JPS6348857B2 - - Google Patents
Info
- Publication number
- JPS6348857B2 JPS6348857B2 JP55033325A JP3332580A JPS6348857B2 JP S6348857 B2 JPS6348857 B2 JP S6348857B2 JP 55033325 A JP55033325 A JP 55033325A JP 3332580 A JP3332580 A JP 3332580A JP S6348857 B2 JPS6348857 B2 JP S6348857B2
- Authority
- JP
- Japan
- Prior art keywords
- methacrylic acid
- solvent
- methacrolein
- water
- effluent
- 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 165
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 129
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 104
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 72
- 238000000605 extraction Methods 0.000 claims description 55
- STNJBCKSHOAVAJ-UHFFFAOYSA-N Methacrolein Chemical compound CC(=C)C=O STNJBCKSHOAVAJ-UHFFFAOYSA-N 0.000 claims description 49
- 238000000034 method Methods 0.000 claims description 43
- 238000007254 oxidation reaction Methods 0.000 claims description 40
- 230000003647 oxidation Effects 0.000 claims description 39
- 239000007789 gas Substances 0.000 claims description 29
- 239000007788 liquid Substances 0.000 claims description 25
- 239000000203 mixture Substances 0.000 claims description 25
- 238000001816 cooling Methods 0.000 claims description 23
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 16
- 239000012046 mixed solvent Substances 0.000 claims description 11
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 10
- 239000012071 phase Substances 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- HCFAJYNVAYBARA-UHFFFAOYSA-N 4-heptanone Chemical compound CCCC(=O)CCC HCFAJYNVAYBARA-UHFFFAOYSA-N 0.000 claims description 6
- 239000007791 liquid phase Substances 0.000 claims description 6
- 238000010791 quenching Methods 0.000 claims description 6
- 239000011261 inert gas Substances 0.000 claims description 5
- 230000000171 quenching effect Effects 0.000 claims description 5
- 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
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 3
- 230000003197 catalytic effect Effects 0.000 claims description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 239000012808 vapor phase Substances 0.000 claims 1
- 239000002904 solvent Substances 0.000 description 85
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 54
- 238000011084 recovery Methods 0.000 description 32
- 238000004821 distillation Methods 0.000 description 30
- 229920000642 polymer Polymers 0.000 description 25
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 16
- 239000012535 impurity Substances 0.000 description 16
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 15
- 239000008346 aqueous phase Substances 0.000 description 15
- 239000007787 solid Substances 0.000 description 14
- 239000006227 byproduct Substances 0.000 description 12
- 150000002576 ketones Chemical class 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 238000000926 separation method Methods 0.000 description 12
- 239000011877 solvent mixture Substances 0.000 description 12
- 239000003054 catalyst Substances 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 6
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 6
- 150000001491 aromatic compounds Chemical class 0.000 description 6
- 238000010586 diagram Methods 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 238000005192 partition Methods 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 6
- 239000002243 precursor Substances 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000010926 purge Methods 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- 239000000110 cooling liquid Substances 0.000 description 4
- 230000002349 favourable effect Effects 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 238000000638 solvent extraction Methods 0.000 description 4
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical class [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 3
- 238000010533 azeotropic distillation Methods 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229910002090 carbon oxide Inorganic materials 0.000 description 3
- 230000018044 dehydration Effects 0.000 description 3
- 238000006297 dehydration reaction Methods 0.000 description 3
- 150000002815 nickel Chemical class 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 230000001590 oxidative effect Effects 0.000 description 3
- 239000002685 polymerization catalyst Substances 0.000 description 3
- 238000005201 scrubbing Methods 0.000 description 3
- HXVNBWAKAOHACI-UHFFFAOYSA-N 2,4-dimethyl-3-pentanone Chemical compound CC(C)C(=O)C(C)C HXVNBWAKAOHACI-UHFFFAOYSA-N 0.000 description 2
- BWLBGMIXKSTLSX-UHFFFAOYSA-N 2-hydroxyisobutyric acid Chemical compound CC(C)(O)C(O)=O BWLBGMIXKSTLSX-UHFFFAOYSA-N 0.000 description 2
- HYTRYEXINDDXJK-UHFFFAOYSA-N Ethyl isopropyl ketone Chemical compound CCC(=O)C(C)C HYTRYEXINDDXJK-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- NGEWQZIDQIYUNV-UHFFFAOYSA-N L-valinic acid Natural products CC(C)C(O)C(O)=O NGEWQZIDQIYUNV-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- -1 aliphatic alcohols Chemical class 0.000 description 2
- 239000010953 base metal Substances 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- WFPZPJSADLPSON-UHFFFAOYSA-N dinitrogen tetraoxide Chemical compound [O-][N+](=O)[N+]([O-])=O WFPZPJSADLPSON-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 239000012263 liquid product Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 125000005395 methacrylic acid group Chemical group 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- CHQZVBKYAOZKMB-UHFFFAOYSA-N 2-methylprop-2-enoic acid;hydrate Chemical compound O.CC(=C)C(O)=O CHQZVBKYAOZKMB-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 229920002845 Poly(methacrylic acid) Polymers 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000001174 ascending effect Effects 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000000998 batch distillation Methods 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000895 extractive distillation Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000008246 gaseous mixture Substances 0.000 description 1
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- DCUFMVPCXCSVNP-UHFFFAOYSA-N methacrylic anhydride Chemical compound CC(=C)C(=O)OC(=O)C(C)=C DCUFMVPCXCSVNP-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 238000011027 product recovery Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000011144 upstream manufacturing 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
- C07C51/42—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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US2056379A | 1979-03-15 | 1979-03-15 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS55127339A JPS55127339A (en) | 1980-10-02 |
| JPS6348857B2 true JPS6348857B2 (US06277897-20010821-C00009.png) | 1988-09-30 |
Family
ID=21799306
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3332580A Granted JPS55127339A (en) | 1979-03-15 | 1980-03-15 | Recovery of methacrylic acid |
Country Status (9)
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60104034A (ja) * | 1983-11-11 | 1985-06-08 | Nippon Kayaku Co Ltd | メタクリル酸の回収法 |
| US4554054A (en) * | 1983-12-09 | 1985-11-19 | Rohm And Haas Company | Methacrylic acid separation |
| DE3721865A1 (de) * | 1987-07-02 | 1989-01-12 | Basf Ag | Verfahren zur herstellung von methacrylsaeure |
| DE19709471A1 (de) * | 1997-03-07 | 1998-09-10 | Basf Ag | Verfahren zur Herstellung von (Meth)acrylsäure |
| JP4056429B2 (ja) | 2003-06-05 | 2008-03-05 | 株式会社日本触媒 | （メタ）アクリル酸の製造方法 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4828414A (US06277897-20010821-C00009.png) * | 1971-08-13 | 1973-04-14 | ||
| JPS495915A (US06277897-20010821-C00009.png) * | 1972-05-23 | 1974-01-19 | ||
| JPS5371011A (en) * | 1976-12-07 | 1978-06-24 | Sumitomo Chem Co Ltd | Extraction of methacrylic acid |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1350736A (en) * | 1971-02-15 | 1974-04-24 | Sumitomo Chemical Co | Process for production of acrylic acid and methacrylic acid |
| JPS4862712A (US06277897-20010821-C00009.png) * | 1971-12-07 | 1973-09-01 | ||
| FR2165108A5 (en) * | 1971-12-17 | 1973-08-03 | Sumitomo Chemical Co | Extraction of acrylic and/or methacrylic acid - from soln, using a methylethyl ketone/benzene extractant mixture |
| JPS5148609A (ja) * | 1974-10-23 | 1976-04-26 | Asahi Glass Co Ltd | Nidansankanyoruisopuchirenkarano metaku |
-
1980
- 1980-03-07 NL NL8001385A patent/NL8001385A/nl not_active Application Discontinuation
- 1980-03-14 BE BE0/199798A patent/BE882229A/fr not_active IP Right Cessation
- 1980-03-14 BR BR8001520A patent/BR8001520A/pt unknown
- 1980-03-14 AR AR280322A patent/AR223209A1/es active
- 1980-03-14 GB GB8008694A patent/GB2045759B/en not_active Expired
- 1980-03-14 FR FR8005797A patent/FR2451360A1/fr not_active Withdrawn
- 1980-03-14 DE DE3009946A patent/DE3009946C2/de not_active Expired
- 1980-03-14 IT IT48160/80A patent/IT1147076B/it active
- 1980-03-15 JP JP3332580A patent/JPS55127339A/ja active Granted
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4828414A (US06277897-20010821-C00009.png) * | 1971-08-13 | 1973-04-14 | ||
| JPS495915A (US06277897-20010821-C00009.png) * | 1972-05-23 | 1974-01-19 | ||
| JPS5371011A (en) * | 1976-12-07 | 1978-06-24 | Sumitomo Chem Co Ltd | Extraction of methacrylic acid |
Also Published As
| Publication number | Publication date |
|---|---|
| BR8001520A (pt) | 1980-11-11 |
| IT1147076B (it) | 1986-11-19 |
| DE3009946C2 (de) | 1983-10-20 |
| IT8048160A0 (it) | 1980-03-14 |
| NL8001385A (nl) | 1980-09-17 |
| GB2045759A (en) | 1980-11-05 |
| AR223209A1 (es) | 1981-07-31 |
| FR2451360A1 (fr) | 1980-10-10 |
| JPS55127339A (en) | 1980-10-02 |
| DE3009946A1 (de) | 1980-09-25 |
| GB2045759B (en) | 1983-07-06 |
| BE882229A (fr) | 1980-09-15 |
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