AU2013269391B2 - Process for the production of methyl methacrylate - Google Patents
Process for the production of methyl methacrylate Download PDFInfo
- Publication number
- AU2013269391B2 AU2013269391B2 AU2013269391A AU2013269391A AU2013269391B2 AU 2013269391 B2 AU2013269391 B2 AU 2013269391B2 AU 2013269391 A AU2013269391 A AU 2013269391A AU 2013269391 A AU2013269391 A AU 2013269391A AU 2013269391 B2 AU2013269391 B2 AU 2013269391B2
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- AU
- Australia
- Prior art keywords
- monooxygenase
- baeyer
- methacrylate
- villiger
- genbank
- 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.)
- Ceased
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- 238000000034 method Methods 0.000 title claims abstract description 111
- 230000008569 process Effects 0.000 title claims abstract description 77
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 title claims abstract description 57
- 238000004519 manufacturing process Methods 0.000 title claims description 22
- 101710197852 Baeyer-Villiger monooxygenase Proteins 0.000 claims abstract description 132
- 101710137307 FAD-containing monooxygenase EthA Proteins 0.000 claims abstract description 132
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims abstract description 99
- 229940017219 methyl propionate Drugs 0.000 claims abstract description 99
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 claims abstract description 98
- 229920001577 copolymer Polymers 0.000 claims abstract description 11
- 229920000642 polymer Polymers 0.000 claims abstract description 8
- 102000004190 Enzymes Human genes 0.000 claims description 136
- 108090000790 Enzymes Proteins 0.000 claims description 136
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims description 132
- 238000006243 chemical reaction Methods 0.000 claims description 105
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 78
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 72
- 239000011541 reaction mixture Substances 0.000 claims description 71
- 239000000758 substrate Substances 0.000 claims description 68
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 57
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 30
- OSOIQJGOYGSIMF-UHFFFAOYSA-N cyclopentadecanone Chemical compound O=C1CCCCCCCCCCCCCC1 OSOIQJGOYGSIMF-UHFFFAOYSA-N 0.000 claims description 30
- 108030000430 Cyclohexanone monooxygenases Proteins 0.000 claims description 29
- 238000006220 Baeyer-Villiger oxidation reaction Methods 0.000 claims description 22
- 108010049118 4-hydroxyacetophenone monooxygenase Proteins 0.000 claims description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 18
- 108010074633 Mixed Function Oxygenases Proteins 0.000 claims description 16
- 102000008109 Mixed Function Oxygenases Human genes 0.000 claims description 16
- 239000006184 cosolvent Substances 0.000 claims description 16
- 239000003054 catalyst Substances 0.000 claims description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 11
- 241000589516 Pseudomonas Species 0.000 claims description 11
- 150000002148 esters Chemical class 0.000 claims description 11
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 10
- 241000588624 Acinetobacter calcoaceticus Species 0.000 claims description 9
- 241000187562 Rhodococcus sp. Species 0.000 claims description 9
- 241000589495 Xanthobacter flavus Species 0.000 claims description 9
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 8
- 239000000178 monomer Substances 0.000 claims description 8
- 108010058646 cyclohexanone oxygenase Proteins 0.000 claims description 7
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 claims description 6
- 229920003229 poly(methyl methacrylate) Polymers 0.000 claims description 6
- 239000004926 polymethyl methacrylate Substances 0.000 claims description 6
- 241000972318 Brachymonas petroleovorans Species 0.000 claims description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 4
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims description 3
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 claims description 3
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 3
- GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 claims description 3
- 239000012948 isocyanate Substances 0.000 claims description 3
- 150000002513 isocyanates Chemical class 0.000 claims description 3
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 claims description 2
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 claims description 2
- ZDQNWDNMNKSMHI-UHFFFAOYSA-N 1-[2-(2-prop-2-enoyloxypropoxy)propoxy]propan-2-yl prop-2-enoate Chemical compound C=CC(=O)OC(C)COC(C)COCC(C)OC(=O)C=C ZDQNWDNMNKSMHI-UHFFFAOYSA-N 0.000 claims description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 2
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 claims description 2
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 2
- WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical compound CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-UHFFFAOYSA-N 0.000 claims description 2
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims description 2
- RUMACXVDVNRZJZ-UHFFFAOYSA-N 2-methylpropyl 2-methylprop-2-enoate Chemical compound CC(C)COC(=O)C(C)=C RUMACXVDVNRZJZ-UHFFFAOYSA-N 0.000 claims description 2
- CFVWNXQPGQOHRJ-UHFFFAOYSA-N 2-methylpropyl prop-2-enoate Chemical compound CC(C)COC(=O)C=C CFVWNXQPGQOHRJ-UHFFFAOYSA-N 0.000 claims description 2
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 claims description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 2
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 2
- IAXXETNIOYFMLW-COPLHBTASA-N [(1s,3s,4s)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl] 2-methylprop-2-enoate Chemical compound C1C[C@]2(C)[C@@H](OC(=O)C(=C)C)C[C@H]1C2(C)C IAXXETNIOYFMLW-COPLHBTASA-N 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- 150000001735 carboxylic acids Chemical class 0.000 claims description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 claims description 2
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 claims description 2
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 claims description 2
- 229920001519 homopolymer Polymers 0.000 claims description 2
- 229940091853 isobornyl acrylate Drugs 0.000 claims description 2
- 229940119545 isobornyl methacrylate Drugs 0.000 claims description 2
- 125000005397 methacrylic acid ester group Chemical group 0.000 claims description 2
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 claims description 2
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 claims description 2
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 claims description 2
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 claims description 2
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 2
- 241000589774 Pseudomonas sp. Species 0.000 claims 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 228
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- 238000000855 fermentation Methods 0.000 description 91
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- GFAZHVHNLUBROE-UHFFFAOYSA-N hydroxymethyl propionaldehyde Natural products CCC(=O)CO GFAZHVHNLUBROE-UHFFFAOYSA-N 0.000 description 55
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- 239000000047 product Substances 0.000 description 43
- XJLXINKUBYWONI-DQQFMEOOSA-N [[(2r,3r,4r,5r)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2s,3r,4s,5s)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate Chemical compound NC(=O)C1=CC=C[N+]([C@@H]2[C@H]([C@@H](O)[C@H](COP([O-])(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](OP(O)(O)=O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 XJLXINKUBYWONI-DQQFMEOOSA-N 0.000 description 37
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Classifications
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/62—Carboxylic 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
- C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
- C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/12—Esters of monohydric alcohols or phenols
- C08F20/14—Methyl esters, e.g. methyl (meth)acrylate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
- C12N9/0004—Oxidoreductases (1.)
- C12N9/0071—Oxidoreductases (1.) acting on paired donors with incorporation of molecular oxygen (1.14)
- C12N9/0073—Oxidoreductases (1.) acting on paired donors with incorporation of molecular oxygen (1.14) with NADH or NADPH as one donor, and incorporation of one atom of oxygen 1.14.13
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Y—ENZYMES
- C12Y114/00—Oxidoreductases acting on paired donors, with incorporation or reduction of molecular oxygen (1.14)
- C12Y114/13—Oxidoreductases acting on paired donors, with incorporation or reduction of molecular oxygen (1.14) with NADH or NADPH as one donor, and incorporation of one atom of oxygen (1.14.13)
- C12Y114/13022—Cyclohexanone monooxygenase (1.14.13.22)
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Y—ENZYMES
- C12Y114/00—Oxidoreductases acting on paired donors, with incorporation or reduction of molecular oxygen (1.14)
- C12Y114/13—Oxidoreductases acting on paired donors, with incorporation or reduction of molecular oxygen (1.14) with NADH or NADPH as one donor, and incorporation of one atom of oxygen (1.14.13)
- C12Y114/13084—4-Hydroxyacetophenone monooxygenase (1.14.13.84)
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Y—ENZYMES
- C12Y114/00—Oxidoreductases acting on paired donors, with incorporation or reduction of molecular oxygen (1.14)
- C12Y114/13—Oxidoreductases acting on paired donors, with incorporation or reduction of molecular oxygen (1.14) with NADH or NADPH as one donor, and incorporation of one atom of oxygen (1.14.13)
- C12Y114/13092—Phenylacetone monooxygenase (1.14.13.92)
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Biotechnology (AREA)
- Microbiology (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Molecular Biology (AREA)
- Biomedical Technology (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB201209425A GB201209425D0 (en) | 2012-05-28 | 2012-05-28 | Process for production of methyl methacrylate |
| GB1209425.6 | 2012-05-28 | ||
| PCT/GB2013/051376 WO2013179005A1 (en) | 2012-05-28 | 2013-05-24 | Process for the production of methyl methacrylate |
Publications (2)
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| AU2013269391A1 AU2013269391A1 (en) | 2015-01-22 |
| AU2013269391B2 true AU2013269391B2 (en) | 2016-12-15 |
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| AU2013269391A Ceased AU2013269391B2 (en) | 2012-05-28 | 2013-05-24 | Process for the production of methyl methacrylate |
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| US (1) | US9816115B2 (https=) |
| EP (1) | EP2855689B1 (https=) |
| JP (2) | JP2015519062A (https=) |
| KR (1) | KR20150027141A (https=) |
| CN (1) | CN104350155B (https=) |
| AR (1) | AR091181A1 (https=) |
| AU (1) | AU2013269391B2 (https=) |
| BR (1) | BR112014029726A2 (https=) |
| CA (1) | CA2873620A1 (https=) |
| EA (1) | EA201492264A1 (https=) |
| ES (1) | ES2733758T3 (https=) |
| GB (1) | GB201209425D0 (https=) |
| IN (1) | IN2014DN10494A (https=) |
| MX (1) | MX2014014370A (https=) |
| MY (1) | MY169813A (https=) |
| SG (1) | SG11201407711QA (https=) |
| TW (1) | TW201400617A (https=) |
| WO (1) | WO2013179005A1 (https=) |
| ZA (1) | ZA201408554B (https=) |
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| CN105368737B (zh) * | 2015-09-21 | 2018-05-25 | 中海油天津化工研究设计院有限公司 | 一种处理高浓度有机废水的菌株、微生物菌剂及其应用 |
| WO2019048438A1 (en) | 2017-09-05 | 2019-03-14 | Vito Nv | IN SITU PRODUCT RECOVERY METHOD AND APPARATUS |
| CN108300707B (zh) * | 2018-02-07 | 2019-09-13 | 凯莱英医药集团（天津）股份有限公司 | 一种单加氧酶突变体及其制备方法和应用 |
| EP3957724A4 (en) * | 2019-04-17 | 2023-05-31 | Asymchem Life Science (Tianjin) Co., Ltd | TRANSAMINASE MUTANT AND USE THEREOF |
| CN110591984B (zh) * | 2019-10-30 | 2021-05-04 | 浙江大学 | 可降解甲苯、二甲苯与丙烯酸水混合废水的混合菌剂及其应用 |
| US11814738B2 (en) * | 2020-01-30 | 2023-11-14 | Avantium Knowledge Centre B.V. | Electrochemical production of formate |
| GB202010072D0 (en) * | 2020-07-01 | 2020-08-12 | Givaudan Sa | Enzyme-mediated process |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
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| GB1428277A (en) | 1972-08-03 | 1976-03-17 | Monsanto Co | Production of unsaturated acids and esters |
| DE3004467A1 (de) | 1980-02-07 | 1981-08-13 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von methylmethacrylat durch umsetzung von methylpropionat und methanol |
| JP2901008B2 (ja) | 1989-11-28 | 1999-06-02 | 明治乳業株式会社 | 乳酸菌によるジアセチル、アセトイン発酵法 |
| AU689626B2 (en) | 1994-07-25 | 1998-04-02 | Boehringer Mannheim Gmbh | Peptides marked with metal chelates |
| US5753474A (en) | 1995-12-26 | 1998-05-19 | Environmental Energy, Inc. | Continuous two stage, dual path anaerobic fermentation of butanol and other organic solvents using two different strains of bacteria |
| WO2000009682A1 (en) | 1998-08-12 | 2000-02-24 | Maxygen, Inc. | Dna shuffling of monooxygenase genes for production of industrial chemicals |
| US7105296B2 (en) | 2001-08-29 | 2006-09-12 | E. I. Du Pont De Nemours And Company | Genes encoding Baeyer-Villiger monooxygenases |
| WO2004007750A2 (en) | 2002-07-11 | 2004-01-22 | Diversa Corporation | Monooxygenases, nucleic acids encoding them and methods for making and using them |
| US8206970B2 (en) | 2006-05-02 | 2012-06-26 | Butamax(Tm) Advanced Biofuels Llc | Production of 2-butanol and 2-butanone employing aminobutanol phosphate phospholyase |
| US7541173B2 (en) | 2006-06-15 | 2009-06-02 | E.I. Du Pont De Nemours And Company | Solvent tolerant microorganisms and methods of isolation |
| DE102006039189B4 (de) * | 2006-08-21 | 2010-07-29 | Ernst-Moritz-Arndt-Universität Greifswald | Enantioselektive Darstellung von aliphatischen azyklischen Estern und Ketonen |
| DE102007050762B3 (de) | 2007-10-22 | 2009-05-07 | Heraeus Medical Gmbh | Pastenförmiger Polymethylmethacrylat-Knochenzement und seine Verwendung |
| US8119844B2 (en) | 2008-05-01 | 2012-02-21 | Lanzatech New Zealand Limited | Alcohol production process |
| FR2940801B1 (fr) | 2009-01-06 | 2012-08-17 | Arkema France | Procede de fabrication d'un methacrylate de methyle derive de la biomasse |
| GB0922255D0 (en) | 2009-12-21 | 2010-02-03 | Lucite Int Uk Ltd | Method of producing acrylic and methacrylic acid |
| KR101144235B1 (ko) | 2010-02-25 | 2012-05-10 | 한국과학기술연구원 | 바이오에탄올 폐발효액을 이용한 부탄올의 제조방법 |
| US20120045807A1 (en) | 2010-08-19 | 2012-02-23 | Lanzatech New Zealand Limited | Process for producing chemicals using microbial fermentation of substrates comprising carbon monoxide |
| JP2014518613A (ja) | 2011-04-01 | 2014-08-07 | ジェノマティカ・インコーポレイテッド | メタクリル酸およびメタクリレートエステルの産生のための微生物ならびにそれに関連する方法 |
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2012
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2013
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2014
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2017
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Non-Patent Citations (1)
| Title |
|---|
| Kirschner, A. et al, Angewandte Chemie International Edition, 2006, Vol. 45, No. 42, pages 7004-7006. * |
Also Published As
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| JP6571749B2 (ja) | 2019-09-04 |
| KR20150027141A (ko) | 2015-03-11 |
| SG11201407711QA (en) | 2014-12-30 |
| EP2855689B1 (en) | 2019-04-03 |
| IN2014DN10494A (https=) | 2015-08-21 |
| WO2013179005A1 (en) | 2013-12-05 |
| MX2014014370A (es) | 2015-02-05 |
| CA2873620A1 (en) | 2013-12-05 |
| AR091181A1 (es) | 2015-01-14 |
| EA201492264A1 (ru) | 2015-05-29 |
| AU2013269391A1 (en) | 2015-01-22 |
| JP2015519062A (ja) | 2015-07-09 |
| CN104350155A (zh) | 2015-02-11 |
| BR112014029726A2 (pt) | 2017-06-27 |
| GB201209425D0 (en) | 2012-07-11 |
| EP2855689A1 (en) | 2015-04-08 |
| JP2018050637A (ja) | 2018-04-05 |
| US9816115B2 (en) | 2017-11-14 |
| ZA201408554B (en) | 2016-04-28 |
| ES2733758T3 (es) | 2019-12-02 |
| MY169813A (en) | 2019-05-16 |
| CN104350155B (zh) | 2017-10-31 |
| US20150112037A1 (en) | 2015-04-23 |
| TW201400617A (zh) | 2014-01-01 |
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