US2157014A - Tertiary amyl ortho-cresol - Google Patents

Tertiary amyl ortho-cresol Download PDF

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Publication number
US2157014A
US2157014A US126200A US12620037A US2157014A US 2157014 A US2157014 A US 2157014A US 126200 A US126200 A US 126200A US 12620037 A US12620037 A US 12620037A US 2157014 A US2157014 A US 2157014A
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Prior art keywords
cresol
ortho
tertiary
amyl
tertiary amyl
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Expired - Lifetime
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US126200A
Inventor
George W Raiziss
Le Roy W Clemence
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Abbott Laboratories
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Abbott Laboratories
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Priority claimed from US731898A external-priority patent/US2073995A/en
Application filed by Abbott Laboratories filed Critical Abbott Laboratories
Priority to US126200A priority Critical patent/US2157014A/en
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
    • C07C39/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring monocyclic with no unsaturation outside the aromatic ring
    • C07C39/06—Alkylated phenols
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
    • C07C37/16—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms by condensation involving hydroxy groups of phenols or alcohols or the ether or mineral ester group derived therefrom

Definitions

  • Our invention relates to a group of compounds which have bactericidal and bacteriostatic value, and may be classed broadly as alkyl cresols and more particularly as tertiary-amyl cresols. They are also of value as intermediates for halogenated alkyl cresols which also have bactericidal and bacteriostatic value and which are described and claimed in certain of our co-pending applications.
  • the alkaline extract is allowed to stand until there is a clear separation of the insoluble oil. This is removed by extraction with petroleum ether until the alkaline layer no longer becomes cloudy on diluting a small sample with water.
  • the alkaline portion is drawn ofi and then acidified with H01.
  • the oil which is liberated is separated, washed with Water and then distilled in Vacuo.
  • the desired fraction is collected at the boiling points set forth below; in the case of tertiary amyl-ortho-cresol, the desired product would be collected at 135-l3'7 C. at 10 mm. pressure.
  • the product has a specific gravity of 0.973.
  • All of the compounds disclosed herein are substantially colorless oils, soluble in organic solvents, completely soluble in dilute alkalis, and insoluble in water.

Description

Patented May 2, 1939 UNITED STATES PATENT OFFICE TERTIARY AMYL ORTHO-CRESOL George W. Raiziss and Le Roy W. Clemence,
Philadelphia, Pa., assignors to Abbott Laboratories, North Chicago, 111., a. corporation of Illinois 1 Claim.
The present application is a division of our application filed June 22, 1934, Serial No. 731,898 for Alkyl cresols.
Our invention relates to a group of compounds which have bactericidal and bacteriostatic value, and may be classed broadly as alkyl cresols and more particularly as tertiary-amyl cresols. They are also of value as intermediates for halogenated alkyl cresols which also have bactericidal and bacteriostatic value and which are described and claimed in certain of our co-pending applications.
It is known that the germicidal value of chemical compounds is generally greatly reduced in the presence of blood serum or whole blood. The compounds which we have discovered and which form the subject matter of this application are of high germicidal value in the presence of blood serum and at the same time are of low toxicity, so that our new compounds can be introduced into the human body in relatively high concentrations without any deleterious effect to the patient.
Our new compounds which are specifically described herein, comprise the substantially pure tertiary-amyl derivatives of ortho, meta, and para cresols. All of these compounds may be made by substantially the same process, which is essentially as follows.
204 grams of zinc chloride is dissolved with heating and mixing in 132 grams of tertiary-amyl alcohol. The temperature is raised to the appropriate reaction temperature set forth below; in the case of tertiary-amyl-ortho-cresol this would be 140 C. 108 grams of the desired cresol, orthocresol in this case, is then added gradually. After the addition is complete the temperature is maintained until the mixture separates into two layers and is then continued for about one hour until a maximum separation occurs. The mixture is then cooled and poured. into two liters of water containing a small amount of H01. The oily layer which separates is then washed with water several times, and is extracted with three portions of 10 percent NaOH (about 300 co. in each portion). The alkaline extract is allowed to stand until there is a clear separation of the insoluble oil. This is removed by extraction with petroleum ether until the alkaline layer no longer becomes cloudy on diluting a small sample with water. The alkaline portion is drawn ofi and then acidified with H01. The oil which is liberated is separated, washed with Water and then distilled in Vacuo. The desired fraction is collected at the boiling points set forth below; in the case of tertiary amyl-ortho-cresol, the desired product would be collected at 135-l3'7 C. at 10 mm. pressure. The product has a specific gravity of 0.973.
The various other products are obtained by the same procedure, substituting the appropriate cresol according to the product desired.
All of the compounds disclosed herein are substantially colorless oils, soluble in organic solvents, completely soluble in dilute alkalis, and insoluble in water.
The physical properties of the compounds which we have prepared are as follows:
Max. No. Compound 13. P. Press. Sp. gr. react. temp.
O. Mm. l Tertiary-amyl-ortho-cresol- 135-137 10 0.973 140 Tertiary-amyl-meta-cresol 137440 11 0.973 140 3.... Tertiary-amyl-para-cresol-. 134-141 10 0.992 135 The above compounds may have the following A germicidal agent having high germicidal value combined with low toxicity in the presence of blood serum consisting of substantially pure tertiary-amyl-ortho-cresol, said agent having a boiling point of about 135-137 C. at 10 mm. pressure and being completely soluble in dilute alkali.
GEORGE W. RAIZISS. LE ROY W. CLEMENCE.
US126200A 1934-06-22 1937-02-17 Tertiary amyl ortho-cresol Expired - Lifetime US2157014A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US126200A US2157014A (en) 1934-06-22 1937-02-17 Tertiary amyl ortho-cresol

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US731898A US2073995A (en) 1934-06-22 1934-06-22 Alkyl cresols
US126200A US2157014A (en) 1934-06-22 1937-02-17 Tertiary amyl ortho-cresol

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US2157014A true US2157014A (en) 1939-05-02

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