CN102356059A - 为纯化而被稳定化的组合物以及纯化和制备(甲基)丙烯酸羟基烷基酯的方法 - Google Patents
为纯化而被稳定化的组合物以及纯化和制备(甲基)丙烯酸羟基烷基酯的方法 Download PDFInfo
- Publication number
- CN102356059A CN102356059A CN2010800119275A CN201080011927A CN102356059A CN 102356059 A CN102356059 A CN 102356059A CN 2010800119275 A CN2010800119275 A CN 2010800119275A CN 201080011927 A CN201080011927 A CN 201080011927A CN 102356059 A CN102356059 A CN 102356059A
- Authority
- CN
- China
- Prior art keywords
- composition
- purifying
- vinylformic acid
- phenylene
- amine
- 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.)
- Pending
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 120
- 238000000034 method Methods 0.000 title claims abstract description 46
- 125000002768 hydroxyalkyl group Chemical group 0.000 title claims abstract description 40
- 150000001252 acrylic acid derivatives Chemical class 0.000 title abstract 2
- 238000000746 purification Methods 0.000 title abstract 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 38
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 claims abstract description 23
- LDHQCZJRKDOVOX-UHFFFAOYSA-N 2-butenoic acid Chemical compound CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 claims description 45
- 150000001412 amines Chemical class 0.000 claims description 30
- 239000001301 oxygen Substances 0.000 claims description 27
- 229910052760 oxygen Inorganic materials 0.000 claims description 27
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 claims description 24
- 239000002585 base Substances 0.000 claims description 22
- 238000002360 preparation method Methods 0.000 claims description 18
- -1 (methyl) vinylformic acid hydroxyalkyl ester Chemical class 0.000 claims description 14
- 238000003860 storage Methods 0.000 claims description 11
- 239000011732 tocopherol Substances 0.000 claims description 11
- 229960001295 tocopherol Drugs 0.000 claims description 11
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 claims description 10
- 239000010409 thin film Substances 0.000 claims description 10
- 229930003799 tocopherol Natural products 0.000 claims description 10
- 235000010384 tocopherol Nutrition 0.000 claims description 10
- 239000011541 reaction mixture Substances 0.000 claims description 8
- 238000000926 separation method Methods 0.000 claims description 8
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 claims description 6
- 239000003513 alkali Substances 0.000 claims description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 5
- 229920001174 Diethylhydroxylamine Polymers 0.000 claims description 5
- YJADZQRQWJIEJK-UHFFFAOYSA-N azane N-phenylhydroxylamine Chemical compound N.ONC1=CC=CC=C1 YJADZQRQWJIEJK-UHFFFAOYSA-N 0.000 claims description 5
- GDEBSAWXIHEMNF-UHFFFAOYSA-O cupferron Chemical compound [NH4+].O=NN([O-])C1=CC=CC=C1 GDEBSAWXIHEMNF-UHFFFAOYSA-O 0.000 claims description 5
- 230000014759 maintenance of location Effects 0.000 claims description 5
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 4
- FVCOIAYSJZGECG-UHFFFAOYSA-N diethylhydroxylamine Chemical compound CCN(O)CC FVCOIAYSJZGECG-UHFFFAOYSA-N 0.000 claims description 4
- 150000004057 1,4-benzoquinones Chemical class 0.000 claims description 3
- 150000002118 epoxides Chemical class 0.000 claims 1
- 238000004821 distillation Methods 0.000 description 10
- 239000007789 gas Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- 150000002924 oxiranes Chemical class 0.000 description 8
- 235000004835 α-tocopherol Nutrition 0.000 description 8
- 239000002076 α-tocopherol Substances 0.000 description 8
- 229940087168 alpha tocopherol Drugs 0.000 description 7
- 238000006116 polymerization reaction Methods 0.000 description 7
- 230000006641 stabilisation Effects 0.000 description 7
- 238000011105 stabilization Methods 0.000 description 7
- 229960000984 tocofersolan Drugs 0.000 description 7
- 238000013461 design Methods 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical group O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 3
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N alpha-methacrylic acid Natural products CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-Tetramethylpiperidine Substances CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- CLBRCZAHAHECKY-UHFFFAOYSA-N [Co].[Pt] Chemical compound [Co].[Pt] CLBRCZAHAHECKY-UHFFFAOYSA-N 0.000 description 2
- 238000005265 energy consumption Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- GZIFEOYASATJEH-VHFRWLAGSA-N δ-tocopherol Chemical compound OC1=CC(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1 GZIFEOYASATJEH-VHFRWLAGSA-N 0.000 description 2
- PZZKGQBMBVYPGR-UHFFFAOYSA-N η-tocopherol Chemical compound OC1=C(C)C=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 PZZKGQBMBVYPGR-UHFFFAOYSA-N 0.000 description 2
- UZFMOKQJFYMBGY-UHFFFAOYSA-N 4-hydroxy-TEMPO Chemical compound CC1(C)CC(O)CC(C)(C)N1[O] UZFMOKQJFYMBGY-UHFFFAOYSA-N 0.000 description 1
- 241001550224 Apha Species 0.000 description 1
- GZIFEOYASATJEH-UHFFFAOYSA-N D-delta tocopherol Natural products OC1=CC(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 GZIFEOYASATJEH-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- VZWXIQHBIQLMPN-UHFFFAOYSA-N chromane Chemical class C1=CC=C2CCCOC2=C1 VZWXIQHBIQLMPN-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 235000010389 delta-tocopherol Nutrition 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 235000010382 gamma-tocopherol Nutrition 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- DOTMOQHOJINYBL-UHFFFAOYSA-N molecular nitrogen;molecular oxygen Chemical compound N#N.O=O DOTMOQHOJINYBL-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 150000002990 phenothiazines Chemical class 0.000 description 1
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000000452 restraining effect Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000006200 vaporizer Substances 0.000 description 1
- WGVKWNUPNGFDFJ-DQCZWYHMSA-N β-tocopherol Chemical compound OC1=CC(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C WGVKWNUPNGFDFJ-DQCZWYHMSA-N 0.000 description 1
- 239000002478 γ-tocopherol Substances 0.000 description 1
- QUEDXNHFTDJVIY-DQCZWYHMSA-N γ-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-DQCZWYHMSA-N 0.000 description 1
- 239000002446 δ-tocopherol Substances 0.000 description 1
Images
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/24—Preparation of carboxylic acid esters by reacting carboxylic acids or derivatives thereof with a carbon-to-oxygen ether bond, e.g. acetal, tetrahydrofuran
- C07C67/26—Preparation of carboxylic acid esters by reacting carboxylic acids or derivatives thereof with a carbon-to-oxygen ether bond, e.g. acetal, tetrahydrofuran with an oxirane ring
-
- 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
- C07C67/62—Use of additives, e.g. for stabilisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
- C07C69/533—Monocarboxylic acid esters having only one carbon-to-carbon double bond
- C07C69/54—Acrylic acid esters; Methacrylic acid esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/92—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with a hetero atom directly attached to the ring nitrogen atom
- C07D211/94—Oxygen atom, e.g. piperidine N-oxide
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/13—Phenols; Phenolates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3432—Six-membered rings
- C08K5/3435—Piperidines
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
- C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
- C09K15/06—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing oxygen
- C09K15/08—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing oxygen containing a phenol or quinone moiety
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
- C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
- C09K15/30—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing heterocyclic ring with at least one nitrogen atom as ring member
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102009001577A DE102009001577A1 (de) | 2009-03-16 | 2009-03-16 | Für eine Aufreinigung stabilisierte Zusammensetzung und Verfahren zur Aufreinigung und zur Herstellung von Hydroxyalkyl(meth)acrylaten |
| DE102009001577.9 | 2009-03-16 | ||
| PCT/EP2010/052362 WO2010105894A2 (de) | 2009-03-16 | 2010-02-25 | Für eine aufreinigung stabilisierte zusammensetzung und verfahren zur aufreinigung und zur herstellung von hydroxyalkyl(meth)acrylaten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN102356059A true CN102356059A (zh) | 2012-02-15 |
Family
ID=42563022
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2010800119275A Pending CN102356059A (zh) | 2009-03-16 | 2010-02-25 | 为纯化而被稳定化的组合物以及纯化和制备(甲基)丙烯酸羟基烷基酯的方法 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US20110306783A1 (enExample) |
| EP (1) | EP2408734A2 (enExample) |
| JP (1) | JP2012520337A (enExample) |
| KR (1) | KR20110127218A (enExample) |
| CN (1) | CN102356059A (enExample) |
| DE (1) | DE102009001577A1 (enExample) |
| RU (1) | RU2011141703A (enExample) |
| TW (1) | TW201043598A (enExample) |
| WO (1) | WO2010105894A2 (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5500965B2 (ja) * | 2009-12-14 | 2014-05-21 | 三菱レイヨン株式会社 | モノマー精製品の製造方法 |
| US8691994B2 (en) * | 2011-02-03 | 2014-04-08 | Nalco Company | Multi-component polymerization inhibitors for ethylenically unsaturated monomers |
| MX2021015554A (es) * | 2019-06-21 | 2022-02-16 | Evonik Operations Gmbh | Procedimiento para producir mono(met)acrilato de glicerol. |
| EP3904327A1 (de) | 2020-04-30 | 2021-11-03 | Röhm GmbH | Verfahren zur herstellung von hydroxyalkyl(meth)acrylsäureestern durch oxidative spaltung von methacrolein-acetalen |
| KR20240141744A (ko) | 2022-01-26 | 2024-09-27 | 바스프 에스이 | 에틸렌계 불포화 화합물의 저장 및/또는 수송 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0620206A1 (en) * | 1993-04-15 | 1994-10-19 | Nippon Shokubai Co., Ltd. | Method for inhibiting polymerization of (meth)acrylic acid and esters thereof |
| CN1293185A (zh) * | 1999-10-07 | 2001-05-02 | 株式会社日本触媒 | (甲基)丙烯酸羟烷基酯的纯化方法 |
| JP2003286228A (ja) * | 2002-03-28 | 2003-10-10 | Mitsubishi Rayon Co Ltd | ヒドロキシアルキル（メタ）アクリレートの精製方法、および、ヒドロキシアルキル（メタ）アクリレートの製造方法 |
| CN1835906A (zh) * | 2003-01-31 | 2006-09-20 | 三菱丽阳株式会社 | (甲基)丙烯酸羟烷基酯的生产设备和生产方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2853681C2 (de) | 1978-12-13 | 1980-12-18 | Merit-Werk Merten & Co Kg, 5270 Gummersbach | Kraftfahrzeug-Zünd- oder -Gliihanlaßschalter |
| DE3308804A1 (de) | 1983-03-12 | 1984-09-13 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von ethylenpolymerisaten bei druecken oberhalb von 500 bar in einem zweizonen-rohrreaktor |
| US5763658A (en) * | 1995-10-18 | 1998-06-09 | Amcol International Corporation | Method for removal of phenothiazine inhibitor from acrylic acid |
| JP2002234861A (ja) | 2001-02-09 | 2002-08-23 | Nippon Shokubai Co Ltd | ヒドロキシアルキルエステルの製造方法 |
| DE10131479B4 (de) | 2001-06-29 | 2005-05-19 | Röhm GmbH & Co. KG | Farbstabilisierung von grundstabilisierten ethylenisch ungesättigten Monomeren, insbesondere von grundstabilisierten Hydroxyalkyl(meth)acrylaten |
| WO2003035596A2 (de) * | 2001-10-19 | 2003-05-01 | Basf Aktiengesellschaft | Stabilisatorgemisch für (meth)acrylsäure und (meth)acrylsäureester |
| DE10323373A1 (de) * | 2003-05-21 | 2004-05-27 | Basf Ag | Verfahren zur Herstellung, Auf- und Weiterverarbeitung polymerisationsfähiger Verbindungen |
| GB2441399B (en) | 2007-04-03 | 2009-02-18 | Cvon Innovations Ltd | Network invitation arrangement and method |
| EP2017255A1 (de) * | 2007-07-19 | 2009-01-21 | Basf Se | Verfahren zur Herstellung von teritären Alkylestern der (Meth)Acrylsäure mit mindestens 4 Kohlenstoffatomen im Alkylrest |
| CN101959838B (zh) * | 2008-02-27 | 2015-05-13 | 巴斯夫欧洲公司 | 制备c10醇混合物的(甲基)丙烯酸酯的方法 |
-
2009
- 2009-03-16 DE DE102009001577A patent/DE102009001577A1/de not_active Withdrawn
-
2010
- 2010-02-25 EP EP10705365A patent/EP2408734A2/de not_active Withdrawn
- 2010-02-25 KR KR1020117021490A patent/KR20110127218A/ko not_active Withdrawn
- 2010-02-25 JP JP2012500171A patent/JP2012520337A/ja not_active Withdrawn
- 2010-02-25 WO PCT/EP2010/052362 patent/WO2010105894A2/de not_active Ceased
- 2010-02-25 RU RU2011141703/04A patent/RU2011141703A/ru not_active Application Discontinuation
- 2010-02-25 US US13/202,248 patent/US20110306783A1/en not_active Abandoned
- 2010-02-25 CN CN2010800119275A patent/CN102356059A/zh active Pending
- 2010-03-11 TW TW099107097A patent/TW201043598A/zh unknown
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0620206A1 (en) * | 1993-04-15 | 1994-10-19 | Nippon Shokubai Co., Ltd. | Method for inhibiting polymerization of (meth)acrylic acid and esters thereof |
| CN1293185A (zh) * | 1999-10-07 | 2001-05-02 | 株式会社日本触媒 | (甲基)丙烯酸羟烷基酯的纯化方法 |
| JP2003286228A (ja) * | 2002-03-28 | 2003-10-10 | Mitsubishi Rayon Co Ltd | ヒドロキシアルキル（メタ）アクリレートの精製方法、および、ヒドロキシアルキル（メタ）アクリレートの製造方法 |
| CN1835906A (zh) * | 2003-01-31 | 2006-09-20 | 三菱丽阳株式会社 | (甲基)丙烯酸羟烷基酯的生产设备和生产方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| KR20110127218A (ko) | 2011-11-24 |
| US20110306783A1 (en) | 2011-12-15 |
| TW201043598A (en) | 2010-12-16 |
| DE102009001577A1 (de) | 2010-09-23 |
| RU2011141703A (ru) | 2013-04-27 |
| JP2012520337A (ja) | 2012-09-06 |
| WO2010105894A3 (de) | 2011-02-24 |
| WO2010105894A2 (de) | 2010-09-23 |
| EP2408734A2 (de) | 2012-01-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN102356059A (zh) | 为纯化而被稳定化的组合物以及纯化和制备(甲基)丙烯酸羟基烷基酯的方法 | |
| KR101545031B1 (ko) | 에틸렌 글리콜 디메타크릴레이트의 제조 방법 | |
| CN102105429B (zh) | (甲基)丙烯酸酐的制造方法和保存方法、以及(甲基)丙烯酸酯的制造方法 | |
| US5294740A (en) | Preparation of formic acid by thermal cleavage of quaternary ammonium formates | |
| EP1749812A1 (en) | Polymerization inhibitor, composition containing the same and process for producing easily polymerizable compound with the polymerization inhibitor | |
| TW202239753A (zh) | 環狀伸烷基碳酸酯的工業式製造方法 | |
| KR102033744B1 (ko) | 하이드록시알킬아크릴레이트, 및 그 제조방법 | |
| EP0398633A1 (en) | Method and compositions for inhibiting polymerization of acrylic acid monomers | |
| US6696595B2 (en) | Process of the preparation of high-purity alkyladamantyl esters | |
| CN101910105B (zh) | α-羟甲基丙烯酸酯化合物类及其制造方法 | |
| JP4545459B2 (ja) | 環式骨格含有（メタ）アクリル酸エステルの製造方法 | |
| EP3255036B1 (en) | Method for producing 2-aminoethylmethacrylate hydrochloride | |
| HK1164275A (en) | Composition stabilized for purification and method for purifying and for producing hydroxyalkyl(meth)acrylates | |
| CN113614060B (zh) | 聚合级丙烯酸的生产 | |
| CN115197066A (zh) | 直链碳酸酯及其制备方法 | |
| JP5762809B2 (ja) | 環状ホルマールの精製方法 | |
| CN101085733A (zh) | 一种脱除微量杂质醛制备精丙烯酸的方法 | |
| JPH0952861A (ja) | （メタ）アクリル酸の重合防止法 | |
| JP3837966B2 (ja) | ポリテトラメチレンエーテルグリコールの製造方法 | |
| JP4657701B2 (ja) | アルミン酸エステル化合物及びその製造方法 | |
| JPH07149749A (ja) | メタクリル酸グリシジルの精製法 | |
| WO2023181926A1 (ja) | （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 | |
| JP5215600B2 (ja) | Ｎ−アルキルボラジンの製造方法 | |
| JP2008127352A (ja) | Ｎ−アルキルボラジンの製造方法 | |
| JPH0454145A (ja) | アルキレングリコールモノビニルエーテル類の精製方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| REG | Reference to a national code |
Ref country code: HK Ref legal event code: DE Ref document number: 1164275 Country of ref document: HK |
|
| C02 | Deemed withdrawal of patent application after publication (patent law 2001) | ||
| WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20120215 |
|
| REG | Reference to a national code |
Ref country code: HK Ref legal event code: WD Ref document number: 1164275 Country of ref document: HK |