DE1543450A1 - Verfahren zur Reinigung von Acetonitril - Google Patents
Verfahren zur Reinigung von AcetonitrilInfo
- Publication number
- DE1543450A1 DE1543450A1 DE19661543450 DE1543450A DE1543450A1 DE 1543450 A1 DE1543450 A1 DE 1543450A1 DE 19661543450 DE19661543450 DE 19661543450 DE 1543450 A DE1543450 A DE 1543450A DE 1543450 A1 DE1543450 A1 DE 1543450A1
- Authority
- DE
- Germany
- Prior art keywords
- acetonitrile
- acrylonitrile
- mixture
- water
- column
- 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
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 title claims description 229
- 238000000034 method Methods 0.000 title claims description 16
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 57
- 239000000203 mixture Substances 0.000 claims description 37
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 29
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 20
- 229910021529 ammonia Inorganic materials 0.000 claims description 14
- 239000003054 catalyst Substances 0.000 claims description 10
- 238000009835 boiling Methods 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- 150000003138 primary alcohols Chemical class 0.000 claims description 3
- 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 claims description 2
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims 1
- 239000000908 ammonium hydroxide Substances 0.000 claims 1
- 238000004140 cleaning Methods 0.000 claims 1
- 238000004508 fractional distillation Methods 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
- 239000000047 product Substances 0.000 description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 238000004821 distillation Methods 0.000 description 11
- 150000002825 nitriles Chemical class 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 150000001298 alcohols Chemical class 0.000 description 5
- 239000003513 alkali Substances 0.000 description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 4
- 238000010533 azeotropic distillation Methods 0.000 description 4
- 238000007278 cyanoethylation reaction Methods 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- MXUPILKWZJJDFH-UHFFFAOYSA-N acetonitrile;prop-2-enenitrile Chemical compound CC#N.C=CC#N MXUPILKWZJJDFH-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000005219 aminonitrile group Chemical group 0.000 description 3
- 238000000895 extractive distillation Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 150000007960 acetonitrile Chemical class 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 238000007872 degassing Methods 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 150000004679 hydroxides Chemical class 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 125000002560 nitrile group Chemical group 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- -1 unsaturated aliphatic polyols Chemical class 0.000 description 2
- BCGCCTGNWPKXJL-UHFFFAOYSA-N 3-(2-cyanoethoxy)propanenitrile Chemical compound N#CCCOCCC#N BCGCCTGNWPKXJL-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000008362 aminopropionitriles Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000009286 beneficial effect Effects 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
- 239000006227 byproduct Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 210000001072 colon Anatomy 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-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
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
-
- 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)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR4649A FR1431919A (fr) | 1965-02-06 | 1965-02-06 | Perfectionnements à la purification de mélanges contenant de l'acétonitrile |
| FR21570A FR88407E (fr) | 1965-02-06 | 1965-06-21 | Perfectionnements à la purification de mélanges contenant de l'acétonitrile |
| FR41006A FR89253E (fr) | 1965-02-06 | 1965-12-06 | Perfectionnements à la purification de mélanges contenant de l'acétonitrile |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1543450A1 true DE1543450A1 (de) | 1969-09-11 |
Family
ID=27241900
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661543450 Pending DE1543450A1 (de) | 1965-02-06 | 1966-02-04 | Verfahren zur Reinigung von Acetonitril |
Country Status (6)
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4175053A (en) * | 1976-10-12 | 1979-11-20 | The Procter & Gamble Company | Base reactant |
| DE3011391A1 (de) * | 1979-03-28 | 1980-10-02 | Asahi Chemical Ind | Verfahren zur reinigung von rohem acetonitril |
| DE3334328A1 (de) * | 1983-09-22 | 1985-04-11 | Lentia GmbH Chem. u. pharm. Erzeugnisse - Industriebedarf, 8000 München | Verfahren zur vernichtung von gebundener blausaeure und acrylnitril in rohem acetonitril |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4287134A (en) | 1980-06-26 | 1981-09-01 | E. I. Du Pont De Nemours And Company | Purification of acetonitrile by caustic extraction |
| DE3437300A1 (de) * | 1984-10-11 | 1986-04-17 | Fritz 5882 Meinerzhagen Sträter | Konzepthalter zur anwendung an schreib-, zeichen-, bildschirmarbeitsplaetzen u.dgl. |
| CN105294494B (zh) * | 2015-12-05 | 2017-12-19 | 山东汇海医药化工有限公司 | 一种合成乙腈粗品氨气分离的方法 |
| US20230192600A1 (en) * | 2021-12-20 | 2023-06-22 | Ascend Performance Materials Operations Llc | Acetonitrile separation process |
-
1965
- 1965-02-06 FR FR4649A patent/FR1431919A/fr not_active Expired
- 1965-06-21 FR FR21570A patent/FR88407E/fr not_active Expired
- 1965-12-06 FR FR41006A patent/FR89253E/fr not_active Expired
-
1966
- 1966-01-27 LU LU50341A patent/LU50341A1/xx unknown
- 1966-02-03 NL NL6601375A patent/NL6601375A/xx unknown
- 1966-02-03 GB GB472566A patent/GB1088072A/en not_active Expired
- 1966-02-04 BE BE676043D patent/BE676043A/xx unknown
- 1966-02-04 DE DE19661543450 patent/DE1543450A1/de active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4175053A (en) * | 1976-10-12 | 1979-11-20 | The Procter & Gamble Company | Base reactant |
| DE3011391A1 (de) * | 1979-03-28 | 1980-10-02 | Asahi Chemical Ind | Verfahren zur reinigung von rohem acetonitril |
| DE3334328A1 (de) * | 1983-09-22 | 1985-04-11 | Lentia GmbH Chem. u. pharm. Erzeugnisse - Industriebedarf, 8000 München | Verfahren zur vernichtung von gebundener blausaeure und acrylnitril in rohem acetonitril |
Also Published As
| Publication number | Publication date |
|---|---|
| FR89253E (fr) | 1967-06-02 |
| FR1431919A (fr) | 1966-03-18 |
| BE676043A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1966-06-16 |
| FR88407E (fr) | 1967-02-03 |
| GB1088072A (en) | 1967-10-18 |
| LU50341A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1966-03-28 |
| NL6601375A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1966-08-08 |
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