DE1149843B - Additive for fuel and lubricating oils - Google Patents

Description

GERMAN

PATENT OFFICE

kl. 23 b 4/02

INTERNATIONAL KL.

C10g; m

S61101IVd / 23b

REGISTRATION DATE: DECEMBER 22, 1958

NOTICE THE REGISTRATION AND ISSUE OF EDITORIAL: JUNE 6, 1963

An important need in many phases of the oil industry has been for improved resources to prevent ferrous metal surfaces from rusting. This problem presents itself in various ways Way. It is z. B. with steam turbine lubrication, especially during the initial operation of new equipment, a particularly serious problem. Rusting is most pronounced in places where the space between bearing surfaces is very small, as with the regulator mechanism. This becomes common caused by water getting into the oil supply, ζ. B. by condensing, occurs and in which Oil is carried through the whole circulation system so that it comes into contact with the ferrous metal surfaces comes, reducing the life of the turbine.

Many materials have been suggested as additives to give lubricating oils anti-rust properties granted. Especially in the case of rust protection in the presence of sea water, as in the Lubrication of marine turbines, most of the connections used have been made of materials which contain two or more carboxylic acid groups (—COOH). Monocarboxylic acids are generally has not been effective for ship purposes.

In the field of fuel oils, where rusting is a fundamental problem, there are other requirements which must also be taken into account. It is known that fuel oils tend to during to form sludge or sediment over long periods of storage. This sediment, of course, has an adverse effect Effect on the operation of the burner because it has a tendency to clog the sieves and nozzles. In addition to the sediment formed during storage, most fuel oils contain other impurities, like rust, dirt, and trapped water. The sediment and the impurities seek to settle on parts of the system, such as nozzles, sieves, filters, etc., thereby clogging them and cause the system to fail.

Another factor related to the storage and handling of fuel oils exists is the "breathing" of the storage vessels. This results in an accumulation of vast amounts of water in the storage containers, giving rise to the problem of roasting in the containers gives. If the oil is removed for shipping, enough water can be carried to prevent rusting of ferrous metal surfaces in pipelines, tankers or the like.

In general, the foregoing difficulties have been common in the fuel oil field Additive for fuel and lubricating oils

Applicant:

Socony Mobil Oil Company, Inc.,
New York, NY (V. St. A.)

Representative: Dr. E. Wiegand,

Munich 15, Nussbaumstr. 10,

and Dipl.-Ing. W. Niemann, Hamburg 1,

Patent attorneys

Claimed priority:

V. St. v. America January 7, 1958

(No. 707 456 and No. 707 472)

Harry John Andress Jr., Pitman, N.J.,

and Paul Yoke Chan Gee,

Woodbury, N.J. (V. St. A.),

have been named as inventors

with a separate additive for each purpose to overcome d. H. with a sediment inhibitor, a Anti-clogging agent and an anti-rust agent. The use of several additives gives rise to problems with regard to the additive tolerance, so that the choice of Additive combinations is limited. In addition, of course, the usage of a plurality of increases Additives in an unacceptable manner reduce the cost of the fuel. It has been suggested two Difficulties, e.g. B. the sediment formation and the clogging of the sieve, with a single additive overcome. As far as is known, however, no single additive has yet been found that is effective against sediment formation, sieve and nozzle clogging and rusting of ferrous metal surfaces.

It has now been found that all three problems, i.e. H. Sediment formation, clogging of the sieve and rusting, can be solved through the use of a single fuel additive. Furthermore, was found that a distillate fuel oil containing small amounts of certain amic acids and their amine

309 599/282

3 4

contains salts, at the same time against all three of the aforementioned succinic acid monoamides are another Difficulty is effectively inhibited. Material, namely motor gasoline, to another

It has further been found that this additive has a purpose than that which can be considered according to the invention In the case of lubricating oils, amic acids are added to provide effective protection against rusting.

of ferrous metal surfaces in the presence of sea 5 The amic acids in question here can water guaranteed. by any method known per se for

According to the invention, as an additive that is used to produce such compounds, is suitable to inhibit the formation of sediments, sieve For the production of the amic acids is in the frame to exclude clogging and rusting of ferrous metal- the present invention claims no protection. she surfaces with which it comes into contact are preferably created by preventing amber, Amic acids of the formula stinic anhydride or maleic anhydride with

an aliphatic primary amine at about 4 to

PTJM η ρ ' ηηητι 30 carbon atoms per molecule heated to the

. To form mono-amide of the acid. This can be done by

15 heating of the mixture of anhydride and amine

a temperature of 65 to 15O ⁰ C for a take place in Apt R '' ntwpHpr period of time is between 1 and 3 hours.

All U.CU. JLV C11LWCU.C1 —_. t λ i * * · Ι · ι -ι τ- »ι -t« τ

The addition occurs easily without the formation of water.

QU Qjj _oc j _er Qjj __ QJJ- The amic acids can also be

²² 20 setting between succinic acid and maleic acid

and the amine with elimination of 1 mol of water

and R is a monovalent alkyl radical with 4 to 30 Koh- per mole of amic acid produced, what lenstoffatomen, z. B. a tertiary alkyl radical with but is less desirable. Care must be taken to ensure 12 to 30 carbon atoms, in which a tertiary one is carried, that the splitting off of 2 mol of carbon atoms directly to the nitrogen atom is avoided, because this is bound to the formation of the means, or their salts with alicyclic imides would lead. Regardless of the phatic primary amines RNH ₂ , in which R has the meaning given above for the formation of the amic acid, to fuel and the salt of it can be easily used by heating equi-lubricating oils, in the case of the use molar amounts of the amic acid with an alidation as a lubricating oil additive, the radical R only has the meaning given above, for example, of the above-mentioned phatic primary amines with about 4 to 30 carbons. Atoms of matter per molecule are produced. The salt-

It is known that a reaction product of at least the forming amine can consist of the same amine 1.25 moles of an alkenylsuccinic anhydride with which is used for the preparation of the amic acid a primary amine as an additive to lubricating oils, or it can be made from a different amine use. It is a succinimide, 35 consist. If the salt forming amine is the same which contains more than one carboxyl group and is not amine which is involved in the formation of the amic acid The salt can thereby be produced around an amic acid such as is used in accordance with the invention A turn has come. be that 2 moles of amine with 1 mole of acid

It is also known to heat a reaction product of anhydride at temperatures at which none substituted succinic anhydride and a 40% water is developed.

add tertiary amine mineral oils. It is about the formation of the amic acids and their

This is a product that has no salt, amide or salts usable amines are the primary alipha-imide represents. It is further the addition of a large table amine with about 4 to 30 carbon atoms each Number of different amides or imides molecule. These are the monoamines with a single one from hydrocarbon-substituted anhydrides to 45 open chain hydrocarbon groups attached to a Mineral oils described. This amide or imide nitrogen atom is bonded. The aliphatic radical however, have a different structure than that of the invention can be saturated or unsaturated and branched according to the additives to be used. It is to be closed or normal chain. Similarly, you can borrowed known, reaction products of certain mixtures of these amines as well as pure amines for Amino alcohols and organic monocarboxylic acids 50 apply.

to be used as an additive for mineral lubricating oils. A very usable and readily available one

All the known additives do not have the standing class of primary amines are the primary amines Properties which distinguish the tertiary-alkyl monoamines, in which a primary Amic acids to be used according to the invention from amino (- NH ^ group to a tertiary carbon sign. 55 atom is bonded, and mixtures thereof. These

It is also known that oil-soluble acyclic secondary amines all contain the end group Aminoalkylenamides to a certain structure

Add light petrol to reduce the build-up of CH ₃

To prevent deposits on carburetor parts.

These acyclic secondary aminoalkyleneamines 60 ρ

possess a structure entirely different from that of the
according to the invention to be used amic acids is different. ³

The addition of certain monoamides of succinic acid to motor gasoline to prevent ice formation on the carburetor. Examples of amine reagents are: primary tertiary dividing and thereby suspending or stopping butylamine, primary tert-hexylamine, n-hexylamine, of the engine during the warm-up period, n-octylamine, n-octenylamine, primary tert-octylist Subject of the German patent 1 086 942. The amine, 2-ethylhexylamine, primary tert-decylamine,

5 6

n-decylamine, primary tert-dodecylamine, n-undecyl- trate ions are used as others to be effective amine, dodecenylamine, dodecadienylamine, tetra- be. In most cases where desired decylamine, primary tert-tetradecylamine, primary will get all three beneficial properties, tert-octadecylamine, hexadecylamine, octadecenyl- namely the inhibition of sediment formation, the amine, octadecadienylamine, primary tert-eicosylamine, 5 reduction of the clogging of the sieve and the Verinn-eicosylamine, primary tert-tetracosylamine, penta-modification of the roasting of ferrous metal surfaces cosylamine and primary tert-triacontylamine. Additive concentrations between about 2.85 and The amine reagents can be used on different 57 g per hectolitre of oil. However, it cannot Way to be produced by known methods. always be desired, all three of the above mentioned results Process to realize the primary io nisse. In such cases where you can only Tertiary alkylamines are in the Journal of Organic Chemistry, one or two results you may wish to receive Vol. 20, pp. 295fF. (1955). Mixtures of lower concentrations can be used. If it such amines can be obtained from a polyolefin fraction e.g. B. is desired, only the rusting under dynamic (z. B. polypropylene and polybutylene cuts) there- conditions such. B. in a pipeline to verdurch It has been found that they are so low in acidity and water to the appropriate alcohol concentrations such as 5 parts per million, i.e. H. about 0.3 g hydrated, the alcohol with dry chlorinated water additive is effective per hectolitre of oil. Hence the converts substance into allyl chloride and finally the amount of amic acid or amine salt of amic acid, Chloride condensed with ammonia under pressure to which the distillate fuel is added to a a mixture of tertiary alkyl primary amines to achieve beneficial results, in general produce. between about 0.3 and 57 g per hectolitre of oil. Preferred as fuel oils are hydrocarbon fractions, this amount is about 3 to 57 g per hectolitre nen that have an initial boiling point of at least about oil.

38 ⁰ C and a final boiling point of no more than desired, the fuel oil compositions can be about 400 ⁰ C and the substantially continuous compositions use other additives for the purpose of boiling over their distillation range. Achieving other results included. Such fuel oils are usually known as distillate, for example foam inhibitors or the fuel oils. It should be noted, however, that ignition and burning property enhancers do not have this designation on straight run distillate. Examples of such additives are limited to fractions. The distillate fuel oils 30 are silicones, dinitropropane, amyl nitrate, or metal cans made from straight-run distillate fuel oils, cata- sulfonates.

Lytically or thermally cracked (including the following specific examples serve the hydrocracked) distillate fuel oils or Art. Distillate products exist. Such fuel oils
can also be treated according to known technical methods such as acid or alkali treatment, hydrogenation, amic acids and salts, solvent refining, clay treatment, etc. 40 The amine used in the specific examples

The distillate fuel oils are characterized by their reagents are mixtures of pure amines, relatively low viscosities and pour points. "Amine A" is a mixture of primary amines. The main property which characterizes the hydrocarbons in which one carbon atom of a tert-butyl group is bonded to the amino (- NH 4 group, and net, however, is the boiling range. As above, the 12 to 15 carbon atoms per amine molecule and, optionally, this range is between about 38 and containing 12 carbon atoms per molecule. 400 ⁰ C. The boiling range of each individual fuel containing this mixture about 85 weight percent, however, the oil covers obviously a narrower boiling primary tert.-dodecylamine, about 10 weight percent range, which nonetheless falls within the primary tertiary pentadecylamine and relative limits given above.Each fuel oil boils 50 small amounts, ie less than about 5 weight percent substantially continuously above its boiling percent, of amines of less than 12 or more as range. 15 carbon atoms.

Of the fuel oils, in particular, the »amine B« is a mixture of primary tertiary

Fuel oils No. 1, 2 and 3, which are used for heating purposes and alkyl amines containing 18 to 24 carbon atoms each

are used as diesel oils, and fuels 55 molecules and an average of 20 carbon atoms each

for jet engines into consideration. The fuel oils for molecule. It has a tertiary carbon atom that

Household uses are generally the same as those attached to the -NH ₂ group, and include about

Regulations according to ASTM D-396-48T. Regulation for 40 percent by weight primary tert-octadecylamine,

Diesel fuels are given in ASTM D-975-48T. about 30 percent by weight primary tert-eicosylamine,

Typical jet propellant fuels are about 15 percent by weight primary tert-docosylamine in the pre-60

document MIL-F-5624B. about 10 weight percent tertiary tetracosyl primary amine

The amount of the amic acid or amine salt of and a minor amount, less than 5 percent by weight,

Amic acid existing additive, which is the distillate to other amines, such as primary tert-triacontyl-

lat fuel oil is added according to the invention, amine.

depends of course on the intended use and 65 "amine C", "amine D" and "amine E" are mixtures

the particular chosen amic acid or that of normal aliphatic primary amines with the

chose salt because it does not contain all of the compositions given in Table I in terms of their activity

are equivalent. Some need to be in larger concentrations.

Table I.

Normal amine

Hexyl

Octyl

Decyl

Dodecyl

Tetradecyl

Hexadecyl

Octadecyl

Octadecenyl ..
Octadecadienyl

Amine C Amin D 3 90 7th - - 10 - 10 - 35 - 45

Amine E.

2 24 28 46

example 1

A mixture of 100 g (0.5 mol) of "amine A", 50 g (0.5 mol) of succinic anhydride and 50 g of xylene (as a diluent) was heated with stirring for 3 hours at 80 to 85 ° C to remove the succinamic acid to build. The reaction product was clear and liquid at room temperature.

Example 2

A mixture of 150 g (0.5 mol) of "amine D", 50 g (0.5 mol) of succinic anhydride and 100 g Xylene (as a diluent) was heated at 80 ° C with stirring for 3 hours to give a succinamic acid to build.

Example 3

A mixture of 79 grams (0.615 moles) of "Amine C", 61.5 grams (0.615 moles) of succinic anhydride, and 140 grams Xylene (as a diluent) was stirred at 90 ° C for 3 hours to form a succinamic acid heated.

Example 4

A mixture of 100 g (0.5 mol) of "amine A", 49 g (0.5 mol) of maleic anhydride and 75 g of xylene (as a diluent) was heated for 2 hours at 65 to 75 ⁰ C under stirring to a maleamic acid ( Maleic acid monoamide). 100 g (0.33 mol) of "amine D" were added to form the amine salt. The material was then stirred for a further 2 hours at 9O ⁰ C.

Example 8

A mixture of 100 g (0.5 mol) of "AminA", 50 g (0.5 mol) of succinic anhydride and 100 g Xylene (as a diluent) was stirred for 2 hours at 75 ° C to form a succinamic acid. At room temperature, 64.5 g (0.5 mol) of "amine C" was added to form the amine salt. The product was stirred at 65 ° C. for 2 hours.

Example 9

A mixture of 50g (0.25 mol) of »AminA«, 24.5 g (0.25 mol) of maleic anhydride and 62 g of xylene (as a diluent) was added for 1 hour Stirred at 75 ° C to form a maleic acid. The maleamic acid was added at room temperature

zo 50 g (0.25 mol) of "amine A" to form the amine salt admitted. The material was then stirred at 75 ° C for 2 hours.

Example 10

A mixture of 49 g (0.5 mol) of maleic anhydride and 118 g (0.5 mol) of a technical Quality of the "amine A" was stirred for 2 hours at 81 ° C. to form the maleamic acid. That Room temperature was viscous, paraffinic oil (100 SSU at

Product that at
was with 167 g
38 ° C).

Example 11

A mixture of 303 g (1.0 mol) of "amine B", 98 g (1.0 mol) of maleic anhydride and 200 g of xylene (as a diluent) was stirred for 2 hours at 90 ° C to form the maleic acid.

Example 12

A mixture of 175 grams (0.57 moles) of "Amine B", 57 grams (0.57 moles) of succinic anhydride, and 100 grams Xylene (as a diluent) was stirred for 2 hours at 90 ° C to form the succinamic acid.

45

Example 5

A mixture of 95 g (V ₃ moles) of "amine E" 33 g (V ₃ moles) of maleic anhydride and 128 g of xylene (as a diluent) was heated at 75 to 85 ⁰ C under stirring for 3 hours, to form a maleamic acid.

Example 6

A mixture of 50 g (0.25 mol) of "amine A", 25 g (0.25 mol) of succinic anhydride and 67 g of xylene (as a diluent) was IV ₂ hours at 85 ⁰ C stirred to form a succinamic acid. To the succinamic acid was added 50 g (0.25 mol) of "amine A" at room temperature to form the amine salt (monosalt). The product was then ^{stirred at 85 to 90 °} C. for a further IV for ₂ hours.

Example 7

A mixture of 67 g (0.33 mol) of "amine A", 33 g (0.33 mol) of succinic anhydride and 100 g of petroleum (boiling range 173-27 Γ C) as a diluent was heated with stirring for 2 hours at 9O ⁰ C, to form a succinamic acid. At room temperature

Example 13

A mixture of 100 g (0.5 mol) of "amine A" and 50 g (0.5 mole) of succinic anhydride was stirred for 2 hours at 90 ⁰ C, to form the succinamic acid. 151 g (0.5 mol) of "amine B" were added to this acid to form the amine salt. The material was stirred at 95 ^° C. for _{2 hours.}

55

60 Sediment formation

The test which is used to determine the sedimentation properties of the fuel oils, the storage test at 43 ⁰ C. This test is 500 cc sample of the held one in a Konvexionsofen at 43 ⁰ C for a period of 12 weeks under test fuel oil. Then the sample is taken out of the oven and allowed to cool. The cooled sample is filtered through a tared asbestos filter (Gooch cross filter) to remove insoluble material. The weight of this material in milligrams is reported as the amount of sediment. A sample of the non-inhibited base oil (control) is examined together with the fuel oil mixture to be tested. The effectiveness of a burning

Substance oil, which contains an inhibitor, is thereby determined that the weight of the sediment formed in the inhibited oil is compared with that which is formed in the uninhibited oil, compares.

Example 14

Additives as described in Examples 1 to 13 were added to a test fuel oil mixed in, and the mixtures were sent to the warehouse

subjected to test at 43 ° C. The test results that allow a comparison of the inhibited oils and the not represent inhibited oils are given in Table II. The test fuel oil consisted of a mixture 60% distillate oil obtained from a continuous catalytic cracking operation and 40% straight-run distillate oil. It had a boiling range of about 160 to 338 ° C and was a typical fuel oil No. 2.

Table II storage test at 43 ⁰ C - 12 weeks

example Acid anhydride Inhibitor
Acid amine ¹ Salt amine ² j f _ r Concentration of
Inhibitors
g / hl sediment
mg / 1 ! { control
Amber- A. { { 0
28.5 24
11 ² { control
Amber- D. { { 0
14.3 56
44 4 { control
Malein- A. { 0
28.5 24
10 5 y control
Malein- E. f
^A I 0
28.5 60
18th 6 { control
Amber- A. D. 0
14.3 24
3 7th Amber- A. 28.5 10 " 1 control
Malein- A. 0
28.5 150
54 10 { control
Malein- A. 0
28.5 OO OO 11 y control
Malein- B. 0
28.5 49
17th ₁₂ { Control ³
Amber- B. 0
7.15 VO CN 13 { control
Amber- A. 0 -

*) Amine, combined with acid anhydride to form the amic acid.

² ) Amine used to form the amic acid salt.

³ ) Hydro refined fuels)].

Clogged sieve

The anti-clogging properties of a fuel oil are determined as follows:

The test is performed using a Sundstrand V3 that is used to feed a burner with domestic fuel oil. or -Sl pump with a self-supporting Monel metal sieve with a mesh size of 0.149mm carried out. About 0.05 weight percent of naturally formed fuel oil sediment fuel oil, water, dirt, rust and organic sludge become 10 1 of the fuel oil mixed. The pump circulates this mixture through the sieve for 6 hours. then the sludge precipitate on the sieve is washed out with normal pentane and tared through a Gooch cross filter nitrided. After drying, the material is in the filter with a 50:50 (vol.) Acetone-methanol mixture washed. All of the organic sediment is obtained by evaporating the pentane and the acetone-methanol filtrates. Drying and weighing the Gooch cross filter gives the amount of inorganic sediment. the The sum of the organic and inorganic precipitates obtained on the sieve can be expressed in milligrams specified or converted into the percentage of clogging of the sieve.

Example 15

Using the test fuel oil described in Example 14, mixtures of the Additives according to Examples 1 to 13 prepared in this oil. Each mixture was as above Subject to the sieve clogging test described. The test results are shown in Table III.

309 599/282

Table III

Additive concentration
g / hl Clogged sieve
° / o None
Example 1 ........
Example 2
Example 4
Example 5
Example 6
Example 7
Example 8
Example 9
Example 10
Example 11
Example 12
Example 13 0
28.5
28.5
28.5
28.5
14.3
28.5
28.5
28.5
28.5
7.15
7.15
7.15 100
8th
5
83
6th
21
0
2
43
44
3
12th
5

Table IV
ASTM rust test

Roast

Two methods were used to test the anti-rust properties of fuel oils.

One of the tests used was ASTM D-665 Rust Test is performed, the 48 hours at 27 ⁰ C using distilled water. This is a dynamic test that shows the ability to prevent rusting of ferrous metal surfaces in pipelines or pipes.

The other test is a static rust test that creates conditions similar to those used in storage tanks, such as: B. in a domestic heating oil storage tank. In this test, a strip of sandblower treated steel plate 0.4-0.5 mm thick is placed in a clear quartz bottle. The length of the strip is sufficient to extend from the bottom of the bottle into the neck of the bottle without interfering with the cap. 100 ecm of synthetic sea water, which is adjusted to a pa value of 5 (ASTM test D-665), and 750 ecm of test oil are introduced into the bottle. The bottle is tightly closed with a cap, shaken vigorously for 1 minute and then left to stand still at 27 ^° C. for 21 days. At the end of this time, the amount of rust that appears on the surface of the plate immersed in the water is used as a measure of the effectiveness of the fuel oil in inhibiting roasting in storage vessels. Preferably, generally not more than 5% of the surface should be rusted. This test is much more severe than the ASTM rust test. Many additive compositions that meet the ASTM test fail the static test. On the other hand, materials that successfully pass the static test always pass the ASTM test.

Example 16

Mixtures of additives as described in Examples 1 to 13 in the fuel oil according to Example 14 were subjected to the ASTM rust test D-665. The values obtained are shown in Table IV.

5
Additive concentration
Parts
per million Result None
IO
example 1
Example 2
Example 3
15 Example 4
Example 5
Example 6
Example 7
20th
Example 8
Example 9
Example 11
25 Example 12
Example 13 0
5
10
25th
100
25th
10
5
10
100
10 not fulfilled
Fulfills
Fulfills
Fulfills
Fulfills
Fulfills
Fulfills
Fulfills
Fulfills
Fulfills
Fulfills

Example 17

The additives described in Examples 1, 2, 3, 5, 6, 7, 8 and 13 were each in partial amounts of the fuel oil according to Example 14 mixed. The mixes were static Subject to rust test. The values obtained are given in Table V.

Table V
Static rust test

Additive concentration
g / hl rust
% 45
None
example 1
Example 2
50 Example 3
Example 5
Example 6
Example 7
Example 8
Example 13 0
7.15
7.15
14.3
2.85
14.3
7.15
14.3
21.5 100
0
0
0
50
5
3
0
30th

It can be seen from the values given in Tables II to V that the maleamic acids and the Succinamic acids according to the invention and their amine salts (ammonium salts) are very effective agents to reduce the formation of sediments and clogging of the sieve and to inhibit the roasting of Ferrous metal surfaces are under static and dynamic conditions. As expected, sway the results according to the particular materials used. To any given

To achieve improvement, many of the additives can be used in relatively small amounts, z. B. to prevent dynamic rust. On the other hand, if you have all of the aforementioned cheap Desires to obtain results, this can be done at the practical additive concentration of 14.3 up to 28.5 g per hectolitre of fuel oil can be realized.

For the lubricants, the same amic acids and their amine salts can be used as in the fuel oils, especially highly refined mineral lubricating oils such as steam turbine oils, To give anti-rust properties. The amount of amic acid or amine salt added to the lubricating oil is added, varies between about 0.001 and 10%> based on the weight of the oil. According to In a preferred embodiment, amounts are between about 0.05 and 1.0 percent by weight lying, used. Other substances can be added to the lubricating oil to give it other properties To give. For example, antioxidants, pour point depressants, viscosity index improvers and High pressure media can be used.

The following examples serve to illustrate the anti-rust lubricants according to the invention as they are obtained with mineral oils, and illustrating their effectiveness.

Example 18

A mixture of 33.4 g (0.33 mol) of succinic anhydride, 66.7 g (0.33 mol) of "amine A" and 200 g of paraffinic oil (100 SSU at 38 ^° C.) as a diluent was taken at 90 ^° C. Stir heated for 3 hours to form an oil solution of the amic acid. 100 g (0.33 mol) of "amine B" were added to this mixture. This mixture was stirred at 90 ° C. for 1 hour to form the "amine-B" salt of the "amine-A" succinamic acid.

40

Example 19

A mixture of 152 g (0.5 mole) of "Amine B" and It can be seen that the amic acids and their

50 g (0.5 mole) of succinic anhydride was 2 STUN amine salts are effective, stirred for lubricating oils in areas at 110 ⁰ C to the "amine-B" -Succmamid- 45 waiting of seawater to provide anti-rust properties of acid to form. This is how the mineral oil compositions are

very effective for severe conditions, e.g. B. in example 20 lubrication of ship turbines.

The blends were made to ASTM-Rosttes D-665-44T using synthetic seawater subject. The composition of each blend and the test results are in Table VI reproduced.

The test method used to distinguish the rust properties of lubricating oil blends was ASTM test D-665-44T for the determination of "rust preventive properties of steam turbine oils in the presence of water" in which synthetic seawater is used. The synthetic sea water contained 25 g sodium chloride, 11 g magnesium chloride hexahydrate, 4 g sodium sulfate and 1.2 g calcium chloride per liter. In this test a cylindrical polished steel piece is hung and 30 minutes in 300 cc of submerged under test oil at 6O ⁰ C. 30 cc of synthetic sea water is added and the mixture is stirred at 1000 rpm. After 48 hours, the piece of steel is removed and examined for the appearance of rust on the part of the piece of steel that was hanging in the oil. To pass this test, the test piece must be completely rust free.

Table VI

Conc Base oil ASTM rust test Additive tration
Weight percent X not fulfilled None X Fulfills example 1 0.05 X Fulfills Example 18 0.01 Y not fulfilled None Y Fulfills example 1 0.05 Y Fulfills Example 19 0.05 Y Fulfills Example 20 0.05

A mixture of 152 g (0.5 mol) of "amine B" and 49 g (0.5 mol) of maleic anhydride was used for 2 hours stirred at 115 ° C to form the "amine-B" maleamic acid.

Example 21

55

Four mineral oil blends were prepared. Each mixture contained a small amount of one of the additives described in Examples 1, 18, 19 and 20. Two base oils were used. The oil X consisted of a solvent refined mineral oil with a specific gravity of 0.8708 at 15 ⁰ C and a Saybolt Universal viscosity of 150 seconds at 38 ° C. The oil Y consisted of a solvent refined Mid-Continent-oil with a specific gravity of 0.8816 at 15 ° C and a Saybolt Universal viscosity of 415 seconds at 38 ⁰ C.

Both are typical steam turbine lubricating oils.

Claims (2)

PATENT CLAIMS: 1. Use of amic acids of the formula RHN - C - R '- COOH ü ο in which R 'is either - CH ₂ - CH ₂ - or - CH = CH - and R is a monovalent alkyl radical having 4 to 30 carbon atoms, e.g. B. a tertiary alkyl radical with 12 to 30 carbon atoms, in which a tertiary carbon atom is bonded directly to the nitrogen atom, or their salts with aliphatic primary amines RNH ₂ , in which R has the meaning given above, as additives to fuel 15 16 and lubricating oils, when used about 0.001 to 10 weight percent, preferably as a lubricating oil additive, the remainder R is only 0.05 to 1 percent by weight above. for example has given meaning. 2. Use of amic acids according to claim 1 Considered publications: in an amount of 0.3 to 57 g per hectolitre 5 U.S. Patents Nos. 2,582,412, 2,604,451, Fuel, preferably at least 2.85 g per 2 540 800, 2 654 708, 2 654 709, 2 625 511, 2 629 649, Hectoliters of fuel, or 2,490,744 for lubricating oils. © 309 599/282 5.63