JP2003500468A - アセトニトリル及びシアン化水素へのケトン類混合物のアンモ酸化 - Google Patents
アセトニトリル及びシアン化水素へのケトン類混合物のアンモ酸化Info
- Publication number
- JP2003500468A JP2003500468A JP2000621328A JP2000621328A JP2003500468A JP 2003500468 A JP2003500468 A JP 2003500468A JP 2000621328 A JP2000621328 A JP 2000621328A JP 2000621328 A JP2000621328 A JP 2000621328A JP 2003500468 A JP2003500468 A JP 2003500468A
- Authority
- JP
- Japan
- Prior art keywords
- acetonitrile
- ketones
- ketone
- hydrogen cyanide
- combinations
- 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 abstract description 114
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 title claims abstract description 62
- 150000002576 ketones Chemical class 0.000 title claims abstract description 54
- 239000000203 mixture Substances 0.000 title claims abstract description 27
- 238000000034 method Methods 0.000 claims abstract description 44
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 38
- 239000003054 catalyst Substances 0.000 claims abstract description 29
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims abstract description 27
- 238000006243 chemical reaction Methods 0.000 claims abstract description 21
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 19
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims abstract description 14
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 14
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 14
- 238000004519 manufacturing process Methods 0.000 claims abstract description 13
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims abstract description 13
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims abstract description 13
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 10
- 239000001301 oxygen Substances 0.000 claims abstract description 10
- 239000001294 propane Substances 0.000 claims abstract description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 31
- 239000006227 byproduct Substances 0.000 claims description 10
- 239000002994 raw material Substances 0.000 claims description 10
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 8
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 8
- 229910052742 iron Inorganic materials 0.000 claims description 8
- 229910052804 chromium Inorganic materials 0.000 claims description 7
- 229910052718 tin Inorganic materials 0.000 claims description 7
- -1 C 4 ketones Chemical class 0.000 claims description 6
- 229910052721 tungsten Inorganic materials 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 229910052750 molybdenum Inorganic materials 0.000 claims description 4
- 229910052759 nickel Inorganic materials 0.000 claims description 4
- 229910052719 titanium Inorganic materials 0.000 claims description 4
- 229910052720 vanadium Inorganic materials 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 229910052770 Uranium Inorganic materials 0.000 claims description 3
- 229910052787 antimony Inorganic materials 0.000 claims description 3
- 229910052797 bismuth Inorganic materials 0.000 claims description 3
- 229910052796 boron Inorganic materials 0.000 claims description 3
- 229910052733 gallium Inorganic materials 0.000 claims description 3
- 229910052732 germanium Inorganic materials 0.000 claims description 3
- 229910052738 indium Inorganic materials 0.000 claims description 3
- 229910052748 manganese Inorganic materials 0.000 claims description 3
- 230000003647 oxidation Effects 0.000 claims description 3
- 238000007254 oxidation reaction Methods 0.000 claims description 3
- 229910052715 tantalum Inorganic materials 0.000 claims description 3
- 229910052716 thallium Inorganic materials 0.000 claims description 3
- 229910052725 zinc Inorganic materials 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 238000010791 quenching Methods 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 3
- 150000002825 nitriles Chemical class 0.000 description 3
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Natural products CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 101100214868 Autographa californica nuclear polyhedrosis virus AC54 gene Proteins 0.000 description 1
- 102100024522 Bladder cancer-associated protein Human genes 0.000 description 1
- 101150110835 Blcap gene Proteins 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- 101100493740 Oryza sativa subsp. japonica BC10 gene Proteins 0.000 description 1
- 101100219325 Phaseolus vulgaris BA13 gene Proteins 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 230000003466 anti-cipated effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910052758 niobium Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 231100000989 no adverse effect Toxicity 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/24—Preparation of carboxylic acid nitriles by ammoxidation of hydrocarbons or substituted hydrocarbons
- C07C253/26—Preparation of carboxylic acid nitriles by ammoxidation of hydrocarbons or substituted hydrocarbons containing carbon-to-carbon multiple bonds, e.g. unsaturated aldehydes
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01C—AMMONIA; CYANOGEN; COMPOUNDS THEREOF
- C01C3/00—Cyanogen; Compounds thereof
- C01C3/02—Preparation, separation or purification of hydrogen cyanide
- C01C3/0208—Preparation in gaseous phase
- C01C3/0212—Preparation in gaseous phase from hydrocarbons and ammonia in the presence of oxygen, e.g. the Andrussow-process
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01C—AMMONIA; CYANOGEN; COMPOUNDS THEREOF
- C01C3/00—Cyanogen; Compounds thereof
- C01C3/02—Preparation, separation or purification of hydrogen cyanide
- C01C3/0208—Preparation in gaseous phase
- C01C3/0212—Preparation in gaseous phase from hydrocarbons and ammonia in the presence of oxygen, e.g. the Andrussow-process
- C01C3/022—Apparatus therefor
- C01C3/0225—Apparatus therefor characterised by the synthesis reactor
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/24—Preparation of carboxylic acid nitriles by ammoxidation of hydrocarbons or substituted hydrocarbons
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/320,937 | 1999-05-27 | ||
| US09/320,937 US6413485B2 (en) | 1999-05-27 | 1999-05-27 | Ammoxidation of a mixture of ketones to acetonitrile and HCN |
| PCT/US2000/013374 WO2000073261A1 (en) | 1999-05-27 | 2000-05-16 | Ammoxidation of a mixture of ketones to acetonitrile and hydrogen cyanide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2003500468A true JP2003500468A (ja) | 2003-01-07 |
| JP2003500468A5 JP2003500468A5 (https=) | 2007-06-28 |
Family
ID=23248496
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000621328A Pending JP2003500468A (ja) | 1999-05-27 | 2000-05-16 | アセトニトリル及びシアン化水素へのケトン類混合物のアンモ酸化 |
Country Status (16)
| Country | Link |
|---|---|
| US (2) | US6413485B2 (https=) |
| EP (2) | EP1181268B8 (https=) |
| JP (1) | JP2003500468A (https=) |
| KR (1) | KR100717551B1 (https=) |
| CN (2) | CN1267347C (https=) |
| AT (1) | ATE306468T1 (https=) |
| AU (1) | AU5135900A (https=) |
| BG (1) | BG65744B1 (https=) |
| BR (1) | BR0010997A (https=) |
| DE (1) | DE60023134T2 (https=) |
| EA (1) | EA004864B1 (https=) |
| ES (1) | ES2249271T3 (https=) |
| RO (1) | RO120909B1 (https=) |
| TR (1) | TR200103384T2 (https=) |
| WO (1) | WO2000073261A1 (https=) |
| ZA (1) | ZA200109165B (https=) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4854151B2 (ja) * | 2001-08-29 | 2012-01-18 | 旭化成ケミカルズ株式会社 | アセトニトリル及び青酸を安定に増産する方法 |
| US6982342B2 (en) * | 2002-05-16 | 2006-01-03 | Standard Oil Company | Ammoxidation of carboxylic acids to a mixture of nitriles |
| RU2451548C2 (ru) * | 2007-02-16 | 2012-05-27 | ИНЕОС ЮЭсЭй ЭлЭлСи | Способ окислительного аммонолиза пропана и изобутана в присутствии смешанных металлоксидных катализаторов |
| US8585870B2 (en) * | 2008-03-05 | 2013-11-19 | E I Du Pont De Nemours And Company | Process to C-manufacture acrylonitrile and hydrogen cyanide |
| CN104724725B (zh) * | 2014-11-21 | 2017-05-24 | 重庆紫光化工股份有限公司 | 氢氰酸气体分离纯化系统及方法 |
| WO2017015521A1 (en) * | 2015-07-22 | 2017-01-26 | Invista North America S.A R.L. | High purity hcn from acrylonitrile co-production |
| JP6905531B2 (ja) | 2016-01-09 | 2021-07-21 | アセンド・パフォーマンス・マテリアルズ・オペレーションズ・リミテッド・ライアビリティ・カンパニーＡｓｃｅｎｄ Ｐｅｒｆｏｒｍａｎｃｅ Ｍａｔｅｒｉａｌｓ Ｏｐｅｒａｔｉｏｎｓ Ｌｌｃ | アクリロニトリル反応器供給物流れでのシアン化水素の直接生成のための触媒組成物および方法 |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1041980A (en) * | 1963-09-19 | 1966-09-07 | Knapsack Ag | Process for the manufacture of a catalyst containing vanadium and tin oxides |
| GB1114898A (en) * | 1964-08-17 | 1968-05-22 | Halcon International Inc | Production of aromatic nitriles and catalysts for use therefor |
| JPS4958100A (https=) * | 1972-10-06 | 1974-06-05 | ||
| JPS4995922A (https=) * | 1973-01-24 | 1974-09-11 | ||
| JPH03246269A (ja) * | 1990-02-21 | 1991-11-01 | Asahi Chem Ind Co Ltd | アセトニトリルの増収方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2006981A (en) * | 1931-12-14 | 1935-07-02 | Ig Farbenindustrie Ag | Production of hydrocyanic acid |
| US3106574A (en) * | 1960-12-19 | 1963-10-08 | Standard Oil Co | Method for the manufacture of acetonitrile |
| US4272451A (en) | 1979-12-26 | 1981-06-09 | Monsanto Company | Acetonitrile process with improved catalysts |
| CH642942A5 (en) | 1980-04-16 | 1984-05-15 | Lonza Ag | Process for the preparation of acetonitrile |
| CA1320735C (en) * | 1987-11-24 | 1993-07-27 | Ramakrishnan Ramachandran | Process for the production of nitriles and anhydrides |
| US5204079A (en) * | 1991-02-15 | 1993-04-20 | Standard Oil Company | HCN by catalytic ammoxidation of crude acetonitrile |
| US5466857A (en) * | 1994-08-10 | 1995-11-14 | The Standard Oil Company | Process for reduction of waste material during manufacture of acrylonitrile |
| UA54409C2 (uk) * | 1997-07-16 | 2003-03-17 | Асахі Касеі Кабусікі Кайся | Спосіб одержання акрилонітрилу або метакрилонітрилу з пропану або ізобутану шляхом амоксидування |
-
1999
- 1999-05-27 US US09/320,937 patent/US6413485B2/en not_active Expired - Fee Related
-
2000
- 2000-05-16 ES ES00935980T patent/ES2249271T3/es not_active Expired - Lifetime
- 2000-05-16 CN CNB2004100957067A patent/CN1267347C/zh not_active Expired - Fee Related
- 2000-05-16 EP EP00935980A patent/EP1181268B8/en not_active Expired - Lifetime
- 2000-05-16 CN CNB008079978A patent/CN1243726C/zh not_active Expired - Fee Related
- 2000-05-16 BR BR0010997-5A patent/BR0010997A/pt not_active Application Discontinuation
- 2000-05-16 JP JP2000621328A patent/JP2003500468A/ja active Pending
- 2000-05-16 AU AU51359/00A patent/AU5135900A/en not_active Abandoned
- 2000-05-16 DE DE60023134T patent/DE60023134T2/de not_active Expired - Lifetime
- 2000-05-16 EA EA200101163A patent/EA004864B1/ru not_active IP Right Cessation
- 2000-05-16 TR TR2001/03384T patent/TR200103384T2/xx unknown
- 2000-05-16 AT AT00935980T patent/ATE306468T1/de not_active IP Right Cessation
- 2000-05-16 WO PCT/US2000/013374 patent/WO2000073261A1/en not_active Ceased
- 2000-05-16 RO ROA200101268A patent/RO120909B1/ro unknown
- 2000-05-16 EP EP04078068A patent/EP1520852A3/en not_active Withdrawn
- 2000-05-16 KR KR1020017015230A patent/KR100717551B1/ko not_active Expired - Fee Related
-
2001
- 2001-11-06 ZA ZA200109165A patent/ZA200109165B/en unknown
- 2001-11-09 BG BG106099A patent/BG65744B1/bg unknown
- 2001-12-10 US US10/016,703 patent/US6667020B2/en not_active Expired - Fee Related
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1041980A (en) * | 1963-09-19 | 1966-09-07 | Knapsack Ag | Process for the manufacture of a catalyst containing vanadium and tin oxides |
| GB1114898A (en) * | 1964-08-17 | 1968-05-22 | Halcon International Inc | Production of aromatic nitriles and catalysts for use therefor |
| JPS4958100A (https=) * | 1972-10-06 | 1974-06-05 | ||
| JPS4995922A (https=) * | 1973-01-24 | 1974-09-11 | ||
| JPH03246269A (ja) * | 1990-02-21 | 1991-11-01 | Asahi Chem Ind Co Ltd | アセトニトリルの増収方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| ES2249271T3 (es) | 2006-04-01 |
| EP1181268B1 (en) | 2005-10-12 |
| EP1181268B8 (en) | 2005-12-14 |
| US20020004027A1 (en) | 2002-01-10 |
| CN1243726C (zh) | 2006-03-01 |
| CN1351586A (zh) | 2002-05-29 |
| US6413485B2 (en) | 2002-07-02 |
| KR100717551B1 (ko) | 2007-05-15 |
| CN1629072A (zh) | 2005-06-22 |
| EP1520852A3 (en) | 2005-09-21 |
| DE60023134D1 (de) | 2006-02-23 |
| BG65744B1 (bg) | 2009-09-30 |
| WO2000073261A1 (en) | 2000-12-07 |
| TR200103384T2 (tr) | 2002-04-22 |
| EP1520852A2 (en) | 2005-04-06 |
| US6667020B2 (en) | 2003-12-23 |
| EA200101163A1 (ru) | 2002-12-26 |
| WO2000073261A9 (en) | 2002-06-27 |
| KR20020003572A (ko) | 2002-01-12 |
| EA004864B1 (ru) | 2004-08-26 |
| RO120909B1 (ro) | 2006-09-29 |
| EP1181268A1 (en) | 2002-02-27 |
| BR0010997A (pt) | 2002-02-19 |
| US20030198586A1 (en) | 2003-10-23 |
| AU5135900A (en) | 2000-12-18 |
| DE60023134T2 (de) | 2006-04-13 |
| BG106099A (en) | 2002-06-28 |
| ATE306468T1 (de) | 2005-10-15 |
| ZA200109165B (en) | 2003-02-06 |
| CN1267347C (zh) | 2006-08-02 |
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