KR100254539B1 - 메타크릴산메틸의 제조방법 - Google Patents
메타크릴산메틸의 제조방법 Download PDFInfo
- Publication number
- KR100254539B1 KR100254539B1 KR1019930023268A KR930023268A KR100254539B1 KR 100254539 B1 KR100254539 B1 KR 100254539B1 KR 1019930023268 A KR1019930023268 A KR 1019930023268A KR 930023268 A KR930023268 A KR 930023268A KR 100254539 B1 KR100254539 B1 KR 100254539B1
- Authority
- KR
- South Korea
- Prior art keywords
- reaction
- methyl methacrylate
- catalyst
- range
- hydroxyisobutyrate
- 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 - Lifetime
Links
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 title claims abstract description 33
- 238000000034 method Methods 0.000 title abstract description 19
- 238000006243 chemical reaction Methods 0.000 claims abstract description 60
- 239000003054 catalyst Substances 0.000 claims abstract description 56
- 239000010457 zeolite Substances 0.000 claims abstract description 40
- 229910021536 Zeolite Inorganic materials 0.000 claims abstract description 31
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims abstract description 31
- 238000004519 manufacturing process Methods 0.000 claims abstract description 18
- XYVQFUJDGOBPQI-UHFFFAOYSA-N Methyl-2-hydoxyisobutyric acid Chemical compound COC(=O)C(C)(C)O XYVQFUJDGOBPQI-UHFFFAOYSA-N 0.000 claims abstract description 10
- 230000007704 transition Effects 0.000 claims abstract description 9
- 239000002994 raw material Substances 0.000 claims description 14
- 239000004927 clay Substances 0.000 claims description 11
- BWLBGMIXKSTLSX-UHFFFAOYSA-N 2-hydroxyisobutyric acid Chemical compound CC(C)(O)C(O)=O BWLBGMIXKSTLSX-UHFFFAOYSA-N 0.000 claims description 10
- AZJYLVAUMGUUBL-UHFFFAOYSA-A u1qj22mc8e Chemical group [F-].[F-].[F-].[F-].[F-].[F-].[F-].[F-].[F-].[F-].[F-].[F-].[F-].[F-].[F-].[F-].[F-].[F-].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].O=[Si]=O.O=[Si]=O.O=[Si]=O.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3 AZJYLVAUMGUUBL-UHFFFAOYSA-A 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract description 33
- 238000004040 coloring Methods 0.000 abstract description 7
- 230000006866 deterioration Effects 0.000 abstract description 5
- 239000002131 composite material Substances 0.000 abstract 1
- 239000002253 acid Substances 0.000 description 13
- 239000011734 sodium Substances 0.000 description 13
- 238000009835 boiling Methods 0.000 description 12
- 239000006227 byproduct Substances 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 238000006297 dehydration reaction Methods 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 239000000126 substance Substances 0.000 description 8
- 230000003197 catalytic effect Effects 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 6
- 239000011230 binding agent Substances 0.000 description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 238000000465 moulding Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 230000007423 decrease Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 4
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- NGEWQZIDQIYUNV-UHFFFAOYSA-N L-valinic acid Natural products CC(C)C(O)C(O)=O NGEWQZIDQIYUNV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- -1 aluminum silicates Chemical class 0.000 description 3
- 230000018044 dehydration Effects 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 230000008929 regeneration Effects 0.000 description 3
- 238000011069 regeneration method Methods 0.000 description 3
- 238000001179 sorption measurement Methods 0.000 description 3
- DRYMMXUBDRJPDS-UHFFFAOYSA-N 2-hydroxy-2-methylpropanamide Chemical compound CC(C)(O)C(N)=O DRYMMXUBDRJPDS-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000002441 X-ray diffraction Methods 0.000 description 2
- YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical group 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 229940094522 laponite Drugs 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- XCOBTUNSZUJCDH-UHFFFAOYSA-B lithium magnesium sodium silicate Chemical compound [Li+].[Li+].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Na+].[Na+].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3 XCOBTUNSZUJCDH-UHFFFAOYSA-B 0.000 description 2
- 239000000395 magnesium oxide Substances 0.000 description 2
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000007493 shaping process Methods 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- MWFMGBPGAXYFAR-UHFFFAOYSA-N 2-hydroxy-2-methylpropanenitrile Chemical compound CC(C)(O)C#N MWFMGBPGAXYFAR-UHFFFAOYSA-N 0.000 description 1
- JIRULJUIQOAJPM-UHFFFAOYSA-N 3-methoxy-2-methylpropanoic acid Chemical compound COCC(C)C(O)=O JIRULJUIQOAJPM-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- 239000011398 Portland cement Substances 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- ANBBXQWFNXMHLD-UHFFFAOYSA-N aluminum;sodium;oxygen(2-) Chemical compound [O-2].[O-2].[Na+].[Al+3] ANBBXQWFNXMHLD-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 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 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 238000010304 firing Methods 0.000 description 1
- 238000010574 gas phase reaction Methods 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 229910000271 hectorite Inorganic materials 0.000 description 1
- KWLMIXQRALPRBC-UHFFFAOYSA-L hectorite Chemical compound [Li+].[OH-].[OH-].[Na+].[Mg+2].O1[Si]2([O-])O[Si]1([O-])O[Si]([O-])(O1)O[Si]1([O-])O2 KWLMIXQRALPRBC-UHFFFAOYSA-L 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 238000006140 methanolysis reaction Methods 0.000 description 1
- 239000012778 molding material Substances 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000013307 optical fiber Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229910052573 porcelain Inorganic materials 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 238000011027 product recovery Methods 0.000 description 1
- 239000012495 reaction gas Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229910000275 saponite Inorganic materials 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910001388 sodium aluminate Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
- C07C69/533—Monocarboxylic acid esters having only one carbon-to-carbon double bond
- C07C69/54—Acrylic acid esters; Methacrylic acid esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/317—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
- C07C67/327—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups by elimination of functional groups containing oxygen only in singly bound form
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP92-305542 | 1992-11-16 | ||
| JP30554292A JP3189858B2 (ja) | 1992-11-16 | 1992-11-16 | メタクリル酸メチルの製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR940011431A KR940011431A (ko) | 1994-06-21 |
| KR100254539B1 true KR100254539B1 (ko) | 2000-05-01 |
Family
ID=17946418
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019930023268A Expired - Lifetime KR100254539B1 (ko) | 1992-11-16 | 1993-11-04 | 메타크릴산메틸의 제조방법 |
Country Status (7)
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3520878B2 (ja) * | 1995-01-10 | 2004-04-19 | 三菱瓦斯化学株式会社 | メタクリル酸メチルの製造方法 |
| JPH11255710A (ja) * | 1998-03-11 | 1999-09-21 | Mitsubishi Gas Chem Co Inc | メタクリル酸メチルの製造方法 |
| EP1186592A1 (en) * | 2000-09-11 | 2002-03-13 | Mitsubishi Gas Chemical Company, Ltd. | Production of methacrylates |
| US6610625B1 (en) * | 2000-09-15 | 2003-08-26 | Tricat Industries, Inc. | Catalyst/adsorbent composition with improved performance |
| WO2003082795A2 (en) * | 2002-03-25 | 2003-10-09 | Cargill, Incorporated | METHODS OF MANUFACTURING DERIVATIVES OF β-HYDROXYCARBOXYLIC ACIDS |
| US20070219397A1 (en) * | 2006-03-15 | 2007-09-20 | Battelle Memorial Institute | Method for conversion of beta-hydroxy carbonyl compounds |
| US7687661B2 (en) * | 2006-03-15 | 2010-03-30 | Battelle Memorial Institute | Method for conversion of β-hydroxy carbonyl compounds |
| EP2625160B1 (en) | 2010-10-07 | 2014-08-13 | Rohm and Haas Company | Process for production of methacrylic acid ester |
| US9199910B2 (en) | 2012-06-04 | 2015-12-01 | Rohm And Haas Company | Process for production of methacrylic acid esters |
| US20160102043A1 (en) | 2013-06-26 | 2016-04-14 | Rohm And Haas Company | Process for production of methacrylic acid esters |
| US9938224B2 (en) | 2013-10-17 | 2018-04-10 | Cargill, Incorporated | Methods for producing alkyl hydroxyalkanoates |
| CN105848779B (zh) * | 2013-12-24 | 2018-08-28 | 三菱瓦斯化学株式会社 | 甲基丙烯酸甲酯制造用催化剂和甲基丙烯酸甲酯的制造方法 |
| RU2671574C2 (ru) * | 2014-04-10 | 2018-11-02 | Мицубиси Газ Кемикал Компани, Инк. | Формованный катализатор для применения в производстве метилметакрилата и способ производства метилметакрилата с применением указанного катализатора |
| WO2016061262A1 (en) | 2014-10-14 | 2016-04-21 | Gevo, Inc. | Methods for conversion of ethanol to functionalized lower hydrocarbons and downstream hydrocarbons |
| US10239819B2 (en) | 2014-10-17 | 2019-03-26 | Cargill, Incorporated | Methods for producing an ester of an alpha, beta-unsaturated carboxylic acid |
| US10633320B2 (en) | 2018-01-04 | 2020-04-28 | Gevo, Inc. | Upgrading fusel oil mixtures over heterogeneous catalysts to higher value renewable chemicals |
| JP6889322B1 (ja) | 2020-09-30 | 2021-06-18 | 住友化学株式会社 | 組成物 |
| EP4452919A1 (de) | 2021-12-23 | 2024-10-30 | Röhm GmbH | Verfahren zur herstellung von alkylmethacrylaten mit verbesserter ausbeute und verminderten emissionen flüchtiger organischer verbindungen |
| WO2023169810A1 (de) | 2022-03-11 | 2023-09-14 | Röhm Gmbh | Verfahren zur herstellung von alpha-hydroxyisobuttersäuremethylester und dessen anwendung in der elektronik-industrie |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2727618B2 (ja) * | 1989-01-26 | 1998-03-11 | 三菱瓦斯化学株式会社 | 不飽和カルボン酸エステルの製造方法 |
| JP2778131B2 (ja) * | 1989-07-14 | 1998-07-23 | 三菱瓦斯化学株式会社 | メタクリル酸メチルの製造方法 |
| JP2884639B2 (ja) * | 1989-11-28 | 1999-04-19 | 三菱瓦斯化学株式会社 | 不飽和カルボン酸エステルの製造法 |
| JP2906547B2 (ja) * | 1990-03-15 | 1999-06-21 | 三菱瓦斯化学株式会社 | α，β―不飽和カルボン酸エステルの製造方法 |
-
1992
- 1992-11-16 JP JP30554292A patent/JP3189858B2/ja not_active Expired - Lifetime
-
1993
- 1993-10-12 US US08/135,066 patent/US5371273A/en not_active Expired - Lifetime
- 1993-10-15 TW TW082108549A patent/TW277058B/zh not_active IP Right Cessation
- 1993-10-22 DE DE69309615T patent/DE69309615T2/de not_active Expired - Lifetime
- 1993-10-22 EP EP93117110A patent/EP0598243B1/en not_active Expired - Lifetime
- 1993-10-22 ES ES93117110T patent/ES2102575T3/es not_active Expired - Lifetime
- 1993-11-04 KR KR1019930023268A patent/KR100254539B1/ko not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DE69309615T2 (de) | 1997-07-17 |
| TW277058B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1996-06-01 |
| DE69309615D1 (de) | 1997-05-15 |
| EP0598243B1 (en) | 1997-04-09 |
| ES2102575T3 (es) | 1997-08-01 |
| EP0598243A2 (en) | 1994-05-25 |
| KR940011431A (ko) | 1994-06-21 |
| US5371273A (en) | 1994-12-06 |
| EP0598243A3 (en) | 1995-03-29 |
| JP3189858B2 (ja) | 2001-07-16 |
| JPH06157413A (ja) | 1994-06-03 |
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