• Abstract and Figures
• Public Full-text

Patented Nov. 11, 1941 2,262,743 UNITED STATES PATENT of FICE 2,262,743 PROCESS FOR BREAKING PETROLEUR EMUSIONS Melvin De Groote, University City, and Bernhard Keiser and Charles M. Blair, Jr., Webster Groves, Mo., assignors to Petroite Corporation, Ltd., Wilmington, Del, a corporation of Dela Ware No Drawing. Application May 12, 194i, Serial No. 393,128 4 Claims. (C1. 252-344) This invention relates primarily to the resolu ous chemical compounds adapted for use in tion of petroleum emulsions, our present appli breaking oil field emulsions, reference was made cation being a continuation, in part, of Our co to a type exemplified by the following formula: pending application Serial No. 342,716, filed June. N-CH 27, 1940. 2 One object of our invention is to provide a Ciuc, novel process for resolving petroleum emulsions NH-CI of the water-in-oil type that are commonly re In regard to such compounds, it is pointed out ferred to as 'cut oil,' 'roily oil,' 'emulsified oil,' in said co-pending application Serial No. 342,716, etc., and which comprise fine droplets of nat 10 that the oxyalkylated derivatives may be emi urally-occurring waters or brines dispersed in a ployed, This fact is stated in the following.lan more or less permanent state throughout the oil guage: which constitutes the continuous phase of the "Also, as is well known, any of the diamines emulsion. w of the kind previously described containing at Another object of our invention is to provide s least one amino hydrogen atom may be con a: economical and rapid process for separating verted into hydroxylated derivatives by reaction emulsions which have been prepared under con with an alkylene oxide, such as ethylene oxide, trolled conditions from mineral oil, such as crude propylene Oxide, glycidol, epichlorhydrin, and the petroleum and relatively soft waters or weak like. As to the general procedure employed, al brines. Controlled emulsification and subsequent 20 though not concerned particularly with cyclic demulsification under the conditions just men amines or the like, reference is made to U. S. tioned is of significant value in removing im Patent No. 2,046,720, dated. July 7, 1936, to Bot purities, particularly inorganic salts, from pipe tons.' line Oil. The compounds herein contemplated are chair Incidentally, a compound of the kind herein acterized by the presence of a five-membered contemplated may be used as a break-inducer heterocyclic ring with two atoms different from and for doctor treatment of the kind intended carbon. More specifically, they may be consid to Sweeten gasoline. See U. S. Patent No. 2,- ered as derivatives of imidazole, frequently re 157,223, dated May 9, 1939, to Sutton. ferred to as glyoxaline. Inidazole (glyoxaline) Such compounds may also find utility in re 30 is indicated by the following formula: covering oil from Subterranean oil-bearing strata. See U. S. Patent No. 2,223,381, dated February EC-N 25, 1941, to De Groote and Keiser. Compounds of the type herein contemplated a are of particular value in preventing water-in 85 Y?, - oil emulsions resulting from acidization of cal The imidazolines or glyoxalidines may be con careous oil-bearing strata. See U. S. Patent No. sidered as dihydro-derivatives of amidazole (gly 2,233,383, dated February 25, 1941, to De Groote oxaline); and thus the expressions "dihydrogly and Keiser. Such specific application of de oxalines' and "glyoxalidines' are often em mulsifiers of the kind herein contemplated is 40 ployed. The introduction of two hydrogen atoms disclosed in our co-pending application Serial at the 4-5 position results in the conversion of No. 393,129, filed May 12, 1941. imidazole into dihydroglyoxaline, which may be . The chemical compounds herein contemplated indicated by the following formula: as demulsifying agents, are oxyalkyl derivatives of imidazolines. These types of materials and 45 BC-N the method of preparing the same are Well known. EC5 2CH For instance, see U. S. Patent No. 2,211,001, N1/ dated August 13, 1940, to Chwala. In our aforementioned co-pending application Serial No. 342,716, which is concerned with vari 50 AS to the manufacture of imidazolines, refer 2 2,262,743 ence is made to the following patents: U. S. other acids, mixed higher fatty acids derived Patents Nos. 2,215,861, 2,215,862, 2,215,863 and from animal or vegetable sources, for example, 2,215,864, dated September 24, 1940, to Wald lard, cocoanut oil, rapeseed oil, sesame oil, palm mann and Chwala. ------- kernel oil, palm oil, olive oil, corn oil, cottonseed Imidazolines or glyoxalidines may be regarded oil, Sardine oil, tallow, soyabean oil, peanut oil, as dehydration products of certain amides; and castor oil, seal oils, whale oil, shark oil and other they may be obtained by reacting polyamines. fish oils, teaseed oil, partially or completely hy and the higher carboxylic acids under certain drogenated animal and vegetable oils, such as conditions. The formation of these glyoxalidine these mentioned; hydroxy and alpha-hydroxy compounds, while forming no part of the pres O higher carboxylic, aliphatic and fatty acids, such ent invention, is indicated by the following as hydroxystearic acid, dihydroxypalmitic acid, Scheme: dihydroxystearic acid, dihydroxybehenic acid, O alphahydroxy capric acid, alphahydroxy stearic 2 -O acid, alphahydroxy palmitic acid, alpha hydroxy R.C-OH--H.N.C.H.C.H.R.N.H.R.X --> 5 lauric acid, alphahydroxy myristic acid, alpha Fatty acid Alkylene polyanine hydroxy Cocoanut oil mixed fatty acids, alpha O - hydroxy margaric acid, alphahydroxy arachidic 2 r. f -HO acid, and the like; fatty and Similar acids derived R.C.H.N.C.H.CH.R.N.H.R.XHO - from various waxes, such as beeswax, sper Amide 20 maceti, montan wax, Japan wax, coccerin, and carnauba, Wax. Such acids include carnaubic R-c e's CH acid, Cerotic acid, lacceric acid, montanic acid, . 2EO psyllastearic acid, etc. As suggested, one may X-RN C.R. also employ higher molecular weight carboxylic 1,2-disubstituted glyoxalidine 25 acids derived, by oxidation and other methods, wherein R represents an alkyl or alkenyl group from paraffin wax, petroleum and similar hydro containing from 10 to 20 carbon atoms (the res carbons; resinic and hydroaromatic acids, such idue of a higher fatty acid); Ri represents hy as hexahydrobenzoic acid, hydrogenated naph drogen or a lower alkyl group; R2 represents an thoic, hydrogenated carboxy-diphenyl, naph alkylene group or a lower alkyl substituted al 30 thenic, and abietic acid; aralkyl and aromatic kylene group; and X represents a hydroxyl group, acids, Such as hexahydrobenzoic acid, hydrogen an amino group, or an aminoalkylene substituted ated naphthoic, hydrogenated poly carboxy imino group. See U. S. Patent No. 2,214,152, diphenyl, naphthenic, and abietic acid; aralkyl dated September 10, 1940, to Wilkes. and aromatic acids, such as benzoic acid, See also U. S. Patents Nos. 2,55,877 and 35 Twitchell fatty acids, naphthoic acid, carboxy 2,155,878, both dated April 25, 1939, to Waldmann diphenyl, pyridine carboxylic acid, hydroxy and Chwala. benzoic acid, and the like. The expression "higher molecular weight car Other suitable acids include phenylstearic acid, boxy, acids' is an expression frequently employed benzoylnonylic acid, campholic acid, fencholic to refer to certain organic acids, particularly 40 acid, cetyloxybutyric acid, cetyloxyacetic acid, monocarboxy acids, having more than six car chlorStearic acid, etc. bon atoms, and generally, less than 40 carbon Another source of suitable acids are those com atons. The commonest examples include the monly referred to as lac acids, such, for example, detergent-forming acids, i. e., those acids which as the acids derived from shellac. Such acids combine with alkalies to produce soap or soap 45 include various polyhydroxy acids, for example, like bodies. The detergent-forming acids, in aleuritic acid, shelloic acid, and kerrolic acid. turn, include naturally-occurring fatty acids, As is well known, one may use substituted resin acids, Such as abietic acid, naturally-occur acids in which some other non-functional con ring petroleum acids, such as naphthenic acids, stituent enters the structure of the fatty acid. and carboxy acids produced by the oxidation of 50 For instance, one may use aryl-, hydroxy-, petroleum. As will be subsequently indicated, alkoxy-, chlor-, keto-, and amino-derivatives. there are other acids which have somewhat simi Generally Speaking, however, it is always prefer lar characteristics and are derived from some able to use the unsubstituted acid, particularly What different sources, and are different in struc free from substituents which contain either ture, but can be included in the broad generic 55 Oxygen or nitrogen atoms. Generally speaking, term previously indicated. the introduction of hydrocarbon radicals, regard Among Sources of such acids may be men less of Source, has little effect, except in altering tioned straight chain and branched chain, satu the hydrophile-hydrophobe balance. rated and unsaturated, carboxylic, aliphatic, ali One may also employ the blown or oxidized Cyclic, fatty, aromatic, hydroarmoatic, and O acids, such as blown ricinoleic acid, blown oleic, aralkyl acids including caprylic acid, butyric acid, etc., or estolides derived from blown oils, such heptylic acid, caproic acid, capric acid, pimelic as blown castor oil, blown soyabean oil, etc. acid, Sebacic acid, erucic acid, saturated and un Needless to say, the acids themselves need not Saturated higher molecular weight aliphatic be employed; but one may readily employ any acids, such as the higher fatty acids containing 65 functional equivalent, such as the anhydride, the at least eight carbon atoms, and including, in acyl chloride, or the like. In some instances, the addition to those mentioned, melissic acid, stearic esters, especially in presence of a trace or a acid, oleic acid, ricinoleic acid, diricinoleic acid, significant amount of water, act as the acid itself, triricinoleic acid, polyricinoleic acid, ricino in that the acid is liberated.

Load more

  4

Copy Link