Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing
Patent
1995-05-01
1997-04-08
Cook, Rebecca
Organic compounds -- part of the class 532-570 series
Organic compounds
Oxygen containing
C07C 2700
Patent
active
056189850
DESCRIPTION:
BRIEF SUMMARY
This is a continuation of PCT/FI 94/00273.
The object of the invention is a new, technically simple but efficient process for the preparation of 2-n-butyl-2-ethyl-1,3-propane diol from 2-ethyl hexanal and formaldehyde. The invention is based on correctly selected sources of the initial components and on the use of correctly selected catalysts.
2-n-butyl-2-ethyl-1,3-propane diol is a compound known per se, which is used, for example, in the preparation of polyesters and in the paint industry as one component of pulverous paints. The advantages of the compound include its very good UV shield and its very low adsorption of water.
The preparation of 2-n-butyl-2-ethyl-1,3-propane diol from 2-ethyl hexanal and formaldehyde by aldol addition, and so-called Cannizzaro reaction immediately following it, is per se known in organic chemistry. The said reactions are achieved by using in the reaction a basic alkali metal hydroxide or earth alkali metal hydroxide catalyst.
Japanese patent publication JP-48 043 085 describes a process for preparing 2-n-butyl-2-ethyl-1,3-propane diol from 2-ethyl hexanal and formaldehyde in the presence of a basic alkali metal hydroxide, in two steps, in the first of which a selective aldol condensation was allowed to occur at 30.degree.-60 .degree. C., the pH being 8-11. In the second step, a selective cross-Cannizzaro reaction was performed at 65.degree.-90.degree. C. at pH 8-11. However, the methods for the isolation and purification of the 2-n-butyl-2-ethyl-1,3-propane diol obtained as the final product are not reported, nor is the yield of final product.
JP patent publication 62 129 233 discloses a process for the preparation and purification of 2-n-butyl-2-ethyl-1,3-propane diol. In this process, the reaction mixture which is obtained as a result of a reaction of 2-ethyl hexanal and formaldehyde in the presence of an alkali metal hydroxide or an earth alkali metal hydroxide and water and which contains 2-n-butyl-2-ethyl-1,3-propane diol is neutralized with an organic acid or a mineral acid, the organic phase is separated, and one part of the organic phase is washed, once or several times, with 0.01-2 parts of water in order to remove the formaldehyde. Finally the organic phase is vacuum distilled. For this process, a final product yield of 91.9% is reported when the initial material used was paraformaldehyde.
In JP patent publication 2 062 836, the yield and grade of 2-n-butyl-2-ethyl-1,3-propane diol has been improved by adding to a mixture of 2-ethyl hexanal and formaldehyde in the presence of an alkali metal hydroxide in a heterogenous system 2% by weight or more (in proportion to the 2-ethyl hexanal) of C.sub.14 alcohol. The phases are separated from a mixture neutralized with an organic acid or a mineral acid, and the pH of the organic phase is adjusted to 4.5-5.5 by means of phosphoric acid, before its vacuum distillation. In the example given, the reaction mixture contained 7.9% weight of methanol (in proportion to the 2-ethyl hexanal), the 2-n-butyl-2-ethyl-1,3-propane diol yield reported in this case being 94.4%.
In U.S. Pat. No. 2,413,803, 2-n-butyl-2-ethyl-1,3-propane diol is prepared from 2-ethyl hexanal and formaldehyde by means of potassium hydroxide from a homogenous mixture (homogenized with ethanol) in a multiple-step and long synthesis process, with a yield of 73%.
In U.S. Pat. No. 5,146,004, 2-ethyl-2-(hydroxymethyl) hexanal is prepared from 2-ethyl hexanal, formaldehyde and a tertiary amine. Any unreacted 2-ethyl hexanal can be isolated by azeotropic distillation of the organic phase of the raw product, and 2-butyl-2-ethyl-1,3 propane diol is obtained from the purified organic phase of the raw product by catalytic hydrogenation, with a yield of 85-88%. The hydrogenation is carried out by using a nickel catalyst.
In all of the processes according to the publications referred to above and in general in prior-art processes for the preparation of 2-n-butyl-2-ethyl-1,3-propane diol, multiple-step and even cumbersome reaction series are used. The yields reported are lo
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Ankner Kjell
Kulmala Kari
Rintala Lea
Cook Rebecca
Neste Oy
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