DE1075249B - Process for the oxidation of mercaptans !! (Mercaptides) in hydrocarbons to disulfides - Google Patents

Process for the oxidation of mercaptans !! (Mercaptides) in hydrocarbons to disulfides

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Publication number
DE1075249B
DE1075249B DENDAT1075249D DE1075249DA DE1075249B DE 1075249 B DE1075249 B DE 1075249B DE NDAT1075249 D DENDAT1075249 D DE NDAT1075249D DE 1075249D A DE1075249D A DE 1075249DA DE 1075249 B DE1075249 B DE 1075249B
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Prior art keywords
oxidation
mercaptans
disulfides
mercaptides
hydrocarbons
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Pending
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DENDAT1075249D
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German (de)
Inventor
Gonfreville-l'Orcher Seine-Maritime und Dipl.-Ing. Edouard Weisang Lc Havre Dipl.-Ing. Joseph Quiquerez (Frankreich)
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Compagnie Francaise de Raffinage SA
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Compagnie Francaise de Raffinage SA
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Publication of DE1075249B publication Critical patent/DE1075249B/en
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    • C—CHEMISTRY; METALLURGY
    • C22—METALLURGY; FERROUS OR NON-FERROUS ALLOYS; TREATMENT OF ALLOYS OR NON-FERROUS METALS
    • C22B—PRODUCTION AND REFINING OF METALS; PRETREATMENT OF RAW MATERIALS
    • C22B26/00—Obtaining alkali, alkaline earth metals or magnesium
    • C22B26/20—Obtaining alkaline earth metals or magnesium
    • C22B26/22—Obtaining magnesium
    • 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
    • C10G27/00—Refining of hydrocarbon oils in the absence of hydrogen, by oxidation
    • C10G27/04—Refining of hydrocarbon oils in the absence of hydrogen, by oxidation with oxygen or compounds generating oxygen
    • C10G27/10—Refining of hydrocarbon oils in the absence of hydrogen, by oxidation with oxygen or compounds generating oxygen in the presence of metal-containing organic complexes, e.g. chelates, or cationic ion-exchange resins

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Mechanical Engineering (AREA)
  • Manufacturing & Machinery (AREA)
  • Geology (AREA)
  • Materials Engineering (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Metallurgy (AREA)
  • General Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Environmental & Geological Engineering (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)

Description

DEUTSCHESGERMAN

Das Verfahren bezweckt die Raffination von mercaptan- und/oder mercaptidhaltigen Kohlenwasserstoffen und deren Mischungen und besteht in der Überführung derselben in Disulfide.The purpose of the process is to refine mercaptan and / or mercaptid-containing hydrocarbons and their mixtures and consists in converting them into disulfides.

Das Süßen von mercaptan- und/oder mercaptidhaltigen Petroleum-Kohlenwasserstoffen oder ihrer Fraktionen durch Oxydation mittels Sauerstoff oder eines sauerstoffhaltigen Gases in Anwesenheit von Metall-Chelaten, die durch Kondensation eines Iminophenols und einer Verbindung eines Metalls der VIII. Gruppe des Periodischen Systems entstehen, ist bekannt. An Stelle der Chelate können auch Chelatbindungen eingehende Zusammensetzungen verwendet werden.The sweetening of mercaptan and / or mercaptide-containing petroleum hydrocarbons or their fractions by oxidation by means of oxygen or an oxygen-containing gas in the presence of metal chelates which by condensation of an iminophenol and a compound of a metal of Group VIII of the Periodic System is well known. Chelate-forming compositions can also be used in place of the chelates be used.

In den deutschen Patentschriften 832 312, 949 588, 965 795 und 1 042 802 sind solche Raffinationen »saurer« Petroleumprodukte beschrieben.In German patents 832 312, 949 588, 965 795 and 1 042 802, such refinings are "more acidic" Petroleum products described.

Die direkte Anwendung eines solchen \%rfahrens führt zu Nebenreaktionen, die seinen wirtschaftlichen Wert beeinträchtigen. Bei der Oxydation von Mercaptanen (Mercaptiden) kann die Oxydationsstufe des Disulfide überschritten werden, und man erhält stärker oxydierte Produkte. Letztere sind trotz ihrer geringen Menge so instabil, daß sie sich unter normalen Lagerungsbedingungen zersetzen, z. B. in verschiedene, sauer reagierende Stoffe, die unter anderem Harze bilden, die Oxydationsbeständigkeit der Petroleumfraktionen herabsetzen und die Rückbildung geringer Mercaptanmengen bewirken.The direct application of such a procedure leads to side reactions that undermine its economic value. During the oxidation of mercaptans (mercaptides) the oxidation level of the disulphide can be exceeded and more strongly oxidized ones are obtained Products. In spite of their small amount, the latter are so unstable that they become under normal storage conditions decompose, e.g. B. in various, acidic reacting substances that form resins, among other things, reduce the oxidation resistance of the petroleum fractions and cause the regression of small amounts of mercaptan.

Bei vorliegendem Verfahren geschieht die Oxydation von Mercaptanen (Mercaptiden) zu Disulfiden mit Sauerstoff oder sauerstoffhaltigen Gasen in Anwesenheit eines Metall-Chelats, das durch Kondensation eines Iminophenols mit einer Verbindung eines Metalls der VIII. Gruppe erhalten wurde. An Stelle der fertigen Chelatverbindung können auch die unter den angegebenen Temperatur- und Druckbedingungen eine solche Bindung eingehenden Bestandteile verwendet werden.In the present process, mercaptans (mercaptides) are oxidized to disulfides with oxygen or oxygen-containing gases in the presence of a metal chelate formed by condensation of an iminophenol with a compound of a Group VIII metal. In place of the finished chelate compound such a bond can also be achieved under the specified temperature and pressure conditions incoming ingredients are used.

Man kann Nebenreaktionen bei der Oxydation von Mercaptanen (Mercaptiden) zu Disulfiden vermeiden, ebenso die Bildung höherer Oxydationsprodukte, wenn man bei 30° C oder höher bei Atmosphärendruck arbeitet.Side reactions in the oxidation of mercaptans (mercaptides) to disulfides can be avoided, likewise the formation of higher oxidation products when working at 30 ° C. or higher at atmospheric pressure.

Feiner wird eine merkliche Erhöhung der Oxydationsgeschwindigkeit von Mercaptanen (Mercaptiden) zu Disulfiden, d. h. eine Herabsetzung der Süßungszeit, erzielt.A noticeable increase in the rate of oxidation of mercaptans (mercaptides) to disulfides becomes finer, d. H. a reduction in the sweetening time achieved.

Die nachstehenden Beispiele erläutern die Erfindung.The following examples illustrate the invention.

Beispiel 1example 1

Um die Vermeidung der Bildung von höher oxydierten Produkten als Disulfiden zu beweisen, wird tertiäres Butylmercaptan, gelöst in Benzol, oxydiert.To prove the avoidance of the formation of more highly oxidized products than disulfides, tertiary is used Butyl mercaptan dissolved in benzene is oxidized.

Vier Proben von jeweils 11 Benzol, welche 0,410 g tertiäres Butylmercaptan enthalten, werden unter Atmosphärendruck mit reinem Sauerstoff bei 15, 25, 35 und 45° C in Anwesenheit von 0,49 ecm einer Kresollösung von 41 mg Bis-(disalicylaläthylendiimin)-dikobalt-mono-Verfahren zur OxydationFour samples of 11 benzene each containing 0.410 g containing tertiary butyl mercaptan, are under atmospheric pressure with pure oxygen at 15, 25, 35 and 45 ° C in the presence of 0.49 ecm of a cresol solution of 41 mg bis (disalicylalethylenediimine) -dicobalt-mono-method for oxidation

von Mercaptanen (Mercaptiden)of mercaptans (mercaptides)

in Kohlenwasserstoffen zu Disulfidenin hydrocarbons to disulfides

Anmelder:
Compagnie Frangaise de Raffinage, ParisApplicant:
Compagnie Frangaise de Raffinage, Paris

Vertreter: Dipl.-Ing. E. PrinzRepresentative: Dipl.-Ing. E. Prince

und Dr. rer. nat. G. Hauser, Patentanwälte,and Dr. rer. nat. G. Hauser, patent attorneys,

München-Pasing, Bodenseestr. 3 aMunich-Pasing, Bodenseestr. 3 a

Beanspruchte Priorität:
Frankreich vom 10. Mai 1957Claimed priority:
France 10 May 1957

Dipl.-Ing. Joseph Quiquerez,
ao Gonfreville-l'Orcher, Seine-Maritime,Dipl.-Ing. Joseph Quiquerez,
ao Gonfreville-l'Orcher, Seine-Maritime,

und Dipl.-Ing. Edouard Weisang, Le Havreand Dipl.-Ing. Edouard Weisang, Le Havre

(Frankreich),
sind als Erfinder genannt worden(France),
have been named as inventors

hydrat und einer 41 mg Blei entsprechenden Menge Bleikresolat behandelt.hydrate and an amount of lead cresolate equivalent to 41 mg lead.

Tabelle I zeigt, daß beim Arbeiten bei höherer Temperatur die verbrauchte Sauerstoffmenge sich von der theoretisch erforderlichen kaum unterscheidet, d. h., esTable I shows that when working at a higher temperature, the amount of oxygen consumed differs from the theoretically required hardly differs, d. h., it

kommen auf 1 Sauerstoffatom 2 Schwefelatome— = 2).there are 2 sulfur atoms for every 1 oxygen atom - = 2).

Dagegen steigt bei den tiefen Temperaturen der Sauerstoffverbrauch stark über den theoretischen an.On the other hand, oxygen consumption increases at low temperatures strongly over the theoretical.

Tabelle ITable I.

Temperaturen (0C) 15 25 35Temperatures ( 0 C) 15 25 35

Srsh (mg/100 ecm), zu Beginn .. 41 41 41
Sbsh (mg/100 ecm), nachSrsh (mg / 100 ecm), at the beginning .. 41 41 41
Sbsh (mg / 100 ecm), after

360 Minuten 14 6 3360 minutes 14 6 3

Vol. O2 — Theorie (ecm) 4,5 6,1 6,65Vol. O 2 theory (ecm) 4.5 6.1 6.65

Vol. O2 — verbraucht (ecm) 9,3 6,6 7,2Vol. O 2 - consumed (ecm) 9.3 6.6 7.2

theoretische Vol. O2 theoretical vol. O 2

Theorie -.... 0,177 0,177 0,177Theory - 0.177 0.177 0.177

mg Sbsh oxydiertmg Sbsh oxidized

verbrauchte Vol. O9 consumed vol. O 9

Verbraucht 0,345 0,188 0,190Consumes 0.345 0.188 0.190

mg Sbsh oxydiert
5°mg Sbsh oxidized
5 °

Beispiel 2Example 2

Ein weiterer Vorteil des Verfahrens besteht in der Vermeidung von Nebenreaktionen, insbesondere vonAnother advantage of the process is the avoidance of side reactions, in particular of

909 729/39«909 729/39 "

solchen, die die Oxydationsbeständigkeit der behandelten Produkte merklich herabsetzen.those which noticeably reduce the oxidation resistance of the treated products.

Zwei Benzinproben (1) und (2), die durch Behandlung mit einer 7 Gewichtsprozent Chelat [Bis-(disalicylaläthylendiimin)-dikobalt-rnonohydrat] und einer 7 Gewichtsprozent Blei entsprechenden Menge Bleikresolat bei —10, -r-15 und 35° C gesüßt wurden, hatten die in Tabelle II angegebene Oxydationsbeständigkeit.Two gasoline samples (1) and (2), which by treatment with a 7 percent by weight chelate [bis- (disalicylalethylenediimine) -dicobalt monohydrate] and an amount of lead cresolate corresponding to 7% by weight of lead were sweetened at -10, -r-15 and 35 ° C, the in Oxidation resistance given in Table II.

Sie wurde nach der ASTM-Methode 525-55 bestimmt.It was determined according to ASTM method 525-55.

Tabelle IITable II

Temperaturtemperature Benzin (1)Petrol (1) Benzin (2)Petrol (2) -10- C
-15C
-35= C-10- C
-15C
-35 = C 306 Minuten
396 Minuten
644 Minuten306 minutes
396 minutes
644 minutes 190 Minuten
210 Minuten
250 Minuten190 minutes
210 minutes
250 minutes

Die verwendeten Benzine (1) und (2) hatten folgende Eigenschaften:The petrol (1) and (2) used had the following properties:

(1) Benzin:(1) gasoline:

Dichte bei 15= C 0,720Density at 15 = C 0.720

Siedepunkt Anfang und Ende 30° C; 180° CBoiling point beginning and end 30 ° C; 180 ° C

Sksh 0,010 g/100 cm3 Sksh 0.010 g / 100 cm 3

Oxydationsbeständigkeit 419 MinutenOxidation resistance 419 minutes

(2) Benzin:(2) gasoline:

Dichte bei 15= C 0,715Density at 15 = C 0.715

Siedepunkt Anfang und Ende 35° C; 148° CBoiling point beginning and end 35 ° C; 148 ° C

Sr5H 0,004 g/100 cm3 Sr 5 H 0.004 g / 100 cm 3

Oxydationsbeständigkeit 320 MinutenOxidation resistance 320 minutes

Die Beispiele 3 und 4 zeigen die Erhöhung der Oxydationsgeschwindigkeit von Mercaptanen (Mercaptiden) zu den entsprechenden Disulfiden, wobei die Verhältnisse von Metall-Chelaten (oder deren Komponenten) zur in den behandelten Produkten enthaltenen Mercaptan-Schwefelmenge gegeben sind.Examples 3 and 4 show the increase in the rate of oxidation of mercaptans (mercaptides) to the corresponding disulfides, the ratios of metal chelates (or their components) to the amount of mercaptan sulfur contained in the treated products given are.

Beispiel 3Example 3

Zwölf identische Proben eines irakischen Leichtbenzins mit den folgenden Eigenschaften:Twelve identical samples of Iraqi light petrol with the following characteristics:

Dichte bei 15° C 0,697Density at 15 ° C 0.697

Siedepunkt (Anfang und Ende) 34 bis 147° C
Srsh 0,014 g/100 ecmBoiling point (beginning and end) 34 to 147 ° C
Srsh 0.014 g / 100 ecm

werden mit einer 7 Gewichtsprozent des Chelats [Bis-(disalicylaläthylendiimin)-dikobalt-monohydrat] und einer 7 Gewichtsprozent Blei entsprechende Kresolatmenge enthaltenden Kresollösung behandelt. Die Ergebnisse sind aus Tabelle III ersichtlich, die die Mercaptan-Schwefelgehalte in g/100 ecm als Funktion der Reaktionszeit, der Reaktionstemperatur und des angewendeten Verhältnissesbe with a 7 weight percent of the chelate [bis (disalicylaläthylendiimin) dicobalt monohydrate] and a cresol solution containing 7% by weight of lead corresponding to an amount of cresolate. The results Table III shows the mercaptan sulfur content in g / 100 ecm as a function of the reaction time, the reaction temperature and the ratio used

ChelatChelate

(1/5,1/7 und 1/10)(1 / 5,1 / 7 and 1/10)

30 angibt.30 indicates.

( 1/5
. I 1'7(1/5
. I 1'7 1515th TabelleTabel IIIIII Zeit (St
Temperat
60Time (St.
Temperate
60 unden)
uren (0C)
15unden)
ures ( 0 C)
15th 22 4545 6060 1 i/io1 i / io 0,005
0,007
0,0090.005
0.007
0.009 3535 1
451
45 0,0015
0,003
0,0070.0015
0.003
0.007 0,003
0,0065
0,0080.003
0.0065
0.008 0,0005 !
0,0015 !
0,003 !0.0005!
0.0015!
0.003! 0,0005
0,0015
0,00250.0005
0.0015
0.0025 0,0005
0,002
0,0060.0005
0.002
0.006 T, , , . Chelat
ν erhältnis T,,, . Chelate
ν ratio 0,002
0,0025
0,00350.002
0.0025
0.0035 0,002
0,0025
0,0030.002
0.0025
0.003 SrshSrsh

1515th

3535

Zeit (Stunden)Time (hours)

Temperaturen (0C)
60 I 15Temperatures ( 0 C)
60 I 15

2424

4545

Verhältnisrelationship

ChelatChelate

3RSH3RSH

1/51/5

1/7
1/101/7
1/10

0,002
0,006
0,0070.002
0.006
0.007

D.S. 0,001 0,002D.S. 0.001 0.002

D.S.D.S. D.S.D.S. 0,000650.00065 0,00050.0005 0,0010.001 0,0040.004

0,0015
0,0055
0,0060.0015
0.0055
0.006

D.S.
0,0005
0,001DS
0.0005
0.001

D.S.
D.S.
D.S.DS
DS
DS

In dieser Tabelle bedeutet D. S. eine Abkürzung des Ausdrucks »Doctor = süß«.In this table, D.S. is an abbreviation of the expression "Doctor = sweet".

D.S.D.S.

D.S.D.S.

0,0020.002

Beispiel 4Example 4

Zu zwölf Proben eines kuwaitischen Leuchtpetroleums mit den folgenden Eigenschaften:For twelve samples of a Kuwaiti luminous petroleum with the following properties:

Dichte bei 15° C 0,8025Density at 15 ° C 0.8025

Siedepunkt (Anfang und Ende) 200 bis 247° C
Srsh 0,008 g/100 ecmBoiling point (beginning and end) 200 to 247 ° C
Srsh 0.008 g / 100 ecm

gibt man nacheinander eine erste, 1 g Disalicylaläthylendiimin auf 100 ecm Benzol enthaltende Lösung, eine zweite, 0,1 g/100 ecm Kobalt entsprechende Menge des Naphthenats und eine 0,55 g/100 ecm Blei entsprechende Menge des Naphthenats enthaltende Benzollösung zu. 70 an.are successively a first, 1 g of disalicylalethylenediimine to 100 ecm of benzene containing solution, a second amount of naphthenate corresponding to 0.1 g / 100 ecm cobalt and 0.55 g / 100 ecm lead Amount of the naphthenate containing benzene solution. 70 at.

Die Mengen der ersten und zweiten Lösung stehen in einem stöchiometrischen Verhältnis entsprechend dem Chelat Bis - (disalicylaläthylendiimin) - dikobalt - monohydrat, und die Proben werden unter den in Tabelle IV angegebenen Reaktionsbedingungen behandelt. Die Ergebnisse sind ebenfalls in Tabelle IV zusammengestellt. Sie gibt die Restschwefelgehalte in Form der Mercaptane, ausgedrückt in g/100 ecm, in Abhängigkeit von der Reaktionszeit, der Reaktionstemperatur und dem angewendeten VerhältnisThe amounts of the first and second solutions are in a stoichiometric ratio according to the Chelate bis (disalicylalethylenediimine) dicobalt monohydrate, and samples are taken under the conditions set out in Table IV Treated specified reaction conditions. The results are also shown in Table IV. It gives the residual sulfur content in the form of the mercaptans, expressed in g / 100 ecm, depending on the Reaction time, the reaction temperature and the ratio used

KobaltchelatCobalt chelate

SrshSrsh

(0,036, 0,026 und 0,018)(0.036, 0.026 and 0.018)

TabeUeIVTabeUeIV

1515th

3535

Zeit (Stunden) ITime (hours) I.

Temperaturen (DC) 60 I 15Temperatures ( D C) 60 I 15

3535

4545

Verhältnisrelationship

Kobalt
Srshcobalt
Srsh

0,036 0,026 0,0180.036 0.026 0.018

0,0048 i 0,0016 j 0,0011 i 0,0012
0,0056 I 0,0025 ! 0,0016 0,00160.0048 i 0.0016 j 0.0011 i 0.0012
0.0056 I 0.0025! 0.0016 0.0016

0,0072 ' 0,0040 ' 0,00320.0072 '0.0040' 0.0032

0,00320.0032

0,0032 i 0,0008 I 0,0008 ! 0,0008 0,0047 i 0,0008 0,0010 j 0,0012 0,0053 ! 0,0016 0,002 ' 0,00240.0032 i 0.0008 I 0.0008! 0.0008 0.0047 i 0.0008 0.0010 j 0.0012 0.0053! 0.0016 0.002 '0.0024

1515th

3535

Zeit (Stunden)Time (hours)

Temperaturen (0C)
60 I 15Temperatures ( 0 C)
60 I 15

2222nd

4545

Verhältnisrelationship

Kobalt
Srshcobalt
Srsh

0,0024 0,0039 0,00430.0024 0.0039 0.0043

0,00040.0004 0,00040.0004 0,00060.0006 0,00180.0018 D.S.D.S. D.S.D.S. 0,00040.0004 0,00080.0008 0,00100.0010 0,0010.001 D.S.D.S. D.S.D.S. 0,00120.0012 0,00160.0016 0,00200.0020 0,00160.0016 0,00040.0004 0,00100.0010

Spuren 0,0008 0,0016Lanes 0.0008 0.0016

Diese Ergebnisse zeigen den günstigen Einfluß der Temperaturerhöhung auf die Erhöhung der Oxydationsgeschwindigkeit der Mercaptane (Mercaptide) zu den entsprechenden Disulfiden.These results show the beneficial influence of the increase in temperature on the increase in the rate of oxidation the mercaptans (mercaptides) to the corresponding disulfides.

Claims (1)

Patentanspruch:Claim: Verfahren zur Oxydation von Mercaptanen (Mercaptiden) in Kohlenwasserstoffen zu Disulfiden mit Sauerstoff oder einem sauerstoffhaltigen Gas in Anwesenheit von Metallchelaten, erhalten durch Kondensation eines Iminophenols mit einer Verbindung eines Metalls der VIII. Gruppe des Periodischen Systems oder in Anwesenheit von zur Chelatbildung befähigten Komponenten, dadurch gekennzeichnet, daß man bei etwa 30° C oder höher unter Atmosphärendruck arbeitet.Process for the oxidation of mercaptans (mercaptides) in hydrocarbons to disulfides with oxygen or an oxygen-containing gas in the presence of metal chelates, obtained by condensation of an iminophenol with a compound of a metal of Group VIII of the Periodic Table or in the presence of components capable of chelating, thereby characterized in that one works at about 30 ° C or higher under atmospheric pressure. ©.909 729/398 2.60© .909 729/398 2.60
DENDAT1075249D 1957-05-10 Process for the oxidation of mercaptans !! (Mercaptides) in hydrocarbons to disulfides Pending DE1075249B (en)

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Families Citing this family (28)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3125506A (en) * 1964-03-17 Chelate sweetening
US4308169A (en) * 1978-12-26 1981-12-29 Uop Inc. Method of reactivating a catalytic composite of a carrier material and a mercaptan oxidation catalyst
US4318825A (en) * 1979-08-15 1982-03-09 Frame Robert R Catalytic composite, and method of manufacture
US4324650A (en) * 1979-10-01 1982-04-13 Uop Inc. Catalytic composite and process for use
US4337147A (en) * 1979-11-07 1982-06-29 Uop Inc. Catalytic composite and process for use
US4298463A (en) * 1980-07-11 1981-11-03 Uop Inc. Method of treating a sour petroleum distillate
US4360421A (en) * 1980-07-17 1982-11-23 Uop Inc. Method for treating mercaptans contained in a sour petroleum distillate
US4320029A (en) * 1980-07-17 1982-03-16 Uop Inc. Catalytic composite, method of manufacture, and process for use
US4824818A (en) * 1988-02-05 1989-04-25 Uop Inc. Catalytic composite and process for mercaptan sweetening
US4897180A (en) * 1988-02-05 1990-01-30 Uop Catalytic composite and process for mercaptan sweetening
US4913802A (en) * 1989-05-08 1990-04-03 Uop Process for sweetening a sour hydrocarbon fraction
US4908122A (en) * 1989-05-08 1990-03-13 Uop Process for sweetening a sour hydrocarbon fraction
US4923596A (en) * 1989-05-22 1990-05-08 Uop Use of quaternary ammonium compounds in a liquid/liquid process for sweetening a sour hydrocarbon fraction
US4929340A (en) * 1989-07-31 1990-05-29 Uop Catalyst and process for sweetening a sour hydrocarbon fraction using dipolar compounds
US5039398A (en) * 1990-03-19 1991-08-13 Uop Elimination of caustic prewash in the fixed bed sweetening of high naphthenic acids hydrocarbons
US5204306A (en) * 1990-08-27 1993-04-20 Uop Caustic free catalyst for use in a liquid/liquid process for sweetening a sour hydrocarbon fraction
US5180484A (en) * 1990-08-27 1993-01-19 Uop Caustic free liquid/liquid process for sweeting a sour hydrocarbon fraction
US5093296A (en) * 1990-08-27 1992-03-03 Uop Caustic free liquid/liquid process for sweetening a sour hydrocarbon fraction
US5273646A (en) * 1990-08-27 1993-12-28 Uop Process for improving the activity of a mercaptan oxidation catalyst
US5120453A (en) * 1990-12-24 1992-06-09 Uop Oxidative removal of cyanide from aqueous streams
US5064525A (en) * 1991-02-19 1991-11-12 Uop Combined hydrogenolysis plus oxidation process for sweetening a sour hydrocarbon fraction
US5424051A (en) * 1992-01-14 1995-06-13 Uop Process for the removal of carbon dioxide and mercaptans from a gas stream
US5232887A (en) * 1992-04-02 1993-08-03 Uop Catalyst for sweetening a sour hydrocarbon fraction
US5271835A (en) * 1992-05-15 1993-12-21 Uop Process for removal of trace polar contaminants from light olefin streams
US5318936A (en) * 1992-09-23 1994-06-07 Uop Catalyst for sweetening a sour hydrocarbon fraction containing metal oxide solid solution and magnesium oxide
US5413701A (en) * 1993-11-15 1995-05-09 Uop Process for sweetening a sour hydrocarbon fraction using a supported metal chelate and a solid base
US5413704A (en) * 1993-11-15 1995-05-09 Uop Process for sweetening a sour hydrocarbon fraction using a mixture of a supported metal chelate and a solid base
US5698103A (en) * 1996-10-04 1997-12-16 Uop Extraction of water-soluble metal chelates used as catalysts in sweetening sour hydrocarbon feedstocks

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2659691A (en) * 1949-08-26 1953-11-17 Raffinage Cie Francaise Process for refining petroleum products
US2651595A (en) * 1950-05-20 1953-09-08 Socony Vacuum Oil Co Inc Treating hydrocarbons
US2823173A (en) * 1952-06-19 1958-02-11 Raffinage Cie Francaise Methods of refining petroleum products
US2744854A (en) * 1952-06-30 1956-05-08 Universal Oil Prod Co Oxidation of mercaptans

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US2918426A (en) 1959-12-22
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