KR20150005938A - 고순도, 비황변성 (메트)아크릴산의 제조 방법 - Google Patents
고순도, 비황변성 (메트)아크릴산의 제조 방법 Download PDFInfo
- Publication number
- KR20150005938A KR20150005938A KR20147030411A KR20147030411A KR20150005938A KR 20150005938 A KR20150005938 A KR 20150005938A KR 20147030411 A KR20147030411 A KR 20147030411A KR 20147030411 A KR20147030411 A KR 20147030411A KR 20150005938 A KR20150005938 A KR 20150005938A
- Authority
- KR
- South Korea
- Prior art keywords
- meth
- acrylic acid
- process according
- pure
- aqueous
- 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
Links
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 title claims abstract description 119
- 238000000034 method Methods 0.000 title claims abstract description 69
- 238000002360 preparation method Methods 0.000 title abstract description 3
- 238000004383 yellowing Methods 0.000 title description 2
- 230000003647 oxidation Effects 0.000 claims abstract description 22
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 22
- 239000003456 ion exchange resin Substances 0.000 claims abstract description 13
- 229920003303 ion-exchange polymer Polymers 0.000 claims abstract description 13
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims abstract description 11
- 238000000926 separation method Methods 0.000 claims description 13
- 239000003960 organic solvent Substances 0.000 claims description 7
- 238000005342 ion exchange Methods 0.000 claims description 6
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 5
- 241001550224 Apha Species 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 15
- 150000001412 amines Chemical class 0.000 abstract description 4
- 230000007774 longterm Effects 0.000 abstract description 4
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 20
- 239000007789 gas Substances 0.000 description 19
- 239000012071 phase Substances 0.000 description 15
- 238000002425 crystallisation Methods 0.000 description 14
- 230000008025 crystallization Effects 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 238000004821 distillation Methods 0.000 description 11
- 239000012535 impurity Substances 0.000 description 11
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 10
- 238000009835 boiling Methods 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 150000001299 aldehydes Chemical class 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 238000010791 quenching Methods 0.000 description 6
- 230000000171 quenching effect Effects 0.000 description 6
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 239000001569 carbon dioxide Substances 0.000 description 4
- 229910002092 carbon dioxide Inorganic materials 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000002845 discoloration Methods 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 239000007792 gaseous phase Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- STNJBCKSHOAVAJ-UHFFFAOYSA-N Methacrolein Chemical compound CC(=C)C=O STNJBCKSHOAVAJ-UHFFFAOYSA-N 0.000 description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical group SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- CLBRCZAHAHECKY-UHFFFAOYSA-N [Co].[Pt] Chemical compound [Co].[Pt] CLBRCZAHAHECKY-UHFFFAOYSA-N 0.000 description 2
- 239000000061 acid fraction Substances 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000010574 gas phase reaction Methods 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- 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 1
- LLQHSBBZNDXTIV-UHFFFAOYSA-N 6-[5-[[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]methyl]-4,5-dihydro-1,2-oxazol-3-yl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC1CC(=NO1)C1=CC2=C(NC(O2)=O)C=C1 LLQHSBBZNDXTIV-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- -1 aliphatic amines Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 1
- 229940018557 citraconic acid Drugs 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000003712 decolorant Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000036425 denaturation Effects 0.000 description 1
- 238000004925 denaturation Methods 0.000 description 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 230000005180 public health Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000005496 tempering Methods 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/47—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
- C07C51/44—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation by distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/48—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/CN2012/075033 WO2013163806A1 (en) | 2012-05-03 | 2012-05-03 | Process for preparation of highly pure, non-yellowing methacrylic acid |
| CNPCT/CN2012/075033 | 2012-05-03 | ||
| PCT/EP2013/058289 WO2013164216A1 (en) | 2012-05-03 | 2013-04-22 | Process for preparation of highly pure, non-yellowing (meth)acrylic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20150005938A true KR20150005938A (ko) | 2015-01-15 |
Family
ID=48142804
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR20147030411A Ceased KR20150005938A (ko) | 2012-05-03 | 2013-04-22 | 고순도, 비황변성 (메트)아크릴산의 제조 방법 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US9290431B2 (enExample) |
| EP (1) | EP2844633A1 (enExample) |
| JP (1) | JP2015515963A (enExample) |
| KR (1) | KR20150005938A (enExample) |
| SG (1) | SG11201407133UA (enExample) |
| TW (1) | TW201406717A (enExample) |
| WO (2) | WO2013163806A1 (enExample) |
| ZA (1) | ZA201407984B (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR3008899B1 (fr) * | 2013-07-25 | 2017-04-21 | Arkema France | Methode et systeme pour la distribution d'un liquide dans des capacites pour la preparation de monomeres (meth)acryliques |
| EP3907210A1 (en) * | 2020-05-08 | 2021-11-10 | Sulzer Management AG | A process and apparatus for preparing a purified styrene composition from styrene containing feedstock |
Family Cites Families (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1668362B2 (de) | 1968-02-17 | 1976-11-11 | Hoechst Ag, 6000 Frankfurt | Verfahren zur herstellung aliphatischer acrylsaeureester |
| BE786398A (fr) | 1971-07-21 | 1973-01-18 | Basf Ag | Procede de preparation de l'acide acrylique anhydre |
| JPS55124734A (en) | 1979-03-22 | 1980-09-26 | Nippon Kayaku Co Ltd | Preparation of methacrylic acid |
| JPS55129239A (en) * | 1979-03-28 | 1980-10-06 | Mitsubishi Rayon Co Ltd | Purification of methacrylic acid |
| JPS56108735A (en) | 1980-02-01 | 1981-08-28 | Sumitomo Chem Co Ltd | Treating method of waste water in preparation of methacrylic acid |
| JPS5948437A (ja) * | 1982-09-14 | 1984-03-19 | Mitsubishi Rayon Co Ltd | メタクリル酸の精製法 |
| DE3467340D1 (en) | 1984-07-21 | 1987-12-17 | Mitsubishi Petrochemical Co | Process for purification of 1,2-unsaturated carboxylic acids and/or esters thereof |
| US4879412A (en) | 1985-03-14 | 1989-11-07 | Mitsui Toatsu Chemicals, Inc. | Purification process of methacrylic acid |
| JPS63122642A (ja) | 1986-11-11 | 1988-05-26 | Mitsubishi Rayon Co Ltd | メタクロレイン及びメタクリル酸の製造法 |
| CA1308737C (en) | 1987-04-16 | 1992-10-13 | Syoichi Matsumoto | Process for producing methacrylic ester |
| CA1316545C (en) | 1987-06-27 | 1993-04-20 | Morimasa Kuragano | Quenching process of reaction product gas containing methacrylic acid and treatment method of quenched liquid |
| JPS646233A (en) | 1987-06-27 | 1989-01-10 | Mitsui Toatsu Chemicals | Purification of methacrylic acid |
| DE3721865A1 (de) | 1987-07-02 | 1989-01-12 | Basf Ag | Verfahren zur herstellung von methacrylsaeure |
| JPH01193240A (ja) | 1988-01-29 | 1989-08-03 | Mitsui Toatsu Chem Inc | メタクリル酸メチルの製造法 |
| JPH0764776B2 (ja) | 1988-03-23 | 1995-07-12 | 三井東圧化学株式会社 | メタクロレインの吸収方法 |
| JPH0684326B2 (ja) | 1988-06-03 | 1994-10-26 | 株式会社日本触媒 | メタクロレインの回収方法 |
| DE3844087A1 (de) | 1988-12-28 | 1990-07-05 | Basf Ag | Verfahren zur herstellung von methacrylsaeure durch oxidation von methacrolein |
| EP0608917B1 (en) | 1989-12-06 | 1999-04-21 | Nippon Shokubai Co., Ltd. | Process for producing methacrolein and methacrylic acid |
| US5198579A (en) | 1990-11-14 | 1993-03-30 | Mitsui Toatsu Chemicals, Inc. | Catalyst for oxidizing methacrolein and method for preparing methacrylic acid |
| DE4132684A1 (de) | 1991-10-01 | 1993-04-08 | Basf Ag | Verfahren zur katalytischen gasphasenoxidation von methacrolein zu methacrylsaeure |
| TW305830B (enExample) | 1993-03-26 | 1997-05-21 | Sulzer Chemtech Ag | |
| DE4405059A1 (de) | 1994-02-17 | 1995-08-24 | Basf Ag | Multimetalloxidmassen |
| JPH08134011A (ja) | 1994-11-04 | 1996-05-28 | Mitsui Toatsu Chem Inc | メタクリル酸の精製方法 |
| DE19627847A1 (de) | 1996-07-10 | 1998-01-15 | Basf Ag | Verfahren zur Herstellung von Acrylsäure |
| JP3222068B2 (ja) * | 1996-09-13 | 2001-10-22 | 三菱レイヨン株式会社 | メタクリル酸の精製法 |
| JP3871406B2 (ja) * | 1997-08-11 | 2007-01-24 | 三菱レイヨン株式会社 | メタクリル酸の精製方法 |
| DE19740252A1 (de) | 1997-09-12 | 1999-03-18 | Basf Ag | Verfahren zur Herstellung von Acrylsäure und Methacrylsäure |
| DE19838817A1 (de) | 1998-08-26 | 2000-03-02 | Basf Ag | Verfahren zur kontinuierlichen Gewinnung von (Meth)acrylsäure |
| JP3702710B2 (ja) | 1999-06-15 | 2005-10-05 | 住友化学株式会社 | メタクリル酸製造用触媒およびメタクリル酸の製造方法 |
| JP2001213839A (ja) | 2000-02-03 | 2001-08-07 | Nippon Shokubai Co Ltd | （メタ）アクリル酸の製造方法 |
| JP4960562B2 (ja) | 2000-04-11 | 2012-06-27 | ビーエーエスエフ ソシエタス・ヨーロピア | 粗製アクリル酸溶融物の精製法 |
| US7803969B2 (en) | 2001-01-12 | 2010-09-28 | Evonik Stockhausen Gmbh | Continuous process for the production and purification of acrylic acid |
| DE10131479B4 (de) | 2001-06-29 | 2005-05-19 | Röhm GmbH & Co. KG | Farbstabilisierung von grundstabilisierten ethylenisch ungesättigten Monomeren, insbesondere von grundstabilisierten Hydroxyalkyl(meth)acrylaten |
| DE10138150A1 (de) | 2001-08-03 | 2003-02-13 | Basf Ag | Verfahren zur Herstellung wasserabsorbierender Harze |
| JP3918528B2 (ja) * | 2001-11-27 | 2007-05-23 | 三菱化学株式会社 | （メタ）アクリル酸の精製方法 |
| JP2005179352A (ja) * | 2003-11-28 | 2005-07-07 | Mitsubishi Chemicals Corp | （メタ）アクリル酸の精製方法 |
| JP2008161848A (ja) * | 2007-01-04 | 2008-07-17 | Mitsubishi Rayon Co Ltd | 縦型多段翼反応槽及び（メタ）アクリル酸の精製方法 |
| EP2085376B1 (en) * | 2008-01-30 | 2012-09-05 | Evonik Röhm GmbH | Process for preparation of high purity methacrylic acid |
| DE102008043609A1 (de) * | 2008-11-10 | 2010-05-12 | Evonik Röhm Gmbh | Verfahren zur Reduzierung des Wassergehalts in (Meth)acrylsäure |
-
2012
- 2012-05-03 WO PCT/CN2012/075033 patent/WO2013163806A1/en not_active Ceased
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2013
- 2013-04-22 EP EP13717525.3A patent/EP2844633A1/en not_active Withdrawn
- 2013-04-22 SG SG11201407133UA patent/SG11201407133UA/en unknown
- 2013-04-22 WO PCT/EP2013/058289 patent/WO2013164216A1/en not_active Ceased
- 2013-04-22 JP JP2015509367A patent/JP2015515963A/ja active Pending
- 2013-04-22 US US14/397,295 patent/US9290431B2/en not_active Expired - Fee Related
- 2013-04-22 KR KR20147030411A patent/KR20150005938A/ko not_active Ceased
- 2013-04-30 TW TW102115443A patent/TW201406717A/zh unknown
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2014
- 2014-10-31 ZA ZA2014/07984A patent/ZA201407984B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US9290431B2 (en) | 2016-03-22 |
| TW201406717A (zh) | 2014-02-16 |
| JP2015515963A (ja) | 2015-06-04 |
| WO2013163806A1 (en) | 2013-11-07 |
| WO2013164216A1 (en) | 2013-11-07 |
| EP2844633A1 (en) | 2015-03-11 |
| US20150126777A1 (en) | 2015-05-07 |
| SG11201407133UA (en) | 2014-11-27 |
| ZA201407984B (en) | 2015-12-23 |
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