DE1468958B2 - Verfahren zur Gewinnung von Acrylnitril und Acroleincyanhydrin - Google Patents
Verfahren zur Gewinnung von Acrylnitril und AcroleincyanhydrinInfo
- Publication number
- DE1468958B2 DE1468958B2 DE19641468958 DE1468958A DE1468958B2 DE 1468958 B2 DE1468958 B2 DE 1468958B2 DE 19641468958 DE19641468958 DE 19641468958 DE 1468958 A DE1468958 A DE 1468958A DE 1468958 B2 DE1468958 B2 DE 1468958B2
- Authority
- DE
- Germany
- Prior art keywords
- acrylonitrile
- acrolein
- distillation
- mixture
- cyanohydrin
- 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
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 title claims description 36
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 title claims description 27
- 238000000034 method Methods 0.000 title claims description 11
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 238000004821 distillation Methods 0.000 claims description 18
- 239000000047 product Substances 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 16
- 239000012071 phase Substances 0.000 claims description 13
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 12
- 239000007788 liquid Substances 0.000 claims description 9
- 150000001299 aldehydes Chemical class 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 239000012535 impurity Substances 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 238000009833 condensation Methods 0.000 claims description 5
- 230000005494 condensation Effects 0.000 claims description 5
- 239000007789 gas Substances 0.000 claims description 5
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 5
- 239000011707 mineral Substances 0.000 claims description 5
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 5
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 5
- 101150046432 Tril gene Proteins 0.000 claims description 3
- 150000002825 nitriles Chemical class 0.000 claims description 3
- 238000007254 oxidation reaction Methods 0.000 claims description 3
- 239000002689 soil Substances 0.000 claims description 3
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 2
- 239000006227 byproduct Substances 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 239000000470 constituent Substances 0.000 claims description 2
- 239000012074 organic phase Substances 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 10
- 229910021529 ammonia Inorganic materials 0.000 claims 5
- 238000005406 washing Methods 0.000 claims 5
- 239000002253 acid Substances 0.000 claims 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims 2
- 238000000605 extraction Methods 0.000 claims 2
- 230000006641 stabilisation Effects 0.000 claims 2
- 238000011105 stabilization Methods 0.000 claims 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 229910021536 Zeolite Inorganic materials 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- QYTBWVFCSVDTEC-UHFFFAOYSA-N azane;iron Chemical compound N.[Fe] QYTBWVFCSVDTEC-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 239000001569 carbon dioxide Substances 0.000 claims 1
- 229910002092 carbon dioxide Inorganic materials 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 claims 1
- 238000011109 contamination Methods 0.000 claims 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims 1
- 230000008030 elimination Effects 0.000 claims 1
- 238000003379 elimination reaction Methods 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 230000002779 inactivation Effects 0.000 claims 1
- 239000004615 ingredient Substances 0.000 claims 1
- 150000002576 ketones Chemical class 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 239000000178 monomer Substances 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 230000008520 organization Effects 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 150000003460 sulfonic acids Chemical class 0.000 claims 1
- 239000010457 zeolite Substances 0.000 claims 1
- 238000000354 decomposition reaction Methods 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 2
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 2
- 101150096316 5 gene Proteins 0.000 description 1
- OJVABJMSSDUECT-UHFFFAOYSA-L berberin sulfate Chemical compound [O-]S([O-])(=O)=O.C1=C2CC[N+]3=CC4=C(OC)C(OC)=CC=C4C=C3C2=CC2=C1OCO2.C1=C2CC[N+]3=CC4=C(OC)C(OC)=CC=C4C=C3C2=CC2=C1OCO2 OJVABJMSSDUECT-UHFFFAOYSA-L 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 239000010871 livestock manure Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000012808 vapor phase Substances 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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR927990A FR1359316A (fr) | 1963-03-14 | 1963-03-14 | Perfectionnements à la fabrication de l'acrylonitrile |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1468958A1 DE1468958A1 (de) | 1969-01-02 |
| DE1468958B2 true DE1468958B2 (de) | 1974-01-24 |
| DE1468958C3 DE1468958C3 (enrdf_load_stackoverflow) | 1974-08-15 |
Family
ID=8799240
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19641468958 Granted DE1468958B2 (de) | 1963-03-14 | 1964-03-03 | Verfahren zur Gewinnung von Acrylnitril und Acroleincyanhydrin |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE643943A (enrdf_load_stackoverflow) |
| DE (1) | DE1468958B2 (enrdf_load_stackoverflow) |
| FR (1) | FR1359316A (enrdf_load_stackoverflow) |
| IT (1) | IT716186A (enrdf_load_stackoverflow) |
| NL (1) | NL6402492A (enrdf_load_stackoverflow) |
-
0
- IT IT716186D patent/IT716186A/it unknown
-
1963
- 1963-03-14 FR FR927990A patent/FR1359316A/fr not_active Expired
-
1964
- 1964-02-18 BE BE643943D patent/BE643943A/xx unknown
- 1964-03-03 DE DE19641468958 patent/DE1468958B2/de active Granted
- 1964-03-11 NL NL6402492A patent/NL6402492A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE1468958A1 (de) | 1969-01-02 |
| BE643943A (enrdf_load_stackoverflow) | 1964-06-15 |
| DE1468958C3 (enrdf_load_stackoverflow) | 1974-08-15 |
| IT716186A (enrdf_load_stackoverflow) | |
| NL6402492A (enrdf_load_stackoverflow) | 1964-09-15 |
| FR1359316A (fr) | 1964-04-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| SH | Request for examination between 03.10.1968 and 22.04.1971 | ||
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| EHJ | Ceased/non-payment of the annual fee |