Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing
Reexamination Certificate
2000-09-22
2002-08-20
Keys, Rosalynd (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Oxygen containing
Reexamination Certificate
active
06437196
ABSTRACT:
This application is a 371 of PCT/JP00/00345 filed Jan. 25, 2000.
TECHNICAL FIELD
The present invention relates to a process for producing a glyceryl ether having a low organohalogen compound content.
BACKGROUND ART
Glyceryl ethers are generally produced by a process comprising three steps, that is, a first step for reacting an alcohol with an &agr;-epihalohydrin in the presence of an acid catalyst such as sulfuric acid, tin tetrachloride or boron trifluoride-ether complex, thereby obtaining a halohydrin ether; a second step for subjecting the halohydrin ether to intramolecular ring closure by using an alkali, thereby obtaining the corresponding glycidyl ether, and a third step for subjecting the glycidyl ether to hydrolysis or the like treatment. In the first step for addition reaction of the epihalohydrin, however, a 2-mole adduct of the epihalohydrin and an isomer of the halohydrin ether different in alcohol added position are inevitably produced. Since these 2-mole adduct, isomer and the like which are organohalogen compounds cannot be decomposed by the intramolecular ring closure of the second step and even in the third step for converting the glycidyl ether to the corresponding glyceryl ether by a known method (Japanese Patent Application Laid-Open No. SHO 49-86307, SHO 56-133281, HEI 5-32578, or the like), they are hard to be hydrolyzed, the glyceryl ether thus obtained necessarily contains organohalogen compounds.
Such glyceryl ether having a high organohalogen compound content is not suited for use in cosmetics, body detergents and the like which are brought into direct contact with a body upon application.
As means for removing or decomposing such organohalogen compounds, purification or decomposition by a strong alkali can be considered. However, the above-described halohydrin ether different in alcohol added position has physical properties, such as boiling point, close to those of the target glyceryl ether, which makes it difficult to remove it by ordinary purification such as distillation. It is possible to decompose it by adding thereto a strong alkali such as NaOH or KOH, followed by heating, but this means is not preferred, because it causes severe coloration and also a partial decomposition of the target glyceryl ether.
In Japanese Patent Application Laid-Open No. HEI 6-25052, disclosed is a process for reducing an organochlorine content by synthesizing a glyceryl ester and then subjecting it to alkali hydrolysis in the presence of an alcohol. This process which requires a fatty acid in an amount not less than an equivalent mole, however, is by no means economical.
DISCLOSURE OF THE INVENTION
It is an object of the present invention to provide an economical process for producing a glyceryl ether.
It is another object of the invention to provide a process for producing a glyceryl ether which has a markedly low organohalogen compound content.
The present inventors have discovered that the organohalogen compound formed upon preparation of a glycidyl ether can be decomposed by heating the glycidyl ether or a glyceryl ether to a predetermined temperature in the presence of a salt formed from a strongly basic compound and a weakly acidic compound.
The present invention therefore provides a process for producing a glyceryl ether comprising reacting an alcohol with an &agr;-epihalohydrin in the presence of an acid catalyst, subjecting the reaction mixture to ring closure, thereby converting it to the corresponding glycidyl ether and then hydrolyzing the resulting glycidyl ether into the corresponding glyceryl ether, wherein (a) the glycidyl ether is hydrolyzed at 140 to 230° C. in the presence of a salt formed from a strongly basic compound and a weakly acidic compound or (b) the reaction mixture after hydrolysis is heated at 100 to 230° C. in the presence of a salt formed from a strongly basic. compound and a weakly acidic compound.
The present invention also provides a process for producing a glyceryl ether, comprising:
hydrolyzing a glycidyl ether at 140 to 230° C. in the presence of a salt formed from a strongly basic compound and a weakly acidic compound.
The present invention also provides a process for producing a glyceryl ether, comprising:
hydrolyzing a glycidyl ether, followed by
heating the reaction mixture at 100 to 230° C. in the presence of a salt formed from a strongly basic compound and a weakly acidic compound.
The present invention also provides a method of reducing the content of organohalogen compound(s) of a glyceryl ether, comprising:
hydrolyzing a glycidyl ether at 140 to 230° C. in the presence of a salt formed from a strongly basic compound and a weakly acidic compound.
The present invention also provides a method of reducing the content of organohalogen compound(s) of a glyceryl ether, comprising:
heating a glyceryl ether containing organohalogen compound(s) at 100 to 230° C. in the presence of water and a salt formed from a strongly basic compound and a weakly acidic compound.
BEST MODES FOR CARRYING OUT OF THE INVENTION
A more complete appreciation of the invention and many of the attendant advantages thereof will be readily obtained as the same becomes better understood by reference to the following detailed description.
First, in the present invention, an alcohol and an &agr;-epihalohydrin are reacted in the presence of an acid catalyst, thereby producing a halohydrin ether.
Examples of the alcohol which may be used in the present invention include those represented by the following formula (1):
R—(OA)
p
—OH (1)
where
R represents a saturated or unsaturated, linear or branched C
1-36
hydrocarbon group,
A represents a C
2-4
alkylene group, and
p is 0 to 100.
The alcohols where R has 4 to 22 carbon atoms, particularly 4 to 18 carbon atoms, are preferred. Specific examples include saturated aliphatic alcohols such as butanol, pentanol, hexanol, heptanol, octanol, nonanol, decanol, undecanol, dodecanol, tridecanol, tetradecanol, pentadecanol, hexadecanol, heptadecanol, octadecanol, 2-ethylhexanol and 3,5,5-trimethylhexanol, and unsaturated aliphatic alcohols such as oleyl alcohol and linoleyl alcohol, and alkylene oxide adducts thereof. In the formula (1), A preferably represents ethylene, while p preferably stands for 0 to 20, with 0 being particularly preferred.
Examples of the &agr;-epihalohydrin usable in the present invention include &agr;-epichlorohydrin, &agr;-epibromohydrin and &agr;-epiiodohydrin, of which the &agr;-epichlorohydrin is particularly preferred from the viewpoint of easy availability.
As the acid catalyst, usable in the present invention are, as well as Brønsted acids such as hydrochloric acid and sulfuric acid, metal compounds containing at least one element such as boron, aluminum, silicon, titanium, iron, cobalt, zinc, zirconium, tin, antimony or the like which are so-called Lewis acids. Specific examples of the Lewis acid include boron trifluoride-ether complex, boron trifluoride-acetic acid complex, boron trifluoride-phenol complex , aluminum chloride, aluminum bromide, zinc chloride, tin tetrachloride, antimony chloride, titanium tetrachloride, silicon tetrachloride, ferric chloride, ferric bromide, cobalt (II) chloride, cobalt (II) bromide, zirconium chloride, boron oxide and acidic active alumina.
When such a Lewis acid is employed, the reaction can be effected without or after removal of water from the system in a conventional manner, but the latter one is preferred because it brings about an increase in both the reaction rate and yield.
The catalyst is used in an amount of 0.001 to 0.1 mole per mole of the alcohol, with 0.005 to 0.05 mole being particularly preferred.
The formation of a halohydrin ether from an alcohol and an &agr;-epihalohydrin may be conducted in an ordinary manner, described specifically, by reacting, with the alcohol, the &agr;-epihalohydrin which is used in an amount of 0.5 to 1.5 moles, preferably 0.6 to 1.2 moles per mole of the alcohol, in the presence of the above-exemplified acid catalyst at a temperature of 10 to 150° C., preferably 70 to 120° C. for 0.5 to 10 hours.
Fr
Miyajima Tetsuya
Uno Mitsuru
Kao Corporation
Keys Rosalynd
Oblon, Spivak, McCleland, Maier & Neustadt, P.C.
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