Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing
Reexamination Certificate
1999-03-16
2002-08-20
Keys, Rosalynd (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Oxygen containing
C568S670000
Reexamination Certificate
active
06437194
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to an alkylcyclohexanol alkylene oxide adduct, and a preparation process and uses of the same. More particularly, the invention relates to an alkylcyclohexanol alkylene oxide adduct which contains a trace amount or less of alkylphenol and alkylphenol alkylene oxide adduct, and a preparation process and uses of the same.
The alkylcyclohexanol alkylene oxide adduct of the invention is useful in the field of surfactants.
2. Description of the Related Art
Higher primary alcohol ethylene oxide adducts and nonylphenol alkylene oxide adduct have been conventionally known as nonionic surfactants. However, higher primary alcohol ethylene oxide adducts have a higher pour point, change to solid when the added molar numbers of ethylene oxide is increased, and become difficult to handle.
Alkylcyclohexanol alkylene oxide adducts also have excellent properties as a nonionic surfactant. Ethylene oxide adducts in particular have a lower pour point, can maintain a liquid state even in a relatively high addition mole number of ethylene oxide, can be handled with ease and thus have received attention as an excellent surfactant.
These alkylcyclohexanol alkylene oxide adducts are specifically useful for protein extraction from cell membrane in the biochemical field. When analyzing the extracted protein by ultraviolet or fluorescent spectrum, conventional alkylcyclohexanol alkylene oxide adduct contains a substanial amount of residual alkylphenol and alkylphenol alkylene oxide adduct and thus the ultraviolet or fluorescent spectrum of these compounds overlaps the spectrum of the extracted protein. As a result, it has a problem of impairing analysis accuracy, and the development of alkylcyclohexanol alkylene oxide adduct containing a less amount of residual alkylphenol and alkylphenol alkylene oxide adduct has been strongly desired.
As to the process for preparing alkylcyclohexanol ethylene oxide adducts and other alkylcyclohexanol alkylene oxide adducts having a higher alkyl group on a side chain of a cyclohexane ring, several processes have been known as shown below.
For example, German Laid-Open Patent 4417947 has disclosed a process for obtaining alkylcyclohexanol by hydrogenation of alkylphenol and successively reacting with ethylene oxide in the presence of a basic catalyst to prepare alkylcyclohexanol ethylene oxide adducts. However, the process leads to a relatively broad addition distribution of ethylene oxide, increases proportion of high molar adduct, and thus results in a solid reaction product which is unfavorable because of difficulty in handling as a surfactant. Further, the reaction of alkylcyclohexanol and other secondary alcohols with ethylene oxide in the presence of a basic catalyst has been generally known to have a very low reaction rate. For example, it has been described in H. Horiguchi (“New Surfactants”, page 626, published by Sankyo Shuppan Co. (1975) that ethylene oxide generally reacts very quickly with primary alcohol whereas slowly with secondary alcohol in the presence of a basic catalyst. Consequently, in the preparation of an alkylcyclohexanol ethylene oxide adduct by reaction of alkylcyclohexanol with ethylene oxide in the presence of a basic catalyst, a small amount of alkylcyclohexanol ethylene oxide adduct (primary alcohol) formed in the initial stage of the reaction preferentially reacts with ethylene oxide. As a result, unreacted alkylcyclohexanol remains in an extremely large quantity.
H. Stache et al. have obtained one molar ethylene oxide adduct of isooctylcyclohexanol by hydrogenation of one molar ethylene oxide adduct of isooctylphenol and have successively reacted the product with ethylene oxide to obtain isooctylcyclohexanol ethylene oxide adduct (Tr.-Mezhdunar. Kongr. Poverkhn.-Akt Veshchestvam 7th, Vol. 1(1977), 378-391). However, as to the hydrogenation reaction of one molar ethylene oxide adduct of isooctylphenol, no description can be found at all on the species of the catalyst used and the reaction conditions carried out. Further, no specific purification has been carried out after the hydrogenation reaction. Quite no description has been found on the amount of isooctylphenol ethylene oxide adduct remaining in the isooctylcyclohexanol ethylene oxide adduct thus obtained.
Further, German Patent No. 626965 has also obtained alkylcyclohexanol alkylene oxide adduct by the same process as that of H. Stache et al. The process also did not carry out specific purification of hydrogenation product. No description is found at all on the amount of alkylphenol alkylene oxide adduct remaining in the resulting alkylcyclohexanol alkylene oxide adduct.
Further, George E. Tillar et al. have obtained octylcyclohexanol ethylene oxide adduct by hydrogenation of octylphenol ethylene oxide adduct (Trade Mark: Triton X-100) in an ethanol solvent in the presence of a rhodium carbon catalyst (Analytical Biochemistry 141, 262-266 (1984)). The cited example has suggested that such a process remains 600 ppm of octylphenol ethylene oxide adduct even though the reaction time of hydrogenation is extended.
As mentioned above, several suggestions have been found on the preparation process of alkylcyclohexanol alkylene oxide adducts. However, in the present state of the art, almost no information has been obtained on the preparation process of alkylcyclohexanol alkylene oxide adducts which contain a reduced amount of residual alkylphenol and alkylphenol alkylene oxide adduct, have higher purity and narrow addition distribution of alkylene oxide.
Therefore, the object of the invention is to provide a high purity alkylcyclohexanol alkylene oxide adduct which has a narrow addition distribution of alkylene oxide and contains a trace amount or less of alkylphenol and alkylphenol alkylene oxide adduct, a simple and efficient preparation process of alkylcyclohexanol alkylene oxide adduct, and uses of the same.
SUMMARY OF THE INVENTION
As a result of an intensive investigation in order to solve the above subjects, the present inventors have found a process for efficiently preparing an alkylcyclohexanol alkylene oxide adduct which has a narrow addition distribution of alkylene oxide, contains a trace amount or less of impurities including alkylphenol and alkylphenol alkylene oxide adduct, and is represented by the formula (1). Thus the present invention has been completed.
That is, the first aspect of the invention is an alkylcyclohexanol alkylene oxide adduct which contains 200 ppm or less of alkylphenol and alkylphenol alkylene oxide adduct and is represented by the formula (1):
wherein R
1
is an alkyl group having 6 to 20 carbon atoms, R
2
is a hydrogen atom, methyl or ethyl group, and n is an integer of 1 or more.
The second aspect of the invention is a preparation process of an alkylcyclohexanol alkylene oxide adduct which contains a trace amount or less of alkylphenol alkylene oxide adduct and is represented by the formula (1), comprising hydrogenating alkylphenol alkylene oxide adduct represented by the formula (2):
wherein R
1
is an alkyl group having 6 to 20 carbon atoms, R
2
is a hydrogen atom, methyl or ethyl group, and n is an integer of 1 or more, 1) in the absence of a solvent, 2) in the presence of a saturated hydrocarbon solvent, or 3) in the presence of water.
The third aspect of the invention is a preparation process of a high purity alkylcyclohexanol alkylene oxide adduct which has a narrow addition distribution of alkylene oxide and is represented by the formula (1), comprising adding one mole of alkylene oxide having 2 to 4 carbon atoms to alkylphenol represented by the formula (4):
wherein R
1
is an alkyl group having 6 to 20 carbon atoms, thereafter hydrogenating and distillating to obtain alkylene oxide one molar adduct of alkylcyclohexanol which contains a trace amount of alkylphenol and alkylphenol alkylene oxide adduct, and successively adding alkylene oxide in the presence of a basic catalyst.
The fourth aspect of the invention is a preparation process of a high purity a
Fukuoka Daisuke
Inoue Yoshihisa
Motoyama Yoshio
Okita Masumi
Ono Yasuko
Keys Rosalynd
Mitsui Chemicals Inc.
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