Alkyl sulfate ester or salt of same
An alkyl sulfate ester containing a carbonyl group or a salt thereof. The compound is represented by the following formula: R 1 —C(—O)—(CR 2 2 ) n —(OR 3 ) p —(CR 4 2 ) q -L-OSO 3 X wherein R 1 , R 2 , R 3 , R 4 , L, X, n, p and q are as defined herein. Also disclosed is a production method for making the alkyl sulfate ester.
1. A compound represented by the following formula:
wherein
R 1 is a methyl group;
R 2 is H and R 4 is H or a substituent;
R 3 is a C1-C10 alkylene group optionally containing a substituent;
n is an integer of 1 or greater;
p and q are each individually an integer of 0 or greater;
X is H, a metal atom, NR 5 4 , imidazolium optionally containing a substituent, pyridinium optionally containing a substituent, or phosphonium optionally containing a substituent, where R 5 s are each H or an organic group and are the same as or different from each other;
L is a single bond, —CO 2 —B—*, —OCO—B—*, —CONR 6 —B—*, —NR 6 CO—B—*, or —CO—, where B is a single bond or a C1-C10 alkylene group optionally containing a substituent, R 6 is H or a C1-C4 alkyl group optionally containing a substituent, and * indicates the bond to —OSO 3 X in the formula;
a total number of carbon atoms in the compound is 5 to 30; and
the compound excludes 11-keto dodecyl sulphate.
2. The compound according to claim 1 ,
wherein L is a single bond.
3. The compound according to claim 1 ,
wherein R 4 is H or a C1-C4 linear or branched alkyl group.
4. The compound according to claim 1 ,
wherein R 3 is a C1-C4 alkylene group free from a substituent.
5. The compound according to claim 1 ,
wherein X in the formula is a metal atom or NR 5 4 .
6. The compound according to claim 1 ,
wherein the compound is an aqueous dispersant.
7. A production method for producing the compound of claim 1 , the method comprising:
a step of oxidizing a compound represented by the following formula (10):
R 11 —CH═CH—(CR 2 2 ) n —(OR 3 ) p —(CR 4 2 ) q -L-OH (10)
wherein
R 2 is H and R 4 is H or a substituent;
R 3 is a C1-C10 alkylene group optionally containing a substituent;
n is an integer of 1 or greater;
p and q are each individually an integer of 0 or greater;
R 11 is H; and
L is a single bond, —CO 2 —B—*, —OCO—B—*, —CONR 6 —B—*, —NR 6 CO—B—*, or —CO—, where B is a single bond or a C1-C10 alkylene group optionally containing a substituent, R 6 is H or a C1-C4 alkyl group optionally containing a substituent, and * indicates the bond to —OH in the formula (10),
to provide a compound represented by the following formula (41):
wherein R 2 to R 4 , R 11 , L, n, p, and q are defined as described above in formula (10); and
a step of sulfuric-esterifying the compound represented by formula (41) to provide a compound represented by the following formula (42):
wherein X is H, a metal atom, NR 5 4 , imidazolium optionally containing a substituent, pyridinium optionally containing a substituent, or phosphonium optionally containing a substituent, where R 5 s are each H or an organic group and are the same as or different from each other; and
wherein R 2 to R 4 , R 11 , L, n, p, and q are defined as described above in formula (10).
8. The production method according to claim 7 ,
wherein L is a single bond.