US2666794A - Desulfurization of hydrocarbons by extraction with phenylacetonitrile - Google Patents
Desulfurization of hydrocarbons by extraction with phenylacetonitrile Download PDFInfo
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- US2666794A US2666794A US230527A US23052751A US2666794A US 2666794 A US2666794 A US 2666794A US 230527 A US230527 A US 230527A US 23052751 A US23052751 A US 23052751A US 2666794 A US2666794 A US 2666794A
- Authority
- US
- United States
- Prior art keywords
- phenylacetonitrile
- disulfide
- hydrocarbon
- solvent
- extract
- 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
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- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 title claims description 91
- 229930195733 hydrocarbon Natural products 0.000 title claims description 31
- 150000002430 hydrocarbons Chemical class 0.000 title claims description 31
- 238000000605 extraction Methods 0.000 title description 7
- 238000006477 desulfuration reaction Methods 0.000 title 1
- 230000023556 desulfurization Effects 0.000 title 1
- 239000004215 Carbon black (E152) Substances 0.000 claims description 19
- 150000003464 sulfur compounds Chemical class 0.000 claims description 11
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 34
- 239000002904 solvent Substances 0.000 description 31
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 27
- 238000000034 method Methods 0.000 description 25
- 239000012071 phase Substances 0.000 description 12
- 238000009835 boiling Methods 0.000 description 10
- 239000012141 concentrate Substances 0.000 description 9
- 239000007788 liquid Substances 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- -1 aliphatic disulfides Chemical class 0.000 description 4
- 229930195734 saturated hydrocarbon Natural products 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 238000000895 extractive distillation Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 150000002019 disulfides Chemical class 0.000 description 2
- 239000002044 hexane fraction Substances 0.000 description 2
- WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 description 1
- 101100128633 Mus musculus Lpin1 gene Proteins 0.000 description 1
- 125000003047 N-acetyl group Chemical group 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 241001208007 Procas Species 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- KHDOTPVDSFBNMG-UHFFFAOYSA-N ethanol;pyridine Chemical compound CCO.C1=CC=NC=C1 KHDOTPVDSFBNMG-UHFFFAOYSA-N 0.000 description 1
- ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000002023 wood 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
Definitions
- This invention relates to the separation of sulfur compounds and hydrocarbons from mixtures of them. In one of its aspects the invention relates to the removal of sulfur compounds from hydrocarbons. In another aspect the invention is concerned with the extraction of aliphatic disulfides from hydrocarbons. In still another of its aspects the invention relates to a process for the selectiveextraction of sulfur compounds from paraf fin-ic and naphthenic hydrocarbons containing them, employing an agent novel for this purpose.
- n-Capromtnle i. Completely miscible with both parafiins and disulfides. Di-nprcpylanllme. Do. '2-ethanolpyrld1nc. Immiscible with disulfide. 4*ethanolpyridine. Do. Ethyl cyanoacetate. Do. Ethylene cyanohydrl Do. Ethylene gl oln m Do. Heptacosafluorotrl-n-butyl Do.
- 3t El-hyagent is :employedin a .liquiddiquid extraction process or in an extractive distillation procass I and is phenylacetonitrile.
- iPhenylace'tonitrile hasa great selectivity for aliphatic disulfidesain the presence of hydrocarbons.
- FIG. 1 A-schematic flow diagram of a' typicaliliquidliquid extraction process .using phenylacetonitrile is givenin Figure'l.
- Tlie mixture-i con- 'tacted with the' primarysolve'nt henylacetoni- -carbons saturated with phenylacetonitrile is vent.
- the extract from unit I which is phenylacetonitrile containing dissolved disulfide concentrate, is contacted with a secondary solvent, which may be a light alkylate, in unit III.
- a secondary solvent which may be a light alkylate
- the secondary solvent and disulfide concentrate from unit III are separated in unit IV. Some of the disulfide concentrate from unit IV is returned to unit I as enriching liquid, and the remainder is sent to product storage. The secondary solvent from unit IV along with some make-up solvent is returned to unit III. The primary sol vent from unit III which is saturated with secondary solvent is processed in unit V.
- the phenylacetonitrile extract from unit I is contacted in unit III with the secondary solvent, which may be a light alkylate with a boiling range of 100 to 300 F. and preferably a narrower boiling range such as 210 to 240 F., or a hexane fraction with a boiling range such as 122 to 156 F.
- the secondary solvent which may be a light alkylate with a boiling range of 100 to 300 F. and preferably a narrower boiling range such as 210 to 240 F., or a hexane fraction with a boiling range such as 122 to 156 F.
- the disulfide concentrate is extracted from the phenylacetonitrile by the light alkylate.
- the disulfide concentrate and light alkylate are separated in a stripper, unit IV; 297 pounds of disulfide concentrate per thousand pounds of feed are returned to the contactor as enriching liquid, and theremainder, 14 pounds, is sent to product storage; the light alkylate is returned to unit III.
- the phenylacetonitrile from unit III which is saturated with light alkylate is processed in unit V. In unit V the light alkylate is stripped out of the phenylacetonitrile. The phenylacetonitrile is returned to unit I and the light alkylate is returned to unit III.
- said saturated hydrocarbon is an aliphatic hydro-- References Cited in the file of this patent UNITED STATES PATENTS Number Name Date 2,069,329 Roelfsema Feb. 2, 1937 2,114,852 McKittrick Apr. 19, 1938 2,162,963 McKittrick June 20, 1939
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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)
Description
Weightpercent, u I I Patented Jan. 19, 1954,
DESULF'URIZATION OF HYDROCARBONS BY EXTRAGTION WITH PHENYLACETO- NITRILE Nor-wood K. Talbert, Yorklyn, Del., assignor to Phillips Petroleum Company, a corporation of Delaware Application June 8, 1951, Serial No. 2.30.521
16 Claims. (01. 260-608) This invention relates to the separation of sulfur compounds and hydrocarbons from mixtures of them. In one of its aspects the invention relates to the removal of sulfur compounds from hydrocarbons. In another aspect the invention is concerned with the extraction of aliphatic disulfides from hydrocarbons. In still another of its aspects the invention relates to a process for the selectiveextraction of sulfur compounds from paraf fin-ic and naphthenic hydrocarbons containing them, employing an agent novel for this purpose.
It is generally impossilole to separatealiphatic sulfur compounds from'h fractional distillation because. the sulfur compounds have boiling points within the boiling ranges of valuable hydrocarbons-contained in the fraction, and, in some cases at least, azeotropes' are formed.
Methods now employed for separating atl'east a portion of the sulfur'compounds from hydro carbons are solvent extraction and extractive distillation, using polar compounds which are preferential solvents for the sulfur compounds. Most of these solvents are unsatisfactory because they either have low aliphatic disulfide solubility or they are miscible with hydrocarbons; or, at hestrtheyhave limited. selectivity tor alip ati disulfid s.
A tabulation of a number-of; solvents. and the reasons. why each is notisatisfactory for the removal of aliphatic disulfides from hydrocarbons isgiven in Table I. Ditertiaryoctyldisulfide was used as; the representative of aliphatic disulfides, and normal heptane was used. asrthe respxesenf'tative o1: parann'hydrqcarpons; f-addition to the. tabulationfgivenf in'IablefL, I have. obtained data which sh ws the. system. ;benzonitrile=di- -;t.ertiaryeo yldisulfide iwas completely miscible *sbove approximately SMF; 'rorconcentration of disulfide from 31.5 weight per'llgentf'jto 159,7
'drocarbon mixtures by TABLEI Solvents tested for disulfidcwparafiin separation 'Solvent Remarks n-Acetyl ethanolanfine Immiscible with disulfide. o-Anisidinc Low selectivity for disulflde with V respect to par-afiins.
n-Buty'romtnle Completely miscible with both 1 parafflns and aromatics.
n-Capromtnle. i. Completely miscible with both parafiins and disulfides. Di-nprcpylanllme. Do. '2-ethanolpyrld1nc. Immiscible with disulfide. 4*ethanolpyridine. Do. Ethyl cyanoacetate. Do. Ethylene cyanohydrl Do. Ethylene gl oln m Do. Heptacosafluorotrl-n-butyl Do.
amine. B-hydroxyethyl acetate... Do. B-hydroxyethylamlmc.. Do. Levuliuic acid. Do. Methyl acetoacetate. Do. Methyl levulmata.-- :Do. Monoethanolarmne" Do. .o-Nitroanisolc n Low selectivity for disulfidc with 1 i respect to' plaralfips. Propylene glycol .i immiscible w th dlsulfidc.
3t El-hyagent is :employedin a .liquiddiquid extraction process or in an extractive distillation procass I and is phenylacetonitrile. iPhenylace'tonitrile hasa great selectivity for aliphatic disulfidesain the presence of hydrocarbons.
A-schematic flow diagram of a' typicaliliquidliquid extraction process .using phenylacetonitrile is giveninFigure'l. "In-this-process:acd-iw wsulflde para'ifin mixture :is processed to produce 4 1a maraffin hydrocarbon :product which is consentially freeilfrom disulfides. ,Tlie mixture-iis con- 'tacted with the' primarysolve'nt henylacetoni- -carbons saturated with phenylacetonitrile is vent. The extract from unit I, which is phenylacetonitrile containing dissolved disulfide concentrate, is contacted with a secondary solvent, which may be a light alkylate, in unit III. The secondary solvent and disulfide concentrate from unit III are separated in unit IV. Some of the disulfide concentrate from unit IV is returned to unit I as enriching liquid, and the remainder is sent to product storage. The secondary solvent from unit IV along with some make-up solvent is returned to unit III. The primary sol vent from unit III which is saturated with secondary solvent is processed in unit V. The pri- TABLE II Liquid-liquid equilibrium relationships for the system phenylacetonitrile ditertiaryoctyldisulfide-normal heptane TEMPERATURE: 71 F. [Equilibriumconcentrations are given in weight percent] Hydrocarbon-rich phase Solvent-rich phase K m4 ]fide n-Hep- Nisulfide e t nl'mlc Dimo Nisulfide e t mtrlle Di- EC R61 tane trile 01v. Weight m sulfide 7 trile (solv. weight 110 m sulfide 7 K s free) free) 0 93. 6. 5 0 0.070 0 11. 1 88. 9 0 8.00 0.12 7 1. 0 92. 2 6. 8 1.1 073 3.1 11.1 85. 8 21. 8 6. 04 3.1 0.12 26 3. 5 89. 2 7. 3 3. 8 .079 5. 8 11. 1 83.1 34.3 4. 92 1. 7 0.12 14 3 8. 0 84. 1 7. 9 8.7 086 10. 2 11. 1 78. 7 47. 9 3. 69 l. 3 0. 13 12.5 79. 1 8. 4 13. 7 092 14. 1 11.2 74. 7 55. 8 2. 96 1. 1 0. 14 8 Z 18. 2 72. 5 9.3 20. 1 103 20. 0 12.0 68. 0 61. 5 2. 12 l. l 0. 17 7 23. 5 66. 5 l0. 0 26.1 .111 23. 9 12.8 63. 3 65. 1 l. 73 1.0 0.19 5 35.0 51. 1 l3. 9 40. 7 163 35.0 16. 0 49. 0 68. 7 0. 96 1. 0 0. 13 3 K for disulfide. 1 K K for n-heptane. 3 Based on estimated tie lines.
I TABLE III Estimated liquid-liquid equilibrium relationships for the system phenylacetonitrile-ditertiary- 0ctyZdisulfide-cyclohercane TEMPERATURE: 77 F [Equilibrium concentrations are given in weight percent] Hydrocarbon-rich phase Solvent-rich phase K p c 1 fii i i ht nitrile D 1 iifi w m n '1 m 1 ML y 0- e lsu e w su flde hexane Nltnle (solv. w i HO n fide Cy Nimle (solv. w i HQ mixt fid oycu K free) free) K for disulfide Above values are based on estimated tie lines. mary solvent recovered in unit V along with some make-up solvent is returned to unit I, and the recovered secondary solvent is returned to unit III.
The liquid-liquid equilibrium relationships for 'the phenylacetom'trile ditertiaryoctyldisulfidenormal heptane system at 77 F. have been determined, and the compositions of the coexisting equilibrium phases are presented in Table II. Values of relative K are included in this table. The relative K is indicative of the selectivity of a solvent for a given compound in the presence of one or more other compounds. A compound -pounds have boiling points within the boiling ranges of valuable hydrocarbons contained in the fraction.
Detailed information concerning the phenylacetonitrile process for the removal of ditertiaryoctyldisulfide tflomynormal-zheptaneeisjLgiveniin =Fig'urezb2. ';EEhe;.-contactor, unit.I,-.:'i "provided with:trays;V risers; rand iiownecomers in eldel 'ifi) obtain intimate: contacting. of. :the hydrocarbon aphasewith phenylacetonitrile. Any: other suitablegmeans of contacting the hydrocarbon-phase with the solvent could have been used. i'I-he basis oft-he schematic 'flow diagram :(Eigurer 2) .is illiOOpounds fof hydrocarbon feed. "Ihe deedis a. binary mixture; :of normal heptane and =diteritiaryoctyldisulfide :containing 7 l .flvweightper cent disulfide, The disulfide concentrationvpfathe normalzheptane is :reduced; to 0.1 per cent by extraction with phenylacetonitrile. As the disulfide concentrate contains 565: fiweig-ht perlcent disulfide, the normal heptane loss-in this stream is only pounds per 1000 pounds of feed. The ,liquid-jliquid contactor has three theoretical rected to unit II, which is a stripping column,
wherein the normal heptane and phenylacetonitrile are separated. The phenylacetonitrile is returned to unit I, and the normal heptane, which is essentially free of disulfide, is directed to product storage. The extract from the contactor is processed in the hydrocarbon-solvent separation step wherein the operations illustrated by units III, IV and V of Figure 1 are accomplished. The phenylacetonitrile extract from unit I is contacted in unit III with the secondary solvent, which may be a light alkylate with a boiling range of 100 to 300 F. and preferably a narrower boiling range such as 210 to 240 F., or a hexane fraction with a boiling range such as 122 to 156 F. The disulfide concentrate is extracted from the phenylacetonitrile by the light alkylate. The disulfide concentrate and light alkylate are separated in a stripper, unit IV; 297 pounds of disulfide concentrate per thousand pounds of feed are returned to the contactor as enriching liquid, and theremainder, 14 pounds, is sent to product storage; the light alkylate is returned to unit III. The phenylacetonitrile from unit III which is saturated with light alkylate is processed in unit V. In unit V the light alkylate is stripped out of the phenylacetonitrile. The phenylacetonitrile is returned to unit I and the light alkylate is returned to unit III.
Reasonable variation and modification are possible within the scope of the foregoing disclosure, drawings, and appended claims to the invention; the essence of which is that phenylacetonitrile has been found to bean excellent selective solvent agent for the extraction or removal of sulfur compounds from hydrocarbons and that a method for such removal has been set forth as described.
I claim:
1. The removal of a sulfur compound from a hydrocarbon containing it which comprises the step of contacting said hydrocarbon with phenylacetonitrile. I
2. The process of claim 1 wherein a liquid t liquid extraction method is employed.
3. The process of claim 1 wherein an extractive distillation method is employed.
4. The process of claim 1 wherein the temper ature iis maintained in tnerang' SOP-FI to ELO'O F.
5. The removalbf an aliphatic disulfide from a hydrocarbon by contacting said T hydr'ocaibon with .-.phenylacetonitrile, separating a raffinate containing hydrocarbon and f phenylacetonitrile from ea r. phenylacetonitriledisulfide-containing extracpand then recovering said disulfide from said extract.
The removal of a ditertiaryoctyldisulfide from-a hydrocarbon by contacting said hydrocarbon withphenylacetonitrile, separating arraifinate-containing hydrocarbon "andlphenylacetonitrile f rom a phenylacetonitrile-'disultide-contain-ing- 1 extract and then recovering said 'disulfide-rromsai'd extract.
7 ."Iitie remcv' l or a ditertiaryoctyldisulfide from n-hepta'ne' by contacting said n-heptane with phenylacetonitrile, separating a rafiina'te containing n'-heptaiie and phenylacetonitrile from I a phenylacetonitrile-disuIfide-contaifiifi extract. ana' tnea iec'dvenng said disulfide" from said extract.
8. The process for the separation of an aliphatic disulfied from a substantially saturated hydrocarbon containing it which comprises contacting said hydrocarbon with a primary solvent essentially phenylacetonitrile, separating from the contacted admixture, thus obtained, a ramnate containing hydrocarbon and phenylacetonitrile, separating phenylacetonitrile from the rafilnate, separating a hydrocarbon fraction, essentially free irom disulfide, as a product of the process, returning the phenylacetonitrile to the contacting step of the process, separating from the said contacted admixture an extract rich in disulfide, treating said extract with a secondary solvent to extract disulfide therefrom, separating disulfide from said secondary solvent as another product of the process, recovering phenylacetonitrile from said solvent and reusing both the last recovered phenylacetonitrile and secondary solvent in the process as before.
9. The process for the separation of ditertiaryoctyldisulfide from a heptane containing it which comprises contacting said heptane with a primary solvent essentially phenylacetonitrile, separating from the contacted admixture, thus obtained, a raffinate containing heptane and phenylacetonitrile, separating phenylacetonitrile from the raiiinate, separating a heptane fraction, essentially free from disulfide, as a product of the process, returning the phenylacetonitrile to the contacting step of the process, separating from the said contacted admixture an extract rich in disulfide, treating said extract with a secondary solvent to extract disulfide therefrom, separating disulfide from said secondary solvent as another product of the process, recovering phenylacetonitrile from said solvent and reusing both the last recovered phenylacetonitrile and secondary solvent in the process as before.
10. The recovery of ditertiaryoctyldisulfide from normal heptane which comprises contacting the normal heptane containing said disulfide with phenylacetonitrile in the liquid phase, separating saidcontacted admixture into raffinate and extract phases, said raffinate phase containing normal heptane and phenylacetonitrile, separating normal heptane from phenylacetonitrile as a product of the process and returning said separated phenylacetonitrileto the contacting step, contacting the said extract phase containing phenylacetonitrile and disulfide with a light hydrocarbon alkylate boiling in the range of to 300 F. thus separating a disulfide concentrate from the phenylacetonitrile, then separating the disulfide concentrate from the light alkylate and removing disulfide as a product of the process while returning some disulfide as enriching liquid to the contacting step, returning the alkylate to the step in which the extract phase is contacted with light alkylate, and returning the phenylacetonitrile to the first mentioned contacting step.
11. The process of claim 10 wherein the light alkylate has a boiling range of from 210 to 240 F.
12. The process of claim 10 wherein the light alkylate is essentially a hexane fraction boiling within the approximat range 122 to 156 F.
18. The process of claim 10 wherein the temperature during the contact of the phenylacetonitrile and the heptane is maintained at approximately 7 7 F.
14. The removal of sulfur compounds from a saturated hydrocarbon with phenylacetonitrile which comprises contacting said saturated hydrocarbon with phenylacetonitrile to obtain an extract phase and a raffinate phase, separating a ratfinate containing said hydrocarbon and phenylacetonitrile from a phenylacetonitrile-su1fur compound containing extract and then recovering said sulfur compound from said extract.
15. A process according to claim 14 wherein. said saturated hydrocarbon is an aliphatic hydro-- References Cited in the file of this patent UNITED STATES PATENTS Number Name Date 2,069,329 Roelfsema Feb. 2, 1937 2,114,852 McKittrick Apr. 19, 1938 2,162,963 McKittrick June 20, 1939
Claims (1)
1. THE REMOVAL OF A SULFUR COMPOUND FROM A HYDROCARBON CONTAINING IT WHICH COMPRISES THE STEP OF CONTACTING SAID HYDROCARBON WITH PHENYLACETONITRILE.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US230527A US2666794A (en) | 1951-06-08 | 1951-06-08 | Desulfurization of hydrocarbons by extraction with phenylacetonitrile |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US230527A US2666794A (en) | 1951-06-08 | 1951-06-08 | Desulfurization of hydrocarbons by extraction with phenylacetonitrile |
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| Publication Number | Publication Date |
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| US2666794A true US2666794A (en) | 1954-01-19 |
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| US230527A Expired - Lifetime US2666794A (en) | 1951-06-08 | 1951-06-08 | Desulfurization of hydrocarbons by extraction with phenylacetonitrile |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2722500A (en) * | 1954-02-05 | 1955-11-01 | Charles W Rippie | Removal of acidic gases from hydrocarbon gases and liquids |
| US2767119A (en) * | 1955-04-07 | 1956-10-16 | Gen Aniline & Film Corp | Process for decolorizing petroleum hydrocarbons with a pyrrolidone |
| EP0538738A2 (en) * | 1991-10-15 | 1993-04-28 | General Sekiyu Kabushiki Kaisha | Desulfurization and Decolourizing of light oil by extraction |
| CN106336891A (en) * | 2015-07-09 | 2017-01-18 | 中国石油化工股份有限公司 | Composition used for reducing hydrocarbon oil metal content and its application and method for reducing hydrocarbon oil metal content |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2069329A (en) * | 1935-03-20 | 1937-02-02 | Shell Dev | Process of refining oils |
| US2162963A (en) * | 1937-08-28 | 1939-06-20 | Shell Dev | Process for desulphurizing mineral oils |
-
1951
- 1951-06-08 US US230527A patent/US2666794A/en not_active Expired - Lifetime
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2069329A (en) * | 1935-03-20 | 1937-02-02 | Shell Dev | Process of refining oils |
| US2114852A (en) * | 1935-03-20 | 1938-04-19 | Shell Dev | Process for desulphurizing mineral oil distillates |
| US2162963A (en) * | 1937-08-28 | 1939-06-20 | Shell Dev | Process for desulphurizing mineral oils |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2722500A (en) * | 1954-02-05 | 1955-11-01 | Charles W Rippie | Removal of acidic gases from hydrocarbon gases and liquids |
| US2767119A (en) * | 1955-04-07 | 1956-10-16 | Gen Aniline & Film Corp | Process for decolorizing petroleum hydrocarbons with a pyrrolidone |
| EP0538738A2 (en) * | 1991-10-15 | 1993-04-28 | General Sekiyu Kabushiki Kaisha | Desulfurization and Decolourizing of light oil by extraction |
| EP0538738A3 (en) * | 1991-10-15 | 1993-05-12 | General Sekiyu Kabushiki Kaisha | Desulfurization and denitration of light oil by extraction |
| EP0653477A2 (en) * | 1991-10-15 | 1995-05-17 | General Sekiyu Kabushiki Kaisha | Desulfurization and denitration of light oil by extraction |
| EP0653477A3 (en) * | 1991-10-15 | 1995-07-26 | Gen Sekiyu Kabushiki Kaisha | Desulfurization and denitration of light oil by extraction. |
| CN106336891A (en) * | 2015-07-09 | 2017-01-18 | 中国石油化工股份有限公司 | Composition used for reducing hydrocarbon oil metal content and its application and method for reducing hydrocarbon oil metal content |
| CN106336891B (en) * | 2015-07-09 | 2018-08-28 | 中国石油化工股份有限公司 | A method of for reducing the composition of hydrocarbon ils tenor and its application and a kind of reduction hydrocarbon ils tenor |
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