CN1125713A - 不含丁二酮的甲基丙烯酸甲酯的制备方法 - Google Patents
不含丁二酮的甲基丙烯酸甲酯的制备方法 Download PDFInfo
- Publication number
- CN1125713A CN1125713A CN95107747A CN95107747A CN1125713A CN 1125713 A CN1125713 A CN 1125713A CN 95107747 A CN95107747 A CN 95107747A CN 95107747 A CN95107747 A CN 95107747A CN 1125713 A CN1125713 A CN 1125713A
- Authority
- CN
- China
- Prior art keywords
- methyl methacrylate
- diamines
- aromatics
- arbitrary
- distillation
- 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
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 title claims abstract description 48
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical compound CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 title claims abstract description 41
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- 238000000034 method Methods 0.000 claims abstract description 28
- 238000004821 distillation Methods 0.000 claims abstract description 19
- 239000012535 impurity Substances 0.000 claims abstract description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 13
- 150000004985 diamines Chemical class 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 claims description 4
- 238000005194 fractionation Methods 0.000 claims description 4
- MWFMGBPGAXYFAR-UHFFFAOYSA-N 2-hydroxy-2-methylpropanenitrile Chemical compound CC(C)(O)C#N MWFMGBPGAXYFAR-UHFFFAOYSA-N 0.000 claims description 3
- NSOXQYCFHDMMGV-UHFFFAOYSA-N Tetrakis(2-hydroxypropyl)ethylenediamine Chemical compound CC(O)CN(CC(C)O)CCN(CC(C)O)CC(C)O NSOXQYCFHDMMGV-UHFFFAOYSA-N 0.000 claims description 3
- 238000007171 acid catalysis Methods 0.000 claims description 3
- 238000009835 boiling Methods 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
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 claims description 2
- 229910052921 ammonium sulfate Inorganic materials 0.000 claims description 2
- 235000011130 ammonium sulphate Nutrition 0.000 claims description 2
- 238000000622 liquid--liquid extraction Methods 0.000 claims description 2
- 238000000638 solvent extraction Methods 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 claims 2
- 239000011541 reaction mixture Substances 0.000 abstract description 3
- 239000000178 monomer Substances 0.000 abstract description 2
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 238000000746 purification Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 description 6
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 4
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 4
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical group C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- 206010023126 Jaundice Diseases 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 239000000126 substance Substances 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 |
|---|---|---|---|
| FR9408103A FR2721923B1 (fr) | 1994-06-30 | 1994-06-30 | Procede de fabrication de methacrylate de methyle sans diacetyle |
| FR9408103 | 1994-06-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1125713A true CN1125713A (zh) | 1996-07-03 |
Family
ID=9464864
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN95107747A Pending CN1125713A (zh) | 1994-06-30 | 1995-06-30 | 不含丁二酮的甲基丙烯酸甲酯的制备方法 |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US5585514A (enExample) |
| EP (1) | EP0690041B1 (enExample) |
| JP (1) | JP2783772B2 (enExample) |
| KR (1) | KR0174109B1 (enExample) |
| CN (1) | CN1125713A (enExample) |
| AT (1) | ATE162173T1 (enExample) |
| CA (1) | CA2152873C (enExample) |
| CZ (1) | CZ173395A3 (enExample) |
| DE (1) | DE69501437T2 (enExample) |
| DK (1) | DK0690041T3 (enExample) |
| ES (1) | ES2113160T3 (enExample) |
| FR (1) | FR2721923B1 (enExample) |
| GR (1) | GR3026194T3 (enExample) |
| TW (1) | TW294660B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103596916A (zh) * | 2011-06-03 | 2014-02-19 | 罗门哈斯公司 | 减少(甲基)丙烯酸酯纯化期间结垢的方法 |
Families Citing this family (15)
| 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 |
| 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 |
| 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 |
| 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 |
| MX2013005049A (es) * | 2010-11-04 | 2013-06-28 | Rohm And Haas Comapny | Un proceso para producir metacrilato de metilo teniendo contenido de biacetilo. |
| 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 |
| WO2023100867A1 (ja) * | 2021-11-30 | 2023-06-08 | 三菱ケミカル株式会社 | メタクリル酸メチル含有組成物、メタクリル酸メチル含有組成物の保存方法及びメタクリル酸メチル重合体の製造方法 |
| JPWO2024090576A1 (enExample) * | 2022-10-28 | 2024-05-02 |
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 DE DE69501437T patent/DE69501437T2/de not_active Expired - Fee Related
- 1995-06-19 DK DK95401430.4T patent/DK0690041T3/da active
- 1995-06-19 AT AT95401430T patent/ATE162173T1/de not_active IP Right Cessation
- 1995-06-19 ES ES95401430T patent/ES2113160T3/es not_active Expired - Lifetime
- 1995-06-19 EP EP95401430A patent/EP0690041B1/fr not_active Expired - Lifetime
- 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
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103596916A (zh) * | 2011-06-03 | 2014-02-19 | 罗门哈斯公司 | 减少(甲基)丙烯酸酯纯化期间结垢的方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2721923B1 (fr) | 1996-08-14 |
| DE69501437T2 (de) | 1998-06-04 |
| CA2152873C (fr) | 1998-10-27 |
| ATE162173T1 (de) | 1998-01-15 |
| DE69501437D1 (de) | 1998-02-19 |
| JP2783772B2 (ja) | 1998-08-06 |
| CZ173395A3 (en) | 1996-05-15 |
| EP0690041B1 (fr) | 1998-01-14 |
| ES2113160T3 (es) | 1998-04-16 |
| KR0174109B1 (ko) | 1999-04-01 |
| FR2721923A1 (fr) | 1996-01-05 |
| GR3026194T3 (en) | 1998-05-29 |
| TW294660B (enExample) | 1997-01-01 |
| DK0690041T3 (da) | 1998-02-09 |
| JPH08169862A (ja) | 1996-07-02 |
| US5585514A (en) | 1996-12-17 |
| EP0690041A1 (fr) | 1996-01-03 |
| CA2152873A1 (fr) | 1995-12-31 |
| KR960000851A (ko) | 1996-01-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C06 | Publication | ||
| PB01 | Publication | ||
| C01 | Deemed withdrawal of patent application (patent law 1993) | ||
| WD01 | Invention patent application deemed withdrawn after publication |