JP2013198902A - 不飽和ニトリル類の製造のための高度な活性および選択性を有する触媒系 - Google Patents
不飽和ニトリル類の製造のための高度な活性および選択性を有する触媒系 Download PDFInfo
- Publication number
- JP2013198902A JP2013198902A JP2013100322A JP2013100322A JP2013198902A JP 2013198902 A JP2013198902 A JP 2013198902A JP 2013100322 A JP2013100322 A JP 2013100322A JP 2013100322 A JP2013100322 A JP 2013100322A JP 2013198902 A JP2013198902 A JP 2013198902A
- Authority
- JP
- Japan
- Prior art keywords
- catalyst
- catalyst system
- present
- support material
- production
- 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.)
- Granted
Links
- 150000002825 nitriles Chemical class 0.000 title claims abstract description 14
- 238000004519 manufacturing process Methods 0.000 title abstract description 8
- 230000003197 catalytic effect Effects 0.000 title abstract description 3
- 239000003054 catalyst Substances 0.000 claims abstract description 81
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims abstract description 14
- 150000001336 alkenes Chemical class 0.000 claims abstract description 12
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims abstract description 9
- 239000010955 niobium Substances 0.000 claims description 19
- 229910052758 niobium Inorganic materials 0.000 claims description 16
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 12
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 claims description 12
- 239000000463 material Substances 0.000 claims description 6
- 230000000737 periodic effect Effects 0.000 claims description 6
- 239000000377 silicon dioxide Substances 0.000 claims description 6
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 4
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 2
- ZKATWMILCYLAPD-UHFFFAOYSA-N niobium pentoxide Inorganic materials O=[Nb](=O)O[Nb](=O)=O ZKATWMILCYLAPD-UHFFFAOYSA-N 0.000 claims description 2
- URLJKFSTXLNXLG-UHFFFAOYSA-N niobium(5+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[Nb+5].[Nb+5] URLJKFSTXLNXLG-UHFFFAOYSA-N 0.000 claims description 2
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 claims description 2
- 229910010271 silicon carbide Inorganic materials 0.000 claims description 2
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 claims 1
- 150000004645 aluminates Chemical class 0.000 claims 1
- 150000001642 boronic acid derivatives Chemical class 0.000 claims 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 claims 1
- 229910052816 inorganic phosphate Inorganic materials 0.000 claims 1
- 229910052901 montmorillonite Inorganic materials 0.000 claims 1
- 239000008262 pumice Substances 0.000 claims 1
- 150000004760 silicates Chemical class 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 12
- 238000006243 chemical reaction Methods 0.000 description 7
- 238000007254 oxidation reaction Methods 0.000 description 7
- 229910052750 molybdenum Inorganic materials 0.000 description 6
- 229910052797 bismuth Inorganic materials 0.000 description 5
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 4
- 239000011733 molybdenum Substances 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 229910052720 vanadium Inorganic materials 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 229910052787 antimony Inorganic materials 0.000 description 3
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 229910052759 nickel Inorganic materials 0.000 description 3
- 229910052721 tungsten Inorganic materials 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- BYUANIDVEAKBHT-UHFFFAOYSA-N [Mo].[Bi] Chemical compound [Mo].[Bi] BYUANIDVEAKBHT-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000007809 chemical reaction catalyst Substances 0.000 description 2
- 229910052804 chromium Inorganic materials 0.000 description 2
- 238000001941 electron spectroscopy Methods 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 229910052748 manganese Inorganic materials 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 229910052702 rhenium Inorganic materials 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 229910052715 tantalum Inorganic materials 0.000 description 2
- 229910052713 technetium Inorganic materials 0.000 description 2
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 2
- 241000043078 Bidens mottle virus Species 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 229910052785 arsenic Inorganic materials 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- DKUYEPUUXLQPPX-UHFFFAOYSA-N dibismuth;molybdenum;oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[Mo].[Mo].[Bi+3].[Bi+3] DKUYEPUUXLQPPX-UHFFFAOYSA-N 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 1
- 238000007210 heterogeneous catalysis Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000001247 metal acetylides Chemical class 0.000 description 1
- -1 methacryloyl Chemical group 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910003455 mixed metal oxide Inorganic materials 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- 238000006213 oxygenation reaction Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- XQZYPMVTSDWCCE-UHFFFAOYSA-N phthalonitrile Chemical compound N#CC1=CC=CC=C1C#N XQZYPMVTSDWCCE-UHFFFAOYSA-N 0.000 description 1
- 229920006391 phthalonitrile polymer Polymers 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229910052716 thallium Inorganic materials 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Images
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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/002—Mixed oxides other than spinels, e.g. perovskite
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/24—Chromium, molybdenum or tungsten
- B01J23/31—Chromium, molybdenum or tungsten combined with bismuth
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/18—Arsenic, antimony or bismuth
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/20—Vanadium, niobium or tantalum
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2523/00—Constitutive chemical elements of heterogeneous catalysts
-
- 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)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Abstract
【解決手段】実験式BiaMobVcSbdNbeAfBgOxで表される原子比を有する触媒である、対応するオレフィン類から不飽和ニトリル類を生成するための改良された触媒、およびその使用方法。
【選択図】図1
Description
BiaMobVcSbdNbeAfBgOx
上式中
A=周期表のVB族(例えば、V、Nb、Ta)、VIB族(例えば、Cr、Mo、W)、VIIB族(例えば、Mn、Tc、Re)、またはVIII族(例えば、Fe、Co、Ni)から選択される1種類以上の元素;
B=周期表のIA族(例えば、Li、Na、K)またはIIA族(例えば、Mg、Ca)から選択される少なくとも1種類のアルカリ助触媒;
a=0.01〜12;
b=0.01〜12;
c=0.01〜2;
d=0.01〜10;
e=0.01〜1;
f=0〜2、好ましくは0.01〜1;
g=0〜1、好ましくは0.001〜0.5;および
x=存在する元素に要求される原子価を満足させるために必要な酸素原子数、である。
BiaMobVcSbdNbeAfBgOx
ただし、上式中
A=周期表のVB族(例えば、V、Nb、Ta)、VIB族(例えば、Cr、Mo、W)、VIIB族(例えば、Mn、Tc、Re)、またはVIII族(例えば、Fe、Co、Ni)から選択される1種類以上の元素;
B=周期表のIA族(例えば、Li、Na、K)またはIIA族(例えば、Mg、Ca)から選択される少なくとも1種類のアルカリ助触媒;
a=0.01〜12;
b=0.01〜12;
c=0.01〜2;
d=0.01〜10;
e=0.01〜1;
f=0〜2、好ましくは0.01〜1;
g=0〜1、好ましくは0.001〜0.5;および
x=存在する元素に要求される原子価を満足するために必要な酸素原子数、である。
1.「W/F」は、触媒重量(単位g)を標準温度および標準圧力で測定した反応物質流の流速(単位ml/sec)で割った値として定義される。
2.「プロピレン(C3H6)転化率」は:
{(供給材料中のC3H6のモル数−流出物中のC3H6のモル数)/供給材料中のC3H6のモル数} ×100(%)
として定義される。
3.「アクリロニトリル(ACN)選択率」は:
(流出物中のACNのモル数/転化したC3H6のモル数) ×100(%)
として定義される。
4.「アクリロニトリル(ACN)収率」は:
(生成したACNのモル数/供給材料中のC3H6のモル数) ×100(%)
として定義される。
部分A
10.2gのSb2O3を、20mlの水および3.18gのV2O5と混合して懸濁させた。その混合物を、ペーストが形成されるまで煮沸した。次に、ペーストを120℃で乾燥して、760℃の気流下で2時間かけて焼成した。
97gのBi(NO3)35H2Oを、184mlの水と30mlのHNO3(濃硝酸)との混合物に溶解した。これとは別に、28.78gのMoO3を、72mlの水と30mlの濃NH4OHとの混合物に溶解した。これら2つの溶液を混合し、NH4OHを使用してpHを4に調整した。次に、この混合物を約2時間煮沸して、ろ過して、約1000mlの水で洗浄した。
297gのシリカ30重量%溶液のpHを、HNO3を用いてpH=2に調製して部分Cを調製した。次に部分AとBを部分Cに加えた。この混合物を数時間撹拌して、次に120℃で乾燥して、550℃の気流下で焼成した。得られた触媒の性質を、XPS法(X線電子分光法)によって調べた。その結果を図1に示す。
この触媒も、上述の例1に記載の方法に従って調製した。必要量の五酸化ニオブを部分Bのモリブデン溶液に加えることで、ニオブを系に導入した。しかしながら、同様の目的で任意のニオブ源を使用することができる。
例1および例2の焼成した触媒を35〜60メッシュに粉砕した。各触媒5gを、管状固定層ステンレス鋼製反応器に加えた。
プロピレン/O2/NH3/He=7.9/16.8/10/65.3および空間速度「W/F」が3の供給材料組成で行った。
例1および例2の触媒を、上述の同等の条件下で試験した。
Claims (10)
- 対応するオレフィン類から不飽和ニトリル類を生成するための触媒系であって、下記の実験式、
BiaMobVcSbdNbeAfBgOx
(式中
A=周期表のVB族、VIB族、VIIB族、またはVIII族から選択される1種類以上の元素;
B=周期表のIA族またはIIA族から選択される少なくとも1種類のアルカリ助触媒;
a=0.01〜12;
b=0.01〜12;
c=0.01〜2;
d=0.01〜10;
e=0.01〜1;
f=0〜1;
g=0〜0.5;および
x=存在する元素に要求される原子価を満足するために必要な酸素原子数)
を有する触媒を含む、触媒系。 - 前記eが0.05〜0.5である請求項1に記載の触媒系。
- 前記オレフィン類がプロピレン、イソブチレンまたはそれらの混合物から選択され、前記ニトリル類がアクリロニトリル、メタクリロニトリルまたはそれらの混合物から選択される請求項1に記載の触媒系。
- 前記触媒が、シリカ、アルミナ、ジルコニア、チタニア、アランダム、炭化ケイ素、アルミナシリカ、無機リン酸塩類、ケイ酸塩類、アルミン酸塩類、ホウ酸塩類および炭酸塩類、軽石、モンモリロナイト、またはそれらの混合物から選択される触媒担持物質上に担持される請求項1に記載の触媒系。
- 前記触媒担持物質がシリカである請求項4に記載の触媒系。
- 前記触媒担持物質が前記触媒の40〜70重量%を有する請求項4に記載の触媒系。
- 前記触媒担持物質が前記触媒の40〜70重量%を有する請求項5に記載の触媒系。
- 前記触媒が水溶性五酸化ニオブから誘導されるニオブを含む請求項1に記載の触媒系。
- 前記fが0.01〜1の範囲であり、前記gが0.001〜0.5の範囲である請求項1に記載の触媒系。
- 前記触媒が水溶性ニオブ源から誘導されるニオブを含む請求項1に記載の触媒系。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US09/228,885 US6037304A (en) | 1999-01-11 | 1999-01-11 | Highly active and selective catalysts for the production of unsaturated nitriles, methods of making and using the same |
US09/228885 | 1999-01-11 |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2000002312A Division JP5478802B2 (ja) | 1999-01-11 | 2000-01-11 | 不飽和ニトリル類の製造のための高度な活性および選択性を有する触媒、その製造法および使用法 |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2013198902A true JP2013198902A (ja) | 2013-10-03 |
JP2013198902A5 JP2013198902A5 (ja) | 2014-01-16 |
JP5608263B2 JP5608263B2 (ja) | 2014-10-15 |
Family
ID=22858938
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2000002312A Expired - Fee Related JP5478802B2 (ja) | 1999-01-11 | 2000-01-11 | 不飽和ニトリル類の製造のための高度な活性および選択性を有する触媒、その製造法および使用法 |
JP2013100322A Expired - Fee Related JP5608263B2 (ja) | 1999-01-11 | 2013-05-10 | 不飽和ニトリル類の製造のための高度な活性および選択性を有する触媒系、並びに対応するオレフィン類から不飽和ニトリル類を生成する方法 |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2000002312A Expired - Fee Related JP5478802B2 (ja) | 1999-01-11 | 2000-01-11 | 不飽和ニトリル類の製造のための高度な活性および選択性を有する触媒、その製造法および使用法 |
Country Status (5)
Country | Link |
---|---|
US (2) | US6037304A (ja) |
EP (1) | EP1020433B1 (ja) |
JP (2) | JP5478802B2 (ja) |
DE (1) | DE60009582T2 (ja) |
SA (2) | SA99200392B1 (ja) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2000229929A (ja) | 1999-01-11 | 2000-08-22 | Abdulwahed Mazhar | 不飽和ニトリル類の製造のための高度な活性および選択性を有する触媒、その製造法および使用法 |
WO2015133510A1 (ja) * | 2014-03-06 | 2015-09-11 | 旭化成ケミカルズ株式会社 | 酸化物触媒及びその製造方法、並びに、不飽和ニトリルの製造方法 |
WO2015151726A1 (ja) * | 2014-03-31 | 2015-10-08 | 旭化成ケミカルズ株式会社 | 酸化物触媒の製造方法、及び不飽和ニトリルの製造方法 |
Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6281378B1 (en) * | 1995-06-08 | 2001-08-28 | Nippon Shokubai Co., Ltd. | Vanadium-containing catalysts, process for manufacturing and use of the same |
US6486091B1 (en) * | 2000-03-14 | 2002-11-26 | Saudi Basic Industries Corporation | Process for making highly active and selective catalysts for the production of unsaturated nitriles |
JP4530595B2 (ja) * | 2000-12-13 | 2010-08-25 | 旭化成ケミカルズ株式会社 | 酸化またはアンモ酸化用酸化物触媒 |
MXPA03005601A (es) * | 2000-12-22 | 2004-12-02 | Axys Pharm Inc | Nuevos compuestos y composiciones como inhibidores de catepsina. |
EP1349651A4 (en) * | 2000-12-22 | 2006-07-19 | Uop Llc | CRYSTALLINE MULTI-METAL OXIDE COMPOSITIONS, METHOD OF PREPARING THE SAME AND METHOD OF USE OF THE COMPOSITION |
DE20122515U1 (de) * | 2001-07-26 | 2005-12-22 | Berthold, Hermann | Anlage zum Behandeln von Flüssigkeiten, insbesondere zum Behandeln von kontaminiertem Wasser |
KR20030035896A (ko) * | 2001-10-26 | 2003-05-09 | 롬 앤드 하스 캄파니 | 혼합 금속 산화물 촉매의 처리 |
ZA200209470B (en) * | 2001-12-04 | 2003-06-03 | Rohm & Haas | Improved processes for the preparation of olefins, unsaturated carboxylic acids and unsaturated nitriles from alkanes. |
JP4242197B2 (ja) * | 2003-04-18 | 2009-03-18 | ダイヤニトリックス株式会社 | アクリロニトリル合成用触媒 |
US8772195B2 (en) | 2009-01-30 | 2014-07-08 | Asahi Kasei Chemicals Corporation | Method for producing silica-supported catalyst, and method for producing unsaturated carboxylic acid or unsaturated nitrile |
JP7456727B2 (ja) | 2019-03-27 | 2024-03-27 | 旭化成株式会社 | アクリロニトリル合成触媒、アクリロニトリル合成触媒の製造方法及びアクリロニトリルの製造方法 |
GB2591309B (en) * | 2020-01-23 | 2024-07-10 | Ntdrill Holdings Llc | Drilling choke with matched actuator |
Citations (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS4931618A (ja) * | 1972-07-28 | 1974-03-22 | ||
JPS50129503A (ja) * | 1974-03-29 | 1975-10-13 | ||
JPS5697549A (en) * | 1979-12-17 | 1981-08-06 | Monsanto Co | Catalyst for oxidizing hydrocarbon and ammonia and manufacture of acrylnitril |
JPS62201646A (ja) * | 1986-02-27 | 1987-09-05 | Mitsubishi Petrochem Co Ltd | 複合酸化物触媒の製造法 |
JPH02257A (ja) * | 1987-11-25 | 1990-01-05 | Mitsubishi Kasei Corp | ニトリルの製造法 |
JPH0259046A (ja) * | 1988-08-26 | 1990-02-28 | Nitto Chem Ind Co Ltd | モリブデン含有アンモ酸化触媒の製法 |
JPH04118051A (ja) * | 1990-09-10 | 1992-04-20 | Nitto Chem Ind Co Ltd | 鉄・アンチモン・モリブデン含有酸化物触媒組成物およびその製法 |
JPH05148212A (ja) * | 1991-05-09 | 1993-06-15 | Mitsubishi Kasei Corp | ニトリルの製造法 |
JPH06285372A (ja) * | 1992-12-24 | 1994-10-11 | Mitsubishi Kasei Corp | ニトリル製造用触媒の製造方法 |
JPH09504226A (ja) * | 1993-10-21 | 1997-04-28 | ビーエーエスエフ アクチェンゲゼルシャフト | 基本成分として元素V及びMoを酸化物の形で含有する触媒活性複合金属酸化物材料の製造方法 |
JPH09157241A (ja) * | 1995-10-05 | 1997-06-17 | Mitsubishi Chem Corp | ニトリルの製造法 |
JP2000005603A (ja) * | 1998-04-23 | 2000-01-11 | Mitsubishi Rayon Co Ltd | 不飽和ニトリル製造用触媒組成物 |
Family Cites Families (41)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3131223A (en) * | 1957-01-04 | 1964-04-28 | Consortium Elektrochem Ind | Process for the production of aldehydes and ketones |
DE1129469B (de) * | 1957-09-28 | 1962-05-17 | Hoechst Ag | Verfahren zur Herstellung von Aldehyden, Ketonen oder den Aldehyden entsprechenden Saeuren |
US3057915A (en) * | 1957-09-14 | 1962-10-09 | Hoechst Ag | Process for oxidizing olefins to aldehydes, ketones and acids |
US3240805A (en) * | 1961-10-13 | 1966-03-15 | Halcon International Inc | Process for producing acetic acid |
JPS509772B2 (ja) * | 1972-08-04 | 1975-04-16 | ||
US4190556A (en) * | 1973-07-19 | 1980-02-26 | Standard Oil Company | Production of unsaturated nitriles using catalysts promoted with various metals |
US4339355A (en) * | 1975-10-09 | 1982-07-13 | Union Carbide Corporation | Catalytic oxide of molybdenum, vanadium, niobium and optional 4th metal |
US4040978A (en) * | 1975-11-28 | 1977-08-09 | Monsanto Company | Production of (amm)oxidation catalyst |
DE2627068C3 (de) * | 1976-06-16 | 1980-01-17 | Institut Neftechimitscheskich Processov Imeni Akademika Ju. G. Mamedalieva Akademii Nauk Azerbaidschanskoj Ssr, Baku (Sowjetunion) | Verfahren zur Herstellung von Phthalsäuredinitril |
US4292203A (en) * | 1977-04-04 | 1981-09-29 | The Standard Oil Company | Oxidation catalysts |
US4148757A (en) * | 1977-08-10 | 1979-04-10 | The Standard Oil Company | Process for forming multi-component oxide complex catalysts |
US4405498A (en) * | 1979-12-17 | 1983-09-20 | Monsanto Company | Oxidation and ammoxidation catalysts |
JPS56140931A (en) * | 1980-04-04 | 1981-11-04 | Nippon Zeon Co Ltd | Preparation of conjugated diolefin |
US4250346A (en) * | 1980-04-14 | 1981-02-10 | Union Carbide Corporation | Low temperature oxydehydrogenation of ethane to ethylene |
JPS59204164A (ja) * | 1983-05-06 | 1984-11-19 | Asahi Chem Ind Co Ltd | 不飽和ニトリルの製法 |
GB8915410D0 (en) * | 1989-07-05 | 1989-08-23 | Bp Chem Int Ltd | Chemical process |
US4547484A (en) * | 1984-04-09 | 1985-10-15 | Monsanto Company | Method of preparing a catalyst for the oxidation and ammoxidation of olefins |
US4568790A (en) * | 1984-06-28 | 1986-02-04 | Union Carbide Corporation | Process for oxydehydrogenation of ethane to ethylene |
US4524236A (en) * | 1984-06-28 | 1985-06-18 | Union Carbide Corporation | Process for oxydehydrogenation of ethane to ethylene |
US4596787A (en) * | 1985-04-11 | 1986-06-24 | Union Carbide Corporation | Process for preparing a supported catalyst for the oxydehydrogenation of ethane to ethylene |
US4899003A (en) * | 1985-07-11 | 1990-02-06 | Union Carbide Chemicals And Plastics Company Inc. | Process for oxydehydrogenation of ethane to ethylene |
US4788173A (en) * | 1985-12-20 | 1988-11-29 | The Standard Oil Company | Catalytic mixtures for ammoxidation of paraffins |
US4847850A (en) * | 1986-12-23 | 1989-07-11 | Spectra-Physics, Inc. | Continuum generation with miniaturized Q-switched diode pumped solid state laser |
US5162578A (en) * | 1987-06-12 | 1992-11-10 | Union Carbide Chemicals & Plastics Technology Corporation | Acetic acid from ethane, ethylene and oxygen |
US5049692A (en) * | 1987-11-25 | 1991-09-17 | Mitsubishi Kasei Corporation | Catalytic conversion of alkanes to nitriles, and a catalyst therefor |
US5134105A (en) * | 1990-03-19 | 1992-07-28 | The Standard Oil Company | Catalyst for propylene ammoxidation to acrylonitrile |
GB9022127D0 (en) * | 1990-10-11 | 1990-11-21 | Bp Chem Int Ltd | Process |
US5300682A (en) * | 1991-06-10 | 1994-04-05 | The Standard Oil Co. | Catalytic oxidation of ethane to acetic acid |
US5472925A (en) * | 1991-08-08 | 1995-12-05 | Mitsubishi Chemical Corporation | Catalyst for the production of nitriles |
US5198580A (en) * | 1991-11-18 | 1993-03-30 | The Standard Oil Company | Process for oxidation of propane |
DE4220859A1 (de) * | 1992-06-25 | 1994-01-05 | Basf Ag | Multimetalloxidmassen |
EP0603836B1 (en) * | 1992-12-24 | 1998-05-20 | Mitsubishi Chemical Corporation | Process for preparing a catalyst useful for producing a nitrile |
TW295579B (ja) * | 1993-04-06 | 1997-01-11 | Showa Denko Kk | |
FR2705668B1 (fr) * | 1993-05-28 | 1995-08-25 | Rhone Poulenc Chimie | Procédé de préparation d'acide acétique par oxydation ménagée de l'éthane. |
DE4332542A1 (de) * | 1993-09-24 | 1995-03-30 | Basf Ag | Katalysator auf der Basis von Fe-, Co-, Bi- und Mo-Oxiden |
US5688739A (en) * | 1995-05-01 | 1997-11-18 | The Standard Oil Company | Ammoxidation catalysts containing germanium to produce high yields of acrylonitrile |
US5821192A (en) * | 1996-09-23 | 1998-10-13 | The Standard Oil Company | Method of improving the attrition resistance of V/SB oxide based catalyst |
US5866502A (en) * | 1997-03-27 | 1999-02-02 | The Standard Oil Co. | Process for the preparation of antimonate catalysts for (AMM) oxidation of alkanes and alkenes |
UA57721C2 (uk) * | 1997-08-11 | 2003-07-15 | Асахі Касеі Кабусікі Кайся | Спосіб виготовлення акрилонітрилу або метакрилонітрилу із пропану або ізобутану |
US6156920A (en) * | 1998-03-26 | 2000-12-05 | The Standard Oil Company | Molybdenum promoted vanadium-antimony-oxide based catalyst for selective paraffin ammoxidation |
US6037304A (en) | 1999-01-11 | 2000-03-14 | Saudi Basic Industries Corporation | Highly active and selective catalysts for the production of unsaturated nitriles, methods of making and using the same |
-
1999
- 1999-01-11 US US09/228,885 patent/US6037304A/en not_active Expired - Lifetime
- 1999-07-28 SA SA99200392A patent/SA99200392B1/ar unknown
- 1999-11-01 US US09/431,744 patent/US6124233A/en not_active Expired - Lifetime
-
2000
- 2000-01-05 EP EP00200009A patent/EP1020433B1/en not_active Expired - Lifetime
- 2000-01-05 DE DE60009582T patent/DE60009582T2/de not_active Expired - Lifetime
- 2000-01-11 JP JP2000002312A patent/JP5478802B2/ja not_active Expired - Fee Related
-
2005
- 2005-11-30 SA SA05260373A patent/SA05260373B1/ar unknown
-
2013
- 2013-05-10 JP JP2013100322A patent/JP5608263B2/ja not_active Expired - Fee Related
Patent Citations (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS4931618A (ja) * | 1972-07-28 | 1974-03-22 | ||
JPS50129503A (ja) * | 1974-03-29 | 1975-10-13 | ||
JPS5697549A (en) * | 1979-12-17 | 1981-08-06 | Monsanto Co | Catalyst for oxidizing hydrocarbon and ammonia and manufacture of acrylnitril |
JPS62201646A (ja) * | 1986-02-27 | 1987-09-05 | Mitsubishi Petrochem Co Ltd | 複合酸化物触媒の製造法 |
JPH02257A (ja) * | 1987-11-25 | 1990-01-05 | Mitsubishi Kasei Corp | ニトリルの製造法 |
JPH0259046A (ja) * | 1988-08-26 | 1990-02-28 | Nitto Chem Ind Co Ltd | モリブデン含有アンモ酸化触媒の製法 |
JPH04118051A (ja) * | 1990-09-10 | 1992-04-20 | Nitto Chem Ind Co Ltd | 鉄・アンチモン・モリブデン含有酸化物触媒組成物およびその製法 |
JPH05148212A (ja) * | 1991-05-09 | 1993-06-15 | Mitsubishi Kasei Corp | ニトリルの製造法 |
JPH06285372A (ja) * | 1992-12-24 | 1994-10-11 | Mitsubishi Kasei Corp | ニトリル製造用触媒の製造方法 |
JPH09504226A (ja) * | 1993-10-21 | 1997-04-28 | ビーエーエスエフ アクチェンゲゼルシャフト | 基本成分として元素V及びMoを酸化物の形で含有する触媒活性複合金属酸化物材料の製造方法 |
JPH09157241A (ja) * | 1995-10-05 | 1997-06-17 | Mitsubishi Chem Corp | ニトリルの製造法 |
JP2000005603A (ja) * | 1998-04-23 | 2000-01-11 | Mitsubishi Rayon Co Ltd | 不飽和ニトリル製造用触媒組成物 |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2000229929A (ja) | 1999-01-11 | 2000-08-22 | Abdulwahed Mazhar | 不飽和ニトリル類の製造のための高度な活性および選択性を有する触媒、その製造法および使用法 |
WO2015133510A1 (ja) * | 2014-03-06 | 2015-09-11 | 旭化成ケミカルズ株式会社 | 酸化物触媒及びその製造方法、並びに、不飽和ニトリルの製造方法 |
JP6087471B2 (ja) * | 2014-03-06 | 2017-03-01 | 旭化成株式会社 | 酸化物触媒及びその製造方法、並びに、不飽和ニトリルの製造方法 |
US10179763B2 (en) | 2014-03-06 | 2019-01-15 | Asahi Kasei Kabushiki Kaisha | Oxide catalyst and method for producing same, and method for producing unsaturated nitrile |
WO2015151726A1 (ja) * | 2014-03-31 | 2015-10-08 | 旭化成ケミカルズ株式会社 | 酸化物触媒の製造方法、及び不飽和ニトリルの製造方法 |
CN105813732A (zh) * | 2014-03-31 | 2016-07-27 | 旭化成株式会社 | 氧化物催化剂的制造方法及不饱和腈的制造方法 |
JPWO2015151726A1 (ja) * | 2014-03-31 | 2017-04-13 | 旭化成株式会社 | 酸化物触媒の製造方法、及び不飽和ニトリルの製造方法 |
CN105813732B (zh) * | 2014-03-31 | 2020-03-13 | 旭化成株式会社 | 氧化物催化剂的制造方法及不饱和腈的制造方法 |
Also Published As
Publication number | Publication date |
---|---|
EP1020433A2 (en) | 2000-07-19 |
SA99200392B1 (ar) | 2006-07-31 |
US6124233A (en) | 2000-09-26 |
US6037304A (en) | 2000-03-14 |
JP5608263B2 (ja) | 2014-10-15 |
DE60009582D1 (de) | 2004-05-13 |
EP1020433A3 (en) | 2000-08-16 |
JP2000229929A (ja) | 2000-08-22 |
EP1020433B1 (en) | 2004-04-07 |
JP5478802B2 (ja) | 2014-04-23 |
DE60009582T2 (de) | 2004-08-05 |
SA05260373B1 (ar) | 2006-09-04 |
SA05260373A (ar) | 2005-12-03 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP5608263B2 (ja) | 不飽和ニトリル類の製造のための高度な活性および選択性を有する触媒系、並びに対応するオレフィン類から不飽和ニトリル類を生成する方法 | |
US7319179B2 (en) | Method for the oxidative dehydrogenation of ethane | |
EP0767164B1 (en) | Method for producing a nitrile | |
EP0166438B1 (en) | Process for oxydehydrogenation of ethane to ethylene | |
EP0529853A2 (en) | Catalyst and process for producing nitriles | |
US5534650A (en) | Method for producing a nitrile | |
JPH0813332B2 (ja) | メタクロレイン及びメタクリル酸の製造用触媒の調製法 | |
JP4081824B2 (ja) | アクリル酸の製造方法 | |
JP4368997B2 (ja) | 不飽和ニトリル類の製造のための高度な活性および選択性を有する触媒、その製造法および使用法 | |
JP3536326B2 (ja) | ニトリル製造用触媒の製造方法 | |
JP4410954B2 (ja) | 不飽和ニトリル類製造用の高活性選択性触媒の製造方法 | |
JP2004534650A (ja) | 特にアクリル酸、アクリロニトリルおよびこれらの誘導体の入手法におけるアルカンおよび/またはアルケンの選択的酸化とアンモ酸化用触媒 | |
JPH08504809A (ja) | (メト)アクリロニトリルの製造法 | |
JP2520279B2 (ja) | アクリロニトリルの製造方法 | |
JP3505547B2 (ja) | アクリロニトリルの製造方法 | |
JP3818697B2 (ja) | アンモ酸化触媒及びそれを用いたニトリルの製造方法 | |
JP2000051693A (ja) | 炭化水素の気相接触酸化用触媒の製造方法 | |
JP3768289B2 (ja) | アンモ酸化触媒およびそれを用いたニトリルの製造方法 | |
JP3487516B2 (ja) | フェノキシ置換ベンゾニトリルの製造法 | |
JP3894986B2 (ja) | アンモ酸化触媒およびそれを用いたニトリルの製造方法 | |
JPH08259487A (ja) | 不飽和アルデヒドの製造方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20131127 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20140717 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20140805 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20140829 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 5608263 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
LAPS | Cancellation because of no payment of annual fees |