Corrosion and gas hydrate inhibitors having improved water solubility and increased biodegradability
View Patent ↗The invention provides the use of compounds of the formula (1) where R 1 , R 2 are each independently C 1 - to C 22 -alkyl, C 2 - to C 22 -alkenyl, C 6 - to C 30 -aryl or C 7 - to C 30 -alkylaryl, R 3 is C 1 - to C 22 -alkyl, C 2 - to C 22 -alkenyl, C 6 - to C 30 -aryl or C 7 - to C 30 -alkylaryl, —CHR 5 —COO − or —O − , R 4 is M, hydrogen or an organic radical which optionally contains heteroatoms and has from 1 to 100 carbon atoms, A is a C 2 - to C 4 -alkylene group, B is a C 1 - to C 10 -alkylene group, D is an organic radical which optionally contains heteroatoms and has from 1 to 600 carbon atoms, X, Y are each independently O or NR 6 , R 5 , R 6 are each independently hydrogen, C 1 - to C 22 -alkyl, C 2 - to C 22 -alkenyl, C 6 - to C 30 -aryl or C 7 - to C 30 -alkylaryl, and M is a cation n is a number from 1 to 30 as corrosion inhibitors and gas hydrate inhibitors, and also the compounds of formula 1.
1. A method for inhibiting corrosion and gas hydrate formation, said method comprising adding to a mixture of hydrocarbons and water a compound of formula (1)
where
R 1 , R 2 are each independently C 1 - to C 22 -alkyl, C 2 - to C 22 alkenyl, C 6 - to C 30 -aryl or C 7 - to C 30 -alkylaryl,
R 3 is C 1 - to C 22 -alkyl, C 2 - to C 22 -alkenyl, C 6 - to C 30 -aryl or C 7 - to C 30 -alkylaryl, —CHR 5 —COO − or —O − ,
R 4 is a radical of the formula (2)
m is a number from 0 to 30,
A is a C 2 - to C 4 -alkylene group,
B is a C 1 - to C 10 -alkylene group,
D is an organic radical optionally containing heteroatoms and has from 1 to 600 carbon atoms, said organic radical being selected from the group consisting of
a straight-chain or branched C 2 - to C 50 -alkylene group or a straight-chain or branched C 2 - to C 50 -alkenylene group which is derived from a saturated or unsaturated dicarboxylic acid,
a C 6 - to C 50 -aryl radical or a C 6 - to C 50 -arylalkyl radical which is derived from a benzenedicarboxylic acid, and
a radical of formula (3)
where R 7 and R 12 are each either hydrogen or a C 2 - to C 100 -alkyl or C 2 - to C 100 -alkenyl radical and wherein bonding of D occurs through any valence within R 7 or R 12
X, Y are each independently O or NR 6 ,
R 5 , R 6 are each independently hydrogen, C 1 - to C 22 -alkyl, C 2 - to C 22 -alkenyl, C 6 - to C 30 -aryl or C 7 - to C 30 -alkylaryl, and
n is a number from 1 to 30.
2. The method of claim 1 , wherein A is an ethylene or propylene group.
3. The method of claim 1 , wherein B is a C 2 - to C 4 -alkylene group.
4. The method of claim 1 , wherein R 1 and R 2 are each independently an alkyl or alkenyl group of from 2 to 14 carbon atoms.
5. The method of claim 1 , wherein R 3 is an alkyl or alkenyl group having from 1 to 12 carbon atoms.
6. The method of claim 1 , wherein R 5 and R 6 are hydrogen.
7. The method of claim 1 , wherein n is a number in the range from 1 to 10.
8. The method of claim 1 , wherein D is a C 2 - to C 50 -alkylene or C 2 - to C 50 -alkenylene group.
9. The method of claim 1 , wherein D is derived from a substituted succinic acid derivative having from 10 to 100 carbon atoms.
10. The method of claim 1 , wherein D is a radical of the, formula (3)
where
R 7 and R 12 are each either hydrogen or a C 2 - to C 100 -alkyl or C 2 - to C 100 -alkenyl radical which is obtainable as an oligomer of C 2 - to C 8 -alkenes and may be straight-chain or branched, with the proviso that exactly one of the R 7 and R 12 radicals is hydrogen wherein bonding of D occurs through any valence within R 7 or R 12 , and R 1 , R 2 are each independently C 1 - to C 22 -alkyl, C 2 - to C 22 -alkenyl, C 6 - to C 30 -aryl or C 7 - to C 30 -alkylaryl,
R 3 is C 1 - to C 22 -alkyl, C 2 - to C 22 -alkenyl, C 6 - to C 30 -aryl or C 7 - to C 30 -alkylaryl, —CHR 5 —COO − or —O − ,
R 4 is a radical of the formula (2)
A is a C 2 - to C 4 -alkylene group,
B is a C 1 - to C 10 -alkylene group,
X, Y are each independently O or NR 6 ,
n is a number from 1 to 30.