US3661772A - Solvent refining of naphthenic lube oil with n-methyl-2-pyrrolidone - Google Patents
Solvent refining of naphthenic lube oil with n-methyl-2-pyrrolidone Download PDFInfo
- Publication number
- US3661772A US3661772A US25592A US3661772DA US3661772A US 3661772 A US3661772 A US 3661772A US 25592 A US25592 A US 25592A US 3661772D A US3661772D A US 3661772DA US 3661772 A US3661772 A US 3661772A
- Authority
- US
- United States
- Prior art keywords
- lubricating oil
- solvent
- methyl
- naphthenic
- pyrrolidone
- 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 - Lifetime
Links
- 239000010687 lubricating oil Substances 0.000 title abstract description 49
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 title abstract description 16
- 238000007670 refining Methods 0.000 title abstract description 16
- 239000002904 solvent Substances 0.000 title description 43
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 18
- 229910001868 water Inorganic materials 0.000 abstract description 18
- 230000003647 oxidation Effects 0.000 abstract description 12
- 238000007254 oxidation reaction Methods 0.000 abstract description 12
- 238000000638 solvent extraction Methods 0.000 abstract description 10
- 239000000470 constituent Substances 0.000 abstract description 8
- 238000004821 distillation Methods 0.000 abstract description 8
- 238000004519 manufacturing process Methods 0.000 abstract description 8
- 230000001976 improved effect Effects 0.000 abstract description 7
- 239000010779 crude oil Substances 0.000 abstract description 6
- 238000000926 separation method Methods 0.000 abstract description 5
- 230000001050 lubricating effect Effects 0.000 abstract description 3
- 239000003125 aqueous solvent Substances 0.000 abstract description 2
- 239000003921 oil Substances 0.000 description 29
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 10
- 238000000605 extraction Methods 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 239000000463 material Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 238000005260 corrosion Methods 0.000 description 4
- 230000007797 corrosion Effects 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 238000005292 vacuum distillation Methods 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 230000005484 gravity Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 2
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 description 1
- 101100279438 Caenorhabditis elegans egg-3 gene Proteins 0.000 description 1
- 241000543381 Cliftonia monophylla Species 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000010727 cylinder oil Substances 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 239000002195 soluble material Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000010723 turbine oil Substances 0.000 description 1
Classifications
-
- 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
- C10G21/00—Refining of hydrocarbon oils, in the absence of hydrogen, by extraction with selective solvents
Definitions
- This invention is particularly directed to the solvent extraction step in the manufacture of naphthenic lubricating oils by the sequence of distillation, solvent extraction, solvent dewaxing (optional) and blending.
- the solvent extraction in the invention is accomplished with aqueous N-methyl-Z-pyrrolidone at a temperature of at least 50 F. and below the temperature of complete miscibility of the lubricating oil stock in N-methyl-Z-pyrrolidone and at a dosage efiective to dissolve at least 10 volume percent of said lubricating oil stock whereby a refined lubricating oil stock is produced of improved oxidation stability.
- anhydrous and essentially anhydrous, N- methyl-2-pyrrolidone has been known as a solvent for the separation of constituents of low thermal and oxidation stability from lubricating oil fractions and for the separation of low viscosity index constituents from lubricating oil.
- naphthenic oil is the lubricating oil to be refined several unexpectedly undesirable factors arise in the refining process using anhydrous and essentially anhydrous N-methyl-Z-pyrrolidone.
- essentially anhydrous means a water content of zero to less than about 1 wt. percent.
- finished naphthenic lubricating oils are produced from naphthenic base crude oil by vacuum distillation, solvent refining of the vacuum distillate or residual stock with aqueous N-methyl-Z-pyrrolidone as a selective solvent and optionally inhibitor addition.
- solvent refining step by incorporating between about 2 and 15 wt. percent water basis total solvent in the N-methyl-Z- pyrrolidone, undesirable miscibility, increased viscosity and low refined oil yield are avoided.
- the vacuum naphthenic distillate or residual naphthenic lubricating oil stock is contacted with N-methyl-Z-pyrrolidone having a water content of between about 2 and 15 wt. percent, preferably between about 3 and 10 wt. percent, at a temperature of at least 50 F. and below the temperature of complete miscibility of said naphthenic lubricating oil stock in N-methyl-2-pyrrolidone and at a dosage effective to dissolve at least 10 volume percent of said lubricating oil stock.
- the foregoing solvent extraction step produces a refined lubricating oil stock of improved viscosity index, improved thermal stability and improved oxidation stability.
- the manufacture of a merchantable naphthene base lubricating oil does not require dewaxing and only the addition of usual inhibitors is necessary.
- naphthenic oil contemplated herein are oils used in the manufacture of turbine lubricating oils of an SUS viscosity at 100 F. of between about 100 and 600; refrigeration oils of an SUS viscosity at 100 F. of between and 600; and cylinder oils of an SUS viscosity at F. of between 1000 and 4000.
- the viscosity index of naphthenic base lubricanting oil charge stocks is within the range of about -10 to 50 and the viscosity index of the refined lubricating oil stock is at least 10 units higher.
- the extraction temperatures and dosages in refining naphthene oils are advantageously within the range of 50 to 200 F., preferably within the range of 75 to F. and 30 to 300%, and preferably 75 to 200% respective y.
- a typical processing sequence which may be used in the manufacture of lubricating oils in accordance with the process of this invention is crude naphthenic oil is passed to crude distillation facility.
- the crude oil is separated into lower boiling fractions, forexample gas and fuel distillates and gas oils, maximmboiling fraction such as naphthenic lubricating oil distillates and crude residuum.
- the lubricating oil naphthenic distillate and/or naphthenic residual lube stock is passed to aqueous N-methyl-Z-pyrrolidone solvent extraction 4 using N-methyl-Z-pyrrolidone having varying water contents.
- Tables II, HA and Table 11B The conditions and results are set forth below in Tables II, HA and Table 11B:
- the extract and raflinate are sep- Solvegt composition, wei ht perarated and the lube oil raifinate is optionally combined can N-methyl-Z- olidone 100 100 98 with standard corrosion and/or oxidation inhibitors as s lwat 'gir 08 3 5 0 vent osage v0 ume percen 1 3X yvell as the standard detergent dlspersants requlred) Extractiontengpemtmlw no no 1m in a subsequent lube 011 product blend. Raflinate tests:
- This example demonstrates the method of the inven. Extract tests; RI at 70 C 1-5234 1-5162 1-5465 tion and the criticality of using water to modify the solvent power of N-methyl-Z-pyrrolidone' to permit control TABLE HA of refined oil quality and yield.
- a residual 352% Run naphthenic lubricating oil stock is separated from crude Conditions charge I K L 011 byvacuum distillation.
- the naphthen c 011 stock is solvent compositionweight extracted in a l2-stage countercurrent mixer-settler expellizcentrth 1% nd 98 95 95 traction apparatus using N-methyl-Z-pyrrolidone having it ⁇ ;zjfi ff ff ijjjjjj "j 2 5 5 5 varying water contents.
- N-methyl-Z-pyrrolidone 100 100 100 Water 0 0 0 35 golgentidosiage, volltime gerFcenL 15g fig I 1'80 011 6111 a life R Vi t 1 TABLE IIB sees 57, a Unre- Run 8 diti fined M N g 1 12553 316 1 200 Con ons charge oor n Solvent com sition,wei ht ercent:
- Viscosity see at: 100 F 2 020 2 020 Viscosity index- 0 45 41 41 56 10 10 Pour, F 20 20 -20 20 300 750 Extract tests, RI at 70 C 1. 5206 1. 5240 1.5296 1. 5129 1. 4875 1. 4876 2 EXAMPLE IV 0 N-methyl-Z-pyrrolidone.
- This example illustrates the method of the invention EXAMPLE VI and shows that the refined oils exhibit superior color, Thisexamplemustrates t he unexpected aspects of the g3: 2:32: x i gzg xi g gg figgggz 2%?
- the S.0.D. Lead Corrosion Test is a bench test of corrosion resistance Yield Volume Percent 75 49 which is described in Military Specification MILL- 708C, Lubricating Oil, Aircraft Turbine Oil, Synthetic Base, dated November 2, 1955 and is described in detail in U.S. Patent 3,003,963.
- the Heat Test is a bench test for thermal stability in which a 250 milliliter sample of the oil under test is heated for hours at 250 F. and then held at room temperature for 1 day. The sample is then weighed to determine the evaporation loss, the viscosity is determined and compared with the oil before heating, the neutralization number is determined and the presence or absence of sludge is noted.
- EXAMPLE V This example illustrates the advantages of aqueous N-methyl-Z-pyrrolidone over anhydrous furfural refining of naphthenic lubricating oil.
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)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
- Lubricants (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US2559270A | 1970-04-03 | 1970-04-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3661772A true US3661772A (en) | 1972-05-09 |
Family
ID=21826954
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US25592A Expired - Lifetime US3661772A (en) | 1970-04-03 | 1970-04-03 | Solvent refining of naphthenic lube oil with n-methyl-2-pyrrolidone |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3661772A (show.php) |
| CA (1) | CA953234A (show.php) |
| DK (1) | DK128501B (show.php) |
| FR (1) | FR2085825B1 (show.php) |
| GB (1) | GB1286420A (show.php) |
| NL (1) | NL157346B (show.php) |
| SE (1) | SE360671B (show.php) |
| ZA (1) | ZA711975B (show.php) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2221836C1 (ru) * | 2002-07-15 | 2004-01-20 | Общество с ограниченной ответственностью "Производственное объединение "Киришинефтеоргсинтез" | Способ очистки вакуумных газойлей с одновременным получением сырья для производства технического углерода |
-
1970
- 1970-04-03 US US25592A patent/US3661772A/en not_active Expired - Lifetime
-
1971
- 1971-03-26 ZA ZA711975A patent/ZA711975B/xx unknown
- 1971-04-01 NL NL7104342.A patent/NL157346B/xx not_active IP Right Cessation
- 1971-04-02 CA CA109,516A patent/CA953234A/en not_active Expired
- 1971-04-02 FR FR7111696A patent/FR2085825B1/fr not_active Expired
- 1971-04-02 SE SE04320/71A patent/SE360671B/xx unknown
- 1971-04-02 DK DK158071AA patent/DK128501B/da not_active IP Right Cessation
- 1971-04-19 GB GB25190/71A patent/GB1286420A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2221836C1 (ru) * | 2002-07-15 | 2004-01-20 | Общество с ограниченной ответственностью "Производственное объединение "Киришинефтеоргсинтез" | Способ очистки вакуумных газойлей с одновременным получением сырья для производства технического углерода |
Also Published As
| Publication number | Publication date |
|---|---|
| DK128501B (da) | 1974-05-13 |
| NL7104342A (show.php) | 1971-10-05 |
| GB1286420A (en) | 1972-08-23 |
| DE2115762A1 (de) | 1971-10-21 |
| DE2115762B2 (de) | 1976-04-08 |
| SE360671B (show.php) | 1973-10-01 |
| ZA711975B (en) | 1972-08-30 |
| CA953234A (en) | 1974-08-20 |
| FR2085825B1 (show.php) | 1974-03-22 |
| NL157346B (nl) | 1978-07-17 |
| FR2085825A1 (show.php) | 1971-12-31 |
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