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Патент USA US3098049

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United States Patent O?ice
Patented July 16, 1963
perhaps lowered to control effectively the bacteria count
of the ?ooding water.
Edward B. Hodge, Terre Haute, Ind., assignor to Com
mercial Solvents Corporation, New York, N.Y., a cor
Alternately the bactericides utilized in my process can
be ‘added to the oil-bearing formations periodically, for
poration of Maryland
N0 Drawing. Filed Oct. 28, 1960, Ser. No. 65,566
4 Claims. (Cl. 252-8.55)
example, once a week as a high-potency concentrate, or
the undiluted bactericide may be injected into the forma
I have found that the compounds utilized in my process
My invention relates to the control of bacteria in water
are active against some strains of bacteria in water at
?ooding operations used in the secondary recovery of 10 concentrations as low as 10—25 p.p.m. and at times as
petroleum oils and more particularly to the control of
high as 100 p.p.m. as I have found that even very resistant
such organisms by incorporating into the ?ooding water
strains of Desu'lfovibrio desulfuricans are effectively con
trolled at these concentrations.
It is to be understood, of course, that not all of the
re?ecting amounts of esters for-med from the condensation
of lower nitroalkanols and alkyl carboxylic acids selected
vfrom the group consisting of dibasic and tribasic acids 15 compounds used in my process are effective to the same
having up to and including six carbon atoms.
degree. The following table sets out the concentrations
U.S. Patent 2,839,467 lists many of the problems ‘found
at which I have found representative nitro-substituted alkyl
in the secondary oil recovery art and the means whereby
esters to be completely e?ective against resistant strains of
some of these problems have been solved. The problem
Deswlfovibrio desltlfuricans in water-?ooding operations.
of controlling sulfate-reducing bacteria is ever present
Effective concen
and always dif?cult as the growth of the microorganisms is
Nitro-substituted alkyl esters:
tration, ppm.
not controlled by economically practical amounts of many
Bis(2-nitrobutyl) adipate __________________ __ 10
bacteri'cides generally utilized in bacterial control and the
Tris(Z-nitrobutyl) citrate __________________ __ 25
microorganisms sometimes ‘become resistant to ‘generally
used bactericides.
The problems attending the control of microorganisms
Bis(2-nitrobutyl) tartrate __________________ __ 10
easily solved but are, nevertheless, present. These orga
The ‘following examples illustrate the use of my nitro
substituted alkyl esters in the control of sulfate-reducing
microorganisms in water ?ooding operations. It is not
nisms are generally controlled by moderate amounts of
known bactericides.
I have now discovered that noxious organisms present
in water ?ooding operations are economically controlled
intended that my invention be limited to the exact compo
sitions or concentrations shown. Rather, it is intended
that all equivalents obvious to those skilled in the art ‘be
included within the scope of my invention as claimed.
other than those of the sulfate-reducing type are more
by nitro-substituted alkyl esters formed from the conden
Example I
sation of lower nitroalkanols and alkyl carboxylic acids
In a ‘water-treatment plant, a water concentrate contain
selected from the group consisting of dibasic and tribasic 35
ing bis(Z-nitrobutyl) ad-ipate is continuously added to
acids having up to and including six carbon atoms. Com
water to be pumped into subterranean oil-bearing forma
pounds which I have found to be operative in my present
tions at such a rate that a 25 ppm. solution of the com
process include bis(Z-nitrobutyl) adipate, tris(2-nitro
pound is formed.
butyl) citrate, bis(Z-nitrobutyl) tartrate, bis(2-nitrobutyl)
oxalate, bis(Z-nitroethyl) adipate.
The nitro-substituted alkyl esters utilized in my inven
tion can be produced by the condensation of a lower nitro
al'kanol with a dibasic or tribasic acid in the presence of
an acid catalyst.
In preparing the nitro-substituted alkyl
esters by condensation of a lower nitroalkanol with a di
basic ‘or tribasic acid, I prefer to first form a benzene solu
tion of the acid and the nitroalcohol using approximately
a 10% excess of the theoretically reactant amount of the
nitroalcohol, re?ux the said solution in the presence of an 50
acid catalyst such as sulfuric acid or paratoluenesulfonic
acid until the ?nal product is formed in the reaction mix
ture. The product is then recovered from the reaction
mixture by subsequently cooling, washing, and concentrat
The thus treated ?ooding water is
40 pumped into the oil-bearing formation and is completely
effective in preventing bacterial plugging of the oil-bearing
sands in the piping system utilized in the water-?ooding
Example II
Utilizing the process of Example I, I have found that
25 ppm. of tris(2-nitrobutyl) citrate is effective in control
ling sulfate-reducing bacteria in water-?ooding operations.
Example [11
Utilizing the process of Example I, I have found that
10 ppm. of bis(2-nitrobutyl) tartrate is effective in con
trolling sulfate-reducing bacteria in water-?ooding opera
Example IV
ing the mixture to obtain the desired product.
Utilizing the process of Example I, I have found that
The usual procedure ‘for treatment of water to be uti—
100 ppm. ‘of bis(2-nitrobutyl) oxalate is effective in con
lized in ?ooding operations is to produce a concentrate
trolling sulfate-reducing bacteria in water-?ooding opera
of the 'bactericide in water and then continuously inject
this concentrate into the water to be used in ?ooding oper
Now having described my invention, what I claim is:
ations at a rate which forms a desired dilution of the bac 60
1. In a process of secondary oil recovery characterized
tericid-e. This is done prior to pumping the water into the
by the step of injecting ?ooding water into oil-bearing
‘oil-bearing subterranean formation. Sampling and check
subterranean formations to displace portions of the residual
ing of the water for sulfate-reducing bacteria will show
oil therein, the improvement which comprises incorporat
whether the chemical concentration needs to be raised or
ing in the said injected ?ooding water in excess of 10-25
parts per million of a nitro-substituted alkyl ester formed
‘from the condensation of lower nitroalkanols and alkyl
carboxylic acids selected from the group consisting of tar
tar'ic acid, citric ‘acid, and adipic acid to inhibit the growth
Stayner 6t #1 ----------- -- Oct‘ 19, 1954
()f 2.
The process of
1 wherein the nitro-substituted 5
Bennett et ‘a1
—- Man
APr- 21,
11, 1961
alkyl ester is bis(2-nitrobuty1) adipate.
3. The process of claim 1 wherein the nitro-substituted
Bennett “'31 ——————————— —- SePt- 26, 1961
ialkyl ester is tris(2-nitrobuty-1) citrate.
4. The process of claim 1 wherein the nitro-substituted 10
'alkyl ester is bis(2-nitrobuty1) t-artrate.
References Cited in the ?le of this patent
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