JP4418364B2 - ニトリル類の混合物へのカルボン酸のアンモ酸化 - Google Patents
ニトリル類の混合物へのカルボン酸のアンモ酸化 Download PDFInfo
- Publication number
- JP4418364B2 JP4418364B2 JP2004505316A JP2004505316A JP4418364B2 JP 4418364 B2 JP4418364 B2 JP 4418364B2 JP 2004505316 A JP2004505316 A JP 2004505316A JP 2004505316 A JP2004505316 A JP 2004505316A JP 4418364 B2 JP4418364 B2 JP 4418364B2
- Authority
- JP
- Japan
- Prior art keywords
- carboxylic acid
- ammoxidation
- acid
- acrylonitrile
- acetonitrile
- 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.)
- Expired - Lifetime
Links
- 150000001735 carboxylic acids Chemical class 0.000 title claims description 91
- 239000000203 mixture Substances 0.000 title claims description 31
- 150000002825 nitriles Chemical class 0.000 title description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims abstract description 96
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 56
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims abstract description 38
- 238000000034 method Methods 0.000 claims abstract description 33
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 28
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims abstract description 28
- 238000006243 chemical reaction Methods 0.000 claims abstract description 26
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims abstract description 24
- 239000003054 catalyst Substances 0.000 claims abstract description 24
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 18
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 18
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims abstract description 17
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims abstract description 17
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 15
- 239000001294 propane Substances 0.000 claims abstract description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 75
- 238000010791 quenching Methods 0.000 claims description 32
- 235000011054 acetic acid Nutrition 0.000 claims description 22
- 239000007788 liquid Substances 0.000 claims description 22
- 150000003863 ammonium salts Chemical class 0.000 claims description 13
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 12
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 12
- 229910001882 dioxygen Inorganic materials 0.000 claims description 12
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 239000007864 aqueous solution Substances 0.000 claims description 7
- 239000007789 gas Substances 0.000 claims description 6
- 235000019260 propionic acid Nutrition 0.000 claims description 6
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 6
- 239000000376 reactant Substances 0.000 claims description 6
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 5
- -1 amine salt Chemical class 0.000 claims description 5
- 235000019253 formic acid Nutrition 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 abstract description 17
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 2
- 229910052760 oxygen Inorganic materials 0.000 abstract description 2
- 239000001301 oxygen Substances 0.000 abstract description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 2
- 239000006227 byproduct Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- 230000000171 quenching effect Effects 0.000 description 7
- 239000002253 acid Substances 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 229910052742 iron Inorganic materials 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 229910052804 chromium Inorganic materials 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 229910052718 tin Inorganic materials 0.000 description 3
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 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
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000000895 extractive distillation Methods 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 229910052750 molybdenum Inorganic materials 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229910052721 tungsten Inorganic materials 0.000 description 2
- 229910052720 vanadium Inorganic materials 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 229920002972 Acrylic fiber Polymers 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 229910052770 Uranium Inorganic materials 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 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
- 150000001412 amines Chemical class 0.000 description 1
- 239000000908 ammonium hydroxide Substances 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
- 229910052787 antimony Inorganic materials 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- 239000002638 heterogeneous catalyst Substances 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000010808 liquid waste Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229910052758 niobium Inorganic materials 0.000 description 1
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- 150000000000 tetracarboxylic acids Chemical class 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 229910052716 thallium Inorganic materials 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 150000003628 tricarboxylic acids Chemical class 0.000 description 1
- 229910052725 zinc 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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/06—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms of an acyclic and unsaturated carbon skeleton
- C07C255/07—Mononitriles
- C07C255/08—Acrylonitrile; Methacrylonitrile
-
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US38106602P | 2002-05-16 | 2002-05-16 | |
| PCT/US2003/015983 WO2003097583A1 (en) | 2002-05-16 | 2003-05-16 | Ammoxidation of carboxylic acids to a mixture of nitriles |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2005526135A JP2005526135A (ja) | 2005-09-02 |
| JP2005526135A5 JP2005526135A5 (enExample) | 2006-06-29 |
| JP4418364B2 true JP4418364B2 (ja) | 2010-02-17 |
Family
ID=29550065
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004505316A Expired - Lifetime JP4418364B2 (ja) | 2002-05-16 | 2003-05-16 | ニトリル類の混合物へのカルボン酸のアンモ酸化 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US6982342B2 (enExample) |
| EP (1) | EP1503982B1 (enExample) |
| JP (1) | JP4418364B2 (enExample) |
| KR (1) | KR100994094B1 (enExample) |
| CN (1) | CN1303062C (enExample) |
| AT (1) | ATE489358T1 (enExample) |
| AU (1) | AU2003233620A1 (enExample) |
| BR (1) | BR0309879B1 (enExample) |
| DE (1) | DE60335102D1 (enExample) |
| ES (1) | ES2355367T3 (enExample) |
| MX (1) | MXPA04011152A (enExample) |
| RU (1) | RU2311404C2 (enExample) |
| WO (1) | WO2003097583A1 (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108586178B (zh) * | 2013-10-10 | 2022-02-11 | 中国石油化工股份有限公司 | 腈及其相应胺的制造方法 |
| CN105016941B (zh) * | 2014-04-16 | 2018-06-22 | 中国石化扬子石油化工有限公司 | 腈及其相应胺的制造方法 |
| CN105001033B (zh) * | 2014-04-16 | 2018-06-22 | 中国石化扬子石油化工有限公司 | 腈及其相应胺的制造方法 |
| CN105001032B (zh) * | 2014-04-16 | 2018-03-16 | 中国石化扬子石油化工有限公司 | 腈及其相应胺的制造方法 |
| CN108546223B (zh) * | 2014-04-16 | 2022-02-11 | 中国石化扬子石油化工有限公司 | 腈及其相应胺的制造方法 |
| CN108558589B (zh) * | 2014-04-16 | 2022-02-08 | 中国石化扬子石油化工有限公司 | 腈及其相应胺的制造方法 |
| CN105016945B (zh) * | 2014-04-16 | 2018-03-16 | 中国石化扬子石油化工有限公司 | 腈及其相应胺的制造方法 |
| CN113813622A (zh) * | 2014-09-29 | 2021-12-21 | 英尼奥斯欧洲股份公司 | 用于工艺流的蒸发系统 |
| CN104447404B (zh) * | 2014-12-31 | 2017-01-18 | 南通醋酸化工股份有限公司 | 一种应用锆钨介孔分子筛催化制备乙腈的方法 |
| BR112018016979B8 (pt) * | 2016-02-19 | 2023-01-10 | Alliance Sustainable Energy | Sistemas e métodos para produção de nitrilas |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL135575C (enExample) * | ||||
| IT845600A (enExample) | 1967-09-07 | |||
| US4316856A (en) * | 1979-12-28 | 1982-02-23 | The Standard Oil Co. | Molybdenum-promoted antimony phosphate oxide complex catalysts also containing at least one of bismuth and tellurium |
| KR950006897B1 (ko) * | 1991-07-04 | 1995-06-26 | 롱-쁠랑 쉬미 | 포화 탄화수소의 암모산화 방법 |
| US5288473A (en) | 1992-10-09 | 1994-02-22 | The Standard Oil Company | Process for elimination of waste material during manufacture of acrylonitrile |
| IN184881B (enExample) * | 1995-01-31 | 2000-10-07 | Asahi Chemical Ind | |
| JPH08231487A (ja) | 1995-02-28 | 1996-09-10 | Asahi Chem Ind Co Ltd | アクリロニトリルの製造方法 |
| AU4966197A (en) | 1996-11-15 | 1998-06-10 | Mitsubishi Chemical Corporation | Process for the simultaneous preparation of acrylonitrile and acrylic acid |
| US6204407B1 (en) * | 1998-12-09 | 2001-03-20 | The Standard Oil Company | Ammoxidation of a mixture of alcohols to a mixture of nitriles to acetonitrile and HCN |
| US20010006614A1 (en) | 1998-12-23 | 2001-07-05 | Nero Linda L. | Process for recovery and recycle of ammonia from an acrylonitrile reactor effluent stream using an ammonium phosphate quench system |
| US6413485B2 (en) | 1999-05-27 | 2002-07-02 | The Standard Oil Company | Ammoxidation of a mixture of ketones to acetonitrile and HCN |
| JP4854149B2 (ja) | 2001-08-29 | 2012-01-18 | 旭化成ケミカルズ株式会社 | アセトニトリルを安定に増産する方法 |
-
2003
- 2003-05-15 US US10/438,586 patent/US6982342B2/en not_active Expired - Lifetime
- 2003-05-16 EP EP03729057A patent/EP1503982B1/en not_active Expired - Lifetime
- 2003-05-16 WO PCT/US2003/015983 patent/WO2003097583A1/en not_active Ceased
- 2003-05-16 AT AT03729057T patent/ATE489358T1/de not_active IP Right Cessation
- 2003-05-16 KR KR1020047018419A patent/KR100994094B1/ko not_active Expired - Lifetime
- 2003-05-16 ES ES03729057T patent/ES2355367T3/es not_active Expired - Lifetime
- 2003-05-16 CN CNB038111500A patent/CN1303062C/zh not_active Expired - Lifetime
- 2003-05-16 DE DE60335102T patent/DE60335102D1/de not_active Expired - Lifetime
- 2003-05-16 AU AU2003233620A patent/AU2003233620A1/en not_active Abandoned
- 2003-05-16 BR BRPI0309879-6B1A patent/BR0309879B1/pt active IP Right Grant
- 2003-05-16 MX MXPA04011152A patent/MXPA04011152A/es active IP Right Grant
- 2003-05-16 RU RU2004137100/04A patent/RU2311404C2/ru active
- 2003-05-16 JP JP2004505316A patent/JP4418364B2/ja not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| EP1503982A1 (en) | 2005-02-09 |
| KR100994094B1 (ko) | 2010-11-12 |
| RU2311404C2 (ru) | 2007-11-27 |
| ES2355367T3 (es) | 2011-03-25 |
| ATE489358T1 (de) | 2010-12-15 |
| CN1303062C (zh) | 2007-03-07 |
| EP1503982B1 (en) | 2010-11-24 |
| CN1701060A (zh) | 2005-11-23 |
| RU2004137100A (ru) | 2005-06-27 |
| JP2005526135A (ja) | 2005-09-02 |
| DE60335102D1 (de) | 2011-01-05 |
| BR0309879A (pt) | 2005-03-01 |
| US6982342B2 (en) | 2006-01-03 |
| WO2003097583A1 (en) | 2003-11-27 |
| AU2003233620A1 (en) | 2003-12-02 |
| BR0309879B1 (pt) | 2013-07-30 |
| MXPA04011152A (es) | 2005-02-17 |
| KR20040108820A (ko) | 2004-12-24 |
| US20030219372A1 (en) | 2003-11-27 |
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Legal Events
| Date | Code | Title | Description |
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| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20060511 |
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| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20060511 |
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