CA1273201A - Additive to diesel engine fuel oil - Google Patents

Additive to diesel engine fuel oil

Info

Publication number
CA1273201A
CA1273201A CA000517494A CA517494A CA1273201A CA 1273201 A CA1273201 A CA 1273201A CA 000517494 A CA000517494 A CA 000517494A CA 517494 A CA517494 A CA 517494A CA 1273201 A CA1273201 A CA 1273201A
Authority
CA
Canada
Prior art keywords
additive
fuel oil
carbon atoms
diesel engine
weight
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
CA000517494A
Other languages
French (fr)
Inventor
Shigeru Okada
Hirochiko Hoshi
Keiichi Akimoto
Makoto Kato
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sanyo Chemical Industries Ltd
Toyota Motor Corp
Original Assignee
Sanyo Chemical Industries Ltd
Toyota Motor Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Sanyo Chemical Industries Ltd, Toyota Motor Corp filed Critical Sanyo Chemical Industries Ltd
Application granted granted Critical
Publication of CA1273201A publication Critical patent/CA1273201A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
    • C10L1/14Organic compounds
    • C10L1/143Organic compounds mixtures of organic macromolecular compounds with organic non-macromolecular compounds
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
    • C10L1/14Organic compounds
    • C10L1/18Organic compounds containing oxygen
    • C10L1/192Macromolecular compounds
    • C10L1/198Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
    • C10L1/14Organic compounds
    • C10L1/22Organic compounds containing nitrogen
    • C10L1/222Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
    • C10L1/2222(cyclo)aliphatic amines; polyamines (no macromolecular substituent 30C); quaternair ammonium compounds; carbamates
    • C10L1/2225(cyclo)aliphatic amines; polyamines (no macromolecular substituent 30C); quaternair ammonium compounds; carbamates hydroxy containing
    • FMECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
    • F02COMBUSTION ENGINES; HOT-GAS OR COMBUSTION-PRODUCT ENGINE PLANTS
    • F02BINTERNAL-COMBUSTION PISTON ENGINES; COMBUSTION ENGINES IN GENERAL
    • F02B3/00Engines characterised by air compression and subsequent fuel addition
    • F02B3/06Engines characterised by air compression and subsequent fuel addition with compression ignition

Landscapes

  • 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)
  • Solid Fuels And Fuel-Associated Substances (AREA)

Abstract

ABSTRACT OF THE DISCLOSURE
An additive for diesel engine fuel oil comprises an oxyalkylene derivative of an aliphatic amine such as N,N-dihydroxyethyldodecylamine, and a polyoxyalkylene glycol monoether such as polypropylene glycol mono-n-butyl ether.
The additive is added to the diesel engine fuel oil directly or dissolved in a solvent, and effectively cleans up deposits in the injector nozzles of a diesel engine, preventing the nozzles from clogging.

Description

~273;~(31 This invention relates to additives for diesel fuel oil.
Diesel fuel oil produces deposits in the injector nozzles of diesel engines when burnt, which may cause clog~ing of the injector nozzles. Hitherto, diesel fuel oil has only rarely been supplemented with an addi-tive, but the following prior art is known which discloses means for cl~aning diesel engines.
Japanese Patent Publication No. 20550 of 1966 proposed a method which adds alkylphenol and oil-soluble alkali or alkaline earth metal compounds to diesel fuel oil for decreasing black smoke produced in the exhaust gas when the diesel fuel oil is burnt. However, this method is not effective in preventing the formation of deposits in the injector nozzle of a diesel engine and the eventual clogging thereo~.
U.S. Patent No. 4,409,000 describes a method which enables an oxyalkylene compound of an amine to coexist with hydrocarbon-soluble carboxylic dispersants, such as an alkenylsuccineimide compound, by adding a volatile fuel oil such as gasoline in order to keep clean a carburetor.
The combination of these compounds, however, cannot prevent deposit in and clogging of the injector nozzle of a diesel engine.
It is an object of the present invention to provide an additive for diesel fuel oil which permits easy cleaning and removal of deposits in the injector nozzles of diesel engines.
According to the present invention, there is provided a diesel fuel oil additive comprising (A) an oxylakylene derivative of an amine having the general formula:
R -N ~ 1 ----.... (1) wherein Rl is an aliphatic hydrocarbon group having from 6 to 24 carbon atoms, Al is an alkylene group having ,,,~ ?"~
t . ~
, ~ ' ' ' ', ' ~ ' , ' ~, " ' ' ', ' ~ ' "', ' , , :
' , ' ' ' ' -127~;~o~

from 2 to 4 carbon atoms, Q and m are integers of 1 or more, with Q ~ m being a total of from 2 to lO; and ~B) a polyoxyalkylene glycol mono-ether having the general formula:
~3-o-~A2o ~ H ....................... (2) wherein R3 ls a hydrocarbon group having from 3 to 18 carbon atoms, A2 is an alkylene group having 3 or 4 carbon atoms and n is an integer of from 2 to 60.
This additive is added to the diesel fuel oil directly or dissolved in a solvent.
The aliphatic hydrocarbon group having from 6 to 24 carbon atoms and represented by Rl in general formula (l) includes linear or branched alkyl groups, such as hexyl, heptyl, octyl, nonyl, decyl, dodecyl, tridecyl, tetradecyl, hexadecyl, octadecyl, eicosyl, and docosyl, and alkenyl -~ groups, such as myristoleyl, palmitoleyl, oleyl, and linoleyl.
Among these, aliphatic hydrocarbons having from 8 to 20 carbon atoms are preferred with the decyl, dodecyl, tetradecyl, hexadecyl, octadecyl, and oleyl groups being particularly preferred. When Rl contains less than 5 or more than 25 carbon atoms, the effect on deposit removal is poor.
Suitable alkylene groups having from 2 to 4 carbon atoms and represented by Al include ethylene, propylene, butylene, and combinations of these groups, for example, ;; ethylene and propylene groups.
Each of Q and m represent an integer of 1 or more, and Q + m is from 2 to lO, preferably from 2 to 4.
- When the value of Q + m is smaller than 2 or larger than lO, the effect on deposit removal is poor.
Examples of oxyalkylene derivatives of an amine of formula (1) are N,N-dihydroxyethyldodecylamine, N,N-di-(hydroxyethoxyethyl) dodecylamine, N,N-dihydroxyethyl-~' tetradecylamine, N,N-dihydroxyethylstearylamine, and N,N-dihydroxyethyloleylamine.
In general formula (2) showing the polyoxyalkylene - ~ glycol monoether (8) used in the invention, the hydrocarbon '~, ;, " :: , - -. . ~ , .

, , .:- ` ` , :

1 ~ 73 ~1 group having from 3 to 18 carbon atoms and represented by R3 includes linear and branched alkyl groups such as propyl, butyl, amyl, hexyl~ octyl, decyl, dodecyl, tridecyl, tetradecyl, and hexadecyl, as well as phenyl groups having an alkyl substituent, for example, butylphenyl, hexylphenyl, octylphenyl, nonylphenyl, and dodecylphenyl groups. Among these, hydrocarbon groups having from 3 to 12 carbon atoms are preferred, and particularly preferred are propyl, butyl, amyl, hexyl, octyl, and decyl groups. When R3 has less than 3 or more than 18 carbon atoms, the effect on:deposit removal is poor.
The alkylene group having 3 or 4 carbon atoms and represented by A2 includes the propylene group and ~- 1,2-, 2,3-, 1,3-,;and 1,4- butylene groups, and combinations of these groups. Among these, propylene is preferred.
Symbol n is an integer of from 2 to 60, preferably from 4 to 45. When n is less than 2 or more than 60, the effect on deposit removal is poor.
Specific examples of compounds represented by 20 the general formula (2) are a mono-n-propyl ether of poly- -propylene glycol (average molecular weight: 600), a mono-n-butyl ether of polypropylene glycol (average molecular ~;weight: 1700), a mono-2-ethylhexyl ether of polypropylene glycol (average molecular weight: 14000), a mono-isodecyl ether of polypropylene glycol (average molecular weight:
1200), and a mono-nonylphenol ether of polypropylene glycol laverage molecular weight: 820).
The quantity by weight of additives (A) and (B) used according to the invention ~an be selected as desired, but the proportion of (A) is usually from 1 to 99% and that of (B) i5 from 99 to 1% based on the total weight of (A) plus (B); preferably from 10 to 99~ for (A) and from 90 to 10% for (B) The mixture of (A) and (B) can be diluted with i~a suitable solvent to facilitate handling. Diluents available ,,,, 35 include general fuel oil (such as kerosine, gas oil, and fuel oll), organic solvents readily miscible with petroleum fuel oil (e.g. aromatic solvents such as benzene, toluene, },~

.~, ~ . ~ . , - , -. , ~, -~ - - . . . . . .

1273, ~(31 and xylene and alcoholic solvents such as isopropanol, butanol, and butyl cellosolve), and mixtures of two or more of these solvents. Among these, toluene, xylene, propanol, and butanol are preferred. The quantity of the solvent to be used for dilution is usually from 0.1 to 100 parts by weight, preferably from 0.2 to 20 parts by weight based on one part by weight of the mixture of ~A) and (B).
The additives according to the invention can be mixed with various other additives (such as antioxidants, rust inhibitors, anticorrosive agents, fluidity improvers, draining agents, cetane improvers, color stabilizers, clari-fiers, detergent-dispersants, and bacteriostatic agents).
The diesel fuel oil used in conjunction with the additives of the invention is a petroleum product used for diesel engines, typified by kerosine (No. 1 and No.
2, JIS K-2203), gas oil (No. 1 to 3, Special No. 1 to 3, ~ JIS K-2204), and fuel oil A (JIS K-2205).
-~ The content of the additive according to the invention to be added to diesel fuel oil is normally from 0.001 to 5% by weight, preferably from 0.05 to 2% by weight based on the weight of the fuel oil.
There is no particular restriction on the method of addin~ the additive of the invention to diesel fuel oil. For example, the additive can be directly added to ~ diesel fuel oil or can be diluted with a general fuel oil ; or aromatic hydrocarbon solvent before addition.
The additive according to the invention is readily dissolved in diesel engine fuel oil and has no adverse effect on various metals and resins used in the fuel system of a diesel engine. Thus, it can be added directly or be diluted with a solvent for addition to diesel fuel oil in the fuel tank of a diesel car.
The additive dissolved in the fuel oil readily cleans up deposits produced in the injector nozzle when the engine is operated under normal conditions, thus pre-venting the nozzle from plugging with the deposits.
, ~ ~

'~''''''~
~-."'-- .. - ,-.

- , . . .
~ ~.,: .
,', ', ~ ~ ' ' '~ , ' ' - - ' 1273;~01 The additive of the invention further has the effect of improving low temperature fluidity of diesel fuel, of water draining, and of cleaning diesel engines, and fuel systems.
The following non-limitative Examples illustrate the invention, all percentages being by weight.
Example 1 A mixture of 40% of N,N-dihydroxyethyldodecylamine and 60~ of an n-butyl ether of polypropylene glycol (number average molecular weight: 1,800).
Example 2 A mixture of 10% of an N,N-dihydroxyethylated derivative of hydrogenated tallow amine, 40~ of a mono-n-butyl ether of polypropylene glycol (number average molecular weight: 1,100) and 50~ xylene.
Control 1 A mixture of 40% of N,N-dihydroxyethyldodecylamine, as mentioned in Example 1, and 60~ of a succinimide type dispersant (Lubrizol 8~4 made by Lubrizol Co.: a reaction produce of polyisobutene (molecular weight 1050), maleic anhydride, and tetraethylenepentamine)).
Test Example 1 The performance of cleaning up deposits in the nozzle of the injector of a diesel engine was tested on the additives of the invention in Examples 1 and 2 and on the additive in Control 1, by the following method:
Injector nozzles which were clogged by the attachment of deposits by an actual run were mounted on a diesel engine, and the engine was put to practical running for 2 hours by use of a diesel fuel oil on the market added with the additive of Examples 1 and 2 and in Control 1 to a concentration ~ of from zero to 1.0%, under conditions corresponding to - a practical run at 60 km~hr, to clean the deposit.
The flow rate at the nozzle when the needle lift was 0.1 to 0.5 mm was measured on the injector nozzle before and after cleaning by the air flow method. The capacity of cleaninq uP the deposit in the nozzle was compared by '`~ ~,~

, ~ ~ . , , .; . .
~'~'~ .: ' , ' ' - ' , ~ ,- , .
. .
:: , , :
.

1~'73;~0~

calculating the ratio of the nozzle flow rate to that of a new nozzle measured in advance.
The cleaning test results of the injector nozzle by the above method are shown in Table l.

Table l Additive~ olume ad~ed¦Ratio of nozzle flow rate (~
¦t~ O lmm li~t10.35mm lift10. mm i t A~r.......................... 1 24 1 40 c eanlng test:
i~a~I~ - _ -----T-- ~O 20 25 40 Examp e .
~: 15 l ~.0 85 93 95 Exam~le ' ~ 56 ~ Note l: The amount of additive added to the diesel fuel oil '; is indicated by % by weight.
; Note 2: Indicated by:
Nozzle flow rate before or after cleaning test x lO0 Nozzle flow rate of new injector nozzle ,.~
,, .~ .

~ :.
: - .
.

s`~ ~
'- ~, . .

, ~'-- A~
,, , ~ ' .. .
.~ . . . .

,: .
~. , . . - : , . .
.
. , .~ - , .
.

Claims (8)

THE EMBODIMENTS OF THE INVENTION IN WHICH AN EXCLUSIVE
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. A diesel fuel oil additive comprising (A) an oxyalkylene derivative of an amine having the general formula:

.................. (1) wherein R1 is an aliphatic hydrocarbon group having from 6 to 24 carbon atoms, A1 is an alkylene group having from 2 to 4 carbon atoms, ? and m are integers of 1 or more, with ? + m being a total of from 2 to 10; and (B) a polyoxyalkylene glycol mono-ether having the general formula:

R3-O-?A2O??- H .................. (2) wherein R3 is a hydrocarbon group having from 3 to 18 carbon atoms, A2 is an alkylene group having 3 or 4 carbon atoms and n is an integer of from 2 to 60.
2. An additive as claimed in claim 1, wherein R1 is an aliphatic hydrocarbon group having from 10 to 18 carbon atoms.
3. An additive as claimed in claim 1 or 2, wherein A1 is ethylene group.
4. An additive as claimed in claim 1 or 2, wherein ? + m is an integer of from 2 to 4.
5. An additive as claimed in claim 1, comprising N,N-dihydroxyethyldodecylamine and polypropylene glycol mono-n-butyl ether.
6. An additive as claimed in claim 1, comprising an N,N-dihydroxyethylated derivative of hydrogenated tallow amine and a mono-n-butyl ether of polypropylene glycol.
7. An additive as claimed in claim 1, 2 or 5, and including from 0.1 to 100 parts by weight of a solvent per part of the additive mixture.
8. A diesel fuel oil containing from 0.001 to 5% by weight of an additive as claimed in claim 1, 2 or 5.
CA000517494A 1985-09-20 1986-09-04 Additive to diesel engine fuel oil Expired CA1273201A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP60-209655 1985-09-20
JP20965585A JPS6268891A (en) 1985-09-20 1985-09-20 Additive for fuel oil

Publications (1)

Publication Number Publication Date
CA1273201A true CA1273201A (en) 1990-08-28

Family

ID=16576400

Family Applications (1)

Application Number Title Priority Date Filing Date
CA000517494A Expired CA1273201A (en) 1985-09-20 1986-09-04 Additive to diesel engine fuel oil

Country Status (3)

Country Link
JP (1) JPS6268891A (en)
CA (1) CA1273201A (en)
DE (1) DE3631225C2 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5197997A (en) * 1990-11-29 1993-03-30 The Lubrizol Corporation Composition for use in diesel powered vehicles

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4877416A (en) * 1987-11-18 1989-10-31 Chevron Research Company Synergistic fuel compositions
SE463028B (en) * 1988-02-22 1990-10-01 Berol Kemi Ab ETHANOL BRAZLE AND ITS APPLICATION AS DIESEL BRAZEN
JPH02194089A (en) * 1989-01-20 1990-07-31 Sanyo Chem Ind Ltd Additive for methanol fuel oil
GB9101884D0 (en) * 1991-01-29 1991-03-13 British Petroleum Co Plc Fuel composition
JP3560173B2 (en) * 1993-04-05 2004-09-02 株式会社ジョモテクニカルリサーチセンター Fuel composition for diesel engine
DE4313088A1 (en) * 1993-04-22 1994-10-27 Basf Ag Poly-1-n-alkeneamines and fuel and lubricant compositions containing them
GB9500460D0 (en) 1995-01-10 1995-03-01 Exxon Chemical Patents Inc Fuel compositions
PL191475B1 (en) * 1998-09-18 2006-05-31 American Energy Group Diesel fuel additive composition and method for the treatment of diesel fuels
JP5197305B2 (en) 2008-10-31 2013-05-15 油化産業株式会社 Diesel fuel additive composition and cleaning method using the same

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3115400A (en) * 1960-08-01 1963-12-24 Armour & Co Motor fuel composition
DE2064681B2 (en) * 1970-12-31 1973-01-04 Brenntag Kraft- Und Schmierstoff Gmbh & Co Kg, 4330 Muelheim Fuel additive to reduce the formation of residues in internal combustion engines, in particular vehicle engines, and to reduce pollutants in their exhaust gases
EP0152455B1 (en) * 1983-08-08 1989-06-14 Chevron Research And Technology Company Diesel fuel and method for deposit control in compression ignition engines

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5197997A (en) * 1990-11-29 1993-03-30 The Lubrizol Corporation Composition for use in diesel powered vehicles
US5360460A (en) * 1990-11-29 1994-11-01 The Lubrizol Corporation Composition and method relating to diesel powered vehicles

Also Published As

Publication number Publication date
JPH0349317B2 (en) 1991-07-29
JPS6268891A (en) 1987-03-28
DE3631225C2 (en) 1997-11-20
DE3631225A1 (en) 1987-04-23

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