Hydration of aliphatic nitriles to amides using copper metal catalysts

Aliphatic nitriles are converted to the corresponding amides by contacting the nitrile in the presence of water with a cupreous catalyst containing copper metal.

In our prior application, we reported the discovery that copper metal in 
the proper form is a very effective catalyst for the conversion of 
nitriles to amides. In discussing the copper catalyst, we stated: 
The copper catalyst of the invention may be any conventional form of 
copper. Such copper metal catalysts may be purchased commercially or 
prepared by a number of known methods. Suitably such copper catalysts may 
be prepared by reducing copper oxide, by decomposing and reducing copper 
salts, such as, copper acetate, copper carbonate, copper hydroxide and 
copper oxalate or by reducing other copper salts, such as, copper halide, 
copper nitrate and copper sulfate. Copper catalysts prepared by reducing 
copper oxide are preferred. 
BACKGROUND OF THE INVENTION 
Hydration of nitriles in the presence of water has been accomplished by a 
number of copper catalysts. For example, Greene in U.S. 3,381,034 reacted 
various nitriles with water in the presence of soluble copper ions. The 
present invention is distinguished over this art because the catalysts of 
the invention contain catalytic copper metal. In contrast, Greene used 
massive copper metal to make her catalysts and stated that this metal was 
not catalytic. 
Watanabe in Bull. Chem. Soc. Japan, 32, 1280 (1959); 37, 1325 (1964); and 
39, 8 (1966) shows the use of reduced copper chloride, a catalyst useful 
in the present invention. His catalysts were prepared by contacting copper 
chloride with zinc and were employed only to convert benzonitrile to 
benzamide. In contrast, the present invention converts aliphatic nitriles 
to the corresponding amide. Watanabe in Bull. Chem. Soc. Japan, 37, in the 
left column of p. 1325 makes the broad statement that "[the] reaction of 
aliphatic nitriles is somewhat complicated and is different from that of 
aromatic ones: the yield of the amides is comparatively lower than that 
from aromatic nitriles, and the hydration reaction is accompanied by side 
reactions forming some acidic compounds." Although this general statement 
is apparently based on work done with nickel catalysts, it would be 
expected that similar results would be obtained with copper compounds. 
Contrary to this expected result, it has been found that for catalysts 
which contain catalytic copper, the reaction forms litle or no 
by-products. 
SUMMARY OF THE INVENTION 
It has now been discovered according to the present invention that 
aliphatic nitriles are hydrated to the corresponding amide by contacting 
the nitrile in the presence of water with a cupreous catalyst containing a 
catalytic amount of copper. 
The central aspect of the present invention is that copper metal is 
catalytic in the conversion of aliphatic nitriles to the corresponding 
amides and that such reactions give little or no by-products. As noted in 
our previous application, this catalytic copper may take essentially any 
form so long as it catalyzes the conversion of the nitrile. 
Our previous applications show various methods of obtaining catalytic 
copper. For example, our prior applications Ser. No. 835,765, filed June 
23, 1969, and Ser. No. 157,647, filed June 28, 1971, show methods of 
obtaining catalytic copper by reducing copper oxide to copper metal. Our 
prior applications, Ser. No. 835,765, filed June 23, 1969, and Ser. No. 
157,648, filed June 28, 1971, show that active copper catalysts are 
conveniently prepared by reducing copper hydroxide or a copper salt to 
copper metal using a suitable reducing agent. Thus, in our prior 
applications we have shown that copper metal catalysts which have 
practical activity in the conversion of nitriles to amides can be 
prepared. 
From these data and disclosures, it would be well known to one of ordinary 
skill that there are numerous equivalent methods of preparing an active 
copper catalyst. This is true because the attributes of the copper 
catalysts prepared by the methods above are known. A prime attribute of 
these practical catalysts is high surface area. Catalysts having a surface 
area of greater than 0.2 square meter per gram are preferred, with those 
catalysts having a surface area of at least about 0.5 square meters per 
gram being of special interest because of their high activity and the 
desirable reaction obtained. Thus, methods of preparing catalysts of high 
surface area would be known to be applicable to these copper catalysts 
described. 
Many active copper catalysts are available commercially. For example, in 
our prior applications, a large number of copper containing catalysts were 
purchased commercially and then treated, normally by reduction, to obtain 
an active copper catalyst. Also available at the time of our prior 
applications were other commercial preparations that could be transformed 
into active copper metal catalysts having high surface area. For example, 
alloys of aluminum and copper were available from which could be made high 
surface area copper catalysts known as Raney copper. These catalysts are 
normally prepared by leaching out the aluminum with strong base to leave a 
finely divided copper metal. 
In our prior application claiming copper, all of these methods of obtaining 
catalytic copper are covered under the generic term "copper." A prime 
facet of our basic discovery at that juncture was that copper and reduced 
copper compounds are especially active catalysts for the conversion of 
aliphatic nitriles to the corresponding amide without significant amounts 
of by-product. 
To summarize and amplify on our prior work, active copper catalysts are 
prepared by reducing copper oxide, by reducing copper hydroxide or a 
copper salt and by other known techniques. These three categories are 
discussed in detail below. 
Copper catalysts from copper oxide 
In the preparation of copper catalysts from copper oxide, the copper oxide 
may be cupric oxide, cuprous oxide or a mixture of the two. These copper 
oxide starting materials are usually obtained commercially or they may be 
prepared by the decomposition and/or reduction of other copper compounds, 
such as copper hydroxide, copper carbonate, copper acetate, copper 
oxalate, copper nitrate and the like. Any such method of obtaining the 
copper oxide starting material is acceptable. 
To prepare the active copper catalysts of the invention from copper oxide, 
the copper oxide is contacted with a reducing agent under conditions which 
cause the oxide to be reduced to copper metal. The most convenient method 
of obtaining an active catalyst is a hydrogenation using temperatures of 
about 100.degree. to about 350.degree. C. Although reduction with hydrogen 
is preferred, other reducing agents, such as sodium borohydride, hydrazine 
and aluminum hydride, are also conveniently employed. 
Copper catalysts prepared from copper hydroxide or a copper salt 
The copper catalysts of the invention prepared from copper hydroxide or a 
copper salt are prepared in much the same manner as shown for the 
preparation of copper catalysts from copper oxide. Some of the copper 
salts, however, require more strenuous conditions of reduction to obtain a 
desirable copper metal catalyst. 
Representative examples of copper salts that can be reduced to copper to 
give a desirable catalyst include: copper salts having nitrogen-containing 
anions, such as copper nitrate, copper nitrite, copper nitride, copper 
cyanide, copper nitroprusside and copper ferrocyanide; copper salts having 
halogen-containing anions, such as copper chloride, copper bromide, copper 
perchlorate, copper bromate and copper iodide; copper salts having 
sulfur-containing anions, such as copper sulfide, copper sulfate, copper 
sulfite and copper thiocyanate; copper salts having organic carboxylic 
acid-containing anions, such as copper carbonate, copper acetate, copper 
oxalate, copper butyrate, copper citrate, copper formate, copper benzoate 
and copper laurate; and other copper salts, such as copper borate, copper 
phosphate, copper carbide, copper chromate and copper tungstate. 
Preferred catalysts are obtained by reducing copper hydroxide or copper 
salts having anions containing nitrogen, sulfur or organic carboxylic 
acids, with copper nitrate, copper acetate, copper carbonate, copper 
oxalate, copper sulfide, copper chloride and copper hydroxide being of 
special interest. 
In the reduction of copper hydroxide or a copper salt to produce a copper 
catalyst, the interrelationship of temperature, time, and nature and 
amount of reducing agent determines the extent of the reduction. For 
example, in a preferred hydrogen reduction, the temperature may range from 
about 50.degree. to about 500.degree. C. or more, with temperatures of 
about 150.degree. to about 350.degree. C. being preferred. Unnecessarily 
high temperatures have a tendency to reduce the activity of the resulting 
catalysts. The time and quantity are preferably adjusted to give 
essentially complete reduction to catalytic copper metal. 
Although reduction of the copper salt with hydrogen to produce a copper 
catalyst is convenient, other reducing agents may also be employed. For 
example, the catalyst may be prepared by contacting the salt under the 
appropriate conditions with hydrazine, carbon, carbon monoxide, NH.sub.2 
OH, NaBH.sub.4, Na.sub.2 S.sub.2 O.sub.4, a lower alkane or a lower 
alkanol or other reducing agent. Preferred liquid phase reducing agents 
are NaBH.sub.4 and hydrazine. 
As examples of reductions of the invention, copper catalysts are prepared 
by contacting under aqueous conditions a soluble copper salt, such as 
CuCl.sub.2, CuBr.sub.2, Cu(NO.sub.3).sub.2, Cu(ClO.sub.3).sub.2, copper 
oxalate, copper formate, copper acetate, Cu(NH.sub.3).sub.4 S.sub.2 
O.sub.6, Cu(NH.sub.3).sub.4 CrO.sub.4 or Cu(OH).sub.2 with a reducing 
agent such as NH.sub.2 OH, NaBH.sub.4, N.sub.2 H.sub.4, Na.sub.2 S.sub.2 
O.sub.4 or an active metal such as zinc. Also, under anhydrous conditions, 
copper hydroxide or any copper salt, such as CuC.sub.2, 
Cu(ClO.sub.3).sub.2, copper formate, copper acetate, CuCl.sub.2, 
CuBr.sub.2, Cu(NO.sub.3).sub.2, CuC.sub.2 O.sub.4, copper stearate, copper 
tartrate, CuS, 
EQU Cu(NH.sub.3).sub.4 CrO.sub.4 
or Cu(NH.sub.3).sub.4 S.sub.2 O.sub.6 are reduced by contact with a 
reducing agent, such as hydrogen. The optimum conditions for such 
reductions vary widely as different salts and reducing agents are 
employed. 
Other preparations of copper catalysts 
As noted above, the thrust of the present invention is the discovery that 
copper metal is an active catalyst that can convert aliphatic nitriles to 
the corresponding amide with little or no by-products. From this 
discovery, the specific manner of preparing the catalyst is relatively 
straightforward. 
One of the most notable of the methods of preparing a catalyst with a high 
surface area is to use the Raney technique which is normally associated 
with preparing Raney nickel. Raney copper can be prepared by similar 
techniques. Commercial formulations which can be used to prepare these 
catalysts are readily available, for example, an alloy of aluminum and 
copper is available from W. R. Grace and Co. Such catalysts are developed 
or activated by known techniques to give the active copper catalysts of 
the invention. Normally such techniques involve contacting the alloy with 
a strong base under conditions which leach out the aluminum. 
In addition to the use of copper metal as Raney copper, other copper 
catalysts can be devised. For example, a piece of copper metal, which 
Greene et al. have shown is noncatalytic, is made catalytic by heating the 
metal in air and then contacting it with a reducing agent. Also, active 
catalysts may be prepared by grinding copper metal to a very fine powder. 
Moreover, other techniques are now known or can be conceived which can be 
used to prepare the active copper catalysts of the invention. 
In summary, numerous techniques can be used to prepare copper catalysts 
which convert nitriles to the corresponding amide with little or no 
by-products. 
The precise point of the present invention is the use of these active 
copper metal catalysts in the hydration of aliphatic nitriles. The process 
parameters in the catalytic hydrolysis are broadly known. Nonetheless, 
their clarification and explanation would be helpful to give the optimum 
benefit from the invention. 
Of course, the copper catalysts of the invention may be used alone or in 
combination with other materials. For example, the copper metal catalyst 
may be mounted on an inert support, it may be used in combination with 
other inert materials or it may be used in combination with other 
materials that are catalytic in the process. The important aspect of the 
invention, however, is that the catalyst contains catalytic copper. 
An important factor in the use of the copper catalyst is the liability of 
the catalyst to deactivation upon exposure to oxygen. This contact is 
usually encountered after the active catalyst is prepared by contact with 
the atmosphere or by contact with feed solutions which contain dissolved 
oxygen. Thus, in the preferred practice of the process, this deleterious 
contact with oxygen prior to or during the hydration is avoided. Such 
precautions are taken by protecting the catalyst from contact with an 
oxygen-containing gas after activation and by removing substantially all 
of the dissolved oxygen from the feed stream of nitrile and water. 
Any aliphatic nitrile may suitably be used in the present invention, with 
hydrocarbon nitriles containing up to about 20 or more carbon atoms being 
preferred. Representative examples of suitable nitriles include: saturated 
aliphatic hydrocarbon nitriles such as acetonitrile, propionitrile, 
pentanonitrile, dodecanonitrile, succinonitrile, adiponitrile and the 
like; and unsaturated aliphatic hydrocarbon nitriles such as 
acrylonitrile, methacrylonitrile, crotonic nitrile, 
.beta.-phenylacrylonitrile, 2-cyano-2-butene, 1-cyano-1-octene, 
10-undecenonitrile, maleonitrile, fumaronitrile. Of the nitriles suitable 
for use in the invention, the olefinic nitriles of 3 to 6 carbon atoms are 
especially preferred, with the conversion of acrylonitrile to acrylamide 
being of special interest. 
The proportions of nitrile to water in the reactant mixture may vary widely 
because any amount of water that gives the hydration is acceptable. More 
important than the specific nitrile to water ratio is the extent of the 
interaction between the nitrile and water. A high degree of contact is 
desirable to assure the greatest efficiency in the reaction. For gaseous 
reactants, the nitrile and water are miscible in all proportions, but for 
liquid reactants, certain precautions may be helpful to insure that 
intimate contact of the nitrile and water is maintained. The necessary 
contact may be realized by dissolving the nitrile in the water or by 
dissolving the water in the nitrile. Outside of the limits of the 
solubility of one of the reactants in the other, however, the reactant 
mixture may be agitated, a suitable solvent may be added or another means 
of increasing the contact of the reactants may be employed. Excess water 
is the preferred solvent although other inert solvents, such as alkanols, 
dioxane, dimethyl sulfoxide, acetone, dimethyl ether of ethylene glycol or 
tetrahydrofuran, may also be used. 
The copper metal catalysts of the invention are convenient to use in both a 
batch process and a continuous flow process. Using either method, the 
nitrile and water are contacted with the catalyst under the appropriate 
reaction conditions, and the amide product is then recovered. Since the 
catalysts of the present invention are normally employed as essentially 
insoluble heterogeneous catalysts, a continuous flow reaction is 
preferred. For catalysts which are powders, a countercurrent flow reactor 
might be preferred. 
In a continuous flow reaction using a fixed bed reactor, the solid catalyst 
of the invention is packed into a reaction chamber having an inlet for 
reactants and an outlet for products. The reaction chamber is maintained 
at the desired reaction temperature and the rate of flow of reactants over 
the catalyst is controlled to give the desired contact of the reactants 
with the catalyst. The reactants may be fed over the solid catalyst as a 
gas or, preferably, as a liquid. The reaction product from the reactor may 
be used as such or purified by any known technique. 
The temperature of the reaction may vary widely as different nitriles are 
used in the invention. Generally, the reaction is conducted within a 
temperature range of about 0.degree. to about 400.degree. C. At 
temperatures below this level, the reaction is impractically slow. Above 
this range, the reaction forms an increasing amount of undesirable 
by-products. Within the broad temperatures range and when operating in the 
liquid phase, temperatures of about 25.degree. to about 200.degree. C. are 
preferred. For unsaturated nitriles which tend to polymerize, a reaction 
temperature of less than about 200.degree. C., the use of polymerization 
inhibitors or dilute reaction solutions are desirable to avoid 
polymerization of the nitrile and possible poisoning of the catalyst. 
The other reaction conditions are known in the art of using heterogeneous 
catalysts and are not critical in the invention. The important aspect of 
the invention is the use of the cupreous catalyst containing copper to 
convert nitriles to the corresponding amides.

SPECIFIC EMBODIMENTS 
Example 1.--Use of a copper catalyst prepared by reducing copper oxide 
A copper catalyst was prepared by reducing 20 grams of a catalyst 
containing 99% CuO sold under the trade name Harshaw Cu0307. The reduction 
was conducted at 250.degree. C. for 4 hours using a gaseous stream 
containing 130 cc./min. of H.sub.2 and 510 cc./min. of N.sub.2. A 15 cc. 
reactor was packed with 19 g. of the activated catalyst, and the reactor 
was held at 80.degree. C. The reactor was run continuously using a 14 
cc./hr. flow of 7% acrylonitrile in water. Over two weeks of continuous 
operation, the conversion of acrylonitrile decreased from 75% to 33%, the 
yield of acrylamide was essentially constant at 91% and the yield of 
.beta.-hydroxypropionitrile decreased from 3 to 1%. Oxygen was not 
excluded from the feed stream. 
Examples 2-6 and Comparative Example A.--Copper prepared by the reduction 
of copper oxide with NaBH.sub.4 
Copper oxide pellets sold under the trade name Harshaw CuXL 112A-17-8-2 and 
measuring 1/8".times.1/8" were reduced with an aqueous solution of 
NaBH.sub.4. About 8 g. of copper oxide pellets and 200 cc. of a solution 
of NaBH.sub.4 were contacted for a period of one hour with agitation. The 
NaBH.sub.4 concentration, pH and temperature of the reduction are shown in 
Table I along with a catalyst washed with only water for comparison. The 
NaBH.sub.4 is basic in water; the acid pH were obtained by adding 
concentrated HCl to the NaBH.sub.4 solution. The catalysts were tested by 
charging one gram of the pellets into a glass ampoule along with 5 cc. of 
a 7% aqueous solution of acrylonitrile. The acrylonitrile was reacted in 
the presence of the catalyst for one hour at 100.degree. C. The results of 
these experiments are shown in Table I. No .beta.-hydroxypropionitrile or 
other by-products were found. 
TABLE I 
______________________________________ 
Hydration of acrylonitrile using 
catalysts prepared by reducing copper 
oxide with NaBH.sub.4 
Copper oxide reduction 
Hydration, 
NaBH.sub.4, Temp., percent 
Example molar pH .degree.C. 
Conv. Yield 
______________________________________ 
Comparison A 
0 Neutral 25 24 57 
2 0.25 Basic 25 78 84 
3 0.50 " 25 89 83 
4 0.50 Acid 25 68 86 
5 0.50 Basic 90 83 93 
6 0.50 Acid 90 53 70 
______________________________________ 
Examples 7-17.--Copper prepared by reducing copper salts with hydrogen 
A number of copper catalysts were prepared by heating about 20 g. of a 
copper salt in a 640 cc./min. flow of a gaseous hydrogen stream containing 
20% hydrogen in nitrogen for 4 hours. The catalysts were tested for 
catalytic activity by loading one gram of the catalyst in a glass ampoule 
and adding 5 cc. of a 7% acrylonitrile-in-water solution. The ampoule was 
sealed and heated to the temperature specified for one hour. After the 
reaction, the ampoule was cooled and the contents were analyzed by vapor 
phase chromatography. The results of these experiments are shown in Table 
II. No by-products were observed. The indicated conversions and yields are 
based on acrylonitrile consumed. 
TABLE II 
______________________________________ 
Hydration of acrylonitrile to 
acrylamide using copper catalysts prepared 
by reducing copper salts with hydrogen 
Reduc- 
tion, Hydration, percent 
Copper salt temp., 80.degree. C. 
130.degree. C. 
Ex. reduced .degree.C. 
Conv. Yield Conv. Yield 
______________________________________ 
7 Cu(NO.sub.3).sub.2 
175 7 0 34 1.1 
8 Cu(NO.sub.3).sub.2 
275 7 100 50 85 
9 Cu.sub.2 C.sub.2 O.sub.4 
275 40 0 36 2.7 
10 Cu(Ac).sub.2 
275 21 21 48 38 
11 CuCl.sub.2 300 38 0 38 0.3 
12 CuCl 300 41 0 45 3.6 
13 CuBr 300 18 0 17 1.4 
14 CuSO.sub.4 300 3 0 4 3 
15 CuCO.sub.3 175 74 97 No Data 
16 CuC.sub.3 O.sub.4 
175 16 90 No Data 
17 Cu--Cr car- 
175 62 95 No Data 
bonate 
______________________________________ 
Examples 18-22.--Copper catalysts prepared by the reduction of copper salts 
with NaBH.sub.4 
Various copper salts were treated with 200 cc. of a 0.5 molar solution of 
NaBH.sub.4 in water for one hour at 25.degree. C. These catalysts were 
tested as shown in Examples 7-17 above, and the results are shown in Table 
III. No by-products were detected in the product. 
TABLE III 
______________________________________ 
Hydration of acrylonitrile to acrylamide 
using copper catalysts prepared 
by reducing copper salts with NaBH.sub.4 
Hydration at 100.degree. C. 
Copper salt for 1 hr., percent 
Example reduced Conversion 
Yield 
______________________________________ 
18 Cu(NO.sub.3).sub.2 
98.9 90.5 
19 Cu(C.sub.2 H.sub.3 O.sub.2).sub.3 
100 86.6 
20 CuCrO.sub.4.sup.a 
9.9 28.6 
21 CuC.sub.2 O.sub.4 
100 91.6 
22 Copper tartrate 
51.6 80.1 
______________________________________ 
.sup.a 0.25 g. of catalyst employed rather than 1 g. 
Example 23.--Copper catalyst prepared by the reduction of CuCl.sub.2 with 
Zn 
To prepare a Urushibara-A copper catalyst, zinc was added to an aqueous 
solution of cupric chloride to precipitate metallic copper. After the 
evolution of gas had ceased, the product was leached with acetic acid to 
form the desired catalyst. Using the same procedure as shown in Example 7, 
0.51 g. of the catalyst was used to hydrate acrylonitrile to acrylamide at 
75.degree. C. for one hour. The conversion of the nitrile was 16% with a 
55.2% yield of the amide. No by-products were observed. 
Example 24.--Copper catalyst prepared by the reduction of copper nitrate 
with hydrazine 
Copper nitrate was reduced to copper metal contacting 0.1 mole of 
Cu(NO.sub.3).sub.2 in 100 cc. of water with 200 cc. of 0.1 molar aqueous 
hydrazine over a one hour period at 25.degree. C. One gram of copper 
catalyst prepared was reacted with 5 cc. of a 7% aqueous acrylonitrile 
solution at 100.degree. C. for one hour. The acrylonitrile was 11.2% 
converted to give a 9.8% yield of acrylamide. 
Example 25.--Copper prepared by reducing copper oxide on a copper support 
A catalyst was prepared by heating 8.2 g. of 100 mesh copper screen in air 
at 300.degree. C. for 10 hours and then reducing the screen with hydrogen 
as described above at a temperature of 175.degree. C. To a bomb reactor 
was added 5.99 g. of the reduced screen, 5.1 g. of water and 0.374 g. of 
acrylonitrile. The reactor was sealed and heated at 100.degree. C. for 65 
minutes. After the reaction, the contents were analyzed to find that 6.3% 
of the acrylonitrile had been converted and of the acrylonitrile converted 
97.8% was acrylamide. No by-products were found. 
Example 26.--Conversion of massive copper metal to an active metal catalyst 
In a manner similar to Example 25, a porous cylindrical copper plug 
measuring 5/8" in diameter.times.4" and sold by the Hyuck Corporation was 
used as a catalyst for the conversion of acrylonitrile to acrylamide. The 
reaction was conducted in a continuous manner by passing a 7% solution of 
acrylonitrile in water over the catalyst at a rate of 14 cc./hr. and at a 
temperature of 80.degree. C. Without oxidation and reduction, the 
acrylonitrile was 7% converted and no acrylamide was detected in the 
product. Upon oxidation of the copper plug at 300.degree. C. and reduction 
with hydrogen at 175.degree. C., the acrylonitrile was about 20% converted 
and the yield of acrylamide was 50%. 
Example 27.--Use of fine copper powder as a catalyst 
The catalyst was a -325 mesh copper metal sold by Baker and Adamson 
Chemicals Co. under the Code 1618 and having a surface area of 0.5 square 
meter per gram. One gram of the copper metal catalyst was placed in a 
reactor with 5 cc. of a 7% solution of acrylonitrile in water. The reactor 
was heated at 120.degree. C. for 1 hour to convert 12.2% of the 
acrylonitrile. The yield of acrylamide was 13.3%, and no 
.beta.-hydroxypropionitrile was found in the product. The same copper 
powder reduced with hydrogen gave a 13.1% conversion of acrylonitrile and 
a 28.4% yield of acrylamide with no .beta.-hydroxypropionitrile. 
Example 28.--Preparation of acrylamide from commercially available Raney 
copper 
Activated Raney copper sold by the W. R. Grace Company as Grade 29 and 
having a surface area of 14.3 square meters per gram was employed as the 
catalyst in the hydration of acrylonitrile to acrylamide. To a reactor was 
charged 0.25 g. (dry weight) of the wet activated Raney copper catalyst 
and 5 cc. of 7% acrylonitrile in water. The temperature of the reactor was 
maintained at 80.degree. C. for one hour. Analysis of the reactor contents 
after reaction indicated that 33.7% of the acrylonitrile had been 
converted and that a 39.4% yield of acrylamide was produced. No 
.beta.-hydroxypropionitrile was observed in the product. 
Example 29.--Use of commercial Raney copper as a catalyst 
In the same manner as described in Example 28, 0.14 g. dry weight of Grace 
Grade 29 Raney copper was employed to convert acrylonitrile to acrylamide. 
The conversion of acrylonitrile was 31.9%, and the yield of acrylamide was 
39.5%. No .beta.-hydroxypropionitrile was found in the product. 
In the same manner as described above, other copper salts are reduced to 
obtain desirable copper catalyst. For example, a solution of cupric 
nitrate is reduced with metallic zinc to give a desirable copper catalyst 
that is employed in the conversion of acrylonitrile to acrylamide, 
methacrylonitrile to methacrylamide or pentanonitrile to pentanoamide.