DE2706583C3 - Verfahren zur Herstellung von Methacrylsäure - Google Patents
Verfahren zur Herstellung von MethacrylsäureInfo
- Publication number
- DE2706583C3 DE2706583C3 DE2706583A DE2706583A DE2706583C3 DE 2706583 C3 DE2706583 C3 DE 2706583C3 DE 2706583 A DE2706583 A DE 2706583A DE 2706583 A DE2706583 A DE 2706583A DE 2706583 C3 DE2706583 C3 DE 2706583C3
- Authority
- DE
- Germany
- Prior art keywords
- oxidation
- methacrolein
- acetic acid
- methacrylic
- weight
- 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 34
- 238000000034 method Methods 0.000 title claims description 24
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 238000007254 oxidation reaction Methods 0.000 claims description 44
- 230000003647 oxidation Effects 0.000 claims description 43
- 239000003960 organic solvent Substances 0.000 claims description 6
- 239000007791 liquid phase Substances 0.000 claims description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 2
- 229910052782 aluminium Inorganic materials 0.000 claims description 2
- 150000004767 nitrides Chemical class 0.000 claims 1
- 239000011949 solid catalyst Substances 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 81
- 238000006243 chemical reaction Methods 0.000 description 22
- 150000001299 aldehydes Chemical class 0.000 description 18
- 230000015572 biosynthetic process Effects 0.000 description 15
- 239000003054 catalyst Substances 0.000 description 15
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 13
- 239000001301 oxygen Substances 0.000 description 13
- 229910052760 oxygen Inorganic materials 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 238000006116 polymerization reaction Methods 0.000 description 11
- 239000007789 gas Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- 239000003112 inhibitor Substances 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 4
- 239000002638 heterogeneous catalyst Substances 0.000 description 4
- UZFMOKQJFYMBGY-UHFFFAOYSA-N 4-hydroxy-TEMPO Chemical group CC1(C)CC(O)CC(C)(C)N1[O] UZFMOKQJFYMBGY-UHFFFAOYSA-N 0.000 description 3
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- STNJBCKSHOAVAJ-UHFFFAOYSA-N Methacrolein Chemical compound CC(=C)C=O STNJBCKSHOAVAJ-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- QPJMZUYYHWNDIX-UHFFFAOYSA-N [Co][Fe][Bi][Mo] Chemical compound [Co][Fe][Bi][Mo] QPJMZUYYHWNDIX-UHFFFAOYSA-N 0.000 description 2
- KGGZTXSNARMULX-UHFFFAOYSA-L copper;dicarbamodithioate Chemical compound [Cu+2].NC([S-])=S.NC([S-])=S KGGZTXSNARMULX-UHFFFAOYSA-L 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- NRTOMJZYCJJWKI-UHFFFAOYSA-N Titanium nitride Chemical compound [Ti]#N NRTOMJZYCJJWKI-UHFFFAOYSA-N 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- JXOOCQBAIRXOGG-UHFFFAOYSA-N [B].[B].[B].[B].[B].[B].[B].[B].[B].[B].[B].[B].[Al] Chemical compound [B].[B].[B].[B].[B].[B].[B].[B].[B].[B].[B].[B].[Al] JXOOCQBAIRXOGG-UHFFFAOYSA-N 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- CFJRGWXELQQLSA-UHFFFAOYSA-N azanylidyneniobium Chemical compound [Nb]#N CFJRGWXELQQLSA-UHFFFAOYSA-N 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- XTDAIYZKROTZLD-UHFFFAOYSA-N boranylidynetantalum Chemical compound [Ta]#B XTDAIYZKROTZLD-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- PMHQVHHXPFUNSP-UHFFFAOYSA-M copper(1+);methylsulfanylmethane;bromide Chemical compound Br[Cu].CSC PMHQVHHXPFUNSP-UHFFFAOYSA-M 0.000 description 1
- ZNRKKSGNBIJSRT-UHFFFAOYSA-L dibromotantalum Chemical compound Br[Ta]Br ZNRKKSGNBIJSRT-UHFFFAOYSA-L 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- WHJFNYXPKGDKBB-UHFFFAOYSA-N hafnium;methane Chemical compound C.[Hf] WHJFNYXPKGDKBB-UHFFFAOYSA-N 0.000 description 1
- 239000002815 homogeneous catalyst Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- UNASZPQZIFZUSI-UHFFFAOYSA-N methylidyneniobium Chemical compound [Nb]#C UNASZPQZIFZUSI-UHFFFAOYSA-N 0.000 description 1
- DOTMOQHOJINYBL-UHFFFAOYSA-N molecular nitrogen;molecular oxygen Chemical compound N#N.O=O DOTMOQHOJINYBL-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- MTPVUVINMAGMJL-UHFFFAOYSA-N trimethyl(1,1,2,2,2-pentafluoroethyl)silane Chemical compound C[Si](C)(C)C(F)(F)C(F)(F)F MTPVUVINMAGMJL-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
- ZVWKZXLXHLZXLS-UHFFFAOYSA-N zirconium nitride Chemical compound [Zr]#N ZVWKZXLXHLZXLS-UHFFFAOYSA-N 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polymerisation Methods In General (AREA)
- Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU762325546A SU1310384A1 (ru) | 1976-02-20 | 1976-02-20 | Способ получени метакриловой кислоты |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2706583A1 DE2706583A1 (de) | 1977-08-25 |
| DE2706583B2 DE2706583B2 (de) | 1979-11-15 |
| DE2706583C3 true DE2706583C3 (de) | 1980-07-24 |
Family
ID=20649252
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2706583A Expired DE2706583C3 (de) | 1976-02-20 | 1977-02-16 | Verfahren zur Herstellung von Methacrylsäure |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4127603A (enExample) |
| JP (1) | JPS52116411A (enExample) |
| DE (1) | DE2706583C3 (enExample) |
| FR (1) | FR2341552A1 (enExample) |
| SU (1) | SU1310384A1 (enExample) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4234519A (en) * | 1979-01-26 | 1980-11-18 | Halcon Research And Development Corp. | Recovery of methacrolein |
| JPS56140815U (enExample) * | 1980-03-24 | 1981-10-24 | ||
| JPS5741715A (en) * | 1980-08-23 | 1982-03-09 | Fuji Electric Co Ltd | Temperature control system of goods storing equipment |
| JPS5784014U (enExample) * | 1980-11-06 | 1982-05-24 | ||
| JPS57203234U (enExample) * | 1981-06-23 | 1982-12-24 | ||
| ATE49588T1 (de) * | 1984-10-10 | 1990-02-15 | Amoco Corp | Verfahren zur reinigung von methacrylsaeure. |
| JPS63196917A (ja) * | 1987-02-10 | 1988-08-15 | Mitsubishi Heavy Ind Ltd | 室温コントロ−ラ |
| US5322960A (en) * | 1993-04-15 | 1994-06-21 | Nippon Shokubai Co., Ltd. | Method for inhibiting polymerization of (meth) acrylic acid and esters thereof |
| TW294658B (enExample) * | 1994-06-02 | 1997-01-01 | Nippon Catalytic Chem Ind | |
| US5728872A (en) * | 1994-06-27 | 1998-03-17 | Lutz Riemenschneider | Stabilized acrylic acid compositions |
| CZ290225B6 (cs) * | 1996-05-27 | 2002-06-12 | Mitsubishi Chemical Corporation | Způsob inhibice polymerace kyseliny (meth)akrylové a jejich esterů |
| JP4238962B2 (ja) * | 1998-03-03 | 2009-03-18 | 日本ゼオン株式会社 | 重合防止性組成物、重合防止剤、及び重合防止方法 |
| KR100417098B1 (ko) | 1998-07-27 | 2004-02-05 | 니폰 쇼쿠바이 컴파니 리미티드 | 비닐 화합물의 중합 억제 방법 |
| JP4687843B2 (ja) * | 2000-12-12 | 2011-05-25 | 三菱瓦斯化学株式会社 | メタクリル酸の精製方法 |
| WO2005118518A1 (ja) * | 2004-06-02 | 2005-12-15 | Mitsubishi Rayon Co., Ltd. | α，β－不飽和カルボン酸の製造方法 |
| US7649112B2 (en) | 2005-07-25 | 2010-01-19 | Saudi Basic Industries Corporation | Integrated plant for producing 2-ethyl-hexanol and methacrylic acid and a method based thereon |
| US7851397B2 (en) | 2005-07-25 | 2010-12-14 | Saudi Basic Industries Corporation | Catalyst for methacrolein oxidation and method for making and using same |
| US7649111B2 (en) | 2005-07-25 | 2010-01-19 | Saudi Basic Industries Corporation | Catalyst for the oxidation of a mixed aldehyde feedstock to methacrylic acid and methods for making and using same |
| US7732367B2 (en) | 2005-07-25 | 2010-06-08 | Saudi Basic Industries Corporation | Catalyst for methacrolein oxidation and method for making and using same |
| EP1995232B1 (en) * | 2007-05-25 | 2018-01-03 | Evonik Röhm GmbH | Use of feed compositions in preparation of methacrylic acid by oxidation |
| US8921257B2 (en) | 2011-12-02 | 2014-12-30 | Saudi Basic Industries Corporation | Dual function partial oxidation catalyst for propane to acrylic acid conversion |
| US8722940B2 (en) | 2012-03-01 | 2014-05-13 | Saudi Basic Industries Corporation | High molybdenum mixed metal oxide catalysts for the production of unsaturated aldehydes from olefins |
| JPWO2020241720A1 (enExample) * | 2019-05-31 | 2020-12-03 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE625848A (enExample) * | ||||
| GB1088099A (en) * | 1963-10-31 | 1967-10-18 | Mitsubishi Petrochemical Co | Catalytic oxidation of unsaturated aldehydes |
-
1976
- 1976-02-20 SU SU762325546A patent/SU1310384A1/ru active
-
1977
- 1977-02-16 DE DE2706583A patent/DE2706583C3/de not_active Expired
- 1977-02-16 US US05/769,117 patent/US4127603A/en not_active Expired - Lifetime
- 1977-02-21 FR FR7704931A patent/FR2341552A1/fr active Granted
- 1977-02-21 JP JP1858477A patent/JPS52116411A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS52116411A (en) | 1977-09-29 |
| JPS543853B2 (enExample) | 1979-02-27 |
| DE2706583A1 (de) | 1977-08-25 |
| FR2341552B1 (enExample) | 1980-02-15 |
| SU1310384A1 (ru) | 1987-05-15 |
| DE2706583B2 (de) | 1979-11-15 |
| FR2341552A1 (fr) | 1977-09-16 |
| US4127603A (en) | 1978-11-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| C3 | Grant after two publication steps (3rd publication) | ||
| 8328 | Change in the person/name/address of the agent |
Free format text: VON FUENER, A., DIPL.-CHEM. DR.RER.NAT. EBBINGHAUS, D., DIPL.-ING., PAT.-ANW., 8000 MUENCHEN |
|
| 8339 | Ceased/non-payment of the annual fee |