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GB996489A - Novel hydroxy thio benzamides - Google Patents

Novel hydroxy thio benzamides

Info

Publication number
GB996489A
GB996489A GB19980/62A GB1998062A GB996489A GB 996489 A GB996489 A GB 996489A GB 19980/62 A GB19980/62 A GB 19980/62A GB 1998062 A GB1998062 A GB 1998062A GB 996489 A GB996489 A GB 996489A
Authority
GB
United Kingdom
Prior art keywords
rubber
groups
oils
aralkyl
alkyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB19980/62A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Ethyl Corp
Original Assignee
Ethyl Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from US114003A external-priority patent/US3251821A/en
Application filed by Ethyl Corp filed Critical Ethyl Corp
Publication of GB996489A publication Critical patent/GB996489A/en
Priority claimed from US525133A external-priority patent/US3413224A/en
Expired legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/194—Radicals derived from thio- or thiono carboxylic acids
    • C—CHEMISTRY; METALLURGY
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    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/35—Heterocyclic compounds having nitrogen in the ring having also oxygen in the ring
    • C—CHEMISTRY; METALLURGY
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    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
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    • C08K5/00—Use of organic ingredients
    • C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
    • C08K5/39—Thiocarbamic acids; Derivatives thereof, e.g. dithiocarbamates
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Abstract

The invention comprises a hydroxythiobenzamide having the general formula <FORM:0996489/C2/1> wherein R1 and R2 are C1-C20 alkyl groups or C7-C20 aralkyl groups, R3 and R4 are each alkyl, cycloalkyl, aralkyl, aryl or alkaryl groups or R3 and R4 are groups which may be bonded together through an oxygen atom to form with the N atom depicted a morpholine ring. They may be obtained (a) by heating sulphur with a compound having the formula <FORM:0996489/C2/2> wherein R1 to R4 are as defined above or by heating with sulphur a compound having the formula <FORM:0996489/C2/3> and an amino compound having the formula <FORM:0996489/C2/4> the radicals R1 to R4 being as defined above. In method (a) the reaction temperature may vary from 100 DEG C. to the reflux temperature of the mixture (but not exceeding 300 DEG C.) and is preferably from 130 DEG to 220 DEG C, and in method (b) the temperature may vary from 50 DEG C. to the reflux temperature of the highest boiling reaction mixture (about 300 DEG C.) and is preferably 80 DEG to 135 DEG C. In both types of reaction it is preferred to use an excess of sulphur and elevated pressures may be used. A solvent may be present, e.g. when the phenol is not liquid at the reaction temperature or when using a lower-boiling amine. Suitable solvents are higher-boiling glycol ethers and alcohols, dioxane and pyridine or in reaction (3) the amine reactant itself may also be used as solvent. The residue formed on concentrating the mother liquor after recovering the desired products by solvent extraction or filtration is a viscous oily material having good antioxidant properties and the invention also includes such oily product per se. Several examples are given and the hydroxythiobenzamide products have good antioxidant properties and for this purpose may be added to liquid hydrocarbon fuels, lubricant oils, functional fluids, greases, soaps, fats and oils (see Division C5) or to natural or synthetic rubber and synthetic polymers (see Division C3). 2,6 - Dialkyl - a - morpholino - p - cresols are obtained by reacting a 2,6-dialkylphenol with morpholine and formaldehyde. 3,5-Dialkyl-4-hydroxybenzaldehydes are prepared by the dibromination of the p-methyl group of the corresponding 2,6-dialkyl-p-cresol in the presence of alcohol and then hydrolysing the dibrominated compound.ALSO:Hydroxythiobenzamides having the general formula <FORM:0996489/C3/1> wherein R1 and R2 are C1-C20 alkyl groups or C7-C20 aralkyl groups, R3 and R4 are alkyl, cycloalkyl, aralkyl, aryl, or alkaryl groups or are groups bonded together through an oxygen atom to form with the N atom depicted a morpholine ring (see Division C2) are used as antioxidants for synthetic polymers or rubbers such as polyethylene, polypropylene, polyisobutylene, polybutadiene, methyl rubber, polybutene rubber, natural rubber, butyl rubber, GR-S rubber, GR-N rubber, piperylene rubber and dimethyl butadiene rubber. A specified rubber composition comprises pale crepe rubber and 3,5-di-tert-butyl-4-hydroxy-N,N-di-methyl thiobenzamide.ALSO:Hydroxythiobenzamides having the general formula <FORM:0996489/C4-C5/1> wherein R1 and R2 are C1-C20 alkyl groups or C7-C20 aralkyl groups, R3 and R4 are alkyl, cycloalkyl, aralkyl, aryl or alkaryl groups or R3 and R4 are groups bonded together through an oxygen atom to form with the N atom depicted a morpholine ring (see Division C2) are used as antioxidants in liquid hydrocarbon fuels, lubricating oils, functional fluids, greases, soaps, fats and oils of animal or vegetable origin and in petroleum wax, e.g. paraffin wax and microcrystalline wax. The liquid hydrocarbon fuel may be gasoline, kerosine or fuel oil and the gasoline may contain an organo lead antiknock agent such as tetraethyl lead and in addition may contain a cyclopentadienyl manganese tricarbonyl or cyclopentadienyl nickel nitrosyl and, if desired, other additives such as halogen scavengers, e.g. ethylene dibromide and/or ethylene dichloride, phosphorus, arsenic and antimony compounds, dyes and solvents or diluents. The lubricating oil may be a mineral oil or synthetic diester, e.g. sebacate or adipate and suitable functional fluids are paraffin base distillates, e.g. a Pennsylvania mineral oil (99 S.U.S. at 100 DEG F.) which may also contain as additives: a polyacrylate of molecular weight about 7000 derived from cetyl or lauryl alcohol, a dimethyl silicone polymer anti-foam agent, a zinc dialkyl dithiophosphate and a barium petroleum sulphonate. Specified fats and oils which may be treated to improve their oxidative stability are linseed, cod liver, castor, soy bean, rape seed, coconut, olive, palm, corn, sesame, peanut and babassu oils, butter fat, lard, and beef tallow.
GB19980/62A 1961-06-01 1962-05-24 Novel hydroxy thio benzamides Expired GB996489A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US11400861A 1961-06-01 1961-06-01
US114003A US3251821A (en) 1961-06-01 1961-06-01 Residual oil obtained from reacting 3, 5-hydrocarbon-4-hydroxy-1-tertiaryamino methyl benzenes and sulfur
US525133A US3413224A (en) 1961-06-01 1966-02-04 Antioxidants

Publications (1)

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GB996489A true GB996489A (en) 1965-06-30

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GB19980/62A Expired GB996489A (en) 1961-06-01 1962-05-24 Novel hydroxy thio benzamides

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Country Link
GB (1) GB996489A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006079627A1 (en) * 2005-01-28 2006-08-03 Basf Aktiengesellschaft Method for applying corrosion protection layers comprising thioamides to metallic surfaces
WO2006079643A1 (en) * 2005-01-28 2006-08-03 Basf Aktiengesellschaft Anti-corrosion coatings containing thioamide groups
CN101111571B (en) * 2005-01-28 2011-07-06 巴斯福股份公司 Anti-corrosion coatings containing thioamide groups

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006079627A1 (en) * 2005-01-28 2006-08-03 Basf Aktiengesellschaft Method for applying corrosion protection layers comprising thioamides to metallic surfaces
WO2006079643A1 (en) * 2005-01-28 2006-08-03 Basf Aktiengesellschaft Anti-corrosion coatings containing thioamide groups
CN101111571B (en) * 2005-01-28 2011-07-06 巴斯福股份公司 Anti-corrosion coatings containing thioamide groups
US7981954B2 (en) 2005-01-28 2011-07-19 Basf Aktiengesellschaft Anti-corrosion coatings containing thioamide groups
US8273412B2 (en) 2005-01-28 2012-09-25 Basf Aktiengesellschaft Method for applying corrosion protection layers comprising thioamides to metallic surfaces

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