Acetaldehyde ammonia

Required Ethyl acetoacetate, 32 g. (32 ml.) acetaldehyde-ammonia, lO g. Note. The aldehyde-ammonia should preferably be fresh material the quantity should be increased to 15 g. if an old sample, which has formed brown sticky lumps, is employed.)... 

Reactions with Ammonia and Amines. Acetaldehyde readily adds ammonia to form acetaldehyde—ammonia. Diethyl amine [109-87-7] is obtained when acetaldehyde is added to a saturated aqueous or alcohoHc solution of ammonia and the mixture is heated to 50—75°C in the presence of a nickel catalyst and hydrogen at 1.2 MPa (12 atm). Pyridine [110-86-1] and pyridine derivatives are made from paraldehyde and aqueous ammonia in the presence of a catalyst at elevated temperatures (62) acetaldehyde may also be used but the yields of pyridine are generally lower than when paraldehyde is the starting material. The vapor-phase reaction of formaldehyde, acetaldehyde, and ammonia at 360°C over oxide catalyst was studied a 49% yield of pyridine and picolines was obtained using an activated siHca—alumina catalyst (63). Brown polymers result when acetaldehyde reacts with ammonia or amines at a pH of 6—7 and temperature of 3—25°C (64). Primary amines and acetaldehyde condense to give Schiff bases CH2CH=NR. The Schiff base reverts to the starting materials in the presence of acids. 

Acetaldehyde can be isolated and identified by the characteristic melting points of the crystalline compounds formed with hydrazines, semicarbazides, etc these derivatives of aldehydes can be separated by paper and column chromatography (104,113). Acetaldehyde has been separated quantitatively from other carbonyl compounds on an ion-exchange resin in the bisulfite form the aldehyde is then eluted from the column with a solution of sodium chloride (114). In larger quantities, acetaldehyde may be isolated by passing the vapor into ether, then saturating with dry ammonia acetaldehyde—ammonia crystallizes from the solution. Reactions with bisulfite, hydrazines, oximes, semicarb azides, and 5,5-dimethyl-1,3-cyclohexanedione [126-81 -8] (dimedone) have also been used to isolate acetaldehyde from various solutions. 

Acetaldehyde ammonia trimer (hexahydro-2,4,6-trimethyl-l,3,5-triazine trihydrate) [76231-37-3] M 183.3, m 94-96 , 95-97 , 97 , b 110 (partly dec). Crystd from EtOH-Et20. When prepared it separates as the trihydrate which can be dried in a vacuum over CaCl2 at room temp to give the anhydrous compound with the same melting point. The dihydrate melts at 25-28° then resolidifies and melts again at 94-95°. IRRITATES THE EYES AND MUCOUS MEMBRANES. [J Org Chem 38 3288 1973.]... 

Acetaldehyde ammonia, al62 Acetaldehyde diethyl acetal, d303 Acetaldehyde dimethyl acetal, d504... 

Working first with Polanyi, Weissenberg, and Brill, and later as the leader of the Textile Chemistry Section, Mark successively published papers on the crystal structures of hexamethylenetetramine, pentaerythritol, zinc salts, tin, urea, tin salts, triphenylmethane, bismuth, graphite, sulfur, oxalic acid, acetaldehyde, ammonia, ethane, diborane, carbon dioxide, and some aluminum silicates. Each paper showed his and the laboratory s increasing sophistication in the technique of X-ray diffraction. Their work over the period broadened to include contributions to the theories of atomic and molecular structure and X-ray scattering theory. A number of his papers were particularly notable including his work with Polanyi on the structure of white tin ( 3, 4 ), E. Wigner on the structure of rhombic sulfur (5), and E. Pohland on the low temperature crystal structure of ammonia and carbon dioxide (6, 7). The Mark-Szilard effect, a classical component of X-ray physics, was a result of his collaboration with Leo Szilard (8). And his work with E. A. Hauser (9, 10, 11) on rubber and J. R. 

The hydrolysis of 1440 in a mixture of ethanol and 75% hydrochloric acid at reflux temperature for 24 hr gave acetaldehyde, ammonia, and 5-formyl-l,3-dimethylbarbituric acid (70AP612). 

Variations on this theme include the use of acrolein/ammonia (72GEP2224160) and acrolein/acetaldehyde/ammonia (64BRP963887,69BRP1141526). Ketones can also be utilized. For example, 2,6-dimethylpyridine is obtained in 36% yield from combination of for-malin/acetone/ammonia (71GEP2064397) (Scheme 3). This general reaction has recently been extended to include the preparation of 2,6-disubstituted (78BEP858390) and 2,3-disubstituted (78GEP2712694) pyridines from aromatic or heteroaromatic ketones/aliphatic aldehydes and ammonia. 

It is reported that the compd is formed by the reaction of acetaldehyde-ammonia ammonia (Ref 1). This reaction yielded a max of 87% gum from which the separation of not more than 3% of Hexaethylidenetetramine was possible. Nitration attempt of the product was not considered practicable. The above reaction is analogous to the hexamethylenetetramine from which RDX is prepd by... 

OaN)aCH-CH(CHs>NH2. Yel crysts, mp decompca 120°. Can be prepd from acetaldehyde-ammonia, CHsCH(OH)NMa and dinitro-methane... 

The reaction between aldehydes and ammonia leads to compounds usually called aldehyde ammonias (equation 80). The first reported compound ( acetaldehyde ammonia ) was synthesized by Liebig (1835LA(14)133). Nielsen et al. (73JOC3288) have shown that most of these compounds are hexahydro-l,3,5-triazines, which are usually isolated as the trihydrates (Table 17). When aldehydes containing a branched alkyl substituent are used, the free hexahydro-l,3,5-triazines may be formed (Table 17). The kinetics of the reaction between acetaldehyde and ammonia have been studied by H NMR spectroscopy (73JOC2931), and shown to be rather complex. It is beyond the scope of this review to discuss the reaction fully. 

Acetaldehyde ammonia, al63 Acetaldehyde diethyl acetal, d251 Acetaldehyde dimethyl acetal, d438 Acetamidoacetic acid, a46 2-Acetamidopentanedioic acid, a45... 

Strecker, A. The preparation of a new material by the reaction of acetaldehyde-ammonia imine and hydrogen cyanide. Liebigs Ann. Chem. 

To a sample of povidone (Kollidon 30 batch 822) different amounts of acetaldehyde-ammonia trimer (=Hexahydro 2.4.6-trimethyl 1.3.5 triazine, C6H15N3 3H20, CAS number 76231-37-3, available at Fluka/Sigma Aldrich) were added and determined enzymatically. The acetaldehyde in this Kollidon batch was 45 mg/kg before the addition (Table 44). 

Added acetaldehyde -ammonia trimer (calculated as acetaldehyde) [mg/kg] Theoretical content of acetaldehyde [mg/kg] Found acetaldehyde [mg/kg] Recovery rate [%]... 

Acetaldehyde ammonia trimer (hexahydro-2,4,6-trimethyl-l,3,5-triazine trihydrate)... 

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