DE3009946C2 - Verfahren zur Gewinnung von Methacrylsäure - Google Patents
Verfahren zur Gewinnung von MethacrylsäureInfo
- Publication number
- DE3009946C2 DE3009946C2 DE3009946A DE3009946A DE3009946C2 DE 3009946 C2 DE3009946 C2 DE 3009946C2 DE 3009946 A DE3009946 A DE 3009946A DE 3009946 A DE3009946 A DE 3009946A DE 3009946 C2 DE3009946 C2 DE 3009946C2
- Authority
- DE
- Germany
- Prior art keywords
- methacrylic acid
- solvent
- column
- water
- methacrolein
- 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 title claims description 90
- 238000000034 method Methods 0.000 title claims description 25
- 238000004519 manufacturing process Methods 0.000 title claims description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 171
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 121
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 64
- STNJBCKSHOAVAJ-UHFFFAOYSA-N Methacrolein Chemical compound CC(=C)C=O STNJBCKSHOAVAJ-UHFFFAOYSA-N 0.000 claims description 45
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 claims description 37
- 238000007254 oxidation reaction Methods 0.000 claims description 28
- 230000003647 oxidation Effects 0.000 claims description 26
- 238000004821 distillation Methods 0.000 claims description 19
- 239000007789 gas Substances 0.000 claims description 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 14
- 239000012071 phase Substances 0.000 claims description 13
- 239000011877 solvent mixture Substances 0.000 claims description 13
- 238000009833 condensation Methods 0.000 claims description 7
- 230000005494 condensation Effects 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
- 239000007791 liquid phase Substances 0.000 claims description 3
- 238000000638 solvent extraction Methods 0.000 claims description 3
- 230000003197 catalytic effect Effects 0.000 claims description 2
- 239000011261 inert gas Substances 0.000 claims description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 claims 2
- 239000002904 solvent Substances 0.000 description 72
- 238000000605 extraction Methods 0.000 description 41
- 229920000642 polymer Polymers 0.000 description 26
- 239000000203 mixture Substances 0.000 description 25
- 239000007788 liquid Substances 0.000 description 21
- 238000010791 quenching Methods 0.000 description 21
- 239000007787 solid Substances 0.000 description 20
- 150000002576 ketones Chemical class 0.000 description 17
- 239000000047 product Substances 0.000 description 17
- 238000011084 recovery Methods 0.000 description 17
- 239000012535 impurity Substances 0.000 description 15
- 239000006227 byproduct Substances 0.000 description 13
- 230000000171 quenching effect Effects 0.000 description 13
- 150000001491 aromatic compounds Chemical class 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 10
- 238000000926 separation method Methods 0.000 description 10
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 9
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 8
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 8
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 238000009826 distribution Methods 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 6
- 239000002243 precursor Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000012856 packing Methods 0.000 description 4
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical class [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 3
- 229910002090 carbon oxide Inorganic materials 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 239000002685 polymerization catalyst Substances 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
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000003570 air Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000010953 base metal Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000010586 diagram 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
- 239000004615 ingredient Substances 0.000 description 2
- 239000012263 liquid product Substances 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- ZGHFDIIVVIFNPS-UHFFFAOYSA-N methyl alpha-methylvinyl ketone Natural products CC(=C)C(C)=O ZGHFDIIVVIFNPS-UHFFFAOYSA-N 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 238000005192 partition Methods 0.000 description 2
- 239000013557 residual solvent Substances 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- BWLBGMIXKSTLSX-UHFFFAOYSA-N 2-hydroxyisobutyric acid Chemical compound CC(C)(O)C(O)=O BWLBGMIXKSTLSX-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 229920006061 Kelon® Polymers 0.000 description 1
- NGEWQZIDQIYUNV-UHFFFAOYSA-N L-valinic acid Natural products CC(C)C(O)C(O)=O NGEWQZIDQIYUNV-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
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229920002845 Poly(methacrylic acid) Polymers 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 239000012080 ambient air Substances 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
- 230000009286 beneficial effect Effects 0.000 description 1
- SSRHZSLSLDOUJB-UHFFFAOYSA-N benzene-1,4-diol;toluene Chemical compound CC1=CC=CC=C1.OC1=CC=C(O)C=C1 SSRHZSLSLDOUJB-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000895 extractive distillation Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 1
- 108010084652 homeobox protein PITX1 Proteins 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- YBKWFQNMOCNHCJ-UHFFFAOYSA-N lead;2-methylprop-2-enoic acid Chemical compound [Pb].CC(=C)C(O)=O YBKWFQNMOCNHCJ-UHFFFAOYSA-N 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- -1 methyl n-propyl Chemical group 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
- YMNUETQQDKREEP-UHFFFAOYSA-N nona-1,8-dien-5-one Chemical compound C=CCCC(=O)CCC=C YMNUETQQDKREEP-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000009304 pastoral farming Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000003134 recirculating effect Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US2056379A | 1979-03-15 | 1979-03-15 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3009946A1 DE3009946A1 (de) | 1980-09-25 |
| DE3009946C2 true DE3009946C2 (de) | 1983-10-20 |
Family
ID=21799306
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE3009946A Expired DE3009946C2 (de) | 1979-03-15 | 1980-03-14 | Verfahren zur Gewinnung von Methacrylsäure |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS55127339A (enrdf_load_stackoverflow) |
| AR (1) | AR223209A1 (enrdf_load_stackoverflow) |
| BE (1) | BE882229A (enrdf_load_stackoverflow) |
| BR (1) | BR8001520A (enrdf_load_stackoverflow) |
| DE (1) | DE3009946C2 (enrdf_load_stackoverflow) |
| FR (1) | FR2451360A1 (enrdf_load_stackoverflow) |
| GB (1) | GB2045759B (enrdf_load_stackoverflow) |
| IT (1) | IT1147076B (enrdf_load_stackoverflow) |
| NL (1) | NL8001385A (enrdf_load_stackoverflow) |
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 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2127018B1 (enrdf_load_stackoverflow) * | 1971-02-15 | 1974-04-05 | Sumitomo Chemical Co | |
| JPS4828414A (enrdf_load_stackoverflow) * | 1971-08-13 | 1973-04-14 | ||
| JPS4862712A (enrdf_load_stackoverflow) * | 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 |
| JPS5534784B2 (enrdf_load_stackoverflow) * | 1972-05-23 | 1980-09-09 | ||
| JPS5148609A (ja) * | 1974-10-23 | 1976-04-26 | Asahi Glass Co Ltd | Nidansankanyoruisopuchirenkarano metaku |
| JPS5371011A (en) * | 1976-12-07 | 1978-06-24 | Sumitomo Chem Co Ltd | Extraction of methacrylic acid |
-
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 GB GB8008694A patent/GB2045759B/en not_active Expired
- 1980-03-14 FR FR8005797A patent/FR2451360A1/fr not_active Withdrawn
- 1980-03-14 AR AR280322A patent/AR223209A1/es active
- 1980-03-14 IT IT48160/80A patent/IT1147076B/it active
- 1980-03-14 DE DE3009946A patent/DE3009946C2/de not_active Expired
- 1980-03-15 JP JP3332580A patent/JPS55127339A/ja active Granted
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT |
Also Published As
| Publication number | Publication date |
|---|---|
| GB2045759B (en) | 1983-07-06 |
| GB2045759A (en) | 1980-11-05 |
| JPS55127339A (en) | 1980-10-02 |
| DE3009946A1 (de) | 1980-09-25 |
| AR223209A1 (es) | 1981-07-31 |
| JPS6348857B2 (enrdf_load_stackoverflow) | 1988-09-30 |
| FR2451360A1 (fr) | 1980-10-10 |
| IT8048160A0 (it) | 1980-03-14 |
| BR8001520A (pt) | 1980-11-11 |
| BE882229A (fr) | 1980-09-15 |
| IT1147076B (it) | 1986-11-19 |
| NL8001385A (nl) | 1980-09-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| 8128 | New person/name/address of the agent |
Representative=s name: SPOTT, G., DIPL.-CHEM. DR.RER.NAT., PAT.-ANW., 800 |
|
| 8125 | Change of the main classification |
Ipc: C07C 57/07 |
|
| 8126 | Change of the secondary classification |
Ipc: C07C 51/235 |
|
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |