Ether diamines amine oxides

Details Ether diamines amine oxides Ether diamines amine oxides

2002-01-22

2002-07-09

Davis, Brian J. (Department: 1621)

Organic compounds -- part of the class 532-570 series

Organic compounds

Amino nitrogen containing

C564S299000

Reexamination Certificate

active

06417401

ABSTRACT:

FIELD OF THE INVENTION
The present invention relates to a series of derivatives of novel ether diamine compounds prepared by the cyanobutylation reaction of an alcohol having 3 to 22 carbon atoms with 2-pentenenitrile to form a branched alkyl ether nitrile. The alkyl ether nitrites formed by the process are hydrogenated to form alkylether amines. The resulting products are then reacted with 2-pentenenitrile or acrylonitrile and hydrogenated to yield a diamine, which can likewise be derivatized. Specifically, the present invention deals with two types of tertiary amines, one made by the reaction of novel ether diamines compounds with ethylene oxide, propylene oxide, butylene oxide or mixtures thereof producing alkoxylated tertiary diamines and the other conveniently made by the reaction of novel ether diamine compounds with formaldehyde and hydrogen producing methylated tertiary diamines. The invention also discloses novel diamine oxides, and quaternary compounds made from said tertiary amines.
BACKGROUND OF THE INVENTION
U.S. Pat. Nos. 4,260,556 and 4,211,725 teach reaction of 2-pentenenitrile with ammonia or ethylenediamine to produce alkylaminonitriles. U.S. Pat. No. 4,496,474 teaches the reaction of 2-pentenenitrile with alkylamines having from 8 to 22 carbons to produce the corresponding nitrile compound. U.S. Pat. No. 5,070,202 teaches a process having improved reaction rate and selectivity in the reaction of 2-pentenenitrile with amines to form alkylaminonitriles by the incorporation of from 15 to 60 weight percent water in the reaction mixture. These references do not include the critical ether linkage needed to make the products of the present invention.
U.S. Pat. No. 5,902,883 to Herkes discloses the cyanobutylation of various amines to make diamines. Herkes uses 3-pentenenitrile, 4-pentenenitrile or mixtures of 3-pentenenitrile and 4-pentenenitrile to make his product. This does not result in the desired branching that comes from the compounds of the present invention, nor does it include the critical ether linkage in the molecule. Herkes has done some work with the cyanobutylation of lower molecular weight alcohols (C3 to C8) to form primary amines. These materials lack the hydrophobicity to be good surface-active agents.
It has now been found that by reacting alcohols with 2-pentenenitrile and hydrogenating to the alkyloxypentyl amines, followed by cyonoethylation or cyonobutylation to form diamines, followed by alkoxylation or methylation to form tertiary amines and in a subsequent step derivitization of said tertiary amines results in products with unique properties. Further reaction to form the salts, quaternary salts, or amine oxides also result in products with unique properties. These include (a) superior liquidity of the resulting products, (b) improved surfactant properties and (c) improved solubility. All of these will become clear as one reads the teachings of the present invention.
SUMMARY OF THE INVENTION
The present invention relates to a series of derivatives of novel ether diamine compounds prepared by the cyanobutylation reaction of an alcohol having 3 to 22 carbon atoms with 2-pentenenitrile to form a branched alkyl ether nitrile. The alkyl ether nitrites formed by the process are hydrogenated to form alkylether amines. The ether amine compounds may be used as raw materials for the preparation of the derivatives of the current invention which are the topic of application Ser. No. 459,562 filed Dec. 13, 1999, now U.S. Pat. No. 6,114,585 issued September 2000, and application Ser. No. 09/566,505 filed May 8, 2000 incorporated herein by reference. The resulting product can be reacted with 2-pentenenitrile and or acrylonitrile and in a subsequent step, hydrogenated, to yield a diamine. Specifically, the present invention deals with two types of tertiary amines. One made by the reaction of novel ether diamine compounds with ethylene oxide, propylene oxide, butylene oxide or mixtures thereof to produce an alkoxylated tertiary diamine, and the other conveniently made by the reaction of novel ether diamine compounds with formaldehyde and hydrogen to produce a methylated tertiary diamine. The invention also discloses novel amine oxides, amine salts and quaternary compounds made from said tertiary diamines.
DETAILED DESCRIPTION OF THE INVENTION
The present invention relates to a series of derivatives of novel ether diamine compounds prepared by the cyanobutylation reaction of an alcohol having 3 to 22 carbon atoms with 2-pentenenitrile to form a branched alkyl ether nitrile. The etheraminonitriles formed by the process are hydrogenated to form alkyl ether amines. The resulting product can be reacted with 2-pentenenitrile or acrylonitrile and hydrogenated to yield a diamine. Specifically, the present invention deals with two types of tertiary amines, one made by the reaction of novel ether diamine compounds with ethylene oxide, propylene oxide or butylene oxide or mixtures thereof producing alkoxylated tertiary diamines and the other made by the reaction of novel ether diamine compounds with formaldehyde and hydrogen producing methylated tertiary diamines. The tertiary ether diamines are also converted to amine oxides and quaternaries.
The compounds of the present invention are diamines and derivatives falling into the following classes:
Class 1—A branched ether diamine conforming to the following structure:
 wherein;
e is 0 or 1;
R
1
is selected from the group consisting of alkyl having 3 to 22 carbon atoms;
R
2
is —(CH
2
CH
2
O)
a
—(CH
2
CH(CH
3
)O)
b
—(CH
2
CH(CH
2
CH
3
)O)
c
—;
a, b and c are independently integers ranging from 0 to 30;
d is 1.
Class 2—An alkoxylated tertiary ether diamine conforming to the following structure:
 wherein,
R
1
is selected from the group consisting of alkyl having 3 to 22 carbon atoms, aryl having 6 to 20 carbon atoms;
R
2
is CH
2
CH
2
O)
a
—(CH
2
CH(CH
3
)O)
b
—(CH
2
CH(CH
2
CH
3
)O)
c
—
a, b and c are independent integers ranging from 0 to 30, with the provision that a+b+c are a minimum of 0 and a maximum of 60;
d is 1;
e is 0 or 1
x, y and z are integers ranging from 0 to 30 with the provision that x+y+z is a minimum of 2 and a maximum of 60.
Class 3—An alkoxylated tertiary ether diamine oxide conforming to the following structure:
 wherein;
R
1
is selected from the group consisting of alkyl having 3 to 22 carbon atoms, aryl having 6 to 20 carbon atoms;
R
2
is CH
2
CH
2
O)
a
—(CH
2
CH(CH
3
)O)
b
—(CH
2
CH(CH
2
CH
3
)O)
c
—
a, b and c are independent integers ranging from 0 to 30, with the provision that a+b+c are a minimum of 0 and a maximum of 60;
d is 1;
e is 0 or 1;
x, y and z are integers ranging from 0 to 30 with the provision that x+y+z is a minimum of 2 and a maximum of 60.
Class 4—A trimethyl tertiary ether diamine conforming to the following structure:
 wherein;
R
1
is selected from the group consisting of alkyl having 3 to 22 carbon atoms, aryl having 6 to 20 carbon atoms;
R
2
is —CH
2
CH
2
O)
a
—(CH
2
CH(CH
3
)O)
b
—(CH
2
CH(CH
2
CH
3
)O)
c
—
a, b and c are independent integers ranging from 0 to 30, with the provision that a+b+c are a minimum of 0 and a maximum of 60;
d is 1;
e is 0 or 1.
Class 5—A trimethyl tertiary ether diamine oxide conforming to the following structure:
 wherein:
R
1
is selected from the group consisting of alkyl having 3 to 22 carbon atoms, aryl having 6 to 20 carbon atoms;
R
2
is —(CH
2
CH
2
O)
a
—(CH
2
CH(CH
3
)O)
b
—(CH
2
CH(CH
2
CH
3
)O)
c
—
a, b and c are independent integers ranging from 0 to 30, with the provision that a+b+c are a minimum of 0 and a maximum of 60;
d is 1;
e is 0 or 1.
Class 6—An ether diamine quaternary conforming to the following structure:
 wherein:
R
1
is selected from the group consisting of alkyl having 3 to 22 carbon atoms;
R
2
is —(CH
2
CH
2
O)
a
—(CH
2
CH(CH
3
)O)
b
—(CH
2
CHCH
2
CH
3
)O)
c
—
a, b and c are independent integers ranging from 0 to 30;
d is 1;
e is 0 or 1;
R
4
and R
5
are selected from the group consisting of —CH
3
and
—(CH

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