HORACE M. WEIR – "OXO PROCESS"

H. M. Weir. The OXO process has been the subject of a TAC report and I have very little that I can add to that report today. However, I will abstract it rather briefly, in order to bring this process before this meeting. The process was used for the manufacture of alcohols from olefins. The reactions are carried out both chemically and physically in a two-stage operation. In the first stage, water gas or any gas containing CO and H is approximately equal proportion is used to form the aldehyde from the double bonded compound. The typical CHO group "hooks on" at one side of the bond and hydrogen "hooks on" at the other. After the aldehyde is formed the compound is subjected to hydrogenation to yield an alcohol. Both of these sates, the formation of the aldehyde and the alcohol, can be carried out at pressures ranging all the way from about 20 atmospheres to as high as desired. Apparently the Germans used pressure as high as 250 atmosphere. It is not plain from the documents which we have, not so far as I was able to learn from any interviews, what the effect of pressure actually is other than the usual possibility of using smaller equipment with higher pressures, etc. This applied to both stages and both stages were run at various pressures. In the first stage, where the water gas was contacted with the olefin in the presence of pulverized Fischer-Tropsch catalyst, the typical conditions were about 140^oC temperature, and, let us say, 150 atmospheres pressure. In the second stage the pressure was typically only slightly less, and the temperature was generally stepped up to 180^oC. Both the reaction steps are exothermic, and circulating water, or the formation of steam with regulation of the temperature by adjusting the pressure of same, was used to take away the exothermic heat of the two stages. The conversion is rather cleancut when it comes to the formation of alcohols and the yields are quite high from most of the olefins, which have been subjected to trial. There is quite a series of record. Ninety to as high as 95 percent yield is typical from alcohol formations, but the yields of aldehyde, using one stage only, are surprisingly low. This comes about from the fact that after the aldehyde is formed, polymerization occurs very readily. Consequently if the attempt is made to make any specific aldehyde, a relatively low yield only is obtained. If, however, a reduction to the corresponding alcohol is carried out in the hydrogenation stage, a good yield of alcohol is obtained because depolymerization occurs.

The Germans built the process in large scale on the batch operation principal at Ruhrchemie. The plant there had a nominal capacity of 8,000 to 10,000 tons per annum of finished alcohols. It did not run at that rate very long, however. It was subject to bombing, and maintenance, etc., was subject to a higher priority interference by many other processes. Consequently the OXO equipment more or less limped along. At the Leuna plant of the I.G., continuous processing equipment for the OXO reactions was in operation. It was generally agreed between Ruhrchemie and I.G. Farben, who developed the continuous procedure, that the continuous method was the proper one rather than the batch method which Ruhrchemie had, but chemically both methods seemed to be satisfactory. The Germans main interest in utilizating the process was in the production of washing agents obtained by sulfating the alcohols in the range of from C-12 to C-18. As raw materials cuts from FT operations, obtained directly or through cracking cuts to get from C-11 to C-17 olefins, were selected and subjected to the OXO process to make a C-12 to C-18 alcohol. On the microfilm quite a bit of information is given on the characteristics of these working powders but about all we can say, since the intrinsic quality of the standards of comparison are unknown, is that the OXO products seem to be very good washing powders.

Aside from making these washing agents from the higher alcohols, they made a small amount of plasticizer using olefins in the range from C-17 to C-11, to make the corresponding alcohol and then converting these to the phthalic esters. The esters seem to be useful in plasticizing rubber, and in some other plastic compounds which the Germans had. There are a great many aspects of the process which are uncertain but I think we do know enough so that a competent designer could built an "OXO process" and expect it to operate at the present time.

Among the points which are obscure, is the fact that we don’t know why a FT catalyst was used. It seems from the laboratory work which was done that finely divided cobalt would probably do the same thing. One of the points of the process which I should mention is that the Aldehyde from the first stage dissolves the cobalt carbonyl formed so that of the 3 to 4 percent by weight of FT catalyst, mixed with the charge, about 1/3 of it dissolved in the aldehyde from the first stage. The cobalt carbonyl precipitates again in the H₂ reduction state and regenerates the catalyst. Just why the Germans bothered to use FT catalyst is not plain, since the cobalt carbonyl seems to be the effective agent.

W. C. Schroeder. Dr. Weir, do you want to go on with your story before we interrupt you?

H. M. Weir. I think I have covered the main points.

V. Haensel. Mr. Chairman, I want to raise the question in connection with the cobalt carbonyl.

E. B. Peck. On that catalyst, Reppe has done a great deal of work which he called carbonylation. He developed what he called soluble catalyst with nickel chloride and a trace of iodide to activate it and carbon monoxide, which he called the liquid catalyst. It had numerous advantages but had one outstanding disadvantage. It had about the same disadvantage as the F catalyst had on the whole, that is, a very slow reaction.

H. M. Weir. In trying to shorten my remarks, I didn’t take up that matter. There is quite a bit in the report and in the microfilms which bears upon two or three of the remarks that have been made.

There was a considerable amount of isomerization with the process. Isomerization was definitely proved to be due to the cobalt carbonyl in the light of results with one series of hydrocarbons. Cobalt carbonyl caused isomerization, nickel carboneal did not. Practical interest was not influenced adversely by the isomerization of the double bond which occurred, because the Germans found that washing alcohols, made from the mixture of isomerized products was a better washing agent than a pure chain alcohol sulphate. There is a table in the report that I referred to, showing the degree of isomerization and the percentage of each isomer present under stated conditions for the reaction.

W. C. Schroeder. There has been a great deal of discussion about the photographs taken by the various members of the Mission. I suppose everyone here would like to have some sort of a complete album of photographs. I don’t know exactly how that could be worked out. Perhaps if you all want to submit photographs or films to Mr. Newman, we could arrange to have extensive printing done, etc. Dr. Weir, you have been promoting this idea, what are your suggestions?

H. M. Weir. No, I haven’t been promoting the idea, though I am in favor of it. It came to my attention when Mr. Newman asked sometime ago if I would turn some films over to him for reproduction for an album here in the Bureau. It seemed tome a very good suggestion, because after all these photographs are some (not my photographs particularly, but other photographs) which I think should definitely have a place among the archives of what we have done. That was the way it came to my attention and I have my films here; I believe that Mr. Paul Jones also has his films here, so that those could be turned over, if you wish.

W. C. Schroeder. Supposing we do this, and ask the various members of the Mission who have photographs to pick out what they consider the most interesting photographs, label them, and send the labeled film to us, and we will try to reproduce enough copies of is so that we can distribute a full (tear in original document) everybody in the Mission. Do not send all of your photographs, because we would be swamped, but I would like it if you would send what you (tear in original document) your best proofs. Would that be satisfactory?

____________. Does that include technical, as well as non-technical films (tear in document)

W. C. Schroeder. Yes, I think it should. Well, then, Mr. Newman, supposing (tear in document) in their films and we have one or two copies made of each, and then (tear in document) make up an album and distribute them.

L. Newman. Yes, I’m very much in favor of doing that. I think we should have them on file here. Reproductions of whatever is of interest to anyone (tear in document) may then be made.

W. C. Schroeder. We will try to do that.

Note: At this time there was a general off-the-record discussion on the best means of disseminating the information and keeping the members of the Mission informed of the progress.

W. C. Schroeder. Well I think the meeting is winding up rather rapidly, and there are still a lot of problems to be solved until we get the final reports on this. However, I want to leave this one thought in your minds, that there is a functioning organization, and these reports are coming out steadily; I suspect coming out more rapidly than you can read them. I think we can bolster that up, and if so we will.

THE MEETING WAS ADJOURNED.