EP0055355A1 - Distillats de pétrole à fonctionnement amélioré à basse température - Google Patents

Distillats de pétrole à fonctionnement amélioré à basse température Download PDF

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Publication number
EP0055355A1
EP0055355A1 EP81108840A EP81108840A EP0055355A1 EP 0055355 A1 EP0055355 A1 EP 0055355A1 EP 81108840 A EP81108840 A EP 81108840A EP 81108840 A EP81108840 A EP 81108840A EP 0055355 A1 EP0055355 A1 EP 0055355A1
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EP
European Patent Office
Prior art keywords
acid
oil
fatty acid
paraffin
pour point
Prior art date
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Granted
Application number
EP81108840A
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German (de)
English (en)
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EP0055355B1 (fr
Inventor
Hans-Henning Dr. Vogel
Knut Dr. Oppenlaender
Rainer Dr. Strickler
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BASF SE
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BASF SE
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Publication date
Application filed by BASF SE filed Critical BASF SE
Publication of EP0055355A1 publication Critical patent/EP0055355A1/fr
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Publication of EP0055355B1 publication Critical patent/EP0055355B1/fr
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    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
    • C10L1/224—Amides; Imides carboxylic acid amides, imides
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/143—Organic compounds mixtures of organic macromolecular compounds with organic non-macromolecular compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/192—Macromolecular compounds
    • C10L1/195—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • C10L1/196—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and a carboxyl group or salts, anhydrides or esters thereof homo- or copolymers of compounds having one or more unsaturated aliphatic radicals each having one carbon bond to carbon double bond, and at least one being terminated by a carboxyl radical or of salts, anhydrides or esters thereof
    • C10L1/1963—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and a carboxyl group or salts, anhydrides or esters thereof homo- or copolymers of compounds having one or more unsaturated aliphatic radicals each having one carbon bond to carbon double bond, and at least one being terminated by a carboxyl radical or of salts, anhydrides or esters thereof mono-carboxylic
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/192—Macromolecular compounds
    • C10L1/195—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • C10L1/197—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and an acyloxy group of a saturated carboxylic or carbonic acid
    • C10L1/1973—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and an acyloxy group of a saturated carboxylic or carbonic acid mono-carboxylic

Definitions

  • Gas oils for example, which occur in a boiling range between 130 and 420 ° C, can contain 75 - 85% of saturated hydrocarbons, of which in turn 20 - 35% can be present as n-alkanes (paraffins).
  • the paraffins essentially determine the cold properties of a gas oil.
  • fractions in the interior of the tank, which are composed differently and differ in their physical and application properties.
  • sensitive disruptions in pipelines, pre-filters, combustion units or fuel filters or fuel metering devices can occur even at higher outside temperatures.
  • the temperature at which this phenomenon is first observed is the Clöud Point.
  • the temperature at which the sample is still flowing is called the pour point and the temperature at which it solidifies is the pour point.
  • the filterability is also used to assess the cold behavior of an oil.
  • the filterability under standardized cooling conditions is measured in the so-called CFPP test ("Cold Filter Plugging Point", DIN).
  • CFPP test Cold Filter Plugging Point
  • DIN Cold Filter Plugging Point
  • additives should achieve better filterability and pumpability.
  • Such additives act as crystal nucleating agents and growth regulators for paraffin crystals. They keep the wax crystals small and thus lower the CFPP and pour point.
  • the object of the invention is to provide products which are capable of precipitating in the cold from petroleum distillates n-paraffin finkristalle or evenly distributed to keep. to prevent their sedimentation. It does not come after so much important to improve the above-mentioned Kennzah- len, but to form a homogeneous crystal dispersion.
  • oil-soluble acid amides of oligo- 11 and polyamines with long-chain fatty acids or fatty acid-like substances are able to disperse wax crystals in petroleum distillates and prevent them from sinking: if oligo- or polyamines, for example of the formula correspond (where X is an ethylene, propylene or isopropylene radical and m as well as n are between 0 and 500, preferably between 2 and 50) are reacted with a fatty acid with 8 or more carbon atoms, at least partially converted Acid amides, which are oil-soluble and can be used for the purposes of the invention.
  • Such amides can also be obtained by condensing oligo- or polyamines with suitable fatty acid esters, such as e.g. (Saturated or unsaturated) half esters of saturated or unsaturated dicarboxylic acids with long-chain alcohols with elimination of water.
  • suitable fatty acid esters such as e.g. (Saturated or unsaturated) half esters of saturated or unsaturated dicarboxylic acids with long-chain alcohols with elimination of water.
  • the condensation can be carried out without auxiliary agents, but also in solvents such as Toluene or xylene, which allow an azeotropic removal of the water formed in the reaction.
  • the condensation proceeds. between 80 and 220 ° C, preferably between 120 and 190 ° C. Up to 1 mol of carboxylic acid can be reacted per reactive equivalent: the conversion ratio of the reactive amino groups is usually 0.2 to 1.
  • acid amides can also be prepared with the aid of carboxylic acid derivatives such as carboxylic acid esters, carboxylic acid anhydrides or carboxylic acid chlorides.
  • carboxylic acid derivatives such as carboxylic acid esters, carboxylic acid anhydrides or carboxylic acid chlorides.
  • the course of the reaction can be followed simply by determining the amine number and the acid number, but also by means of the amount of water which is distilled off.
  • the reaction does not need to be driven to full implementation. This is advantageous, for example, in order to avoid thermal decomposition in the case of higher molecular weight polyamines.
  • Suitable polyamines which can be acylated are, for example, diethylenetriamine, triethylenetetramine, dipropylenetriamine, tripropylenetetramine, tetrapropylenepentamine and polyethyleneimines with an average degree of polymerization of e.g. 10, 35, 50 or 100 as well as polyamines which are obtained by reacting oligoamines with acrylonitrile and subsequent hydrogenation, i.e. Chain extension were obtained such as N, N'-bis (3-aminopropyl) ethylenediamine.
  • Suitable fatty acids are pure fatty acids and particularly technically customary fatty acid mixtures which contain stearic acid, palmitic acid, lauric acid, oleic acid, linoleic acid and / or linolenic acid.
  • the natural fatty acid mixtures such as e.g. Tallow fatty acid, coconut oil fatty acid, trans fatty acid, coconut palm kernel oil fatty acid, soybean oil fatty acid, rapeseed oil fatty acid, peanut oil fatty acid, palm oil fatty acid, etc., which contain oleic acid and palmitic acid as main components.
  • Fatty acid-analogous compounds can also be used; Monoesters of long-chain alcohols of dicarboxylic acids, such as, for example, tallow fatty alcohol maleic acid semi-esters or tallow fatty alcohol succinic acid half-esters or corresponding Glutaric or adipic acid half esters are such technically common substances.
  • the products according to the invention can be added to the petroleum distillate as the sole additive. However, the addition is preferred together with commercially available flow improvers. These are mostly polymers or copolymers based on ethylene and unsaturated compounds or chlorinated polyethylene waxes. The known commercially available flow improvers based on ethylene / vinyl acetate or ethylene / alkyl acrylate may be mentioned as an example.
  • the paraffin dispersants according to the invention can be used in pure form, but also as a solution in suitable solvents, e.g. Dimethylformamide, higher alcohols, ethyl acetate, butyl acetate, benzene, but preferably in toluene, xylene or other hydrocarbons.
  • the product from synthesis example A 25 was used as a paraffin dispersant.
  • the 3 liter measuring cylinder shown on the left in FIG. 1 served as the test apparatus.
  • heating oils Commercially available heating oils, extra light, West German refinery goods were tested in the measuring cylinders.
  • 3 liters of heating oil were mixed with commercially available flow improvers or additionally with the paraffin dispersants according to the invention to be tested and stored in a refrigerator at temperatures above the pour point.
  • samples of approx. 50 to 80 ml were taken from 5 side taps at different heights.
  • the flow improver contains as active substance e.g. an ethylene / vinyl acetate copolymer.
  • this represents a sensible distribution of the sampling points over the entire liquid volume.
  • the evaluation of the experiment is shown in the following FIG. 2.
  • the 6 sample fractions are plotted on the abscissa and the content of n-paraffins (upper part) and the temperatures for the critical parameters CFPP, cloud point, and pour point are plotted on the ordinate.
  • fractions 1 and 2 contain the highest proportion of n-paraffins at approximately 11.5%.
  • Consrespondingly high in fractions 1 and 2 is Cloudpoint and CFPP with 10 and 11 ° C, respectively.
  • Fraction 3 in Figure 1 already outside the paraffin separation, has a significantly lower content of n-paraffins (5.2%) than Fraction-1 and 2 and accordingly good cold properties, namely Cloudpoint and CFPP (-14 ° C). The same behavior applies to fractions 4, 5 and 6.
  • Examples 2 and 3 are based on analogous experiments with a heating oil which, in addition to the flow improvers mentioned above, each contained 0.05% by weight of compound A 14; the storage temperature was -15 ° C in Example 2 and -10 ° C in Example 3.
  • the key figures found are listed in Table 2 at the end of the description together with the comparative test example 1 and a further series of tests.
  • the 3 liter measuring cylinders shown in FIG. 1b served as test equipment. 6 melted capillary tubes, which had been melted down and ended at different heights - each at the point where the test taps of the device according to FIG. 19 are located - were immersed in the heating oil. The capillaries were bent over at the upper end and closed with a hose that was put over them using a pinch valve. Sampling was carried out using 50 ml pipettes at the tube connections of the capillaries.
  • the property profile is shown in Fig. 6. It can be seen that due to the paraffin distribution in the test apparatus, fractions 1, 2 and 3 with 11.2 and 10.3 as well as 9.4% have the highest content of n-paraffins.
  • the cloud point is correspondingly high at 5 or 3.5 ° C and the CFPP at 4, -1 or 0 ° C.
  • Fractions 4 to 6 were drawn above the paraffin deposition and show significantly better, i.e. lower indicators for the cold behavior.
  • the dependence of the pour point on the tapping point is similar to the method according to Fig. La. In the separated paraffin sediment (fractions 1 to 3), the pour point is the lowest at -27 to -30 ° C due to the failed flow improver. A higher pour point of -24 to -21 ° C. is measured in the "paraffin-poor" fractions 4 to 6, which contain fewer flow improvers.
  • the oil was stored for 72 hours at -15 ° C and then showed an even turbidity on the outside.

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Liquid Carbonaceous Fuels (AREA)
  • Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
  • Fats And Perfumes (AREA)
  • Lubricants (AREA)
EP81108840A 1980-12-31 1981-10-24 Distillats de pétrole à fonctionnement amélioré à basse température Expired EP0055355B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3049553 1980-12-31
DE19803049553 DE3049553A1 (de) 1980-12-31 1980-12-31 Erdoeldestillate mit verbessertem kaelteverhalten

Publications (2)

Publication Number Publication Date
EP0055355A1 true EP0055355A1 (fr) 1982-07-07
EP0055355B1 EP0055355B1 (fr) 1985-01-23

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ID=6120586

Family Applications (1)

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EP81108840A Expired EP0055355B1 (fr) 1980-12-31 1981-10-24 Distillats de pétrole à fonctionnement amélioré à basse température

Country Status (5)

Country Link
EP (1) EP0055355B1 (fr)
DE (2) DE3049553A1 (fr)
DK (1) DK569881A (fr)
FI (1) FI814025A7 (fr)
NO (1) NO155779C (fr)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0081744A3 (en) * 1981-12-15 1983-11-16 Basf Aktiengesellschaft Fuel additives for internal-combustion engines
EP0398101A1 (fr) * 1989-05-19 1990-11-22 BASF Aktiengesellschaft Produits de réaction d'acides aminoalkylène-polycarboxyliques avec des amines secondaires ainsi que distillats moyens de pétrole brut les contenant
WO1994006894A1 (fr) * 1992-09-22 1994-03-31 Exxon Chemical Patents Inc. Additifs pour liquides organiques
WO1995003377A1 (fr) * 1993-07-22 1995-02-02 Exxon Chemical Patents Inc. Additifs et compositons de combustibles
WO1998021446A1 (fr) * 1996-11-14 1998-05-22 Bp Exploration Operating Company Limited Inhibiteurs et leurs applications dans des huiles
GB2334258A (en) * 1996-11-14 1999-08-18 Bp Exploration Operating Inhibitors and their uses in oils
WO2007147753A3 (fr) * 2006-06-22 2008-04-17 Basf Ag Mélange constitué de composés d'azote polaires oléosolubles et d'amides d'acides en tant que dispersant de paraffine pour des carburants
EP2196520A1 (fr) * 2008-12-09 2010-06-16 Infineum International Limited Procédé d'amélioration de compositions d'huile
US20240400920A1 (en) * 2021-10-14 2024-12-05 Chevron U.S.A. Inc. Polyamide fuel additives

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1123818A (fr) * 1955-03-19 1956-09-28 Exxon Standard Sa Compositions antirouille
US2852467A (en) * 1953-12-28 1958-09-16 Exxon Research Engineering Co Lubricating oil additive
FR1219236A (fr) * 1957-10-22 1960-05-16 Exxon Research Engineering Co Agents pour la mise en suspension d'hydrocarbures paraffiniques normalement solides dans des liquides pétroliers
US3166387A (en) * 1961-07-17 1965-01-19 Standard Oil Co Ammonium carboxylate pour point depressants for fuel oil composition
DE2042683A1 (de) * 1969-09-15 1971-03-25 Esso Research and Engineering Co , Linden, NJ (V St A ) Heizolmischung
US3681038A (en) * 1970-03-09 1972-08-01 Universal Oil Prod Co Middle distillate
US3877888A (en) * 1970-03-09 1975-04-15 Universal Oil Prod Co Middle distillate

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2852467A (en) * 1953-12-28 1958-09-16 Exxon Research Engineering Co Lubricating oil additive
FR1123818A (fr) * 1955-03-19 1956-09-28 Exxon Standard Sa Compositions antirouille
DE1188751B (de) * 1955-03-19 1965-03-11 Exxon Standard Sa Korrosionsschutzgemische
FR1219236A (fr) * 1957-10-22 1960-05-16 Exxon Research Engineering Co Agents pour la mise en suspension d'hydrocarbures paraffiniques normalement solides dans des liquides pétroliers
US3166387A (en) * 1961-07-17 1965-01-19 Standard Oil Co Ammonium carboxylate pour point depressants for fuel oil composition
DE2042683A1 (de) * 1969-09-15 1971-03-25 Esso Research and Engineering Co , Linden, NJ (V St A ) Heizolmischung
US3681038A (en) * 1970-03-09 1972-08-01 Universal Oil Prod Co Middle distillate
US3877888A (en) * 1970-03-09 1975-04-15 Universal Oil Prod Co Middle distillate

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0081744A3 (en) * 1981-12-15 1983-11-16 Basf Aktiengesellschaft Fuel additives for internal-combustion engines
EP0398101A1 (fr) * 1989-05-19 1990-11-22 BASF Aktiengesellschaft Produits de réaction d'acides aminoalkylène-polycarboxyliques avec des amines secondaires ainsi que distillats moyens de pétrole brut les contenant
WO1994006894A1 (fr) * 1992-09-22 1994-03-31 Exxon Chemical Patents Inc. Additifs pour liquides organiques
WO1995003377A1 (fr) * 1993-07-22 1995-02-02 Exxon Chemical Patents Inc. Additifs et compositons de combustibles
WO1998021446A1 (fr) * 1996-11-14 1998-05-22 Bp Exploration Operating Company Limited Inhibiteurs et leurs applications dans des huiles
GB2334258A (en) * 1996-11-14 1999-08-18 Bp Exploration Operating Inhibitors and their uses in oils
GB2334258B (en) * 1996-11-14 2001-05-16 Bp Exploration Operating Inhibitors and their uses in oils
WO2007147753A3 (fr) * 2006-06-22 2008-04-17 Basf Ag Mélange constitué de composés d'azote polaires oléosolubles et d'amides d'acides en tant que dispersant de paraffine pour des carburants
AU2007263066B2 (en) * 2006-06-22 2011-04-28 Basf Se Mixture from polar oil-soluble nitrogen compounds and acid amides as paraffin dispersant for fuels
US8187345B2 (en) 2006-06-22 2012-05-29 Basf Se Mixture from polar oil-soluble nitrogen compounds and acid amides as paraffin dispersant for fuels
EP2196520A1 (fr) * 2008-12-09 2010-06-16 Infineum International Limited Procédé d'amélioration de compositions d'huile
US20240400920A1 (en) * 2021-10-14 2024-12-05 Chevron U.S.A. Inc. Polyamide fuel additives

Also Published As

Publication number Publication date
DE3168527D1 (en) 1985-03-07
NO155779C (no) 1987-05-27
DE3049553A1 (de) 1982-07-29
FI814025L (fi) 1982-07-01
FI814025A7 (fi) 1982-07-01
NO814341L (no) 1982-07-01
DK569881A (da) 1982-07-01
NO155779B (no) 1987-02-16
EP0055355B1 (fr) 1985-01-23

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