EA004864B1 - Аммоксидирование смеси кетонов в ацетонитрил и цианид водорода - Google Patents
Аммоксидирование смеси кетонов в ацетонитрил и цианид водорода Download PDFInfo
- Publication number
- EA004864B1 EA004864B1 EA200101163A EA200101163A EA004864B1 EA 004864 B1 EA004864 B1 EA 004864B1 EA 200101163 A EA200101163 A EA 200101163A EA 200101163 A EA200101163 A EA 200101163A EA 004864 B1 EA004864 B1 EA 004864B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- acetonitrile
- ketones
- combinations
- ketone
- ammonia
- Prior art date
Links
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 title claims abstract description 140
- 150000002576 ketones Chemical class 0.000 title claims abstract description 75
- 239000000203 mixture Substances 0.000 title claims abstract description 35
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 title 1
- 229910052739 hydrogen Inorganic materials 0.000 title 1
- 239000001257 hydrogen Substances 0.000 title 1
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims abstract description 68
- 238000000034 method Methods 0.000 claims abstract description 57
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 50
- 239000003054 catalyst Substances 0.000 claims abstract description 41
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 38
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims abstract description 31
- 238000006243 chemical reaction Methods 0.000 claims abstract description 26
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 25
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 17
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 17
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 17
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 17
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 17
- 239000001301 oxygen Substances 0.000 claims abstract description 17
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims abstract description 16
- 238000004519 manufacturing process Methods 0.000 claims abstract description 14
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims abstract description 14
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims abstract description 14
- 239000001294 propane Substances 0.000 claims abstract description 8
- 229910052750 molybdenum Inorganic materials 0.000 claims abstract description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 5
- 229910052748 manganese Inorganic materials 0.000 claims abstract description 5
- 230000003647 oxidation Effects 0.000 claims abstract description 5
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 5
- 229910052720 vanadium Inorganic materials 0.000 claims abstract description 5
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims abstract description 4
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000006227 byproduct Substances 0.000 claims description 10
- 239000007789 gas Substances 0.000 claims description 6
- 238000011084 recovery Methods 0.000 claims description 6
- -1 C 4 ketones Chemical class 0.000 claims description 4
- 229910052684 Cerium Inorganic materials 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 3
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims 1
- 229910052804 chromium Inorganic materials 0.000 abstract description 5
- 229910052742 iron Inorganic materials 0.000 abstract 4
- 229910052718 tin Inorganic materials 0.000 abstract 4
- 229910052721 tungsten Inorganic materials 0.000 abstract 4
- 229910052770 Uranium Inorganic materials 0.000 abstract 2
- 229910052787 antimony Inorganic materials 0.000 abstract 2
- 229910052797 bismuth Inorganic materials 0.000 abstract 2
- 229910052796 boron Inorganic materials 0.000 abstract 2
- 229910052733 gallium Inorganic materials 0.000 abstract 2
- 229910052732 germanium Inorganic materials 0.000 abstract 2
- 229910052738 indium Inorganic materials 0.000 abstract 2
- 229910052759 nickel Inorganic materials 0.000 abstract 2
- 229910052758 niobium Inorganic materials 0.000 abstract 2
- 229910052698 phosphorus Inorganic materials 0.000 abstract 2
- 229910052715 tantalum Inorganic materials 0.000 abstract 2
- 229910052716 thallium Inorganic materials 0.000 abstract 2
- 229910052719 titanium Inorganic materials 0.000 abstract 2
- 229910052725 zinc Inorganic materials 0.000 abstract 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
- 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
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Natural products CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- MCMNRKCIXSYSNV-UHFFFAOYSA-N ZrO2 Inorganic materials O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| 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 |
|---|---|
| EA200101163A1 EA200101163A1 (ru) | 2002-12-26 |
| EA004864B1 true EA004864B1 (ru) | 2004-08-26 |
Family
ID=23248496
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EA200101163A EA004864B1 (ru) | 1999-05-27 | 2000-05-16 | Аммоксидирование смеси кетонов в ацетонитрил и цианид водорода |
Country Status (16)
| Country | Link |
|---|---|
| US (2) | US6413485B2 (enExample) |
| EP (2) | EP1181268B8 (enExample) |
| JP (1) | JP2003500468A (enExample) |
| KR (1) | KR100717551B1 (enExample) |
| CN (2) | CN1267347C (enExample) |
| AT (1) | ATE306468T1 (enExample) |
| AU (1) | AU5135900A (enExample) |
| BG (1) | BG65744B1 (enExample) |
| BR (1) | BR0010997A (enExample) |
| DE (1) | DE60023134T2 (enExample) |
| EA (1) | EA004864B1 (enExample) |
| ES (1) | ES2249271T3 (enExample) |
| RO (1) | RO120909B1 (enExample) |
| TR (1) | TR200103384T2 (enExample) |
| WO (1) | WO2000073261A1 (enExample) |
| ZA (1) | ZA200109165B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2451548C2 (ru) * | 2007-02-16 | 2012-05-27 | ИНЕОС ЮЭсЭй ЭлЭлСи | Способ окислительного аммонолиза пропана и изобутана в присутствии смешанных металлоксидных катализаторов |
Families Citing this family (6)
| 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 |
| 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 |
| CN108025922B (zh) * | 2015-07-22 | 2021-06-15 | 英威达纺织（英国）有限公司 | 来自丙烯腈共同制备的高纯度hcn |
| EP3744418A1 (en) | 2016-01-09 | 2020-12-02 | Ascend Performance Materials Operations LLC | Catalyst compositions and process for direct production of hydrogen cyanide in an acrylonitrile reactor feed stream |
Family Cites Families (13)
| 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 |
| DE1247277B (de) | 1963-09-19 | 1967-08-17 | Knapsack Ag | Verfahren zur Herstellung eines Oxyde des Vanadiums und Zinns enthaltenden Katalysators |
| GB1114898A (en) | 1964-08-17 | 1968-05-22 | Halcon International Inc | Production of aromatic nitriles and catalysts for use therefor |
| JPS5135400B2 (enExample) * | 1972-10-06 | 1976-10-01 | ||
| JPS5535377B2 (enExample) * | 1973-01-24 | 1980-09-12 | ||
| 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 |
| 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 |
| 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 EP EP00935980A patent/EP1181268B8/en not_active Expired - Lifetime
- 2000-05-16 EP EP04078068A patent/EP1520852A3/en not_active Withdrawn
- 2000-05-16 TR TR2001/03384T patent/TR200103384T2/xx unknown
- 2000-05-16 ES ES00935980T patent/ES2249271T3/es not_active Expired - Lifetime
- 2000-05-16 WO PCT/US2000/013374 patent/WO2000073261A1/en not_active Ceased
- 2000-05-16 DE DE60023134T patent/DE60023134T2/de not_active Expired - Lifetime
- 2000-05-16 CN CNB2004100957067A patent/CN1267347C/zh not_active Expired - Fee Related
- 2000-05-16 AU AU51359/00A patent/AU5135900A/en not_active Abandoned
- 2000-05-16 JP JP2000621328A patent/JP2003500468A/ja active Pending
- 2000-05-16 BR BR0010997-5A patent/BR0010997A/pt not_active Application Discontinuation
- 2000-05-16 RO ROA200101268A patent/RO120909B1/ro unknown
- 2000-05-16 CN CNB008079978A patent/CN1243726C/zh not_active Expired - Fee Related
- 2000-05-16 EA EA200101163A patent/EA004864B1/ru not_active IP Right Cessation
- 2000-05-16 KR KR1020017015230A patent/KR100717551B1/ko not_active Expired - Fee Related
- 2000-05-16 AT AT00935980T patent/ATE306468T1/de not_active IP Right Cessation
-
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
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2451548C2 (ru) * | 2007-02-16 | 2012-05-27 | ИНЕОС ЮЭсЭй ЭлЭлСи | Способ окислительного аммонолиза пропана и изобутана в присутствии смешанных металлоксидных катализаторов |
Also Published As
| Publication number | Publication date |
|---|---|
| DE60023134T2 (de) | 2006-04-13 |
| KR20020003572A (ko) | 2002-01-12 |
| KR100717551B1 (ko) | 2007-05-15 |
| RO120909B1 (ro) | 2006-09-29 |
| JP2003500468A (ja) | 2003-01-07 |
| US20020004027A1 (en) | 2002-01-10 |
| CN1267347C (zh) | 2006-08-02 |
| AU5135900A (en) | 2000-12-18 |
| ZA200109165B (en) | 2003-02-06 |
| US6667020B2 (en) | 2003-12-23 |
| EP1181268A1 (en) | 2002-02-27 |
| EP1181268B1 (en) | 2005-10-12 |
| BG65744B1 (bg) | 2009-09-30 |
| EP1181268B8 (en) | 2005-12-14 |
| US6413485B2 (en) | 2002-07-02 |
| EP1520852A2 (en) | 2005-04-06 |
| ATE306468T1 (de) | 2005-10-15 |
| WO2000073261A1 (en) | 2000-12-07 |
| CN1629072A (zh) | 2005-06-22 |
| BR0010997A (pt) | 2002-02-19 |
| US20030198586A1 (en) | 2003-10-23 |
| CN1243726C (zh) | 2006-03-01 |
| EA200101163A1 (ru) | 2002-12-26 |
| CN1351586A (zh) | 2002-05-29 |
| EP1520852A3 (en) | 2005-09-21 |
| BG106099A (en) | 2002-06-28 |
| WO2000073261A9 (en) | 2002-06-27 |
| TR200103384T2 (tr) | 2002-04-22 |
| ES2249271T3 (es) | 2006-04-01 |
| DE60023134D1 (de) | 2006-02-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Lapse of a eurasian patent due to non-payment of renewal fees within the time limit in the following designated state(s) |
Designated state(s): AM AZ KZ KG MD TJ TM |
|
| PC4A | Registration of transfer of a eurasian patent by assignment | ||
| MM4A | Lapse of a eurasian patent due to non-payment of renewal fees within the time limit in the following designated state(s) |
Designated state(s): BY |
|
| MM4A | Lapse of a eurasian patent due to non-payment of renewal fees within the time limit in the following designated state(s) |
Designated state(s): RU |