JPS6215542B2 - - Google Patents
Info
- Publication number
- JPS6215542B2 JPS6215542B2 JP2302978A JP2302978A JPS6215542B2 JP S6215542 B2 JPS6215542 B2 JP S6215542B2 JP 2302978 A JP2302978 A JP 2302978A JP 2302978 A JP2302978 A JP 2302978A JP S6215542 B2 JPS6215542 B2 JP S6215542B2
- Authority
- JP
- Japan
- Prior art keywords
- methacrylic acid
- organic solvent
- alcohol
- esterification reaction
- acid
- 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
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 93
- 238000005886 esterification reaction Methods 0.000 claims description 45
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 39
- 238000000034 method Methods 0.000 claims description 36
- 238000000605 extraction Methods 0.000 claims description 35
- 239000003960 organic solvent Substances 0.000 claims description 22
- 239000002904 solvent Substances 0.000 claims description 22
- 239000007864 aqueous solution Substances 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- 230000032050 esterification Effects 0.000 claims description 15
- 238000004821 distillation Methods 0.000 claims description 14
- 125000005397 methacrylic acid ester group Chemical group 0.000 claims description 14
- 239000000243 solution Substances 0.000 claims description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 239000003377 acid catalyst Substances 0.000 claims description 10
- 238000009835 boiling Methods 0.000 claims description 10
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 8
- 238000007254 oxidation reaction Methods 0.000 claims description 7
- 230000003647 oxidation Effects 0.000 claims description 6
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 5
- STNJBCKSHOAVAJ-UHFFFAOYSA-N Methacrolein Chemical compound CC(=C)C=O STNJBCKSHOAVAJ-UHFFFAOYSA-N 0.000 claims description 4
- 230000003197 catalytic effect Effects 0.000 claims description 2
- 239000012046 mixed solvent Substances 0.000 claims description 2
- 239000012295 chemical reaction liquid Substances 0.000 claims 1
- 229910017053 inorganic salt Inorganic materials 0.000 claims 1
- 238000006116 polymerization reaction Methods 0.000 claims 1
- 239000012266 salt solution Substances 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 18
- 239000002994 raw material Substances 0.000 description 15
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 13
- 239000012071 phase Substances 0.000 description 13
- 238000000926 separation method Methods 0.000 description 13
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 12
- 239000008096 xylene Substances 0.000 description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 239000008346 aqueous phase Substances 0.000 description 7
- 238000009826 distribution Methods 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 230000007423 decrease Effects 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 238000005192 partition Methods 0.000 description 5
- 238000011084 recovery Methods 0.000 description 5
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 3
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 3
- 235000011130 ammonium sulphate Nutrition 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000002351 wastewater Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 2
- 238000010533 azeotropic distillation Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000010908 decantation Methods 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- -1 methacrylic acid Chemical class 0.000 description 2
- 238000003808 methanol extraction Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 235000002639 sodium chloride Nutrition 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 150000003738 xylenes Chemical class 0.000 description 2
- JHPBZFOKBAGZBL-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylprop-2-enoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)=C JHPBZFOKBAGZBL-UHFFFAOYSA-N 0.000 description 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- MWFMGBPGAXYFAR-UHFFFAOYSA-N 2-hydroxy-2-methylpropanenitrile Chemical compound CC(C)(O)C#N MWFMGBPGAXYFAR-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 229930007927 cymene Natural products 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000003134 recirculating effect Effects 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2302978A JPS54115318A (en) | 1978-02-28 | 1978-02-28 | Recovery of methacrylic acid |
| CA321,785A CA1131657A (en) | 1978-02-28 | 1979-02-19 | Recovery of methacrylic acid and alcohol in methacrylate production process |
| NL7901502A NL7901502A (nl) | 1978-02-28 | 1979-02-26 | Werkwijze voor het bereiden van een methacrylzuurester uit een verdunde oplossing van methacrylzuur in water. |
| GB7906677A GB2015509B (en) | 1978-02-28 | 1979-02-26 | Recovery of methacrylic acid and alcohol in methacrylate production process |
| DE19792907602 DE2907602A1 (de) | 1978-02-28 | 1979-02-27 | Verfahren zur herstellung von methacrylsaeureestern |
| IT48149/79A IT1114704B (it) | 1978-02-28 | 1979-02-27 | Procedimento per la preparazione di metacrilati ed il recupero di alcool ed acido metacrilio |
| FR7905153A FR2418216B1 (fr) | 1978-02-28 | 1979-02-28 | Procede perfectionne pour la synthese continue du methacrylate de methyle ou d'ethyle avec recuperation de l'acide methacrylique et de l'alcool non convertis |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2302978A JPS54115318A (en) | 1978-02-28 | 1978-02-28 | Recovery of methacrylic acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS54115318A JPS54115318A (en) | 1979-09-07 |
| JPS6215542B2 true JPS6215542B2 (ko) | 1987-04-08 |
Family
ID=12099037
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2302978A Granted JPS54115318A (en) | 1978-02-28 | 1978-02-28 | Recovery of methacrylic acid |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS54115318A (ko) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103796984B (zh) * | 2011-09-16 | 2016-03-23 | 赢创罗姆有限公司 | 甲基丙烯酸和甲基丙烯酸酯的制备方法 |
| MY165642A (en) * | 2011-09-16 | 2018-04-18 | Evonik Roehm Gmbh | Process for preparation of methacrylic acid and methacrylic acid ester |
| CN103827071A (zh) * | 2011-09-16 | 2014-05-28 | 赢创罗姆有限公司 | 甲基丙烯酸和甲基丙烯酸酯的制备方法 |
-
1978
- 1978-02-28 JP JP2302978A patent/JPS54115318A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS54115318A (en) | 1979-09-07 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CZ298267B6 (cs) | Zpusob prípravy kyseliny (meth)akrylové | |
| JP3211396B2 (ja) | アクリル酸及び酢酸の回収方法 | |
| JP3202150B2 (ja) | 酢酸の精製方法 | |
| US4250330A (en) | Process for the recovery of the solvent and of the by-produced methylacetate in the synthesis of terephthalic acid | |
| JP3232678B2 (ja) | 酢酸の回収方法 | |
| TWI383951B (zh) | 包含動作溶液之再生步驟的過氧化氫之製造方法 | |
| JP6602494B2 (ja) | （メタ）アクリル酸の連続回収方法および装置 | |
| TWI627161B (zh) | 甲基丙烯酸與甲基丙烯酸酯的製備方法 | |
| RU2237652C2 (ru) | Способ очистки | |
| JP4222815B2 (ja) | アクリル酸を回収するための抽出方法 | |
| JPH05246941A (ja) | アクリル酸製造においてアクリル酸を高純度に精製する方法 | |
| JP6592617B2 (ja) | （メタ）アクリル酸の連続回収方法および装置 | |
| JP3769505B2 (ja) | 主成分の酢酸およびギ酸からなる水性混合物を分離および精製するための方法 | |
| JP7337149B2 (ja) | ジオキソランを製造するための方法 | |
| JPS6215542B2 (ko) | ||
| JP2001322968A (ja) | メタクリル酸エステルの精製方法 | |
| JPS58183641A (ja) | （メタ）アクリル酸メチルの精製法 | |
| JP2019508477A (ja) | （メタ）アクリル酸の回収方法 | |
| JP4942878B2 (ja) | （メタ）アクリル酸エステルの精製方法 | |
| CA1131657A (en) | Recovery of methacrylic acid and alcohol in methacrylate production process | |
| JP3918528B2 (ja) | （メタ）アクリル酸の精製方法 | |
| JP3832868B2 (ja) | アクリル酸の精製法 | |
| JP2000281617A (ja) | アクリル酸の精製方法 | |
| JPS6236022B2 (ko) | ||
| JPS6299345A (ja) | アクリル酸エステル又はメタクリル酸エステルの回収法 |