ZA200603915B - Method of purifying (meth) acrylic acid - Google Patents

Method of purifying (meth) acrylic acid Download PDF

Info

Publication number: ZA200603915B
Authority: ZA; South Africa
Prior art keywords: acrylic acid; meth; copper; purifying; crude
Prior art date: 2003-11-28

Application number

ZA200603915A

Other languages

English (en)

Inventor

Yada Shuhei

Ogawa Yasushi

Takasaki Kenji

Suzuki Yoshiro

Original Assignee

Mitsubishi Chem Corp

Priority date (The priority date 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 date listed.)

2003-11-28

Filing date

2004-09-08

Publication date

2007-09-26

2004-09-08 Application filed by Mitsubishi Chem Corp filed Critical Mitsubishi Chem Corp

2007-09-26 Publication of ZA200603915B publication Critical patent/ZA200603915B/en

Links

CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 title claims description 105
238000000034 method Methods 0.000 title claims description 67
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 134
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 103
239000007788 liquid Substances 0.000 claims description 87
239000007789 gas Substances 0.000 claims description 81
238000004821 distillation Methods 0.000 claims description 80
238000006116 polymerization reaction Methods 0.000 claims description 60
238000010992 reflux Methods 0.000 claims description 52
239000002253 acid Substances 0.000 claims description 47
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 43
239000010949 copper Substances 0.000 claims description 40
229910052802 copper Inorganic materials 0.000 claims description 40
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 37
239000001301 oxygen Substances 0.000 claims description 37
229910052760 oxygen Inorganic materials 0.000 claims description 37
239000003112 inhibitor Substances 0.000 claims description 33
-1 phenothiazine compound Chemical class 0.000 claims description 33
OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 24
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 21
150000001875 compounds Chemical class 0.000 claims description 20
230000003647 oxidation Effects 0.000 claims description 19
238000007254 oxidation reaction Methods 0.000 claims description 19
239000012808 vapor phase Substances 0.000 claims description 13
230000003197 catalytic effect Effects 0.000 claims description 11
KGGZTXSNARMULX-UHFFFAOYSA-L copper;dicarbamodithioate Chemical compound [Cu+2].NC([S-])=S.NC([S-])=S KGGZTXSNARMULX-UHFFFAOYSA-L 0.000 claims description 11
229940063559 methacrylic acid Drugs 0.000 claims description 10
229950000688 phenothiazine Drugs 0.000 claims description 10
230000008569 process Effects 0.000 claims description 9
229940116318 copper carbonate Drugs 0.000 claims description 6
GEZOTWYUIKXWOA-UHFFFAOYSA-L copper;carbonate Chemical compound [Cu+2].[O-]C([O-])=O GEZOTWYUIKXWOA-UHFFFAOYSA-L 0.000 claims description 6
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 5
JJLJMEJHUUYSSY-UHFFFAOYSA-L Copper hydroxide Chemical compound [OH-].[OH-].[Cu+2] JJLJMEJHUUYSSY-UHFFFAOYSA-L 0.000 claims description 4
239000012990 dithiocarbamate Substances 0.000 claims description 4
DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 claims description 3
229910000009 copper(II) carbonate Inorganic materials 0.000 claims description 3
IXPUJMULXNNEHS-UHFFFAOYSA-L copper;n,n-dibutylcarbamodithioate Chemical compound [Cu+2].CCCCN(C([S-])=S)CCCC.CCCCN(C([S-])=S)CCCC IXPUJMULXNNEHS-UHFFFAOYSA-L 0.000 claims description 3
235000019854 cupric carbonate Nutrition 0.000 claims description 3
239000011646 cupric carbonate Substances 0.000 claims description 3
WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 claims description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 3
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 claims description 2
QNTARNCGFNQQRP-UHFFFAOYSA-N 5-carbamothioylsulfanylpentyl carbamodithioate Chemical compound NC(=S)SCCCCCSC(N)=S QNTARNCGFNQQRP-UHFFFAOYSA-N 0.000 claims description 2
BIVUUOPIAYRCAP-UHFFFAOYSA-N aminoazanium;chloride Chemical compound Cl.NN BIVUUOPIAYRCAP-UHFFFAOYSA-N 0.000 claims description 2
OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 claims description 2
229910052757 nitrogen Inorganic materials 0.000 claims description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims 2
229910002092 carbon dioxide Inorganic materials 0.000 claims 1
239000001569 carbon dioxide Substances 0.000 claims 1
UQMKZLGQBFCRSN-UHFFFAOYSA-L copper;n,n-dipropylcarbamodithioate Chemical compound [Cu+2].CCCN(C([S-])=S)CCC.CCCN(C([S-])=S)CCC UQMKZLGQBFCRSN-UHFFFAOYSA-L 0.000 claims 1
125000005395 methacrylic acid group Chemical group 0.000 claims 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
KZCOBXFFBQJQHH-UHFFFAOYSA-N octane-1-thiol Chemical compound CCCCCCCCS KZCOBXFFBQJQHH-UHFFFAOYSA-N 0.000 claims 1
229920000642 polymer Polymers 0.000 claims 1
229940114077 acrylic acid Drugs 0.000 description 99
239000012535 impurity Substances 0.000 description 22
238000012856 packing Methods 0.000 description 21
229940048053 acrylate Drugs 0.000 description 18
238000007792 addition Methods 0.000 description 17
239000000047 product Substances 0.000 description 17
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
238000009835 boiling Methods 0.000 description 15
239000002904 solvent Substances 0.000 description 15
238000004519 manufacturing process Methods 0.000 description 14
239000000203 mixture Substances 0.000 description 14
239000000126 substance Substances 0.000 description 14
HYBBIBNJHNGZAN-UHFFFAOYSA-N Furaldehyde Natural products O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 12
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 12
230000003405 preventing effect Effects 0.000 description 12
239000002994 raw material Substances 0.000 description 12
238000000746 purification Methods 0.000 description 11
150000001299 aldehydes Chemical class 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
238000006243 chemical reaction Methods 0.000 description 9
239000007921 spray Substances 0.000 description 9
HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 8
230000015572 biosynthetic process Effects 0.000 description 8
230000000694 effects Effects 0.000 description 8
238000005755 formation reaction Methods 0.000 description 8
239000000243 solution Substances 0.000 description 8
230000001629 suppression Effects 0.000 description 8
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 7
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 7
239000000463 material Substances 0.000 description 7
238000000926 separation method Methods 0.000 description 7
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 6
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 6
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 6
239000011976 maleic acid Substances 0.000 description 6
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 6
ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 5
150000002689 maleic acids Chemical class 0.000 description 5
238000011084 recovery Methods 0.000 description 5
229910001220 stainless steel Inorganic materials 0.000 description 5
WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 4
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
229940095076 benzaldehyde Drugs 0.000 description 4
238000005260 corrosion Methods 0.000 description 4
230000007797 corrosion Effects 0.000 description 4
238000000354 decomposition reaction Methods 0.000 description 4
229910052751 metal Inorganic materials 0.000 description 4
239000002184 metal Substances 0.000 description 4
150000002739 metals Chemical class 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 4
239000004583 superabsorbent polymers (SAPs) Substances 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
238000007599 discharging Methods 0.000 description 3
239000012530 fluid Substances 0.000 description 3
230000001965 increasing effect Effects 0.000 description 3
FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 3
229940044600 maleic anhydride Drugs 0.000 description 3
239000001294 propane Substances 0.000 description 3
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 3
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
239000010935 stainless steel Substances 0.000 description 3
229920000247 superabsorbent polymer Polymers 0.000 description 3
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 description 2
NIUAGEVCVWHMTA-UHFFFAOYSA-N 5-(4-iodophenyl)-1-(4-methylsulfonylphenyl)-3-(trifluoromethyl)pyrazole Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1C(C=2C=CC(I)=CC=2)=CC(C(F)(F)F)=N1 NIUAGEVCVWHMTA-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
241001124569 Lycaenidae Species 0.000 description 2
230000002411 adverse Effects 0.000 description 2
WQAQPCDUOCURKW-UHFFFAOYSA-N butanethiol Chemical compound CCCCS WQAQPCDUOCURKW-UHFFFAOYSA-N 0.000 description 2
150000001735 carboxylic acids Chemical class 0.000 description 2
YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
239000003729 cation exchange resin Substances 0.000 description 2
230000000052 comparative effect Effects 0.000 description 2
238000001816 cooling Methods 0.000 description 2
235000014987 copper Nutrition 0.000 description 2
OBBCYCYCTJQCCK-UHFFFAOYSA-L copper;n,n-diethylcarbamodithioate Chemical compound [Cu+2].CCN(CC)C([S-])=S.CCN(CC)C([S-])=S OBBCYCYCTJQCCK-UHFFFAOYSA-L 0.000 description 2
ZOUQIAGHKFLHIA-UHFFFAOYSA-L copper;n,n-dimethylcarbamodithioate Chemical compound [Cu+2].CN(C)C([S-])=S.CN(C)C([S-])=S ZOUQIAGHKFLHIA-UHFFFAOYSA-L 0.000 description 2
XPLSDXJBKRIVFZ-UHFFFAOYSA-L copper;prop-2-enoate Chemical compound [Cu+2].[O-]C(=O)C=C.[O-]C(=O)C=C XPLSDXJBKRIVFZ-UHFFFAOYSA-L 0.000 description 2
238000010586 diagram Methods 0.000 description 2
239000000539 dimer Substances 0.000 description 2
230000009977 dual effect Effects 0.000 description 2
230000002708 enhancing effect Effects 0.000 description 2
230000004907 flux Effects 0.000 description 2
238000004817 gas chromatography Methods 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
150000002429 hydrazines Chemical class 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
238000007689 inspection Methods 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
239000002245 particle Substances 0.000 description 2
239000011148 porous material Substances 0.000 description 2
239000012264 purified product Substances 0.000 description 2
WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 2
241000894007 species Species 0.000 description 2
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
238000012546 transfer Methods 0.000 description 2
FBOUIAKEJMZPQG-AWNIVKPZSA-N (1E)-1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)pent-1-en-3-ol Chemical compound C1=NC=NN1/C(C(O)C(C)(C)C)=C/C1=CC=C(Cl)C=C1Cl FBOUIAKEJMZPQG-AWNIVKPZSA-N 0.000 description 1
WHBHBVVOGNECLV-OBQKJFGGSA-N 11-deoxycortisol Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 WHBHBVVOGNECLV-OBQKJFGGSA-N 0.000 description 1
RIZUCYSQUWMQLX-UHFFFAOYSA-N 2,3-dimethylbenzoic acid Chemical compound CC1=CC=CC(C(O)=O)=C1C RIZUCYSQUWMQLX-UHFFFAOYSA-N 0.000 description 1
QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
CYUZOYPRAQASLN-UHFFFAOYSA-N 3-prop-2-enoyloxypropanoic acid Chemical compound OC(=O)CCOC(=O)C=C CYUZOYPRAQASLN-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
FUSNOPLQVRUIIM-UHFFFAOYSA-N 4-amino-2-(4,4-dimethyl-2-oxoimidazolidin-1-yl)-n-[3-(trifluoromethyl)phenyl]pyrimidine-5-carboxamide Chemical compound O=C1NC(C)(C)CN1C(N=C1N)=NC=C1C(=O)NC1=CC=CC(C(F)(F)F)=C1 FUSNOPLQVRUIIM-UHFFFAOYSA-N 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
101100179596 Caenorhabditis elegans ins-3 gene Proteins 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
241000272470 Circus Species 0.000 description 1
239000005749 Copper compound Substances 0.000 description 1
239000005750 Copper hydroxide Substances 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
241000243251 Hydra Species 0.000 description 1
241001580033 Imma Species 0.000 description 1
VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 description 1
UBUCNCOMADRQHX-UHFFFAOYSA-N N-Nitrosodiphenylamine Chemical compound C=1C=CC=CC=1N(N=O)C1=CC=CC=C1 UBUCNCOMADRQHX-UHFFFAOYSA-N 0.000 description 1
ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
229920002125 Sokalan® Polymers 0.000 description 1
GNVMUORYQLCPJZ-UHFFFAOYSA-M Thiocarbamate Chemical compound NC([S-])=O GNVMUORYQLCPJZ-UHFFFAOYSA-M 0.000 description 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
235000010724 Wisteria floribunda Nutrition 0.000 description 1
NDMWPODQAYELNE-UHFFFAOYSA-L [Cu+2].NC([S-])=S.NC([S-])=S.C=COC=C Chemical compound [Cu+2].NC([S-])=S.NC([S-])=S.C=COC=C NDMWPODQAYELNE-UHFFFAOYSA-L 0.000 description 1
230000002159 abnormal effect Effects 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
229920006397 acrylic thermoplastic Polymers 0.000 description 1
230000002730 additional effect Effects 0.000 description 1
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical class OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 1
150000001335 aliphatic alkanes Chemical class 0.000 description 1
150000001336 alkenes Chemical class 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
239000004305 biphenyl Substances 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
125000006267 biphenyl group Chemical group 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
235000013877 carbamide Nutrition 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
238000004040 coloring Methods 0.000 description 1
238000011109 contamination Methods 0.000 description 1
150000001880 copper compounds Chemical class 0.000 description 1
229910001956 copper hydroxide Inorganic materials 0.000 description 1
CMRVDFLZXRTMTH-UHFFFAOYSA-L copper;2-carboxyphenolate Chemical compound [Cu+2].OC1=CC=CC=C1C([O-])=O.OC1=CC=CC=C1C([O-])=O CMRVDFLZXRTMTH-UHFFFAOYSA-L 0.000 description 1
HFDWIMBEIXDNQS-UHFFFAOYSA-L copper;diformate Chemical compound [Cu+2].[O-]C=O.[O-]C=O HFDWIMBEIXDNQS-UHFFFAOYSA-L 0.000 description 1
238000005336 cracking Methods 0.000 description 1
229930003836 cresol Natural products 0.000 description 1
229960003280 cupric chloride Drugs 0.000 description 1
PYRZPBDTPRQYKG-UHFFFAOYSA-N cyclopentene-1-carboxylic acid Chemical compound OC(=O)C1=CCCC1 PYRZPBDTPRQYKG-UHFFFAOYSA-N 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
238000011161 development Methods 0.000 description 1
230000018109 developmental process Effects 0.000 description 1
150000004659 dithiocarbamates Chemical class 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000002778 food additive Substances 0.000 description 1
235000013373 food additive Nutrition 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
239000012493 hydrazine sulfate Substances 0.000 description 1
229910000377 hydrazine sulfate Inorganic materials 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
239000012212 insulator Substances 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 description 1
230000007775 late Effects 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
239000012046 mixed solvent Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
239000000178 monomer Substances 0.000 description 1
150000002832 nitroso derivatives Chemical class 0.000 description 1
GYHFUZHODSMOHU-UHFFFAOYSA-N nonanal Chemical compound CCCCCCCCC=O GYHFUZHODSMOHU-UHFFFAOYSA-N 0.000 description 1
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
229960003903 oxygen Drugs 0.000 description 1
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
229940067157 phenylhydrazine Drugs 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
230000002265 prevention Effects 0.000 description 1
239000008213 purified water Substances 0.000 description 1
229940079877 pyrogallol Drugs 0.000 description 1
230000036647 reaction Effects 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
230000009467 reduction Effects 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 1
229960001755 resorcinol Drugs 0.000 description 1
238000001577 simple distillation Methods 0.000 description 1
239000010802 sludge Substances 0.000 description 1
ACXGJHCPFCFILV-UHFFFAOYSA-M sodium;2-(4-chloro-2-methylphenoxy)acetate;3,6-dichloro-2-methoxybenzoic acid Chemical compound [Na+].COC1=C(Cl)C=CC(Cl)=C1C(O)=O.CC1=CC(Cl)=CC=C1OCC([O-])=O ACXGJHCPFCFILV-UHFFFAOYSA-M 0.000 description 1
238000005507 spraying Methods 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
150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 1
150000003585 thioureas Chemical class 0.000 description 1
239000013638 trimer Substances 0.000 description 1
150000003672 ureas Chemical class 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
SYOKIDBDQMKNDQ-XWTIBIIYSA-N vildagliptin Chemical compound C1C(O)(C2)CC(C3)CC1CC32NCC(=O)N1CCC[C@H]1C#N SYOKIDBDQMKNDQ-XWTIBIIYSA-N 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 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
- C07C51/43—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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Crystallography & Structural Chemistry (AREA)
Engineering & Computer Science (AREA)
Oil, Petroleum & Natural Gas (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Vaporization, Distillation, Condensation, Sublimation, And Cold Traps (AREA)

ZA200603915A 2003-11-28 2004-09-08 Method of purifying (meth) acrylic acid ZA200603915B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP2003399124		2003-11-28

Publications (1)

Publication Number	Publication Date
ZA200603915B true ZA200603915B (en)	2007-09-26

Family

ID=34631592

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
ZA200603915A ZA200603915B (en)	2003-11-28	2004-09-08	Method of purifying (meth) acrylic acid

Country Status (9)

Country	Link
US (1)	US20060205979A1 (fr)
EP (1)	EP1688407B1 (fr)
CN (1)	CN1305832C (fr)
AU (1)	AU2004293259A1 (fr)
BR (1)	BRPI0416962A8 (fr)
ES (1)	ES2621114T3 (fr)
RU (1)	RU2350598C2 (fr)
WO (1)	WO2005051883A1 (fr)
ZA (1)	ZA200603915B (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2005336141A (ja) *	2004-05-31	2005-12-08	Mitsubishi Chemicals Corp	アクリル酸の製造方法
DE102009058058A1 (de) *	2009-12-14	2011-06-16	Basf Se	Verfahren zur Polymerisationsinhibierung von (Meth)acrylsäure und/oder Meth)acrylsäureestern
DE102010042216A1 (de) *	2010-10-08	2011-06-09	Basf Se	Verfahren zur Hemmung der unerwünschten radikalischen Polymerisation von in einer flüssigen Phase P befindlicher Acrylsäure
JP2016520096A (ja) *	2013-05-20	2016-07-11	サウディベーシックインダストリーズコーポレイション	酢酸及びアクリル酸の精製方法
FR3041958B1 (fr) *	2015-10-06	2019-06-14	Arkema France	Procede ameliore de production d’acide (meth)acrylique de grade polymere
KR101984280B1 (ko)	2015-11-27	2019-05-30	주식회사 엘지화학	(메트)아크릴산의 제조 방법

Family Cites Families (36)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2241175A (en) *	1939-01-30	1941-05-06	Norton Co	Method of distilling monomeric polymerizable substances
DE1720530A1 (de) *	1967-01-25	1971-07-01	Daicel Ltd	Verfahren zur Herstellung von Polymerisationsprodukten
JPS5115012B2 (fr) *	1971-12-24	1976-05-13
US4021310A (en) *	1972-12-22	1977-05-03	Nippon Shokubai Kagaku Kogyo Co., Ltd.	Method for inhibiting the polymerization of acrylic acid or its esters
JPS5234606B2 (fr) *	1972-12-22	1977-09-05
US4317926A (en) *	1978-01-19	1982-03-02	Nippon Shokubai Kagaku Kogyo Co., Ltd.	Process for preparing and recovering acrylic acid
US4260821A (en) *	1979-03-15	1981-04-07	Halcon Research And Development Corp.	Minimizing polymerization during recovery 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
EP0034402B1 (fr) *	1980-02-05	1984-08-29	Imperial Chemical Industries Plc	Procédé de préparation de dérivés d'éthers diphényliques fluorosubstitués et benzènes halogénés fluorosubstitués à utiliser dans ce procédé
SU981313A1 (ru) *	1980-11-14	1982-12-15	Научно-Исследовательский Институт Механики И Физики При Саратовском Ордена Трудового Красного Знамени Государственном Университете Им.Н.Г.Чернышевского	Способ стабилизации эфиров акриловой кислоты
EP0312191B1 (fr) *	1987-10-09	1992-09-16	MITSUI TOATSU CHEMICALS, Inc.	Procédé pour l'épuration de l'acide méthacrylique
DE3837955A1 (de) *	1987-11-13	1989-05-24	Basf Ag	Kontinuierliches destillationsverfahren zur gewinnung von beispielsweise hydrochinon-stabilisierter acrylsaeure
US4959885A (en) *	1990-01-12	1990-10-02	Royal Applicance Mfg. Co.	Vacuum cleaner
SG85575A1 (en) *	1993-12-24	2002-01-15	Sumitomo Chemical Co	Process for purifying acrylic acid
JP2003073328A (ja) *	1993-12-24	2003-03-12	Sumitomo Chem Co Ltd	アクリル酸の精製方法
US5523480A (en) *	1994-03-28	1996-06-04	Rohm And Haas Company	Process for purifying unsaturated carboxylic acids using distillation and melt crystallization
BR9508592A (pt) *	1994-08-18	1997-12-23	Ici Plc	Processo para preparar ésteres acrílicos refinados
US5482597A (en) *	1994-11-23	1996-01-09	Basf Aktiengesellschaft	Purification of crude (meth)acrylic acid
TW407145B (en) *	1995-10-02	2000-10-01	Idemitsu Pertrochemical Co Ltd	Process for inhibiting polymerization of a vinyl compound
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
EP1026145B1 (fr) *	1999-01-29	2003-04-02	Mitsubishi Chemical Corporation	Procédé pour la purification de l'acide acrylique
JP4242964B2 (ja) *	1999-03-09	2009-03-25	株式会社日本触媒	（メタ）アクリル酸および／またはそのエステルの精製方法
JP2000344688A (ja) *	1999-06-04	2000-12-12	Mitsubishi Chemicals Corp	易重合性化合物の精製方法
JP2001213839A (ja) *	2000-02-03	2001-08-07	Nippon Shokubai Co Ltd	（メタ）アクリル酸の製造方法
AU2002344613A1 (en) *	2001-10-30	2003-06-10	Mitsubishi Chemical Corporation	Method for purifying (meth)acrylic acid
WO2003043968A1 (fr) *	2001-11-20	2003-05-30	Mitsubishi Chemical Corporation	Procede permettant de produire des composes a base d'acide (meth)acrylique
CN100509745C (zh) *	2001-11-21	2009-07-08	三菱化学株式会社	供应环境气体的方法
JP2003160532A (ja) *	2001-11-28	2003-06-03	Mitsubishi Chemicals Corp	（メタ）アクリル酸の製造方法
CN1318374C (zh) *	2001-11-28	2007-05-30	三菱化学株式会社	制备（甲基）丙烯酸化合物的方法
JP4016650B2 (ja) *	2001-12-14	2007-12-05	三菱化学株式会社	（メタ）アクリル酸の製造方法
CN1274658C (zh) *	2001-12-19	2006-09-13	三菱化学株式会社	（甲基）丙烯酸的制造方法
AU2003201911A1 (en) *	2002-01-08	2003-07-24	Mitsubishi Chemical Corporation	Method of preventing clogging of apparatus for handling (meth)acrylic acid and ester thereof
WO2003064367A1 (fr) *	2002-01-29	2003-08-07	Mitsubishi Chemical Corporation	Procede de production d'acide (meth)acrylique
JP2003342231A (ja) *	2002-05-23	2003-12-03	Mitsubishi Rayon Co Ltd	（メタ）アクリル酸またはそのエステルの貯蔵方法
JP3971974B2 (ja) *	2002-09-03	2007-09-05	三菱化学株式会社	（メタ）アクリル酸類の製造方法
JP4412019B2 (ja) *	2004-03-23	2010-02-10	三菱化学株式会社	（メタ）アクリル酸およびそのエステルの取り扱い装置の閉塞防止方法

2004
- 2004-09-08 CN CNB2004800005601A patent/CN1305832C/zh not_active Expired - Lifetime
- 2004-09-08 WO PCT/JP2004/013052 patent/WO2005051883A1/fr not_active Ceased
- 2004-09-08 RU RU2006122956/04A patent/RU2350598C2/ru active
- 2004-09-08 AU AU2004293259A patent/AU2004293259A1/en not_active Abandoned
- 2004-09-08 ZA ZA200603915A patent/ZA200603915B/en unknown
- 2004-09-08 ES ES04787735.2T patent/ES2621114T3/es not_active Expired - Lifetime
- 2004-09-08 EP EP04787735.2A patent/EP1688407B1/fr not_active Expired - Lifetime
- 2004-09-08 BR BRPI0416962A patent/BRPI0416962A8/pt not_active Application Discontinuation
2006
- 2006-05-16 US US11/434,067 patent/US20060205979A1/en not_active Abandoned

Also Published As

Publication number	Publication date
EP1688407A1 (fr)	2006-08-09
WO2005051883A1 (fr)	2005-06-09
BRPI0416962A (pt)	2007-02-21
CN1305832C (zh)	2007-03-21
BRPI0416962A8 (pt)	2017-12-19
CN1697818A (zh)	2005-11-16
US20060205979A1 (en)	2006-09-14
EP1688407A4 (fr)	2006-12-27
ES2621114T3 (es)	2017-07-03
RU2006122956A (ru)	2008-01-10
RU2350598C2 (ru)	2009-03-27
EP1688407B1 (fr)	2017-01-25
AU2004293259A1 (en)	2005-06-09

Publication	Publication Date	Title
US8242308B2 (en)	2012-08-14	Process for producing acrylic acid
US7473338B2 (en)	2009-01-06	Distillation apparatus for readily polymerizable compound
EP1818324B1 (fr)	2013-02-20	Procédé de production dýacide acrylique (Meth)
CN100389848C (zh)	2008-05-28	一种薄膜蒸发器及其在（甲基）丙烯酸精制方法中的应用
KR100932467B1 (ko)	2009-12-17	아크릴산의 제조방법
JP5378207B2 (ja)	2013-12-25	（メタ）アクリル酸の製造方法
JP4032033B2 (ja)	2008-01-16	高純度メタクリル酸の製造法
US8044238B2 (en)	2011-10-25	Method for production of purified (meth)acrylic acid
KR101091736B1 (ko)	2011-12-08	수성 (메트)아크릴산의 생성 방법
ZA200603915B (en)	2007-09-26	Method of purifying (meth) acrylic acid
JP2005179352A (ja)	2005-07-07	（メタ）アクリル酸の精製方法
JP4575383B2 (ja)	2010-11-04	アクリル酸含有液体の精留分離法
US7476299B2 (en)	2009-01-13	Vessel for easily polymerizable compound
JP4300224B2 (ja)	2009-07-22	アクリル酸の製造方法
VON ACRYLSÁURE	0	LLLLLGGG GGGGGGG LLLLL GGGGGG (51) Int Cl: Cp7C 51/44 (200601) Cŋ7C 57%) 4 (200601)(86) International application number
JP2005230584A (ja)	2005-09-02	易重合性化合物用の塔設備