JPH0333143B2 - - Google Patents
Info
- Publication number
- JPH0333143B2 JPH0333143B2 JP21216583A JP21216583A JPH0333143B2 JP H0333143 B2 JPH0333143 B2 JP H0333143B2 JP 21216583 A JP21216583 A JP 21216583A JP 21216583 A JP21216583 A JP 21216583A JP H0333143 B2 JPH0333143 B2 JP H0333143B2
- Authority
- JP
- Japan
- Prior art keywords
- methacrylic acid
- boiling point
- column
- line
- 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 62
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 54
- 238000009835 boiling Methods 0.000 claims description 40
- STNJBCKSHOAVAJ-UHFFFAOYSA-N Methacrolein Chemical compound CC(=C)C=O STNJBCKSHOAVAJ-UHFFFAOYSA-N 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 17
- 239000007795 chemical reaction product Substances 0.000 claims description 12
- 238000001816 cooling Methods 0.000 claims description 12
- 239000000284 extract Substances 0.000 claims description 10
- 238000007254 oxidation reaction Methods 0.000 claims description 10
- 230000003647 oxidation Effects 0.000 claims description 8
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 6
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- 125000002723 alicyclic group Chemical group 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 5
- 239000006227 byproduct Substances 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 5
- 150000002576 ketones Chemical class 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- 239000007789 gas Substances 0.000 description 24
- 238000000605 extraction Methods 0.000 description 23
- 239000002904 solvent Substances 0.000 description 20
- 239000012535 impurity Substances 0.000 description 14
- 238000000746 purification Methods 0.000 description 10
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 8
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 8
- 239000011976 maleic acid Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- -1 aromatic carboxylic acids Chemical class 0.000 description 5
- 150000002170 ethers Chemical class 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 238000010791 quenching Methods 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000005587 bubbling Effects 0.000 description 2
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 2
- 229940018557 citraconic acid Drugs 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 2
- 229940011051 isopropyl acetate Drugs 0.000 description 2
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000004065 wastewater treatment Methods 0.000 description 2
- 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
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000011964 heteropoly acid Substances 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 239000012495 reaction gas Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/48—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP21216583A JPS60104034A (ja) | 1983-11-11 | 1983-11-11 | メタクリル酸の回収法 |
| FR8417140A FR2560187B1 (fr) | 1983-11-11 | 1984-11-09 | Procede de recuperation de l'acide methacrylique |
| DE19843441207 DE3441207A1 (de) | 1983-11-11 | 1984-11-10 | Verfahren zur gewinnung von methacrylsaeure |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP21216583A JPS60104034A (ja) | 1983-11-11 | 1983-11-11 | メタクリル酸の回収法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60104034A JPS60104034A (ja) | 1985-06-08 |
| JPH0333143B2 true JPH0333143B2 (enrdf_load_stackoverflow) | 1991-05-16 |
Family
ID=16617974
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP21216583A Granted JPS60104034A (ja) | 1983-11-11 | 1983-11-11 | メタクリル酸の回収法 |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JPS60104034A (enrdf_load_stackoverflow) |
| DE (1) | DE3441207A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2560187B1 (enrdf_load_stackoverflow) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0694432B2 (ja) * | 1985-10-31 | 1994-11-24 | 三井東圧化学株式会社 | メタクリル酸水溶液の精製法 |
| JPH0739367B2 (ja) * | 1985-10-31 | 1995-05-01 | 三井東圧化学株式会社 | メタクリル酸の回収法 |
| JPH0694433B2 (ja) * | 1985-11-20 | 1994-11-24 | 三井東圧化学株式会社 | メタクリル酸の精製法 |
| US5877345A (en) * | 1997-02-07 | 1999-03-02 | Rohm And Haas Company | Process for producing butyl acrylate |
| JP4814484B2 (ja) * | 2003-10-06 | 2011-11-16 | ヤンマー株式会社 | 枝豆引抜収穫機 |
| JP2009263351A (ja) * | 2008-03-31 | 2009-11-12 | Mitsubishi Chemicals Corp | （メタ）アクリル酸の製造方法 |
| WO2023063525A1 (ko) * | 2021-10-15 | 2023-04-20 | 주식회사 엘지화학 | 아크릴산 제조방법 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS54119412A (en) * | 1978-03-06 | 1979-09-17 | Mitsubishi Chem Ind Ltd | Purification of methacrylic acid |
| NL8001385A (nl) * | 1979-03-15 | 1980-09-17 | Halcon Res & Dev | Werkwijze voor de bereiding van methacrylzuur. |
| JPS6016927B2 (ja) | 1979-07-19 | 1985-04-30 | 三菱レイヨン株式会社 | メタクリル酸の抽出分離法 |
| JPS5679634A (en) * | 1979-12-05 | 1981-06-30 | Japan Synthetic Rubber Co Ltd | Separation of methacrylic acid |
| JPS5852239A (ja) * | 1981-09-22 | 1983-03-28 | Nippon Kayaku Co Ltd | 酸化反応生成ガスの処理法 |
| JPS5899434A (ja) * | 1981-12-10 | 1983-06-13 | Nippon Shokubai Kagaku Kogyo Co Ltd | メタクリル酸の精製方法 |
-
1983
- 1983-11-11 JP JP21216583A patent/JPS60104034A/ja active Granted
-
1984
- 1984-11-09 FR FR8417140A patent/FR2560187B1/fr not_active Expired
- 1984-11-10 DE DE19843441207 patent/DE3441207A1/de not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60104034A (ja) | 1985-06-08 |
| FR2560187A1 (fr) | 1985-08-30 |
| DE3441207A1 (de) | 1985-05-30 |
| FR2560187B1 (fr) | 1987-11-13 |
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