DE3429391C2 - - Google Patents
Info
- Publication number
- DE3429391C2 DE3429391C2 DE3429391A DE3429391A DE3429391C2 DE 3429391 C2 DE3429391 C2 DE 3429391C2 DE 3429391 A DE3429391 A DE 3429391A DE 3429391 A DE3429391 A DE 3429391A DE 3429391 C2 DE3429391 C2 DE 3429391C2
- Authority
- DE
- Germany
- Prior art keywords
- acrylic acid
- water
- acetic acid
- column
- azeotropic
- 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 159
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 84
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 84
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 60
- 239000003795 chemical substances by application Substances 0.000 claims description 34
- 238000000034 method Methods 0.000 claims description 34
- 238000004821 distillation Methods 0.000 claims description 26
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 claims description 20
- 239000007789 gas Substances 0.000 claims description 20
- 238000009835 boiling Methods 0.000 claims description 18
- 239000007795 chemical reaction product Substances 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 13
- 239000007864 aqueous solution Substances 0.000 claims description 12
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 11
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 11
- 238000010521 absorption reaction Methods 0.000 claims description 10
- 238000007254 oxidation reaction Methods 0.000 claims description 10
- 238000011084 recovery Methods 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 7
- 230000003197 catalytic effect Effects 0.000 claims description 6
- 230000003647 oxidation Effects 0.000 claims description 6
- 239000012808 vapor phase Substances 0.000 claims description 6
- 238000001816 cooling Methods 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
- 229910001882 dioxygen Inorganic materials 0.000 claims 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 14
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 14
- 238000000926 separation method Methods 0.000 description 12
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 238000000605 extraction Methods 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 7
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 6
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 6
- 230000018044 dehydration Effects 0.000 description 6
- 238000006297 dehydration reaction Methods 0.000 description 6
- 238000010533 azeotropic distillation Methods 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 description 5
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 description 5
- 238000002955 isolation Methods 0.000 description 5
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 3
- 239000001569 carbon dioxide Substances 0.000 description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- 239000011261 inert gas Substances 0.000 description 3
- 229910052750 molybdenum Inorganic materials 0.000 description 3
- 239000011733 molybdenum Substances 0.000 description 3
- 239000001294 propane Substances 0.000 description 3
- 239000002699 waste material Substances 0.000 description 3
- 239000002351 wastewater Substances 0.000 description 3
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- WUJISAYEUPRJOG-UHFFFAOYSA-N molybdenum vanadium Chemical compound [V].[Mo] WUJISAYEUPRJOG-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- XPZBNIUWMDJFPW-UHFFFAOYSA-N 2,2,3-trimethylcyclohexan-1-one Chemical compound CC1CCCC(=O)C1(C)C XPZBNIUWMDJFPW-UHFFFAOYSA-N 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 239000003570 air Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000007084 catalytic combustion reaction Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000012527 feed solution Substances 0.000 description 1
- JEGUKCSWCFPDGT-UHFFFAOYSA-N h2o hydrate Chemical compound O.O JEGUKCSWCFPDGT-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 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
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000002912 waste gas Substances 0.000 description 1
- 238000004065 wastewater treatment Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
- C07C57/03—Monocarboxylic acids
- C07C57/04—Acrylic acid; Methacrylic acid
-
- 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
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
- C07C51/44—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation by distillation
- C07C51/46—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation by distillation by azeotropic distillation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58145645A JPH0615495B2 (ja) | 1983-08-11 | 1983-08-11 | アクリル酸の精製方法 |
| JP58146528A JPH0615496B2 (ja) | 1983-08-12 | 1983-08-12 | アクリル酸の製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3429391A1 DE3429391A1 (de) | 1985-02-21 |
| DE3429391C2 true DE3429391C2 (forum.php) | 1989-03-02 |
Family
ID=26476736
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19843429391 Granted DE3429391A1 (de) | 1983-08-11 | 1984-08-09 | Verfahren zur herstellung von acrylsaeure |
Country Status (5)
| Country | Link |
|---|---|
| KR (1) | KR900006901B1 (forum.php) |
| DE (1) | DE3429391A1 (forum.php) |
| FR (1) | FR2554809B1 (forum.php) |
| GB (1) | GB2146636B (forum.php) |
| MX (1) | MX161562A (forum.php) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3937462B2 (ja) * | 1994-08-04 | 2007-06-27 | 三菱化学株式会社 | アクリル酸精製法 |
| JP3028925B2 (ja) * | 1995-12-05 | 2000-04-04 | 株式会社日本触媒 | アクリル酸の製造方法 |
| DE19600955A1 (de) * | 1996-01-12 | 1997-07-17 | Basf Ag | Verfahren zur Herstellung von Acrylsäure und deren Ester |
| DE19624674A1 (de) | 1996-06-20 | 1998-01-02 | Basf Ag | Verfahren zur Entsorgung von bei der Acrylsäure- oder Methacrylsäure-Herstellung anfallenden Nebenkomponenten |
| DE19740252A1 (de) | 1997-09-12 | 1999-03-18 | Basf Ag | Verfahren zur Herstellung von Acrylsäure und Methacrylsäure |
| DE19814387A1 (de) | 1998-03-31 | 1999-10-07 | Basf Ag | Verfahren zur Herstellung von Acrylsäure und Acrylsäureestern |
| DE19814375A1 (de) | 1998-03-31 | 1999-10-07 | Basf Ag | Verfahren zur Herstellung von Acrylsäure und Acrylsäureestern |
| DE19833049A1 (de) | 1998-07-22 | 2000-01-27 | Basf Ag | Verfahren zur Herstellung von Acrylsäure |
| TW553929B (en) * | 1999-03-05 | 2003-09-21 | Rohm & Haas | Process for preparing (meth)acrylic acid |
| JP2001213839A (ja) | 2000-02-03 | 2001-08-07 | Nippon Shokubai Co Ltd | （メタ）アクリル酸の製造方法 |
| JP2001247510A (ja) | 2000-03-08 | 2001-09-11 | Nippon Shokubai Co Ltd | アクリル酸の製造方法 |
| JP4050184B2 (ja) | 2003-05-13 | 2008-02-20 | 株式会社日本触媒 | 脂肪族カルボン酸の製造方法 |
| 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 |
| DE602005021361D1 (de) | 2004-08-02 | 2010-07-01 | Lg Chemical Ltd | Verfahren zur herstellung von (meth)acrylsäure |
| EP2135656A1 (en) | 2008-05-30 | 2009-12-23 | Rohm and Haas Company | Method for production of purified (Meth)acrylic acid |
| FR2935971B1 (fr) | 2008-09-16 | 2010-11-19 | Arkema France | Acide bio-acrylique de grade polymere et son procede de fabrication a partir de glycerol. |
| FR2948365B1 (fr) | 2009-07-22 | 2011-09-09 | Arkema France | Procede de fabrication d'acide acrylique bio-ressource a partir de glycerol |
| EP3770145A1 (en) | 2019-07-24 | 2021-01-27 | Basf Se | A process for the continuous production of either acrolein or acrylic acid as the target product from propene |
| FR3100243B1 (fr) * | 2019-08-28 | 2021-07-30 | Arkema France | Elimination du formaldehyde dans les eaux usees par un traitement d'oxydation |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2050234A (en) * | 1934-07-13 | 1936-08-04 | Tennessee Eastman Corp | Process for dehydration of acetic acid and other lower fatty acids |
| GB995472A (en) * | 1963-05-16 | 1965-06-16 | Distillers Co Yeast Ltd | Improvements in or relating to acrylic acid production |
| US3666632A (en) * | 1968-10-08 | 1972-05-30 | Asahi Chemical Ind | Method for the separation of acrylic acid from aqueous solution containing acrylic acid and acetic acid |
| CA935779A (en) * | 1969-06-26 | 1973-10-23 | Tabata Hisanobu | Process for preparing heavy water from sea water |
| DE2104506C3 (de) * | 1971-02-01 | 1974-07-18 | Knapsack Ag, 5033 Huerth-Knapsack | Verfahren zur Abtrennung von Acrylsäure und Essigsäure aus wäßriger Rohacrylsäure |
| DE2121123C3 (de) * | 1971-04-29 | 1980-06-12 | Basf Ag, 6700 Ludwigshafen | Verfahren zum Abtrennen von Wasser aus wäßrigen Lösungen von Acrylsäure durch azeotrope Destillation |
| GB1458396A (en) * | 1972-12-27 | 1976-12-15 | Degussa | Process for obtaining acrylic acid and optionally acrolein |
| JPS52108917A (en) * | 1976-03-11 | 1977-09-12 | Nippon Shokubai Kagaku Kogyo Co Ltd | Preparation of acrylic acid by vapor-phase catalytic oxidation of prop ylene |
| US4147721A (en) * | 1978-04-06 | 1979-04-03 | Halcon Research And Development Corporation | Process for recovering methacrylic acid |
| JPS5690034A (en) * | 1979-12-25 | 1981-07-21 | Mitsubishi Petrochem Co Ltd | Purification of acrylic acid |
-
1984
- 1984-08-08 GB GB08420153A patent/GB2146636B/en not_active Expired
- 1984-08-09 DE DE19843429391 patent/DE3429391A1/de active Granted
- 1984-08-10 MX MX202336A patent/MX161562A/es unknown
- 1984-08-10 KR KR1019840004818A patent/KR900006901B1/ko not_active Expired
- 1984-08-13 FR FR8412731A patent/FR2554809B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB2146636B (en) | 1987-02-04 |
| KR850001720A (ko) | 1985-04-01 |
| GB2146636A (en) | 1985-04-24 |
| DE3429391A1 (de) | 1985-02-21 |
| GB8420153D0 (en) | 1984-09-12 |
| KR900006901B1 (ko) | 1990-09-24 |
| MX161562A (es) | 1990-11-06 |
| FR2554809B1 (fr) | 1987-12-18 |
| FR2554809A1 (fr) | 1985-05-17 |
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| DE3429391C2 (forum.php) | ||
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OP8 | Request for examination as to paragraph 44 patent law | ||
| D2 | Grant after examination | ||
| 8363 | Opposition against the patent | ||
| 8331 | Complete revocation |