JPS6312458B2 - - Google Patents
Info
- Publication number
- JPS6312458B2 JPS6312458B2 JP56029940A JP2994081A JPS6312458B2 JP S6312458 B2 JPS6312458 B2 JP S6312458B2 JP 56029940 A JP56029940 A JP 56029940A JP 2994081 A JP2994081 A JP 2994081A JP S6312458 B2 JPS6312458 B2 JP S6312458B2
- Authority
- JP
- Japan
- Prior art keywords
- methacrolein
- acetic acid
- methacrylic acid
- gas
- conduit
- 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
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 305
- STNJBCKSHOAVAJ-UHFFFAOYSA-N Methacrolein Chemical compound CC(=C)C=O STNJBCKSHOAVAJ-UHFFFAOYSA-N 0.000 claims description 95
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 76
- 239000007789 gas Substances 0.000 claims description 58
- 238000000034 method Methods 0.000 claims description 56
- 238000007254 oxidation reaction Methods 0.000 claims description 54
- 239000007864 aqueous solution Substances 0.000 claims description 42
- 238000010791 quenching Methods 0.000 claims description 31
- 230000000171 quenching effect Effects 0.000 claims description 30
- 230000003647 oxidation Effects 0.000 claims description 29
- 238000011084 recovery Methods 0.000 claims description 29
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 27
- 239000007795 chemical reaction product Substances 0.000 claims description 15
- 239000002994 raw material Substances 0.000 claims description 15
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 claims description 14
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 14
- 239000006227 byproduct Substances 0.000 claims description 14
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 claims description 14
- 238000004519 manufacturing process Methods 0.000 claims description 13
- 238000009835 boiling Methods 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 7
- 230000003197 catalytic effect Effects 0.000 claims description 6
- 238000001816 cooling Methods 0.000 claims description 6
- 239000000047 product Substances 0.000 claims description 6
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 4
- 229910001882 dioxygen Inorganic materials 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 229960000583 acetic acid Drugs 0.000 description 99
- 238000000605 extraction Methods 0.000 description 49
- 238000010521 absorption reaction Methods 0.000 description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
- 239000007788 liquid Substances 0.000 description 24
- 239000003054 catalyst Substances 0.000 description 19
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 239000008096 xylene Substances 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 7
- 238000000926 separation method Methods 0.000 description 6
- 239000000463 material Substances 0.000 description 5
- 239000002351 wastewater Substances 0.000 description 5
- 230000000813 microbial effect Effects 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- 238000000638 solvent extraction Methods 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 229910052750 molybdenum Inorganic materials 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 239000005416 organic matter Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 239000002250 absorbent Substances 0.000 description 2
- 230000002745 absorbent Effects 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 238000010533 azeotropic distillation Methods 0.000 description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 description 2
- 238000003889 chemical engineering Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000007710 freezing Methods 0.000 description 2
- 230000008014 freezing Effects 0.000 description 2
- 230000005484 gravity Effects 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- WHRZCXAVMTUTDD-UHFFFAOYSA-N 1h-furo[2,3-d]pyrimidin-2-one Chemical compound N1C(=O)N=C2OC=CC2=C1 WHRZCXAVMTUTDD-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 235000006173 Larrea tridentata Nutrition 0.000 description 1
- 244000073231 Larrea tridentata Species 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 150000001334 alicyclic compounds Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000007809 chemical reaction catalyst Substances 0.000 description 1
- 238000009841 combustion method Methods 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 229960002126 creosote Drugs 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000000295 fuel oil Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- -1 isobutylene Chemical class 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 238000004065 wastewater treatment Methods 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
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
- C07C51/25—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of unsaturated compounds containing no six-membered aromatic ring
- C07C51/252—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of unsaturated compounds containing no six-membered aromatic ring of propene, butenes, acrolein or methacrolein
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
- C07C45/33—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties
- C07C45/34—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties in unsaturated compounds
- C07C45/35—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties in unsaturated compounds in propene or isobutene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
- C07C45/37—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of >C—O—functional groups to >C=O groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
- C07C51/23—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of oxygen-containing groups to carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
- C07C51/23—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of oxygen-containing groups to carboxyl groups
- C07C51/235—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of oxygen-containing groups to carboxyl groups of —CHO groups or primary alcohol groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/377—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2994081A JPS57144237A (en) | 1981-03-04 | 1981-03-04 | Preparation of methacrylic acid |
| GB8206428A GB2096601B (en) | 1981-03-04 | 1982-03-04 | Process for producing methacrylic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2994081A JPS57144237A (en) | 1981-03-04 | 1981-03-04 | Preparation of methacrylic acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57144237A JPS57144237A (en) | 1982-09-06 |
| JPS6312458B2 true JPS6312458B2 (xx) | 1988-03-18 |
Family
ID=12289981
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2994081A Granted JPS57144237A (en) | 1981-03-04 | 1981-03-04 | Preparation of methacrylic acid |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JPS57144237A (xx) |
| GB (1) | GB2096601B (xx) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01142357U (xx) * | 1988-03-25 | 1989-09-29 |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1308737C (en) * | 1987-04-16 | 1992-10-13 | Syoichi Matsumoto | Process for producing methacrylic ester |
| DE19814421A1 (de) * | 1998-03-31 | 1999-10-07 | Basf Ag | Verfahren zur Herstellung von Acrylsäure und Acrylsäureestern |
| JP5691252B2 (ja) * | 2010-06-10 | 2015-04-01 | 三菱レイヨン株式会社 | メタクリル酸製造用ヘテロポリ酸系触媒の製造方法、及びメタクリル酸の製造方法 |
| 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 |
| JP6611391B1 (ja) * | 2018-11-14 | 2019-11-27 | 住友化学株式会社 | メタクリル酸の製造装置 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS51103664A (en) * | 1975-03-10 | 1976-09-13 | Nippon Catalytic Chem Ind | Haisuino ryohoho |
| JPS5353613A (en) * | 1976-10-26 | 1978-05-16 | Nippon Zeon Co Ltd | Preparation of methacrylic acid |
| JPS5448706A (en) * | 1977-09-06 | 1979-04-17 | Halcon Res & Dev | Method of recovering methacrolein from isobutylene contact oxidation reaction gas mixture |
| JPS5821896A (ja) * | 1981-07-31 | 1983-02-08 | ソニー株式会社 | 電子部品の実装方法 |
-
1981
- 1981-03-04 JP JP2994081A patent/JPS57144237A/ja active Granted
-
1982
- 1982-03-04 GB GB8206428A patent/GB2096601B/en not_active Expired
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS51103664A (en) * | 1975-03-10 | 1976-09-13 | Nippon Catalytic Chem Ind | Haisuino ryohoho |
| JPS5353613A (en) * | 1976-10-26 | 1978-05-16 | Nippon Zeon Co Ltd | Preparation of methacrylic acid |
| JPS5448706A (en) * | 1977-09-06 | 1979-04-17 | Halcon Res & Dev | Method of recovering methacrolein from isobutylene contact oxidation reaction gas mixture |
| JPS5821896A (ja) * | 1981-07-31 | 1983-02-08 | ソニー株式会社 | 電子部品の実装方法 |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01142357U (xx) * | 1988-03-25 | 1989-09-29 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS57144237A (en) | 1982-09-06 |
| GB2096601B (en) | 1985-03-20 |
| GB2096601A (en) | 1982-10-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP4732366B2 (ja) | （メタ）アクリル酸の製造法 | |
| JP5358582B2 (ja) | （メタ）アクリル酸回収方法および（メタ）アクリル酸回収装置 | |
| US4618709A (en) | Waste water treatment in the production of methacrylic acid | |
| US6639106B1 (en) | Process for preparing and purifying acrylic acid from propylene having improved capacity | |
| JP2000290221A (ja) | （メタ）アクリル酸の精製方法 | |
| JP2007518736A (ja) | オレフィン性不飽和ニトリル類の精製方法 | |
| EP1716095B1 (en) | Method for producing (meth)acrylic acid | |
| JP4222815B2 (ja) | アクリル酸を回収するための抽出方法 | |
| JPH0276835A (ja) | メタクロレインの回収方法 | |
| KR101052710B1 (ko) | 기체 기재의 산화에 의해 얻어진 (메트)아크릴산의정제방법 | |
| JPS6312458B2 (xx) | ||
| JPS6310691B2 (xx) | ||
| JP4091766B2 (ja) | メタクロレインの製造方法 | |
| JPS6056127B2 (ja) | 酢酸の回収法 | |
| JPH062700B2 (ja) | メタクロレインの分離法 | |
| JPS6160061B2 (xx) | ||
| JPS6296447A (ja) | メタクリル酸の回収方法 | |
| JPH0834757A (ja) | アクリル酸の精製法 | |
| JPH0372209B2 (xx) | ||
| JPH03176439A (ja) | イソブタンおよびメタクロレインの回収方法 | |
| JPS5993028A (ja) | メタクリル酸の回収方法 | |
| JPH03176438A (ja) | イソブタンおよびメタクロレインの回収方法 | |
| JPH03190831A (ja) | イソブタンおよびメタクロレインの回収法 | |
| JPH0859543A (ja) | アクリル酸の分離方法 | |
| JPH0615496B2 (ja) | アクリル酸の製造方法 |