 229910052726 zirconium Inorganic materials 0.000 description 2
- 229910017061 Fe Co Inorganic materials 0.000 description 1
- 229910052772 Samarium Inorganic materials 0.000 description 1
- 229910052776 Thorium Inorganic materials 0.000 description 1
- 239000003570 air Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- 229910052790 beryllium Inorganic materials 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- 229910052716 thallium Inorganic materials 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/48—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP12866576A JPS5353613A (en) | 1976-10-26 | 1976-10-26 | Preparation of methacrylic acid |
Publications (2)
Publication Number | Publication Date |
---|---|
DE2748050A1 DE2748050A1 (de) | 1978-04-27 |
DE2748050C2 true DE2748050C2 (de) | 1987-03-05 |
Family
ID=14990407
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE2748050A Expired DE2748050C2 (de) | 1976-10-26 | 1977-10-26 | Verfahren zur Herstellung von Methacrylsäure |
Country Status (4)
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5632149Y2 (US20020128544A1-20020912-P00008.png) * | 1978-04-11 | 1981-07-31 | ||
JPS55124734A (en) * | 1979-03-22 | 1980-09-26 | Nippon Kayaku Co Ltd | Preparation of methacrylic acid |
JPS57144237A (en) * | 1981-03-04 | 1982-09-06 | Japan Synthetic Rubber Co Ltd | Preparation of methacrylic acid |
US4838081A (en) * | 1986-02-28 | 1989-06-13 | Nabisco Brands, Inc. | Method and apparatus for improving the reliability for dough testing results |
DE4132684A1 (de) * | 1991-10-01 | 1993-04-08 | Basf Ag | Verfahren zur katalytischen gasphasenoxidation von methacrolein zu methacrylsaeure |
US6339037B1 (en) * | 1999-04-27 | 2002-01-15 | Nippon Shokubai Co. Ltd | Catalysts for methacrylic acid production and process for producing methacrylic acid |
US20090124825A1 (en) * | 2007-11-14 | 2009-05-14 | Shanghai Huayi Acrylic Acid Co., Ltd | Method of (meth) acrylate production |
JP6482941B2 (ja) * | 2015-04-28 | 2019-03-13 | 株式会社日本触媒 | 熱交換型反応システムおよびそれを用いた反応方法 |
Family Cites Families (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2693474A (en) * | 1954-11-02 | Oxidation of olefins | ||
FR1295188A (fr) * | 1961-07-17 | 1962-06-01 | Shell Int Research | Procédé de préparation d'acides monocarboxyliques non saturés à partir d'oléfines |
US3686294A (en) * | 1970-10-06 | 1972-08-22 | Japanese Geon Co Ltd | Process for the production of methacrylic acid |
JPS5750765B2 (US20020128544A1-20020912-P00008.png) * | 1972-12-29 | 1982-10-28 | ||
JPS5316843B2 (US20020128544A1-20020912-P00008.png) * | 1973-06-05 | 1978-06-03 | ||
JPS549369B2 (US20020128544A1-20020912-P00008.png) * | 1973-07-05 | 1979-04-24 | ||
JPS5233614B2 (US20020128544A1-20020912-P00008.png) * | 1973-08-16 | 1977-08-30 | ||
US3976688A (en) * | 1973-11-26 | 1976-08-24 | Nippon Zeon Co., Ltd. | Process for preparing unsaturated carboxylic acids |
JPS50126605A (US20020128544A1-20020912-P00008.png) * | 1974-03-23 | 1975-10-04 | ||
GB1523772A (en) * | 1974-07-22 | 1978-09-06 | Standard Oil Co | Oxidation catalysts |
DE2436818C3 (de) * | 1974-07-31 | 1985-05-09 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung von Acrylsäure durch Oxidation von Propylen mit Sauerstoff enthaltenden Gasen in zwei getrennten Oxidationsstufen |
JPS5148609A (ja) * | 1974-10-23 | 1976-04-26 | Asahi Glass Co Ltd | Nidansankanyoruisopuchirenkarano metaku |
GB1490683A (en) * | 1975-03-12 | 1977-11-02 | Mitsubishi Rayon Co | Process and a catalyst for producing unsaturated aldehydes unsaturated carboxylic acids or conjugated diene |
US4049577A (en) * | 1975-12-15 | 1977-09-20 | The Dow Chemical Company | Catalyst for making acrolein |
DE2735414A1 (de) * | 1976-08-06 | 1978-02-09 | Nippon Zeon Co | Oxydation von olefinen |
-
1976
- 1976-10-26 JP JP12866576A patent/JPS5353613A/ja active Granted
-
1977
- 1977-10-26 FR FR7732202A patent/FR2369238A1/fr active Granted
- 1977-10-26 DE DE2748050A patent/DE2748050C2/de not_active Expired
-
1979
- 1979-04-16 US US06/030,647 patent/US4564703A/en not_active Expired - Lifetime
Non-Patent Citations (1)
Title |
---|
NICHTS-ERMITTELT |
Also Published As
Publication number | Publication date |
---|---|
JPS5353613A (en) | 1978-05-16 |
US4564703A (en) | 1986-01-14 |
JPS5625219B2 (US20020128544A1-20020912-P00008.png) | 1981-06-11 |
FR2369238A1 (fr) | 1978-05-26 |
DE2748050A1 (de) | 1978-04-27 |
FR2369238B1 (US20020128544A1-20020912-P00008.png) | 1983-10-28 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
8110 | Request for examination paragraph 44 | ||
8127 | New person/name/address of the applicant |
Owner name: NIPPON SHOKUBAI KAGAKU KOGYO CO. LTD., OSAKA, JP |
|
8128 | New person/name/address of the agent |
Representative=s name: ZUMSTEIN, F., DIPL.-CHEM. DR.RER.NAT. ASSMANN, E., |
|
D2 | Grant after examination | ||
8364 | No opposition during term of opposition | ||
8339 | Ceased/non-payment of the annual fee |