US3349141A - Detergent alkylate composition of secondary phenyl-substituted n-alkanes - Google Patents

Detergent alkylate composition of secondary phenyl-substituted n-alkanes Download PDF

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Publication number
US3349141A
US3349141A US338635A US33863564A US3349141A US 3349141 A US3349141 A US 3349141A US 338635 A US338635 A US 338635A US 33863564 A US33863564 A US 33863564A US 3349141 A US3349141 A US 3349141A
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Prior art keywords
phenyl
alkanes
substituted
alkane
detergent
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US338635A
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Sweeney William Alan
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Chevron USA Inc
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Chevron Research and Technology Co
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Priority to US338635A priority Critical patent/US3349141A/en
Priority to FR1819A priority patent/FR1420865A/fr
Priority to GB2204/65A priority patent/GB1041491A/en
Priority to DE1518622A priority patent/DE1518622B2/de
Priority to US676707A priority patent/US3487023A/en
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Publication of US3349141A publication Critical patent/US3349141A/en
Priority to JP45027480A priority patent/JPS504203B1/ja
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    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/22—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aromatic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
    • C07C15/02—Monocyclic hydrocarbons
    • C07C15/107—Monocyclic hydrocarbons having saturated side-chain containing at least six carbon atoms, e.g. detergent alkylates

Definitions

  • Detergent alkylate compositions consisting essentially of a mixture of secondary phenyl-substituted n-alkanes of 11]4 carbon atoms have excellent biodegradability and can be prepared in known fashion by a number of reactions.
  • Conventional reactions involve catalytic alkylation of benzenes or some other aryl compound, such as toluene or xylene, with either an n-alkene or an n-alkyl halide alkylating agent of the desired molecular Weight range, which can be derived from distillate cracking or wax cracking, catalytic dehydrogenation of n-parafiins, chlorination dehydrochlorination of n paraffins, ethylene polymerization and chlorination of n-parafiins.
  • the raw materials from which the straight-chain stock is to be derived may be subjected to iso-normal sep aration processes, such as molecular sieves and urea clathration to produce a more linear product than could otherwise be obtained.
  • the detergent alkylate is'prepared. its finished form meets the requirements of biodegradability, but does not possess the detergency effectiveness of the phenyl-substituted polypropylene derived detergents. It has now unexpectedly been found that the deficiency in detersive power is due to the widespread composition, particularly as to the isomer distribution that results when the aryl or aromatic compound is alkylated with the straight-chain stock. Mixtures of phenyl-substituted nalkanes are produced upon alkylation of benzene with a C C alkyl chloride or olefin mixture. These include the terminal or end-chain 2- and 3-phenyl alkanes, the intermediate 4-phenyl alkanes and the mid-chain 5-, 6-, and 7-phenyl alkanes.
  • the invention is based on the discovery that the presence of the terminal 2- and S-phenyl alkanes impairs the detersive effectiveness of the alkylate mixture, and that by increasing the proportion of the mid-chain 5-, 6- and 7-phenyl alkane isomers, detergency is enhanced.
  • detergent alkylate composition consisting essentially of secondary phenyl-substituted n-alkanes having 11 to 14 carbon atoms in the alkane portion of the molecule. At least 50% by weight of the composition consists of phenyl-substituted n-alkanes having 12 to 14 carbon atoms in the alkane portion of the molecule, a major proportion of which is mid-chain phenyl-substituted alkanes; 5 to 30%, preferably 5 to 15%, by Weight, of intermediate 4-phenyl alkane; and a minor proportion of 2- and 3-phenyl alkane below about 35%, generally below 20%, and preferably below 10%, by weight, of the G -C phenyl alkanes.
  • the 2- and 3phenyl undecanes can be tolerated in relatively large amounts. Indeed, these terminal phenyl alkanes manifest better detergency properties than the mid-chain 5- and 6-phenyl undecanes. Therefore, satisfactory detergent alkylate compositions can contain up to 50% by weight, generally below 30%, and often 5-10% by weight of phenyl-substituted undecanes, the remainder of the detergent alkylate having the characteristics described above.
  • the detergent alkylate compositions can be composed of the phenyl-substituted alkanes of a single number carbon fraction, for example, the phenyl isomers of dodecane, or of tridecane or of tetradecane, again the proportions of the various isomers being as specified above.
  • the alkylate mixture can be prepared from a mixture of at least two homologous carbon fractions, for example, a mixture of phenyl-substituted tridecanes and tetradecanes, again the proportions of the various position isomers and the content of phenylsubstituted n-alkanes being as specified above.
  • Homologous mixtures as above described are readily obtained by the process of alkylation.
  • one convenient way is to effect alkylations of benzene and chlorinated paraffins, or alkanes, in the presence of AlC1 catalyst.
  • the pararfin precursor materials obtained from paraffin-containing petroleum oil, and, if desired, subjected to a molecular sieve treatment, can be so selected as to correspond to a single number carbon fraction or to a blend of multiple number carbon fractions containing all of the C C homologs, the various homologs being present in approximately equal molar proportions.
  • the terminal 2- and 3-phenyl isomers of a given carbon number because of their higher boiling point, are separable from more centrally attached phenyl alkane isomers by simple distillation. Therefore, mixtures of phenyl alkanes can be prepared having the desired 2- and I l-phenyl alkane content by separating the 2- and 3-phenyl isomers from one fraction and the 2- and 3-phenyl alkane content from another fraction, the fractions remaining having a higher proportion of the more centrally phenyl attached isomers being combined.
  • a fraction containing phenyl undecanes and phenyl dodecanes is treated by distillation to lower the 2- and 3-phenyl dodecane content, and the resulting mixture combined with a mixture of phenyl tridecanes and tetradecanes, from which also the 2- and 3-phenyl tetradecanes have been removed.
  • the proportions of the various homologs can vary. In general, however, in any mixture of homologs, any one homolog will be present in a proportion of at least 25% by weight of the homologous mixture.
  • a detergent alkylate composition of a mixture of phenyl-substituted alkanes is contemplated, substantially all of said mixture consisting of phenyl-substituted alkanes containing 11 to 14 carbon atoms in the alkane portion of the molecule.
  • the said mixture is further characterized in that 5 to 30%, by weight, of the mixture is phenyl undecanes, while the remainder of the mixture consists of phenyl alkanes having 12 to 14 carbon atoms in the alkane portion of the molecule, and contains at least 25%, based on said remainder, each of phenyl (lodecanes, phenyl tridecanes and phenyl tetradecanes. Moreover, said remainder consists of at least about 45% of phenyl-substituted alkanes other than the 2-, 3- and 4- phenyl alkanes, the aggregate contentof 2- and 3-phenyl tetradecanes being less than 4 percent.
  • the detergency effectiveness of the alkylate compositions of the present invention is manifested by mixtures of. the sulfonate derivative, obtained in conventional fashion, 'with so-called heavy duty detergent builders, in which the sulfonate can be present in proportions of 10 to 30% by weight of the finished composition.
  • these detergent builders are principally condensed inorganic phosphate detergent salt builders, used in conjunction with nonsoap synthetic surfactants to produce heavy duty detergent compositions.
  • tripolyphosphate is essentially the sole condensed phosphate or is admixed with the other condensed phosphates, for example, 80% tripolyphosphate and.20% pyrophosphate.
  • compositions herein contemplated are those customarily present in heavy duty detergent formulations. These include, in weight amounts, based on the composition: an anticorrosion and stabilizing agent, such as sodium silicate, wherein the SiO -to-Na O ratio can range from /2 to /3,
  • an. antiredeposition agent such as sodium carboxymethyl cellulose, as described, for example, in US. Patent No. 2,568,334, proportions of about 1 to 3% being cited as illustrative
  • a foam modifier such as a monoor diethanolamide of a fatty acid, such as lauric isopropanolarnide, in proportions, for example, of 5%
  • a chemical bleaching agent such as sodium perborate or sodium per-carbonate, for example, in an amount of 2 to 5%
  • optical whiteners in amounts of the order of 0.1 to 0.2%, such as the triazinyl and.
  • aroylstilbenes benzidinesulpho'nes, bisbenzimidazoles, triazoles, and amino coumarins
  • sequestering agents in amounts, for example, of the order less than 1%, such as tetrasodium ethylene diamine
  • certain inorganic salts up to about 30%, such as inorganic sulfate, carbonate, or borate.
  • a significant test for determining the detersive effectiveness of a detergent, and the one used in obtaining the data below with the biodegradable detergent alkylate of the present invention is the so-called Hand Dishwashing Test. This test is based on a-procedure presented at the ASTM D-12 Subcommitteeon Detergents, March 10, 1959, New York, NY.
  • the dishes are smeared with molten, partially hydrogenated vegetable oils, melting point of 110- 115 F. (Crisco), treated with a dye, such as Sudan Red Dye to impart a uniform appearance to the grease.
  • a dye such as Sudan Red Dye
  • the water container is then placed above the dishpan in such a position that the distance between faucet outlet and bottom of the dishpan is 18 inches. Further, the dishpan is so placed that the stream of water strikes the center of the dishpan. The water from the container is drained into the dishpan with the water faucets fully open. This requires about 4560 seconds. When the dishpan is completely charged, washing of the dishes is begun.
  • a detergent formulation capable of washing at least twenty plates and preferably at least twenty-four plates is regarded as suitable.
  • the sulfonate is produced by sulionating the detergent alkylate intermediate, followed by neutralization with sodium hydroxide and drying.
  • the resulting sulfonate product is compounded into a built detergent composition analyzing as follows, by weight: 25% sodium alkylbenzene sulfonate, 40% trisodium polyphosphate, 7% sodium silicate, 1% carboxy methyl cellulose, 19% sodium sulfate, and 8% water.
  • Experiment 1 represents a phenyl alkane mixture obtained by the alkylation reaction of benzene and chlorinated parafiins having 11 to 14 carbon atoms.
  • the sulfonate of the alkylate when compounded into a heavy duty detergent composition as described above washes eighteen dishes. It will be noted that the 2- and 3-phenyl C C alkanes content is 45.8%. Progressively lowering the 2- and 3-phenyl alkane content gives increasingly better results as shown in Experiments 25.
  • a detergent alkylate composition consisting essentially of secondary phenyl-substituted n-alkanes, 5 to 50% by weight of said phenyl-substituted n-alkanes having 11 carbon atoms in the alkane portion of the molecule, the remainder of said phenyl-substituted n-alkane having 12 to 14 carbon atoms in the alkane portion of the molecule, said remainder consisting of a major proportion of mid-chain substituted phenyl alkanes, from 5 to 30% by weight of 4-phenyl alkanes, and a minor proportion of 2- and 3-phenyl alkanes not exceeding about 35% by weight.
  • composition according to claim 1 wherein the C C 4-phenyl alkanes range from 5 to 15 percent.
  • a detergent alkylate composition consisting essentially of secondary phenyl-substituted n-alkanes having 11 to 14 carbon atoms in the alkane portion of the molecule, at least 50% by weight of said composition being a mixture of secondary phenyl-substituted n-alkanes of at least two homologous fractions selected from the group consisting of C C and C n-alkane homologous fractions, at major proportion of said mixture consisting of mid-chain phenyl-substituted n-alkanes, from 5 to by weight of 4-phenyl-substituted alkanes and a minor proportion of 2- and 3-phenyl alkanes not exceeding by weight.
  • composition according to claim 5 wherein the composition contains 5 to 50% by weight of phenyl-substituted alkanes containing 11 carbon atoms in the alkane portion.
  • a detergent alkylate composition consisting essentially of a mixture of phenyl-substituted alkanes, substantially all of the mixture consisting of phenyl-substituted alkanes containing 11 to 14 carbon atoms in the alkane portion of the molecule, 5 to 30% of the mixture consisting of phenyl undecanes, substantially all of the remainder of the mixture consisting of phenyl alkanes containing 12 to 14 carbon atoms in the alkane portion of the molecule and containing at least 25% each of phenyl dodecanes, phenyl tridecanes and phenyl tetradecanes, said remainder consisting of at least of phenyl-substituted alkanes other than the 2-, 3- and 4- phenyl alkanes, and said remainder having an aggregate content of 2- and 3-phenyl tetradecanes less than 4 percent.
  • a detergent alkylate composition consisting essentially of secondary phenyl-substituted n-alkane within the range of 11 to 14 carbon atoms in the alkane portion of the molecule with at least by weight of said composition composed of secondary phenyl-substituted nalkanes wherein the alkane portion contains 12, 13 and 14 carbon atoms and in which the phenyl attachment to said n-alkane is predominantly in the 4, 5, 6 and 7 position and a minor proportion of 2- and 3-phenyl alkanes in the phenyl-substituted C -C n-alkane portion of said composition which does not exceed 35% by weight.
  • composition according to claim 8 wherein the 2- and 3-phenyl alkanes of the phenyl-substituted C -C n-alkane portion of said composition does not exceed 20 percent.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Detergent Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US338635A 1964-01-20 1964-01-20 Detergent alkylate composition of secondary phenyl-substituted n-alkanes Expired - Lifetime US3349141A (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
US338635A US3349141A (en) 1964-01-20 1964-01-20 Detergent alkylate composition of secondary phenyl-substituted n-alkanes
FR1819A FR1420865A (fr) 1964-01-20 1965-01-18 Composition détergente de n-alcanes supérieurs phényl-substitués
GB2204/65A GB1041491A (en) 1964-01-20 1965-01-18 Detergent alkylate composition of secondary phenyl-substituted n-alkanes
DE1518622A DE1518622B2 (de) 1964-01-20 1965-01-19 Gemisch von Sulfonaten linearer, isomerer Alkylbenzole mit Wasch- und Reinigungsmitteleigenschaften
US676707A US3487023A (en) 1964-01-20 1967-10-20 Detergent compositions of sulfonated secondary phenyl-substituted n-alkanes
JP45027480A JPS504203B1 (enrdf_load_stackoverflow) 1964-01-20 1970-04-02

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US338635A US3349141A (en) 1964-01-20 1964-01-20 Detergent alkylate composition of secondary phenyl-substituted n-alkanes
US676707A US3487023A (en) 1964-01-20 1967-10-20 Detergent compositions of sulfonated secondary phenyl-substituted n-alkanes

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US676707A Expired - Lifetime US3487023A (en) 1964-01-20 1967-10-20 Detergent compositions of sulfonated secondary phenyl-substituted n-alkanes

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DE (1) DE1518622B2 (enrdf_load_stackoverflow)
FR (1) FR1420865A (enrdf_load_stackoverflow)
GB (1) GB1041491A (enrdf_load_stackoverflow)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3426092A (en) * 1967-11-20 1969-02-04 Universal Oil Prod Co Method for producing detergent-grade alkylate
US3487023A (en) * 1964-01-20 1969-12-30 Chevron Res Detergent compositions of sulfonated secondary phenyl-substituted n-alkanes
US4162236A (en) * 1978-01-05 1979-07-24 Monsanto Company Detergent compositions containing mixtures of alkylbenzene sulfonates as the detergent active
US4687593A (en) * 1984-12-17 1987-08-18 Monsanto Company Alkylaryl sulfonate compositions
US6083897A (en) * 1998-08-28 2000-07-04 Huntsman Petrochemical Corporation Solubilization of low 2-phenyl alkylbenzene sulfonates
US6133217A (en) * 1998-08-28 2000-10-17 Huntsman Petrochemical Corporation Solubilization of low 2-phenyl alkylbenzene sulfonates
US6617303B1 (en) 1999-01-11 2003-09-09 Huntsman Petrochemical Corporation Surfactant compositions containing alkoxylated amines

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3926862A (en) * 1973-04-16 1975-12-16 Allied Chem Detergent solvent compositions
US5330663A (en) * 1992-09-02 1994-07-19 Chevron Research And Technology Company Neutral and low overbased alkylphenoxy sulfonate additive compositions
US5330664A (en) * 1992-09-02 1994-07-19 Chevron Research And Technology Company Neutral and low overbased alkylphenoxy sulfonate additive compositions derived from alkylphenols prepared by reacting an olefin or an alcohol with phenol in the presence of an acidic alkylation catalyst
US5318710A (en) * 1993-03-12 1994-06-07 Chevron Research And Technology Company Low viscosity Group II metal overbased sulfurized C16 to C22 alkylphenate compositions
US5320762A (en) * 1993-03-12 1994-06-14 Chevron Research And Technology Company Low viscosity Group II metal overbased sulfurized C12 to C22 alkylphenate compositions
US5320763A (en) * 1993-03-12 1994-06-14 Chevron Research And Technology Company Low viscosity group II metal overbased sulfurized C10 to C16 alkylphenate compositions
FR2731427B1 (fr) * 1995-03-08 1997-05-30 Chevron Chem Sa Alkylaryl-sulfonates lineaires isomerises, utiles comme additifs pour huiles lubrifiantes et hydocarbures alkylaryliques correspondants
JP5815750B2 (ja) 2011-02-17 2015-11-17 ザ プロクター アンド ギャンブルカンパニー Ｃ１０〜ｃ１３アルキルフェニルスルホネートの混合物を含む組成物

Citations (3)

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Publication number Priority date Publication date Assignee Title
US2695326A (en) * 1950-06-28 1954-11-23 Standard Oil Dev Co C11 to c13 copolymers of propene and n-butene
US3169987A (en) * 1960-12-30 1965-02-16 Universal Oil Prod Co Alkaryl sulfonate production via n-olefin isomerization
US3248443A (en) * 1963-01-31 1966-04-26 Monsanto Co Process for alkylating aromatic hydrocarbons

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US2220099A (en) * 1934-01-10 1940-11-05 Gen Aniline & Flim Corp Sulphonic acids
US2161173A (en) * 1936-07-02 1939-06-06 Monsanto Chemicals Alkyl-substituted aromatic sulphonic acids
US2161174A (en) * 1936-07-02 1939-06-06 Monsanto Chemicals Alkyl-substituted aromatic sulphonic acids
US2283199A (en) * 1936-07-30 1942-05-19 Allied Chem & Dye Corp Detergent
BE494397A (enrdf_load_stackoverflow) * 1949-03-09
US2723240A (en) * 1950-02-01 1955-11-08 Exxon Research Engineering Co Alkyl aryl sulfonate detergent solutions
US2952639A (en) * 1954-06-30 1960-09-13 Stepan Chemical Co Purification of detergent compositions
GB852079A (en) * 1957-12-24 1960-10-26 British Hydrocarbon Chem Ltd Production of alkyl benzenes
US3349141A (en) * 1964-01-20 1967-10-24 Chevron Res Detergent alkylate composition of secondary phenyl-substituted n-alkanes

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2695326A (en) * 1950-06-28 1954-11-23 Standard Oil Dev Co C11 to c13 copolymers of propene and n-butene
US3169987A (en) * 1960-12-30 1965-02-16 Universal Oil Prod Co Alkaryl sulfonate production via n-olefin isomerization
US3248443A (en) * 1963-01-31 1966-04-26 Monsanto Co Process for alkylating aromatic hydrocarbons

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3487023A (en) * 1964-01-20 1969-12-30 Chevron Res Detergent compositions of sulfonated secondary phenyl-substituted n-alkanes
US3426092A (en) * 1967-11-20 1969-02-04 Universal Oil Prod Co Method for producing detergent-grade alkylate
US4162236A (en) * 1978-01-05 1979-07-24 Monsanto Company Detergent compositions containing mixtures of alkylbenzene sulfonates as the detergent active
US4687593A (en) * 1984-12-17 1987-08-18 Monsanto Company Alkylaryl sulfonate compositions
US6083897A (en) * 1998-08-28 2000-07-04 Huntsman Petrochemical Corporation Solubilization of low 2-phenyl alkylbenzene sulfonates
US6133217A (en) * 1998-08-28 2000-10-17 Huntsman Petrochemical Corporation Solubilization of low 2-phenyl alkylbenzene sulfonates
US6617303B1 (en) 1999-01-11 2003-09-09 Huntsman Petrochemical Corporation Surfactant compositions containing alkoxylated amines

Also Published As

Publication number Publication date
JPS504203B1 (enrdf_load_stackoverflow) 1975-02-17
DE1518622B2 (de) 1974-06-06
DE1518622A1 (de) 1969-04-10
DE1518622C3 (enrdf_load_stackoverflow) 1990-03-29
FR1420865A (fr) 1965-12-10
GB1041491A (en) 1966-09-07
US3487023A (en) 1969-12-30

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