JP4581395B2 - (メタ)アクリル酸の精製方法および(メタ)アクリル酸エステルの製造方法 - Google Patents
(メタ)アクリル酸の精製方法および(メタ)アクリル酸エステルの製造方法 Download PDFInfo
- Publication number
- JP4581395B2 JP4581395B2 JP2003426912A JP2003426912A JP4581395B2 JP 4581395 B2 JP4581395 B2 JP 4581395B2 JP 2003426912 A JP2003426912 A JP 2003426912A JP 2003426912 A JP2003426912 A JP 2003426912A JP 4581395 B2 JP4581395 B2 JP 4581395B2
- Authority
- JP
- Japan
- Prior art keywords
- acrylic acid
- meth
- transition metal
- crude
- metal component
- 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.)
- Expired - Lifetime
Links
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 title claims description 83
- 238000000034 method Methods 0.000 title claims description 36
- 238000004519 manufacturing process Methods 0.000 title claims description 18
- 150000003624 transition metals Chemical class 0.000 claims description 36
- 229910052723 transition metal Inorganic materials 0.000 claims description 34
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 29
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 26
- 239000003729 cation exchange resin Substances 0.000 claims description 25
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical group [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims description 21
- 229910052748 manganese Inorganic materials 0.000 claims description 21
- 239000011572 manganese Substances 0.000 claims description 21
- 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 description 20
- 239000012535 impurity Substances 0.000 claims description 17
- 239000003377 acid catalyst Substances 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 239000003112 inhibitor Substances 0.000 claims description 10
- 238000006116 polymerization reaction Methods 0.000 claims description 10
- 238000000746 purification Methods 0.000 claims description 8
- 230000002378 acidificating effect Effects 0.000 claims description 7
- 150000007524 organic acids Chemical class 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 238000005886 esterification reaction Methods 0.000 description 23
- 239000007788 liquid Substances 0.000 description 20
- 238000009835 boiling Methods 0.000 description 11
- -1 Propylene, propylene Chemical group 0.000 description 9
- 238000004821 distillation Methods 0.000 description 9
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 7
- 238000007254 oxidation reaction Methods 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- 229940023913 cation exchange resins Drugs 0.000 description 5
- 239000012153 distilled water Substances 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 5
- 230000007704 transition Effects 0.000 description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- 239000007809 chemical reaction catalyst Substances 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 229910001882 dioxygen Inorganic materials 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 150000002689 maleic acids Chemical class 0.000 description 3
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 3
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 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
- 238000000926 separation method Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000011973 solid acid Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 2
- UZFMOKQJFYMBGY-UHFFFAOYSA-N 4-hydroxy-TEMPO Chemical group CC1(C)CC(O)CC(C)(C)N1[O] UZFMOKQJFYMBGY-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 230000009849 deactivation Effects 0.000 description 2
- 239000012990 dithiocarbamate Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- UOGMEBQRZBEZQT-UHFFFAOYSA-L manganese(2+);diacetate Chemical compound [Mn+2].CC([O-])=O.CC([O-])=O UOGMEBQRZBEZQT-UHFFFAOYSA-L 0.000 description 2
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical group [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229950000688 phenothiazine Drugs 0.000 description 2
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- PJYUCLOYEILMHQ-UHFFFAOYSA-N 1,2-bis(1-phenylethyl)-10h-phenothiazine Chemical compound C=1C=C2SC3=CC=CC=C3NC2=C(C(C)C=2C=CC=CC=2)C=1C(C)C1=CC=CC=C1 PJYUCLOYEILMHQ-UHFFFAOYSA-N 0.000 description 1
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 description 1
- STGFANHLXUILNY-UHFFFAOYSA-N 3,7-dioctyl-10h-phenothiazine Chemical compound C1=C(CCCCCCCC)C=C2SC3=CC(CCCCCCCC)=CC=C3NC2=C1 STGFANHLXUILNY-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
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 239000004820 Pressure-sensitive adhesive Substances 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- QYTDEUPAUMOIOP-UHFFFAOYSA-N TEMPO Chemical group CC1(C)CCCC(C)(C)N1[O] QYTDEUPAUMOIOP-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000005396 acrylic acid ester group Chemical group 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- UKRVECBFDMVBPU-UHFFFAOYSA-N ethyl 3-oxoheptanoate Chemical compound CCCCC(=O)CC(=O)OCC UKRVECBFDMVBPU-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 238000002354 inductively-coupled plasma atomic emission spectroscopy Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 229940071125 manganese acetate Drugs 0.000 description 1
- BHVPEUGTPDJECS-UHFFFAOYSA-L manganese(2+);diformate Chemical compound [Mn+2].[O-]C=O.[O-]C=O BHVPEUGTPDJECS-UHFFFAOYSA-L 0.000 description 1
- SGGOJYZMTYGPCH-UHFFFAOYSA-L manganese(2+);naphthalene-2-carboxylate Chemical compound [Mn+2].C1=CC=CC2=CC(C(=O)[O-])=CC=C21.C1=CC=CC2=CC(C(=O)[O-])=CC=C21 SGGOJYZMTYGPCH-UHFFFAOYSA-L 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 150000002990 phenothiazines Chemical class 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- FABWHQZOCFQOBG-UHFFFAOYSA-N prop-2-enoic acid;dihydrate Chemical compound O.O.OC(=O)C=C FABWHQZOCFQOBG-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940079877 pyrogallol Drugs 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
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 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
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
前処理として硫酸−硝酸の混酸にて試料を加熱分解後、蒸留水を加え、50mlの水溶液を調製した。次いで、ICP発光分析装置(JY−138U、堀場製作所社製)を使用し、ICP−AES法により、調製した測定試料の定量分析を行った。
アクリル酸99重量%及び蒸留水1重量%から成る溶液に対し、マンガン濃度として1200重量ppmと成る様に無水酢酸マンガン(II)を添加し、マンガン含有アクリル酸溶液を調製した。強酸性ポーラス型陽イオン交換樹脂(三菱化学社製の「DIAION PK−216H」)40mLを充填した固定床を25℃に維持した後、1時間当たり上記樹脂の体積の1倍量の上記マンガン含有アクリル酸溶液を通液した。通液開始2時間後から3、4、5時間後の溶出液をそれぞれ回収し、液中のマンガン濃度を分析した。通液前後のマンガン濃度推移を表1に示す。
実施例1に於て、蒸留水を添加しなかった以外は実施例1と同様の操作を行なった。通液開始2時間後から3、4時間後の溶出液をそれぞれ回収し、液中のマンガン濃度を分析した。通液前後のマンガン濃度推移を表2に示す。
実施例1に於て、添加蒸留水の濃度を5重量%に変更した以外は実施例1と同様の操作を行なった。通液開始2時間後から3、4、5、12、24時間までの溶出液をそれぞれ回収し、液中のマンガン濃度を分析した。通液前後のマンガン濃度推移を表3に示す。
実施例2に於て、1時間当たりのアクリル酸の通液量を樹脂の体積の10倍量に変更した以外は実施例2と同様の操作を行なった。通液開始0.5時間後、2時間後の溶出液をそれぞれ回収し、液中のマンガン濃度を分析した。通液前後のマンガン濃度推移を表4に示す。
実施例3に於て、蒸留水を添加しなかった以外は実施例3と同様の操作を行なった。通液開始1時間後、2.5時間後、4時間後の溶出液をそれぞれ回収し、液中のマンガン濃度を分析した。通液前後のマンガン濃度推移を表5に示す。
Claims (6)
- 遷移金属成分を不純物として含有する粗(メタ)アクリル酸を陽イオン交換樹脂と接触させて遷移金属成分を除去するに際し、陽イオン交換樹脂と粗(メタ)アクリル酸とを接触させる前に当該粗(メタ)アクリル酸に水を添加し、当該水の添加量が当該遷移金属成分を含有する粗(メタ)アクリル酸の重量に対して1〜10重量%であり、当該遷移金属成分がマンガンであることを特徴とする(メタ)アクリル酸の精製方法。
- 水の添加量が前記遷移金属成分を含有する粗(メタ)アクリル酸の重量に対して1〜5重量%である請求項1に記載の方法。
- マンガンがアクリル酸精製工程にて使用される重合防止剤に含有されているものである請求項1又は2に記載の方法。
- 酸触媒の存在下に(メタ)アクリル酸とアルコールとを反応させて(メタ)アクリル酸エステルを製造する方法において、請求項1〜3の何れかに記載の方法により(メタ)アクリル酸を得た後、当該(メタ)アクリル酸を使用して(メタ)アクリル酸エステルを製造することを特徴とする(メタ)アクリル酸エステルの製造方法。
- 酸触媒が陽イオン交換樹脂または有機酸である請求項4に記載の方法。
- 陽イオン交換樹脂が多孔質型強酸性陽イオン交換樹脂である請求項5に記載の方法。
Priority Applications (10)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2003426912A JP4581395B2 (ja) | 2003-12-24 | 2003-12-24 | (メタ)アクリル酸の精製方法および(メタ)アクリル酸エステルの製造方法 |
PCT/JP2004/014593 WO2005061428A1 (ja) | 2003-12-24 | 2004-10-04 | (メタ)アクリル酸の精製方法および(メタ)アクリル酸エステルの製造方法 |
ZA200409732A ZA200409732B (en) | 2003-12-24 | 2004-10-04 | Process for purifying (meth)acrylic acid and process for producing (meth)acrylic esters |
CNB2004800003803A CN100572354C (zh) | 2003-12-24 | 2004-10-04 | 纯化(甲基)丙烯酸的方法和制备(甲基)丙烯酸酯的方法 |
AU2004235669A AU2004235669A1 (en) | 2003-12-24 | 2004-10-04 | Process for purifying (meth)acrylic acid and process for producing (meth)acrylic esters |
ES04785807T ES2391559T3 (es) | 2003-12-24 | 2004-10-04 | Procedimiento para purificar ácido (met)acrílico y procedimiento para producir ésteres met(acrílicos) |
BRPI0405631-0A BRPI0405631B1 (pt) | 2003-12-24 | 2004-10-04 | Processo para produção de um éster (met)acrílico |
RU2004137112/04A RU2354644C2 (ru) | 2003-12-24 | 2004-10-04 | Способ очистки (мет)акриловой кислоты и способ получения эфиров (мет)ариловой кислоты |
EP04785807A EP1726578B1 (en) | 2003-12-24 | 2004-10-04 | Process for purifying (meth)acrylic acid and process for producing (meth)acrylic esters |
US11/006,806 US7148373B2 (en) | 2003-12-24 | 2004-12-08 | Process for purifying (meth)acrylic acid and process for producing (meth)acrylic esters |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2003426912A JP4581395B2 (ja) | 2003-12-24 | 2003-12-24 | (メタ)アクリル酸の精製方法および(メタ)アクリル酸エステルの製造方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2005187332A JP2005187332A (ja) | 2005-07-14 |
JP4581395B2 true JP4581395B2 (ja) | 2010-11-17 |
Family
ID=34708877
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2003426912A Expired - Lifetime JP4581395B2 (ja) | 2003-12-24 | 2003-12-24 | (メタ)アクリル酸の精製方法および(メタ)アクリル酸エステルの製造方法 |
Country Status (10)
Country | Link |
---|---|
US (1) | US7148373B2 (ja) |
EP (1) | EP1726578B1 (ja) |
JP (1) | JP4581395B2 (ja) |
CN (1) | CN100572354C (ja) |
AU (1) | AU2004235669A1 (ja) |
BR (1) | BRPI0405631B1 (ja) |
ES (1) | ES2391559T3 (ja) |
RU (1) | RU2354644C2 (ja) |
WO (1) | WO2005061428A1 (ja) |
ZA (1) | ZA200409732B (ja) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20150072214A1 (en) * | 2012-04-10 | 2015-03-12 | Sumitomo Chemical Company, Limited | Use for binder-resin composition, resin composition for treating surface of substrate for separator for nonaqueous-electrolyte secondary battery, separator for nonaqueous-electrolyte battery, method for manufacturing said separator, and nonaqueous-electrolyte secondary battery |
WO2022255371A1 (ja) | 2021-06-02 | 2022-12-08 | 株式会社日本触媒 | 易重合性化合物の製造方法 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1197558A (en) * | 1969-03-28 | 1970-07-08 | Dow Chemical Co | Acrylic Acid Purification and Polymerization |
US4269705A (en) * | 1979-04-18 | 1981-05-26 | Mitsubishi Rayon Co., Ltd. | Method for removing chromium ions from aqueous solutions of organic acids |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19536183A1 (de) * | 1995-09-28 | 1997-04-03 | Basf Ag | Verfahren zur Herstellung von Alkylestern der (Meth)acrylsäure |
JP3028925B2 (ja) | 1995-12-05 | 2000-04-04 | 株式会社日本触媒 | アクリル酸の製造方法 |
JP3880128B2 (ja) | 1997-05-08 | 2007-02-14 | 株式会社日本触媒 | アクリル酸の回収方法 |
JP3937495B2 (ja) | 1997-02-28 | 2007-06-27 | 株式会社日本触媒 | アクリル酸の回収方法 |
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 |
JP2001213839A (ja) | 2000-02-03 | 2001-08-07 | Nippon Shokubai Co Ltd | (メタ)アクリル酸の製造方法 |
-
2003
- 2003-12-24 JP JP2003426912A patent/JP4581395B2/ja not_active Expired - Lifetime
-
2004
- 2004-10-04 EP EP04785807A patent/EP1726578B1/en active Active
- 2004-10-04 WO PCT/JP2004/014593 patent/WO2005061428A1/ja not_active Application Discontinuation
- 2004-10-04 ZA ZA200409732A patent/ZA200409732B/en unknown
- 2004-10-04 BR BRPI0405631-0A patent/BRPI0405631B1/pt active IP Right Grant
- 2004-10-04 CN CNB2004800003803A patent/CN100572354C/zh active Active
- 2004-10-04 ES ES04785807T patent/ES2391559T3/es active Active
- 2004-10-04 AU AU2004235669A patent/AU2004235669A1/en not_active Abandoned
- 2004-10-04 RU RU2004137112/04A patent/RU2354644C2/ru active
- 2004-12-08 US US11/006,806 patent/US7148373B2/en active Active
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1197558A (en) * | 1969-03-28 | 1970-07-08 | Dow Chemical Co | Acrylic Acid Purification and Polymerization |
US4269705A (en) * | 1979-04-18 | 1981-05-26 | Mitsubishi Rayon Co., Ltd. | Method for removing chromium ions from aqueous solutions of organic acids |
Also Published As
Publication number | Publication date |
---|---|
ES2391559T3 (es) | 2012-11-27 |
CN1697816A (zh) | 2005-11-16 |
EP1726578A4 (en) | 2008-01-09 |
BRPI0405631A (pt) | 2005-10-11 |
RU2354644C2 (ru) | 2009-05-10 |
ZA200409732B (en) | 2007-04-25 |
WO2005061428A1 (ja) | 2005-07-07 |
AU2004235669A1 (en) | 2005-07-14 |
EP1726578A1 (en) | 2006-11-29 |
EP1726578B1 (en) | 2012-09-12 |
BRPI0405631B1 (pt) | 2019-09-17 |
JP2005187332A (ja) | 2005-07-14 |
US7148373B2 (en) | 2006-12-12 |
RU2004137112A (ru) | 2006-03-20 |
US20050171382A1 (en) | 2005-08-04 |
CN100572354C (zh) | 2009-12-23 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
KR100535323B1 (ko) | (메타)아크릴산의 정제방법 | |
TW482757B (en) | Method for producing methyl methacrylate | |
EP2046711B1 (en) | Preparation of acetic acid | |
JP5448830B2 (ja) | (メタ)アクリル酸無水物の製造方法及び保存方法、並びに(メタ)アクリル酸エステルの製造方法 | |
JP7105799B2 (ja) | 分離壁を備えた蒸留カラムを含む(メタ)アクリル酸の精製方法 | |
JP2001247510A (ja) | アクリル酸の製造方法 | |
SG178084A1 (en) | Method for producing bioresourced acrylic acid from glycerol | |
JP2005502695A (ja) | (メタ)アクリル酸エステルの製造方法 | |
KR102291247B1 (ko) | 메타크롤레인을 분리하는 방법 | |
RU2606953C2 (ru) | Способ ингибирования нежелательной радикальной полимеризации имеющейся в жидкой фазе р акриловой кислоты | |
JP3681285B2 (ja) | メタクリル酸メチルの製造方法 | |
JP4581395B2 (ja) | (メタ)アクリル酸の精製方法および(メタ)アクリル酸エステルの製造方法 | |
JPH0244296B2 (ja) | ||
JP7384519B2 (ja) | 液相pに存在するアクリル酸の望ましくないラジカル重合を抑制するための方法 | |
JP2023519280A (ja) | 液相pに存在するアクリル酸の望ましくないフリーラジカル重合を抑制する方法 | |
JP2008529988A (ja) | プロトン性溶媒を用いて抽出することによって、(メタ)アクリル酸を含有する混合物から有機化合物を回収する方法 | |
CN110049962B (zh) | 防止在纯化(甲基)丙烯酸的方法中聚合物沉积的方法 | |
US20160151770A1 (en) | Preparation of methyl methacrylate via an oxidative esterification process | |
WO2003057660A1 (fr) | Procede de decomposition d'un sous-produit de la production d'ester(meth)acrylique | |
EP0132450A1 (en) | Method of purifying methacrylic acid | |
JP2008074795A (ja) | ヒドロキシアルキルアクリレートの製造方法 | |
JP3997782B2 (ja) | (メタ)アクリル酸の製造方法 | |
SG191822A1 (en) | Method for reducing equipment fouling in (meth)acrylic acid production process | |
JPH0324459B2 (ja) | ||
JP2003176253A (ja) | (メタ)アクリル酸類の蒸留方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20060710 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20100202 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20100323 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20100803 |
|
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20100816 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 4581395 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20130910 Year of fee payment: 3 |
|
S111 | Request for change of ownership or part of ownership |
Free format text: JAPANESE INTERMEDIATE CODE: R313111 |
|
R350 | Written notification of registration of transfer |
Free format text: JAPANESE INTERMEDIATE CODE: R350 |