Secondary Butyl Alcohol Research Articles

Effect of salinity and alcohol partitioning on phase behavior and oil displacement efficiency in surfactant‐polymer flooding

AbstractThe equivalent alkane carbon number (EACN) of a crude oil, namely Ankleshwar crude, is successfully modeled by a mixture of pure alkanes. The EACN of the crude oil is found to be 9.3, and an appropriate mixture of nonane and decane exhibited phase behavior similar to that of the crude oil. A surfactant system for a water flooded reservoir at 80 C and having a salinity in the range of 2% to 3% NaCl is formulated by blending a phosphated ester with a petroleum sulfonate in the weight ratio of 2/5. The addition of phosphate ester not only increases the salt tolerance of the petroleum sulfonate system, it also broadens the IFT minimum. The oil displacement tests at 80 C in sandpacks and Berea cores showed that the surfactant formulation containing tertiary amyl alcohol (TAA) displaced 92% oil in sandpacks and 79% crude oil in Berea cores. The oil recovery efficiency was poor when formulations contained other alcohols. From the effluent surfactant concentration, it is shown that there is a correlation between the tertiary oil recovery, surfactant breakthrough and surfactant retention in porous media. It is proposed that, because alcohols such as isopropyl alcohol (IPA), isobutyl alcohol (IBA) and secondary butyl alcohol (SBA) partition significantly in the equilibrated excess brine phase, the alcohol‐depleted surfactant slug forms stable emulsions resulting in faster breakthrough of surfactant in the effluent and lower oil displacement efficiency. In the case of TAA‐containing formulation, there is a partitioning of TAA in the oil phase. Therefore, there is a mass transfer of alcohol from surfactant slug to the oil ganglia in porous media. This produces a transient ultralow IFT between residual oil and the surfactant solution which mobilizes oil, resulting in higher oil displacement efficiency.

Study of relations governing the distribution of composition of reaction products of propylene oxide with alcohols

A study was made of the composition of reaction products of propylene oxide with methyl, ethyl, n- and isopropyl, normal and secondary butyl alcohols during catalysis with corresponding alcoholates. The molecular proportion of the initial alcohol and products of addition of 1–10 propylene oxide molecules to a corresponding alcohol was determined by GLC with an average number of oxide moles added of 0·5–5·0 per mole initial alcohol. By computer, ratios of rate constants of sequential stages of addition of oxide to alcohols were determined from experimental results. It was shown that constant ratios derived are related to the acidity of corresponding alcohols by the Brönsted equation. A satisfactory description of all experimental results by the equations derived enables them to be used to calculate the distribution of products of oxypropylation of alcohols of a known acidity.

Kinetics of Solvolyses of Various N, N'-Dialkyl-N-nitrosoureas in Neutral and Alkaline Solutions

a) The neutral and alkaline solvolyses of N-methyl-N'-p-fluorophenyl-N-nitrosourea, 1, 6-dimethyl-1, 6-dinitrosobiurea, N-methyl-N'-phenethyl-N-nitrosourea, trimethylenebis-N-methyl-N-nitrosourea and N, N'-dimethyl-N-nitrosourea are subject to spontaneous and specific hydroxide ion catalysis, i.e. kapp(sec-1=k0+kOH[OH-]. The decreasing order of reactivity is in the order given and is consistent with the fact that electron-with-drawing substituents abet hydroxyl ion attack by inducing a more positive center. The fact that substitution of an alkyl for a hydrogen on the N'-nitrogen inhibits hydrolysis favors the adjacent carbonyl carbon as the primary focus of hydroxide ion attack. b) The log k-pH profiles of N, N'-dimethyl-N-nitrosourea and 1, 6-dimethyl-1, 6-dinitrosobiurea show a deviation in the linearity of the alkaline branch which can be attributed to a kinetic pKa' where these compounds may exist as anions at higher pH values and thus be more resistant to hydroxide ion attack. c) The gas chromatographically analyzed alcohol products of alkaline degradation of N-alkyl-N'-nitrosourease are various in several cases and thus clearly implicate a potentiallu rearranging carbonium ion intermediate in the alkaline solvolyses of these compounds. The N-n-butyl compound gives a mixture of n-butyl-alcohol in 45% yield, and secondary butyl alcohol in 24% yield for pH values greater than 7.0. The fact that the N-isobutyl compound yields t-butyl alcohol (76%), sec-butyl alcohol (22%)and isobutyl alcohol (18%) also implicates a methyl shift. The N-alkyl-and N-benzyl-compounds yield only the corresponding alcohols.

Studies on conjugated hydrogenation: Nickel catalyst with alcohols

AbstractStudies have been made on the conjugated hydrogenation of peanut and safflower oils using nickel catalyst and with alcohols as hydrogen donors. Peanut oil was reduced with ethyl alcohol to a final iodine value of 64舑71 and the reaction is selective because little saturated acid is formed but some linoleic acid is retained. When the same oil is reduced with isopropyl or secondary butyl alcohols an iodine value of 蝤25 is reached while all linoleic acid has disappeared. With safflower oil and isopropyl alcohol an iodine value of 蝤46 is reached and the reaction is selective since all linoleic acid has disappeared. Thus the amount of monoene retained depends on initial unsaturation of the oil when a secondary alcohol is used as hydrogen donor.

Oil Recovery by Solvents Mutually Soluble in Oil and Water

Abstract A series of laboratory experiments was conducted in which oil was displaced from a porous medium by water-driven slugs of alcohol is or similar solvents. The solvents used were soluble to some degree in both oil and water and covered the range of solubilities from complete solubility in oil to complete solubility in water. Displacement experiments were conducted on 2- and 3 1/2-in. in diameter consolidated cores and 1- and 2-in. in diameter unconsolidated sand packs. The cores and sand packs ranged in length from 1 to 30 ft, and they were saturated with brine and crude or refined oils. The solvents used included ethyl alcohol, isopropyl alcohol (IPA), tertiary butyl alcohol (TBA), secondary butyl alcohol (SBA), n-amyl alcohol (NAA), methyl ethyl ketone, acetone and others. It was found that all of the oil present in a porous medium could be miscibly displaced by injecting a slug of mutual solvent and driving it with water. The oil-recovery efficiency was dependent uponthe relative solubilities of the solvent in oil and water, andthe distance traversed by the flood. For complete oil recovery from cores, a smaller amount of a preferentially oil-soluble solvent was required, compared to the amount of preferentially water-soluble solvent needed. The size of the solvent slug required varied inversely with the linear flooding-path length raised to the 0.65 power. Water-driven dual solvent combinations (an oil-soluble solvent slug followed by a water-soluble solvent slug) were found to effect complete oil recovery with less total solvent than any single solvent used. In these dual-solvent displacement experiments, the slug size required varied inversely with length raised to the 0.55 power. Based upon the experimental results, a theory was developed to describe the displacement of oil and water by mutual solvents, and equations are presented to predict the production history in a linear system. These equations take into account the properties of the solvents and the porous medium. Introduction Oil-recovery processes which utilize displacing fluids that are miscible with the reservoir fluids have been studied extensively in recent years. Because of the poor contact efficiency and high pressure requirements of the LPG-gas displacement process there has been considerable interest in the alcohol-water process, and a number of studies have been made on the recovery of oil through the use of solvents which are mutually soluble in oil and water. An investigation by Sievert, Dew and Conley indicated that the use of mutual solvents would be limited because the presence of water in a porous medium would cause a phase break in the leading edge of the displacing solvent. Their study also showed that, in consolidated cores containing only oil, the displacement of oil by a water- driven mutual-solvent slug of tertiary butyl alcohol (TBA) was affected by the viscosity ratios of the fluids involved. Gatlin and Slobod concluded that an isopropyl alcohol (IPA) slug acts as a miscible piston, completely displacing both oil and water until the alcohol content of the mixing zone falls below the concentration necessary to maintain miscibility. Their study was conducted on uniform unconsolidated sand packs. They concluded further that IPA could be used effectively to recover oil from a watered-out sand. In a paper by Taber, Kamath and Reed relating an investigation on sandstone cores, it was stated that the displacement of oil by mutual solvents, particularly. IPA, was not a miscible displacement and that no improvement in efficiency could be expected with increase in flooding-path length. However, their analytical analysis of the displacement mechanism using TBA is, in fact, one which indicates that the displacement is controlled by miscible mixing. SPEJ P. 129^

Evolution of Volatile Compounds in Ripening Raw and Pasteurized Milk Cheddar Cheese Observed by Gas Chromatography

Summary Gas chromatographic techniques were applied to the study of the volatile compounds in raw and pasteurized milk Cheddar cheese during the ripening process. The major volatile compounds in both types of Cheddar cheese are acetic acid, butyric acid, ethanol, methyl ethyl ketone, and secondary butyl alcohol. Acetylmethylcarbinol and diacetyl are also present, generally at trace levels. Acetic acid, acetylmethylcarbinol, ethanol, and diacetyl are detectable on the first day of ripening. The concentration of acetic acid and ethanol increased throughout ripening. Acetylmethylcarbinol decreased from its original level. Butyric acid, secondary butyl alcohol, and methyl ethyl ketone appeared later in the ripening period. This was generally true for both the raw and pasteurized milk cheese; however, the rate of change of these compounds was much faster in the raw milk cheese. Also, the compounds in the raw milk cheese increased to much higher levels than those in the pasteurized milk cheese. It is hypothesized that methyl ethyl ketone and secondary butyl alcohol arise from the dehydration of 2,3-butylene glycol which comes from acetylmethylcarbinol.

The activity of ribonuclease after digestion with carboxypeptidase

On incubating ribonuclease (RNase) with a crystalline carboxypeptides preparation, a number of amino acids were liberated. Of the 17 amino acids in the RNase molecule, all except cystine and proline have thus far been quantitatively determined as products of this hydrolytic reaction with no loss in the original activity of the RNase. During the early phases of the digestion, the activity of the RNase was increased. A separation of the digested from the undigested RNase molecules has been achieved by chromatography of the digests in secondary-butyl alcohol: water (3:1) at 3° C for 15 hours. The native RNase molecules did not migrate under these conditions and were quite stable, whereas the digested RNase molecules migrated and were less stable. The data obtained with this procedure correlates reasonably well with the amino acid determinations as a measure of the per cent of the RNase molecules digested. The extent of digestion thus far achieved approximates 80% of the RNase molecules present, with no loss in enzymic activity. It is calculated that approximately 15% of the amino acid residues which constitute RNase are not essential for the enzymic activity, but appear to be necessary for the stability of the molecule.

COUNTER-CURRENT DISTRIBUTION PROCEDURE FOR THE QUANTITATIVE-QUALITATIVE ANALYSIS OF SMALL AMOUNTS OF URINARY CORTICOSTEROIDS*

Introduction THE present paper is an extension of previous work on procedures for the qualitative-quantitative analysis of small samples of urinary steroids of adrenocortical and gonadal origin (1). It involves the use of countercurrent distribution discussed by Craig (2). The amount of thiosemicarbazide reactive material present is estimated by means of the thiosemicarbazide reaction which Evans and Gillam have shown to be useful for the detection of alpha-beta unsaturated ketones (3). ANALYTIC PROCEDURE 1. Reagents and apparatus: Thiosemicarbazide reagent (Eastman Kodak Company). A 0.1 molar thiosemicarbazide solution in 0.1 molar hydrochloric acid is prepared and filtered into a glass-stoppered bottle. It is stable at room temperature for several months. Ethanol, absolute (U. S. Industrial Chemicals Company) Chloroform, reagent grade. Sodium hydroxide, 0.1 N solution. Secondary butyl alcohol (Eastman Kodak Company, highest purity), redistilled in an all-glass apparatus. Iso-octane (2,2,4-trimethylpenta...

Odeur et constitution XIII. Synthèse du triméthyl‐1,1,5‐méthylène‐9‐bicyclo‐[3,3,1]‐nonanol‐5

AbstractIn the presence of HCl or BF3 dihydro‐α‐ionone undergoes cyclisation. In solutions in primary alcohols ROH, this cyclisation leads to bicyclic ethers V with a semicyclic double‐bond. In secondary butyl alcohol the bicyclic alcohol XII is produced. Bicyclic hydro‐carbones are formed as byproducts. In benzene solution BF3 forms an unsaturated bicyclic epoxyde XVII. The infrared spectra of some of these substances are discussed.

Petroleum Plant at Stanlow

A SMALL booklet, some eighty pages in length, and entitled "Britain's New Industry: Stanlow 1949", has been published by the Shell Chemical Manufacturing Co., Ltd., and describes the oil installation and refining plant at Stanlow, which was established on the south bank of the Manchester Ship Canal in 1922. The booklet deal with the production of various kinds of oils, wax cracking, ester salts ('Teepol'), and similar products and chemicals obtained from petroleum. It gives a popular account of the plant and processes, and is profusely illustrated. The cracking processes are described in outline, for example, that for the production of iso-propyl and secondary butyl alcohols. The uses of the products are described. The processes used in America are also outlined, such as the production from propylene of allyl chloride, which is a raw material for the manufacture of plastics and synthetic glycerol. Butylene gives butadiene, the main raw material for the manufacture of synthetic rubber. At the end of the book there is a simple scheme of the chemistry of the processes which may be of interest to elementary students of organic chemistry and to business men. The production is very lavish, many of the illustrations being in colour.

Internal Rotation IV. The Optical Activity and Isomerization Energy of the Rotational Isomers of D-Secondary Butyl Alcohol

The specific rotation of secondary butyl alcohol was measured in dilute solutions of cyclohexane at intervals of 5° between 20°C and 70°C inclusive. After corrections for solvent effect and change of refractive index with temperature had been made there remained a definite temperature dependence of the rotivity. Interpretation of the results on the basis of three optically active rotational isomers (two of equal energy and the third less stable) gave the rotivity of the third isomer as −21° and the sum of the other two as +21°. The heat of isomerization was found to be 803 cal. per mole. The concentrations of the three rotational isomers at 20° are calculated as 42.3 percent, 42.3 percent, and 15.3 percent.

The Stereochemistry of the Sulfation of Optically Active Secondary Butyl Alcohol

The Stereochemistry of the Sulfation of Optically Active Secondary Butyl Alcohol

The Optical Activity of Secondary Butyl Alcohol

A calculation of the optical activity of secondary butyl alcohol is presented based upon a one-electron model. The chromophoric electron is considered to be one of the nonbonding electrons on the oxygen atom. This electron is considered to be moving in a field of the other nuclei and electrons considered as charge distributions. The fields of the other electrons are obtained from the Slater type eigenfunctions for the various atoms. This amounts to a rough solution of the Hartree approximation for the chromophoric electron. The results obtained are somewhat larger or somewhat smaller than the experimental value depending on the exact orientation of the groups in their rotation about single bonds. The assignment of an absolute configuration in these calculations follows provided the exact orientation of the rotating groups is known. The orientations which we consider most likely lead to an assignment of the absolute configuration in agreement with that of Kuhn.

One-Electron Rotatory Power

It is shown that a single electron moving in a field of suitable dissymmetry can give rise to optical rotatory power in a medium containing molecules of this type. This effect is called one-electron rotatory power and is in striking contrast to the models developed by Born, Oseen, Gray and others in which a dynamic coupling between several electronic oscillators is responsible for the rotatory power. The detailed calculations are carried out for the potential function, V=12(k1x2+k2y2+k3z2)+Axyz,which shows rotatory power both quantum mechanically and classically. Next it is shown how fields of this type may be adapted to an approximate description of the field in which the chromophoric electrons of a molecule move, the constants k1, k2, k3 and A being largely determined by the average charge on the different atoms of the molecule as found from additivity of dipole moments due to the bonds in the molecule. As illustrations of the theory absolute calculations are made for the contribution of the nitrite group to the rotatory power of methyl phenyl carbinol nitrite which agrees satisfactorily with experimental data, for the phenyl group contribution of the same molecule and for the hydroxyl group contribution in secondary butyl alcohol. In the latter two instances the theoretical values are much too small but as there is a great deal of freedom in the choice of the configuration because of free rotation these results merely indicate need for more detailed calculations. The general quantum-mechanical theory of circular dichroism is developed and a quantum-mechanical derivation of Natanson's rule is given. The quantum-mechanical definition of Kuhn's ``anisotropy factor'' is given and an alternative measure of the contribution of an absorption band to rotatory power called the rotatory strength is defined and discussed. It is shown that spin magnetic moments may generally be neglected in calculation of rotatory power owing to the weakness of spin-orbit interaction. Interpretation of experiments of Schwab, Rost and Rudolph on the catalytic dehydration of butyl alcohol on active quartz is discussed and kinetic arguments advanced to show how the relative configuration of quartz and butyl alcohol may be inferred from such data. The relation of one-electron rotatory power to known dipole moment and solvent effects on rotatory power is briefly discussed.

Studies on Glass XII. Some New Heat Capacity Data for Organic Glasses. The Entropy and Free Energy of dl-Lactic Acid

Heat capacity measurements by the Nernst method have been made upon samples of secondary butyl alcohol and 3-methylhexane in the glassy and liquid condition and upon a sample of dl-lactic acid (1) in an incompletely crystallized state, (2) in the form of an acid glass and liquid, and (3) in the form of a mixed glass and liquid. From these results the specific heats and heat of fusion of pure crystalline dl-lactic acid also have been derived. The data for the several glasses and undercooled liquids show a rapid rise from the heat capacity characteristic of a crystalline solid to that for the liquid state within a transition region of about 10° and the nature of this transition region has been discussed. A calculation of the molal entropy and free energy of formation of liquid dl-lactic acid at 298.1°K yields 45.9 (±1.0) e.u. and —124,300±(2300) cal., respectively.

An Azeotropic Mixture of Secondary Butyl Alcohol and Secondary Butyl Bromide1

An Azeotropic Mixture of Secondary Butyl Alcohol and Secondary Butyl Bromide¹

Determination of Isopropyl Alcohol in Presence of Acetone, and of Methylethylketone in Presence of Secondary Butyl Alcohol

Determination of Isopropyl Alcohol in Presence of Acetone, and of Methylethylketone in Presence of Secondary Butyl Alcohol

A phyto-pharmacological study of some isomers

A phyto-pharmacological study was carried out much in the same way as the effects of cocaine were studied by Macht and Livingston. The influence of a number of isomeric drugs was studied on the roots of lupinus albus. The following structural chemical isomers were examined: normal propyl alcohol and isopropyl alcohol, primary butyl alcohol and secondary butyl alcohol; primary amyl alcohol and secondary amyl alcohol. It was found in every case that the normal or primary alcohols were more toxic to the growth of the lupine than the corresponding secondary alcohols.The following stereo-isomers were examined: laevogyrous camphor, dextrogyrous camphor and optically inactive camphor; quinin and quinidin; cinchonin and cinchonidin. It was found that laevogyrous camphor was more toxic than the dextro variety, while the inactive camphor produced an effect equivalent to the mean of the other two. Quinin (sulphate) which is laevogyrous was found to be more toxic than quinidin (sulphate) which is its dextrogyrous iso...

Societies and Academies

PARIS. Academy of Sciences, September 9.—M. Henri Becquerel in the chair.—The contact phenomena of phonolitic trachyte from Griounot, Cantal A. Lacroix.—Bi-secondary butylene chlorohydrin: Louis Henry. The secondary butyl alcohol, CH3—CH2—CH3(OH)CH3, was prepared synthetically from ethuimagnesium bromide and aldehyde; this was converted into the secondary iodide, and from this, by the action of alcoholic potash, symmetrical dimethylethylene was prepared. The chlorohydrin results from the interaction of this hydrocarbon and hypochlorous acid. Its physical properties are given.—The resistance of the air: M. Jouguet.—Contribution to the study of the alloys of cobalt and tin: F. Ducelliez. The present note deals with alloys containing between 57 per cent, and 66 per cent, of tin. The alloys are probably formed of a mixture of CoSn and Co3Sn2.—Celestite from Mokattam: M. Couyat.—Parasitic phanerogamic plants and nitrates: Marcel Mirande. Parasitic phanerogams without chlorophyll cannot absorb nitrates from their hosts. The green hemiparasites vary, some being capable of absorbing nitrates from the host, others not.—Variation in the ramification of umbels: H. Ricome.—The causes of the death of the young hippopotamus of the museum menagerie: E. L. Trouessart. The animal died from injuries to the head caused by the mother in repelling the young hippopotamus from the breast.—The culture of the turbot: R. Anthony.—The subterranean waters of the Basque country: E. A. Martel.