JP6153527B2 - メタクリル酸の製造 - Google Patents
メタクリル酸の製造 Download PDFInfo
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- JP6153527B2 JP6153527B2 JP2014530067A JP2014530067A JP6153527B2 JP 6153527 B2 JP6153527 B2 JP 6153527B2 JP 2014530067 A JP2014530067 A JP 2014530067A JP 2014530067 A JP2014530067 A JP 2014530067A JP 6153527 B2 JP6153527 B2 JP 6153527B2
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- methacrylic acid
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- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 title claims description 116
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 238000001556 precipitation Methods 0.000 claims description 123
- 238000000034 method Methods 0.000 claims description 82
- 239000007864 aqueous solution Substances 0.000 claims description 46
- 239000012535 impurity Substances 0.000 claims description 41
- 238000000926 separation method Methods 0.000 claims description 37
- 230000003647 oxidation Effects 0.000 claims description 26
- 238000007254 oxidation reaction Methods 0.000 claims description 26
- 239000007787 solid Substances 0.000 claims description 24
- -1 C 4 compound Chemical class 0.000 claims description 21
- 239000012452 mother liquor Substances 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 17
- 239000002245 particle Substances 0.000 claims description 14
- 238000010791 quenching Methods 0.000 claims description 11
- 238000003756 stirring Methods 0.000 claims description 11
- 230000000171 quenching effect Effects 0.000 claims description 9
- 238000000151 deposition Methods 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 239000012071 phase Substances 0.000 description 29
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 28
- 239000007789 gas Substances 0.000 description 27
- 238000001816 cooling Methods 0.000 description 23
- 239000002244 precipitate Substances 0.000 description 19
- 239000000243 solution Substances 0.000 description 19
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 18
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 17
- STNJBCKSHOAVAJ-UHFFFAOYSA-N Methacrolein Chemical compound CC(=C)C=O STNJBCKSHOAVAJ-UHFFFAOYSA-N 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000003054 catalyst Substances 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- 238000004821 distillation Methods 0.000 description 11
- 239000003960 organic solvent Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 229910001868 water Inorganic materials 0.000 description 10
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 9
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 9
- 238000000605 extraction Methods 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 8
- 238000010494 dissociation reaction Methods 0.000 description 8
- 238000000746 purification Methods 0.000 description 8
- 238000002425 crystallisation Methods 0.000 description 7
- 230000008025 crystallization Effects 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 230000008021 deposition Effects 0.000 description 6
- 230000005593 dissociations Effects 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- 238000013019 agitation Methods 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 5
- 230000032050 esterification Effects 0.000 description 5
- 238000005886 esterification reaction Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000002002 slurry Substances 0.000 description 5
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 4
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 239000001569 carbon dioxide Substances 0.000 description 4
- 229910002092 carbon dioxide Inorganic materials 0.000 description 4
- 238000002485 combustion reaction Methods 0.000 description 4
- 238000011049 filling Methods 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- NUMQCACRALPSHD-UHFFFAOYSA-N tert-butyl ethyl ether Chemical compound CCOC(C)(C)C NUMQCACRALPSHD-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 238000005119 centrifugation Methods 0.000 description 3
- 238000010574 gas phase reaction Methods 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 239000011261 inert gas Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 239000005711 Benzoic acid Substances 0.000 description 2
- 239000004215 Carbon black (E152) Substances 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
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 2
- 229940018557 citraconic acid Drugs 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000001212 derivatisation Methods 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 208000018459 dissociative disease Diseases 0.000 description 2
- 239000010419 fine particle Substances 0.000 description 2
- 238000007561 laser diffraction method Methods 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000000638 solvent extraction Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 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
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 229920006397 acrylic thermoplastic Polymers 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 159000000032 aromatic acids Chemical class 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
- 229910002090 carbon oxide Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000008394 flocculating agent 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
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 1
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 239000012495 reaction gas Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Images
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
- C07C51/43—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
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- 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)
Description
a) 粗製メタクリル酸含有水溶液中に少なくとも部分的に溶解された少なくとも1つの不純物を含む、粗製メタクリル酸含有水溶液を準備する段階、
b) 少なくとも1つの不純物の少なくとも一部を、粗製メタクリル酸含有水溶液から析出して、少なくとも1つの固体の不純物と母液とを形成する段階、
c) 少なくとも1つの固体の不純物の少なくとも一部を母液から分離して、精製されたメタクリル酸含有水溶液と、固体の不純物とを得る段階、
d) 精製されたメタクリル酸含有水溶液からメタクリル酸を分離する段階。
a1) C4化合物を気相酸化してメタクリル酸含有生成物ガスを得る段階、
a2) メタクリル酸含有生成物ガスと、急冷剤とを接触させて、粗製メタクリル酸含有水溶液中に少なくとも部分的に溶解された少なくとも1つの不純物を含む粗製メタクリル酸含有水溶液を得る段階
を含む。
aa1) MTBEを解離させて、少なくとも1つのC4化合物、好ましくは、イソブチレンおよびtert−ブチルアルコールの少なくとも1つ、およびメタノールを得る段階
を含む。
TPA含有率600ppmを有する2.5L/hの粗製MAA溶液(37% MAA)を容積8Lの撹拌タンクに供給する。撹拌タンクを13℃に冷却する。撹拌タンクは、容量約40L/hの外部ポンプを有する。27.5L/hを第一の撹拌タンクに戻してリサイクルし、且つ、12.5L/hを、ゆっくりと撹拌しながら結晶化装置(容積8L)へと供給する。この容器も、13℃に外的に冷却する。結晶化装置の上部で、10L/hを引き出し、且つ、第一の撹拌タンクへと返送する。この流れを手動で調整して、25μm未満の粒径を有する微細な粒子を結晶化装置から取り出す。前記の微細な粒子は、第一の撹拌タンクのためのシード結晶である。第二の撹拌タンクの底部で、2.5L/hが取り出され、且つ、ろ過用漏斗内でろ過される。塔底生成物は、110ppmのTPAを含有する。
Claims (10)
- メタクリル酸の製造方法であって、以下の工程段階:
a) 粗製メタクリル酸含有水溶液中に少なくとも部分的に溶解された少なくとも1つの不純物を含む、粗製メタクリル酸含有水溶液を準備する段階、
b) 少なくとも1つの不純物の少なくとも一部を、粗製メタクリル酸含有水溶液から析出して、少なくとも1つの固体の不純物と母液とを形成する段階、
c) 少なくとも1つの固体の不純物の少なくとも一部を母液から分離して、精製されたメタクリル酸含有水溶液と、固体の不純物とを得る段階、
d) 精製されたメタクリル酸含有水溶液からメタクリル酸を分離する段階
を含み、
前記段階b)において、少なくとも一部の粗製メタクリル酸含有水溶液が、第一の析出領域にみちびかれ、
第一の析出領域で得られた析出混合物の少なくとも一部が、第二の析出領域にみちびかれ、
第二の析出領域において、析出シードが、少なくとも部分的に予め形成されて、粗製メタクリル酸含有水溶液に供給され、
前記析出シードは、25μm未満の粒径を有し、且つ
段階c)において、固体の不純物の少なくとも一部を含む流れが、第二の析出領域の下方領域内に配置された出口を介して第二の析出領域を出て、分離領域にみちびかれる、
前記方法。 - 工程段階a)が、以下の工程段階:
a1) C4化合物を気相酸化してメタクリル酸含有生成物ガスを得る段階、
a2) メタクリル酸含有生成物ガスと、急冷剤とを接触させて、粗製メタクリル酸含有水溶液中に少なくとも部分的に溶解された少なくとも1つの不純物を含む粗製メタクリル酸含有水溶液を得る段階
を含む、請求項1に記載の方法。 - 粗製メタクリル酸含有水溶液を、10℃から55℃未満の範囲の温度で段階b)に供給する、請求項1または2に記載の方法。
- 段階b)において、析出が、粗製メタクリル酸含有水溶液を撹拌しながら少なくとも部分的に行われる、請求項1から3までのいずれか1項に記載の方法。
- 段階b)において、粗製メタクリル酸含有水溶液の総質量に対して30質量%より多くの粗製メタクリル酸含有水溶液が、第一の析出領域にみちびかれる、請求項1から4までのいずれか1項に記載の方法。
- 粗製メタクリル酸含有水溶液への析出シードの供給を撹拌しながら行って、析出混合物を形成する、請求項1から5までのいずれか1項に記載の方法。
- 析出シードが、第二の析出領域の側方出口を介して、粗製メタクリル酸含有水溶液に供給される、請求項1から6までのいずれか1項に記載の方法。
- 析出シードが、第一の析出領域内で、粗製メタクリル酸含有水溶液に供給される、請求項1から7までのいずれか1項に記載の方法。
- 析出混合物の少なくとも一部が、第一の析出領域の側方出口を介して第二の析出領域にみちびかれる、請求項1から8までのいずれか1項に記載の方法。
- 段階b)において、第二の析出領域内での析出混合物の冷却が行われる、請求項9に記載の方法。
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PCT/CN2011/079765 WO2013037132A1 (en) | 2011-09-16 | 2011-09-16 | Preparation of methacrylic acid |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2016123592A Division JP2016183184A (ja) | 2016-06-22 | 2016-06-22 | メタクリル酸の製造 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2014532039A JP2014532039A (ja) | 2014-12-04 |
JP6153527B2 true JP6153527B2 (ja) | 2017-06-28 |
Family
ID=47882551
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2014530067A Active JP6153527B2 (ja) | 2011-09-16 | 2011-09-16 | メタクリル酸の製造 |
Country Status (15)
Country | Link |
---|---|
US (1) | US20140187817A1 (ja) |
EP (1) | EP2755941A1 (ja) |
JP (1) | JP6153527B2 (ja) |
KR (1) | KR101877099B1 (ja) |
CN (2) | CN103796983A (ja) |
AU (1) | AU2011376834A1 (ja) |
BR (1) | BR112014006346A2 (ja) |
IN (1) | IN2014CN02726A (ja) |
MX (1) | MX2014002527A (ja) |
RU (1) | RU2014114865A (ja) |
SA (1) | SA112330848B1 (ja) |
SG (1) | SG2014012652A (ja) |
TW (1) | TW201323400A (ja) |
WO (1) | WO2013037132A1 (ja) |
ZA (1) | ZA201401599B (ja) |
Families Citing this family (3)
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EP3023408A1 (de) * | 2014-11-19 | 2016-05-25 | Evonik Röhm GmbH | Optimiertes Verfahren zur Herstellung von Methacrylsäure |
CN110461468B (zh) * | 2017-03-27 | 2022-10-14 | 三菱化学株式会社 | 催化剂以及催化剂组 |
EP3889127A1 (en) | 2020-04-03 | 2021-10-06 | Röhm GmbH | Improved safe method for tandem c-4 oxidation to methacrylic acid |
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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 |
JPH0780810B2 (ja) * | 1987-08-05 | 1995-08-30 | 三井東圧化学株式会社 | メタクリル酸水溶液の処理方法 |
JPH0780809B2 (ja) * | 1987-08-05 | 1995-08-30 | 三井東圧化学株式会社 | メタクリル酸水溶液の処理方法 |
JPH0780811B2 (ja) * | 1987-08-05 | 1995-08-30 | 三井東圧化学株式会社 | メタクリル酸水溶液の処理方法 |
JPH0764775B2 (ja) * | 1988-03-08 | 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 |
JPH05262691A (ja) * | 1992-03-19 | 1993-10-12 | Nippon Shokubai Co Ltd | フマル酸の製造方法 |
JP3417085B2 (ja) * | 1994-09-16 | 2003-06-16 | 栗田工業株式会社 | 殺菌剤包接化合物の製造方法 |
JP3279491B2 (ja) * | 1996-12-16 | 2002-04-30 | 株式会社日本触媒 | (メタ)アクリル酸の製造方法 |
JP2002128728A (ja) * | 2000-10-19 | 2002-05-09 | Mitsubishi Rayon Co Ltd | メタクリル酸の精製方法 |
DE10211686A1 (de) * | 2002-03-15 | 2003-10-02 | Stockhausen Chem Fab Gmbh | (Meth)Acrylsäurekristall und Verfahren zur Herstellung und Aufreinigung von wässriger (Meth)Acrylsäure |
DE102004034316B4 (de) * | 2004-07-15 | 2015-07-16 | Evonik Degussa Gmbh | Ein Verfahren zur Herstellung von (Meth)Acrylsäure |
EP2085376B1 (en) * | 2008-01-30 | 2012-09-05 | Evonik Röhm GmbH | Process for preparation of high purity methacrylic acid |
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SA112330848B1 (ar) | 2015-10-12 |
CN107382705A (zh) | 2017-11-24 |
ZA201401599B (en) | 2015-08-26 |
TW201323400A (zh) | 2013-06-16 |
EP2755941A1 (en) | 2014-07-23 |
AU2011376834A1 (en) | 2014-02-13 |
CN107382705B (zh) | 2021-08-10 |
MX2014002527A (es) | 2014-05-28 |
KR20140060526A (ko) | 2014-05-20 |
BR112014006346A2 (pt) | 2017-04-04 |
IN2014CN02726A (ja) | 2015-07-03 |
JP2014532039A (ja) | 2014-12-04 |
SG2014012652A (en) | 2014-08-28 |
US20140187817A1 (en) | 2014-07-03 |
CN103796983A (zh) | 2014-05-14 |
RU2014114865A (ru) | 2015-10-27 |
WO2013037132A1 (en) | 2013-03-21 |
KR101877099B1 (ko) | 2018-08-09 |
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