DE2407236C2 - Verfahren zur Herstellung monomerer Acrylsäure aus Rückständen, die bei der Aufarbeitung roher Acrylsäure anfallen - Google Patents
Verfahren zur Herstellung monomerer Acrylsäure aus Rückständen, die bei der Aufarbeitung roher Acrylsäure anfallenInfo
- Publication number
- DE2407236C2 DE2407236C2 DE2407236A DE2407236A DE2407236C2 DE 2407236 C2 DE2407236 C2 DE 2407236C2 DE 2407236 A DE2407236 A DE 2407236A DE 2407236 A DE2407236 A DE 2407236A DE 2407236 C2 DE2407236 C2 DE 2407236C2
- Authority
- DE
- Germany
- Prior art keywords
- acrylic acid
- residues
- acid
- catalysts
- monomeric
- 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
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 title claims description 27
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 title claims description 26
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 238000000034 method Methods 0.000 title description 14
- 239000003054 catalyst Substances 0.000 claims description 15
- 238000003776 cleavage reaction Methods 0.000 claims description 7
- 230000007017 scission Effects 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 6
- 239000003513 alkali Substances 0.000 claims description 5
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 4
- 238000010626 work up procedure Methods 0.000 claims description 4
- 150000007942 carboxylates Chemical class 0.000 claims description 3
- 229910019142 PO4 Inorganic materials 0.000 claims description 2
- -1 alkaline earth metal carboxylates Chemical class 0.000 claims description 2
- 150000001642 boronic acid derivatives Chemical class 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 150000001735 carboxylic acids Chemical class 0.000 claims description 2
- 235000021317 phosphate Nutrition 0.000 claims description 2
- 150000003013 phosphoric acid derivatives Chemical class 0.000 claims description 2
- RFEXARYJXBYPLD-UHFFFAOYSA-N 3-acetyloxypropanoic acid Chemical compound CC(=O)OCCC(O)=O RFEXARYJXBYPLD-UHFFFAOYSA-N 0.000 claims 1
- ALRHLSYJTWAHJZ-UHFFFAOYSA-N 3-hydroxypropionic acid Chemical compound OCCC(O)=O ALRHLSYJTWAHJZ-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 239000001632 sodium acetate Substances 0.000 description 3
- 235000017281 sodium acetate Nutrition 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- PQUXFUBNSYCQAL-UHFFFAOYSA-N 1-(2,3-difluorophenyl)ethanone Chemical compound CC(=O)C1=CC=CC(F)=C1F PQUXFUBNSYCQAL-UHFFFAOYSA-N 0.000 description 1
- JTNCEQNHURODLX-UHFFFAOYSA-N 2-phenylethanimidamide Chemical compound NC(=N)CC1=CC=CC=C1 JTNCEQNHURODLX-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- ZZAGLMPBQOKGGT-UHFFFAOYSA-N [4-[4-(4-prop-2-enoyloxybutoxy)benzoyl]oxyphenyl] 4-(4-prop-2-enoyloxybutoxy)benzoate Chemical compound C1=CC(OCCCCOC(=O)C=C)=CC=C1C(=O)OC(C=C1)=CC=C1OC(=O)C1=CC=C(OCCCCOC(=O)C=C)C=C1 ZZAGLMPBQOKGGT-UHFFFAOYSA-N 0.000 description 1
- HEAFLBOWLRRIHV-UHFFFAOYSA-N [Na].[P] Chemical compound [Na].[P] HEAFLBOWLRRIHV-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- ITHZDDVSAWDQPZ-UHFFFAOYSA-L barium acetate Chemical compound [Ba+2].CC([O-])=O.CC([O-])=O ITHZDDVSAWDQPZ-UHFFFAOYSA-L 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 230000021523 carboxylation Effects 0.000 description 1
- 238000006473 carboxylation reaction Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000003003 phosphines Chemical group 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 229910000343 potassium bisulfate Inorganic materials 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229940047670 sodium acrylate Drugs 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- NVIFVTYDZMXWGX-UHFFFAOYSA-N sodium metaborate Chemical compound [Na+].[O-]B=O NVIFVTYDZMXWGX-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 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
- C07C51/487—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2407236A DE2407236C2 (de) | 1974-02-15 | 1974-02-15 | Verfahren zur Herstellung monomerer Acrylsäure aus Rückständen, die bei der Aufarbeitung roher Acrylsäure anfallen |
| GB342075A GB1436535A (en) | 1974-02-15 | 1975-01-27 | Recovery of monomeric acrylic acid from residues originating from processed crude acrylic acid |
| NL7501123A NL7501123A (nl) | 1974-02-15 | 1975-01-30 | Werkwijze voor het bereiden van monomeer acrylzuur uit residueen, die worden verkregen bij het opwerken van ruw acrylzuur. |
| CA219,255A CA1039748A (en) | 1974-02-15 | 1975-02-03 | Recovery of monomeric acrylic acid from residues originating from processed crude acrylic acid |
| US05/549,176 US3954854A (en) | 1974-02-15 | 1975-02-12 | Recovery of monomeric acrylic acid from residues originating from processed crude acrylic acid |
| JP50017739A JPS5756899B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-02-15 | 1975-02-12 | |
| IT48154/75A IT1029716B (it) | 1974-02-15 | 1975-02-13 | Procedimento per produrre acido acrilico monomerico |
| BE153316A BE825482A (fr) | 1974-02-15 | 1975-02-13 | Procede de recuperation de l'acide acrylique monomere a partir de residus du traitement de l'acide acrylique brut |
| FR7504715A FR2261252B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-02-15 | 1975-02-14 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2407236A DE2407236C2 (de) | 1974-02-15 | 1974-02-15 | Verfahren zur Herstellung monomerer Acrylsäure aus Rückständen, die bei der Aufarbeitung roher Acrylsäure anfallen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2407236A1 DE2407236A1 (de) | 1975-09-04 |
| DE2407236C2 true DE2407236C2 (de) | 1983-02-03 |
Family
ID=5907485
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2407236A Expired DE2407236C2 (de) | 1974-02-15 | 1974-02-15 | Verfahren zur Herstellung monomerer Acrylsäure aus Rückständen, die bei der Aufarbeitung roher Acrylsäure anfallen |
Country Status (9)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012163931A1 (de) | 2011-06-03 | 2012-12-06 | Basf Se | Wässrige lösung, enthaltend acrylsäure und deren konjugierte base |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4317926A (en) | 1978-01-19 | 1982-03-02 | Nippon Shokubai Kagaku Kogyo Co., Ltd. | Process for preparing and recovering acrylic acid |
| US4617405A (en) * | 1984-09-25 | 1986-10-14 | A. E. Staley Manufacturing Company | Preparation of alpha, beta-unsaturated carbonyl compounds |
| FR2727964B1 (fr) * | 1994-12-12 | 1997-01-24 | Atochem Elf Sa | Procede de recuperation des produits nobles legers contenus dans les residus de distillation des procedes de fabrication de l'acide acrylique et de ses esters |
| DE50003359D1 (de) * | 1999-03-06 | 2003-09-25 | Basf Ag | Verfahren zur herstellung von acrylsäure |
| MY122671A (en) | 1999-03-06 | 2006-04-29 | Basf Ag | Fractional condensation of a product gas mixture containing acrylic acid |
| JP4048076B2 (ja) † | 2001-07-10 | 2008-02-13 | 株式会社日本触媒 | ミカエル型付加物の分解方法 |
| CN1781897A (zh) * | 2002-03-25 | 2006-06-07 | 嘉吉有限公司 | 制造β－羟基羧酸烷氧基衍生物的方法 |
| JP4302934B2 (ja) | 2002-04-25 | 2009-07-29 | 株式会社日本触媒 | ミカエル型付加物の分解方法 |
| DE102004008575A1 (de) * | 2004-02-19 | 2005-09-08 | Stockhausen Gmbh | Spaltung oligomerer (Meth)acrylsäure in flüssiger Phase unter Druck |
| WO2005095320A1 (en) * | 2004-04-02 | 2005-10-13 | Ciba Specialty Chemicals Water Treatments Limited | Preparation of acrylic acid derivatives from alpha or beta-hydroxy carboxylic acids |
| TWD152381S (zh) | 2012-03-16 | 2013-03-11 | 開富喜股份有限公司 | 螺栓固定劑（四） |
| WO2015058118A1 (en) | 2013-10-17 | 2015-04-23 | Cargill, Incorporated | Method for producing alkyl hydroxyalkanoates |
| US10239819B2 (en) * | 2014-10-17 | 2019-03-26 | Cargill, Incorporated | Methods for producing an ester of an alpha, beta-unsaturated carboxylic acid |
| MA41510A (fr) | 2015-02-13 | 2017-12-19 | Novomer Inc | Procédé de production d'acide acrylique |
| MA41513A (fr) | 2015-02-13 | 2017-12-19 | Novomer Inc | Procédé de distillation pour la production d'acide acrylique |
| CN108026013B (zh) | 2015-07-31 | 2022-09-13 | 诺沃梅尔公司 | 用于丙烯酸及其前体的生产系统/生产方法 |
| US10065914B1 (en) * | 2017-04-24 | 2018-09-04 | Novomer, Inc. | Thermolysis of polypropiolactone to produce acrylic acid |
| US10781156B2 (en) | 2017-06-30 | 2020-09-22 | Novomer, Inc. | Compositions for improved production of acrylic acid |
| KR20210137037A (ko) | 2019-03-08 | 2021-11-17 | 노보머, 인코포레이티드 | 아미드 및 니트릴 화합물을 생산하기 위한 통합 방법 및 시스템 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2485510A (en) * | 1946-02-13 | 1949-10-18 | American Cyanamid Co | Preparation of acrylic acid and esters thereof |
| US3086046A (en) * | 1959-01-30 | 1963-04-16 | Basf Ag | Cleavage of diacrylic acid to form acrylic acid |
| US3639466A (en) * | 1967-04-03 | 1972-02-01 | Basf Ag | Production of acrylic acid from residues obtained in working up acrylic acid |
-
1974
- 1974-02-15 DE DE2407236A patent/DE2407236C2/de not_active Expired
-
1975
- 1975-01-27 GB GB342075A patent/GB1436535A/en not_active Expired
- 1975-01-30 NL NL7501123A patent/NL7501123A/xx not_active Application Discontinuation
- 1975-02-03 CA CA219,255A patent/CA1039748A/en not_active Expired
- 1975-02-12 JP JP50017739A patent/JPS5756899B2/ja not_active Expired
- 1975-02-12 US US05/549,176 patent/US3954854A/en not_active Expired - Lifetime
- 1975-02-13 IT IT48154/75A patent/IT1029716B/it active
- 1975-02-13 BE BE153316A patent/BE825482A/xx not_active IP Right Cessation
- 1975-02-14 FR FR7504715A patent/FR2261252B1/fr not_active Expired
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012163931A1 (de) | 2011-06-03 | 2012-12-06 | Basf Se | Wässrige lösung, enthaltend acrylsäure und deren konjugierte base |
| US9150483B2 (en) | 2011-06-03 | 2015-10-06 | Basf Se | Aqueous solution comprising acrylic acid and the conjugate base thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5756899B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1982-12-02 |
| JPS50116416A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-09-11 |
| NL7501123A (nl) | 1975-08-19 |
| CA1039748A (en) | 1978-10-03 |
| BE825482A (fr) | 1975-08-13 |
| IT1029716B (it) | 1979-03-20 |
| DE2407236A1 (de) | 1975-09-04 |
| FR2261252B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1980-04-18 |
| FR2261252A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-09-12 |
| GB1436535A (en) | 1976-05-19 |
| US3954854A (en) | 1976-05-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |