JP2002543056A - アセトンシアンヒドリンの製法 - Google Patents
アセトンシアンヒドリンの製法Info
- Publication number
- JP2002543056A JP2002543056A JP2000613814A JP2000613814A JP2002543056A JP 2002543056 A JP2002543056 A JP 2002543056A JP 2000613814 A JP2000613814 A JP 2000613814A JP 2000613814 A JP2000613814 A JP 2000613814A JP 2002543056 A JP2002543056 A JP 2002543056A
- Authority
- JP
- Japan
- Prior art keywords
- gas
- acetone
- acetone cyanohydrin
- hydrogen cyanide
- liquid
- 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
- MWFMGBPGAXYFAR-UHFFFAOYSA-N 2-hydroxy-2-methylpropanenitrile Chemical compound CC(C)(O)C#N MWFMGBPGAXYFAR-UHFFFAOYSA-N 0.000 title claims abstract description 50
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims abstract description 134
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 82
- 239000007789 gas Substances 0.000 claims abstract description 79
- 238000000034 method Methods 0.000 claims abstract description 36
- 239000007788 liquid Substances 0.000 claims abstract description 24
- 239000002904 solvent Substances 0.000 claims abstract description 8
- 238000009835 boiling Methods 0.000 claims abstract description 7
- 238000006243 chemical reaction Methods 0.000 claims description 29
- 239000003054 catalyst Substances 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 17
- 239000012071 phase Substances 0.000 claims description 17
- 238000005406 washing Methods 0.000 claims description 16
- 239000011261 inert gas Substances 0.000 claims description 12
- 239000007791 liquid phase Substances 0.000 claims description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
- 238000004821 distillation Methods 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 4
- 238000010924 continuous production Methods 0.000 claims description 4
- 238000000926 separation method Methods 0.000 claims description 4
- 238000006189 Andrussov oxidation reaction Methods 0.000 claims description 3
- 238000003541 multi-stage reaction Methods 0.000 claims 2
- 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 12
- 239000002912 waste gas Substances 0.000 description 8
- 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
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 238000004140 cleaning Methods 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
- 230000015572 biosynthetic process Effects 0.000 description 5
- WOFDVDFSGLBFAC-UHFFFAOYSA-N lactonitrile Chemical compound CC(O)C#N WOFDVDFSGLBFAC-UHFFFAOYSA-N 0.000 description 4
- 238000012856 packing Methods 0.000 description 4
- 230000006641 stabilisation Effects 0.000 description 4
- 238000011105 stabilization Methods 0.000 description 4
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 238000005201 scrubbing Methods 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- 238000010626 work up procedure Methods 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 2
- 229910001863 barium hydroxide Inorganic materials 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 239000000571 coke Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 235000011118 potassium hydroxide Nutrition 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- WSGYTJNNHPZFKR-UHFFFAOYSA-N 3-hydroxypropanenitrile Chemical compound OCCC#N WSGYTJNNHPZFKR-UHFFFAOYSA-N 0.000 description 1
- 101100000419 Autographa californica nuclear polyhedrosis virus AC41 gene Proteins 0.000 description 1
- 101100214868 Autographa californica nuclear polyhedrosis virus AC54 gene Proteins 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241001529455 Mammut Species 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
- 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
- 239000001166 ammonium sulphate Substances 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000010960 commercial process Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000007700 distillative separation Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000002474 experimental method Methods 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
- 239000001257 hydrogen Substances 0.000 description 1
- 238000007726 management method Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- KQSVYGBEQZFKKN-UHFFFAOYSA-N propan-2-one cyanide Chemical compound [C-]#N.CC(=O)C KQSVYGBEQZFKKN-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000012495 reaction gas Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003786 synthesis reaction 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
- 238000011144 upstream manufacturing Methods 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)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19918246.9 | 1999-04-22 | ||
| DE19918246A DE19918246A1 (de) | 1999-04-22 | 1999-04-22 | Verfahren zur Herstellung von Acetoncyanhydrin |
| PCT/EP2000/002014 WO2000064861A2 (de) | 1999-04-22 | 2000-03-08 | Verfahren zur herstellung von acetoncyanhydrin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2002543056A true JP2002543056A (ja) | 2002-12-17 |
| JP2002543056A5 JP2002543056A5 (enExample) | 2007-04-26 |
Family
ID=7905469
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000613814A Pending JP2002543056A (ja) | 1999-04-22 | 2000-03-08 | アセトンシアンヒドリンの製法 |
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 |
|---|---|---|---|---|
| JP2010511652A (ja) * | 2006-12-08 | 2010-04-15 | エボニック レーム ゲゼルシャフト ミット ベシュレンクテル ハフツング | シアンヒドリンの製造方法並びにメタクリル酸アルキルエステルの製造におけるその使用 |
| JP2011521872A (ja) * | 2008-05-21 | 2011-07-28 | アルケマ フランス | バイオ資源炭素を含むシアン化水素酸 |
| JP2014513669A (ja) * | 2011-02-23 | 2014-06-05 | エボニック デグサ ゲーエムベーハー | 貯蔵安定性の２‐ヒドロキシ‐４‐（メチルチオ）酪酸ニトリル |
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 |
| DE102006058250A1 (de) * | 2006-12-08 | 2008-06-12 | Evonik Röhm Gmbh | Integriertes Verfahren und Vorrichtung zur Herstellung von Methacrylsäureestern aus Aceton und Blausäure |
| DE102006059512A1 (de) | 2006-12-14 | 2008-06-19 | Evonik Röhm Gmbh | Destillative Aufarbeitung von Acetoncyanhydrin und Verfahren zur Herstellung von Metharcylsäureesther und Nachfolgeprodukten |
| FR2931822B1 (fr) * | 2008-05-30 | 2012-11-02 | Arkema France | Methacrylate de methyle derive de la biomasse, procede de fabrication, utilisations et polymeres correspondants. |
| 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 (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010511652A (ja) * | 2006-12-08 | 2010-04-15 | エボニック レーム ゲゼルシャフト ミット ベシュレンクテル ハフツング | シアンヒドリンの製造方法並びにメタクリル酸アルキルエステルの製造におけるその使用 |
| JP2011521872A (ja) * | 2008-05-21 | 2011-07-28 | アルケマ フランス | バイオ資源炭素を含むシアン化水素酸 |
| JP2015096467A (ja) * | 2008-05-21 | 2015-05-21 | アルケマ フランス | バイオ資源炭素を含むシアン化水素酸 |
| JP2017039643A (ja) * | 2008-05-21 | 2017-02-23 | アルケマ フランス | バイオ資源炭素を含むシアン化水素酸 |
| JP2014513669A (ja) * | 2011-02-23 | 2014-06-05 | エボニック デグサ ゲーエムベーハー | 貯蔵安定性の２‐ヒドロキシ‐４‐（メチルチオ）酪酸ニトリル |
Also Published As
| Publication number | Publication date |
|---|---|
| DE19918246A1 (de) | 2000-10-26 |
| 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 |
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