DE1593357A1 - Verfahren zur Entfernung von Acrolein aus Acrylnitril - Google Patents
Verfahren zur Entfernung von Acrolein aus AcrylnitrilInfo
- Publication number
- DE1593357A1 DE1593357A1 DE19661593357 DE1593357A DE1593357A1 DE 1593357 A1 DE1593357 A1 DE 1593357A1 DE 19661593357 DE19661593357 DE 19661593357 DE 1593357 A DE1593357 A DE 1593357A DE 1593357 A1 DE1593357 A1 DE 1593357A1
- Authority
- DE
- Germany
- Prior art keywords
- acrylonitrile
- acrolein
- solution
- aqueous solution
- temperature
- 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
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 title claims description 68
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 title claims description 39
- 238000000034 method Methods 0.000 title claims description 24
- 239000000243 solution Substances 0.000 claims description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- 239000007864 aqueous solution Substances 0.000 claims description 14
- 229910001868 water Inorganic materials 0.000 claims description 14
- 238000010438 heat treatment Methods 0.000 claims description 11
- 238000010521 absorption reaction Methods 0.000 claims description 10
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 7
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 5
- 230000003197 catalytic effect Effects 0.000 claims description 4
- 238000010574 gas phase reaction Methods 0.000 claims description 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 20
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- 239000000047 product Substances 0.000 description 13
- 229910021529 ammonia Inorganic materials 0.000 description 10
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- 239000006227 byproduct Substances 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 238000004140 cleaning Methods 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000001569 carbon dioxide Substances 0.000 description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 239000012670 alkaline solution Substances 0.000 description 2
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 230000008034 disappearance Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 239000001166 ammonium sulphate Substances 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000007380 fibre production Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000009958 sewing Methods 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 239000012855 volatile organic compound Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/32—Separation; Purification; Stabilisation; Use of additives
- C07C253/34—Separation; Purification
-
- 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
- Y10S203/03—Acrylonitrile
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Discharge Lamps And Accessories Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT1002965 | 1965-05-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1593357A1 true DE1593357A1 (de) | 1970-07-23 |
Family
ID=11133821
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661593357 Pending DE1593357A1 (de) | 1965-05-04 | 1966-04-19 | Verfahren zur Entfernung von Acrolein aus Acrylnitril |
Country Status (12)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0053518A1 (en) * | 1980-12-03 | 1982-06-09 | Asahi Kasei Kogyo Kabushiki Kaisha | Process for producing unsaturated nitrile |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1199697A (en) * | 1967-11-13 | 1970-07-22 | Nitto Chemical Industry Co Ltd | Process for the Removal of Unreacted Ammonia in the Production of Acrylonitrile |
| JPS4925560B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1968-04-16 | 1974-07-01 | ||
| US3936360A (en) * | 1971-04-07 | 1976-02-03 | The Standard Oil Company | Process for distillation and recovery of olefinic nitriles |
| US4234510A (en) * | 1973-06-07 | 1980-11-18 | Standard Oil Company | Recovery of acrylonitrile or methacrylonitrile by condensation |
| US4119497A (en) * | 1975-12-01 | 1978-10-10 | Instituto Mexicano Del Petroleo | Process for the purification of acetonitrile |
| US4238295A (en) * | 1978-12-04 | 1980-12-09 | Standard Oil Company | Energy efficient recovery of acrylonitrile |
| US5606094A (en) * | 1995-01-10 | 1997-02-25 | Baker Hughes Incorporated | Acrolein scavengers |
| US6074532A (en) * | 1998-11-05 | 2000-06-13 | Nalco/Exxon Energy Chemicals, L.P. | Adjunct for removal of aldehydes from chemical manufacturing production streams during distillative purification |
| US6331264B1 (en) | 1999-03-31 | 2001-12-18 | E. I. Du Pont De Nemours And Company | Low emission polymer compositions |
| US6277289B1 (en) | 1999-07-01 | 2001-08-21 | E. I. Du Pont De Nemours And Company | Treatment of aqueous aldehyde waste streams |
| US20040222154A1 (en) * | 2003-05-08 | 2004-11-11 | E.I.Du Pont De Nemours & Company | Treatment of non-aqueous aldehyde waste streams |
| US7196231B2 (en) | 2003-06-27 | 2007-03-27 | Solutia, Inc. | Process for removal of acrolein from acrylonitrile product streams |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3328266A (en) * | 1967-06-27 | Modiano etal separation of acrylonitrile by extractive distillation with water | ||
| US3185636A (en) * | 1962-02-19 | 1965-05-25 | Standard Oil Co | Removal of saturated carbonyls from acrylonitrile |
| FR1336342A (fr) * | 1962-07-20 | 1963-08-30 | Electrochimie Soc | Perfectionnements à la séparation de l'acrylonitrile |
-
1966
- 1966-04-15 NL NL6605077A patent/NL6605077A/xx unknown
- 1966-04-17 IL IL25597A patent/IL25597A/en unknown
- 1966-04-18 GB GB16950/66A patent/GB1138143A/en not_active Expired
- 1966-04-18 BE BE679671D patent/BE679671A/xx unknown
- 1966-04-19 DE DE19661593357 patent/DE1593357A1/de active Pending
- 1966-04-27 US US545618A patent/US3462477A/en not_active Expired - Lifetime
- 1966-04-28 ES ES0326500A patent/ES326500A1/es not_active Expired
- 1966-05-02 CH CH633266A patent/CH484873A/de not_active IP Right Cessation
- 1966-05-02 DK DK223966AA patent/DK119606B/da unknown
- 1966-05-03 LU LU51001A patent/LU51001A1/xx unknown
- 1966-05-03 NO NO162858A patent/NO118434B/no unknown
- 1966-05-04 SE SE06088/66A patent/SE333568B/xx unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0053518A1 (en) * | 1980-12-03 | 1982-06-09 | Asahi Kasei Kogyo Kabushiki Kaisha | Process for producing unsaturated nitrile |
Also Published As
| Publication number | Publication date |
|---|---|
| US3462477A (en) | 1969-08-19 |
| GB1138143A (en) | 1968-12-27 |
| CH484873A (de) | 1970-01-31 |
| SE333568B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1971-03-22 |
| DK119606B (da) | 1971-02-01 |
| ES326500A1 (es) | 1967-03-01 |
| BE679671A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1966-10-03 |
| NL6605077A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1966-11-07 |
| NO118434B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1969-12-29 |
| LU51001A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1966-07-04 |
| IL25597A (en) | 1970-01-29 |
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