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
  • 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
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/14—Organic compounds
  • C10L1/16—Hydrocarbons
  • C10L1/1616—Hydrocarbons fractions, e.g. lubricants, solvents, naphta, bitumen, tars, terpentine
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/14—Organic compounds
  • C10L1/18—Organic compounds containing oxygen
  • C10L1/19—Esters ester radical containing compounds; ester ethers; carbonic acid esters
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/14—Organic compounds
  • C10L1/22—Organic compounds containing nitrogen
  • C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
  • C10L1/224—Amides; Imides carboxylic acid amides, imides
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
  • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
  • C10M2203/1006—Petroleum or coal fractions, e.g. tars, solvents, bitumen used as base material
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
  • C10M2207/28—Esters
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
  • C10M2207/28—Esters
  • C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic acids
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
  • C10M2207/28—Esters
  • C10M2207/287—Partial esters
  • C10M2207/289—Partial esters containing free hydroxy groups
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
  • C10M2215/08—Amides [having hydrocarbon substituents containing less than thirty carbon atoms]
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
  • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
  • C10N2030/02—Pour-point; Viscosity index
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
  • C10N2040/00—Specified use or application for which the lubricating composition is intended
  • C10N2040/25—Internal-combustion engines
  • C10N2040/252—Diesel engines
• • 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

Definitions

• linear hydrocarbons can be separated from organic mixtures containing the same by treating the mixtures with urea.
• the linear compounds thereby form crystallized addition compounds and are separated from the mixtures in this form.
• the process is suitable inter alia for the removal of paraffin hydrocarbons from diesel oil or lubricating oil.
• lubrieating oil it is preferable, for the dilution of the reaction mixture, to work in the presence of a liquid which dissolves the mixture to be separated, but not urea.
• the additives may belong to a great variety of chemical classes. Hydrocarbons having a carbon number of at least 12, advantageously 12 to 20, and alcohols with carbon numbers of at least 10, preferably between and 20, are suitable. Suitable esters are those derived from mono or di-carboxylic acids and from monoor dihydric alcohols. Their carbon number should be more than 8, preferably between 10 and 20. The components from which the esters are built up may contribute to a very diiferent extent to the total carbon number. Thus alcohol radical small, for the acid radical to be small "ice it is possible for the acid radical to be large and the and the alcohol radical large, or for both to be of about the same size. Ketones used for the process may be symmetrical or unsymmetrical and their carbon number advantageously amounts to at least 9, preferably 9 to 20. Symmetrical or unsymmetrical ethers with carbon numbers of at least 8, preferably between 12 and 20, are
• the additives preferably should contain between 8 and 45 carbon atoms and should as far as possible be linear or in any case only slightly branched or should consist mainly of such compounds.
• the following additives may be enumerated by way of example and not by way of limitation: hydrocarbon mixtures rich in unbranched paraffin hydrocarbons with carbon numbers between about 14 and 17 such as are obtained from many petroleums or also synthetically; soft parafiin wax with mainly linear constituents with carbon numbers between about 18 and 26 and melting points between about 28 and 40 C.
• the process- may be carried out by first subjecting the mixture to a conventional urea treatment, then adding to the resultant raflinate one of the said additives and treating the mixture with urea.
• the treatment as a rule consists of a thorough mixing of the components. This operation may, if desired, be repeated one or more times.
• the initial mixture even when it has a relatively high pour point,
• the amount of urea to be used in all in one or more stages depends on the amount of adduct-fo-rrning substances to be removed from the mixture, i.e. the adductforming substances originally present and those added.
• urea As a general rule about 4 parts by weight of urea are necessary for the separation of 1 part by weight of adductforming substance. It is preferable to use a certain excess of urea, for example up to 6 parts by weight per part by weight of adduct-forming substance, in order that the reaction or in the reaction stage in question. In general, it is suitable to keep the density of the substance, i.e. the ratio of solid phase (in grams) to liquid phase (in ccs.), at a value of 1:4 or less.
• diluents there may be used especially lower chlorohydrocarbons with up to about 3 carbon atoms, such as methylene chloride, ethylene chloride, chloroform, carbon tetrachloride, trichlorethylene, trichlorethane and tetrachlorethane, and also low molecular weight carboxylic acid esters with up to about 5 carbon atoms, such as methyl acetate, ethyl acetate, ethyl propionate and methyl butyrate, and low molecular weight ketones with up to about 6 carbon atoms, such as acetone, butanone, diethyl ketone and methyl-isobutyl ketone. Oils which have been partly or wholly freed from paraffin hydrocarbons and which originate from the process itself may also serve as diluents. The process may be carried out with or without the addition of solvents for urea, such as methanol or ethanol.
• solvents for urea such as
• the adducts may be split up in known manner by treatment with liquids which dissolve the urea (for example with water or methanol) or with liquids which dissolve the enclosed organic compounds.
• the urea is used again for the deparaffination.
• the raffinate is freed in known manner from the solvent by distillation and the latter can be used again.
• the rafiinates obtained by the said process exhibit considerably lower pour points and cloud points than oils which have been obtained by urea-deparatfination without the use of additives.
• the process is suitable above all for the deparalfination of lubricating oils, such as spindle oils, turbine oils, oils for automobile and aircraft engines, diesel motor oils, gear oils and cylinder oils, but may if necessary be used for diesel oils or other relatively high boiling oils, for example oils boiling above about 200 C.
• Example 1 133 parts of lubricating oil (machine oil rafiinate 10 to 11 E./50 C., pour point +47 C.), 625 parts of ethylene chloride, 200 parts of urea, parts of a solution of urea in methanol which is saturated at room temperature and parts of methyl myristate are ground in a ball mill for 6 hours.
• the reaction mixture is filtered.
• the resultant filter cake (266 parts) yields, when split up, a mixture of 40 parts of myristic acid ester and 26 parts of hydrocarbon which can be split up into its constituents by distillation.
• the filtrate obtained by the filtration of the reaction mixture leaves behind, when the ethylene chloride has been distilled off, 107 parts of deparafiinated oil. This has a pour point of -l4 C. and does not cloud upon solidification. After adding 1% of the pour point depressant known under the registered trademark Fluxan N, the pour point is 16 C. and the cloud point is -l6 C.
• Example 2 100 parts of the preliminarily deparafiinated oil (pour point -3 C.) obtained according to paragraph 2 of Example 1 are mixed with 500 parts .of ethylene chloride and 10 parts of a solution of urea in methanol which is saturated at room temperature and while in a Retsch mill 28 parts of cetane and 200 parts of urea are gradually added in the course of 2 hours. After a grinding period of 2 hours in all, the reaction mixture is worked up as in Example 1. From the filtrate there are obtained 97 parts of an oil with the pour point l6 C. After adding 2.5% of Fluxan N, the product has a pour point and cloud point of -20 C.
• Example 3 133 parts of lubricating oil (pour point +47 C.) such as is used in Example 1, 500 parts of ethylene chloride, 150 parts of urea, 20 parts of a solution of urea in methanol which is saturated at room temperature and 40 parts of soft parafiin wax are ground for 6 hours in a ball mill. By working up according to Example 1, 108 parts of deparaffinated oil are obtained of which the pour point is -11 C. Addition of 1% of Fluxan N depresses the setting point to -16 C. The cloud point is l4 C.
• Example 4 133 parts of lubricating oil (machine oil raffinate, 10 to 11 E./50 C., pour point +47 C.), 800 parts of symmetrical tetrachlorethane, 200 parts of urea, 20 parts of a solution of urea in methanol which is saturated at room temperature and 40 parts of normal-pentadecane are ground for 2 hours in a Retsch mill. The reaction mixture is filtered. The filtrate, when the tetrachlorethane has been distilled ofi, leaves behind 109 parts of deparaffinated oil which has a pour point of 14 C. and a cloud point of 12 C.
• the filter cake (264 parts) is washed with tetrachlorethane and heated with 2000 parts of tetrachlorethane for 15 minutes at C.
• the reaction mixture is filtered while hot.
• the filtrate leaves behind by evaporation 64 parts of a hydrocarbon mixture from which by distillation there are separated as the low boiling point fraction 40 parts of normal-pentadecane which can also be used again as an additive.
• Example 5 133 parts of lubricating oil (machine oil raflinate, d 0.916; 7.7 E./50 C.; pour point +35 C.), 700 parts of trichlorethylene, 200 parts of urea and 10 parts of methanol are ground for 6 hours in a ball mill. During this period, a total of 40 parts of hard parafiin wax (melting point 50 to 52 C., average chain length of the paraflin C is added a little at a time to the mixture. The reaction mixture is then filtered. The filtrate leaves behind, after the trichlorethylene has been distilled off, parts of deparaffinated oil with a pour point of 13 C. (no previous clouding). From the filter cake, by
• Example 6 133 parts of lubricating oil (machine oil raffinate, 10 to 11 E./50 C.; pour point +47 C.), 450 parts of ethyl acetate, 200 parts of urea, 40 parts of normal do decyl alcohol and 20 parts of a solution of urea in methanol which is saturated at room temperature are ground in a ball mill for 6 hours. The mixture is centrifuged, the solution freed from ethyl acetate by distillation and again filtered. There remain behind 109 parts of deparaffinated oil having a pour point of --17 C.
• the filter cake (268 parts) yields upon separation a mixture of 40 parts of di-normal-heptyl ether and 28 parts of hydrocarbon which by distillation is separated into its constituents.
• the filtrate leaves behind, when the ethylene chloride is distilled off, 105 parts of deparaffinated oil with a pour point of 17" C.
• the recovered urea and the di-normal-heptal ether can be used again for deparaffination.
• the filter cake (264 parts) obtained after filtration is worked up as in the foregoing examples.
• a process for lowering the pour point of lubricating oils, diesel oils, and oils boiling above about 200 C. which comprises contacting said oils with urea in the presence of from about 10% to about 60% by weight based on the weight of the oil of an added substance having an adductforming speed greater than the mean adduct-forming speed of the parafiin hydrocarbons in said oil, said substance being selected from the group consisting of substantially linear aliphatic hydrocarbons having from 12 to'45 carbon atoms, soft paraflin waxes with substantially linear constituents having from about 18 to 26 car bon atoms and having melting points between about 28 C. and 40 C., hard paraifin waxes with substantially linear constituents having from about 24 to 45 carbon atoms and having melting points between about 50 C.
• linear alcohols having from 10 to 20 carbon atoms, linear carboxylic acid esters having from 10 to 20 carbon atoms, linear carboxylic acid esters derived from monocarboxylic acids and dihydric alcohols, said esters having from 10 to 20 carbon atoms, linear carboxylicacid esters derived from dicarboxylic acids and monohydric alcohols, such esters having 10 to 20 carbon atoms, linear ketones with 9 to 20 carbon atoms, linear ethers with 12 to 20 carbon atoms, and thereafter separating the urea parafiin addition compounds from saidlubricating oil.

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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)
• Health & Medical Sciences (AREA)
• Emergency Medicine (AREA)
• Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
• Lubricants (AREA)

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Cited By (2)

Citations (2)

• 1958
  • 1958-04-17 DE DEB48592A patent/DE1063738B/de active Pending
• 1959
  • 1959-04-08 BE BE577480A patent/BE577480A/fr unknown
  • 1959-04-14 US US80621759 patent/US3044949A/en not_active Expired - Lifetime
  • 1959-04-15 GB GB12747/59A patent/GB872274A/en not_active Expired

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