DE1105544B - Process for the production of mainly straight-chain saturated hydrocarbons - Google Patents
Process for the production of mainly straight-chain saturated hydrocarbonsInfo
- Publication number
- DE1105544B DE1105544B DEF28019A DEF0028019A DE1105544B DE 1105544 B DE1105544 B DE 1105544B DE F28019 A DEF28019 A DE F28019A DE F0028019 A DEF0028019 A DE F0028019A DE 1105544 B DE1105544 B DE 1105544B
- Authority
- DE
- Germany
- Prior art keywords
- color number
- sulfonic acids
- paraffins
- color
- hydrogenated
- 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.)
- Pending
Links
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
- C10G67/00—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one process for refining in the absence of hydrogen only
- C10G67/02—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one process for refining in the absence of hydrogen only plural serial stages only
- C10G67/14—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one process for refining in the absence of hydrogen only plural serial stages only including at least two different refining steps in the absence of hydrogen
-
- 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
- C10G73/00—Recovery or refining of mineral waxes, e.g. montan wax
- C10G73/02—Recovery of petroleum waxes from hydrocarbon oils; Dewaxing of hydrocarbon oils
- C10G73/24—Recovery of petroleum waxes from hydrocarbon oils; Dewaxing of hydrocarbon oils by formation of adducts
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F02—COMBUSTION ENGINES; HOT-GAS OR COMBUSTION-PRODUCT ENGINE PLANTS
- F02B—INTERNAL-COMBUSTION PISTON ENGINES; COMBUSTION ENGINES IN GENERAL
- F02B3/00—Engines characterised by air compression and subsequent fuel addition
- F02B3/06—Engines characterised by air compression and subsequent fuel addition with compression ignition
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
Description
Zur Herstellung von manchen Derivaten aliphatischer Kohlenwasserstoffe, so z. B. von Nitroalkanen, Alkylchloriden und insbesondere Sulfohalogeniden, ist die Verwendung vorwiegend geradkettiger gesättigter Paraffine als Ausgangsmaterial von großer Bedeutung. Derartige Paraffine sind weder durch Destillation noch durch Aromatenextraktion von paraffinischen Erdölen erhältlich.For the production of some derivatives of aliphatic hydrocarbons, such. B. of nitroalkanes, Alkyl chlorides, and especially sulfohalides, are predominantly straight-chain saturated ones Paraffins are of great importance as a starting material. Such paraffins are neither by distillation still obtainable by aromatic extraction from paraffinic petroleum.
Es ist bekannt, zur Herstellung von Paraffinsulfohalogeniden solche Kohlenwasserstoffgeraische zu verwenden, die durch Behandlung von Paraffinfraktionen mit Harnstoff, Abtrennung der so erhaltenen kristallisierten Harnstoffadditionsverbindungen und gegebenenfalls Waschen mit organischen Lösungsmitteln und Spaltung dieser Verbindungen gewonnen wurden. Aber auch die so erhältlichen Kohlenwasserstoffgemische genügen vielen Anforderungen, so z. B. den bei der Herstellung von Sulfochlorierungsprodukten gestellten Bedingungen, nur unvollständig. It is known to use such hydrocarbon devices for the production of paraffin sulfohalides, which crystallized by treating paraffin fractions with urea, separating the so obtained Urea addition compounds and optionally washing with organic solvents and cleavage of these compounds. But the hydrocarbon mixtures obtainable in this way also meet many requirements, so z. B. the conditions set for the production of sulfochlorination products, only incomplete.
Gegenstand dieser Erfindung ist ein Verfahren zur Gewinnung von vorwiegend geradkettigen gesättigten Kohlenwasserstoffen, das darin besteht, aus Paraffinfraktionen, insbesondere Erdölfraktionen, zunächst in bekannter Weise Harnstoffadditionsprodukte herzustellen, diese mit einem organischen Lösungsmittel in an sich bekannter Weise bis zum gewünschten Reinheitsgrad zu waschen, dann anschließend in üblicher Weise mit Wasser zu zersetzen und die so erhaltenen Paraffine schließlich zu destillieren und anschließend zu hydrieren.This invention relates to a process for the recovery of predominantly straight-chain saturated ones Hydrocarbons, which consists of paraffin fractions, in particular petroleum fractions, initially in known way to produce urea addition products, these with an organic solvent in to wash in a known manner to the desired degree of purity, then subsequently in the usual way Way to decompose with water and finally to distill the paraffins thus obtained and then to hydrate.
Zum Waschen der kristallisierten Harnstoffadditionsverbindungen eignen sich insbesondere organische Lösungsmittel für Paraffinkohlenwasserstoffe, deren Siedepunkt wesentlich unter demjenigen des zu gewinnenden Paraffins liegt, wie Petroläther, Cyclohexan und Benzol, chlorierte Kohlenwasserstoffe, wie Methylenchlorid und Äthylendichlorid, ferner Ketone, wie Aceton und Butanon. Das Waschen wird so lange fortgesetzt, bis der für den jeweiligen Verwendungszweck gewünschte Reinheitsgrad erreicht ist. Die Prüfung des Reinheitsgrades durch Zersetzen einer Adduktprobe und Analyse des dabei anfallenden Kohlenwasserstoffs hat sich vor allem auf Verunreinigungen aromatischer und hydroaromatischer Natur sowie auf die Farbzahl der daraus hergestellten Sulfosäurederivate, z. B. Salze oder Ester, zu erstrecken. Für die Verwendung der Paraffine zur Herstellung von Sulfochloriden z. B. ist in der Regel ein Reinheitsgrad entsprechend einem Gehalt von höchstens 0,1% an Aromaten bei praktischer Abwesenheit von Hydroaromaten erforderlich. Bei besonders hoher Anforderung ist der Aromatengehalt auf höchstens 0,01 % zu senken. Die Farbzahlen der Alkalisalze so-Verfahren zur GewinnungOrganic ones are particularly suitable for washing the crystallized urea addition compounds Solvent for paraffinic hydrocarbons whose boiling point is significantly below that of the to Winning paraffin lies, such as petroleum ether, cyclohexane and benzene, chlorinated hydrocarbons, such as Methylene chloride and ethylene dichloride, also ketones such as acetone and butanone. The washing will take so long continued until the required degree of purity for the intended use has been achieved. the Testing of the degree of purity by decomposing an adduct sample and analyzing the resulting product Hydrocarbon has mainly focused on impurities of an aromatic and hydroaromatic nature as well as the color number of the sulfonic acid derivatives produced from it, z. B. salts or esters to extend. For the use of paraffins in production of sulfochlorides z. B. is usually a degree of purity corresponding to a content of at most 0.1% of aromatics required in the practical absence of hydroaromatics. At particularly high The requirement is to reduce the aromatic content to a maximum of 0.01%. The color numbers of the alkali salts so process for extraction
vorwiegend geradkettiger gesättigterpredominantly straight-chain saturated
KohlenwasserstoffeHydrocarbons
Anmelder:Applicant:
Farbenfabriken Bayer Aktiengesellschaft, LeverkusenPaint factories Bayer Aktiengesellschaft, Leverkusen
Dr. Helmut Hanisch und Dr. Karl-Heinz Köhncke,Dr. Helmut Hanisch and Dr. Karl-Heinz Köhncke,
Krefeld-Bockum,
sind als Erfinder genannt wordenKrefeld-Bockum,
have been named as inventors
wie der Phenylester der Sulfosäure sollen im allgemeinen die Zahl 3 nicht überschreiten.Like the phenyl ester of sulfonic acid, the number should generally not exceed 3.
Die Destillation der gesättigten Kohlenwasserstoffe nach der Adduktaufspaltung soll der Hydrierung vorangehen, weil bei einer Destillation nach der Hydrierung wieder unerwünschte ungesättigte Produkte entstehen würden.The distillation of the saturated hydrocarbons after the adduct splitting should precede the hydrogenation, because in a distillation after the hydrogenation undesired unsaturated products are formed again would.
25 kg eines niederdeutschen Dieselölschnittes mit den Siedegrenzen 220 bis 310° C werden in einem mit Kühlschlange versehenen Rührgefäß mit einer Lösung von 37 kg Harnstoff in 601 Methanol versetzt und 2 Stunden unter Aufrechterhaltung einer Temperatur von 5° C lebhaft gerührt.25 kg of a Low German diesel oil cut with boiling points of 220 to 310 ° C are used in one with A stirred vessel provided with a cooling coil is mixed with a solution of 37 kg of urea in 60 liters of methanol and Stirred vigorously for 2 hours while maintaining a temperature of 5 ° C.
Das sich dabei ausscheidende Addukt wird abzentrifugiert und in drei Teile zerlegt, die jeweils in verschiedener Weise mit Benzol gewaschen werden. Teil 1 wird auf der Zentrifuge einmal mit Benzol nachgewaschen und durch Zentrifugieren vom Benzol befreit. Teil 2 wird in gleicher Weise wie Teil 1 behandelt, aber dann aus der Zentrifuge entnommen und dreimal mit frischem Benzol aufgeschlämmt, wobei nach jedesmaligem Aufschlämmen das Waschbenzol durch Zentrifugieren entfernt wird. Bei Teil 3 wird dieses Aufschlämmen in Benzol fünfmal wiederholt. The adduct which separates out is centrifuged off and broken down into three parts, each in be washed with benzene in various ways. Part 1 is done on the centrifuge once with benzene washed and freed from benzene by centrifugation. Part 2 is treated in the same way as Part 1, but then removed from the centrifuge and slurried three times with fresh benzene, being after each suspension the washing benzene is removed by centrifugation. In part 3 this slurrying in benzene is repeated five times.
Die so gewonnenen drei Addukte werden mit Wasser zersetzt, die freigesetzten Paraffine destilliert und bei 300° C über einem Nickel-Wolfram-Sulfid-Katalysator bei 200 atü nachhydriert. Das UV-Spektrum der unhydrierten Probe 3 zeigt nur noch Spuren aromatischer Kohlenwasserstoffe an.The three adducts obtained in this way are decomposed with water and the released paraffins are distilled and at 300 ° C over a nickel-tungsten-sulfide catalyst rehydrated at 200 atm. The UV spectrum of the unhydrogenated sample 3 only shows traces aromatic hydrocarbons.
109 578/3Ϊ7109 578 / 3Ϊ7
Claims (1)
punktaniline
Point
2
31
2
3
1,4353
1,43391.4360
1.4353
1.4339
0,773
0,7720.774
0.773
0.772
222
212220.7
222
212
93,5
94,092.6
93.5
94.0
2
31
2
3
der SulfosäurenNa salts
of sulfonic acids
Farbzahl 3
Farbzahl 1Color number 6
Color number 3
Color number 1
der SulfosäurenPhenol ester
of sulfonic acids
Farbzahl 4 bis 5
Farbzahl 2Color number 6
Color number 4 to 5
Color number 2
der Sulfosäurenof Na salts
of sulfonic acids
1,43391.4352
1.4339
0,7690.773
0.769
221224
221
93,793.0
93.7
Ibis 26th
Ibis 2
16th
1
Deutsche Auslegeschriften Nr. 1 038 684, 1049033; britische Patentschriften Nr. 736 472, 778 700;
USA.-Patentschriften Nr. 2 661 317, 2 656 342.Considered publications:
German Auslegeschriften No. 1 038 684, 1049033; British Patent Nos. 736 472, 778 700;
U.S. Patent Nos. 2,661,317, 2,656,342.
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEF28019A DE1105544B (en) | 1959-03-23 | 1959-03-23 | Process for the production of mainly straight-chain saturated hydrocarbons |
GB819560A GB879706A (en) | 1959-03-23 | 1960-03-08 | Process for obtaining substantially straight-chained saturated hydrocarbons |
BE588460D BE588460A (en) | 1959-03-23 | 1960-03-09 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEF28019A DE1105544B (en) | 1959-03-23 | 1959-03-23 | Process for the production of mainly straight-chain saturated hydrocarbons |
Publications (1)
Publication Number | Publication Date |
---|---|
DE1105544B true DE1105544B (en) | 1961-04-27 |
Family
ID=7092702
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DEF28019A Pending DE1105544B (en) | 1959-03-23 | 1959-03-23 | Process for the production of mainly straight-chain saturated hydrocarbons |
Country Status (3)
Country | Link |
---|---|
BE (1) | BE588460A (en) |
DE (1) | DE1105544B (en) |
GB (1) | GB879706A (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3328313A (en) * | 1964-11-30 | 1967-06-27 | Shell Oil Co | Liquid urea adduction |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2656342A (en) * | 1953-10-20 | Hydrocarbon segregation utilizing | ||
US2661317A (en) * | 1949-03-17 | 1953-12-01 | Texas Co | Separation of wax constituents and the like from oil |
GB736472A (en) * | 1953-09-14 | 1955-09-07 | British Petroleum Co | Improvements in or relating to the production of aviation fuel oils |
GB778700A (en) * | 1954-05-19 | 1957-07-10 | British Petroleum Co | Improvements in or relating to the separation of hydrocarbons |
DE1038684B (en) * | 1955-06-01 | 1958-09-11 | Nac Iacalvo Soteloia De Combus | Process for dewaxing lubricating oils |
DE1049033B (en) * | 1956-08-16 | 1959-01-22 | British Petroleum Co | Process for the separation of hydrocarbon mixtures |
-
1959
- 1959-03-23 DE DEF28019A patent/DE1105544B/en active Pending
-
1960
- 1960-03-08 GB GB819560A patent/GB879706A/en not_active Expired
- 1960-03-09 BE BE588460D patent/BE588460A/xx unknown
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2656342A (en) * | 1953-10-20 | Hydrocarbon segregation utilizing | ||
US2661317A (en) * | 1949-03-17 | 1953-12-01 | Texas Co | Separation of wax constituents and the like from oil |
GB736472A (en) * | 1953-09-14 | 1955-09-07 | British Petroleum Co | Improvements in or relating to the production of aviation fuel oils |
GB778700A (en) * | 1954-05-19 | 1957-07-10 | British Petroleum Co | Improvements in or relating to the separation of hydrocarbons |
DE1038684B (en) * | 1955-06-01 | 1958-09-11 | Nac Iacalvo Soteloia De Combus | Process for dewaxing lubricating oils |
DE1049033B (en) * | 1956-08-16 | 1959-01-22 | British Petroleum Co | Process for the separation of hydrocarbon mixtures |
Also Published As
Publication number | Publication date |
---|---|
BE588460A (en) | 1960-07-01 |
GB879706A (en) | 1961-10-11 |
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