DE1768253A1 - Verfahren zur Herstellung von Methacrylsaeure - Google Patents
Verfahren zur Herstellung von MethacrylsaeureInfo
- Publication number
- DE1768253A1 DE1768253A1 DE19681768253 DE1768253A DE1768253A1 DE 1768253 A1 DE1768253 A1 DE 1768253A1 DE 19681768253 DE19681768253 DE 19681768253 DE 1768253 A DE1768253 A DE 1768253A DE 1768253 A1 DE1768253 A1 DE 1768253A1
- Authority
- DE
- Germany
- Prior art keywords
- alpha
- acid
- hydroxyisobutyric acid
- hydroxyisobutyric
- methacrylic acid
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 42
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 title claims description 29
- 238000004519 manufacturing process Methods 0.000 title description 5
- BWLBGMIXKSTLSX-UHFFFAOYSA-N 2-hydroxyisobutyric acid Chemical compound CC(C)(O)C(O)=O BWLBGMIXKSTLSX-UHFFFAOYSA-N 0.000 claims description 36
- NGEWQZIDQIYUNV-UHFFFAOYSA-N L-valinic acid Natural products CC(C)C(O)C(O)=O NGEWQZIDQIYUNV-UHFFFAOYSA-N 0.000 claims description 32
- 239000003054 catalyst Substances 0.000 claims description 20
- 230000018044 dehydration Effects 0.000 claims description 19
- 238000006297 dehydration reaction Methods 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 18
- 229910052751 metal Inorganic materials 0.000 claims description 17
- 239000002184 metal Substances 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 14
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 238000006116 polymerization reaction Methods 0.000 claims description 7
- 239000003112 inhibitor Substances 0.000 claims description 6
- 239000007791 liquid phase Substances 0.000 claims description 5
- 159000000000 sodium salts Chemical class 0.000 claims description 5
- 239000003570 air Substances 0.000 claims description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 4
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- -1 alkaline earth metal salt Chemical class 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 238000011065 in-situ storage Methods 0.000 claims description 2
- 229910000000 metal hydroxide Inorganic materials 0.000 claims description 2
- 150000004692 metal hydroxides Chemical class 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 17
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 12
- 239000000047 product Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 238000004821 distillation Methods 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000011575 calcium Substances 0.000 description 4
- 229910052791 calcium Inorganic materials 0.000 description 4
- 238000010924 continuous production Methods 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000000571 coke Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 235000011056 potassium acetate Nutrition 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000001632 sodium acetate Substances 0.000 description 3
- 235000017281 sodium acetate Nutrition 0.000 description 3
- 239000012808 vapor phase Substances 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- MWFMGBPGAXYFAR-UHFFFAOYSA-N 2-hydroxy-2-methylpropanenitrile Chemical compound CC(C)(O)C#N MWFMGBPGAXYFAR-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
- 239000004280 Sodium formate Substances 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 2
- 229910001863 barium hydroxide Inorganic materials 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 230000009969 flowable effect Effects 0.000 description 2
- 230000036571 hydration Effects 0.000 description 2
- 238000006703 hydration reaction Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 150000004679 hydroxides Chemical class 0.000 description 2
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 2
- 239000001095 magnesium carbonate Substances 0.000 description 2
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 2
- 235000014380 magnesium carbonate Nutrition 0.000 description 2
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 2
- 239000000347 magnesium hydroxide Substances 0.000 description 2
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 2
- 235000019254 sodium formate Nutrition 0.000 description 2
- 235000010265 sodium sulphite Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 229910052712 strontium Inorganic materials 0.000 description 2
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- STNJBCKSHOAVAJ-UHFFFAOYSA-N Methacrolein Chemical compound CC(=C)C=O STNJBCKSHOAVAJ-UHFFFAOYSA-N 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 229910052728 basic metal Inorganic materials 0.000 description 1
- 150000003818 basic metals Chemical class 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 229910021538 borax Inorganic materials 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 description 1
- UQGFMSUEHSUPRD-UHFFFAOYSA-N disodium;3,7-dioxido-2,4,6,8,9-pentaoxa-1,3,5,7-tetraborabicyclo[3.3.1]nonane Chemical compound [Na+].[Na+].O1B([O-])OB2OB([O-])OB1O2 UQGFMSUEHSUPRD-UHFFFAOYSA-N 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- BDAGIHXWWSANSR-NJFSPNSNSA-N hydroxyformaldehyde Chemical compound O[14CH]=O BDAGIHXWWSANSR-NJFSPNSNSA-N 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 229960003505 mequinol Drugs 0.000 description 1
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 1
- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 238000013021 overheating Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- ZNCPFRVNHGOPAG-UHFFFAOYSA-L sodium oxalate Chemical compound [Na+].[Na+].[O-]C(=O)C([O-])=O ZNCPFRVNHGOPAG-UHFFFAOYSA-L 0.000 description 1
- 229940039790 sodium oxalate Drugs 0.000 description 1
- 239000004328 sodium tetraborate Substances 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229910000018 strontium carbonate Inorganic materials 0.000 description 1
- 238000010792 warming Methods 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
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/377—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (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 |
|---|---|---|---|
| US63341367A | 1967-04-25 | 1967-04-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1768253A1 true DE1768253A1 (de) | 1971-10-28 |
Family
ID=24539538
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19681768253 Pending DE1768253A1 (de) | 1967-04-25 | 1968-04-19 | Verfahren zur Herstellung von Methacrylsaeure |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3562320A (forum.php) |
| BE (1) | BE713889A (forum.php) |
| DE (1) | DE1768253A1 (forum.php) |
| FR (1) | FR1577971A (forum.php) |
| GB (1) | GB1179987A (forum.php) |
| NL (1) | NL6805566A (forum.php) |
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0079432A1 (de) * | 1981-10-27 | 1983-05-25 | Hüls Aktiengesellschaft | Verfahren zur Herstellung von Methacrylsäure aus Isobutyraldehyd |
| DE102004006826A1 (de) * | 2004-02-11 | 2005-08-25 | Röhm GmbH & Co. KG | Verfahren zur Herstellung von alpha-Hydroxy-carbonsäuren und deren Ester |
| WO2008061819A1 (de) * | 2006-11-22 | 2008-05-29 | Evonik Röhm Gmbh | Verfahren zur herstellung von (meth)acrylsäure |
| DE102008044218A1 (de) | 2008-12-01 | 2010-06-02 | Evonik Röhm Gmbh | Verfahren zur Herstellung von einem Carbonsäureamid aus einer Carbonylverbindung und Blausäure |
| DE102011076642A1 (de) | 2011-05-27 | 2012-11-29 | Evonik Röhm Gmbh | Verfahren zur Herstellung von Methacrylsäure |
| USRE44517E1 (en) | 2003-09-19 | 2013-10-08 | Siemens Aktiengesellschaft | Large-capacity vehicle for transporting people, especially a rail vehicle, comprising carriages that are connected in an articulated manner |
| DE102013000602A1 (de) | 2013-01-16 | 2014-07-17 | Evonik Industries Ag | Verfahren zur Herstellung von Acrylsäure |
| DE102013209821A1 (de) | 2013-05-27 | 2014-11-27 | Evonik Industries Ag | Verfahren zur Dehydratisierung von alpha-substituierten Carbonsäuren |
| DE102014209650A1 (de) | 2014-05-21 | 2015-11-26 | Evonik Industries Ag | Verfahren zur Durchführung von Eliminierungsreaktionen an alpha-beta-substituierten Carbonsäuren unter homogener Katalyse und Katalysatorrezyklierung |
| DE102014213016A1 (de) | 2014-07-04 | 2016-01-07 | Evonik Röhm Gmbh | Dehydratisierung von alpha-substituierten Carbonsäuren in Gegenwart von Wasser bei hohen Drücken |
| DE102016210285A1 (de) | 2016-06-10 | 2017-12-14 | Evonik Röhm Gmbh | Verfahren zur Herstellung von Methacrylaten und Methacrylsäure |
| WO2023169810A1 (de) | 2022-03-11 | 2023-09-14 | Röhm Gmbh | Verfahren zur herstellung von alpha-hydroxyisobuttersäuremethylester und dessen anwendung in der elektronik-industrie |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH455748A (de) * | 1965-03-12 | 1968-05-15 | Lonza Ag | Verfahren zur Herstellung von Methacrylsäure aus a-Oxyisobuttersäure |
| JP4032033B2 (ja) * | 2003-06-30 | 2008-01-16 | ローム アンド ハース カンパニー | 高純度メタクリル酸の製造法 |
| US7687661B2 (en) * | 2006-03-15 | 2010-03-30 | Battelle Memorial Institute | Method for conversion of β-hydroxy carbonyl compounds |
| US20070219397A1 (en) * | 2006-03-15 | 2007-09-20 | Battelle Memorial Institute | Method for conversion of beta-hydroxy carbonyl compounds |
| DE102006025821A1 (de) * | 2006-06-02 | 2007-12-06 | Degussa Gmbh | Ein Enzym zur Herstellung von Mehylmalonatsemialdehyd oder Malonatsemialdehyd |
| AU2008257512A1 (en) * | 2007-06-01 | 2008-12-04 | Evonik Rohm Gmbh | A process for preparing methacrylic acid or methacrylic esters |
| CN110760335B (zh) * | 2018-07-27 | 2022-03-25 | 中国石油化工股份有限公司 | 一种混合c4高效生产汽油调合组分的方法 |
-
1967
- 1967-04-25 US US633413A patent/US3562320A/en not_active Expired - Lifetime
-
1968
- 1968-03-26 GB GB04583/68A patent/GB1179987A/en not_active Expired
- 1968-04-17 FR FR1577971D patent/FR1577971A/fr not_active Expired
- 1968-04-18 BE BE713889D patent/BE713889A/xx unknown
- 1968-04-19 NL NL6805566A patent/NL6805566A/xx unknown
- 1968-04-19 DE DE19681768253 patent/DE1768253A1/de active Pending
Cited By (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0079432A1 (de) * | 1981-10-27 | 1983-05-25 | Hüls Aktiengesellschaft | Verfahren zur Herstellung von Methacrylsäure aus Isobutyraldehyd |
| USRE44517E1 (en) | 2003-09-19 | 2013-10-08 | Siemens Aktiengesellschaft | Large-capacity vehicle for transporting people, especially a rail vehicle, comprising carriages that are connected in an articulated manner |
| DE102004006826A1 (de) * | 2004-02-11 | 2005-08-25 | Röhm GmbH & Co. KG | Verfahren zur Herstellung von alpha-Hydroxy-carbonsäuren und deren Ester |
| WO2005077878A1 (de) * | 2004-02-11 | 2005-08-25 | Röhm Gmbh | Verfahren zur herstellung von alpha-hydroxycarbonsäuren und deren ester |
| US7423173B2 (en) | 2004-02-11 | 2008-09-09 | Roehm Gmbh & Co. Kg | Method for producing alpha-hydroxycarboxylic acids and the esters thereof |
| CN101186568B (zh) * | 2006-11-22 | 2013-04-03 | 赢创罗姆有限公司 | 制备(甲基)丙烯酸的方法 |
| WO2008061819A1 (de) * | 2006-11-22 | 2008-05-29 | Evonik Röhm Gmbh | Verfahren zur herstellung von (meth)acrylsäure |
| US8207371B2 (en) | 2006-11-22 | 2012-06-26 | Evonik Röhm Gmbh | Process for preparing (meth)acrylic acid |
| DE102008044218A1 (de) | 2008-12-01 | 2010-06-02 | Evonik Röhm Gmbh | Verfahren zur Herstellung von einem Carbonsäureamid aus einer Carbonylverbindung und Blausäure |
| WO2012163600A1 (de) | 2011-05-27 | 2012-12-06 | Evonik Röhm Gmbh | Verfahren zur herstellung von methacrylsäure |
| DE102011076642A1 (de) | 2011-05-27 | 2012-11-29 | Evonik Röhm Gmbh | Verfahren zur Herstellung von Methacrylsäure |
| US9309180B2 (en) | 2013-01-16 | 2016-04-12 | Evonik Degussa Gmbh | Method for producing acrylic acid |
| WO2014111363A1 (de) | 2013-01-16 | 2014-07-24 | Evonik Industries Ag | Verfahren zur herstellung von acrylsäure |
| DE102013000602A1 (de) | 2013-01-16 | 2014-07-17 | Evonik Industries Ag | Verfahren zur Herstellung von Acrylsäure |
| DE102013209821A1 (de) | 2013-05-27 | 2014-11-27 | Evonik Industries Ag | Verfahren zur Dehydratisierung von alpha-substituierten Carbonsäuren |
| WO2014191145A1 (de) * | 2013-05-27 | 2014-12-04 | Evonik Industries Ag | Verfahren zur dehydratisierung von alpha-substituierten carbonsäuren |
| US9428437B2 (en) | 2013-05-27 | 2016-08-30 | Evonik Roehm Gmbh | Method for dehydrating alpha-substituted carboxylic acids |
| DE102014209650A1 (de) | 2014-05-21 | 2015-11-26 | Evonik Industries Ag | Verfahren zur Durchführung von Eliminierungsreaktionen an alpha-beta-substituierten Carbonsäuren unter homogener Katalyse und Katalysatorrezyklierung |
| DE102014213016A1 (de) | 2014-07-04 | 2016-01-07 | Evonik Röhm Gmbh | Dehydratisierung von alpha-substituierten Carbonsäuren in Gegenwart von Wasser bei hohen Drücken |
| WO2016001033A1 (de) | 2014-07-04 | 2016-01-07 | Evonik Röhm Gmbh | Dehydratisierung von alpha-substituierten carbonsäuren in gegenwart von wasser bei hohen drücken |
| DE102016210285A1 (de) | 2016-06-10 | 2017-12-14 | Evonik Röhm Gmbh | Verfahren zur Herstellung von Methacrylaten und Methacrylsäure |
| WO2023169810A1 (de) | 2022-03-11 | 2023-09-14 | Röhm Gmbh | Verfahren zur herstellung von alpha-hydroxyisobuttersäuremethylester und dessen anwendung in der elektronik-industrie |
Also Published As
| Publication number | Publication date |
|---|---|
| US3562320A (en) | 1971-02-09 |
| NL6805566A (forum.php) | 1968-10-28 |
| GB1179987A (en) | 1970-02-04 |
| FR1577971A (forum.php) | 1969-08-14 |
| BE713889A (forum.php) | 1968-10-18 |
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