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United States Patent (19) 11 4,032,578 Savini (45) June 28, 1977

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United States Patent (19) 11 4,032,578 Savini (45) June 28, 1977 United States Patent (19) 11 4,032,578 Savini (45) June 28, 1977 54 PROCESS FOR THE MANUFACTURE OF 3,432,557 3/1969 Wile .............................. 260/601 R ALDEHYDES AND HDA AND OTHER FOREIGN PATENTS OR APPLICATIONS ALCOHOLS BY ALDOL CONDENSATON 2,058,532 5/1971 France ........................... 260/638 B 75 Inventor: Charles G. Savini, Warren, N.J. Primary Examiner-Joseph E. Evans 73) Assignee: Exxon Research and Engineering Company, Linden, N.J. Attorney, Agent, or Firm-C. Leon Kim 57 ABSTRACT Filed: Jan. 7, 1976 (22) A new process for the manufacture of aldehydes by (21) Appl. No.: 647,150 aldol condensation using a feed consisting of crude, high conversion, demetalled conventional oxo product Related U.S. Application Data is described. In another embodiment a new process for (63) Continuation-in-part of Ser. No. 547,475, Feb. 6, the manufacture of hexadecyl alcohol and related alco 1975, abandoned, which is a continuation of Ser. No. hols using the above-described feed is also set forth. 317,615, Dec. 22, 1972, abandoned. The process is a uniphase aldol condensation process utilizing small quantities of basic catalyst and operating (52) U.S. C. ........................ 260/601 R; 260/638 B above certain minimum threshold temperatures. The (51) Int. C.’.................. C07C47/02; C07C 45/00; process is operable with crude oxo feeds that contain as CO7C 29/14 much as 40% by weight acetals. Process conditions are (58) Field of Search .................... 260/601 R, 638 B described which enable reversion of the acetals to alde (56) References Cited hydes and alcohols thereby allowing concurrent con densation of reactive components with high selectivi UNITED STATES PATENTS ties to the product alcohols and aldehydes. The prod 2,485,989 10/1949 Smith ............................. 260/601 R ucts of the process, such as hexadecyl alcohol, are well 2,757,200 7/1956 Jones et al. ................. 260/638 HF 2,809,220 10/1959 Mertzweiller et al. ...... 260/638 HF known and have many uses, such as in the formulation 2,810,762 10/1957 Ernst et al..................... 260/635 A of cosmetic products. 2,848,498 8/1958 Mention .............. ... 260/638 B 3,148,218 9/1964 Heimsch et al. ............... 260/601 R 8 Claims, 1 Drawing Figure SOLUBLITY OF WATERN Cs OXO PRODUCT O 90% - Conversion Oxo Product 75%-Conversion Oxo Product O50%-Conversion Oxo Product O25% -Conversion Oxo Product OO 2OO 3OO 400 SOO 6OO 700 TeMPERATURE (F) U.S. Patent June 28, 1977 4,032,578 SOLUBLITY OF WATER IN Cs OXO PRODUCT 4O 3O O 90% - Conversion Oxo Product 75%-Conversion Oxo Product O 50%-Conversion Oxo Product O 25% - Conversion Oxo Product O O O2 OO 2OO 3OO 4OO 5OO 6OO 7OO TEMPERATURE (F) 4,032,578 2 Also, U.S. Pat. No. 2,820,067 describes a process for PROCESS FOR THE MANUFACTURE OF the preparation of high molecular weight alcohols from ALDEHYDES AND HDA AND OTHER ALCOHOLS low molecular weight olefins by a novel modification of BY ALDOL CONDENSATION the aldehyde synthesis reaction. This modification re sides in the treatment at elevated temperatures and low CROSS-REFERENCE TO RELATED pressures of the aldehyde products from the carbonyla APPLICATIONS tion process in the presence of zinc salts for extended This application is a continuation-in-part of pending periods which is then followed by hydrogenation to U.S. Ser. No. 574,475, filed Feb. 6, 1975, now aban produce high yields of dimeric primary alcohols. U.S. doned, which is in turn a continuation of U.S. Ser. No. 10 Pat. No. 3,248,428 discloses a process for producing 317,615 filed Dec. 22, 1972, now abandoned. alpha, betaunsaturated carbonyl compounds of in creased molecular weight by the condensation of car FIELD OF THE INVENTION bonyl compounds of relatively low molecular weight at This invention relates to a novel process for the man elevated temperatures with a catalyst comprising an ufacture of hexadecyl alcohol via aldol condensation 5 insoluble reaction product of molybdenum oxide and using crude, high conversion, demetalled, conventional magnesium oxide. Finally, U.S. Pat. No. 2,848,498 oxo product as feed followed by hydrogenation and describes a process for the production of aldols, ketols purification. More particularly, the invention relates to and unsaturated oxo compounds from one or more an improved aldol condensation process which repre saturated oxo compounds as feeds. The process com sents a viable alternative to presently employed aldox 20 prises mixing a stream of a saturated oxo compound or processes. compounds with a stream of an aqueous alkaline con densation agent. For the most part, the abovedescribed BACKGROUND OF THE INVENTION processes result in selectivities considerably less than The manufacture of hexadecyl alcohol and related 100% and during operation require significant controls alcohols is presently commercially produced via the 25 to avoid undesirable side reactions and may require aldox process whereby overall produce yields are ap catalyst recycle and the use of special materials which proximately 20%. Additionally, the commercially em resist corrosion of the high caustic concentrations. ployed process produces severe operating problems There is, therefore, a need for an efficient, highly selec and significantly reduces the production of the conven tive route to aldehydes and their corresponding hydro tional oxo alcohol. Alternate conventional systems 30 genated aldol saturated alcohols which avoids many of employ low temperature two-phase and additionally the processing problems of conventional systems. may be characterized as high basicity systems. Selec tivities for the conventional systems have never appre SUMMARY OF THE INVENTION ciably exceeded about 60% due to the side reactions In accordance with the present invention, a twostep which occur at process conditions required to achieve 35 process for the manufacture of aliphatic alcohols is acceptable reaction rates. described. The process comprises contacting an alde hyde or acetal-containing feedstream with a lower level DESCRIPTION OF THE PRIOR ART of basic catalyst selected from the group consisting of Aldolization processes are well known in the art and Groups I-A and II-A hydroxides, soaps, alkoxides, provide a ready means for preparing aldehydes and 40 phenoxides; quaternary ammonium hydroxides, cho alcohols from compounds containing olefinic unsatura line and the like. The contacting is carried out in the tion. These processes generally involve condensation of presence of a controlled amount of water and a temper two moles of aldehyde to produce a hydroxy aldehyde. ature in excess of 200 F. to thereby provide a uniphase The lower aldols are readily dehydrated to the corre reaction media whereby aldolization of the aldehyde sponding unsaturated aldehyde which upon reduction 45 feedstream takes place. The amount of water present in forms the saturated alcohol. One of such processes is the aldolization media must be controlled such that it described adequately in U.S. Pat. No. 3,454,649 where does not exceed the water solubility of said media so as high molecular weight alcohols containing 2 or more to maintain a homogeneous liquid-phase aldolization carbon atoms than twice the number in the olefin feed mixture. The product from this step is then hydroge are produced. The feed employed is the oxo reaction 50 nated over Raney-nickel catalyst at temperatures of product which is mixed with an oil soluble Group II 300' to 400' F. and hydrogen partial pressures of 1-40 metal compound such as magnesium oleate. The com atm. to produce a yield of saturated alcohols. bined feed is then passed to a heating zone where di By the term "aldolization" as used above is meant the meric aldehydes are produced. After demetalization, condensation reaction in which two molecules of alde the reaction product is hydrogenated under conven 55 hyde react and bond one to the other in a way such that tional hydrogenating conditions in the presence of hy the alpha carbon of the first aldehyde molecule be drogenation catalysts to provide dimeric alcohols. In comes attached to the carbonyl carbon of the second. U.S. Pat. No. 2,810,762, a process for the preparation The following illustrative equation demonstrates this of glycols and dimeric alcohols from aldehydes is de aldol condensation and subsequent dehydration. scribed wherein the aldehyde feedstocks employed are 60 feedstocks contaminated with minor amounts of alco hols and other impurities. The decobaited and dried H H crude aldehyde products from an oxo process are CH-CRO + CH-CEO passed to a reaction vessel and mixed with a slurry of le sodamide in a temperature range of about 100-250 F 65 where aldolization occurs. The crude condensation ch-h-ch-cho A ch,-ch=ch-cHo ; ho product is then converted to mono- and dihydric alco OH hols under conventional hydrogenation conditions. 4,032,578 - 3 The extent of aldol dehydration is dependent upon the specific process conditions of the reaction system. As H H described above, the feed may broadly be referred to as any aldehyde-containing feedstream. More particu R-CRO -- 2ROH 2 r--or + HO larly, feedstreams such as pure aldehyde or dilute feed OR streams containing aldehydes with or without asso aldehyde alcohol acetal ciated impurities may be used in the present invention. The basic catalyst employed is one generally to be Preferably, the feedstream employed is a crude, deme described as a weak to moderate base or a dilute solu talled, high conversion oxo product stream from a typi O tion of a strong base. Typically, Groups I-A and I-A cal oxo reactor. Such a crude oxo feedstream typically hydroxides are employed. Equally operable are Groups contains 20% hydrocarbons, 40% aldehydes, 20% alco I-A and II-A soaps, such as sodium stearate.
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