US3358047A - Linear alkylbenzene compositions - Google Patents

Linear alkylbenzene compositions Download PDF

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Publication number
US3358047A
US3358047A US439057A US43905765A US3358047A US 3358047 A US3358047 A US 3358047A US 439057 A US439057 A US 439057A US 43905765 A US43905765 A US 43905765A US 3358047 A US3358047 A US 3358047A
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United States
Prior art keywords
compositions
mixture
weight
phenylalkanes
detergent
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Expired - Lifetime
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US439057A
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English (en)
Inventor
Liston Thomas Raymond
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Allied Corp
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Allied Chemical Corp
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Publication date
Application filed by Allied Chemical Corp filed Critical Allied Chemical Corp
Priority to US439057A priority Critical patent/US3358047A/en
Priority to NL6603138A priority patent/NL6603138A/xx
Priority to CH344266A priority patent/CH482015A/de
Priority to DE19661543989 priority patent/DE1543989A1/de
Priority to BE677664D priority patent/BE677664A/xx
Priority to FR52956A priority patent/FR1470987A/fr
Priority to GB10862/66A priority patent/GB1108623A/en
Application granted granted Critical
Publication of US3358047A publication Critical patent/US3358047A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • 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

  • the alkylbenzenes of the present invention comprise mixtures of phenylalkanes in which the alkyl substituents are essentially linear ,and contain from 8 to 18 carbon atoms, the relative proportion of the 2- phenylalkane content of the lowest molecular weight phenylalkane species present in the mixture being at least 5% higher than that of the Z-phenylalkane content of the next higher molecular species, which in turn is at least 5% higher than that of the Z-phenyl content of the next higher molecular species, and preferably the overall content of 2-phenylalkanes present in the mixture of phenylalkanes being at most about 22% by weight.
  • This invention relates to improved linear alkylbenzene compositions More particularly it relates to linear alkylbenzene compositions which are eminently useful for production of linear alkylaryl sulfonate compositions characterized by excellent detergent properties.
  • linear alkylbenzenes follows closely the methods which have been developed for the preparation of the conventional branched chain alkylbenzenes, i.e., condensation of a selected mixture of alkylchlorides with benzene in the presence of aluminum or aluminum chloride as catalyst, it has been determined that the resultant linear alkylbenzene compositions contain an undesirably high content of the 2-phenylalkane isomers.
  • alkylbenzene sulfonate compositions particularly those in which the alkyl chains are derived from mixtures of hydrocarbons which contain an average of more than twelve carbon atoms, should contain 20% or less of the 2-phenyl isomers in order to possess acceptable detergent properties.
  • Copending US. application S.N. 415,497 filed Dec. 2, 1964 includes a disclosure of a process for preparing linear alkylbenzene compositions having a desirably low content of 2-phenylalkanes by a process which includes the steps of:
  • linear alkylbenzene sulfonate detergent compositions derived from various mixtures of linear alkylbenzenes of low 2-phenylalkane content and wherein the Z-phenylalkane content of each of the molecular species present is approximately the same, vary considerably with respect to their detergent properties.
  • a single molecular species is understood to include one or more phenylalkanes, wherein the alkane moiety is derived from a single alkane hydrocarbon, e.g.
  • the degree of latitude permitted in the selection of the mixture of the molecular species to be converted to alkylbenzene sulfonates of superior detergent properties is greater than when the Z-phenylalkane content of each of the molecular species present is substantially the same.
  • new compostiions of matter com-prising mixtures of phenylalkanes in which the alkyl substituents are essentially linear and contain from 8 to 18 carbon atoms, the relative proportion by weight of the 2phenylalkane content of the lowest molecular weight phenylalkane species present in the mixture being at least 5% higher than that of the Z-phenylalkane content of the next higher molecular species which in turn is at least 5% higher than that of the 2-phenyl content of the next higher molecular species, and preferably the overall content of Z-phenylalkanes present in the mixture of phenylalkanes being at most about 22% by weight.
  • the products of this invention can betprepared in several ways.
  • separate streams of phenylalkanes in each of which the alkyl substituent is derived from a single hydrocarbon, e.g. n-dodecane, and in which the 2-phenylalkane isomer has been adjusted to the desired level, are mixed; then, for conversion to detergent compositions, the resultant mixture of phenyl-alkanes is sulfonated, neutralized, and dried and the alkylbenzene sulfonate mixture produced is mixed with suitable builders and other conventional detergent components.
  • mixtures of n-alkanes e.g., a 20% dodecane- 80% undecane mixture or a 30% tridecane-70% tetradecane mixture
  • mixtures of n-alkanes can be separately processed to low 2- phenylisomer mixtures of phenylalkanes, e.g. in the above manner, and thereafter equal parts of each of these two mixtures blended together.
  • the latitude in formulating the alkylbenzene compositions suitable for conversion to high quality alkylbenzene sulfonate detergents is dependent to a major degree upon the spread (i.e. the relative difference) of the Zsphenylalkane content of the various phenylalkane components present in the mixture.
  • the 2-phenylisomer of the lowest molecular weight isomeric group should be present in a proportion by weight with respect to its isomeric group which is at least about greater than that of the next higher member with respect to its isomeric group, which in turn should be present in a proportion which is at least about 5% higher than the next higher member with respect to its isomeric group.
  • Highly effective mixtures of alkylbenzenes and hence especially preferred are those that contain essentially phenyldodecanes of which about 20 to about 30% by weight is the 2-phenyldodecane, phenyltridecanes of which about to about 20% by weight is Lphenyltridecane, and phenyltetradecanes of which about 5 to about 12% by weight is Z-phenyltetradecane.
  • EXAMPLE 1 Part A.A mixture of phenyldodecanes containing 22% of the 2-phenylisomer and prepared from dodecyl chloride and benzene as described in copending US. application Ser. No. 415,497, filed Dec. 2, 1964, a similarly prepared mixture of phenyl tridecanes containing 2-phenyl tridecane, and a similarly prepared mixture of phenyl tetradecanes containing 8% 2-phenyl tetradecanes were blended in the following sixteen different ratios expressed in weight percent.
  • Blends 1, 3, 5, 10, 11, 13, 14 and 15 produced high quality detergent mixtures.
  • EXAMPLE 2 The procedure of Example 1, Part A, was repeated differing in that each of the alkylbenzenes contained 20% of each of the 2-phenylalkanes. These were blended in sixteen blends having the weight distributions indicated and the blends converted to detergent compositions as indicated.
  • EXAMPLE 3 In a similar fashion, sixteen blends of alkylbenzenes consisting of mixtures of phenyldodecanes, phenyltridecanes and phenyltetradecanes were prepared in which the 2-phenyl isomer content of each of the molecular species was about 15%.
  • benzene sulfonate in the conventional manner and each 1 of these mixtures was converted to a built detergent com- 2 9?
  • This blend of alkylbenzenes, containing about 2- phenylalkanes was converted by sulfonation, neutralization and admixture with conventional builders as indicated in Example 1 above, to a high quality detergent composition.
  • the detergent properties of this composition were evaluated by the dishwashing test described in the above examples. This composition washed 19 plates in soft water and 22 plates in hard water, indicating that this detergent composition possessed excellent detergent properties.
  • a mixture of essentially normal phenylalkanes the n-alkyl substituents of which contain from 8 to 18 carbon atoms, and in which the proportion of the 2-phenyl isomer of each isomeric group present in significant amount is at least about 5% higher than the proportion of the 2-phenyl isomer of the next higher group, each with respect to its own isomeric group, the overall content of Z-phenylalkanes being at most about 22% by weight.
  • a mixture of linear alkylbenzenes consisting essentially of phenyldodecanes, phenyltridecanes and phenyltetradecanes, the phenyldodecanes comprising about 20 to about 30% by weight of Z-phenyldodecane, the phenyltridecanes comprising about 10 to about 20% by weight of Z-phenyltridecane, and the phenyltetradecanes comprising about 5 to about 12% by weight of Z-phenyltetradecane.
  • a mixture of linear alkylbenzenes consisting essentially of phenyldodecanes, phenyltridecanes and phenyltetradecanes, the phenyldodecanes comprising about 22% by weight of 2-phenyldodecane, the phenyltridecanes comprising about 15% by weight of 2-phenyltridecane and the phenyltetradecanes comprising about 8% by weight of Z-phenyltetradecane.
  • a mixture of linear alkylbenzenes consisting essentially of phenyldodecanes, phenyltridecanes, and phenyltetradecanes, the phenyldodecanes comprising about 26% by weight of 2-phenyldodecane, the phenyltridecanes comprising about 16% by weight of 2-phenyltridecane and the phenyltetradecanes comprising about 10% by weight of 2-phenyltetradecane, said mixture containing not over about 22% by weight of 2-phenylakane isomers.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Detergent Compositions (AREA)
US439057A 1965-03-11 1965-03-11 Linear alkylbenzene compositions Expired - Lifetime US3358047A (en)

Priority Applications (7)

Application Number Priority Date Filing Date Title
US439057A US3358047A (en) 1965-03-11 1965-03-11 Linear alkylbenzene compositions
NL6603138A NL6603138A (pl) 1965-03-11 1966-03-09
CH344266A CH482015A (de) 1965-03-11 1966-03-10 Durch Sulfonierung und anschliessende Neutralisation in ein Detergens überführbare Zubereitung
DE19661543989 DE1543989A1 (de) 1965-03-11 1966-03-10 Phenylalkanmassen fuer die Herstellung von Wasch- und Reinigungsmitteln
BE677664D BE677664A (pl) 1965-03-11 1966-03-10
FR52956A FR1470987A (fr) 1965-03-11 1966-03-10 Compositions nouvelles contenant des phényl-n-alcanes et leur procédé de production
GB10862/66A GB1108623A (en) 1965-03-11 1966-03-11 Phenylalkane compositions

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US439057A US3358047A (en) 1965-03-11 1965-03-11 Linear alkylbenzene compositions

Publications (1)

Publication Number Publication Date
US3358047A true US3358047A (en) 1967-12-12

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US439057A Expired - Lifetime US3358047A (en) 1965-03-11 1965-03-11 Linear alkylbenzene compositions

Country Status (7)

Country Link
US (1) US3358047A (pl)
BE (1) BE677664A (pl)
CH (1) CH482015A (pl)
DE (1) DE1543989A1 (pl)
FR (1) FR1470987A (pl)
GB (1) GB1108623A (pl)
NL (1) NL6603138A (pl)

Cited By (2)

* 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
US4162236A (en) * 1978-01-05 1979-07-24 Monsanto Company Detergent compositions containing mixtures of alkylbenzene sulfonates as the detergent active

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3121123A (en) * 1961-03-20 1964-02-11 California Research Corp Preparation of primary normal alkyl benzenes
US3235616A (en) * 1962-01-08 1966-02-15 Chevron Res Recovery of primary normal alkyl benzenes from mixtures containing the same

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3121123A (en) * 1961-03-20 1964-02-11 California Research Corp Preparation of primary normal alkyl benzenes
US3235616A (en) * 1962-01-08 1966-02-15 Chevron Res Recovery of primary normal alkyl benzenes from mixtures containing the same

Cited By (2)

* 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
US4162236A (en) * 1978-01-05 1979-07-24 Monsanto Company Detergent compositions containing mixtures of alkylbenzene sulfonates as the detergent active

Also Published As

Publication number Publication date
BE677664A (pl) 1966-08-01
GB1108623A (en) 1968-04-03
CH482015A (de) 1969-11-30
NL6603138A (pl) 1966-09-12
DE1543989A1 (de) 1970-02-05
FR1470987A (fr) 1967-02-24

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