US2251773A - Solvent treatment of hydrocarbon oils - Google Patents

Solvent treatment of hydrocarbon oils Download PDF

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US2251773A
US2251773A US250500A US25050039A US2251773A US 2251773 A US2251773 A US 2251773A US 250500 A US250500 A US 250500A US 25050039 A US25050039 A US 25050039A US 2251773 A US2251773 A US 2251773A
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oil
morpholine
solvent
naphthenic
oils
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US250500A
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Meyer S Agruss
Wesley H Sowers
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Pure Oil Co
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Pure Oil Co
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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
    • 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

Definitions

  • This invention relates to extraction methods of refining mineral oils and has particular reference to methods for extracting such oils by means of solvents whereby fractions of different chemical composition though of the same distillation range, are obtained.
  • mineral oils such as petroleum comprise essentially a mixture of various groups or homologous series of compounds such, for example, as paraffins, olefins, hydroaromatics, polymethylenes and other series of compounds of chain and/or ring structure and in which the hydrogen to carbon ratio is less than in the aforementioned series.
  • Crude petroleum oils are generally classified into three types, namely, paraffinic, naphthenic and mixed base, which contain the various series of. hydrocarbons mentioned heretofore, in varyingpropcrtions. , Perhaps the best known exam.-
  • ple of a parafiinic base crude oil is one obtained diate between the paraflinic and naphthenic base type crude oils.
  • the parafiinic type crude oils and their. distillates may be distinguished from the naphthenic type crude oils and their distillates by certain arbitrary constants used extensively in the oil refining industry.
  • the first of these constants is known as the viscosity index and is a coefficient based on the change of viscosity with temperature. This is described by Dean and Davis, Chemical and Metallurgical Engineering, vol. 36, page 618, 1929.
  • the second of the constants referred to is the viscosity-gravity constant. This is a constant expressing a relation between viscosity and specific gravity and is described by Hill and Coates in Industrial and Engineering Chemistry, vol 20, page 641. V
  • the more paraffinic oils are characterized by relatively lower viscosity-gravity constants and relatively higher viscosity indices, while the more naphthenic oils are characterized by higher viscosity-gravity constants and lower viscosity indices.
  • An object of the invention is to provide a method for separating viscous mineral oils into fractions by means of solvents.
  • Another object of the invention is to provide a method ,for increasing the parafiinicity of min.- eral lubricating oils,
  • Still another object of the invention is to provide a new extracting agent for separating viscous mineral oils into paraffinic and naphthenic fractions.
  • oils containing both parafiinic and various naphthenic. hydrocarbons may be fractionally extracted with a selective solvent such as morpholine (tetrahydroparoxazine) and derivatives thereof such as those derivatives in which one or more hydrogen atoms in the morpholine molecule is substituted by alkyl groups.
  • a selective solvent such as morpholine (tetrahydroparoxazine) and derivatives thereof such as those derivatives in which one or more hydrogen atoms in the morpholine molecule is substituted by alkyl groups.
  • morpholine tetrahydroparoxazine
  • derivatives thereof such as those derivatives in which one or more hydrogen atoms in the morpholine molecule is substituted by alkyl groups.
  • ethyl tetrahydroparoxazine l methyl tetrahydroparoxazine
  • 1 butyl tetrahydroparoxazine and others.
  • the various series of hydrocarbons possess a different solubility in such solvent, the naphthenic hydrocarbons being much more soluble therein than the parafiinic hydrocarbons.
  • mineral oil containing both series of hydrocarbons is extracted with a solvent of the class above set forth, it is possible to effect a partial separation of the parafiinic from the .naphthenic hydrocarbons and to obtain a fraction which is more parafiinic than the original oil and one which is more naphthenic.
  • an oil of the mixed base type such as is frequently found in the Mid-Continent area it is possible to produce an oil of a more paraffinic type such as is generally found in the Pennsylvania oil fields.
  • oils which are respectively more parafiinic and more naphthenic than the oils normally obtained from such source by distillation.
  • the oil to be treated is first mixed with morpholine or a suitable derivative of morpholine at such temperature that complete solution is effected.
  • morpholine or a suitable derivative of morpholine When the temperature of the mixture is reduced, a separation of the liquid into a two-layer. system will take place.
  • One layer will contain a relatively small amount of the solvent dissolved in the paraffinic portion of the oil. This is called raffinate.
  • the other layer will con.- tain the more naphthenic portion of the oil dissolved in the major quantity of the solvent. This is called the, extract, Thisprocedure may be conducted batchwise or counter-currently.
  • separation of the solvent from the oil may be effected by any one of a number of methods such as distillation, extraction with water and sulfuric acid, or precipitation with carbon dioxide or a carbon dioxide-containing gas.
  • the two layers formed as a result of the extraction operation are of course, separated prior to the removal of the solvent. This separation may be tion of the two layers by decantation.
  • the yield of rafiinate was 52% by volume.
  • the solvent was removed from both the raffinate and extract by distillation at room temperature. Tests on the original oil, raifinate and extract are all shown in Table III.
  • Example 2.100 parts by volume of the same lubricating stock was treated with four successive portions of 50 parts by volume of morpholine.
  • the extract was decanted before mixture of the raflinate with each successive portion of morpholine.
  • Each batch of solvent was mixed with the oil at a temperature of 180 F. and allowed to cool to approximately 80 F.
  • the two layers were separated by decantation and the morpholine separated from both the rafiinate and the extract by distillation at atmospheric pressure.
  • the yield of rafiinate was 67% by volume. Tests on both the raffinate and the extract are shown in Table II. 7
  • Example 3 100 parts by'volume of 300 vis.
  • the 20 mixture was first heated to a temperature of 140 TABLE III- Cntmued F. and then allowed to cool to 120 F. whereupon a two-layer system was formed. Cooling was Orlgmaloil Raffillate continued to approximately F. and the two D 111 b'l't 130 F 220 1620 layers then separated by decantatlon.
  • morpholine may be readily separated from oil at ordinary temperature by first contacting the morpholine with carbon dioxide, forming a solid carbamate which may be easily separated by filtration. Both the carbon dioxide and morpholine may be recovered as such by simply heating the solid carbamate to a temperature of ap-' proximately 200 F. 7
  • process which comprises separating an oil con-' taining paraffinic and naphthenic hydrocarbons into fractions respectively higher in paraflinic and naphthenic compounds by extracting said oil with compounds selected from the group consisting of morpholine and its derivatives.
  • the process which comprises adding compounds selected from the group consisting of morpholine and its derivatives to an oil containing parafiinic and naphthenic hydrocarbons, heating the mixture to such temperature as to effect solution, cooling the solution to form fractions respectively higher in parafiinic and naphthenic compounds and separating the two fractions.
  • the process which comprises adding compounds selected from the group consisting of morpholine and alkyl derivatives of morpholine to an oil containing paraffinic and naphthenic hydrocarbons, heating the mixture to such temperature as to effect solution, cooling the solution to form fractions respectively higher in par-afiinic and naphthenic compounds, removing the fraction rich in naphthenic compounds and similarly retreating the fraction rich in parafiinic compounds with said solvent.
  • the process of producing a more parafiinic lubricating oil from a base oil of lesser paraflinicity which comprises bringing the oil into contact with compounds selected from the group consisting of morpholine and alkyl derivatives of morpholine, thereby partially dissolving the oil, separating the solution of oil so treated into fractions respectively more paraflinic and less par-aiiinic and removing the solvent from the treated oil.
  • the process which comprises bringing mineral oil containing paraffinic and naphthenic hydrocarbons into contact with compounds selected from the group consisting of morpholine and alkyl derivatives of morpholine, thereby effecting solution in the solvent of a portion relatively higher in naphthenic hydrocarbons, separating the solution so formed from the remainder of the oil and removing the solvent from both portions of the oil, thereby obtaining fraction-s of the oil respectively of higher paraffinic and naphthenic hydrocarbon content.
  • the process which comprises separating an oil containing parafiinic and naphthenic hydrocarbons into fractions respectively more paraffinic and more naphthenic than the original oil by extracting said oil with morpholine.
  • the method of increasing the viscosity index of mineral lubricating oil distillate comprising extracting the oil with compounds of the group consisting of morpholine and alkyl derivatives of morpholine whereby to separate fractions of respectively higher and lower viscosity index.
  • the method of increasing the viscosity index of mineral lubricating oil comprising extracting the oil with compounds selected from the group consisting of morpholine and derivatives thereof in which hydrogen is replaced by alkyl groups whereby to separate fractions of respectively higher and lower viscosity index.
  • the process which comprises separating an oil containing paraflinic and non-paraflinic hydrocarbons into fractions respectively higher in paraflinic and non-paraffinic compounds by extracting said oil with solvent containing one or more compounds selected from the group consisting of morpholine and its derivatives.

Description

Patented Aug. 5, 1941 UNITED stares PATENT OFFICE 4 2,251,773 ARBDN Meyer S. Agruss, Chicago, and Wesley H. Sowers,
Flossmoor, Ill., assignors to The Pure Oil Company, Chicago, 111., a corporation of Ohio No Drawing. Application January 12,1939,
Serial N0. 250,500
21 Claims.
This invention relates to extraction methods of refining mineral oils and has particular reference to methods for extracting such oils by means of solvents whereby fractions of different chemical composition though of the same distillation range, are obtained.
It is well known in the art that mineral oils such as petroleum comprise essentially a mixture of various groups or homologous series of compounds such, for example, as paraffins, olefins, hydroaromatics, polymethylenes and other series of compounds of chain and/or ring structure and in which the hydrogen to carbon ratio is less than in the aforementioned series. Crude petroleum oils are generally classified into three types, namely, paraffinic, naphthenic and mixed base, which contain the various series of. hydrocarbons mentioned heretofore, in varyingpropcrtions. ,Probably the best known exam.-
ple of a parafiinic base crude oil is one obtained diate between the paraflinic and naphthenic base type crude oils. The parafiinic type crude oils and their. distillatesmay be distinguished from the naphthenic type crude oils and their distillates by certain arbitrary constants used extensively in the oil refining industry.
The first of these constants is known as the viscosity index and is a coefficient based on the change of viscosity with temperature. This is described by Dean and Davis, Chemical and Metallurgical Engineering, vol. 36, page 618, 1929.
The second of the constants referred to is the viscosity-gravity constant. This is a constant expressing a relation between viscosity and specific gravity and is described by Hill and Coates in Industrial and Engineering Chemistry, vol 20, page 641. V
The more paraffinic oils are characterized by relatively lower viscosity-gravity constants and relatively higher viscosity indices, while the more naphthenic oils are characterized by higher viscosity-gravity constants and lower viscosity indices.
An object of the invention is to provide a method for separating viscous mineral oils into fractions by means of solvents.
Another object of the invention is to provide a method ,for increasing the parafiinicity of min.- eral lubricating oils,
Still another object of the invention is to provide a new extracting agent for separating viscous mineral oils into paraffinic and naphthenic fractions.
' Other objects of the invention will be apparent from the following description.
We have now found that oils containing both parafiinic and various naphthenic. hydrocarbons may be fractionally extracted with a selective solvent such as morpholine (tetrahydroparoxazine) and derivatives thereof such as those derivatives in which one or more hydrogen atoms in the morpholine molecule is substituted by alkyl groups. As examples of such derivatives may be mentioned ethyl tetrahydroparoxazine, l methyl tetrahydroparoxazine, 1 butyl tetrahydroparoxazine and others. The various series of hydrocarbons possess a different solubility in such solvent, the naphthenic hydrocarbons being much more soluble therein than the parafiinic hydrocarbons. When mineral oil containing both series of hydrocarbons is extracted with a solvent of the class above set forth, it is possible to effect a partial separation of the parafiinic from the .naphthenic hydrocarbons and to obtain a fraction which is more parafiinic than the original oil and one which is more naphthenic. For example, from an oil of the mixed base type such as is frequently found in the Mid-Continent area it is possible to produce an oil of a more paraffinic type such as is generally found in the Pennsylvania oil fields. However, regardless of the source, it is possible to obtain by our process oils which are respectively more parafiinic and more naphthenic than the oils normally obtained from such source by distillation.
In accordance with our invention, the oil to be treated is first mixed with morpholine or a suitable derivative of morpholine at such temperature that complete solution is effected. When the temperature of the mixture is reduced, a separation of the liquid into a two-layer. system will take place. One layer will contain a relatively small amount of the solvent dissolved in the paraffinic portion of the oil. This is called raffinate. The other layer will con.- tain the more naphthenic portion of the oil dissolved in the major quantity of the solvent. This is called the, extract, Thisprocedure may be conducted batchwise or counter-currently. After the extraction, separation of the solvent from the oil may be effected by any one of a number of methods such as distillation, extraction with water and sulfuric acid, or precipitation with carbon dioxide or a carbon dioxide-containing gas. The two layers formed as a result of the extraction operation are of course, separated prior to the removal of the solvent. This separation may be tion of the two layers by decantation. The yield of rafiinate was 52% by volume. The solvent was removed from both the raffinate and extract by distillation at room temperature. Tests on the original oil, raifinate and extract are all shown in Table III.
Example 2.100 parts by volume of the same lubricating stock was treated with four successive portions of 50 parts by volume of morpholine.
The extract was decanted before mixture of the raflinate with each successive portion of morpholine. Each batch of solvent was mixed with the oil at a temperature of 180 F. and allowed to cool to approximately 80 F. The two layers were separated by decantation and the morpholine separated from both the rafiinate and the extract by distillation at atmospheric pressure. The yield of rafiinate was 67% by volume. Tests on both the raffinate and the extract are shown in Table II. 7
TABLE II Rafilnate Extract Gravity 29. 3 19. 5 Vis./l 216. l, 671 Vis./210 47. l 57. VI; 98 3 VGC .824 .884 Color 2% +7 Percent carbon res 0.01 -0. 07
Example 3. 100 parts by'volume of 300 vis.
Gulf Coast lubricating distillate, the characterisaccomplished by any suitable procedure, for ex- TABLE III ample, by decantation. The extraction step may be repeated any desired number of times, each" Original 011 Raffinate Extract extraction producing an oil of higher paraffinicity, as may be evidenced by its higher viscosity. 2 4, 6,4 index. Dewaxing may be effected either prior 380 385 375 420 425 430 or subsequent to the extraction procedure. 307,3 249,2 405.0 The invention will be more clearly understood 1s 50 -10 from the following specific examples. .887 .855 .916 Example 1.100 parts by volume of a lubricat- 3 ing distillate obtained from a Mid-Continent oil, 003 0.01 ::I:: the characteristics of which are given in Table I, Was extracted three successive times with 100 (B below) parts by volume of commercial morpholine. The 20 mixture was first heated to a temperature of 140 TABLE III- Cntmued F. and then allowed to cool to 120 F. whereupon a two-layer system was formed. Cooling was Orlgmaloil Raffillate continued to approximately F. and the two D 111 b'l't 130 F 220 1620 layers then separated by decantatlon. The sol 25 gfi zl hl g 1620 1620 vent was removed from the two layers by WaSh- Steam emulsion No 154 68 ing with water, which was followed by a wash of 2% sulfuric acid and then a final water wash. A Tests after BrowmBovenageing 52% yield by volume of rafiinate fraction was obtained. Tests on the original oil and the 30 o 1 11 R fli t raffinate fraction are tabulated below: g 0 a m e TABLE I Sludge (mgms./20O cc. oil); 11.
Acid N0 0.50. 0.05. Corrosion of copp str Positive Negative. Original i R ffi t 35 Steam jet test 25 minutes.. fiminutes.
20.7 31.4 From the foregoing data it is obvious that exig g 221 traction of an oil with morpholine provides an 73 101 efiicient means of separating the oil into fractions 3% l-gig {U which are respectively more paraffinic and more NPA color +4 2/2 naphthenic than the original oil. By repetition of the extraction process upon the rafiinate fractity of solvent to be used and the method of separating the solvent from the oil may varyconsiderably, depending upon the stock being treated and the equipment available with which to carry out the process but in general the ratio of solvent to oil will range from 1 to 5 parts of solvent by volume to 1 part of'oil and the temperature of extraction from 125 F. to 200 F. Separation of the solvent and oil into two distinct phases generally occurs at about F. but this may vary greatly depending on the nature of the stock being treated.
In addition to the methods of separating the solvent from the oil described in the specific examples, morpholine may be readily separated from oil at ordinary temperature by first contacting the morpholine with carbon dioxide, forming a solid carbamate which may be easily separated by filtration. Both the carbon dioxide and morpholine may be recovered as such by simply heating the solid carbamate to a temperature of ap-' proximately 200 F. 7
1 It will also be noted from the data in Example 3 that treatment of a 300 vis. Gulf Coast, oil with morpholine produces a rafiinate suitable as a high quality turbine oil. The sludging characteristics as shown by the Brown-Boveri test are commensurate with high quality turbine o ils commercially available. A consider-able improvement in the carbon residue and color of the rafiinate is obtained which adds materially to the desirable properties of oils treated by our method.
While the foregoing examples show the use of morpholine as -a selective solvent for hydrocarbon oils, derivatives of morpholine, particularly those in which the hydrogen is replaced by an alkyl group, may also be suitably employed alone or mixed with each other or with morpholine. The process is applicable to oils from all types of crude.
We claim:
1. In the solvent refining of mineral oils, the
process which comprises separating an oil con-' taining paraffinic and naphthenic hydrocarbons into fractions respectively higher in paraflinic and naphthenic compounds by extracting said oil with compounds selected from the group consisting of morpholine and its derivatives.
2. In the solvent refining of mineral oils, the process which comprises adding compounds selected from the group consisting of morpholine and its derivatives to an oil containing parafiinic and naphthenic hydrocarbons, heating the mixture to such temperature as to effect solution, cooling the solution to form fractions respectively higher in parafiinic and naphthenic compounds and separating the two fractions.
3. Process in accordance with claim 2 where the added compound is morpholine.
4. In the solvent refining of mineral oils, the process which comprises adding compounds selected from the group consisting of morpholine and alkyl derivatives of morpholine to an oil containing paraffinic and naphthenic hydrocarbons, heating the mixture to such temperature as to effect solution, cooling the solution to form fractions respectively higher in par-afiinic and naphthenic compounds, removing the fraction rich in naphthenic compounds and similarly retreating the fraction rich in parafiinic compounds with said solvent.
5. Process in accordance with claim 4 where the added compound is morpholine.
6. In the solvent refining of mineral oils, the process of producing a more parafiinic lubricating oil from a base oil of lesser paraflinicity which comprises bringing the oil into contact with compounds selected from the group consisting of morpholine and alkyl derivatives of morpholine, thereby partially dissolving the oil, separating the solution of oil so treated into fractions respectively more paraflinic and less par-aiiinic and removing the solvent from the treated oil.
7. Process in accordance with claim 6 where the compound is morpholine.
8. In the solvent refining of mineral oils, the process which comprises bringing mineral oil containing paraffinic and naphthenic hydrocarbons into contact with compounds selected from the group consisting of morpholine and alkyl derivatives of morpholine, thereby effecting solution in the solvent of a portion relatively higher in naphthenic hydrocarbons, separating the solution so formed from the remainder of the oil and removing the solvent from both portions of the oil, thereby obtaining fraction-s of the oil respectively of higher paraffinic and naphthenic hydrocarbon content.
9. Process in accordance with claim 8 where the oil is brought into contact with morpholine.
10. Process in accordance with claim 8 where the solvent is removed from both portions of the oil by distillation.
11. Process in accordance with claim 8 whereby the solvent is removed from both portions of the oil by reacting the solvent with carbon dioxide or a carbon dioxide-containing gas whereby a substantially insoluble product is formed.
12. In the solvent refining of mineral oils, the process which comprises separating an oil containing parafiinic and naphthenic hydrocarbons into fractions respectively more paraffinic and more naphthenic than the original oil by extracting said oil with morpholine.
13. Process in accordance with claim 12 where the morpholine is removed from both fractions by distillation.
14. Process in accordance with claim 12 where the morpholine is removed from both fractions by contacting the fractions with carbon dioxide or carbon dioxide containing gas whereby relatively solid insoluble compounds are formed.
15. In the solvent refining of mineral oils, the method of increasing the viscosity index of mineral lubricating oil distillate comprising extracting the oil with compounds of the group consisting of morpholine and alkyl derivatives of morpholine whereby to separate fractions of respectively higher and lower viscosity index.
16. Method in accordance with claim 15 Where the compound is morpholine.
17. In the solvent refining of mineral oils, the method of increasing the viscosity index of mineral lubricating oil comprising extracting the oil with compounds selected from the group consisting of morpholine and derivatives thereof in which hydrogen is replaced by alkyl groups whereby to separate fractions of respectively higher and lower viscosity index.
18. Method in accordance with claim 17 where the compound is ethyl tetrahydroparoxazine.
19. Method in accordance with claim 17 where the compound is l butyl tetrahydroparoxazine.
20. In the solvent refining of hydrocarbon oils, the process which comprises separating an oil containing paraflinic and non-paraflinic hydrocarbons into fractions respectively higher in paraflinic and non-paraffinic compounds by extracting said oil with solvent containing one or more compounds selected from the group consisting of morpholine and its derivatives.
21. Process in accordance with claim 20 where the solvent contains morpholine.
MEYER S. AGRUSS. WESLEY H. SOWERS.
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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3262875A (en) * 1961-06-07 1966-07-26 Snam Societa Per Azioni Process for extracting high-purity aromatic hydrocarbons from a hydrocarbonaceous mixture
US4909927A (en) * 1985-12-31 1990-03-20 Exxon Research And Engineering Company Extraction of hydrocarbon oils using a combination polar extraction solvent-aliphatic-aromatic or polar extraction solvent-polar substituted naphthenes extraction solvent mixture

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3262875A (en) * 1961-06-07 1966-07-26 Snam Societa Per Azioni Process for extracting high-purity aromatic hydrocarbons from a hydrocarbonaceous mixture
US4909927A (en) * 1985-12-31 1990-03-20 Exxon Research And Engineering Company Extraction of hydrocarbon oils using a combination polar extraction solvent-aliphatic-aromatic or polar extraction solvent-polar substituted naphthenes extraction solvent mixture

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