CA1061355A - Process for producing glycidyl methacrylate - Google Patents
Process for producing glycidyl methacrylateInfo
- Publication number
- CA1061355A CA1061355A CA226,929A CA226929A CA1061355A CA 1061355 A CA1061355 A CA 1061355A CA 226929 A CA226929 A CA 226929A CA 1061355 A CA1061355 A CA 1061355A
- Authority
- CA
- Canada
- Prior art keywords
- alkali metal
- process according
- transesterification
- glycide
- glycidyl methacrylate
- 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
Links
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 title claims abstract description 17
- 238000000034 method Methods 0.000 title claims abstract description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 31
- 238000006243 chemical reaction Methods 0.000 claims abstract description 21
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims abstract description 20
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000003054 catalyst Substances 0.000 claims abstract description 16
- 238000005809 transesterification reaction Methods 0.000 claims abstract description 14
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 9
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 7
- 238000006116 polymerization reaction Methods 0.000 claims description 10
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 6
- 239000003112 inhibitor Substances 0.000 claims description 6
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 claims description 5
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical group [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 3
- -1 alkali metal salt Chemical class 0.000 claims description 3
- 238000004821 distillation Methods 0.000 claims description 3
- 229910052744 lithium Inorganic materials 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 2
- 229910000102 alkali metal hydride Inorganic materials 0.000 claims description 2
- 150000008046 alkali metal hydrides Chemical class 0.000 claims description 2
- 150000004982 aromatic amines Chemical class 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Natural products CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 150000001339 alkali metal compounds Chemical class 0.000 abstract description 3
- 229940102838 methylmethacrylate Drugs 0.000 description 17
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- JILPJDVXYVTZDQ-UHFFFAOYSA-N lithium methoxide Chemical compound [Li+].[O-]C JILPJDVXYVTZDQ-UHFFFAOYSA-N 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 239000004922 lacquer Substances 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M potassium chloride Inorganic materials [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- 235000011164 potassium chloride Nutrition 0.000 description 2
- 239000001103 potassium chloride Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 101100367084 Caenorhabditis elegans such-1 gene Proteins 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 239000003570 air Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229940035422 diphenylamine Drugs 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000011552 falling film Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910000103 lithium hydride Inorganic materials 0.000 description 1
- CRGZYKWWYNQGEC-UHFFFAOYSA-N magnesium;methanolate Chemical compound [Mg+2].[O-]C.[O-]C CRGZYKWWYNQGEC-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229960003505 mequinol Drugs 0.000 description 1
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- SONHXMAHPHADTF-UHFFFAOYSA-M sodium;2-methylprop-2-enoate Chemical compound [Na+].CC(=C)C([O-])=O SONHXMAHPHADTF-UHFFFAOYSA-M 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/16—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by esterified hydroxyl radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Epoxy Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742423405 DE2423405C3 (de) | 1974-05-14 | 1974-05-14 | Verfahren zur Herstellung von Glycidylmethacrylat |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1061355A true CA1061355A (en) | 1979-08-28 |
Family
ID=5915531
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA226,929A Expired CA1061355A (en) | 1974-05-14 | 1975-05-14 | Process for producing glycidyl methacrylate |
Country Status (12)
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL7605330A (nl) * | 1975-06-05 | 1976-12-07 | Degussa | Werkwijze voor het bereiden van glycidylmetha- crylaat. |
| JPS543007A (en) | 1977-06-06 | 1979-01-11 | Nippon Oil & Fats Co Ltd | Preparation of glycidyl (meth)acrylate |
| JPS5793930A (en) * | 1980-12-03 | 1982-06-11 | Mitsui Toatsu Chem Inc | Preparation of methacrylic ester |
| DE3140764A1 (de) | 1981-10-14 | 1983-04-28 | Röhm GmbH, 6100 Darmstadt | Verfahren zur herstellung der ester vopn carbonsaeuren mit epoxigruppenhaltigen alkoholen |
| DE3423441A1 (de) * | 1984-06-26 | 1986-01-02 | Röhm GmbH, 6100 Darmstadt | Verfahren zur herstellung von estern der acryl- und methacrylsaeure durch umesterung |
| US4780555A (en) * | 1988-01-04 | 1988-10-25 | Dow Corning Corporation | Method for preparing and stabilizing acryl-functional halosilanes |
| DE102009057699A1 (de) | 2009-12-07 | 2011-06-09 | Kruk, Sandra | Bodenteil für einen Solar-Flachkollektor, Verfahren zu seiner Herstellung und mit dem Bodenteil ausgerüsteter Solar-Flachkollektor |
| JP5606132B2 (ja) * | 2010-04-12 | 2014-10-15 | 三菱レイヨン株式会社 | （メタ）アクリル酸エステルの製造方法 |
| CN112625007B (zh) * | 2019-10-09 | 2023-05-26 | 佳化化学(上海)有限公司 | 一种制备甲基丙烯酸缩水甘油酯的方法 |
| CN116535367A (zh) * | 2023-04-17 | 2023-08-04 | 湖北荆洪生物科技股份有限公司 | 一种制备甲基丙烯酸缩水甘油酯的方法 |
-
1974
- 1974-05-14 DE DE19742423405 patent/DE2423405C3/de not_active Expired
-
1975
- 1975-04-11 SU SU752121916A patent/SU942595A3/ru active
- 1975-04-15 IT IT6795375A patent/IT1032669B/it active
- 1975-04-24 GB GB1700975A patent/GB1441085A/en not_active Expired
- 1975-04-28 NL NL7505019A patent/NL7505019A/xx not_active Application Discontinuation
- 1975-05-05 CH CH577375A patent/CH599949A5/xx not_active IP Right Cessation
- 1975-05-12 DD DD18596475A patent/DD118413A5/xx unknown
- 1975-05-13 BE BE6045011A patent/BE829033A/xx not_active IP Right Cessation
- 1975-05-13 JP JP5553275A patent/JPS6137268B2/ja not_active Expired
- 1975-05-13 AT AT364975A patent/AT341538B/de not_active IP Right Cessation
- 1975-05-14 FR FR7515043A patent/FR2271222B1/fr not_active Expired
- 1975-05-14 CA CA226,929A patent/CA1061355A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2271222A1 (enrdf_load_stackoverflow) | 1975-12-12 |
| JPS6137268B2 (enrdf_load_stackoverflow) | 1986-08-22 |
| DE2423405B2 (de) | 1978-03-23 |
| IT1032669B (it) | 1979-06-20 |
| GB1441085A (en) | 1976-06-30 |
| SU942595A3 (ru) | 1982-07-07 |
| BE829033A (fr) | 1975-11-13 |
| ATA364975A (de) | 1977-06-15 |
| FR2271222B1 (enrdf_load_stackoverflow) | 1977-07-08 |
| DE2423405A1 (de) | 1975-11-27 |
| DD118413A5 (enrdf_load_stackoverflow) | 1976-03-05 |
| DE2423405C3 (de) | 1983-05-19 |
| JPS50154205A (enrdf_load_stackoverflow) | 1975-12-12 |
| AT341538B (de) | 1978-02-10 |
| NL7505019A (nl) | 1975-11-18 |
| CH599949A5 (enrdf_load_stackoverflow) | 1978-06-15 |
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