US3862911A - Catalyst based on raney nickel containing iron - Google Patents

Catalyst based on raney nickel containing iron Download PDF

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Publication number
US3862911A
US3862911A US314434A US31443472A US3862911A US 3862911 A US3862911 A US 3862911A US 314434 A US314434 A US 314434A US 31443472 A US31443472 A US 31443472A US 3862911 A US3862911 A US 3862911A
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weight
nickel
catalyst
iron
alloy
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US314434A
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Henri Chabert
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Rhone Poulenc SA
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Rhone Poulenc SA
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/44—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers
    • C07C209/48—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers by reduction of nitriles
    • 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
    • B01J25/00—Catalysts of the Raney type
    • B01J25/02—Raney nickel

Definitions

  • the present invention relates to a hydrogenation'catalyst based on a Raney nickel which also contains iron and chromium. This catalyst is particularly valuable for hydrogenating unsaturated groups.
  • the Raney catalysts containing chromium contain small amounts of iron, they nevertheless possess disadvantages in certain applications.
  • the speed of hydrogenation is relatively slow.
  • the termination period is long (the termination period is the time interval which separates the end of injection of the nitrile and the end of absorption of hydrogen).
  • Raney catalysts containing chromium did not prevent the formation of a relatively large amount of by-products.
  • the present invention provides new hydrogenation catalysts based on Raney nickel, which substantially avoid the above mentioned disadvantages.
  • the catalysts of the present invention are those prepared by treating an alloy powder with an alkali, the composition of the alloy being, by weight, limits:
  • the residue being aluminium.
  • the alloy will also contain conventional impurities and other incidental ingredients.
  • Alloys in the powder form can be obtained by crushing and grinding alloy ingots, the latter being prepared by the usual metallurgical techniques, forcxample, by adding nickel, iron and chromium to molten aluminium, preferably heated to between 900 and l,O0OC.
  • Iron and chromium can be introduced either in the form of pure metals or in the form of their alloys with aluminium. It is possible to use nickel which is obtained either by conventional smelting of nickel from garnierit (nickel magnesium silicate dihydrate) or from nickelbearing pyrites, or by decomposition of nickel carbonyl.
  • alloy is ground and passed through a sieve before being treated with the alkali.
  • the sieved alloy is in the form oifa powder, the particle size of which is normally less than 500 microns.
  • a powder of particle size less than 50 microns is preferably used.
  • the process conditions for treating the powder can be very diverse, it being possible to carry out this treatment using an inorganic or organic base.
  • the treatment is usually carried out at a temperature of 40 l 10C. It is possible to add the alloy powder to the basic solution, or to pour the basic solution onto the alloy or to pour an aqueous suspension of the alloy into the base. When the alloy and base'have been mixed, the reaction is continued until hydrogen ceases to be evolved, this occurs usually within 3 hours.
  • the resulting catalyst is washed with water, by a continuous or discontinuous method, which optionally may take place under a slight pressure: of hydrogen.
  • the product may optionally be washed with an alcoholic solution, the alcohol usually being ethanol.
  • the resulting catalyst is pyrophoric, and it is necessary to store it out of contact with air, for example under water, or a liquid alcohol or hydrocarbon.
  • the finished catalysts after treatment with base will normally contain nickel, aluminium, chromium and iron in the following proportions:
  • the catalysts of the invention can be used for hydrogenating various hydrogenisable organic substances, but they are particularly recommended for hydrogenating mono-functional or poly-functional unsaturated groups of the olefinic type or of the nitrile type. It was found, particularly with regard to the reaction for bydrogenating dinitriles, that the speed of hydrogenation was more rapid and that the termination periods were decreased. Furthermore, the formation of by-products takes place to a lesser extent and the catalysts can be re-cycled more times because of their better resistance to fatigue. These advantages are particularly marked for the hydrogenation of adiponitrile, wherein, in addition, a diamine is obtained which contains fewer unsaturated impurities than those prepared using previous catalysts.
  • the polyamide fibres derived The hydrogenation can be carried out optionally in the presence of a solvent such as a lower alkanol e g. containing up to 4 carbon atoms. It is also possible to activate the Raney catalysts using small proportions of an alkaline agent introduced. for example. in the form of an aqueous solution.
  • EXAMPLE 1 A Preparation of the catalyst 448g of aluminium are melted in a graphite crucible and 31g of iron powder, 7g of chromium powder and 214g of compressed nickel (a trade name for billets of cylindrical shape, diameter 30 mm, height mm; these billets are broken up into pieces before use) are added to the aluminium which is heated to 950C. The mixture is stirred with a graphite rod and it is found that the temperature rises to 1,500C. The cooled alloy is removed from the mould, cut up into shavings, finely ground and passed through a sieve and 180g of a powder, the particle size of which is less than 50 microns, are collected. The additional amount to make up 700g represents the portion which is greater than 50 microns and the grinding losses.
  • This powder has the following composition:
  • iron 3% aluminium 56g of this powder is then treated with alkali by introducing the powder in small portions into 326 cm of a by weight aqueous solution of sodium hydroxide.
  • the temperature is kept at 75C.
  • the termination period is 8 minutes.
  • a catalyst was prepared from a Raney alloy containing chromium and iron. with a small content of iron, in the following way:
  • the additional amount to make up 1,504g consists of the portion greater than 50 microns and grinding losses.
  • the alkali treatment is carried out by adding 38.6g of alloy of particle size between 0 and 50 microns to 306 cm" of an aqueous solution containing 27.7% by weight sodium hydroxide. After the end of the addition of the alloy, the treatment with alkali is continued for 55 minutes and then, after cooling, the catalyst is washed, by shaking followed by decanting, with:
  • the resulting catalyst contains 18.7g Ni, 0.38g Cr, 0.23g Fe and 1.9g Al, that is to say Cr/Ni 2%, Fe/Ni 1.2% and Al/Ni 10% by weight.
  • Example 2 Catalysts were prepared according to the method described in Example 1 part A from alloys, the composition of which is given in the following table. The hydrogenation of adiponitrile to hexamethylenediamine is carried out in the same way as that described in Example 1 part B. The termination periods are also given in the table. It should be noted that they are less than those obtained with a catalyst which does not contain iron.
  • the treatment and the washing are analogous to Fe/Ni 8% by weight and 7 2 g. A! giving Al/Ni those described in Examples 1 partA and 2.
  • the result- 9 ing catalyst contains 37.5 g. of nickel, the proportions fh d of the various metals being as follows: Al/Ni 13.8%; This catalyst 15 used to carry out a series 0 y roge- Fe/Ni 7% and Cr/Ni 12% nations by the method described in Example 1 part B.
  • a catalyst was used 7 which contains a small content of iron and was prepared from the alloy powder described in Example I. the composition of which is as follows:
  • the treatment with alkali is carried out by adding 77.2 g. of this alloy of particle size less than 50 microns to 712 cm of an aqueous solution containing 27.7% by weight sodium hydroxide.
  • a catalyst consisting of 37.5 g. of nickel, aluminium, iron and chromium in the following proportions: Al/Ni 10.571; Cr/Ni 2% and Fe/Ni 1.2%, is obtained after the end of treatment, washing and decanting, as described in the previous Examples.
  • This catalyst is used to hydrogenate adiponitrile by the procedure described in part A of this Example.
  • the termination period is 9.5 minutes.
  • the proportion of residue is 5.6%.
  • EXAMPLE A Preparation of the catalyst 462 g. of aluminium are melted in a graphite crucible and 21 g. of iron powder, 3.5 g. of chromium powder and 214 g. of compressed nickel are added to the aluminium which has been heated to 900C. The mixture is stirred with a graphite rod and it is found that the temperature rises to l,500C. The cooled alloy is removed from the mould, cut up into shavings, finely ground and the fraction passing through a 50 microns sieve collected. The additional amount to make up 700 g. represents the portion greater than 50 microns and the grinding losses.
  • This powder has the following composition:
  • the duration of hydrogenation is 140 minutes.
  • Example 4 part B When the catalyst containing chromium and a small amount of'iron as described in Example 4 part B is used, the duration of hydrogenation is 44v minutes, the yield of the diamine is 62% and the proportion of residue is 30%.
  • the residual alloy contains:

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  • 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)
  • Catalysts (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
US314434A 1971-12-13 1972-12-12 Catalyst based on raney nickel containing iron Expired - Lifetime US3862911A (en)

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Application Number Priority Date Filing Date Title
FR7144626A FR2164959A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) 1971-12-13 1971-12-13

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JP (1) JPS4866087A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
BE (1) BE792649A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
BR (1) BR7208752D0 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
CA (1) CA992103A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
CH (1) CH564372A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
DD (1) DD101566A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
DE (1) DE2260978A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
FR (1) FR2164959A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
GB (1) GB1397576A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
IT (1) IT971820B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
LU (1) LU66633A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
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Cited By (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3997478A (en) * 1974-10-07 1976-12-14 Budapesti Muszki Egyetem Promted Raney-nickel catalysts
US4800139A (en) * 1984-12-27 1989-01-24 Muroran Institute Of Technology Method of producing hydrogen electrode and use thereof in fuel cells
WO1995018090A1 (fr) * 1993-12-28 1995-07-06 Rhone-Poulenc Chimie Procede d'hydrogenation catalytique de nitriles en amines en presence d'un catalyseur de type nickel de raney dope
US5464699A (en) * 1988-04-18 1995-11-07 Alloy Surfaces Co. Inc. Pyrophoric materials and methods for making the same
EP0807464A1 (en) * 1996-04-15 1997-11-19 Dairen Chemical Corporation A modified raney nickel catalyst and a process for preparing diols by using the same
US5886189A (en) * 1990-01-31 1999-03-23 Eastman Kodak Company Manufacture of aromatic amines
US6147247A (en) * 1996-09-10 2000-11-14 Basf Aktiengesellschaft Process for simultaneously preparing 6-aminocapronitrile and hexamethylene diamine
US6147208A (en) * 1995-12-22 2000-11-14 Basf Aktiengesellschaft Process for simultaneously preparing caprolactam and hexamethylene diamine
US6265451B1 (en) * 1999-09-21 2001-07-24 Hydrocarbon Technologies, Inc. Skeletal iron catalyst and its preparation for Fischer-Tropsch synthesis processes
US6277895B1 (en) * 1999-09-21 2001-08-21 Hydrocarbon Technologies, Inc. Skeletal iron catalyst having improved attrition resistance and product selectivity in slurry-phase synthesis processes
US6368996B1 (en) * 1999-04-29 2002-04-09 China Petroleum Corporation Hydrogenation catalyst and its preparation
US20030120116A1 (en) * 1999-07-08 2003-06-26 Daniel Ostgard Fixed-bed Raney-type catalysts
KR100420453B1 (ko) * 1998-11-05 2004-03-02 이 아이 듀폰 디 네모아 앤드 캄파니 라니 철 촉매 및 이 촉매를 사용한 유기 화합물의 수소화방법
US20040249214A1 (en) * 2003-06-05 2004-12-09 Amey Ronald L. Low pressure process for the manufacture of 2-(aminomethyl)-1-cyclopentylamine
US20050065024A1 (en) * 2003-09-23 2005-03-24 Haiyou Wang Catalyst for the generation of CO-free hydrogen from methane
US20050063900A1 (en) * 2003-09-23 2005-03-24 Haiyou Wang CO-free hydrogen from decomposition of methane
WO2006089931A1 (de) * 2005-02-24 2006-08-31 Basf Aktiengesellschaft Verfahren zur herstellung eines xylylendiamins
US20080015267A1 (en) * 2006-07-14 2008-01-17 Headwaters Nanokinetix, Inc. Fischer-tropsch catalysts incorporating promoter for increasing yields of c5+ hydrocarbons and methods for making and using same
US20080214871A1 (en) * 2005-01-24 2008-09-04 Basf Aktiengesellschaft Method For Producing A Xylylene Diamine
WO2008107236A1 (de) * 2007-03-07 2008-09-12 Evonik Degussa Gmbh Verfahren zur herstellung von trimethylhexamethylendiamin
WO2008107226A1 (de) * 2007-03-07 2008-09-12 Evonik Degussa Gmbh Verfahren zur herstellung von 3-aminomethyl-3,5,5-trimethylcyclohexylamin

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
HU176794B (en) * 1978-06-03 1981-05-28 Chinoin Gyogyszer Es Vegyeszet Process for producing alloy of aluminium of high reducing activity,containing discontinual heterodisperz alloy on the surface
US4607104A (en) * 1985-07-11 1986-08-19 Uniroyal Chemical Company, Inc. Process for the production of 2,2,6,6-tetraalkyl-4-piperidylamines
JP2009106923A (ja) * 2007-10-29 2009-05-21 Emmellen Biotech Pharmaceuticals Ltd 接触水素化方法及びそのための新規触媒
FR2944789B1 (fr) * 2009-04-22 2011-05-20 Rhodia Operations Procede de preparation d'un terpenylcyclohexanol

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2502348A (en) * 1944-11-20 1950-03-28 Rhone Poulenc Sa Catalysts
US3235513A (en) * 1961-02-07 1966-02-15 Varta Ag Process for activating raney alloys and solution useful for such process
US3544485A (en) * 1967-10-16 1970-12-01 Toray Industries Method of activating catalytic alloys
US3682709A (en) * 1967-12-04 1972-08-08 Allis Chalmers Mfg Co Process for improving nickel base,nonnoble metal fuel cell catalysts

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR913997A (fr) * 1944-11-20 1946-09-25 Rhone Poulenc Sa Nouveaux catalyseurs

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2502348A (en) * 1944-11-20 1950-03-28 Rhone Poulenc Sa Catalysts
US3235513A (en) * 1961-02-07 1966-02-15 Varta Ag Process for activating raney alloys and solution useful for such process
US3544485A (en) * 1967-10-16 1970-12-01 Toray Industries Method of activating catalytic alloys
US3682709A (en) * 1967-12-04 1972-08-08 Allis Chalmers Mfg Co Process for improving nickel base,nonnoble metal fuel cell catalysts

Cited By (30)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3997478A (en) * 1974-10-07 1976-12-14 Budapesti Muszki Egyetem Promted Raney-nickel catalysts
US4800139A (en) * 1984-12-27 1989-01-24 Muroran Institute Of Technology Method of producing hydrogen electrode and use thereof in fuel cells
US5464699A (en) * 1988-04-18 1995-11-07 Alloy Surfaces Co. Inc. Pyrophoric materials and methods for making the same
US5886189A (en) * 1990-01-31 1999-03-23 Eastman Kodak Company Manufacture of aromatic amines
US5777166A (en) * 1993-12-28 1998-07-07 Rhone-Poulenc Chimie Process for the catalytic hydrogenation of nitriles to amines in the presence of a catalyst of doped raney nickel type
WO1995018090A1 (fr) * 1993-12-28 1995-07-06 Rhone-Poulenc Chimie Procede d'hydrogenation catalytique de nitriles en amines en presence d'un catalyseur de type nickel de raney dope
US6147208A (en) * 1995-12-22 2000-11-14 Basf Aktiengesellschaft Process for simultaneously preparing caprolactam and hexamethylene diamine
EP0807464A1 (en) * 1996-04-15 1997-11-19 Dairen Chemical Corporation A modified raney nickel catalyst and a process for preparing diols by using the same
US6147247A (en) * 1996-09-10 2000-11-14 Basf Aktiengesellschaft Process for simultaneously preparing 6-aminocapronitrile and hexamethylene diamine
KR100420453B1 (ko) * 1998-11-05 2004-03-02 이 아이 듀폰 디 네모아 앤드 캄파니 라니 철 촉매 및 이 촉매를 사용한 유기 화합물의 수소화방법
US6368996B1 (en) * 1999-04-29 2002-04-09 China Petroleum Corporation Hydrogenation catalyst and its preparation
US20030120116A1 (en) * 1999-07-08 2003-06-26 Daniel Ostgard Fixed-bed Raney-type catalysts
US6265451B1 (en) * 1999-09-21 2001-07-24 Hydrocarbon Technologies, Inc. Skeletal iron catalyst and its preparation for Fischer-Tropsch synthesis processes
US6277895B1 (en) * 1999-09-21 2001-08-21 Hydrocarbon Technologies, Inc. Skeletal iron catalyst having improved attrition resistance and product selectivity in slurry-phase synthesis processes
US20040249214A1 (en) * 2003-06-05 2004-12-09 Amey Ronald L. Low pressure process for the manufacture of 2-(aminomethyl)-1-cyclopentylamine
US6924394B2 (en) * 2003-06-05 2005-08-02 Invista North America S.R.L. Low pressure process for the manufacture of 2-(aminomethyl)-1-cyclopentylamine
US20050065024A1 (en) * 2003-09-23 2005-03-24 Haiyou Wang Catalyst for the generation of CO-free hydrogen from methane
US20050063900A1 (en) * 2003-09-23 2005-03-24 Haiyou Wang CO-free hydrogen from decomposition of methane
WO2005030391A1 (en) * 2003-09-23 2005-04-07 Catalytic Materials, Llc Catalyst and method for the generation of co-free hydrogen from methane
US6995115B2 (en) * 2003-09-23 2006-02-07 Catalytic Materials, Llc Catalyst for the generation of CO-free hydrogen from methane
US7001586B2 (en) * 2003-09-23 2006-02-21 Catalytic Materials, Llc CO-free hydrogen from decomposition of methane
US20080214871A1 (en) * 2005-01-24 2008-09-04 Basf Aktiengesellschaft Method For Producing A Xylylene Diamine
US20080154061A1 (en) * 2005-02-24 2008-06-26 Basf Aktiengesellschaft Method For Producing a Xylylenediamine
WO2006089931A1 (de) * 2005-02-24 2006-08-31 Basf Aktiengesellschaft Verfahren zur herstellung eines xylylendiamins
US20080015267A1 (en) * 2006-07-14 2008-01-17 Headwaters Nanokinetix, Inc. Fischer-tropsch catalysts incorporating promoter for increasing yields of c5+ hydrocarbons and methods for making and using same
US7709541B2 (en) 2006-07-14 2010-05-04 Headwaters Technology Innovation, Llc Fischer-Tropsch catalysts incorporating promoter for increasing yields of C5+ hydrocarbons and methods for making and using same
WO2008107236A1 (de) * 2007-03-07 2008-09-12 Evonik Degussa Gmbh Verfahren zur herstellung von trimethylhexamethylendiamin
WO2008107226A1 (de) * 2007-03-07 2008-09-12 Evonik Degussa Gmbh Verfahren zur herstellung von 3-aminomethyl-3,5,5-trimethylcyclohexylamin
US20100041921A1 (en) * 2007-03-07 2010-02-18 Evonik Degussa Gmbh Process for preparing 3-aminomethyl-3,5,5-trimethylcyclohexylamine
US8003826B2 (en) 2007-03-07 2011-08-23 Evonik Degussa Gmbh Method for production of trimethylhexamethylenediamine

Also Published As

Publication number Publication date
GB1397576A (en) 1975-06-11
FR2164959A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) 1973-08-03
CA992103A (fr) 1976-06-29
BR7208752D0 (pt) 1973-09-25
SU450387A3 (ru) 1974-11-15
IT971820B (it) 1974-05-10
BE792649A (fr) 1973-06-12
JPS4866087A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) 1973-09-11
DD101566A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) 1973-11-12
CH564372A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) 1975-07-31
NL7216479A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) 1973-06-15
LU66633A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) 1973-07-18
DE2260978A1 (de) 1973-06-20

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