US2142980A - High molecular weight polar compounds and process of making the same - Google Patents

High molecular weight polar compounds and process of making the same Download PDF

Info

Publication number
US2142980A
US2142980A US128278A US12827837A US2142980A US 2142980 A US2142980 A US 2142980A US 128278 A US128278 A US 128278A US 12827837 A US12827837 A US 12827837A US 2142980 A US2142980 A US 2142980A
Authority
US
United States
Prior art keywords
molecular weight
temperature
boiling
reacting
condensation
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
Application number
US128278A
Other languages
English (en)
Inventor
Huijser Hendrik Willem
Nooijer Christiaan Nicolaas De
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.)
Shell Development Co
Original Assignee
Shell Development Co
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Shell Development Co filed Critical Shell Development Co
Application granted granted Critical
Publication of US2142980A publication Critical patent/US2142980A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • H—ELECTRICITY
    • H02—GENERATION; CONVERSION OR DISTRIBUTION OF ELECTRIC POWER
    • H02K—DYNAMO-ELECTRIC MACHINES
    • H02K19/00—Synchronous motors or generators
    • H02K19/02—Synchronous motors
    • H02K19/04—Synchronous motors for single-phase current
    • H02K19/06—Motors having windings on the stator and a variable-reluctance soft-iron rotor without windings, e.g. inductor motors
    • C—CHEMISTRY; METALLURGY
    • C06—EXPLOSIVES; MATCHES
    • C06F—MATCHES; MANUFACTURE OF MATCHES
    • C06F3/00—Chemical features in the manufacture of matches
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
    • C07C2/02—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons
    • C07C2/04—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • 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
    • C10M143/00—Lubricating compositions characterised by the additive being a macromolecular hydrocarbon or such hydrocarbon modified by oxidation
    • 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
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • 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
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • 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
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/04—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an alcohol or ester thereof; bound to an aldehyde, ketonic, ether, ketal or acetal radical
    • 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
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/06—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an acyloxy radical of saturated carboxylic or carbonic acid
    • 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
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/06—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an acyloxy radical of saturated carboxylic or carbonic acid
    • C10M2209/062—Vinyl esters of saturated carboxylic or carbonic acids, e.g. vinyl acetate
    • 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
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
    • C10M2209/086—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type polycarboxylic, e.g. maleic acid
    • 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
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • 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
    • C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2211/06—Perfluorinated compounds
    • 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
    • C10M2213/00—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions
    • 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
    • C10M2213/00—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2213/02—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions obtained from monomers containing carbon, hydrogen and halogen only
    • 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
    • C10M2213/00—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2213/04—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions obtained from monomers containing carbon, hydrogen, halogen and oxygen
    • 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
    • C10M2213/00—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2213/06—Perfluoro polymers
    • 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
    • C10M2213/00—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2213/06—Perfluoro polymers
    • C10M2213/062—Polytetrafluoroethylene [PTFE]
    • 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
    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • 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
    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/02—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds
    • 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
    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • 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
    • C10M2221/00—Organic macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2221/04—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2221/041—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds involving sulfurisation of macromolecular compounds, e.g. polyolefins
    • 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
    • C10M2225/00—Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • 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
    • C10M2225/00—Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2225/02—Macromolecular compounds from phosphorus-containg monomers, obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • 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
    • C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
    • C10M2227/06—Organic compounds derived from inorganic acids or metal salts
    • C10M2227/061—Esters derived from boron
    • 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
    • C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
    • C10M2227/09—Complexes with metals
    • 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
    • C10N2050/00—Form in which the lubricant is applied to the material being lubricated
    • C10N2050/10—Semi-solids; greasy

Definitions

  • This invention relates to valuable high-molecular weight organic compounds. of polar character possessing in their structure long carbon-to-carbon chains and having high boiling temperatures, and it also relates to a process for the manufacture oi such valuable compounds which comprises reacting an unsaturated hydrocarbon possessing one double bond with an unsaturated hydrocarbon possessing a plurality of double bonds at a temperature below about 0 C., and reacting the resulting long chain, polyolefinic hydrocarbon product with a reagent capable of reacting therewith by addition to a double bond, whereby a high-boiling, high-molecular weight polar compound adapted to many commercial uses is obtained.
  • the invention provides a practical and economical process for the production of highmolecular weight polar compounds of controlled and improved character from petroleum hydrocarbons or hydrocarbons derived from petroleum or petroleum products.
  • the products which are readily obtained in practical yields from such raw materials, are suitable for a wide variety of They are particularly suitable as agents which when added in effective amount to hydrocarbon mixtures, such as lubricating oils, greases, and the like, improve certain characteristics of such mixtures and make them more suitable tor particular as well as general purposes.
  • the viscosity index of lubricating oils may be materially increased by adding thereto a small amount of one or a mixture of such polar compounds.
  • oils comprising relatively small amounts of the agents to which the invention relates, have better lubricating properties, the agents serving to increase their oiliness.
  • the addition of high-boiling polar compounds to lubricating oils also increases their stability, rendering them useful as extreme pressure lubricating compositions.
  • the compounds described act as anti-oxidants; hydrocarbon compositions to which they are added are less subject to auto-oxidation.
  • Other uses for the high molecular weight polar compounds will be apparent to those skilled in the art.
  • oleflne is used herein and in the appended claims to designate such hydrocarbons which possess one olefinic linkage, said linkage being between two aliphatic carbon atoms.
  • the following are representative olefines, which may be applied severally or in admixture: ethylene, propylene, the secondary and tertiary base butylenes, as l-butene, 2sbutene and tertiary butylene, the secondary and tertiary base amylenes, hexylenes, heptylenes, octylenes, nonylenes and their higher homologues.
  • the olefine co-polymers as dipropylene, di-beta-butylene, diisobutylene, triisobutylene, the diand tri-amylenes, hexylenes, and the lie, as well as the oleflne inter-polymerization products resulting from the polymerization of an olefine with an oleflne of another species, are comprehended as embraced by the term olefine.
  • the invention may be executed employing various hydrocarbons which are characterized by the possession in their structure of a plurality of olefinic linkages. Diolefines are especially suitable, particularly the conjugated double bond dioleflnes.
  • diolefines are butadiene, isoprene, 2,3-dimethyl butadiene-(1,3), 2-ethyl butadiene-(1,3) 1,3- dimethyl butadiene-(1,3) pentadiene- (1,3) pentadiene-(1,4), S-methyl pentadiene-(2,4), 3,-i-dimethyl pentadiene-(2,4), the straight chain, branched chain and cyclic hexadienes, heptadienes, etc., and their homologues, analogues and hydrocarbon substitution products.
  • the diolefines may be used severally, or mixtures comprising more than one species of dioleflne may be applied. Diolefines as diallyl, diisobutenyl, diisoamyl and the like, wherein the two double bonds are not conjugated, also come into consideration as useful diolefines.
  • olefines and dioleflnes, or mixtures of the same, from any convenient source may be used.
  • Relatively pure unsaturated hydrocarbon compounds, such as the straight chain, branched chain, and cyclic olefines may be reacted with relatively pure straight chain, branched chain, and cyclic diolefines, or mixtures of these may be reacted together in controlled proportions to produce the valuable high-molecular weight polar compounds to which the invention relates.
  • hydrocarbon mixtures comprising dioleflnes and olefines, or particular fractions of such mixtures may be advantageously treated in accordance with the process of the invention.
  • Such hydrocarbon mixtures are obtainable by the pyrogenesis or cracking of petroleum oils, shale oils, petroleum products, etc., and by the destructive distillation of coal, peat, pitches, waxes, asphalts, animal oils, vegetable oil and the like carbonaceous material. Cracked petroleum distillates or special fractions of'such distillates are useful starting materials.
  • distiliates may be used per se when they contain the desired proportions of oleilnes and dioleflnes, or different fractions may be mixed depending upon their composition and the desired composition of the mixture to be treated, or varying proportions of relatively pure oleflnes and/or dioleflnes may be mixed with certain hydrocarbon fractions to provide starting materials of the desired composition.
  • a substantial molecular excess of an oleilne is condensed with a diolefine at a temperature not greater than C. and in the presence of a suitable polymerization or condensation agent or catalyst.
  • Catalysts of the class known as condensation catalysts have been found to be useful for our purpose.
  • a suitable subgroup of catalysts embrace the acid-acting halides of the elements aluminum, boron, iron, tin, antimony, arsenic, bismuth, molybdenum, tungsten, vanadium, zinc, titanium, thorium, cerium, zirconium, indium, thalium and the like.
  • catalysts of this subgroup are particularly suitable catalysts of this subgroup.
  • Another valuable subgroup of catalysts comprises the above-described and the like acidacting halides in combination to form a complex catalyst with an inorganic or organic compound possessing a dipole moment.
  • Such a complex catalyst may comprise an acid-acting metal halide or boron halide in combination with an inorganic acid-acting halide of another species, with a hydrogen halide, or with an inorganic neutral-acting metal halide such as the alkali metal halides, the alkaline earth metal halides, the halides of metals as nickel, silver, cobalt, and the like.
  • such a complex catalyst may comprise an acid-acting metal halide or boron halide in combination as a complex with an organic oxycompound possessing a dipole moment such as the organic nitro-compounds of which the nitroparafllns, the nitro-aralkyl compounds, and the nitro-isocyclic compounds as nitro-benezene, nitro-cyclohexane and the like and their homologues and substitution products are representative; such as the ketones of aliphatic, aralkyl, aromatic or mixed character of which acetone, methyl ethyl retone, methyl propyl ketone, acetophenone, ethyl phenyl ketone, benzophenone and the like and their homologues and substitution products are representative; such as the aliphatic, aralkyl or aromatic carboxylic acid halides, particularly the aromatic carboxylic acid halides as benzoyl chloride, benzoyl bromide, etc.,
  • Condensation catalysts comprising an aluminum halide such as AlCl3, AlBrs, AlCla-NaCl, AlCl:BaClz, AlBr:KCl, AlCl3--AgCl, A1F3 NaCl, AlBr3AgBr, AlBn-BaBn, AlClanitromethane, AlCl:nitrobenzene, AlCh-nitrobenzene-NaCl, AlCls-acetone, ACla-acetophenone, AlCla-benzophenone, AlCla-benzoyl chloride,
  • aluminum halide such as AlCl3, AlBrs, AlCla-NaCl, AlCl:BaClz, AlBr:KCl, AlCl3--AgCl, A1F3 NaCl, AlBr3AgBr, AlBn-BaBn, AlClanitromethane, AlCl:nitrobenzene, AlCh-nitro
  • AlCla-diphenyl sulphone, AlCh-dibenzyl sulphone and the like may be advantageously employed.
  • Another preferred subgroup of condensation catalysts embraces those comprising a boron halide such as BF: BCla, BF:HF, BF:- NaCl, BCla-NaCl, BFa-AgF, BF:-BaClz, BIB- nitromethane, BFE
  • condensation and/or polymerization catalysts of acid, basic or neutral character may be advantageously used.
  • the contact condensation catalysts as the heavy metal oxides, benzoyl peroxide and the like, the siliceous materials as fuller's earth, diatomaceous earth, Florida earth, kieselguhr, silica gel, porcelain chips, etc., charcoal and the like may be used to advantage.
  • the catalysts may be prepared in any suitable manner and used singly or in admixture. If desired, the metal halide and boron halide catalysts may be used in admixture with or deposited on the siliceous materials as clay, silica gel, etc.
  • a suitable reaction vessel comprises a kettle of the desired capacity equipped with mechanical stirring means, suitable means for cooling and heating its contents, and suitable inlet and outlet means.
  • Suitable refrigerating means employing liquid ammonia, sulphur dioxide, propane, butane, etc. may be used to maintain the contents of the reaction vessel at the desired low temperature during the condensation reaction.
  • the reaction is preferably effected in the liquid phase; however, one or more of the reactants may be in the vapor phase.
  • gaseous ethylene or propylene may be passed into a liquid mixture of one or more diolefines and the condensation catalyst.
  • the reactants in the desired proportions may be mixed before, during or after their introduction into the reaction vessel.
  • the proportions of the olefine to the dioleflne in the mixture condensed may vary considerably depending upon the nature of the high-molecular weight polar compound desired. Preferably we employ a considerable molecular excess of the oleilne over the diolefine.
  • stable polyolefinic hydrocarbon products of the desired high-molecular weight are obtained.
  • Polyoleflnic hydrocarbon materials having molecular weights as high as 10,000 and higher may be obtained by the condensation reaction.
  • the condensation product may contain 10 double bonds and have a molecular weight as high as about 5600 (an equivalent molecular weight of about 560 per olefinic linkage).
  • the condensation may or may not be effected in the presence of a solvent or diluent.
  • a solvent or diluent When hydrocarbon fractions containing olefines and diolefines are treated, the inert hydrocarbons may act as solvents or diluent which may be subsequently separated from the products.
  • suitable inert solvents or diluents When pure olefines and diolefines are recated, suitable inert solvents or diluents may be added. It is desirable to employ a solvent or diluent which is inert under the conditions of the condensation reaction.
  • the condensation catalyst may be added to the reaction mixture as a solid, as a liquid in some auaoeo cases, or suspended or dissolved in a suitable medium or solvent therefor.
  • the desired amount of the catalyst may be added to the reaction mixture in the reaction vessel all at once, but it is preferably added to the agitated reaction mixture slowly in a continuous or intermittent manner until the required amount has been added.
  • An effective amount of the catalyst is added.
  • the relative amount oi the catalyst used in each particular case will depend upon the particular catalyst or mixture of catalysts employed, upon the particular reactants condensed, and upon the nature of the particular end-product desired. By a suitable regulation of the rate of addition of the catalyst, the temperature of the reaction mixture may be more eflectively maintained within the desired temperature range.
  • the condensation reaction is eflected at a temperature not greater than about 0 C. Temperatures in the range of from -l00 C. to 0 C. are in general suitable but lower temperatures may be employed if desired. The low reaction temperature is maintained by suitable cooling of the reaction vessel. The reaction is advantageously eilected at atmospheric pressure. Subatmospheric or superatmospheric pressures may be used if desired.
  • the condensation reaction is preferably effected while stirring the reaction mixture to eflect more intimate contact of the reactants with each other and the catalyst.
  • the condensation reaction has proceeded to substantial completion or to the desired extent, the polyoleflnic hydrocarbon product of high molecular weight is caused to react with a reagent capable of reacting therewith by addition to one or more of the oleflnic linkages, whereby the hydrocarbon condensation product is converted to a high-molecular weight, high-boiling polar compound particularly useful as a component of lubricating oils and greases.
  • Suitable reagents capable ofreacting with the double bonds of the hydrocarbon condensation products by addition thereto without disrupting the hydrocarbon chain of the condensation prodnot are the halogens, as chlorine and bromine, the carboxylic acids, the substituted carboxylic acids, the carboxylic acid anhydrides, the mineral acids as hydrogen sulphide, the boric acids, hydrogen cyanide, the phosphoric acids, sulphuric acid, etc., the acid anhydrides as sulphur dioxide, the nitrogen oxides, the phosphorus oxides, etc., the polyhydric alcohols, particularly those containing three or more carbinol groups as glycerol, alphamethyl glycerol, beta-methyl glycerol, alphaethyl glycerol, beta-ethyl glycerol and the like and their homologues and analogues.
  • the halogens as chlorine and bromine
  • a particularly suitable subgroup oi reagents which may be reacted with the polyoleflnic hydrocarbon materials resulting from the condensation embraces those which are of acid character, that is, which are themselves acids or which are capable of forming acids on reaction with water. Included in this subgroup are the mineral acids, the mineral-acting acids, the carboxylic acids, the substituted carboxylic acids, other organic acids, the mineral acid anhydrides, the carboxylic acid anhydrides and the like which are capable of reacting with an olefinic hydrocarbon by addition to the double bond thereof.
  • Hydrogen sulphide is a representative mineral acid of 'this subgroup; acetic acid is a representative monocarboxylic acid; maleic acid is a representative polycarboxylic acid; thioglycolic acid is a representative substituted carboxylic acid; sulphur dioxide is a representative mineral acid anhydride; acetic anhydride is a representative monocarboxylic acid anhydride; and maleic acid anhydride is a representative polycarboxylic acid anhydride.
  • the polycarboxylic acid anhydrides especially maleic acid anhydride and its homologues, analogues and substitution products, are particularly suitable.
  • the reaction whereby a reagent is added to a double bond of the polyoleflnic condensation product may be efl'ected in the same reaction vessel in which the condensation was eii'ected, or it may be eifected in another vessel better adapted to the particular additive reaction. In general, the same reaction vessel, it it is adapted to use at high as well as low temperatures, may be used throughout.
  • the relative amount of the particular reagent to be reacted with the polyoleflnic hydrocarbon material depends upon the nature of the product, that is, upon whether it is desired to saturate all, several or only one 01' the oleflnic linkages oi. a molecule of the hydrocarbon.
  • the conditions of temperature, pressure, etc., at which the addition reaction is effected will depend upon the nature of the particular addition reaction involved. For example, some of the addition reactions are best effected at room temperature or lower temperatures, while other are best eflected at elevated temperatures.
  • a halogen such as chlorine
  • the chlorination may be eflected with the chlorine in the liquid or gaseous phase, and in the presence or absense of a catalyst.
  • the chlorination may be eilected at about room temperature, temperatures below room temperatures, or at moderately elevated temperatures.
  • Suitable chlorination catalysts are, e. g., the metal halides as ferric chloride, nickel chloride, calcium chloride and the like.
  • the carboxylic acids and carboxylic acid anhydrides are preferably reacted with the poyoleflnic hydrocarbon material at elevated temperatures.
  • the carboxyic acid anhydrides such as maleic acid anhydride
  • the carboxyic acid anhydrides are conveniently reacted with one or more double bonds of the polyoleflnic material at temperatures of from about 100 C. to about 300 C. or higher.
  • maleic acid anhydride is the reagent added, it is, in general, desirable to employ it in excess and eflect the reaction at a temperature of about 200 C.
  • the resulting product may be hydrolyzed by heating it with water at an elevated temperature of about 100 C. or higher, whereby a high-molecular weight, high-boiling polycarboxylic acid is obtained.
  • the following specific example illustrates a suitable mode of executing the process of the invention to obtain an oil-soluble organic polar compound of high-molecular weight and highboiling temperature which is a valuable agent to add to lubricating oils to increase their viscosity index, their oiliness, their extreme pressure lubrieating qualities and other characteristics. It is to be understood that the invention is not to be regarded as limited to the specific reactants, catalyst, or mode of operation disclosed in the example.
  • the product of the hydrolysis reaction was a high-boiling polycarboxylic acid having a weight equivalent of about 2000.
  • a process for the production of organic polar compounds of high molecular weight and boiling temperature which comprises condensing an oleflne with a polyoleflne at a temperature not greater than about C., and reacting the resulting high-molecular weight polyolefinic hydrocarbon product with a reagent capable of reacting therewith by addition to an olefinic linkage whereby a high-boiling polar compound is obtained.
  • a process for the production of organic polar compounds or high molecular weight and boiling temperature which comprises condensing an oleflne with a diolefine in the presence of a condensation catalyst at a temperature not greater than about 0 C., and reacting the resulting high-molecular weight polyolefinic hydrocarbon product with a reagent capable of reacting therewith by addition to an olefinic linkage whereby a high-boiling polar compound is obtained.
  • a process for the production of organic polar compounds of high molecular weight and boiling temperature which comprises condensing a substantial molecular excess of an olefine with a dioleflne in the presence of a condensation catalyst at a temperature not greater than about 0 C., and reacting the resulting high-molecular weight polyolefinic hydrocarbon product with a reagent capable of reacting therewith by addition to an olefinic linkage whereby a high-boiling polar compound is obtained.
  • a process for the production of organic polar compounds of high molecular weight and boiling temperature which comprises condensing an olefine with a diolerlne in the presence of a condensation catalyst comprising an acid-acting halide of the class consisting of the acid-acting metal halides and the boron halides at a temperature not greater than about 0 C., and reacting the resulting high-molecular weight polyoleflnic hydrocarbon product with a reagent capable of reacting therewith by addition to an oleflnic linkage whereby a high-boiling polar compound is obtained.
  • a condensation catalyst comprising an acid-acting halide of the class consisting of the acid-acting metal halides and the boron halides at a temperature not greater than about 0 C.
  • a process for the production or organic polar compounds of high molecular weight and boiling temperature which comprises condensing an olefine with a dioleflne in the presence of a condensation catalyst comprising an aluminum halide at a temperature below about 0 C., and reacting the resulting high-molecular weight polyolefinic hydrocarban product with a reagent capable of reacting therewith by addition to an oleflnic linkage whereby a high-boiling polar compound is obtained.
  • a process for the production of organic polar compounds of high molecular weight and boiling temperature which comprises condensing an oleline with a diolefine in the presence of a condensation catalyst at a temperature not greater than about 0 C., and reacting the resulting highmolecular weight polyolefinic hydrocarbon product with a reagent of acid character capable of reacting therewith by addition to an olefinic linkage whereby a high-boiling polar compound is obtained.
  • a process for the production of organic polar compounds of high molecular weight and boiling temperature which comprises condensing an oleflne with a dioleilne in the presence of a condensation catalyst at a temperature not greater than about 0 C., and reacting the resulting highmolecular weight polyoleflnic hydrocarbon product with a reagent of the class consisting of carboxylic acids and carboxylic acid anhydrides which is capable of reacting therewith by addition to an olefinic linkage whereby a high-boiling polar oxy-compound is obtained.
  • a process for the production of organic polar compounds of high molecular weight and boiling temperature which comprises condensing an olefine with a diolefine in the presence of a condensation catalyst at a temperature not greater than about 0 C., and reacting the resulting highmolecular weight polyoleflnic hydrocarbon product with a carboxylic acid anhydride, the acid anhydride adding to an oleflnic linkage of the unsaturated hydrocarbon product whereby a highboiling oxy-compound of high-molecular weight is obtained.
  • a process for the production of organic polar compounds of high molecular weight and boiling temperature which comprises condensing an olefine'with a diolefine in the presence of a condensation catalyst at a temperature not greater than about 0 C., and reacting the resulting high-molecular weight polyoleflnic hydrocarbon product with maleic acid anhydride whereby a high-boiling oxy-compound of high-molecular weight is obtained.
  • a process for the production of organic polar compounds of high molecular weight and boiling temperature which comprises condensing an olefine with a dioleflne in the presence of a condensation catalyst comprising boron fluoride at a temperature not greater than about 0 C.,
  • a processior. the production of organic polar compounds of high molecular weight and boiling temperature which comprises condensing a substantial molecular excess of an olefine with a diolefine in the presence of boron fluoride at a temperature not greater than about 0., and reacting the resulting high-molecular weight polyolefinic hydrocarbon product with a carboxylic acid anhydride, whereby a high-boiling polar compound is obtained.
  • a process for the production of organic polar compounds of high molecular weight and boiling temperature which comprises condensing a substantial molecular excess ofan olefine with a conjugated double bond diolefine in the presence. of boron fluoride at a temperature not greater than about 0 0., and reacting the resulting high-molecular weight polyoleflnic hydrocarbon product with maleic acid anhydride at a temperature greater than about 100 0., whereby a high-boiling polar compound is obtained.
  • a process for the production of organic polar compounds of high molecular weight and boiling temperature which comprises condensing about nine parts by weight of isobutene with about one part by weight of butadiene in the presence of boron fluoride at a temperature of about 80 0., reacting the resulting high-molecular weight polyolefinic hydrocarbon product with an excess of maleic acid anhydride at a temperature of about 200 0., and heating the reaction mixture with water at a temperature of about 100 0., whereby a high-boiling polycarboiwlic acid having a weight equivalent of about 2000 is obtained.
  • a process for the production of organic polar compounds of high molecular weight and boiling temperature which comprises condensing an olefine with a diolefine in the presence of a condensation catalyst comprising aluminum chloride at a temperature not greater than about 0' 0., and halogenating the resulting high-molecular weight polyoleflnic hydrocarbon product whereby a high-boiling polyhalogenated organic compound is obtained.
  • a process for the production of organic polar compounds of high molecular weight and boiling temperature which comprises condensing a substantial molecular excess of an olefine with 18.
  • composition of matter the organic polar compounds of high molecular weight and boiling temperature obtained by condensing an olefine with a diolefine in the presence of a condensation catalyst at a temperature not greater than about 0 0. and reacting the resulting polyoleflnic hydrocarbon product with an agent capable of reacting therewith by addition to an olefinic linkage.
  • composition of matter the organic polar compounds of high molecular weightand boiling temperature obtained by condensing a substantial molecular excess of an olefine with a dioleiine in the presence of a condensation catalyst comprising an acid-acting halide of the class consisting of the acid-acting metal halides and the boron halides at a temperature not greater than about 0 C. and reacting the resulting polyolefinic hydrocarbon product with maleic acid anhydride.
  • a process for the production of organic polar compounds of high molecular weight and boiling temperature which comprises condensing a substantial molecular excess of a tertiary olefine with a diolefine in the presence of a condensation catalyst at a temperature not greater than about 0 0., reacting the resulting highmolecular weight polyolefinic' hydrocarbon product with an excess of a carboxylicacid anhydride at a temperature of about 200 0., and heating the resulting reaction mixture with water at a temperature of about 100 0., whereby a high-boiling polycarboxylic acid having a high weight equivalent is obtained.
  • a composition of matter the organic polar compounds of high molecular weight and boiling temperature obtained by condensing a substantial molecular excess of an olefine with a diolefine in the presence of a condensation catalyst comprising an acid-acting halide of the class consisting of the acid-acting metal halides and the boron halides at a temperature not greater than about 0 0. and reacting the resulting polyolefinic hydrocarbon product with carboxylic acid anhydrode.
  • a condensation catalyst comprising an acid-acting halide of the class consisting of the acid-acting metal halides and the boron halides at a temperature not greater than about 0 0.
  • a process for the production of organic polar compounds of high molecular weight and boiling temperature which comprises condensing an olefine with a dioleflne in the mol ratio of about 9 to 1 in the presence of a condensation catalyst comprising an acid-acting halide of the class consisting of the acid-acting metal halides and the boron halides at a temperature not greater than about 0 0., and reacting the resulting high-molecular weight polyoleflnic hydrocarbon product with a reagent capable of reacting therewith by addition to an oleflnic linkage whereby a high-boiling polar compound is obtained.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Power Engineering (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
US128278A 1936-03-24 1937-02-27 High molecular weight polar compounds and process of making the same Expired - Lifetime US2142980A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
NL2142980X 1936-03-24

Publications (1)

Publication Number Publication Date
US2142980A true US2142980A (en) 1939-01-03

Family

ID=19873736

Family Applications (1)

Application Number Title Priority Date Filing Date
US128278A Expired - Lifetime US2142980A (en) 1936-03-24 1937-02-27 High molecular weight polar compounds and process of making the same

Country Status (2)

Country Link
US (1) US2142980A (xx)
NL (3) NL43011C (xx)

Cited By (90)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2417093A (en) * 1941-09-06 1947-03-11 Jasco Inc Sulfurized, milled, and cured polymer
US2418797A (en) * 1939-04-01 1947-04-08 Standard Oil Co Continuous process for polymerizing olefins
US2422278A (en) * 1943-12-01 1947-06-17 Standard Oil Dev Co Lubricating oil composition
US2431461A (en) * 1943-12-16 1947-11-25 Standard Oil Dev Co Olefinic polymerization pretreatment
US2439610A (en) * 1944-09-26 1948-04-13 Shell Dev Stabilized organic composition
US2442218A (en) * 1941-08-27 1948-05-25 Jasco Inc Interpolymers of isoolefine with diolefins and process of producing same
US2442644A (en) * 1946-04-02 1948-06-01 California Research Corp Method of controlling viscosity of hydrocarbon polymers
US2442643A (en) * 1946-04-02 1948-06-01 California Research Corp Process of activating polymerization of hydrocarbons
US2443287A (en) * 1943-05-15 1948-06-15 Standard Oil Dev Co Polymerization catalyst
US2446897A (en) * 1942-12-24 1948-08-10 Standard Oil Dev Co Process for polymerizing olefinic compounds with metal halide-organic acid double salts
US2447610A (en) * 1943-12-07 1948-08-24 Standard Oil Dev Co Solid halogen derivatives of polymerized methyl pentadiene
US2456228A (en) * 1943-12-08 1948-12-14 Libbey Owens Ford Giass Compan Method of dispersing a solid polymerization catalyst in a polymerizable thermosetting resin sirup
US2465292A (en) * 1945-10-19 1949-03-22 Standard Oil Dev Co Chemical process
US2468523A (en) * 1943-06-10 1949-04-26 Standard Oil Dev Co Delayed-action polymerization process
US2477018A (en) * 1944-12-30 1949-07-26 Standard Oil Dev Co Synthetic rubbery copolymers of normal olefins with diolefins
US2491710A (en) * 1943-06-16 1949-12-20 Standard Oil Dev Co Nozzle process for making butyl rubber
US2513389A (en) * 1944-09-29 1950-07-04 Standard Oil Dev Co Solid oxidized polymer of alkyl pentadiene
US2514928A (en) * 1945-04-30 1950-07-11 Shell Dev Polymerizing branch-chain hexadienes
US2514979A (en) * 1947-04-16 1950-07-11 Atlantic Refining Co Wax composition containing propylene-butadiene polymer
US2523150A (en) * 1946-09-28 1950-09-19 Standard Oil Dev Co Resinous copolymers of diolefins with refinery c. cuts
US2529322A (en) * 1947-08-20 1950-11-07 Standard Oil Dev Co Process of preparing synthetic drying oils
US2534095A (en) * 1948-03-31 1950-12-12 Standard Oil Dev Co Hydrocarbon copolymers and use thereof as lube oil additive
US2536841A (en) * 1945-12-04 1951-01-02 Standard Oil Dev Co Low-temperature olefin polymerization with sulfur containing friedel-crafts complex catalysts
US2539824A (en) * 1945-04-20 1951-01-30 Standard Oil Dev Co Nitration derivatives of hydrocarbon copolymers
US2542286A (en) * 1944-09-26 1951-02-20 Shell Dev Lubricating oil containing chlorinated cyclic polymer
US2549539A (en) * 1945-09-14 1951-04-17 Standard Oil Dev Co Styrene-diolefin low temperature copolymers and preparation and uses thereof
US2551641A (en) * 1951-05-08 Process of reacting alpha-mono ole
US2554245A (en) * 1946-09-17 1951-05-22 Standard Oil Dev Co Complex friedel-crafts catalyst containing aromatic hydrocarbons
US2565960A (en) * 1946-07-06 1951-08-28 Standard Oil Dev Co Preparation of an improved hydrocarbon resin
US2571354A (en) * 1949-01-22 1951-10-16 Socony Vacuum Oil Co Inc Polymerization of monoalkylethylenes
US2578169A (en) * 1948-11-24 1951-12-11 Universal Oil Prod Co Copolymers of an ethylenically unsaturated compound with a polyolefinic cyclic hydrocarbon
US2583420A (en) * 1945-07-17 1952-01-22 Standard Oil Dev Co Controlling heat of reaction by refluxing in the butadiene-diisobutylene copolymerization
US2583504A (en) * 1946-07-08 1952-01-22 Standard Oil Dev Co Process for preparing isoolefindiolefin copolymers of uniform average composition
US2585867A (en) * 1948-03-05 1952-02-12 Jasco Inc Process for polymerizing isoolefins using methyl chloride solution of bf as catalyst
US2589069A (en) * 1948-06-04 1952-03-11 Standard Oil Dev Co Making resins from olefin polymers and organic acid anhydride
US2608550A (en) * 1947-01-08 1952-08-26 Interchem Corp Reaction products of unsaturated dicarboxylic acid derivatives with cyclopentadiene polymers
US2611788A (en) * 1948-02-18 1952-09-23 Universal Oil Prod Co Modification of drying oils
US2615881A (en) * 1951-10-04 1952-10-28 Standard Oil Dev Co Polymethylpentadiene synthetic rubber
US2634256A (en) * 1949-02-15 1953-04-07 Standard Oil Dev Co Modified olefin-diolefin resin
US2660563A (en) * 1949-07-28 1953-11-24 Standard Oil Dev Co Mineral oil containing substituted polyolefins
US2669554A (en) * 1952-06-18 1954-02-16 Colloid Chemical Lab Inc Method of treating cashew nut shell liquid with fluoboric acid
US2682531A (en) * 1951-03-31 1954-06-29 Standard Oil Dev Co Zirconium tetrachloride-ether complexes as low temperature polymerization catalyst
US2697694A (en) * 1950-10-28 1954-12-21 Standard Oil Co Manufacture of high molecular weight polybutenes
US2720479A (en) * 1951-06-30 1955-10-11 Goodrich Co B F Method of bonding using brominated isomonoolefin polyolefin interpolymer adhesive compositions and article produced thereby
US2748090A (en) * 1955-02-28 1956-05-29 Universal Oil Prod Co Manufacture of solid polymerization catalysts
US2801273A (en) * 1951-12-31 1957-07-30 Exxon Research Engineering Co Polymerization of olefins
US2824859A (en) * 1953-03-18 1958-02-25 Exxon Research Engineering Co Production of resins by reaction of maleic anhydride with steam-cracked fractions
US2830958A (en) * 1955-04-27 1958-04-15 Universal Oil Prod Co Preparation of solid composites
US2830959A (en) * 1955-04-27 1958-04-15 Universal Oil Prod Co Catalyst compositions
US2836586A (en) * 1953-05-27 1958-05-27 Monsanto Chemicals Polybutadiene-crotonic adducts
US2845403A (en) * 1954-06-02 1958-07-29 Us Rubber Co Maleic anhydride modified butyl rubber
US2856445A (en) * 1953-03-31 1958-10-14 Exxon Research Engineering Co Polymerization of olefins
US2858281A (en) * 1954-01-22 1958-10-28 Goodrich Co B F Insoluble, acid and alkali-resistant carboxylic polymers
US2882289A (en) * 1954-11-24 1959-04-14 Universal Oil Prod Co Alkylation process and catalyst therefor
US2886535A (en) * 1956-07-30 1959-05-12 Universal Oil Prod Co Catalyst compositions
US2901432A (en) * 1956-10-26 1959-08-25 Exxon Research Engineering Co Copolymers of propylene and piperylene as grease thickeners
US2903433A (en) * 1956-06-14 1959-09-08 Universal Oil Prod Co Preparation of solid catalyst composites
US2921032A (en) * 1955-04-27 1960-01-12 Universal Oil Prod Co Catalyst composition
US2931791A (en) * 1955-05-23 1960-04-05 Exxon Research Engineering Co Polymerization of hydrocarbons with catalyst of bf3 and bci3
US2952646A (en) * 1957-05-02 1960-09-13 Socony Mobil Oil Co Inc Synthetic resin and method of producing the same
US2973344A (en) * 1957-12-11 1961-02-28 Exxon Research Engineering Co Modified polymers
US2977347A (en) * 1956-12-24 1961-03-28 Exxon Research Engineering Co Polymerization of olefins with molybdenum pentachloride catalyst
US2984649A (en) * 1956-06-26 1961-05-16 Exxon Research Engineering Co Modification of butyl rubber by treatment with organic acid anhydride
US2989506A (en) * 1957-10-21 1961-06-20 Celanese Corp Catalytic polymerization
US2989511A (en) * 1958-12-23 1961-06-20 Celanese Corp Catalytic polymerization of trioxane
US2993880A (en) * 1954-12-16 1961-07-25 Exxon Research Engineering Co Cross-linked maleic anhydride modified petroleum resin
US3005807A (en) * 1956-11-19 1961-10-24 Exxon Research Engineering Co Process for carboxylation of isoolefindiolefin copolymers
US3005800A (en) * 1958-04-01 1961-10-24 Paul O Powers Method of maleinizing petroleum resin
US3018264A (en) * 1957-11-25 1962-01-23 Union Carbide Corp Polyepoxide compositions
US3033832A (en) * 1958-03-07 1962-05-08 Exxon Research Engineering Co Halogenation of rubbery copolymers
US3081283A (en) * 1959-10-07 1963-03-12 Cities Service Res & Dev Co Polymerization and coating processes and products
US3200096A (en) * 1957-10-21 1965-08-10 Celanese Corp Catalytic polymerization of trioxane
US3202679A (en) * 1961-06-30 1965-08-24 California Research Corp Preparation of alkenyl succinic anhydrides
US3206432A (en) * 1961-05-15 1965-09-14 Shell Oil Co Modified polymers
US3215672A (en) * 1960-06-17 1965-11-02 Shell Oil Co Polymerization of unsaturated monomers with catalysts of neutral metal halide salts
US3216885A (en) * 1962-01-03 1965-11-09 Union Carbide Corp Printing ink comprising carboxylic acid modified polyethylene wax
US3320226A (en) * 1966-04-26 1967-05-16 Montedison Spa Dye-receptive polyolefin fibers containing saturated, unsubstituted dicarboxylic acid or acid anhydride
US3344067A (en) * 1964-12-28 1967-09-26 Standard Oil Co Derivatives of copolymers of isobutene and conjugated dienes
US3349148A (en) * 1963-10-09 1967-10-24 Shell Oil Co Polymerization process
US3359154A (en) * 1961-12-11 1967-12-19 Union Carbide Corp Polyolefin adhesion
US3450559A (en) * 1965-11-02 1969-06-17 Union Carbide Corp Fibers and fabrics finished with a dicarboxylic reagent modified polyolefin wax
US3457173A (en) * 1962-10-02 1969-07-22 Union Carbide Corp Aqueous lubricants containing siloxane-polyoxyalkylene compositions
US3475338A (en) * 1966-10-13 1969-10-28 Sinclair Research Inc Process of cutting metals and cutting oil containing allylic hydroxyl-terminated unsaturated diene polymer
US3501404A (en) * 1969-05-05 1970-03-17 Union Carbide Corp Aqueous lubricants for metal working
US3522180A (en) * 1967-09-28 1970-07-28 Texaco Inc Lubricating oil compositions containing amorphous ethylene-propylene copolymers
US3535290A (en) * 1968-01-12 1970-10-20 Gulf Research Development Co Process for preparing polymeric anhydrides
DE1769834A1 (de) * 1967-07-31 1971-10-14 Esso Res And Engineering Co OElzubereitung
US3953407A (en) * 1973-07-16 1976-04-27 Nippon Oil Co., Ltd. Process for preparing paper size resin
US4024203A (en) * 1969-11-24 1977-05-17 Institut Francais Du Petrole Oligomerization of unsaturated hydrocarbons with acid catalysts
US4833210A (en) * 1984-10-02 1989-05-23 Mitsubishi Petrochemical Co., Ltd. Modified copolymer

Cited By (90)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2551641A (en) * 1951-05-08 Process of reacting alpha-mono ole
US2418797A (en) * 1939-04-01 1947-04-08 Standard Oil Co Continuous process for polymerizing olefins
US2442218A (en) * 1941-08-27 1948-05-25 Jasco Inc Interpolymers of isoolefine with diolefins and process of producing same
US2417093A (en) * 1941-09-06 1947-03-11 Jasco Inc Sulfurized, milled, and cured polymer
US2446897A (en) * 1942-12-24 1948-08-10 Standard Oil Dev Co Process for polymerizing olefinic compounds with metal halide-organic acid double salts
US2443287A (en) * 1943-05-15 1948-06-15 Standard Oil Dev Co Polymerization catalyst
US2468523A (en) * 1943-06-10 1949-04-26 Standard Oil Dev Co Delayed-action polymerization process
US2491710A (en) * 1943-06-16 1949-12-20 Standard Oil Dev Co Nozzle process for making butyl rubber
US2422278A (en) * 1943-12-01 1947-06-17 Standard Oil Dev Co Lubricating oil composition
US2447610A (en) * 1943-12-07 1948-08-24 Standard Oil Dev Co Solid halogen derivatives of polymerized methyl pentadiene
US2456228A (en) * 1943-12-08 1948-12-14 Libbey Owens Ford Giass Compan Method of dispersing a solid polymerization catalyst in a polymerizable thermosetting resin sirup
US2431461A (en) * 1943-12-16 1947-11-25 Standard Oil Dev Co Olefinic polymerization pretreatment
US2439610A (en) * 1944-09-26 1948-04-13 Shell Dev Stabilized organic composition
US2542286A (en) * 1944-09-26 1951-02-20 Shell Dev Lubricating oil containing chlorinated cyclic polymer
US2513389A (en) * 1944-09-29 1950-07-04 Standard Oil Dev Co Solid oxidized polymer of alkyl pentadiene
US2477018A (en) * 1944-12-30 1949-07-26 Standard Oil Dev Co Synthetic rubbery copolymers of normal olefins with diolefins
US2539824A (en) * 1945-04-20 1951-01-30 Standard Oil Dev Co Nitration derivatives of hydrocarbon copolymers
US2514928A (en) * 1945-04-30 1950-07-11 Shell Dev Polymerizing branch-chain hexadienes
US2583420A (en) * 1945-07-17 1952-01-22 Standard Oil Dev Co Controlling heat of reaction by refluxing in the butadiene-diisobutylene copolymerization
US2549539A (en) * 1945-09-14 1951-04-17 Standard Oil Dev Co Styrene-diolefin low temperature copolymers and preparation and uses thereof
US2465292A (en) * 1945-10-19 1949-03-22 Standard Oil Dev Co Chemical process
US2536841A (en) * 1945-12-04 1951-01-02 Standard Oil Dev Co Low-temperature olefin polymerization with sulfur containing friedel-crafts complex catalysts
US2442643A (en) * 1946-04-02 1948-06-01 California Research Corp Process of activating polymerization of hydrocarbons
US2442644A (en) * 1946-04-02 1948-06-01 California Research Corp Method of controlling viscosity of hydrocarbon polymers
US2565960A (en) * 1946-07-06 1951-08-28 Standard Oil Dev Co Preparation of an improved hydrocarbon resin
US2583504A (en) * 1946-07-08 1952-01-22 Standard Oil Dev Co Process for preparing isoolefindiolefin copolymers of uniform average composition
US2554245A (en) * 1946-09-17 1951-05-22 Standard Oil Dev Co Complex friedel-crafts catalyst containing aromatic hydrocarbons
US2523150A (en) * 1946-09-28 1950-09-19 Standard Oil Dev Co Resinous copolymers of diolefins with refinery c. cuts
US2608550A (en) * 1947-01-08 1952-08-26 Interchem Corp Reaction products of unsaturated dicarboxylic acid derivatives with cyclopentadiene polymers
US2514979A (en) * 1947-04-16 1950-07-11 Atlantic Refining Co Wax composition containing propylene-butadiene polymer
US2529322A (en) * 1947-08-20 1950-11-07 Standard Oil Dev Co Process of preparing synthetic drying oils
US2611788A (en) * 1948-02-18 1952-09-23 Universal Oil Prod Co Modification of drying oils
US2585867A (en) * 1948-03-05 1952-02-12 Jasco Inc Process for polymerizing isoolefins using methyl chloride solution of bf as catalyst
US2534095A (en) * 1948-03-31 1950-12-12 Standard Oil Dev Co Hydrocarbon copolymers and use thereof as lube oil additive
US2589069A (en) * 1948-06-04 1952-03-11 Standard Oil Dev Co Making resins from olefin polymers and organic acid anhydride
US2578169A (en) * 1948-11-24 1951-12-11 Universal Oil Prod Co Copolymers of an ethylenically unsaturated compound with a polyolefinic cyclic hydrocarbon
US2571354A (en) * 1949-01-22 1951-10-16 Socony Vacuum Oil Co Inc Polymerization of monoalkylethylenes
US2634256A (en) * 1949-02-15 1953-04-07 Standard Oil Dev Co Modified olefin-diolefin resin
US2660563A (en) * 1949-07-28 1953-11-24 Standard Oil Dev Co Mineral oil containing substituted polyolefins
US2697694A (en) * 1950-10-28 1954-12-21 Standard Oil Co Manufacture of high molecular weight polybutenes
US2682531A (en) * 1951-03-31 1954-06-29 Standard Oil Dev Co Zirconium tetrachloride-ether complexes as low temperature polymerization catalyst
US2720479A (en) * 1951-06-30 1955-10-11 Goodrich Co B F Method of bonding using brominated isomonoolefin polyolefin interpolymer adhesive compositions and article produced thereby
US2615881A (en) * 1951-10-04 1952-10-28 Standard Oil Dev Co Polymethylpentadiene synthetic rubber
US2801273A (en) * 1951-12-31 1957-07-30 Exxon Research Engineering Co Polymerization of olefins
US2669554A (en) * 1952-06-18 1954-02-16 Colloid Chemical Lab Inc Method of treating cashew nut shell liquid with fluoboric acid
US2824859A (en) * 1953-03-18 1958-02-25 Exxon Research Engineering Co Production of resins by reaction of maleic anhydride with steam-cracked fractions
US2856445A (en) * 1953-03-31 1958-10-14 Exxon Research Engineering Co Polymerization of olefins
US2836586A (en) * 1953-05-27 1958-05-27 Monsanto Chemicals Polybutadiene-crotonic adducts
US2858281A (en) * 1954-01-22 1958-10-28 Goodrich Co B F Insoluble, acid and alkali-resistant carboxylic polymers
US2845403A (en) * 1954-06-02 1958-07-29 Us Rubber Co Maleic anhydride modified butyl rubber
US2882289A (en) * 1954-11-24 1959-04-14 Universal Oil Prod Co Alkylation process and catalyst therefor
US2993880A (en) * 1954-12-16 1961-07-25 Exxon Research Engineering Co Cross-linked maleic anhydride modified petroleum resin
US2748090A (en) * 1955-02-28 1956-05-29 Universal Oil Prod Co Manufacture of solid polymerization catalysts
US2830959A (en) * 1955-04-27 1958-04-15 Universal Oil Prod Co Catalyst compositions
US2921032A (en) * 1955-04-27 1960-01-12 Universal Oil Prod Co Catalyst composition
US2830958A (en) * 1955-04-27 1958-04-15 Universal Oil Prod Co Preparation of solid composites
US2931791A (en) * 1955-05-23 1960-04-05 Exxon Research Engineering Co Polymerization of hydrocarbons with catalyst of bf3 and bci3
US2903433A (en) * 1956-06-14 1959-09-08 Universal Oil Prod Co Preparation of solid catalyst composites
US2984649A (en) * 1956-06-26 1961-05-16 Exxon Research Engineering Co Modification of butyl rubber by treatment with organic acid anhydride
US2886535A (en) * 1956-07-30 1959-05-12 Universal Oil Prod Co Catalyst compositions
US2901432A (en) * 1956-10-26 1959-08-25 Exxon Research Engineering Co Copolymers of propylene and piperylene as grease thickeners
US3005807A (en) * 1956-11-19 1961-10-24 Exxon Research Engineering Co Process for carboxylation of isoolefindiolefin copolymers
US2977347A (en) * 1956-12-24 1961-03-28 Exxon Research Engineering Co Polymerization of olefins with molybdenum pentachloride catalyst
US2952646A (en) * 1957-05-02 1960-09-13 Socony Mobil Oil Co Inc Synthetic resin and method of producing the same
US3200096A (en) * 1957-10-21 1965-08-10 Celanese Corp Catalytic polymerization of trioxane
US2989506A (en) * 1957-10-21 1961-06-20 Celanese Corp Catalytic polymerization
US3018264A (en) * 1957-11-25 1962-01-23 Union Carbide Corp Polyepoxide compositions
US2973344A (en) * 1957-12-11 1961-02-28 Exxon Research Engineering Co Modified polymers
US3033832A (en) * 1958-03-07 1962-05-08 Exxon Research Engineering Co Halogenation of rubbery copolymers
US3005800A (en) * 1958-04-01 1961-10-24 Paul O Powers Method of maleinizing petroleum resin
US2989511A (en) * 1958-12-23 1961-06-20 Celanese Corp Catalytic polymerization of trioxane
US3081283A (en) * 1959-10-07 1963-03-12 Cities Service Res & Dev Co Polymerization and coating processes and products
US3215672A (en) * 1960-06-17 1965-11-02 Shell Oil Co Polymerization of unsaturated monomers with catalysts of neutral metal halide salts
US3206432A (en) * 1961-05-15 1965-09-14 Shell Oil Co Modified polymers
US3202679A (en) * 1961-06-30 1965-08-24 California Research Corp Preparation of alkenyl succinic anhydrides
US3359154A (en) * 1961-12-11 1967-12-19 Union Carbide Corp Polyolefin adhesion
US3216885A (en) * 1962-01-03 1965-11-09 Union Carbide Corp Printing ink comprising carboxylic acid modified polyethylene wax
US3457173A (en) * 1962-10-02 1969-07-22 Union Carbide Corp Aqueous lubricants containing siloxane-polyoxyalkylene compositions
US3349148A (en) * 1963-10-09 1967-10-24 Shell Oil Co Polymerization process
US3344067A (en) * 1964-12-28 1967-09-26 Standard Oil Co Derivatives of copolymers of isobutene and conjugated dienes
US3450559A (en) * 1965-11-02 1969-06-17 Union Carbide Corp Fibers and fabrics finished with a dicarboxylic reagent modified polyolefin wax
US3320226A (en) * 1966-04-26 1967-05-16 Montedison Spa Dye-receptive polyolefin fibers containing saturated, unsubstituted dicarboxylic acid or acid anhydride
US3475338A (en) * 1966-10-13 1969-10-28 Sinclair Research Inc Process of cutting metals and cutting oil containing allylic hydroxyl-terminated unsaturated diene polymer
DE1769834A1 (de) * 1967-07-31 1971-10-14 Esso Res And Engineering Co OElzubereitung
US3522180A (en) * 1967-09-28 1970-07-28 Texaco Inc Lubricating oil compositions containing amorphous ethylene-propylene copolymers
US3535290A (en) * 1968-01-12 1970-10-20 Gulf Research Development Co Process for preparing polymeric anhydrides
US3501404A (en) * 1969-05-05 1970-03-17 Union Carbide Corp Aqueous lubricants for metal working
US4024203A (en) * 1969-11-24 1977-05-17 Institut Francais Du Petrole Oligomerization of unsaturated hydrocarbons with acid catalysts
US3953407A (en) * 1973-07-16 1976-04-27 Nippon Oil Co., Ltd. Process for preparing paper size resin
US4833210A (en) * 1984-10-02 1989-05-23 Mitsubishi Petrochemical Co., Ltd. Modified copolymer

Also Published As

Publication number Publication date
NL30648C (xx)
NL21223C (xx)
NL43011C (xx)

Similar Documents

Publication Publication Date Title
US2142980A (en) High molecular weight polar compounds and process of making the same
US2220099A (en) Sulphonic acids
US2181640A (en) Process and products relating to production of valuable hydrocarbons
US2092295A (en) Production of synthetic resins and resinous materials
US2379728A (en) Methods of preparing polymerization products
US2318719A (en) Method for polymerizing olefins to lubricating oils
US2052268A (en) Production of valuable products from unsaturated compounds and hydrogen sulphide
US2324784A (en) Condensation product and method of preparing and using same
US5284988A (en) Preparation of synthetic oils from vinylidene olefins and alpha-olefins
US4041098A (en) Method for the oligomerization of alpha-olefins
US2130084A (en) Halo-substitution of unsaturated organic compounds
US2810769A (en) Production of long chain alkyl substituted aromatic hydrocarbons
US2419500A (en) Production of halogenated compounds
GB2078776A (en) Method for producing fluid for use as lubricating oil
US3842134A (en) Polymerization process
US2253323A (en) Production of drying oils
US2375315A (en) Interface modifier
US2259934A (en) Oil-soluble high-molecular weight compounds and process for their preparation
US2342074A (en) Hydrocarbon mixture
US2780664A (en) Hydrocarbon drying oil
US2143566A (en) Process for the manufacture of lubricants
US2174246A (en) Method for producing wax modifying agents
US4395578A (en) Oligomerization of olefins over boron trifluoride in the presence of a transition metal cation-containing promoter
US2551638A (en) Production of lubricating oils by condensation of olefinic hydrocarbons
US2401933A (en) Polymerization of olefins to oily polymers