Patent GB-519381-A (GB)
Title: Manufacture of maltosamines
IPC: C07H15/04
Filed: 1938-09-21
Abstract: 519,381. Maltosamines. DU PONT DE NEMOURS & CO., E. 1. Sept 21, 1938, No. 27577. Convention date, Sept. 21, 1937. [Classes 2 (iii) and 15 (ii)], Maltosamines are manufactured by the action of hydrogen in the presence of a hydrogenation catalyst on maltose and ammonia or a primary or secondary aliphatic, cycloaliphatic or araliphatic amine, or on a preformed reaction product of these compounds (which may be prepared in aqueous or alcoholic solution and appear to mostly compounds of the alcoholammonia type). The hydrogenation may be carried out below 50‹C., under elevated pressure, in the presence of a base metal catalyst, e.g. copper cobalt, copper chromite or, preferably, nickel, which may be employed in a finely divided state or supported on, porous or inert carriers such as alumina, pumice or kiesalguhr. Those of the products which contain an aliphatic radicle of at least six carbon atoms may be used as wetting, penetrating, detergent, dispersing, emulsifying, frothing and foaming agents, or, in some cases, as softening agents, whilst those which contain an aliphatic radicle of less than six carbon atoms, and maltosamine itself, yield surface-active agents on further alkylation. In examples : (1) maltose and methylamine are dissolved in water and shaken with hydrogen under pressure in the presence of a nickel catlayst to produce metbylmaltosamine; (2) maltose and dodecylamine are warmed with water and alcohol and the mixture is treated with hydrogen under pressure in the presence of a platinum oxide catalyst, yielding dedocylmaltosamine ; the product may be used as a detergent in soft, alkaline or hard water ; (3) maltose (or a dry malt containing maltose) is heated with hexadecylamine in methyl alcohol, and the resulting 1-hexadecylamino-1-hydroxymaltose is isolated and shaken with hydrogen under pressure in the presence of dioxane and a nickel catalyst or methyl alcohol and a platinum oxide catalyst, producing hexadecylmaltosamine ; the product is a softening agent for viscose rayon ; (4) maltose is heated with 9:10-octadecerylamine in methanol, and the resulting 1-octadecenylamino-1-hydroxymaltose is shaken in methanol with hydrogen under pressure in the presence of a platinum oxide catalyst, yielding octadecylmaltosamine, which is a softener for viscose rayon, and octadecenylmaltosamine, which is a detergent; (5) the hexadecylamine in (3) is-replaced by a mixture thereof with octadecylamine ; the product is a softening agent for viscose rayon; (6) a mixture of maltose, ammonia and water is shaken with hydrogen under pressure in the presence of a nickel catalyst to produce maltosamine. Other amines specified are: diethylamine, mono- and din- and isopropylamine, di-nbutylamine, monoisobutylamine, benzylamine, cyclohexylamine, naphthenylamine, aniline, N- methyl - N - isobutylamine, N - ethyl - N - hexylamine, n - octylamine, n decylamihe, N - isopropyl - N - octylamine, N - 2 - ethylhexylamine, N - methyl - N - 2 - ethylhexylamine, N - methyl - N - hexadecylamine, N - ethyl - N - tetradecylamine, undecenylamine, ricinoleylamine, oleostearylamine, the amines corresponding to the mixtures of alcohols obtained by catalytic ester hydrogenation or sodium reduction of natural fats and oils such as coconut oil, cotton seed oil, castor oil, China wood oil, sperm oil, lard oil or beef tallow or to the higher alcohols obtained in the catalytic synthesis of methanol from carbon monoxide and hydrogen, or substituted aliphatic amines, e.g. those containing aryl, ether, ester, hydroxy or sulpho groups. Maltos-amine may also be reacted with maltose to form dimaltosamine. Specifications 297,484 and 313,617, [both in Class 2 (iii)], are referred to. The Specification as open to inspection under Sect. 91 comprises also the following subject-matter: (a) The initial condensation products between maltose and ammonia or an amine may be prepared per se and employed as softening agents for viscose rayon yarn. In examples : (1) dodecylamine and maltose are heated in water to produce 1-didecylamino - 1 - hydroxymaltose ; (2) methylheptylamine and maltose are heated in methanol to yield 1 - (N - methyl - N - heptyl) - amino - 1 - hydroxymaltose; (b) maltosamine or alkylmaltosamines, e.g. methylmaltosamine, ethylmaltosamine, hydroxyethyhnaltosamine or dodecylmaltosamine, may be alkylated. In an example methylmaltosamine is heated with octadecyl bromide in the presence of sodium carbonate, benzene, ethyl and methyl alcohols and potassium iodide. The octadecyl bromide may be replaced by dodecyl chloride, dimethyl or diethyl sulphate, amyl chloride or octyl p-toluenesulphonate, the sodium carbonate by magnesium oxide, calcium carbonate, potassium carbonate, sodium acetate or 'potassium acetate, the solvent mixture by aqueous alcohol and the potassium iodide by sodium iodide ; (c) maltosamine may be reacted with an aldehyde, e.g. formaldehyde, acetaldehyde or lauraldehyde, followed or accompanied by reduction with hydrogen in the presence of a nickel catalyst ;(d) the maltosamines or the initial condensation products may be converted into salts, e.g. with hydrochloric, sulphuric, phosphoric, boric, acetic, formic, lauric, oleic or stearic acid ; (e) aniline may be used as the amine in the condensation with maltose. This subject-matter does not appear in the Specification as accepted.