AU2007327787B2 - Process and apparatus for preparing alkyl esters of methacrylic acid - Google Patents
Process and apparatus for preparing alkyl esters of methacrylic acid Download PDFInfo
- Publication number
- AU2007327787B2 AU2007327787B2 AU2007327787A AU2007327787A AU2007327787B2 AU 2007327787 B2 AU2007327787 B2 AU 2007327787B2 AU 2007327787 A AU2007327787 A AU 2007327787A AU 2007327787 A AU2007327787 A AU 2007327787A AU 2007327787 B2 AU2007327787 B2 AU 2007327787B2
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- Australia
- Prior art keywords
- reaction
- water
- heat exchanger
- process according
- reaction product
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 101
- 230000008569 process Effects 0.000 title claims abstract description 91
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 title abstract description 40
- 125000005907 alkyl ester group Chemical group 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 claims abstract description 14
- 238000006243 chemical reaction Methods 0.000 claims description 122
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 105
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 70
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 62
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 57
- 239000001117 sulphuric acid Substances 0.000 claims description 57
- 235000011149 sulphuric acid Nutrition 0.000 claims description 57
- MWFMGBPGAXYFAR-UHFFFAOYSA-N 2-hydroxy-2-methylpropanenitrile Chemical compound CC(C)(O)C#N MWFMGBPGAXYFAR-UHFFFAOYSA-N 0.000 claims description 50
- 239000007795 chemical reaction product Substances 0.000 claims description 49
- 238000005886 esterification reaction Methods 0.000 claims description 49
- 239000000203 mixture Substances 0.000 claims description 47
- 238000004821 distillation Methods 0.000 claims description 40
- 238000000746 purification Methods 0.000 claims description 35
- 239000011541 reaction mixture Substances 0.000 claims description 34
- -1 alkyl methacrylates Chemical class 0.000 claims description 32
- 239000002253 acid Substances 0.000 claims description 28
- 239000008346 aqueous phase Substances 0.000 claims description 26
- 238000009835 boiling Methods 0.000 claims description 25
- 239000000126 substance Substances 0.000 claims description 24
- 238000005406 washing Methods 0.000 claims description 22
- 239000012535 impurity Substances 0.000 claims description 20
- 238000005188 flotation Methods 0.000 claims description 19
- 239000012071 phase Substances 0.000 claims description 19
- 239000012074 organic phase Substances 0.000 claims description 16
- 238000006116 polymerization reaction Methods 0.000 claims description 16
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims description 15
- 238000000465 moulding Methods 0.000 claims description 14
- 239000007787 solid Substances 0.000 claims description 14
- 238000009833 condensation Methods 0.000 claims description 12
- 230000005494 condensation Effects 0.000 claims description 12
- 238000005191 phase separation Methods 0.000 claims description 10
- 238000004064 recycling Methods 0.000 claims description 8
- 239000000654 additive Substances 0.000 claims description 6
- 238000000576 coating method Methods 0.000 claims description 6
- 238000005553 drilling Methods 0.000 claims description 6
- 230000000694 effects Effects 0.000 claims description 6
- 239000008394 flocculating agent Substances 0.000 claims description 6
- 239000010985 leather Substances 0.000 claims description 6
- 229920000642 polymer Polymers 0.000 claims description 5
- 150000003863 ammonium salts Chemical class 0.000 claims description 2
- 230000000379 polymerizing effect Effects 0.000 claims description 2
- 238000010526 radical polymerization reaction Methods 0.000 claims 1
- 239000000047 product Substances 0.000 abstract description 45
- 238000012545 processing Methods 0.000 abstract description 13
- 239000012084 conversion product Substances 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- JHPBZFOKBAGZBL-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylprop-2-enoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)=C JHPBZFOKBAGZBL-UHFFFAOYSA-N 0.000 description 46
- 150000002148 esters Chemical class 0.000 description 43
- 239000007789 gas Substances 0.000 description 41
- 238000001816 cooling Methods 0.000 description 31
- 230000032050 esterification Effects 0.000 description 30
- 239000003381 stabilizer Substances 0.000 description 27
- 239000003054 catalyst Substances 0.000 description 19
- 238000002156 mixing Methods 0.000 description 18
- 238000002360 preparation method Methods 0.000 description 18
- 239000000470 constituent Substances 0.000 description 17
- 239000007788 liquid Substances 0.000 description 16
- 238000005201 scrubbing Methods 0.000 description 16
- 238000010626 work up procedure Methods 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 125000005395 methacrylic acid group Chemical group 0.000 description 14
- 238000007112 amidation reaction Methods 0.000 description 13
- 150000001875 compounds Chemical class 0.000 description 13
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 12
- 230000009435 amidation Effects 0.000 description 11
- 150000001408 amides Chemical class 0.000 description 11
- 238000003860 storage Methods 0.000 description 11
- 230000008901 benefit Effects 0.000 description 10
- 239000012267 brine Substances 0.000 description 9
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 230000007062 hydrolysis Effects 0.000 description 8
- 238000006460 hydrolysis reaction Methods 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 150000002894 organic compounds Chemical class 0.000 description 8
- 239000002808 molecular sieve Substances 0.000 description 7
- 238000012856 packing Methods 0.000 description 7
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 7
- 230000003068 static effect Effects 0.000 description 7
- 238000012546 transfer Methods 0.000 description 7
- 238000011144 upstream manufacturing Methods 0.000 description 7
- 229910021529 ammonia Inorganic materials 0.000 description 6
- 238000013461 design Methods 0.000 description 6
- 239000010408 film Substances 0.000 description 6
- 239000000376 reactant Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000006189 Andrussov oxidation reaction Methods 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000010924 continuous production Methods 0.000 description 5
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 230000006641 stabilisation Effects 0.000 description 4
- 238000011105 stabilization Methods 0.000 description 4
- 239000002699 waste material Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000009471 action Effects 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000006260 foam Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- 230000000274 adsorptive effect Effects 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 238000004939 coking Methods 0.000 description 2
- 239000002826 coolant Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000011143 downstream manufacturing Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000011552 falling film Substances 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
- 238000006053 organic reaction Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- 230000005526 G1 to G0 transition Effects 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910000990 Ni alloy Inorganic materials 0.000 description 1
- 239000002033 PVDF binder Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 229910010293 ceramic material Inorganic materials 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000005670 electromagnetic radiation Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229920001903 high density polyethylene Polymers 0.000 description 1
- 239000004700 high-density polyethylene Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 238000013021 overheating Methods 0.000 description 1
- 238000001139 pH measurement Methods 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- 238000013022 venting Methods 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/18—Preparation of carboxylic acid esters by conversion of a group containing nitrogen into an ester group
- C07C67/20—Preparation of carboxylic acid esters by conversion of a group containing nitrogen into an ester group from amides or lactams
-
- 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
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/18—Manufacture of films or sheets
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
- D21H17/20—Macromolecular organic compounds
- D21H17/33—Synthetic macromolecular compounds
- D21H17/34—Synthetic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- D21H17/37—Polymers of unsaturated acids or derivatives thereof, e.g. polyacrylates
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H19/00—Coated paper; Coating material
- D21H19/10—Coatings without pigments
- D21H19/14—Coatings without pigments applied in a form other than the aqueous solution defined in group D21H19/12
- D21H19/20—Coatings without pigments applied in a form other than the aqueous solution defined in group D21H19/12 comprising macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Manufacturing & Machinery (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102006058251A DE102006058251A1 (de) | 2006-12-08 | 2006-12-08 | Verfahren und Vorrichtung zur Herstellung von Methacrylsäurealkylestern |
| DE102006058251.9 | 2006-12-08 | ||
| PCT/EP2007/059107 WO2008068063A1 (de) | 2006-12-08 | 2007-08-31 | Verfahren und vorrichtung zur herstellung von methacrylsäurealkylestern |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2007327787A1 AU2007327787A1 (en) | 2008-06-12 |
| AU2007327787B2 true AU2007327787B2 (en) | 2012-08-23 |
Family
ID=38786597
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2007327787A Ceased AU2007327787B2 (en) | 2006-12-08 | 2007-08-31 | Process and apparatus for preparing alkyl esters of methacrylic acid |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US9637574B2 (https=) |
| EP (1) | EP2054369B9 (https=) |
| JP (1) | JP5757684B2 (https=) |
| KR (1) | KR101497719B1 (https=) |
| CN (1) | CN101195576B (https=) |
| AU (1) | AU2007327787B2 (https=) |
| BR (1) | BRPI0720245B1 (https=) |
| DE (1) | DE102006058251A1 (https=) |
| ES (1) | ES2531086T3 (https=) |
| MX (1) | MX2009005896A (https=) |
| MY (1) | MY157939A (https=) |
| RU (1) | RU2486173C2 (https=) |
| TW (1) | TWI371443B (https=) |
| WO (1) | WO2008068063A1 (https=) |
| ZA (1) | ZA200903945B (https=) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102008000785A1 (de) * | 2008-03-20 | 2009-09-24 | Evonik Röhm Gmbh | Verfahren zur Herstellung von Methacrylsäure |
| DE102008000787A1 (de) | 2008-03-20 | 2009-09-24 | Evonik Röhm Gmbh | Verfahren zur Aufreinigung von Methacrylsäure |
| JP5432852B2 (ja) * | 2009-09-30 | 2014-03-05 | ローム アンド ハース カンパニー | メタクリル酸メチルの精製によって生じる流れから価値のある化合物を回収する方法 |
| KR101144306B1 (ko) * | 2010-08-26 | 2012-05-11 | 주식회사 엘지화학 | 알킬(메트)아크릴레이트의 제조 방법 |
| DE102011076642A1 (de) | 2011-05-27 | 2012-11-29 | Evonik Röhm Gmbh | Verfahren zur Herstellung von Methacrylsäure |
| CN103145576B (zh) * | 2013-03-28 | 2015-06-17 | 重庆紫光化工股份有限公司 | 一种环境友好的甲基丙烯酰胺的制备和提纯方法 |
| BR112020001740A2 (pt) * | 2017-07-28 | 2020-07-21 | Rohm And Haas Company | método para preparar metil metacrilato de metacroleína e metanol. |
| CN107862974B (zh) * | 2017-11-22 | 2023-11-24 | 河南莱帕克化工设备制造有限公司 | 苯甲酰胺生产线教学装置 |
| CN113467550B (zh) * | 2020-03-30 | 2022-10-04 | 中石油吉林化工工程有限公司 | 用于mma生产装置中酰化反应的温控系统及温控方法 |
| KR102860381B1 (ko) * | 2020-07-10 | 2025-09-15 | 주식회사 엘지화학 | 페놀계 부산물 분해방법 |
| CN115925738A (zh) * | 2022-12-13 | 2023-04-07 | 南通紫琅生物医药科技有限公司 | 一种磷脂酰丝氨酸浓缩生产制备方法 |
| CN119662299B (zh) * | 2025-01-14 | 2025-12-09 | 中国神华煤制油化工有限公司 | 一种煤直接液化装置停工退碱液的方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3006950A (en) * | 1959-07-31 | 1961-10-31 | Electro Chimie D Electrometall | Process of making methyl methacrylate |
Family Cites Families (41)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2101821A (en) * | 1934-11-07 | 1937-12-07 | Ici Ltd | Manufacture of unsaturated or ganic compounds |
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2006
- 2006-12-08 DE DE102006058251A patent/DE102006058251A1/de not_active Withdrawn
-
2007
- 2007-02-28 CN CN2007100843892A patent/CN101195576B/zh not_active Expired - Fee Related
- 2007-08-31 BR BRPI0720245A patent/BRPI0720245B1/pt not_active IP Right Cessation
- 2007-08-31 KR KR1020097011718A patent/KR101497719B1/ko not_active Expired - Fee Related
- 2007-08-31 MX MX2009005896A patent/MX2009005896A/es active IP Right Grant
- 2007-08-31 US US12/515,964 patent/US9637574B2/en not_active Expired - Fee Related
- 2007-08-31 JP JP2009539671A patent/JP5757684B2/ja not_active Expired - Fee Related
- 2007-08-31 RU RU2009125685/04A patent/RU2486173C2/ru not_active IP Right Cessation
- 2007-08-31 WO PCT/EP2007/059107 patent/WO2008068063A1/de not_active Ceased
- 2007-08-31 EP EP07803107.7A patent/EP2054369B9/de not_active Not-in-force
- 2007-08-31 AU AU2007327787A patent/AU2007327787B2/en not_active Ceased
- 2007-08-31 MY MYPI20091806A patent/MY157939A/en unknown
- 2007-08-31 ES ES07803107T patent/ES2531086T3/es active Active
- 2007-12-04 TW TW096146122A patent/TWI371443B/zh not_active IP Right Cessation
-
2009
- 2009-06-05 ZA ZA200903945A patent/ZA200903945B/xx unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US3006950A (en) * | 1959-07-31 | 1961-10-31 | Electro Chimie D Electrometall | Process of making methyl methacrylate |
Also Published As
| Publication number | Publication date |
|---|---|
| HK1119666A1 (en) | 2009-03-13 |
| WO2008068063A1 (de) | 2008-06-12 |
| EP2054369B9 (de) | 2018-05-23 |
| KR101497719B1 (ko) | 2015-03-02 |
| EP2054369B2 (de) | 2018-01-24 |
| TW200846316A (en) | 2008-12-01 |
| DE102006058251A1 (de) | 2008-06-12 |
| EP2054369A1 (de) | 2009-05-06 |
| ES2531086T3 (es) | 2015-03-10 |
| JP2010511650A (ja) | 2010-04-15 |
| RU2009125685A (ru) | 2011-01-20 |
| ZA200903945B (en) | 2010-05-26 |
| BRPI0720245A2 (pt) | 2013-12-31 |
| MY157939A (en) | 2016-08-15 |
| TWI371443B (en) | 2012-09-01 |
| MX2009005896A (es) | 2009-06-16 |
| CN101195576A (zh) | 2008-06-11 |
| US9637574B2 (en) | 2017-05-02 |
| BRPI0720245B1 (pt) | 2017-03-21 |
| RU2486173C2 (ru) | 2013-06-27 |
| JP5757684B2 (ja) | 2015-07-29 |
| AU2007327787A1 (en) | 2008-06-12 |
| KR20090096451A (ko) | 2009-09-10 |
| US20100056742A1 (en) | 2010-03-04 |
| CN101195576B (zh) | 2012-04-18 |
| EP2054369B1 (de) | 2014-12-17 |
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| FGA | Letters patent sealed or granted (standard patent) | ||
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |