OA12611A - Process for refining crude oils having high organic acidity. - Google Patents

Process for refining crude oils having high organic acidity. Download PDF

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Publication number
OA12611A
OA12611A OA1200300307A OA1200300307A OA12611A OA 12611 A OA12611 A OA 12611A OA 1200300307 A OA1200300307 A OA 1200300307A OA 1200300307 A OA1200300307 A OA 1200300307A OA 12611 A OA12611 A OA 12611A
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OAPI
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compound
process according
chosen
formula
crude oil
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OA1200300307A
Inventor
Paul Maldonado
Louis Genevois
Roland Barberet
Alain Catros
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Total France
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Publication of OA12611A publication Critical patent/OA12611A/en

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    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G11/00—Catalytic cracking, in the absence of hydrogen, of hydrocarbon oils
    • C10G11/14—Catalytic cracking, in the absence of hydrogen, of hydrocarbon oils with preheated moving solid catalysts
    • C10G11/18—Catalytic cracking, in the absence of hydrogen, of hydrocarbon oils with preheated moving solid catalysts according to the "fluidised-bed" technique
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G21/00—Refining of hydrocarbon oils, in the absence of hydrogen, by extraction with selective solvents
    • C10G21/06—Refining of hydrocarbon oils, in the absence of hydrogen, by extraction with selective solvents characterised by the solvent used
    • C10G21/12—Organic compounds only
    • C10G21/20—Nitrogen-containing compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G29/00—Refining of hydrocarbon oils, in the absence of hydrogen, with other chemicals
    • C10G29/20—Organic compounds not containing metal atoms
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G2400/00—Products obtained by processes covered by groups C10G9/00 - C10G69/14
    • C10G2400/02—Gasoline

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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)
  • Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention relates to a method of refining crude oils having high acidity by neutralising the organic acidity thereof. The inventive method consists in adding a nitrogenous compound to the crude oil. Said method is characterised in that a nitrogenous compound containing at least three carbon atoms, a secondary amine group and a hydric group is introduced at at least one point of the crude oil pre-treatment units upstream of, or in the atmospheric distillation unit.

Description

01261 1
The présent invention relates to a process for refining crude oils having high5 organic acidity.
The crude oils or fractions thereof having high acid contents are principallythose containing naphthenic acids. It is known that these crude oils présent risk ofcorrosion during extraction on the oil field, when they are transported, as well asduring their refinement. The petrol industry and the refining industry must find the 10 means to increase the value of these crude oils without being obliged to develop newtechnologies to protect devices and machinery for transporting these crude oils orfractions thereof or also for treating them whether it be on the field, in maritimetransport or by rail, in pipes or in the refinery. This crude oil acidity is usuallymeasured by the TAN number or index (Total Acid Number), which is measured by 15 potentiometric analysis in accordance with the standard ASTM D664 and bycolorimetry with the standard D974. Thus a discount is applied to the crude oils as afonction of the TAN index: the price of the crude oil dépends on the value of this „ acidity. Now today, most of the crude oils extracted are acidic by nature, that is tosay that they contain corrosive compounds like the sulphurated dérivatives but also 20 naphthenic acids. It can be understood why the development of a process for treatingthese crude oils which allows the obtention of a weak acidity in the entirety of thecrude oil or in the different carbonized cuts composing it would be bénéficiai: itwould allow both the increase of refining margins as well as the limitation of the riskof corrosion which is a generator of additional expenses in the case of perforations in 25 storage, transport or Processing equipment, particularly in refineries. Numerousefforts hâve been made in the past years to develop such a process of deacidificationor of neutralisation of crude oils.
Amongst the different ways which hâve been retained, neutralization bynitrogenous compounds, either combined or not combined with the use of a solvent, 30 has been mentioned particularly in the US patents 2769768, 3176041, -2911360,4634519 or 5550296.
The patent US-P-2769768 describes the use of a linear or branched primaryalcohol having from 4 to 7 atoms of carbon with a mixture formed froin methanoland from ammonia to neutralize and remove the heavy naphthenic acids from a 35 deparaffinated hydrocarbon oil.
The US patent 3176041 proposes trapping the naphthenic acids of a crude oilby contact with a clay impregnated with a volatile amine having a boiling pointbelow 100°C, particularly ammonium hydroxide. This process is not applicable in 2 01261 1 the crude oil production field, nor even in the refinery as a contact température above 200°C is required for 20 to 75 minutes and the extremely complex daily régénération of several hundred tons of clay.
The US patent 2911360 describes a process which is applied to a crude oil. Thecrude oil is deacidified in liquid phase by bringing it into contact with a base in thepresence of an alcohol, then distilled. The base can be ammoniac while the solventphase is an aqueous solution containing from 30 to 50% by weight of alcohol. Thenaphthenic acids recovered by distillation are regenerated after acidification in thesulphuric acid of the extraction solvent. This process is difficult as it involves twotreatments, one in the liquid phase and one in the vapour phase. Moreover it is onlyapplicable in the refinery as it involves atmospheric distillation and distillation undervacuum of the treated crude oil.
The patent US-P-4634519 describes a deacidification process of oil cuts usinga spécifie solvent mix, comprising water, methanol and ammoniac. It concemsextracting the naphthenic acids. This process is applied solely to oil cuts becauseapplying this treatment to a crude oil has lead to a stable émulsion rendering therecovery of the extraction solvent practically impossible.
The US patent 5550296 describes the synthesis of ketones, but also describes aprocess for deacidifying crude oil directly when it cornes out of the well in an oilfield, before stabilization of the crude oil, with liquid ammonia to neutralize thenaphthenic acids. Such a process cannot be implemented as it is in the refinery.
For the spécifie treatment of oil cuts of the type obtained by refining the crudeoil, taken separately, it has often been proposed to use nitrogenous compounds of themonoalkyl or monoarylamine type, optionally polymers of these amines, ofmonoalkanolamine, and even of tetraalkylised ammonium hydroxide as it isdescribed in the patents US-P-4589979, US-P-4752381, US-P-4827033, US-P-5683626, and EP 0924286A2.
None of the above documents either teaches or suggests the invention which ishere applied essentially to crude oil which is not yet distilled.
The aim of the présent invention is to convert into amides, the organic acidscontained in a crude oil having high acidity, principally the naphthenic acids, duringstandard refining of this crude oil in the refinery. The distilled fractions thusneutralized, are no longer the causes of major corrosion phenomena in the equipmentthrough which it passes. Moreover these cuts can even be made more valuable, thistreatment having the effect of favouring the appearance of amide functions whichimproves the qualities of the products marketed. Thus the addition of lubricityadditives to gasolines and middle distillâtes, kerosene and gas oil can be limited, thislubricity function in fact already being présent within the distilled eut. 3 01261 1 A subject of the présent invention is therefore a process for refining byneutralization of the organic acidity of crude oils having strong acidity eonsisting ofadding a nitrogenous compound to said crude oil, said process being characterized inthat, a nitrogenous compound comprising at least three carbon atoms, a secondary 5 amine group and a hydroxylated group is introduced into at least one point in the oilpretreatment unit upstream of, or in the atmospheric distillation unit.
Such compounds hâve the advantage of being able to react at low températureparticularly to neutralise the napthenic acids in amine salts, the amide formationbeing carried out by increasing the température of the crude oil before its distillation. 10 The amine salts which resuit from the naphthenic acids remain in the crude oil bothduring the crude oil preheating operations and during the desalting operations,progressively being converted into amides. Thus they are always présent but in theamide form in the crude oil when it enters into the atmospheric distillation fumace.Because of this the naphthenic acids thus amidified and the other amides optionally 15 formed from other acid compounds présent are distilled like the other hydrocarbonsand are found in the different cuts distilled in the usual way. It is foundadvantageously that these amides confer upon the distilled cuts unexpectedproperties of lubricity and of anti corrosion. Thus it has thus been seen that at thehead of the tower it was possible to limit or even to omit the addition of neutralising 20 amines. In addition, the cuts of middle distillâtes for the production of gas oils hâve agreatly reduced acidity and improved lubricity.
To obtain such results, the nitrogenous compounds used are chosen from thecompounds of formula (I) below
-W (I)
H-NI z 30 in which Y is a linear or branched alkyl group comprising from 1 to 10 carbonatoms, optionally hydroxylated, and Z is chosen from the alkyl, hydroxyalkyl andpolyhydroxyalkyl (containing up to 6, preferably up to 4 hydroxy), primary,secondary or tertiary amine groupe and their hydroxylated and polyhydroxylated 35 dérivatives, the alkyl fonctions of these groups comprising from 1 to 10 carbon atoms. 012611 10 Ο 15 '20 Ο 25 30
In a first preferred embodiment of the invention, a compound of formula (I) isused in which Z is a group chosen from the hydroxyalkyl and polyhydroxyalkylgroups.
The compounds of formula (I) preferred in this first embodiment are chosenfrom the dialkanolamines of the group constituted by diethanolamine,dipropanolamine, dibutanolamine, N-propanol-2-ethanolamine, N-butanol-2-ethanolamine, N-butanol-3-ethanolamine, N-butanol-2-propanolamine, N-butanol-3-propanolamine, N-propanol-2-butanolamine, di-(methyll-hydroxy2)-propylamine,diisopropanolamine and di-(methyl2hydroxy2)-butylamine.
For optimal effectiveness of the process according to the invention, thepreferred compounds are chosen from diethanolamine and diisopropanolamine.
In a second embodiment of the invention, a compound of formula (I) is used inwhich Z is an alkyl group comprising from 1 to 5 carbon atoms.
The compounds of formula (I) are chosen from N-methyl-ethanolamine, N-propyl-ethanolamine, N-butylethanolamine, N-isobutylethanolamine, N-pentylethanolamine, N-methylpropanolamine, N-isopentylethanolamine, N-propyl-propanolamine, N-butylpropanolamine, N-isobutylpropanolamine, N-pentylpropanolamine, N-isopentylpropanolamine, N-methyl-butanolamine, N-propyl-butanolamine, N-butylbutanolamine, N-isobutyl-butanolamine, N-pentylbutanolamine, N-isopentylbutanolamine, N-methyl-pentanolamine, N-propyl-pentanolamine, N-butylpentanolamine, N-isobutylpentanolamine, N-pentylpentanolamine and N-isopentylpentanolamine. In an optimal embodiment, N-propylethanolamine and N-isobutyleth‘anolamine are preferred as compounds offormula (I).
In a third embodiment of the invention, a compound of formula (I) is used inwhich Z is chosen from the amine primary, secondary and tertiary amine groups andtheir monohydroxylated and polyhydroxylated dérivatives.
The preferred compounds in this third embodiment are chosen from the groupconstituted by N-hydroxy-2-ethylhydrazine, N-hydroxy-2-ethylethylenediamine, N-hydroxy-2-ethyl-(l-3)propylenediamine, N,N’-bis(dihydroxy-2,3-propyl)amine andhydroxy-2-(l ,3)propylenediamine. Preferably N-hydroxy-2-ethylethylenediaminewill be chosen.
In order to neutralise then amidify the organic acids of the crude oil to berefined, the compound of formula (I) can be introduced before the crude oil desaltingunit, when preheating of the desalted crude oil is underway, preferably before thepreheaters or also in the still tower. 35 01261 1 10 ( ) 15 20 Ο 25
Another subject of the invention is the application of the process to theneutralisation of the organic acids contained in die crude oils having acidity higherthan 0.5mg KOH/g. A third subject of the invention corresponds to the oil cuts obtained byapplying said process according to the first subject of die invention.
Amongst these oil cuts there are the middle distillâtes with a eut températurecomprised between 150 and 400°C. A second type of eut corresponds to the cuts which are called light with euttempératures comprised between the starting point and 150°C and with acidity below0.5mg of KOH/g.
The invention will now be described on the basis of examples given belowintending to illustrate the characteristics of the invention but without wishing to limitits scope.
EXAMPLE I
The présent invention describes the process for conversion of organic acids of acrude oil withnitrogenous compounds according to the invention. A crude oil A with moderate acidity (12.9 mmoles of carboxylic acid/1 of crudeoil) is used on the one hand and a crude oil B with high acidity (68.1 mmoles ofcarboxylic acid/1 of crude oil) is used on the other hand. 201 of crude oil and thecompound of formula (I) here diethanolamine (or DEA) are introduced into anagitated reactor. The crude oils A and B thus complemented are then subjected toinfrared analysis. It is found that the acid peak disappears at 1708cm-1 in the twocrude oils A and B. There has thus been a conversion of the carboxylic acids tocarboxylic acid sait. Then the température of complemented A and of B is raised to150° for 30 minutes in order to amidify these salts.
These crude oils thus amidified are then introduced into a distillation pilot. Thethus distilled oil cuts are then subjected to infrared analysis. These different cuts arecompared with the identical cuts of the pure crude which is not treated but distilled inthe same distillation pilot plant. It is found that in these cuts the carboxylic acidshâve indeed disappeared and that amide compounds hâve indeed been formed.
The details of the distilled cuts are given in the Table (I) below. The résulte aregiven in mmoles of carboxylic acid per litre of hydrocarbons. 30 01261 1
TABLEI A B Without With DEA Without With DEA Weight ofadded DEA 0 52g 0 275g PI-150 0 0 0 0 150-230 15.2 3 0 0 230-350 32.7 11.4 34.8 11,5 350-400 29.2 14 94.2 40,1 400+ 0 0 15 9
From this table established by analysis of the graphs obtained by infrared 5 analysis it is seen that in ail the cuts obtained from the treated product beforedistillation, a notable réduction in the carboxylic acid content and thus in corrosiveChemical species is observed. This is particularly true for the gas oil eut, distilledbetween 230 and 350°C in which the majority of naphthenic compounds are _concentrated. 10
Example II
The présent example aims to describe the advantages linked to the process asregards the improvement in lubricity of the middle distillate cuts and theanticorrosive effect of the amides formed in the light distillation cuts. 15 Thus the 230-350°C cuts from Example I with and without amide formation before distillation are taken up and the lubricity of each one of them is measured bythe"method known as HFRR (High Frequency Reciprocating Ring), according to thestandard EC121561. It is expressed by Wear Scare Diameter (WSR) in pm. A correctlubricity leads to wear diameter values below 460pm. The smaller this value is, the 20 better is the lubricity.
The results are given in Table II below. 012671 TABLEΠ
Cut A B Without With DEA Without With DEA Acidity (mmole COOH/1) 32.7 11,4 34,8 11,5 Lubricity (pm) 255 265 292 310
The résulte show that, although the carboxylic acids and in particular the5 naphthenic acids hâve a rôle that is well known in improving lubricity, thedisappearance of these acids by amidifying them does not hâve a harmful effect onthe lubricity. The effect of the acids as an improver of lubricity of the gas oil eut(230-350°C), in particular that of the crude oils having strong organic acidity (B), was replaced by the effect of the corresponding amide. 10
Example III
The présent example aims to show the progressive character of the reaction ofthe alkanolamines in particular of the diethanolamine (DEA) on the crude oil B withacidity corresponding to a TAN of 4.47 or 68 mmole/1 of acidity measured. 15 To monitor the reaction, 434g of crude oil B and 13 ml of DEA diluted to 40% by weight in water are introduced into a 500 ml flask. DEA is gradually added over50 minutes while stirring the mixture with a standard magnetic stirrer.
This addition is followed by a heating of the crude oil B to 100°, then to 150°Cfor 30 minutes. The température is then stabilized at 180°C after 2 hours.
20 The reaction is monitored in crude oil while DEA is added by IRFT spectrometiy using a measuring stick dipped in the crude oil B forming a part of theREACT IR spectrometry marketed by the company METTLER. Periodically duringthis reaction the infrared spectrums of the product contained in the flask aremeasured. 25 Figures 1 and 2 give a représentation of the évolution of the infrared spectrums during the addition of DEA and during the heating in relation to time.
Figure 1 présents, three dimensionally, the disappearance of the aciddérivatives (band centred on the wavelength 1710cm-1), the appearance of aminesalts (band centred on 1560cm-1) and the appearance of the amides (band centred on 30 1650cm-1).
Figure 2 représente, in two dimensions, in relation to time, the formation of amide (band centred on 1650cm-1) after addition of DEA and the maintenance of - crude oil B at 140°C for one hour; The formation of esters in a small quantity linked · .istl ;;· ,' . ; , y. · / 012611 8 to the presence of watër brought on by the addition of DEA (band centred on1740cm"1 ) is also noted.

Claims (12)

  1. 9 012611 CLAIMS
    1. Process for refîning by neutralisation of the organic acidity of crudeoils having an organic acidity and total acidity TAN higher than 0.5mg KOH/g 5 consisting of adding a nitrogenous compound to said crude oil, said process beingcharacterized in tirât there is introduced in at least one point of the unit ofpretreatment of crude oil upstream of or in the unit of atmospheric distillation anitrogenous compound comprising at least three carbon atoms, a secondary aminegroup and a hydroxylated group. 10
  2. 2. Process according to claim 1 characterized in that the nitrogenouscompounds used are chosen from the compounds of formula (I) below O Y-OH 15 l H-N ~ (I) I Z 20 in which Y is a linear or branched alkyl group comprising from 1 to 10 carbon atoms, optionally hydroxylated, and Z is chosen from the alkyl, hydroxyalkyl, andpolyhydroxyalkyl, primary, secondary or tertiary amine groups and theirhydroxylated and polyhydroxylated dérivatives, the alkyl functions of these groupscomprising from 1 to 10 carbon atoms. 25
  3. 3. Process according to claim 2 characterized in that in the compound offormula (I), the Z is a group chosen from the hydroxyalkyl and polyhydroxyalkylgroups.
  4. 4. Process according to claim 2 or 3 characterized in that the compound of formula (I) is chosen from the group constituted by diethanolamine,dipropanolamine, dibutanolamine, N-propanol-2-ethanolamine, N-butanol-2-ethanoîamine, N-butanol-3-ethanolamine, N-butanol-2- propanolamine, N-butanol-3-propanolamine, N-propanol-2-butanolamine, di-(methyl l-hydroxy2)-propylamine, 35 diisopropanolamine and di-(methyl2hydroxy2)-butylamine.
  5. 5. Process according to claim 4 characterized in that the compound of formula (I) is chosen from diethanolamine and diisopropanolamine. t I 10 012611
  6. 6. Process according to daim 2 characterized in that in the compound offormula (I), Z is an alkyl group comprising from 1 to 5 carbon atoms.
  7. 7. Process according to claim 6 characterized in that the compound of formula (I) is chosen from N-methyl-ethanolamine, N-propyl-ethanolamine,N-butylethanolamine, N-isobutylethanolamine, N-pentylethanolamine, N-methyl-propanolamine, N-isopentylethanolamine, N-propyl-propanolamine, N-butylpropanolamine, N-isobutylpropanolamine, N-pentylpropanolamine, N- 10 isopentylpropanolamine, N-melhyl-butanolamine, N-propyl-butanolamine, N- butylbutanolamine, N-isobutyl-butanolamine, N-pentylbutanolamine, N- isopentylbutanolamine, N-methyl-pentanolamine, N-propyl-pentanolamine, N- f } butylpentanolamine, N-isobutylpentanolamine, N-pentylpentanoîamine and N- isopentylpentanolamine. 15
  8. 8. Process according to daims 6 and 7, characterized in that thecompound of formula (I) is chosen from N-propylethanolamine and N-isobutylethanolamine.
  9. 9. Process according to claim 2 characterized in that in the compound of formula (I), Z is chosen from the primary, secondary and tertiary amine groups andtheir monohydroxylated and polyhydroxylated dérivatives.
  10. 10. Process according to daim 9 characterized in that the compound of 25 general formula (I) is chosen from the group constituted by N-hydroxy-2-ethylhydrazine, N-hydroxy-2-ethylethylenediamine, N-hydroxy-2-ethyl-(l-3)propylenediamine, N,N’-bis(dihydroxy-2,3-propyl)amine and hydroxy-2-(1,3)propylenediamine.
  11. 11. Process according to daims 9 and 10 characterized in that the compound of formula (I) is N-hydroxy-2-ethylethylenediamine.
  12. 12. Process according to daims 1 to 11 characterized in that thenitrogenous compound is introduced before the crude oil desalting unit, during 35 preheating of the desalted crude oil, preferably before the heat exchangers or also inthe distillation tower.
OA1200300307A 2001-06-01 2002-05-31 Process for refining crude oils having high organic acidity. OA12611A (en)

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FR0107247A FR2825369B1 (en) 2001-06-01 2001-06-01 PROCESS FOR PROCESSING RAW OIL WITH HIGH ORGANIC ACIDITY

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US (1) US20040134838A1 (en)
EP (1) EP1397468A1 (en)
JP (1) JP2004533516A (en)
CA (1) CA2452327C (en)
FR (1) FR2825369B1 (en)
NO (1) NO20035345D0 (en)
OA (1) OA12611A (en)
WO (1) WO2002097014A1 (en)
ZA (1) ZA200308957B (en)

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Publication number Priority date Publication date Assignee Title
US20100155304A1 (en) * 2008-12-23 2010-06-24 Her Majesty The Queen In Right Of Canada As Represented Treatment of hydrocarbons containing acids
US9670423B1 (en) 2013-03-11 2017-06-06 Sochem Solutions, Inc. SoNap unit : portable naphthenic acid springing unit

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2186249A (en) * 1939-01-17 1940-01-09 Tide Water Associated Oil Comp Process of recovering organic acids
US2424158A (en) * 1944-09-20 1947-07-15 Standard Oil Dev Co Process of refining a petroleum oil containing naphthenic acids
FR2112036A1 (en) * 1970-07-24 1972-06-16 Gamlen Naintre Sa Crude oil treatment compsn - contg surfactant(s) and alcohol(s),amide(s) or phenol(s)
US4589979A (en) * 1985-08-22 1986-05-20 Nalco Chemical Company Upgrading heavy gas oils
US5965785A (en) * 1993-09-28 1999-10-12 Nalco/Exxon Energy Chemicals, L.P. Amine blend neutralizers for refinery process corrosion
US5961821A (en) * 1998-03-27 1999-10-05 Exxon Research And Engineering Co Removal of naphthenic acids in crude oils and distillates
US6096196A (en) * 1998-03-27 2000-08-01 Exxon Research And Engineering Co. Removal of naphthenic acids in crude oils and distillates

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EP1397468A1 (en) 2004-03-17
WO2002097014A1 (en) 2002-12-05
US20040134838A1 (en) 2004-07-15
CA2452327A1 (en) 2002-12-05
NO20035345D0 (en) 2003-12-01
CA2452327C (en) 2010-06-29
FR2825369A1 (en) 2002-12-06
JP2004533516A (en) 2004-11-04
ZA200308957B (en) 2004-09-16

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