DE2117978A1 - Verfahren zur Gewinnung und Reinigung eines olefinischen Nitrile - Google Patents
Verfahren zur Gewinnung und Reinigung eines olefinischen NitrileInfo
- Publication number
- DE2117978A1 DE2117978A1 DE19712117978 DE2117978A DE2117978A1 DE 2117978 A1 DE2117978 A1 DE 2117978A1 DE 19712117978 DE19712117978 DE 19712117978 DE 2117978 A DE2117978 A DE 2117978A DE 2117978 A1 DE2117978 A1 DE 2117978A1
- Authority
- DE
- Germany
- Prior art keywords
- column
- methacrylonitrile
- hydrogen cyanide
- recovery column
- olefinic
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims description 38
- 150000002825 nitriles Chemical class 0.000 title claims description 28
- 238000000746 purification Methods 0.000 title claims description 10
- 238000004519 manufacturing process Methods 0.000 title description 5
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 62
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 45
- 238000011084 recovery Methods 0.000 claims description 44
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 claims description 40
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 21
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 15
- 238000004821 distillation Methods 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 8
- 238000000605 extraction Methods 0.000 claims description 5
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 5
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 4
- 150000001336 alkenes Chemical class 0.000 claims description 3
- 238000005194 fractionation Methods 0.000 claims description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 3
- -1 olefin nitrile Chemical class 0.000 claims description 2
- 230000001105 regulatory effect Effects 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
- 239000000047 product Substances 0.000 description 25
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 20
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- 229910021529 ammonia Inorganic materials 0.000 description 10
- 239000007788 liquid Substances 0.000 description 9
- 238000010791 quenching Methods 0.000 description 9
- STNJBCKSHOAVAJ-UHFFFAOYSA-N Methacrolein Chemical compound CC(=C)C=O STNJBCKSHOAVAJ-UHFFFAOYSA-N 0.000 description 8
- 239000006096 absorbing agent Substances 0.000 description 8
- 239000006227 byproduct Substances 0.000 description 8
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 7
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 230000000171 quenching effect Effects 0.000 description 5
- 239000002699 waste material Substances 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 239000000470 constituent Substances 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 230000005484 gravity Effects 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 229920000620 organic polymer Polymers 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 238000005191 phase separation Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000010865 sewage Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000012808 vapor phase Substances 0.000 description 2
- 239000002351 wastewater Substances 0.000 description 2
- 238000004065 wastewater treatment Methods 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000000895 extractive distillation Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000010574 gas phase reaction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- LRDFRRGEGBBSRN-UHFFFAOYSA-N isobutyronitrile Chemical compound CC(C)C#N LRDFRRGEGBBSRN-UHFFFAOYSA-N 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000011027 product recovery Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 102220129016 rs782480409 Human genes 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002689 soil 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Vaporization, Distillation, Condensation, Sublimation, And Cold Traps (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US2902270A | 1970-04-16 | 1970-04-16 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2117978A1 true DE2117978A1 (de) | 1971-10-28 |
| DE2117978C2 DE2117978C2 (enrdf_load_stackoverflow) | 1987-10-22 |
Family
ID=21846801
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712117978 Granted DE2117978A1 (de) | 1970-04-16 | 1971-04-14 | Verfahren zur Gewinnung und Reinigung eines olefinischen Nitrile |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS5023017B1 (enrdf_load_stackoverflow) |
| AT (1) | AT315140B (enrdf_load_stackoverflow) |
| BE (1) | BE765842A (enrdf_load_stackoverflow) |
| CA (1) | CA945932A (enrdf_load_stackoverflow) |
| CH (1) | CH523228A (enrdf_load_stackoverflow) |
| DE (1) | DE2117978A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2089698A5 (enrdf_load_stackoverflow) |
| GB (1) | GB1350486A (enrdf_load_stackoverflow) |
| LU (1) | LU62971A1 (enrdf_load_stackoverflow) |
| NL (1) | NL178249C (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2517300A1 (de) * | 1975-04-18 | 1976-10-28 | Standard Oil Co Ohio | Verfahren zur gewinnung und reinigung von acrylnitril oder methacrylnitril |
| DE2918979A1 (de) * | 1978-05-15 | 1979-11-22 | Lummus Co | Verfahren zur herstellung von nitrilen |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4238295A (en) * | 1978-12-04 | 1980-12-09 | Standard Oil Company | Energy efficient recovery of acrylonitrile |
| DE3172080D1 (en) * | 1980-12-03 | 1985-10-03 | Asahi Chemical Ind | Method for recovering and utilizing waste heat |
| US4334965A (en) * | 1980-12-31 | 1982-06-15 | Standard Oil Company | Process for recovery of olefinic nitriles |
| DE3363585D1 (en) * | 1982-06-22 | 1986-06-26 | Asahi Chemical Ind | Process for producing methacrylonitrile |
| US4404064A (en) * | 1982-12-30 | 1983-09-13 | Monsanto Company | Water extractive distillation of olefinically unsaturated nitriles |
| JP5246869B2 (ja) * | 2009-03-24 | 2013-07-24 | 旭化成ケミカルズ株式会社 | アクリロニトリルの精製方法 |
| CN114307207A (zh) * | 2014-09-29 | 2022-04-12 | 英尼奥斯欧洲股份公司 | 用于工艺流的蒸发系统 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DD58300A (enrdf_load_stackoverflow) * | ||||
| DE1493121A1 (de) * | 1964-12-24 | 1969-04-10 | Electro Chimie Metal | Verfahren zur Trennung von Acrylnitril und Acetonitril aus deren,gegebenenfalls noch andere Verunreinigungen enthaltenden Mischungen |
| DE1920083A1 (de) * | 1969-04-21 | 1970-01-29 | Lentia Gmbh | Verfahren zur kontinuierlichen Trennung von Acrylnitril und Acetonitril |
-
1971
- 1971-03-22 CA CA108,336A patent/CA945932A/en not_active Expired
- 1971-04-08 AT AT300071A patent/AT315140B/de not_active IP Right Cessation
- 1971-04-09 LU LU62971D patent/LU62971A1/xx unknown
- 1971-04-14 DE DE19712117978 patent/DE2117978A1/de active Granted
- 1971-04-15 CH CH546671A patent/CH523228A/fr not_active IP Right Cessation
- 1971-04-15 FR FR7113319A patent/FR2089698A5/fr not_active Expired
- 1971-04-15 JP JP46023551A patent/JPS5023017B1/ja active Pending
- 1971-04-16 NL NL7105164A patent/NL178249C/xx not_active IP Right Cessation
- 1971-04-16 BE BE765842A patent/BE765842A/xx not_active IP Right Cessation
- 1971-04-19 GB GB2672871A patent/GB1350486A/en not_active Expired
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DD58300A (enrdf_load_stackoverflow) * | ||||
| DE1493121A1 (de) * | 1964-12-24 | 1969-04-10 | Electro Chimie Metal | Verfahren zur Trennung von Acrylnitril und Acetonitril aus deren,gegebenenfalls noch andere Verunreinigungen enthaltenden Mischungen |
| DE1920083A1 (de) * | 1969-04-21 | 1970-01-29 | Lentia Gmbh | Verfahren zur kontinuierlichen Trennung von Acrylnitril und Acetonitril |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2517300A1 (de) * | 1975-04-18 | 1976-10-28 | Standard Oil Co Ohio | Verfahren zur gewinnung und reinigung von acrylnitril oder methacrylnitril |
| DE2918979A1 (de) * | 1978-05-15 | 1979-11-22 | Lummus Co | Verfahren zur herstellung von nitrilen |
Also Published As
| Publication number | Publication date |
|---|---|
| CA945932A (en) | 1974-04-23 |
| GB1350486A (en) | 1974-04-18 |
| CH523228A (fr) | 1972-05-31 |
| FR2089698A5 (enrdf_load_stackoverflow) | 1972-01-07 |
| NL178249C (nl) | 1986-02-17 |
| LU62971A1 (enrdf_load_stackoverflow) | 1972-02-25 |
| NL7105164A (enrdf_load_stackoverflow) | 1971-10-19 |
| DE2117978C2 (enrdf_load_stackoverflow) | 1987-10-22 |
| BE765842A (fr) | 1971-10-18 |
| AT315140B (de) | 1974-05-10 |
| NL178249B (nl) | 1985-09-16 |
| JPS5023017B1 (enrdf_load_stackoverflow) | 1975-08-05 |
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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: REDIES, B., DIPL.-CHEM. DR.RER.NAT., PAT.-ANW., 40 |
|
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition |