JP5378412B2 - ニトリル化合物の製造方法 - Google Patents
ニトリル化合物の製造方法 Download PDFInfo
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- JP5378412B2 JP5378412B2 JP2010542605A JP2010542605A JP5378412B2 JP 5378412 B2 JP5378412 B2 JP 5378412B2 JP 2010542605 A JP2010542605 A JP 2010542605A JP 2010542605 A JP2010542605 A JP 2010542605A JP 5378412 B2 JP5378412 B2 JP 5378412B2
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- Prior art keywords
- catalyst
- hydrodenitrogenation
- nitrile
- producing
- mpa
- Prior art date
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- -1 nitrile compound Chemical class 0.000 title claims description 10
- 238000004519 manufacturing process Methods 0.000 title description 15
- 239000003054 catalyst Substances 0.000 claims description 57
- 238000000034 method Methods 0.000 claims description 51
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 34
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 32
- FPPLREPCQJZDAQ-UHFFFAOYSA-N 2-methylpentanedinitrile Chemical group N#CC(C)CCC#N FPPLREPCQJZDAQ-UHFFFAOYSA-N 0.000 claims description 31
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 28
- 239000006227 byproduct Substances 0.000 claims description 26
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 24
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 24
- 150000002430 hydrocarbons Chemical class 0.000 claims description 23
- BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 17
- 229910021529 ammonia Inorganic materials 0.000 claims description 16
- CFEYBLWMNFZOPB-UHFFFAOYSA-N Allylacetonitrile Natural products C=CCCC#N CFEYBLWMNFZOPB-UHFFFAOYSA-N 0.000 claims description 15
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims description 14
- 238000005669 hydrocyanation reaction Methods 0.000 claims description 14
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 13
- 229910052697 platinum Inorganic materials 0.000 claims description 13
- 150000002825 nitriles Chemical group 0.000 claims description 12
- 238000000629 steam reforming Methods 0.000 claims description 12
- UVKXJAUUKPDDNW-NSCUHMNNSA-N (e)-pent-3-enenitrile Chemical compound C\C=C\CC#N UVKXJAUUKPDDNW-NSCUHMNNSA-N 0.000 claims description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 10
- ISBHMJZRKAFTGE-ONEGZZNKSA-N (e)-pent-2-enenitrile Chemical compound CC\C=C\C#N ISBHMJZRKAFTGE-ONEGZZNKSA-N 0.000 claims description 8
- 229910052759 nickel Inorganic materials 0.000 claims description 8
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 7
- WBAXCOMEMKANRN-UHFFFAOYSA-N 2-methylbut-3-enenitrile Chemical compound C=CC(C)C#N WBAXCOMEMKANRN-UHFFFAOYSA-N 0.000 claims description 6
- IHXNSHZBFXGOJM-HWKANZROSA-N (e)-2-methylbut-2-enenitrile Chemical compound C\C=C(/C)C#N IHXNSHZBFXGOJM-HWKANZROSA-N 0.000 claims description 5
- GDCJAPJJFZWILF-UHFFFAOYSA-N 2-ethylbutanedinitrile Chemical compound CCC(C#N)CC#N GDCJAPJJFZWILF-UHFFFAOYSA-N 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 239000000377 silicon dioxide Substances 0.000 claims description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 4
- 229910021536 Zeolite Inorganic materials 0.000 claims description 4
- 150000002894 organic compounds Chemical class 0.000 claims description 4
- 239000010457 zeolite Substances 0.000 claims description 4
- 229910000323 aluminium silicate Inorganic materials 0.000 claims description 3
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- 229910052703 rhodium Inorganic materials 0.000 claims description 2
- 239000010948 rhodium Substances 0.000 claims description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 2
- 229910052707 ruthenium Inorganic materials 0.000 claims description 2
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 28
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 15
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 14
- 125000004433 nitrogen atom Chemical group N* 0.000 description 9
- 239000003446 ligand Substances 0.000 description 7
- 239000007789 gas Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- JEGMWWXJUXDNJN-UHFFFAOYSA-N 3-methylpiperidine Chemical compound CC1CCCNC1 JEGMWWXJUXDNJN-UHFFFAOYSA-N 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N methyl pentane Natural products CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 3
- 239000002699 waste material Substances 0.000 description 3
- JZUHIOJYCPIVLQ-UHFFFAOYSA-N 2-methylpentane-1,5-diamine Chemical compound NCC(C)CCCN JZUHIOJYCPIVLQ-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 238000001193 catalytic steam reforming Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000000567 combustion gas Substances 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 239000003345 natural gas Substances 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 150000008301 phosphite esters Chemical class 0.000 description 2
- 125000004437 phosphorous atom Chemical group 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- FHKPTEOFUHYQFY-UHFFFAOYSA-N 2-aminohexanenitrile Chemical compound CCCCC(N)C#N FHKPTEOFUHYQFY-UHFFFAOYSA-N 0.000 description 1
- RGDQRXPEZUNWHX-UHFFFAOYSA-N 3-methylpyridin-2-amine Chemical compound CC1=CC=CN=C1N RGDQRXPEZUNWHX-UHFFFAOYSA-N 0.000 description 1
- ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 description 1
- CMBSSVKZOPZBKW-UHFFFAOYSA-N 5-methylpyridin-2-amine Chemical compound CC1=CC=C(N)N=C1 CMBSSVKZOPZBKW-UHFFFAOYSA-N 0.000 description 1
- 238000006189 Andrussov oxidation reaction Methods 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- 241000640882 Condea Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000005219 aminonitrile group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000001923 cyclic compounds Chemical class 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 239000002638 heterogeneous catalyst Substances 0.000 description 1
- 239000002815 homogeneous catalyst Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 238000002303 thermal reforming Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- 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
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/32—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen
- C07C1/321—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen the hetero-atom being a non-metal atom
- C07C1/323—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen the hetero-atom being a non-metal atom the hetero-atom being a nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/08—Preparation of carboxylic acid nitriles by addition of hydrogen cyanide or salts thereof to unsaturated compounds
- C07C253/10—Preparation of carboxylic acid nitriles by addition of hydrogen cyanide or salts thereof to unsaturated compounds to compounds containing carbon-to-carbon double bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C4/00—Preparation of hydrocarbons from hydrocarbons containing a larger number of carbon atoms
- C07C4/02—Preparation of hydrocarbons from hydrocarbons containing a larger number of carbon atoms by cracking a single hydrocarbon or a mixture of individually defined hydrocarbons or a normally gaseous hydrocarbon fraction
- C07C4/06—Catalytic processes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Description
・触媒A:ジルコニア上に担持したPt(Pt/ZrO2)
・触媒B:シリカ含有率10重量%のシリカ−アルミナ上に付着させた白金(Pt/SiAl10と称する)。
MP:2−メチルペンタン
MPip:3−メチルピペリジン
Pic:ピコリン(β−ピコリン、2−アミノ−3−ピコリン、6−アミノ−3−ピコリン)
%HDN:用いた処理すべき化合物のモル数に対する、窒素原子を含有しない炭化水素生成物の百分率。
・2−メチルグルタロニトリル : 85%
・エチルスクシノニトリル : 11%
・アジポニトリル : 3%
・その他の化合物 : 1%
1MPaの絶対圧下で16ミリリットル/分の水素流量及び1.33kPaのMGN分圧について、例6を繰り返した。これらの条件下で300℃において、%HDNは100%だった。
Claims (9)
- エチレン性不飽和を少なくとも1個含有する有機化合物を触媒系の存在下でヒドロシアン化することによってニトリル官能基を少なくとも1個含有する直鎖状有機化合物を製造するための方法であって、
ヒドロシアン化媒体(群)から利用できるニトリル化合物及び利用できないニトリル副生成物を分離する工程1つ以上を含み、
0.1〜10MPaの範囲の水素絶対圧下で、200℃〜500℃の範囲の温度において、水素化脱窒素触媒の存在下で、水素と反応させることによる水素化脱窒素工程で前記の利用できないニトリル副生成物を処理して該副生成物をアンモニア及び炭化水素化合物に転化させることを含むこと、
ブタジエンのヒドロシアン化によってアジポニトリルを製造することを含むこと、
前記の利用できるニトリル化合物がアジポニトリル、3−ペンテンニトリル、4−ペンテンニトリル、2−メチル−3−ブテンニトリル又はそれらの混合物であること、並びに
前記の利用できないニトリル副生成物がメチルグルタロニトリル、エチルスクシノニトリル、2−ペンテンニトリル、2−メチル−2−ブテンニトリル又はそれらの混合物であること
を特徴とする前記方法。 - 前記水素化脱窒素触媒が白金、パラジウム、ロジウム、ルテニウム及びニッケルより成る群から選択される金属元素であることを特徴とする、請求項1に記載の方法。
- 前記触媒がアルミナ、シリカ、アルミノケイ酸塩、シリカ−アルミナ、活性炭、ジルコニア、酸化チタン及びゼオライトより成る群から選択される担体上に担持された金属元素を含むことを特徴とする、請求項2に記載の方法。
- 前記触媒がジルコニア、シリカ、アルミナ、アルミノケイ酸塩及びシリカ−アルミナより成る群から選択される担体上に付着させた白金を含むことを特徴とする、請求項3に記載の方法。
- 前記の水素絶対圧が0.5MPa〜3MPaの範囲であることを特徴とする、請求項1〜4のいずれかに記載の方法。
- 前記温度が300℃〜400℃の範囲であることを特徴とする、請求項1〜5のいずれかに記載の方法。
- 水素化脱窒素工程の終了時に回収された炭化水素化合物を、アンモニアを除去した後にメタン等の低級アルカンを製造するための水蒸気改質及びメタン化工程において処理することを特徴とする、請求項1〜6のいずれかに記載の方法。
- 前記水蒸気改質及びメタン化工程をニッケルをベースとする担持触媒の存在下で200〜700℃の範囲の温度において5〜50バールの範囲の圧力下で実施することを特徴とする、請求項7に記載の方法。
- アンモニアとメタンとを反応させることによってシアン化水素酸を製造する工程を含むこと、並びに水素化脱窒素工程において生成したアンモニア及び水蒸気改質/メタン化工程において生成したメタンを前記のシアン化水素酸を製造する工程に供給することを特徴とする、請求項1〜8のいずれかに記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR0800255A FR2926549B1 (fr) | 2008-01-18 | 2008-01-18 | Procede de fabrication de composes nitriles |
FR0800255 | 2008-01-18 | ||
PCT/EP2009/050253 WO2009092637A1 (fr) | 2008-01-18 | 2009-01-12 | Procede de fabrication de composes nitriles |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2011511763A JP2011511763A (ja) | 2011-04-14 |
JP5378412B2 true JP5378412B2 (ja) | 2013-12-25 |
Family
ID=39745646
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2010542605A Expired - Fee Related JP5378412B2 (ja) | 2008-01-18 | 2009-01-12 | ニトリル化合物の製造方法 |
Country Status (10)
Country | Link |
---|---|
US (1) | US8373002B2 (ja) |
EP (1) | EP2234921B1 (ja) |
JP (1) | JP5378412B2 (ja) |
KR (1) | KR101235491B1 (ja) |
CN (2) | CN101970355A (ja) |
FR (1) | FR2926549B1 (ja) |
RU (1) | RU2467951C2 (ja) |
TW (1) | TW200948757A (ja) |
UA (1) | UA106467C2 (ja) |
WO (1) | WO2009092637A1 (ja) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7517604B2 (en) * | 2005-09-19 | 2009-04-14 | 3M Innovative Properties Company | Fuel cell electrolyte membrane with acidic polymer |
US7838138B2 (en) * | 2005-09-19 | 2010-11-23 | 3M Innovative Properties Company | Fuel cell electrolyte membrane with basic polymer |
FR2926546A1 (fr) * | 2008-01-18 | 2009-07-24 | Rhodia Operations Sas | Procede de traitement de composes hydrocarbones comprenant des fonctions nitriles ou aminees |
US10995057B2 (en) * | 2016-09-08 | 2021-05-04 | Basf Se | Method for hydrogenating nitriles in the presence of a ruthenium catalyst carried on ZrO2 |
CN107365257B (zh) * | 2017-08-02 | 2019-04-02 | 厦门大学 | 一种2-甲基戊二腈加氢制备2-甲基戊二胺及3-甲基哌啶的方法 |
Family Cites Families (23)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2105831A (en) * | 1934-11-29 | 1938-01-18 | Ig Farbenindustrie Ag | Production of hydrogen cyanide |
US2590146A (en) * | 1949-03-24 | 1952-03-25 | Freeport Sulphur Co | Production of hydrogen cyanide |
US2706675A (en) * | 1950-10-03 | 1955-04-19 | Freeport Sulphur Co | Production of hydrogen cyanide |
US3752839A (en) * | 1970-07-02 | 1973-08-14 | Du Pont | Hydrocyanation olefins |
JPS562919A (en) * | 1979-06-22 | 1981-01-13 | Jgc Corp | Preparation of gas rich in methane |
US4389348A (en) * | 1981-10-26 | 1983-06-21 | Allied Corporation | Selective hydrogenation of dinitrile to omega-aminonitrile and supported rhodium-containing catalyst therefor |
US4591430A (en) * | 1984-05-18 | 1986-05-27 | Exxon Research And Engineering Co. | Process for the denitrogenation of nitrogen-containing hydrocarbon compounds |
US4714773A (en) * | 1987-01-09 | 1987-12-22 | E. I. Du Pont De Nemours And Company | Hydrocyanation of butadiene |
US6162351A (en) * | 1993-02-25 | 2000-12-19 | Texaco Inc. | Hydrodenitrogenation of hydrocarbons utilizing a carbon-supported catalyst |
DE19810484A1 (de) * | 1998-03-11 | 1999-09-16 | Degussa | Verfahren zur Herstellung von Blausäure |
US6221327B1 (en) * | 1998-05-15 | 2001-04-24 | Rohm And Haas Company | Catalyst system using flow-through radiation shielding and a process for producing hydrogen cyanide using the same |
US6380421B1 (en) * | 1999-09-20 | 2002-04-30 | E. I. Du Pont De Nemours And Company | Multidentate phosphite ligands, catalytic compositions containing such ligands and catalytic processes utilizing such catalytic compositions |
ZA200202509B (en) * | 2001-04-06 | 2002-10-24 | Rohm & Haas | Improved process for ammonia recovery. |
FR2829763B1 (fr) * | 2001-09-18 | 2004-12-03 | Rhodia Polyamide Intermediates | Procede de fabrication de composes nitriles |
DE10233931A1 (de) * | 2002-07-25 | 2004-02-05 | Basf Ag | Verfahren zur Herstellung von Cyanwasserstoff durch Oxidation stickstoffhaltiger Kohlenwasserstoffe in einer Flamme |
FR2847898A1 (fr) * | 2002-12-02 | 2004-06-04 | Rhodia Polyamide Intermediates | Procede de fabrication de composes nitriles a partir de composes a insaturation ethylenique |
FR2849027B1 (fr) * | 2002-12-23 | 2005-01-21 | Rhodia Polyamide Intermediates | Procede de synthese de composes comprenant des fonctions nitriles a partir de composes a insaturations ethyleniques |
FR2854892B1 (fr) * | 2003-05-12 | 2005-06-24 | Rhodia Polyamide Intermediates | Procede de fabrication de dinitriles |
FR2854891B1 (fr) * | 2003-05-12 | 2006-07-07 | Rhodia Polyamide Intermediates | Procede de preparation de dinitriles |
FR2857965B1 (fr) * | 2003-07-25 | 2005-08-26 | Rhodia Polyamide Intermediates | Procede de fabrication et de separation de composes dinitriles |
DE102004004721A1 (de) * | 2004-01-29 | 2005-08-18 | Basf Ag | Verfahren zur Trennung von Pentennitril-Isomeren |
DE102004004682A1 (de) * | 2004-01-29 | 2005-08-18 | Basf Ag | Verfahren zur Herstellung von Adipodinitril durch Hydrocyanierung von 1,3-Butadien |
FR2926546A1 (fr) * | 2008-01-18 | 2009-07-24 | Rhodia Operations Sas | Procede de traitement de composes hydrocarbones comprenant des fonctions nitriles ou aminees |
-
2008
- 2008-01-18 FR FR0800255A patent/FR2926549B1/fr not_active Expired - Fee Related
-
2009
- 2009-01-12 CN CN2009801024763A patent/CN101970355A/zh active Pending
- 2009-01-12 RU RU2010134416/05A patent/RU2467951C2/ru not_active IP Right Cessation
- 2009-01-12 JP JP2010542605A patent/JP5378412B2/ja not_active Expired - Fee Related
- 2009-01-12 UA UAA201010207A patent/UA106467C2/uk unknown
- 2009-01-12 CN CN201510526672.0A patent/CN105418457A/zh active Pending
- 2009-01-12 KR KR1020107015910A patent/KR101235491B1/ko not_active IP Right Cessation
- 2009-01-12 EP EP09704303A patent/EP2234921B1/fr not_active Not-in-force
- 2009-01-12 WO PCT/EP2009/050253 patent/WO2009092637A1/fr active Application Filing
- 2009-01-12 US US12/812,891 patent/US8373002B2/en not_active Expired - Fee Related
- 2009-01-17 TW TW098101826A patent/TW200948757A/zh unknown
Also Published As
Publication number | Publication date |
---|---|
RU2010134416A (ru) | 2012-02-27 |
KR20100093126A (ko) | 2010-08-24 |
US8373002B2 (en) | 2013-02-12 |
CN101970355A (zh) | 2011-02-09 |
RU2467951C2 (ru) | 2012-11-27 |
EP2234921A1 (fr) | 2010-10-06 |
UA106467C2 (uk) | 2014-09-10 |
FR2926549A1 (fr) | 2009-07-24 |
FR2926549B1 (fr) | 2015-05-01 |
TW200948757A (en) | 2009-12-01 |
US20110082310A1 (en) | 2011-04-07 |
WO2009092637A1 (fr) | 2009-07-30 |
JP2011511763A (ja) | 2011-04-14 |
CN105418457A (zh) | 2016-03-23 |
KR101235491B1 (ko) | 2013-02-20 |
EP2234921B1 (fr) | 2013-03-13 |
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