DE19918246A1 - Verfahren zur Herstellung von Acetoncyanhydrin - Google Patents
Verfahren zur Herstellung von AcetoncyanhydrinInfo
- Publication number
- DE19918246A1 DE19918246A1 DE19918246A DE19918246A DE19918246A1 DE 19918246 A1 DE19918246 A1 DE 19918246A1 DE 19918246 A DE19918246 A DE 19918246A DE 19918246 A DE19918246 A DE 19918246A DE 19918246 A1 DE19918246 A1 DE 19918246A1
- Authority
- DE
- Germany
- Prior art keywords
- gas
- acetone
- hydrogen cyanide
- acetone cyanohydrin
- reactor
- 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.)
- Withdrawn
Links
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 title claims abstract description 137
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 title claims abstract description 86
- 239000007789 gas Substances 0.000 title claims abstract description 83
- MWFMGBPGAXYFAR-UHFFFAOYSA-N 2-hydroxy-2-methylpropanenitrile Chemical compound CC(C)(O)C#N MWFMGBPGAXYFAR-UHFFFAOYSA-N 0.000 title claims abstract description 66
- 238000010924 continuous production Methods 0.000 title claims abstract description 6
- 238000005201 scrubbing Methods 0.000 title claims abstract description 5
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 title 1
- 238000004064 recycling Methods 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 33
- 239000007788 liquid Substances 0.000 claims abstract description 27
- 238000006243 chemical reaction Methods 0.000 claims abstract description 23
- 239000003054 catalyst Substances 0.000 claims abstract description 21
- 239000000203 mixture Substances 0.000 claims abstract description 19
- 239000012071 phase Substances 0.000 claims abstract description 19
- 239000007791 liquid phase Substances 0.000 claims abstract description 15
- 239000011261 inert gas Substances 0.000 claims abstract description 14
- 239000002904 solvent Substances 0.000 claims abstract description 9
- 238000009835 boiling Methods 0.000 claims abstract description 8
- 238000004821 distillation Methods 0.000 claims abstract description 7
- 238000005406 washing Methods 0.000 claims description 20
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 9
- 238000006189 Andrussov oxidation reaction Methods 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 4
- 239000000470 constituent Substances 0.000 claims description 2
- 239000007792 gaseous phase Substances 0.000 claims 2
- 238000003541 multi-stage reaction Methods 0.000 claims 2
- 230000007423 decrease Effects 0.000 claims 1
- 239000003039 volatile agent Substances 0.000 abstract 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 14
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 7
- 229910021529 ammonia Inorganic materials 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 230000006641 stabilisation Effects 0.000 description 4
- 238000011105 stabilization Methods 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 238000007883 cyanide addition reaction Methods 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- 241001503485 Mammuthus Species 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 229910052601 baryte Inorganic materials 0.000 description 2
- 239000010428 baryte Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000000571 coke Substances 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 238000012856 packing Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- RZRSTWQDXDNYOV-UHFFFAOYSA-N 2-hydroxy-2-methylpropanenitrile;sulfuric acid Chemical compound OS(O)(=O)=O.CC(C)(O)C#N RZRSTWQDXDNYOV-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical class CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003957 anion exchange resin Substances 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000010960 commercial process Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000007700 distillative separation Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- MUQBUKGCVPYANP-UHFFFAOYSA-N formonitrile Chemical compound N#C.N#C MUQBUKGCVPYANP-UHFFFAOYSA-N 0.000 description 1
- ZPWPULVVKGZHJU-UHFFFAOYSA-N formonitrile 2-hydroxy-2-methylpropanenitrile Chemical compound CC(C#N)(O)C.C#N ZPWPULVVKGZHJU-UHFFFAOYSA-N 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 239000002912 waste gas Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19918246A DE19918246A1 (de) | 1999-04-22 | 1999-04-22 | Verfahren zur Herstellung von Acetoncyanhydrin |
| EP00926732A EP1171420B1 (de) | 1999-04-22 | 2000-03-08 | Verfahren zur herstellung von acetoncyanhydrin |
| AT00926732T ATE247631T1 (de) | 1999-04-22 | 2000-03-08 | Verfahren zur herstellung von acetoncyanhydrin |
| PCT/EP2000/002014 WO2000064861A2 (de) | 1999-04-22 | 2000-03-08 | Verfahren zur herstellung von acetoncyanhydrin |
| DE50003363T DE50003363D1 (de) | 1999-04-22 | 2000-03-08 | Verfahren zur herstellung von acetoncyanhydrin |
| JP2000613814A JP2002543056A (ja) | 1999-04-22 | 2000-03-08 | アセトンシアンヒドリンの製法 |
| AU45385/00A AU4538500A (en) | 1999-04-22 | 2000-03-08 | Method of producing acetone-cyanhydrin |
| US09/959,271 US6417385B1 (en) | 1999-04-22 | 2000-03-08 | Method of producing acetone-cyanhydrin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19918246A DE19918246A1 (de) | 1999-04-22 | 1999-04-22 | Verfahren zur Herstellung von Acetoncyanhydrin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE19918246A1 true DE19918246A1 (de) | 2000-10-26 |
Family
ID=7905469
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19918246A Withdrawn DE19918246A1 (de) | 1999-04-22 | 1999-04-22 | Verfahren zur Herstellung von Acetoncyanhydrin |
| DE50003363T Expired - Lifetime DE50003363D1 (de) | 1999-04-22 | 2000-03-08 | Verfahren zur herstellung von acetoncyanhydrin |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE50003363T Expired - Lifetime DE50003363D1 (de) | 1999-04-22 | 2000-03-08 | Verfahren zur herstellung von acetoncyanhydrin |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US6417385B1 (enExample) |
| EP (1) | EP1171420B1 (enExample) |
| JP (1) | JP2002543056A (enExample) |
| AT (1) | ATE247631T1 (enExample) |
| AU (1) | AU4538500A (enExample) |
| DE (2) | DE19918246A1 (enExample) |
| WO (1) | WO2000064861A2 (enExample) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102006058250A1 (de) * | 2006-12-08 | 2008-06-12 | Evonik Röhm Gmbh | Integriertes Verfahren und Vorrichtung zur Herstellung von Methacrylsäureestern aus Aceton und Blausäure |
| DE102006058249A1 (de) * | 2006-12-08 | 2008-06-12 | Evonik Röhm Gmbh | Verfahren zur Herstellung von Cyanhydrinen sowie deren Verwendung bei der Herstellung von Methacrylsäurealkylestern |
| DE102006059512A1 (de) * | 2006-12-14 | 2008-06-19 | Evonik Röhm Gmbh | Destillative Aufarbeitung von Acetoncyanhydrin und Verfahren zur Herstellung von Metharcylsäureesther und Nachfolgeprodukten |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2003204521A1 (en) * | 2002-06-14 | 2004-01-15 | Rohm And Haas Company | Improved process for producing acetone cyanohydrin |
| FR2931477B1 (fr) * | 2008-05-21 | 2012-08-17 | Arkema France | Acide cyanhydrique derive de matiere premiere renouvable |
| FR2931822B1 (fr) * | 2008-05-30 | 2012-11-02 | Arkema France | Methacrylate de methyle derive de la biomasse, procede de fabrication, utilisations et polymeres correspondants. |
| WO2012113665A1 (de) * | 2011-02-23 | 2012-08-30 | Evonik Degussa Gmbh | Lagerstabiles 2-hydroxy-4-(methylthio)buttersäurenitril |
| DE102011076642A1 (de) | 2011-05-27 | 2012-11-29 | Evonik Röhm Gmbh | Verfahren zur Herstellung von Methacrylsäure |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1257765B (de) | 1960-10-29 | 1968-01-04 | Degussa | Verfahren zur Herstellung von Acetoncyanhydrin |
| US3700718A (en) | 1969-11-24 | 1972-10-24 | Sumitomo Chemical Co | Method for continuous production of pure acetone cyanohydrin |
| DE3933207A1 (de) | 1989-10-05 | 1991-04-18 | Degussa | Verfahren zur reinigung von roh-cyanhydrinen mit 3 bis 6 kohlenstoffatomen |
-
1999
- 1999-04-22 DE DE19918246A patent/DE19918246A1/de not_active Withdrawn
-
2000
- 2000-03-08 AT AT00926732T patent/ATE247631T1/de not_active IP Right Cessation
- 2000-03-08 DE DE50003363T patent/DE50003363D1/de not_active Expired - Lifetime
- 2000-03-08 EP EP00926732A patent/EP1171420B1/de not_active Expired - Lifetime
- 2000-03-08 US US09/959,271 patent/US6417385B1/en not_active Expired - Lifetime
- 2000-03-08 WO PCT/EP2000/002014 patent/WO2000064861A2/de not_active Ceased
- 2000-03-08 AU AU45385/00A patent/AU4538500A/en not_active Abandoned
- 2000-03-08 JP JP2000613814A patent/JP2002543056A/ja active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102006058250A1 (de) * | 2006-12-08 | 2008-06-12 | Evonik Röhm Gmbh | Integriertes Verfahren und Vorrichtung zur Herstellung von Methacrylsäureestern aus Aceton und Blausäure |
| DE102006058249A1 (de) * | 2006-12-08 | 2008-06-12 | Evonik Röhm Gmbh | Verfahren zur Herstellung von Cyanhydrinen sowie deren Verwendung bei der Herstellung von Methacrylsäurealkylestern |
| DE102006059512A1 (de) * | 2006-12-14 | 2008-06-19 | Evonik Röhm Gmbh | Destillative Aufarbeitung von Acetoncyanhydrin und Verfahren zur Herstellung von Metharcylsäureesther und Nachfolgeprodukten |
| US8143434B2 (en) | 2006-12-14 | 2012-03-27 | Evonik Röhm Gmbh | Production by distillation of acetone cyanhydrin and method for producing methacrylic ester and subsequent products |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2000064861A2 (de) | 2000-11-02 |
| AU4538500A (en) | 2000-11-10 |
| ATE247631T1 (de) | 2003-09-15 |
| DE50003363D1 (de) | 2003-09-25 |
| WO2000064861A3 (de) | 2001-05-03 |
| EP1171420A2 (de) | 2002-01-16 |
| EP1171420B1 (de) | 2003-08-20 |
| US6417385B1 (en) | 2002-07-09 |
| JP2002543056A (ja) | 2002-12-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8127 | New person/name/address of the applicant |
Owner name: DEGUSSA AG, 40474 DUESSELDORF, DE |
|
| 8139 | Disposal/non-payment of the annual fee |