CA2152873C - Procede de fabrication de methacrylate de methyle sans diacetyle - Google Patents
Procede de fabrication de methacrylate de methyle sans diacetyleInfo
- Publication number
- CA2152873C CA2152873C CA002152873A CA2152873A CA2152873C CA 2152873 C CA2152873 C CA 2152873C CA 002152873 A CA002152873 A CA 002152873A CA 2152873 A CA2152873 A CA 2152873A CA 2152873 C CA2152873 C CA 2152873C
- Authority
- CA
- Canada
- Prior art keywords
- methyl methacrylate
- diamine
- diacetyl
- aromatic
- fact
- 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 - Fee Related
Links
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 title claims abstract description 37
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 title claims abstract description 34
- 238000000034 method Methods 0.000 title claims description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 30
- 125000003118 aryl group Chemical group 0.000 claims abstract description 19
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000012535 impurity Substances 0.000 claims abstract description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 10
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims abstract description 7
- 238000009835 boiling Methods 0.000 claims abstract description 6
- MWFMGBPGAXYFAR-UHFFFAOYSA-N 2-hydroxy-2-methylpropanenitrile Chemical compound CC(C)(O)C#N MWFMGBPGAXYFAR-UHFFFAOYSA-N 0.000 claims abstract description 4
- 238000007171 acid catalysis Methods 0.000 claims abstract description 3
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910052921 ammonium sulfate Inorganic materials 0.000 claims abstract description 3
- 235000011130 ammonium sulphate Nutrition 0.000 claims abstract description 3
- 238000004821 distillation Methods 0.000 claims description 13
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 8
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N 1,4-Benzenediol Natural products OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 7
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 239000000178 monomer Substances 0.000 claims description 3
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 2
- 239000003112 inhibitor Substances 0.000 claims description 2
- 238000000622 liquid--liquid extraction Methods 0.000 claims description 2
- 229950000688 phenothiazine Drugs 0.000 claims description 2
- 238000006116 polymerization reaction Methods 0.000 claims description 2
- 238000000638 solvent extraction Methods 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 5
- 150000004985 diamines Chemical class 0.000 abstract description 3
- 235000011149 sulphuric acid Nutrition 0.000 abstract 2
- 238000002955 isolation Methods 0.000 abstract 1
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 4
- 230000008030 elimination Effects 0.000 description 3
- 238000003379 elimination reaction Methods 0.000 description 3
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
- 238000001944 continuous distillation Methods 0.000 description 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000004383 yellowing Methods 0.000 description 2
- -1 1,2-ethylene Chemical group 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000000998 batch distillation Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
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
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
-
- 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
- C07C67/60—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR94.08103 | 1994-06-30 | ||
| FR9408103A FR2721923B1 (fr) | 1994-06-30 | 1994-06-30 | Procede de fabrication de methacrylate de methyle sans diacetyle |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2152873A1 CA2152873A1 (fr) | 1995-12-31 |
| CA2152873C true CA2152873C (fr) | 1998-10-27 |
Family
ID=9464864
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002152873A Expired - Fee Related CA2152873C (fr) | 1994-06-30 | 1995-06-28 | Procede de fabrication de methacrylate de methyle sans diacetyle |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US5585514A (OSRAM) |
| EP (1) | EP0690041B1 (OSRAM) |
| JP (1) | JP2783772B2 (OSRAM) |
| KR (1) | KR0174109B1 (OSRAM) |
| CN (1) | CN1125713A (OSRAM) |
| AT (1) | ATE162173T1 (OSRAM) |
| CA (1) | CA2152873C (OSRAM) |
| CZ (1) | CZ173395A3 (OSRAM) |
| DE (1) | DE69501437T2 (OSRAM) |
| DK (1) | DK0690041T3 (OSRAM) |
| ES (1) | ES2113160T3 (OSRAM) |
| FR (1) | FR2721923B1 (OSRAM) |
| GR (1) | GR3026194T3 (OSRAM) |
| TW (1) | TW294660B (OSRAM) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001288147A (ja) * | 2000-04-11 | 2001-10-16 | Mitsubishi Rayon Co Ltd | メタクリル酸メチルの精製方法 |
| JP4733275B2 (ja) * | 2001-01-10 | 2011-07-27 | 三菱レイヨン株式会社 | （メタ）アクリル酸エステルの精製方法 |
| JP4942878B2 (ja) * | 2001-02-07 | 2012-05-30 | 三菱レイヨン株式会社 | （メタ）アクリル酸エステルの精製方法 |
| JP5083999B2 (ja) * | 2001-09-28 | 2012-11-28 | 旭化成ケミカルズ株式会社 | メタクリル酸メチルの製造法 |
| ZA200303241B (en) * | 2002-05-01 | 2003-11-04 | Rohm & Haas | Improved process for methacrylic acid and methcrylic acid ester production. |
| JP4573325B2 (ja) * | 2004-07-01 | 2010-11-04 | 三菱レイヨン株式会社 | メタクリル酸メチルの製造方法 |
| JP2007045803A (ja) * | 2005-08-12 | 2007-02-22 | Asahi Kasei Chemicals Corp | 精製されたメタクリル酸メチルを得る方法 |
| JP2007045795A (ja) * | 2005-08-12 | 2007-02-22 | Asahi Kasei Chemicals Corp | メタクリル酸メチルの精製方法 |
| JP2007063214A (ja) * | 2005-09-01 | 2007-03-15 | Asahi Kasei Chemicals Corp | メタクリル酸メチルの品質改良法 |
| DE102006058251A1 (de) * | 2006-12-08 | 2008-06-12 | Evonik Röhm Gmbh | Verfahren und Vorrichtung zur Herstellung von Methacrylsäurealkylestern |
| DE102006059511A1 (de) * | 2006-12-14 | 2008-06-19 | Evonik Röhm Gmbh | Verfahren zur Herstellung von Acetoncyanhydrin und dessen Folgeprodukten durch gezielte Kühlung |
| EP2635549B1 (en) * | 2010-11-04 | 2017-03-15 | Rohm and Haas Company | A process for producing methyl methacrylate having reduced biacetyl content |
| TWI433836B (zh) * | 2011-06-03 | 2014-04-11 | Rohm & Haas | 用於減少（甲基）丙烯酸酯純化期間之積垢之方法 |
| CN103242186B (zh) * | 2013-05-21 | 2015-02-18 | 重庆紫光化工股份有限公司 | 一种甲基丙烯酰胺和甲基丙烯酸甲酯的联合生产方法 |
| CN117355501A (zh) * | 2021-11-30 | 2024-01-05 | 三菱化学株式会社 | 含有甲基丙烯酸甲酯的组合物、含有甲基丙烯酸甲酯的组合物的保存方法和甲基丙烯酸甲酯聚合物的制造方法 |
| CN120092027A (zh) * | 2022-10-28 | 2025-06-03 | 三菱化学株式会社 | 单体组合物、甲基丙烯酸系树脂组合物及其制造方法以及树脂成型体 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS55130937A (en) * | 1979-03-29 | 1980-10-11 | Sekisui Chem Co Ltd | Preparation of ester |
| US4668818A (en) * | 1985-06-18 | 1987-05-26 | E. I. Du Pont De Nemours And Company | Methyl methacrylate production |
| JP2640495B2 (ja) * | 1988-05-25 | 1997-08-13 | 三菱レイヨン株式会社 | メタクリル酸メチルの精製法 |
| US5468899A (en) * | 1995-01-11 | 1995-11-21 | Bauer, Jr.; William | Process for purifying α,β-unsaturated esters |
-
1994
- 1994-06-30 FR FR9408103A patent/FR2721923B1/fr not_active Expired - Fee Related
-
1995
- 1995-06-05 US US08/464,223 patent/US5585514A/en not_active Expired - Fee Related
- 1995-06-17 TW TW084106224A patent/TW294660B/zh active
- 1995-06-19 ES ES95401430T patent/ES2113160T3/es not_active Expired - Lifetime
- 1995-06-19 DE DE69501437T patent/DE69501437T2/de not_active Expired - Fee Related
- 1995-06-19 DK DK95401430.4T patent/DK0690041T3/da active
- 1995-06-19 EP EP95401430A patent/EP0690041B1/fr not_active Expired - Lifetime
- 1995-06-19 AT AT95401430T patent/ATE162173T1/de not_active IP Right Cessation
- 1995-06-28 CA CA002152873A patent/CA2152873C/fr not_active Expired - Fee Related
- 1995-06-29 KR KR1019950018299A patent/KR0174109B1/ko not_active Expired - Fee Related
- 1995-06-30 CN CN95107747A patent/CN1125713A/zh active Pending
- 1995-06-30 JP JP7188337A patent/JP2783772B2/ja not_active Expired - Lifetime
- 1995-06-30 CZ CZ951733A patent/CZ173395A3/cs unknown
-
1998
- 1998-02-23 GR GR980400372T patent/GR3026194T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE69501437T2 (de) | 1998-06-04 |
| GR3026194T3 (en) | 1998-05-29 |
| JP2783772B2 (ja) | 1998-08-06 |
| CA2152873A1 (fr) | 1995-12-31 |
| DE69501437D1 (de) | 1998-02-19 |
| FR2721923B1 (fr) | 1996-08-14 |
| ATE162173T1 (de) | 1998-01-15 |
| ES2113160T3 (es) | 1998-04-16 |
| EP0690041A1 (fr) | 1996-01-03 |
| CZ173395A3 (en) | 1996-05-15 |
| DK0690041T3 (da) | 1998-02-09 |
| EP0690041B1 (fr) | 1998-01-14 |
| FR2721923A1 (fr) | 1996-01-05 |
| US5585514A (en) | 1996-12-17 |
| JPH08169862A (ja) | 1996-07-02 |
| KR0174109B1 (ko) | 1999-04-01 |
| TW294660B (OSRAM) | 1997-01-01 |
| KR960000851A (ko) | 1996-01-25 |
| CN1125713A (zh) | 1996-07-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |