CA2437761A1 - Octane enhancing additive for gasoline - Google Patents

Octane enhancing additive for gasoline Download PDF

Info

Publication number
CA2437761A1
CA2437761A1 CA 2437761 CA2437761A CA2437761A1 CA 2437761 A1 CA2437761 A1 CA 2437761A1 CA 2437761 CA2437761 CA 2437761 CA 2437761 A CA2437761 A CA 2437761A CA 2437761 A1 CA2437761 A1 CA 2437761A1
Authority
CA
Canada
Prior art keywords
gasoline
octane
less
volume
methylaniline
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.)
Abandoned
Application number
CA 2437761
Other languages
French (fr)
Inventor
Abdel M. Kharrat
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.)
SATEE MARKETING OF CANADA Inc
Original Assignee
SATEE MARKETING OF CANADA INC.
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 SATEE MARKETING OF CANADA INC. filed Critical SATEE MARKETING OF CANADA INC.
Priority to CA 2437761 priority Critical patent/CA2437761A1/en
Publication of CA2437761A1 publication Critical patent/CA2437761A1/en
Abandoned 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
    • C10L10/00Use of additives to fuels or fires for particular purposes
    • C10L10/10Use of additives to fuels or fires for particular purposes for improving the octane number
    • 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
    • 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
    • C10L1/182Organic compounds containing oxygen containing hydroxy groups; Salts thereof
    • C10L1/1822Organic compounds containing oxygen containing hydroxy groups; Salts thereof hydroxy group directly attached to (cyclo)aliphatic carbon atoms
    • C10L1/1824Organic compounds containing oxygen containing hydroxy groups; Salts thereof hydroxy group directly attached to (cyclo)aliphatic carbon atoms mono-hydroxy
    • 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
    • C10L1/223Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond having at least one amino group bound to an aromatic carbon atom

Landscapes

  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Combustion & Propulsion (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Liquid Carbonaceous Fuels (AREA)

Abstract

An octane increasing additive for gasoline, which includes N-methylaniline or N-ethylaniline, with aniline and ethanol. There is not less than 5% and not more than 70% by volume of at least one of N-methylaniline or N-ethylaniline.
There is not less than 10% and not more than 50% by volume of aniline. There is not less than 5% and not more than 60%
by volume of ethanol.

Description

TITLE OF THE INVENTION:
Octane enhancing additive for gasoline FIELD OF THE INVENTION
The present invention relates to an octane enhancing additive for gasoline.
BACKGROUND OF THE INVENTION
Gasoline fraction obtained from crude oil distillation typically has an octane number of around 80. In addition to refinery upgrading processes, octane enhancing additives have been used to improve the octane number. The octane number must be increased from 80 to 87 for regular grade gasoline and to 91 for premium gasoline.

One commonly used octane enhancing additive for gasoline was tetraethyl lead. Tetraethyl lead was banned after it was discovered to contribute to human health problE;ms. Another commonly used octane enhancing additive for gasoline was methyl t-butyl ether (MTBE). MTBE was also discovered to create environmental problems. Zarge quantities of MTBE have been released into the environment from leaking underground storage tanks. Where such leakage occurred, the MTBE
contaminated the water table, because of its high mobility and water solubility.
There are numerous chemical additives, which are capable of increasing the octane number of gasoline. It is difficult, however, to find additives which are capable of achieving very high octane increases with very small quantity additions to gasoline. It is also difficult to find additives with acceptable physical characteristics, which will have relatively low potential environmental and toxicological impact.

SUGARY OF THE INi7ENTION
What is required is an octane increasing additive for gasoline which is capable of achieving very high octane increases with relatively small quantity additions to gasoline and relatively low potential environmental and toxicological impact.
According to the present invention there is provided an octane increasing additive for gasoline,. which includes N-methylaniline and/or N-ethylaniline, with aniline and ethanol. There is not less than 5o and not more than 70o by volume of at least one of N-methylaniline or N-et:hylaniline.
There is not less than loo and not more than 50~ by volume of aniline. There is not less than 5% and not more than 600 by volume of ethanol.
The normal additional of the octane increasing additive into the gasoline is in the 1o to loo range.
In applications in which vapour pressure is of concern, iso-octane can be added to increase the vapour px°essure for the additive.
DETAILED DESCRIPTIO1~T OF TF3E PREFERRED E1~IBODII~TT
The preferred octane increasing additive for gasoline will now be descr_bed. During product development, the additive was identified as H.O.P.E which stands for "High Octane Power Enhancer'°. In the description which follows and the supporting charts and graphs, the additive is identified as H.O.P.E.
H . O . P . E . deve~.opment H.O.P.E. is a newly designed gasoline additive that enhances research (RON), motor (MON) octane numbers and, consequently, the anti-knock index.
Testing Methods H.O.P.E. was tested at the laboratories of thE: Alberta Research Council using standard methods. Among them ASTM
methods 2699 and 2700 that were used for RON and MON
respectively. H.O.P.E. could be added to gasoline at ranges of 1-100 (v/v).
Performance H.O.P.E. performance is very good as shown in the following graph. The enhancement of octane number with H.O.P.E. is much larger than with other additives tested or MTBE as shown on the graph. This addition rate could be adjusted based on the formulation of H.O.P.E. and also based on the octane number of the gasoline.
Testing dosage in increments of 10 of H.O.P.E. allows increase of RON from 77.8 to 81.4 resulting in a boosting effect of 3.6 points compared to 1.1 of MTBE.
1~

.

1.4 ---. . .
a- ~ -oH
~E.
O
P

~~ . _ .
.

o qp .. . _ --~-Ethanol m ~ .. tso-octane . ,_...-~- ' --~ MTB~

~.~,~

.

o . ~ ~ I

0 1 ~ 3 d 5 PERCENTADDED

Dosage: lo, 20, 3o and 5a of H.O.P.E. increases gasoline RON by up to 3.6 5 points of H.O.P.E. increases gasoline RON by up to 7.5 points of H.O.P.E. increases gasoline RON by u~> to 10.8 points 10 5% of H.O.P.E. increases gasoline RON by u~> to 15.6 points, Based on these results, the following informatic>n is compiled, a At 1o dosage, one(1) ton of H.O.P.E. treats'. 100 tons of base gasoline resulting in 101 tons of treated gasoline with RON increase of 3.6 points.
To perform this, simply add 1 ton of H.~.P.E. to 10~ tons of base gasoline.
At 2o dosage, two (2) tons of H.O.P.E. treats 100 tons of base gasoline resulting in 102 tons of treated gasoline with RON increase of 7.5 points.
At 5o dosage, one (1) ton of H.O.P.E, treats 20 tons of base gasoline resulting in 21 tons of treated gasoline with RON increase of 15.6 points.
Physical Characteristics H.O.P.E. is a mixture of liquid organic chemicals.
These chemicals have a clear to slightly yellow colour, no metals and no phosphorus as determined by ASTM methods. The vapor pressure of its major constituents is lower than gasoline. No lead is present in H.O.P.:E. and other constituents are with specification.

Environmental and Toxicological impact H.O.P.E. environmental parameters (Kow, Koc) are estimated to be similar to gasoline's, as shown in the table below. Its solubility in water is smaller than MTBE°S.
It's lower vapor pressure than gasoline makes it less susceptible for inhalation. Its flash point is estimated to be 37 C and its TGA flammability classification is 3. It°s freezing point is less than -10 C. The major constituents of H.O.P.E. are much less toxic than other additives such as MMT, based on comparison of LD50 values.

I~tihemlc~!'B~ 1~P W~l~r9aluE~lltLo l~~w6fa~ L~GD

tienxona 8ta X4.5 5 ~. ~ 2~ ~.i3 $~ fTI~~
C m m !k mouse ora E~P~T ~~3 O.t?f~ 0 2~ ll 3.7 ND 5tt r~
C mmH ~5 r3 drat ~ITBt: 5f ~541i ~5 51 I ~S ~.~4 8 28~ oral G

Eth~n~l 7~ 59,3 ~5 r~~cible -0.39 ND 1~;~7 !fit C m~r:H Gr~l ASV-acne 99 40.8 21 a ND same ~ali~
G mreli us N.~t t 245 t7~?A 26 ~~a ~1 B 1 2r~ 334 m r oral arrilln$ C rnmli Conclusion H.O.P.E. is a very efficient in. boostincr antiknock index for gasoline. It is an attractive and very promising additive since it exhibits low water solubility, low toxicity and low mobility in the environment. Its addition to gasoline clid not show any change to the regular emitted chemicals (emissions) from tail pipes. This classifies H.O.P.E, as environmentally friendly additive.
Broad tnlorking Range:
not less than 5o and not more than 70% by volume of at least one of N-methylaniline or N-ethylaniline;
not less than loo and not more than 50o by volume of aniline; and not less than 5o and not more than 60o by volume of ethanol.
In this formulation a synergy is obtained through use of aniline in combination between N-methylaniline, N-ethylaniline or a combination of both. Ethanol is added to control environmental emissions by providing oxygen for improved combustion of the gasoline. Minimum levels are specified, as below those minimum levels the des~_red beneficial effect is not achieved. Maximum level: are specified, as above those maximum levels room is being taken up in the formulation which is necessary for the other ingredients. Where vapour pressure is of-_ concern, not less than 5o and not more than 30% by volume of iso-ocaane is added.
Preferred Working Range:
not less than 30o and not more than 65o by volume of at least one of N-methylaniline or N-ethylanil_ine;
not less than 20o and not more than 60o by volume of aniline; and not less than 5o and not mare than 45o by volume of ethanol.
The preferred range sets forth a narrower working range, which it is recommended that one skilled in the art operate within in order to achieve the best results.
Sample Formulation Io 60o N-methylaniline or N-ethylaniline 30o Aniline 10o ethanol Sample Formulation II:

15o N-methylaniline 15o N-ethylaniline 20o aniline loo iso-octane 40o ethanol Variations:
Sample formulation I is prepared to obtain a maximum octane boost, without regard to other factors. 600 of that formulation includes N-methylaniline, N-ethyla.niline or a combination of both. This is combined with a further 300 aniline. Whether sample formulation I set forth above is used will depend upon a number of factors. One factor is oxygen content of the gasoline and the emissions produced by the gasoline. Another factor is the compos_Ltion of the gasoline. A practical consideration will, at times, be the cost and availability of the constituent chemicals. The cost per litre of gasoline must be kept as low as possible. If the price of N-methylaniline were to rise significantly, substitution would have to be made for. increased quantities of the other ingredients. Sample formulation II demonstrates an adjusted formulation, that still falls within the preferred ranges. Such a formulation might be used if N-methylaniline and N-ethylaniline were to increase in price or become difficult to obtain in desired quantitif=s. It also might be used if adjustments were required to increase oxygen content and reduce environmental emissions. Iso-octane would be added to reduce vapour pressure, in order to reduce gasoline evaporative emissions.
The Charts which follow demonstrate performance obtained in preliminary tests.

CCTA~11~E ENHANCEI~'S
methyleniline R~N M4IV OCi~r~~
added ~

0 90.4 81.8 86.~

1 93.8 84.5 89.~
2 96.8 85.8 9'i.~
3 98.fi 86_9 928 98 ~ - .~.~-g6 _ . . __ .. . ~. -~--Se~es1 m ga _ .. . --r~-Series2 n.
8g . -.- _. - ~ Se~ies3 82 - --------- .
8g N-MethylaaHi~te °l°

1.
100 ---, i 99 --.

z 95 -92 __ _._ ..

~l~
MA - N-methylaniline A - aniline MI - methyl iodide EA - N-ethylaniline DMA - N-dimethylaniline Isoct- iso-octane -~ 5 Chemical BP VP LD50 Water to Koc aol Kew benzene 80C 94.8 5C 4700 m !dc 1.8 !I 2.13 82 mmH Mouse oral 26C

MMT 233C 0.047 OC 50 m Ik rat 29 m 3.7 NLD
mmH anal 5C

M'fBE 55C 250 3C 2960 rn Rat 51 I 0.94 6 mmH oral 25C

Aniline 184C 0.49 25C 230 m k Rat 36 n 0.9 63 mmH ora! 3C

Ma Anilinel9fiC0.453 5C similar to 5.6 I! l.fifi65 mm aniline 25C
N

Ethanol 78.5059.3 25C 12387 m lk Miscible-0.31 NC
mmH Rat oral isooctane99C 40.6 c$21Csame as gasoline~ 0 ] / mmli ( In this patent document, the word '°compri;sing°' is used in its non-limiting sense to mean that items following the word are included, but items not specifically mentioned are not excluded. A reference to an element by t:he indefinite article "a'° does not exclude the possibility that more than one of the element is present, unless the context clearly requires that there be one and only one of the elements.
It will be apparent to one skilled in 'the art that modifications may be made to the illustrated embodiment without departing from the spirit and scope of the invention as hereinafter defined in the Claims.

Claims (8)

1. An octane increasing additive for gasoline, comprising:
not less than 5% and not more than 70% by volume of at least one of N-methylaniline or N-ethylaniline;
not less than 10% and not more than 50% by volume of aniline; and not less than 5% and not more than 60% by volume of ethanol.
2. The octane increasing additive for gasoline as defined in Claim 1, further including not less than 5% and not more than 30% by volume of iso-octane.
3. The octane increasing additive for gasoline as defined in Claim 1, including N-Methylaniline, but not N-ethylaniline.
4. The octane increasing additive for gasoline as defined in Claim 1, including N-ethylaniline, but not N-Methylaniline.
5. The octane increasing additive for gasoline as defined in Claim 1, including both N-Methylaniline and N-ethylaniline.
6. The octane increasing additive for gasoline as defined in Claim 1, comprising:
not less than 30% and not more than 65% by volume of at least one of N-methylaniline or N-ethylaniline;
not less than 20% and not more than 60% by volume of aniline; and not less than 5% and not more than 45% by volume of ethanol.
7. The octane increasing additive for gasoline as defined in Claim 6, further including not less than 5% and not more than 30% by volume of iso-octane.
8. An octane increasing additive for gasoline, comprising:
not less than 30% and not more than 65% by volume of a mixture of N-methylaniline and N-ethylaniline;
not less than 20% and not more than 60% by volume of aniline;
not less than 5% and not more than 45% by volume of ethanol; and not less than 5% and not more than 10% by volume of iso-octane.
CA 2437761 2003-08-20 2003-08-20 Octane enhancing additive for gasoline Abandoned CA2437761A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CA 2437761 CA2437761A1 (en) 2003-08-20 2003-08-20 Octane enhancing additive for gasoline

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CA 2437761 CA2437761A1 (en) 2003-08-20 2003-08-20 Octane enhancing additive for gasoline

Publications (1)

Publication Number Publication Date
CA2437761A1 true CA2437761A1 (en) 2005-02-20

Family

ID=34230645

Family Applications (1)

Application Number Title Priority Date Filing Date
CA 2437761 Abandoned CA2437761A1 (en) 2003-08-20 2003-08-20 Octane enhancing additive for gasoline

Country Status (1)

Country Link
CA (1) CA2437761A1 (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008076759A1 (en) * 2006-12-14 2008-06-26 Shell Oil Company Fuel composition and its use
WO2010001341A2 (en) * 2008-06-30 2010-01-07 Chimec S.P.A. Production process of unleaded high octane number gasoline, and so obtained gasolines
RU2576327C1 (en) * 2015-03-31 2016-02-27 Евгений Владимирович Ройтман Antidetonation additive and fuel with claimed additive

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008076759A1 (en) * 2006-12-14 2008-06-26 Shell Oil Company Fuel composition and its use
WO2010001341A2 (en) * 2008-06-30 2010-01-07 Chimec S.P.A. Production process of unleaded high octane number gasoline, and so obtained gasolines
WO2010001341A3 (en) * 2008-06-30 2010-02-25 Chimec S.P.A. Production process of unleaded high octane number gasoline, and so obtained gasolines
RU2576327C1 (en) * 2015-03-31 2016-02-27 Евгений Владимирович Ройтман Antidetonation additive and fuel with claimed additive

Similar Documents

Publication Publication Date Title
US6767372B2 (en) Aviation gasoline containing reduced amounts of tetraethyl lead
JP5856467B2 (en) Improved fuel additive formulations and methods of use
JP5068669B2 (en) Reduced RVP oxygenated gasoline composition and method
DE60306250T2 (en) Friction modification additives for fuel compositions and methods of use thereof
US20050229479A1 (en) Fuel compositions and methods thereof
US20090199464A1 (en) Reduced RVP Oxygenated Gasoline Composition And Method
JP2009544787A (en) Fuel composition
US4806129A (en) Fuel extender
WO2010001341A2 (en) Production process of unleaded high octane number gasoline, and so obtained gasolines
CA2437761A1 (en) Octane enhancing additive for gasoline
BR112017027947B1 (en) IMPROVED OCTANE NUMBER GASOLINE COMPOSITIONS
AU2010200065B2 (en) Improved fuel additive formulation and method of using same
TW457292B (en) Fuel compositions containing tertiary-alkyl primary amines and method of providing thermal stability to fuel containing cetane improvers
AU2013200840B2 (en) Improved fuel additive formulation and method of using same
Tsarev et al. Increase of the environmental and operational characteristics of automobile gasolines with the introduction of oxygenates
EP3417038A1 (en) Process for preparing tier 3 reference fuel
Hariharan et al. IMPACT OF OXYGENATE (ANHYDROUS ETHANOL) ON THE PHYSICO-CHEMICAL PROPERTIES OF BHARAT STAGE III GASOLINE
AU2011226816A1 (en) Reduced RVP oxygenated gasoline composition and method
PL177131B1 (en) Low-lead petrol comprising ethanol

Legal Events

Date Code Title Description
EEER Examination request
FZDE Dead