DE1468956A1 - Verfahren zur Herstellung reiner Acrylsaeure - Google Patents
Verfahren zur Herstellung reiner AcrylsaeureInfo
- Publication number
- DE1468956A1 DE1468956A1 DE19641468956 DE1468956A DE1468956A1 DE 1468956 A1 DE1468956 A1 DE 1468956A1 DE 19641468956 DE19641468956 DE 19641468956 DE 1468956 A DE1468956 A DE 1468956A DE 1468956 A1 DE1468956 A1 DE 1468956A1
- Authority
- DE
- Germany
- Prior art keywords
- acrylic acid
- water
- sole
- acid
- distillation
- 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.)
- Pending
Links
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 title claims description 42
- 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 40
- 238000000034 method Methods 0.000 title claims description 13
- 238000004519 manufacturing process Methods 0.000 title description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
- 239000000203 mixture Substances 0.000 claims description 15
- 239000000243 solution Substances 0.000 claims description 10
- 238000004821 distillation Methods 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 7
- 239000007864 aqueous solution Substances 0.000 claims description 7
- 238000009835 boiling Methods 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 230000002745 absorbent Effects 0.000 claims 1
- 239000002250 absorbent Substances 0.000 claims 1
- 239000006096 absorbing agent Substances 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 238000010533 azeotropic distillation Methods 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 238000000998 batch distillation Methods 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- WSGYTJNNHPZFKR-UHFFFAOYSA-N 3-hydroxypropanenitrile Chemical compound OCCC#N WSGYTJNNHPZFKR-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 239000004909 Moisturizer Substances 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 239000012223 aqueous fraction Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229910002090 carbon oxide Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 230000001333 moisturizer Effects 0.000 description 1
- 238000013021 overheating Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000003822 preparative gas chromatography Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- MHWRYTCHHJGQFQ-UHFFFAOYSA-N prop-2-enoic acid hydrate Chemical compound O.OC(=O)C=C MHWRYTCHHJGQFQ-UHFFFAOYSA-N 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
- 230000000630 rising effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000012748 slip agent Substances 0.000 description 1
- 239000002904 solvent 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
- C07C51/43—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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S203/00—Distillation: processes, separatory
- Y10S203/22—Accessories
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural 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 |
|---|---|---|---|
| FR928802A FR1359885A (fr) | 1963-03-21 | 1963-03-21 | Procédé de fabrication d'acide acrylique glacial |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1468956A1 true DE1468956A1 (de) | 1969-01-02 |
Family
ID=8799784
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19641468956 Pending DE1468956A1 (de) | 1963-03-21 | 1964-02-25 | Verfahren zur Herstellung reiner Acrylsaeure |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3432401A (en, 2012) |
| JP (1) | JPS4827292B1 (en, 2012) |
| BE (1) | BE643942A (en, 2012) |
| DE (1) | DE1468956A1 (en, 2012) |
| ES (1) | ES296656A1 (en, 2012) |
| FR (1) | FR1359885A (en, 2012) |
| GB (1) | GB1055532A (en, 2012) |
| LU (1) | LU45409A1 (en, 2012) |
| NL (1) | NL6401921A (en, 2012) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3493471A (en) * | 1967-12-01 | 1970-02-03 | Dow Chemical Co | Acrylic acid purification |
| 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 |
| US3527677A (en) * | 1969-03-06 | 1970-09-08 | Goodrich Co B F | Process for dehydration of aqueous acrylic acid solutions by extractive - azeotropic distillation with 2-ethylhexanol or 2-ethylhexylacrylate |
| BE786398A (fr) * | 1971-07-21 | 1973-01-18 | Basf Ag | Procede de preparation de l'acide acrylique anhydre |
| DE2241714A1 (de) * | 1972-08-24 | 1974-03-28 | Basf Ag | Verfahren zur abtrennung von acrylsaeure aus den reaktionsgasen der propylenoder acroleinoxydation |
| US4021310A (en) * | 1972-12-22 | 1977-05-03 | Nippon Shokubai Kagaku Kogyo Co., Ltd. | Method for inhibiting the polymerization of acrylic acid or its esters |
| FR2394512A1 (fr) * | 1977-06-14 | 1979-01-12 | Rhone Poulenc Ind | Procede de separation d'acide acrylique a partir de ses solutions dans le phosphate de tri-n-butyle |
| US4820385A (en) * | 1988-02-18 | 1989-04-11 | Monsanto Company | Purification of alkyl glyoxylate in a continuous column by azeotropic distillation |
| US6084127A (en) * | 1997-02-28 | 2000-07-04 | Nippon Shokubai Co Ltd | Method for recovering acrylic acid |
| US6926810B2 (en) * | 2001-03-15 | 2005-08-09 | A. E. Staley Manufacturing Co. | Process for obtaining an organic acid from an organic acid ammonium salt, an organic acid amide, or an alkylamine organic acid complex |
| US6984293B2 (en) * | 2001-03-15 | 2006-01-10 | Tate & Lyle Ingredients | Azeotropic distillation of cyclic esters of hydroxy organic acids |
| US6982026B2 (en) * | 2001-03-15 | 2006-01-03 | Tate & Lyle Ingredients Americas, Inc. | Azeotropic distillation process for producing organic acids or organic acid amides |
| US20030150705A1 (en) * | 2002-01-08 | 2003-08-14 | Deshpande Sanjeev D. | Acrylic acid recovery utilizing ethyl acrylate and selected co-solvents |
| US7128813B2 (en) * | 2002-05-01 | 2006-10-31 | Rohm And Haas Company | Process for manufacturing high purity methacrylic acid |
| US11866631B2 (en) | 2019-04-29 | 2024-01-09 | Ecolab Usa Inc. | Oxygenated aminophenol compounds and methods for preventing monomer polymerization |
| AU2020265570A1 (en) | 2019-04-29 | 2021-11-25 | Ecolab Usa Inc. | Oxygenated aromatic amines and use as antioxidants |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1668380A (en) * | 1923-12-28 | 1928-05-01 | Distilleries Des Deux Sevres | Continuous process for the dehydration of volatile fatty acids |
| US1915002A (en) * | 1929-03-19 | 1933-06-20 | Us Ind Alcohol Co | Process of obtaining fatty acids in anhydrous state from aqueous solutions |
| US2033978A (en) * | 1932-04-01 | 1936-03-17 | Dreyfus Henry | Concentration of lower aliphatic acids |
| FR1169740A (fr) * | 1956-03-22 | 1959-01-05 | Solvay Werke Gmbh | Procédé de concentration d'acide acrylique aqueux |
| US3337740A (en) * | 1962-02-13 | 1967-08-22 | Deering Milliken Res Corp | Process for separating acrylic acid from impurities |
-
1963
- 1963-03-21 FR FR928802A patent/FR1359885A/fr not_active Expired
-
1964
- 1964-02-12 LU LU45409D patent/LU45409A1/xx unknown
- 1964-02-18 BE BE643942D patent/BE643942A/xx unknown
- 1964-02-20 ES ES0296656A patent/ES296656A1/es not_active Expired
- 1964-02-25 DE DE19641468956 patent/DE1468956A1/de active Pending
- 1964-02-27 NL NL6401921A patent/NL6401921A/xx unknown
- 1964-03-18 US US352829A patent/US3432401A/en not_active Expired - Lifetime
- 1964-03-19 GB GB11743/64A patent/GB1055532A/en not_active Expired
- 1964-03-19 JP JP39015066A patent/JPS4827292B1/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| US3432401A (en) | 1969-03-11 |
| ES296656A1 (es) | 1964-05-01 |
| JPS4827292B1 (en, 2012) | 1973-08-21 |
| LU45409A1 (en, 2012) | 1964-04-13 |
| NL6401921A (en, 2012) | 1964-09-22 |
| BE643942A (en, 2012) | 1964-06-15 |
| GB1055532A (en) | 1967-01-18 |
| FR1359885A (fr) | 1964-04-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| SH | Request for examination between 03.10.1968 and 22.04.1971 |