Patent GB-981285-A (GB)
Title: Alkylated 1,3-dioxanes and their use as perfumes
IPC: C11D9/44
Filed: 1963-09-04
Abstract: The invention comprises compounds of the general formula <FORM:0981285/C2/1> wherein R1 is an alkyl group containing 4-9 carbon atoms, R2 is hydrogen or an alkyl group containing 1-4 carbon atoms, and R3 is hydrogen or a methyl radical.  The compounds are prepared by reacting about 1 to 1.5 equivalents of the appropriate 1,3-diol with about 1 equivalent of the appropriate aldehyde in the presence of, firstly, a solvent which azeotropes with water, e.g. chloroform, ethylene dichloride or benzene, and, secondly, about 0.01% to about 10% of an acid catalyst, e.g. sulphuric acid, hydrochloric acid, p-toluenesulphonic acid or an insoluble resin acid of the sulphonic acid type. The reaction product is cooled, neutralized with aqueous or dry alkali, washed and distilled. Examples are given.  Comparative examples describe other 1,3-dioxanes outside the scope of the above formula, some of which contain an additional methyl substituent in the 4- or 5-position. Specification 521,566 is referred to.ALSO:Cleaning compositions contain as a perfume a compound of the general formula <FORM:0981285/C4-C5/1> wherein R1 is an alkyl group having 4-9 carbon atoms, R2 is hydrogen or an alkyl group having 1-4 carbon atoms, and R3 is a hydrogen atom or a methyl group.  The compositions may also contain soaps or non-soap detergents such as sodium lauryl sulphate, sodium alkyldiphenyloxide or the sulphonate thereof, or <FORM:0981285/C4-C5/2> wherein b is selected to provide a molecular weight of propylene oxide of 1750 and a+c is an integer to provide 10% or 20% ethylene oxide in the molecule, soil suspending agents such as sodium carboxymethyl cellulose, sodium carboxymethyl hydroxyethyl cellulose, sodium cellulose sulphate, polyvinyl alcohol or polyethylene glycols, chlorine-releasing agents such as trichloro-cyanuric acid or its sodium or potassium salts, dichlorodimethylhydantoin, N - chlorosuccinimide, trichloromelamine, calcium hypochlorite, chlorinated trisodium phosphate, chloramine-T or N,N-dichlorooxo-carbonamidine, abrasives such as silica, volcanic ash, diatomaceous earth, pumice, alumina, feldspar or carborundum, and other additives such as sodium polyphosphates, sodium metasilicate, sodium silicate solids or solutions, or sodium carbonate, tetraborate, sesquicarbonate or sulphate.  Examples describe (5) a dishwasher composition containing 2 - isobutyl - 4,5,6 - trimethyl - 1,3 - dioxane, sodium tripolyphosphate, chlorinated trisodium phosphate, sodium silicate solutions, compounds of the formula <FORM:0981285/C4-C5/3> as defined above, colorants and water, (6) a liquid detergent containing 2-(2-ethyl-propyl)-4-methyl - 1,3 - dioxane, potassium dodecyl-benzenesulphonate, sodium xylene-sulphonate, lauric/myristic diethanol amide, lauric/myristic isopropanol amide, potassium pyrophosphate, sodium silicate, sodium carboxymethylcellulose, methylcellulose and water, (7) a scouring cleanser containing 2-isobutyl-2,4-dimethyl-1,3-dioxane, 90 mesh silica, chlorinated tri-sodium phosphate, sodium alkylbenzene sulphonate and sodium tripolyphosphate, and (8) dishwasher compositions as in (6) having an added perfumery blend containing citronellol, cinnamic alcohol, thyme oil, amyl cinnamic aldehyde, and (a) 2-isobutyl-4-methyl-1,3-dioxane or (b) linalool and geranyl acetate.  Specification 521,566 is referred to.ALSO:A perfumery blend having a geranium odour comprises citronellol, 2-isobutyl-4-methyl-1,3-dioxane, cinnamic alcohol, thyme oil and amyl cinnamic aldehyde.  Specification 521,566 is referred to.ALSO:Dry bleaches contain as perfume a compound of the general formula <FORM:0981285/D1-D2/1> wherein R1 is an alkyl group containing 4-9 carbon atoms, R2 is hydrogen or an alkyl group containing 1-4 carbon atoms, and R3 is hydrogen or a methyl radical.  The bleaching composition may contain only the perfume and a chlorine-releasing agent but other ingredients may also be present.  Specified chlorine-releasing agents are trichlorocyanuric and or its sodium or potassium salts, dichlorodimethylhydantoin, N-chlorosuccinimide, trichloromelamine, calcium hypochlorite, chlorinated trisodium phosphate, chloramine-T and N, N-dichloro-azocarbonamidine.  Other specified additives are soaps, non-soap detergents such as sodium lauryl sulphate, sodium alkyldiphenyloxide sulphonate or HO(C2H4O)a (C3H6O)b (C2H4O)c H wherein b is selected to provide a molecular weight of propylene oxide of 1750 and a + c is an integer to provide 10% or 20% ethylene oxide in the molecule, and sodium phosphate, carbonate, tetraborate, sulphate, sesquicarbonate or silicates. Example 4 describes dry bleaches containing sodium tripolyphosphate, sodium silicate, sodium sulphate and (a) 2-isobutyl-4-methyl-1, 3-dioscane, potassium dichlortriazinetrione and sodium fatty alcohol sulphate, (b) 2-n-heptyl-4-methyl-1, 3-dioxane, potassium dichlortriazinetrione and sodium alkylbenzenesulphonate, or (c) 2-isobutyl-4, 6-dimethyl1, 3-dioxane, dichlorodimethylhydantoin and sodium fatty alcohol sulphate.  Specification 521,566 is referred to.