JP2004513089A - アクリルモノマーの安定化法 - Google Patents
アクリルモノマーの安定化法 Download PDFInfo
- Publication number
- JP2004513089A JP2004513089A JP2002531072A JP2002531072A JP2004513089A JP 2004513089 A JP2004513089 A JP 2004513089A JP 2002531072 A JP2002531072 A JP 2002531072A JP 2002531072 A JP2002531072 A JP 2002531072A JP 2004513089 A JP2004513089 A JP 2004513089A
- Authority
- JP
- Japan
- Prior art keywords
- ppm
- dtpa
- acid
- acrylic monomer
- liquid phase
- 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.)
- Withdrawn
Links
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 title claims abstract description 44
- 239000000178 monomer Substances 0.000 title claims abstract description 32
- 238000000034 method Methods 0.000 title claims abstract description 28
- 230000006641 stabilisation Effects 0.000 title description 6
- 238000011105 stabilization Methods 0.000 title description 6
- 239000003381 stabilizer Substances 0.000 claims abstract description 32
- 239000003352 sequestering agent Substances 0.000 claims abstract description 24
- 238000004821 distillation Methods 0.000 claims abstract description 18
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000007791 liquid phase Substances 0.000 claims abstract description 13
- 239000001301 oxygen Substances 0.000 claims abstract description 13
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 13
- 230000000087 stabilizing effect Effects 0.000 claims abstract description 9
- QPCDCPDFJACHGM-UHFFFAOYSA-N N,N-bis{2-[bis(carboxymethyl)amino]ethyl}glycine Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(=O)O)CCN(CC(O)=O)CC(O)=O QPCDCPDFJACHGM-UHFFFAOYSA-N 0.000 claims description 24
- 229960003330 pentetic acid Drugs 0.000 claims description 24
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 20
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 13
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 claims description 11
- 229950000688 phenothiazine Drugs 0.000 claims description 11
- 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 8
- 229960003505 mequinol Drugs 0.000 claims description 6
- 229960004337 hydroquinone Drugs 0.000 claims description 5
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical class O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 150000004897 thiazines Chemical class 0.000 claims description 4
- -1 transition metal salts Chemical class 0.000 claims description 4
- FCKYPQBAHLOOJQ-UWVGGRQHSA-N 2-[[(1s,2s)-2-[bis(carboxymethyl)amino]cyclohexyl]-(carboxymethyl)amino]acetic acid Chemical compound OC(=O)CN(CC(O)=O)[C@H]1CCCC[C@@H]1N(CC(O)=O)CC(O)=O FCKYPQBAHLOOJQ-UWVGGRQHSA-N 0.000 claims description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 3
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 229940071125 manganese acetate Drugs 0.000 claims description 3
- UOGMEBQRZBEZQT-UHFFFAOYSA-L manganese(2+);diacetate Chemical compound [Mn+2].CC([O-])=O.CC([O-])=O UOGMEBQRZBEZQT-UHFFFAOYSA-L 0.000 claims description 3
- CXKWCBBOMKCUKX-UHFFFAOYSA-M methylene blue Chemical compound [Cl-].C1=CC(N(C)C)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 CXKWCBBOMKCUKX-UHFFFAOYSA-M 0.000 claims description 3
- 229960000907 methylthioninium chloride Drugs 0.000 claims description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 3
- 229910052723 transition metal Inorganic materials 0.000 claims description 3
- UZFMOKQJFYMBGY-UHFFFAOYSA-N 4-hydroxy-TEMPO Chemical compound CC1(C)CC(O)CC(C)(C)N1[O] UZFMOKQJFYMBGY-UHFFFAOYSA-N 0.000 claims description 2
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 claims 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 12
- 229910001220 stainless steel Inorganic materials 0.000 description 9
- 239000010935 stainless steel Substances 0.000 description 9
- 238000005260 corrosion Methods 0.000 description 7
- 230000007797 corrosion Effects 0.000 description 7
- 241000196324 Embryophyta Species 0.000 description 6
- 238000000746 purification Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 239000012530 fluid Substances 0.000 description 4
- 230000002195 synergetic effect Effects 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000012856 packing Methods 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 125000005395 methacrylic acid group Chemical group 0.000 description 2
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methyl-cyclopentane Natural products CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 238000006479 redox reaction Methods 0.000 description 2
- 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
- 244000261422 Lysimachia clethroides Species 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000001944 continuous distillation Methods 0.000 description 1
- 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 1
- 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 1
- 229930003836 cresol Natural products 0.000 description 1
- WBZKQQHYRPRKNJ-UHFFFAOYSA-L disulfite Chemical compound [O-]S(=O)S([O-])(=O)=O WBZKQQHYRPRKNJ-UHFFFAOYSA-L 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 229910000358 iron sulfate Inorganic materials 0.000 description 1
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 150000002696 manganese Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B63/00—Purification; Separation; Stabilisation; Use of additives
- C07B63/04—Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/32—Separation; Purification; Stabilisation; Use of additives
- C07C253/34—Separation; Purification
-
- 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
- C07C51/50—Use of additives, e.g. for stabilisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/52—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
- C07C67/54—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0012422A FR2814741B1 (fr) | 2000-09-29 | 2000-09-29 | Procede de stabilisation de monomeres acryliques |
| PCT/FR2001/002965 WO2002026685A1 (fr) | 2000-09-29 | 2001-09-25 | Procede de stabilisation de monomeres acryliques |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2004513089A true JP2004513089A (ja) | 2004-04-30 |
| JP2004513089A5 JP2004513089A5 (https=) | 2008-11-06 |
Family
ID=8854820
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002531072A Withdrawn JP2004513089A (ja) | 2000-09-29 | 2001-09-25 | アクリルモノマーの安定化法 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US20040011638A1 (https=) |
| EP (1) | EP1324969A1 (https=) |
| JP (1) | JP2004513089A (https=) |
| KR (1) | KR100806558B1 (https=) |
| CN (1) | CN1250509C (https=) |
| AU (1) | AU2001291986A1 (https=) |
| FR (1) | FR2814741B1 (https=) |
| WO (1) | WO2002026685A1 (https=) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005343845A (ja) * | 2004-06-04 | 2005-12-15 | Hakuto Co Ltd | アクリロニトリルの重合抑制剤および重合抑制方法 |
| JP2007039403A (ja) * | 2005-08-05 | 2007-02-15 | Asahi Kasei Chemicals Corp | アクリロニトリルの分離回収方法 |
| JP2016500377A (ja) * | 2012-12-19 | 2016-01-12 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | 重合性化合物を安定させるための方法 |
| WO2023181926A1 (ja) | 2022-03-25 | 2023-09-28 | 三菱瓦斯化学株式会社 | （メタ）アクリル酸モノマーおよび／または（メタ）アクリル酸エステルモノマーの精製方法 |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10339633A1 (de) * | 2002-10-17 | 2004-04-29 | Basf Ag | Verfahren zur Herstellung von (Meth)acrylsäure und (Meth)acrylsäureestern |
| EP2135656A1 (en) * | 2008-05-30 | 2009-12-23 | Rohm and Haas Company | Method for production of purified (Meth)acrylic acid |
| EP3426287A4 (en) | 2016-03-09 | 2020-03-11 | Los Angeles Biomedical Research Institute at Harbor-UCLA Medical Center | Methods and kits for use in preventing and treating vulvovaginal candidiasis |
| CN111051488B (zh) * | 2017-08-31 | 2021-11-26 | 富士胶片株式会社 | 药液的纯化方法及药液 |
| JP7159453B2 (ja) | 2018-08-24 | 2022-10-24 | ビーエル テクノロジーズ、インコーポレイテッド | 重合を阻害するための相乗的組み合わせ |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1601979A (en) * | 1978-01-06 | 1981-11-04 | Rohm & Haas | Polymerization inhibition |
| US4929660A (en) * | 1986-03-14 | 1990-05-29 | The Kendall Company | Acrylic adhesive compositions having improved stability |
| JP2758780B2 (ja) * | 1992-04-15 | 1998-05-28 | 株式会社クラレ | （メタ）アクリル酸の重合防止方法 |
| JP3197947B2 (ja) * | 1992-05-21 | 2001-08-13 | 株式会社クラレ | （メタ）アクリル酸の重合防止法 |
| TW294658B (https=) * | 1994-06-02 | 1997-01-01 | Nippon Catalytic Chem Ind | |
| FR2750696B1 (fr) * | 1996-07-08 | 1998-10-30 | Atochem Elf Sa | Solutions aqueuses stabilisees de sels d'ammoniums quaternaires insatures |
| DE19920796A1 (de) * | 1999-05-06 | 2000-11-09 | Roehm Gmbh | Verfahren zur Herstellung von Isobornylmethacrylat |
| FR2801306B1 (fr) * | 1999-11-24 | 2001-12-28 | Atofina | Procede de purification des monomeres (meth) acryliques par distillation |
-
2000
- 2000-09-29 FR FR0012422A patent/FR2814741B1/fr not_active Expired - Fee Related
-
2001
- 2001-09-25 KR KR1020037004262A patent/KR100806558B1/ko not_active Expired - Fee Related
- 2001-09-25 CN CNB018166059A patent/CN1250509C/zh not_active Expired - Fee Related
- 2001-09-25 EP EP01972199A patent/EP1324969A1/fr not_active Withdrawn
- 2001-09-25 AU AU2001291986A patent/AU2001291986A1/en not_active Abandoned
- 2001-09-25 US US10/381,795 patent/US20040011638A1/en not_active Abandoned
- 2001-09-25 JP JP2002531072A patent/JP2004513089A/ja not_active Withdrawn
- 2001-09-25 WO PCT/FR2001/002965 patent/WO2002026685A1/fr not_active Ceased
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005343845A (ja) * | 2004-06-04 | 2005-12-15 | Hakuto Co Ltd | アクリロニトリルの重合抑制剤および重合抑制方法 |
| JP2007039403A (ja) * | 2005-08-05 | 2007-02-15 | Asahi Kasei Chemicals Corp | アクリロニトリルの分離回収方法 |
| JP2016500377A (ja) * | 2012-12-19 | 2016-01-12 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | 重合性化合物を安定させるための方法 |
| WO2023181926A1 (ja) | 2022-03-25 | 2023-09-28 | 三菱瓦斯化学株式会社 | （メタ）アクリル酸モノマーおよび／または（メタ）アクリル酸エステルモノマーの精製方法 |
| KR20240165332A (ko) | 2022-03-25 | 2024-11-22 | 미쯔비시 가스 케미칼 컴파니, 인코포레이티드 | (메트)아크릴산 모노머 및/또는 (메트)아크릴산 에스터 모노머의 정제 방법 |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2814741B1 (fr) | 2004-02-27 |
| KR100806558B1 (ko) | 2008-02-27 |
| CN1531521A (zh) | 2004-09-22 |
| AU2001291986A1 (en) | 2002-04-08 |
| WO2002026685A1 (fr) | 2002-04-04 |
| KR20030081308A (ko) | 2003-10-17 |
| US20040011638A1 (en) | 2004-01-22 |
| FR2814741A1 (fr) | 2002-04-05 |
| CN1250509C (zh) | 2006-04-12 |
| EP1324969A1 (fr) | 2003-07-09 |
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