Note: Descriptions are shown in the official language in which they were submitted.
1 336843
i
Esterified glycidyl ether addition products and their use
Description
The invention relates to esterified glycidyl ether addi-
tion products and the use of these products.
In the production of crude oil, dilution of the oil with
water is increasingly occurring. The associated water
which is produced forms a water-in-oil emulsion with the
oil. Salts such as sodium chloride, calcium chloride and
magnesium chloride may be dissolved in the emulsified water.
This water of emulsion must be separated before transpor-
tation. The salt content is further reduced by formation
of a new emulsion with fresh water and demulsification in
the refineries before distillation. If the salt content in
the crude oil is too high, this can lead to malfunctions
and corrosion in the refineries.
A crude oil splitter, also called a demulsifier or emulsion
splitter, has the purpose, when used at the lowest possible
concentration, of breaking the emulsion and in this sepa-
ration process, as far as possible, without or with mini-
mal additional use of heat, to cause a complete separationof water and to reduce the salt content to a minimum. The
quality criteria for delivered crude oil are the residual
salt content and the water content.
Crude oils have different compositions according to their
source. Natural emulsion stabilizers have a complex,
multifarious chemical structure. In order to overcome
their effect, splitters must be developed selectively.
The requirements which are placed on a crude oil splitter
are made more varied by different production and proces-
sing conditions. Since new oil fields are continuallybeing developed and the production conditions of old oil
dL
- 2 - 1 3 3 6 8 4 3
fields are altered, the development of optimal demulsi-
fiers remains an acute problem, and a large number of
differently constituted demulsifiers or demulsifier mix-
tures are needed.
CA Patent 1,153,356 has disclosed glycidyl ether addi-
tion products as thickening agents for hydraulic fluids
based on glycol-~ater. The subject matter relates in par-
ticular, inter alia, to addition products made from ethy-
lene oxide/propylene oxide block polymers and diglycidyl
ethers of bisphenols or polyglycidyl ethers of phenol/
formaldehyde condensation products (novolak resins). In
the two US Patents 4,419,265 and 4,420,413, addition
products made from ethylene oxide/propylene oxide block
polymers and glycidyl ethers are described as crude oil
splitters. The crude oil splitters of US Patent 4,419,265
are obtained by addition of an ethylene oxide/propylene
oxide block polymer to a diglycidyl ether of bisphenols,
and that of the US Patent 4,420,413 by follo~ing the
addition step mentioned by an oxalkylation with ethylene
oxide, propylene oxide and/or butylene oxide.
In European Patent Application 0,209,850, esterification
products made from oxalkylated primary fatty amines,
ethylene oxide/ propylene oxide block polymers and
dicarboxylic acids are described as crude oil splitters,
and according to European Patent Application 0,212,265
further crude oil splitters are obtained by quaternizing
the esterification products mentioned. All of these
kno~n crude oil splitters leave something to be desired.
In the present invention, ne~ crude oil splitters are
provided, which are esterification products made from
oxalkylated primary fatty amines (1), addition compounds
made from ethylene oxide/propylene oxide block polymers
and glycidyl ethers (2) and dicarboxylic acids (3). The
esterified glycidyl ether addition products according to
the invention thus differ from the esterification products
according to European Patent Application 0,209,850 in
1 336843
-- 3
- that the component (2) is not an ethylene oxide/propy-
lene oxide block polymer as such, but rather an addition
compound made from block polymers of this kind and
glycidyl ethers according to the US Patents 4,419,265 and
4,420,413. It is surprising, that by this substitution,
crude oil splitters having an even further enhanced
effectiveness are obtained. This high effectiveness may
be due to the particular structure of the reaction
products, which result from the combination according to
the invention of the components mentioned (1) and (3)
with the particular adduct compound (2).
The addition products according to the invention are
accordingly those wherein they are obtained by esterifi-
cation of (1) an oxalkylated primary fatty amine of the
following formula I
R
(fH2CHO) a~H
R -N
(CH2CHO)b-H
R2
in which R1 is an alkyl radical or an alkenyl radical
having 6 to 23 carbon atoms, R2 is H or CH3 and may al-
so take both meanings within the chain of the polyoxalkylene
radical, arranged in blocks, and a and b are numbers
whose sum is 2 to 30, with the provision that neither
a nor b is zero,
and (2) an addition product made from 1 mol OH function of
a polyether block polymer of the following formula II
HO(CH2CH2O)m-(CH2CHO)p-(CH2CH2O)nH
R3
in which ~3represents methyl or ethyl, n and m are numbers,
which are selected in such a way that the proportion of
polyethylene oxide is 10 to 80 % of the molecular weight
of the total molecule, and p is a number from 10 to 100,
and 0.3 to 1 mol epoxide function of a glycidyl ether of
the following formula III
1 336843
- R4 R4 - R4 R4
CH2-CH-CH2-0 ~ A ~ 0-CH2-1CH CH2 0 ~ ~ 2 \/
in which R4 may be identical or different and represents
hydrogen, C1-C4-alkyl or halogen, A a direct bond, a
sulfonyl or cyclohexyl group or a group of the formula
R5_c_R6
R5 and R6 = hydrogen, methyl or phenyl, and x a number
from 0 to 10,
or 0.1 to 1.5 mol epoxide function of a glycidyl ether of
the following formula IV
-CH2-CH-CH2 0-CH2-CH-CH2 0 CH C~H~CH
~ CH2 ~ CH2
in which y is a number from 1 to 10,
with (3) a dicarboxylic acid, in which the reaction com-
ponents (1), (2) and (3) are used in the ratio of equiva-
lents 1 : (0.1 to 1.5) : (0.5 to 2).
Preferred oxalkylated primary fatty amines of the formula
I are those in which R1 is an alkyl radical having 8 to
18 carbon atoms, R2 is H and a and b are numbers (identi-
cal or different, whole or fractional) totalling 2 to 15,
in compliance with the provision mentioned above.
The oxalkylation of primary fatty amines is well known and
can be carried out by one of the methods for oxalkylating
compounds carrying acidic (active) hydrogen atoms. The
oxalkylated fatty amines may carry, in accordance with the mean-
ings R , units of ethylene oxide or propylene oxide or
units of ethylene oxide and propylene oxide
_ 5 _ 1 3 3 6 8 4 3
_ arranged in blocks, the ethoxylated primary
fatty amines, i.e. those carrying only ethylene oxide units,
being preferred. Where fatty amines used for oxalkyl-
ation are concerned, in accordance with the meanings of
R1, these may be individual primary fatty amines or a
mixture of these. This may also include those fatty amines,
whose hydrocarbon chain contains one or more double bonds,
such as the radicals of oleic acid, linoleic acid or lino-
lenic acid. The preferred primary fatty amines are the
industrially available products, such as stearylamine,
coconut fatty amine or tallow fatty amine (alkyl radicals
having essentially 8 to 18 carbon atoms are present in
these industrial products).
Preferred polyether block polymers of the formula II are
those, in which R3 is CH3 and n and m are numbers, which
are selected in such a way that the proportion of poly-
ethylene oxide is 15 to 70 % of the molecular weight of
the total molecule, and p is a number from 20 to 70.
Preferred glycidyl ethers of the formula III, which are
diglycidyl ethers of bisphenols, are those in which R4 is
identical in each case and represents hydrogen, A is a
group of the formula
R5_c_R6
in which R5 and R6 are identical and represent H or
CH3, and x is a number from 0 to 5.
Preferred glycidyl ethers of the formula IV, which are
polyglycidyl ethers of phenol/formaldehyde condensation
products, are those in which y is a number from 2 to 5
(the -CH2- bridges in the formula IY are located as is
well known, essentially in the ortho- and para-position
on the phenyl nucleus).
The preparation of the reaction component (2) is carried
out by addition of a polyether block polymer of the formula
- 6 - 1 3 3 6 8 4 ~
II to a glycidyl ether of the formula III in the ratio of
equivalents 1 : 0.3 to 1, preferably 1 : 0.5 to 0.9,
or to a glycidyl ether of the formula IV in the ratio of
equivalents 1 : 0.1 to 1.5, preferably 1 : 0.3 to 1.
It has been found that crude oil splitters having a parti-
cularly good effectiveness are obtained when the reaction
component (2) is propoxylated, thus when the addition pro-
duct mentioned made from a polyether block polymer of the
formula II and a glycidyl ether of the formula III or of
the formula IV is propoxylated with 5 to 700 9 propylene
oxide, preferably 30 to 300 9 propylene oxide, per 100 9
addition product.
The polyether block polymers of the formula II and the
glycidyl ether of the formulae III and IV and the conver-
sions of these components to the relevant addition pro-
ducts, which are defined as the reaction component (2) of
the present invention, are so fully described in the publi-
cations initially mentioned, that it is superfluous to go
into more detail here. Moreover, they are commercially
obtainable.
The dicarboxylic acid which is to be used, which is the
reaction component (3), may be of the aromatic or
aliphatic type. The aromatic dicarboxylic acid is pre-
ferably phthalic acid. The aliphatic dicarboxylic
acids may be saturated or unsaturated, such as fumaric
acid and maleic acid. Poth the usual dicarboxylic acids
of the formula HOOC-(CH2)z-COOH, in which z is a number,
preferably from 1 to 8 and in which one or more CH2 groups
may be substituted by OH-, C1 to C1g-alkyl or by C3 to
C1g-alkenyl, and those in the form of dimerized fatty
acids corresponding to the formula HOOC-R-COOH, in which
R is the alkyl skeleton of a dimerized fatty acid having
preferably 22 to 42 carbon atoms, particularly 34 carbon
atoms, are suitable. Preferred dimerized fatty acids are
those which are obtainable commercially under the trade-
name Pripol. These dimerized fatty acids contain as is
well known essentially linear and cyclical compounds and
~ 7 ~ 1336843
_ proportions of trimeric and more highly condensed fatty
acids. Examples of the usuaL dicarboxylic acids men-
tioned are succinic acid, adipic acid, pimelic acid and
sebacic acid as well as dodecylsuccinic acid or dodecenyl-
succinic acid, malic acid and tartaric acid. The dicar-
boxylic acids which are preferred as reaction component
(3) are accordingly a) those of the formula HOOC-(CH2)z-
COOH, in which z is a number from 1 to 8, b) the C1 to
C1g-alkyl- or C3 to C1g-alkenyl-substituted dicarboxylic
acids of the formula mentioned, such as dodecylsuccinic
acid or dodecenylsuccinic acid, c) the dimerized fatty
acids of the formula HOOC-R-COOH, in which R is the alkyl
skeleton of a dimerized fatty acid having 22 to 42 car-
bon atoms, particularly having 34 carbon atoms, d) fumaric
and maleic acid and e) phthalic acid. It is evident that
instead of dicarboxylic acid, dicarboxylic acid anhydride,
dicarboxylic acid halides or esters of dicarboxylic
acids may be used, since the esterification reaction
according to the invention also proceeds with these dicar-
boxylic acid derivatives.
The characteristic feature of the esterification of the
reaction components described (1), (2) and (3) for the pro-
duction of crude oil splitters according to the invention
is the ratio of equivalents, in which the three components
are used; it is 1 : (0.1 to 1.5) : (0.5 to 2), preferably
1 : (0.3 to 1) : (0.7 to 1.5). The esterification occur-
ring with polycondensation can be carried out using a high
boiling inert solvent, such as toluene or xylene, or with-
out solvent in the melt and under a blanket of a protect-
ive gas, operation in the melt being preferred. In esteri-
fication with a solvent the reaction temperature is expe-
diently selected as the reflux temperature of the reac-
tion mixture and the water which is formed from the reac-
tion is removed by azeotropic distillation. In esterifi-
cation in bulk the water from the reaction is driven offdirectly from the reaction mixture. Here the reaction
temperatures are 60 to 200C, preferably 80 to 160C.
In order to speed up the reaction an alkaline or acid
1 336843
-- 8
catalyst is used, as is expedient for esterification
reactions, acid catalysis being preferred. The course and
the end of the reaction can be checked using the water
produced by the reaction or by determination of the amine
or acid number.
A preferred process for the production of the
novel crude oil splitters is described in more detail as
fo~lo~s.
The oxalkylated fatty amine, the addition compound made
from polyether block polymers and glycidyl ethers and the
dicarboxylic acid as well as the acid catalyst are placed
in a reaction vessel. Suitable acid catalysts are halo-
gen hydracids, phosphoric acids, sulfuric acid, sulfonic
acids and halogenoacetic acids. Hydrochloric acid, phos-
phoric acids and sulfonic acids are preferred. The quan-
tity of acid as catalyst is generally 0.05 to 5 % by
~eight, preferably 0.1 to 1 % by weight, based on the total
~eight of the three reaction components. A particularly
advantageous catalyst for the esterification reaction
ZO according to the invention is a mixture of one of the
acids mentioned and an alkyl titanate or alkyl polytitan-
ate. Alkyl titanates of the formula Ti(OR')4, are pre-
ferred, in which R' is an alkyl radical having 1 to 18 car-
bon atoms, preferably having 1 to 6 carbon atoms, and
alkyl polytitanates of the formula R'O~CTi(OR')20]q~R', in
~hich R' has the meaning mentioned and q is a number from
1 to 10, preferably from 4 to 7. As a rule, the quantity
of titanate is 0.5 to 2 % by ~eight, preferably 0.1 to 1 %
by ~eight, the percentages by ~eight being based on the total
~eight of the three reaction components. This quantity of
acid is also used, if the relevant combination of acid and
titanate is used as catalyst.
The mixture of the three reaction components and the este-
rification catalyst which has been placed in the reaction
vessel is heated ~ith stirring, ~hile an inert gas is
passed through it, to 60 to 200C, preferably 80 to 160C,
_ 9 _ 1 336843
_ and maintained at this temperature while the water produced
is continuously removed, until the conversion is completed.
The removal of the water from the reaction can also be
achieved using a vacuum of for example 1300 to 2600 Pa
(water-jet vacuum). The esterification product obtained
can be freed from the catalyst used by washing with water.
The reaction time is in the range of 5 to 20 hours. The
esterification products according to the invention occur as
yellow or brown colored liquids. They have specific chemi-
cal properties and a specific structure and have a visco-
sity of 2000 to 60,000 mPa . s, preferably 4000 to 40,000
mPa . s.
It has been found, that the effectiveness of the esteri-
fied glycidyl ether addition products according to the
invention, particularly in relation to corrosion inhibition
can be further improved, when it is quaternized, prefer-
ably with 1 to 15 mol ethylene oxide or propylene oxide
per nitrogen atom in the presence of a quantity of a mine-
ral acid or a carboxylic acid (the acids used supply the
anion in the quaternization reaction; the number of nitro-
gen atoms in the esterified glycidyl ether addition pro-
duct can for example be found by determining the amine
number), in a quantity equivalent to the number of nitro-
gen atoms. The quaternization, which is preferably car-
ried out using ethylene oxide, is performed at a tempera-
ture of 60 to 110C, preferably 70 to 90C. The degree
of quaternization of the product obtained can be measured
by two-phase titration with sodium dodecyl sulfate at pH
1 to 2 or pH 10. The quaternary esterified glycidyl ether
addition products obtained according to the invention
occur as yellow to brown colored, resin-like substances
and are described by their degree of quaternization, which
should according to the invention be 30 to 99 ~, preferably
60 to 98 %.
A preferred method for the relevant quaternization will be
described in more detail as follows. The product to be
quaternized and a quantity of mineral acid or carboxylic
- 10 - I 336$~
acid which is essentially equimolar with the nitrogen-
containing monomer units in the product, are placed in a
suitable autoclave with a stirrer and preferably autoclaved
with ethylene oxide, namely with 1 to 15 mo(, preferably 2
to 10 mol, per mol of nitrogen-containing monomer unit, at
the given temperature. During the autoclaving, for rea-
sons of expediency, a reaction pressure of about 0.3 MPa
is not exceeded. Preferably, hydrohalic acids, phos-
phoric acids, sulfuric acid or sulfonic acids are used as
mineral acids, phosphoric acid being particularly pre-
ferred. Preferably, aliphatic carboxylic acids having
1 to 6 carbon atoms, aliphatic hydroxycarboxylic acids
having 1 to 6 carbon atoms and having 1 to 3 hydroxyl
groups or aromatic carboxylic acids, such as benzoic acid
and salicylic acid are used as carboxylic acids. The car-
boxylic acid may also be an optionally OH-substituted, di-
or tricarboxylic acid. Particularly preferred acids are
acetic acid, propionic acid, glycolic acid, lactic acid
and phosphoric acid. The course and the end of the con-
version can be monitored from the pressure profile in thereaction vessel and/or by determining the degree of quater-
nization. The reaction time is in the range of 10 to
20 hours.
The addition products according to the invention are
distinguished by having a high demulsifying effect.
At normal crude oil processing temperatures, a complete
separation of water and a reduction in the salt content is
achieved even after a short separating time. Thus, with
the novel crude oil splitters crude oils are obtained to
delivery specification at the usual processing temperatures
after a short separating time. They have the additional
effect, that the separated water is practically free of
oiL, and thus that the complete removal of oil from the
separated ~ater is achieved, and thereby a good water
quality. Moreover, with the novel crude oil splitters, a
sharp separation of the oil phase and the ~ater phase is
achieved, which represents a further great advantage.
1 336843
- 11 -
_ The quaternized crude oil splitters according to the
invention have in addition to the properties mentioned a
high corrosion-inhibiting effect.
The quantity of demulsifier according to the invention
which is used may vary between wide limits. It depends
particularly on the type of crude oil and on the proces-
sing temperature. The effective quantity is generally 5
to 100 9 per tonne, preferably 10 to 50 9 per tonne. The
novel splitters are preferably used in solution for the
purpose of better metering and dispersibility. ~ater or
organic liquids are suitable as solvents, for example
alcohols, such as methanol, isopropanol or butanol, aro-
matic hydrocarbons, such as toluene or xylene, and custo-
mary commercial mixtures of higher aromatics.
The invention is now described in more detail by examples:
Initially the addition products made from a polyether
block polymer of the formula II and a glycidyl ether of
the formula III or IV, which are used in the examples, are
described below; these are the addition products (2a)
to (2e).
The addition product (2a) is obtained by addition of 1 mol
hydroxyl function of a polyether block polymer of the for-
mula II having R3 = CH3, m + n = 22, p = 29 and having
a 36.3% proportion of polyethylene oxide, based on the
molecular ~eight of the total molecule, this being 2,668,
and 0.8 mol epoxide function of a glycidyl ether of the
formula III having R4 = H, A = C(CH3)2, x = 0.2 and
weight of an equivalent of the total molecule = 192. The
weight of an equivalent of the addition product is 1,275.
The addition product (2b) is obtained by addition of 1 mol
hydroxyl function of the polyether block polymer mentioned
above and 0.9 mol epoxide function of a glycidyl ether of
the formula IV having y = 3.3 and the weight of an equiva-
lent of the total molecule = 180. The weight of an equiva-
lent of the addition product is 976. The addition pro-
duct (2c) is the addition product (2a) propoxylated with
1 3368~3
- 12 -
_ 50 9 propylene oxide per 100 9 addition product. The
weight of an equivalent is 1,870. The addition product
(2d) is the addition product (2a) propoxylated with 100 9
propylene oxide per 100 9 addition product. The
weight of an equivalent is 2,192. The addition product
(2e) is the addition product (2b) propoxylated with 250
g propylene oxide per 100 9 addition product. The
weight of an equivalent is 1,600. Although the
addition of the relevant polyether block polymers and
glycidyl ethers and the propoxylation of the addition
products are well known, the following comments are
made here about the addition: it ~as carried out, in
particular, in such a way that initially the polyether
block polymer is adjusted to a catalyst content of 0.05
to 3 % by weight, preferably 0.1 to 1 % by weight, with
an aqueous solution of an alkaline catalyst (for
example with an approximately 30 % by weight aqueous
solution of potassium hydroxide), and the mixture was
subsequently converted with the glycidyl ether at a
temperature of 70 to 150C, preferably 80 to 120C.
Example 1
In a reaction vessel, which was equipped with stirrer,
reflux condenser and thermometer were placed 248 9, which
is 0.80 mol hydroxyl function, of an oleylamine condensed
with 8 mol ethylene oxide, which is a fatty amine of the
- 25 formula I having R1 = C1gH3s, R2 = H and a + b = 8
(reaction component 1), 102 9, which is 0.08 mol hydroxyl
function of the addition product (2a) (reaction component
2) and 31.4 9, which is 0.64 mol carboxyl function
maleic anhydride (reaction component 3) as well as 0.76 9,
which is 0.20 % by weight, based on the total weight of
the three reaction components, of a polymeric butyl
titanate of the formula C4HgO~Ti(OC4Hg)20]sC4Hg and 0.90 9
of a 50 % by weight aqueous hypophosphoric acid, which is
0.12 % by weight based on the total weight of the three
reaction components, hypophosphoric acid (H3P02), as
- 13 - 1 336843
- esterification catalysts. The three reactions components
were thus used in a ratio of equivalents of 1 : 0.1 : 0.8.
The mixture was heated and maintained for twc hours at a
temperature of 130 to 140C under water-jet vacuum, while
the reaction components reacted under esterification. As
a post-reaction the mixture was maintained for a further
nine hours at a temperature of 150 to 160C and under
~ater-jet vacuum. The course and the end of the esterifi-
cation reaction was monitored by determining the acid
number. The esterification product obtained at a degree
of conversion of 96 % is a liquid having a viscosity of
25.3 Pas.
Example 2
Reaction components:
(1) Tallow fatty amine with 2 mol ethylene oxide
(2) Addition product (2b)
(3) Dodecenylsuccinic anhydride
Ratio of equivalents of (1) : (2) : (3) = 1 : 1.0 : 1.4
Operation as in Example 1.
Degree of conversion 95 %, viscosity 9.7 Pas.
Example 3
Reaction components:
(1) Stearylamine with 8 mol of ethylene oxide
(2) Addition product (2c)
(3) Adipic acid
Ratio of equivalents of (1) : (2) : (3) = 1 : 0.5 : 0.9
Operation as in Example 1.
Degree of conversion 91 %, viscosity 4.5 Pas.
Example 4
Reaction components:
(1) Tallow fatty amine with 10 mol ethylen oxide
(2) Addition product (2d)
(3) Dimerized fatty acid having an alkyl skeleton with
- 14 - 1 3 3 6 8 4 3
- 34 carbon atoms
Ratio of equivalents of (1) : (2) : (3) = 1 : 0.3 : 0.9
Operation as in Example 1.
Degree of conversion 98.5 %, viscosity 15.4 Pas.
Example 5
Reaction components:
(1) Coconut fatty amine with 15 mol ethylene oxide
(2) Addition product (2e)
(3) Phthalic anhydride
Ratio of equivalents of (1) : (2) : (3) = 1 : 1.5 : 2
Operation as in Example 1.
Degree of conversion 98 %, viscosity 37.0 Pas.
Example 6
The esterification product of Example 1 was quaternized.
In a stirred autoclave were placed 376 9, which is 0.40 mol
nitrogen function of the esterification product of Example
1 and 47 9 of an 85 % by veight aqueous lactic acid (0.44
mol lactic acid) as the anion part in the quaternization
reaction as well as 22 9 water and 533 9 isobutanol as
solvent. The mixture was heated to 80C and was auto-
claved at this temperature with 88 9 (2 mol) ethylene oxide
while maintaining a maximum pressure of 0.25 MPa and a
reaction time of 12 hours in total. Thus, quaternization
was carried out with 5 mol ethylene oxide per mol nitrogen-
containing monomer units. The quaternization product ob-
tained after removal of all volatile components, a resin-
like substance, had a degree of quaternization of 98 %.
Examples 7 to 10
The esterification products of Examples 2 to 5 were quater-
nized, namely with 2 mol ethylene oxide (Example 7), 10 mol
ethylene oxide (Example 8), 5 mol ethylene oxide (Example
9) and 5 mol propylene oxide (Example 10). Operation in
- 15 - 1 336843
_ each case as in Example 6 (the quantity of solvent was
selected as in Example 6 so that the end product in each
case was present as a 50 % solution in isobutanol). The
quaternary esterification products had a degree of quater-
nization of 63 %, 96 %, 95 %, and 72 %.
The crude oil splitters according to the invention from
Examples 1 to 10 were tested in crude oil emulsions. The
results are summarized in the following Tables I and II.
- 16 - 1 336843
-
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- 17 - l 336843
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1 336843
- 18 -
The quaternization products according to the invention of
Examples 6 to 10 were tested for their corrosion-inhibiting
effect. In this test, the loss of eight of plates of
carbon steel having a surface 20 cm was determined. The
plates were dipped for 6 hours in water containing 20 % by
weight sodium chloride at 60C. A carbon dioxide stream
was bubbled through the continually stirred solution for
the duration of the experiment. The inhibition is given
in percentages, in which the control without inhibitor is
0 % as reference quantity (this corresponds to 100 %
weight loss). The tests results are summarized in the
following Table III. They show that the products accor-
ding to the invention, in addition to high splitting
effectiveness also have an outstanding corrosion inhibi-
tion, which should be the case in all plants for the pro-
duction and processing of crude oil and natural gas.
T a b l e I I I
Product from A m o u n t u s e d
Example 10 ppm 40 ppm 60 ppm
% inhibition
6 85.6 85.6 86.8
7 79.2 83.7 84.2
8 80.7 84.8 85.3
9 76.4 80.2 82.3
83.8 85.5 87.0
