US3198826A - Alkyl mercaptomethylphosphonic acids - Google Patents

Alkyl mercaptomethylphosphonic acids Download PDF

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Publication number
US3198826A
US3198826A US305809A US30580963A US3198826A US 3198826 A US3198826 A US 3198826A US 305809 A US305809 A US 305809A US 30580963 A US30580963 A US 30580963A US 3198826 A US3198826 A US 3198826A
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United States
Prior art keywords
acid
alkyl
additive
mineral oil
oil
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 - Lifetime
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US305809A
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English (en)
Inventor
George M Calhoun
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.)
Shell USA Inc
Original Assignee
Shell Oil Co
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 to NL109943D priority Critical patent/NL109943C/xx
Priority to BE626579D priority patent/BE626579A/xx
Priority to NL287245D priority patent/NL287245A/xx
Priority to NL272803D priority patent/NL272803A/xx
Priority to NL272804D priority patent/NL272804A/xx
Priority to NL250415D priority patent/NL250415A/xx
Priority to BE611851D priority patent/BE611851A/xx
Priority claimed from US805686A external-priority patent/US3112271A/en
Priority to DES68011A priority patent/DE1151085B/de
Priority to FR824022A priority patent/FR1253771A/fr
Priority to GB12814/60A priority patent/GB904968A/en
Priority claimed from US77817A external-priority patent/US3238131A/en
Priority claimed from US77830A external-priority patent/US3112269A/en
Priority to FR882715A priority patent/FR81706E/fr
Priority to FR882716A priority patent/FR81903E/fr
Priority to GB45909/61A priority patent/GB1010536A/en
Priority to GB45905/61A priority patent/GB955357A/en
Priority claimed from US162924A external-priority patent/US3226322A/en
Priority claimed from US183036A external-priority patent/US3232882A/en
Priority to FR919847A priority patent/FR83758E/fr
Priority to GB48702/62A priority patent/GB957772A/en
Priority to US305809A priority patent/US3198826A/en
Application filed by Shell Oil Co filed Critical Shell Oil Co
Priority to US312329A priority patent/US3316332A/en
Priority to US472663A priority patent/US3309428A/en
Publication of US3198826A publication Critical patent/US3198826A/en
Application granted granted Critical
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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    • C10M141/10—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential at least one of them being an organic phosphorus-containing compound
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
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    • C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
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    • C10N2050/10—Semi-solids; greasy

Definitions

  • This invention relates to a new and novel class of organic Z-thia-methyl phosphono compounds. More particularly the invention is directed to esters of 2-thiamethyl phosphonic acid and their use as additives in various organic compositions such as oils, plastics, etc.
  • the invention is directed to 2-thia-alkyl phosphoruscontaining compounds having the general formula:
  • R is a hydrocarbyl radical having at least 6 carbon atoms such as a saturated C1048 alkyl radical, or an arakyl or aryl radicals; the R s are the same or different C alkyl radicals or hydrogen, or amine, preferably an alkyl amine.
  • Preferred compounds of the general Formula I have the following formula:
  • alkyl portion of the molecule be C1048 alkyl and wherein R is hydrogen or a short alkyl radical of 1-4 carbon atoms,
  • A is an aliphatic amine, preferably a primary or secondary amine, such as C primary straight chain amines, e.g., octylamine, laurylamine, stearylamine, etc., or branched chain primary aliphatic amines, e.g., t-C alkylamine, such as t-c H17NH2, t-C H NH to ttCfiHgjNHg 0r C5 13 secondary aiiphatic amines, such as diamylamine, di-Z-ethylhexylamine, didecylamine, etc.
  • the Z-thiaalkylphosphonic compounds are prepared by reacting a mercaptan or mercaptide having at least 6 carbon atoms with a halomethylphosphono compound such as chloromethylphosphonic acid or chloromethylphosphonate or their thioderivatives in a suitable solvent, such as an aqueous alcoholic solution, at reflux temperature and under inert conditions until the reaction is completed which normally requires from 1 to about 5 days.
  • a suitable solvent such as an aqueous alcoholic solution
  • the mercaptans include aliphatic mercaptans, such as hexyl, octyl, decyl, dodecyl, octadecyl mercaptans, cycloalkyl mercaptans, such as cyclohexyl mercaptan, dicyclohexyl mercaptan, aralkyl mercaptan;
  • the mercaptides can be used such as the alkali metal (Na or K) mercaptides of the above compounds.
  • Suitable halomethylphosphonic compounds include chloromethylphosphonic acid, mono or dihydrocarbyl chloromethylphosphonates, e.g., mono or dibutylv chloromethylphosphonate, mono or di-Z-ethylhexyl chloromethylphosphonate, mono or dilauryl chloromethylphosphonate, mono or diphenyl chloromethylphosphonate, mono or dicyclohexyl chloromethylphosphonate, mono or dibenzyl chloromethylphosphonate, dibutyl dithiochloromethylphosphonate, diphenyl chloromethyl dithiophosphonate, dibutyl chloromethyltrithiophosphonate, alkali metal salts such as Na and K salts of chloromethylphosphonic acid, Na and K salts of monobutyl chloromethylphosphonic acid, Na and K salts of monodecyl chloromethylphosphonic acid and the like.
  • a suitable mercapto compound such as an alkali metal (Na or K) C1048 alkyl mercaptide with an alkali metal (Na or K) saltof chloromethylphosphonic acid in an alcoholic solution under reflux conditions and under an inert atmosphere to form the alkali metal salt of an alkylmercaptomethylphosphonic acid.
  • the salt is then treated with a strong acid such as hydrochloric acid to spring the free alkylmercaptomethylphosphonic acid, which can be converted into desired partial or full esters of polyvalent metal salts or amine salts for use as oil, fuel and grease additives as well as other uses.
  • Example I The procedure of Example I was followed except that potassium salt of phenylmercaptanwas used instead of potassium salt of decylmercaptan and the final product was phenylmercaptomethylphosphonic acid.
  • the additives of this invention are novel compounds. They are oil-soluble and can be used in amounts of from about 0.1% to about 25%, preferably from about 0.5%
  • Mercaptomethylphosphono compounds of this invention are outstanding additives for various liquid hydrocarbon products, such as natural and synthetic hydrocarbon lubricating oils, greases, fuels (gasoline, kerosene, gas oil, burner fuel oil), asphalts, waxes, slushing oil, industrial oils, e.g., metal working and drawing oils, quenching oils, textile oils, hydraulic oils, dielectric compositions and other industrial oils. They are particularly outstanding when added in small amounts to lubricating oils and lubricating compositions to impart extreme pressure and anti-wear properties to such materials. Also, these additives are useful additives for gasoline, fuel oils, and other light oil products.
  • compositions are illustrative of the invention, the percentages being by weight, of the indicated additive or additives with the remainder being essentially the base.
  • Composition A Percent Example I additive 2 1010 mineral oil Balance Composition B:
  • Example II additive 1 SAE 30 mineral oil Balance Composition F:
  • Example I additive 5 'Ucon 50HB660 polyethylene propylene glycol having a SUS viscosity at 100 F.
  • Example I additive 0.1 Fuel oil (No. 2) Balance Compositions of this invention were evaluated for their extreme pressure properties on a Spur-Gear machine.
  • the machine consists essentially of two geometrically similar pairs of gears connected by two parallel shafts.
  • the gear pairs are placed in separate gear boxes, which also contain the supporting ball bearings.
  • One of the shafts consists of two sections connected by a coupling. Loading is accomplished by locking one side of the coupling and applying torque to the other.
  • the conditions of the test were:
  • Table I Composition Score load, lbs/in. A through I 5,600 1010 mineral oil+2% C alkenyl succinic acid 1,400 1010 mineral oil +2% malonic acid 2,800 1010 mineral oil+2% 3-hexadecyl adipic acid 1,400 1010 mineral oil+2% dodecylmercapto succinic acid 1,400 1010 mineral oil+10% glycerol monooleate 1,800 1010 mineral oil+2% C13H27OH (Oxo process) 1010 mineral oil
  • the following compositions were also tested for stability in the Dornt Oxidation Test described in the Natural Petroleum News, September 17, 1941, pages 294-6 under the following conditions: 302 F., iron catalyst, mineral white oil base and additive amount in each example was about 1% by weight and the results are shown in Table II.
  • the mercaptomethylphosphono compounds of this invention are useful also for providing superior load-carrying properties for lubricating oils which contain minor amounts of other agents, such as silicone anti-foaming agents, alkylphenol anti-oxidants, polyacrylate ester viscosity-index improvers, long chain fatty acids such as lauric and oleic acids, oiliness agents and the like.
  • other agents such as silicone anti-foaming agents, alkylphenol anti-oxidants, polyacrylate ester viscosity-index improvers, long chain fatty acids such as lauric and oleic acids, oiliness agents and the like.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Dentistry (AREA)
  • Plant Pathology (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Lubricants (AREA)
  • Liquid Carbonaceous Fuels (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
US305809A 1959-04-13 1963-08-30 Alkyl mercaptomethylphosphonic acids Expired - Lifetime US3198826A (en)

Priority Applications (19)

Application Number Priority Date Filing Date Title
BE626579D BE626579A (el) 1959-04-13
NL287245D NL287245A (el) 1959-04-13
NL272803D NL272803A (el) 1959-04-13
NL272804D NL272804A (el) 1959-04-13
NL109943D NL109943C (el) 1959-04-13
NL250415D NL250415A (el) 1959-04-13
BE611851D BE611851A (el) 1959-04-13
DES68011A DE1151085B (de) 1959-04-13 1960-04-11 Schmiermittelgemisch
FR824022A FR1253771A (fr) 1959-04-13 1960-04-11 Composés hydrocarbylmercaptométhylphosphono et compositions en contenant
GB12814/60A GB904968A (en) 1959-04-13 1960-04-11 Mercaptomethyl phosphono compounds and compositions containing them
GB45905/61A GB955357A (en) 1959-04-13 1961-12-21 Organophosphorus-substituted dimethyl disulphides, and lubricant and fuel compositions containing the same
FR882716A FR81903E (fr) 1959-04-13 1961-12-21 Composés hydrocarbylmercaptométhyl-phosphono et compositions en contenant
FR882715A FR81706E (fr) 1959-04-13 1961-12-21 Composés hydrocarbylmercaptométhylphosphono et compositions en contenant
GB45909/61A GB1010536A (en) 1959-04-13 1961-12-21 Organic phosphonic compounds useful as fuel and lubricant additives, and compositions containing organic phosphonic compounds
GB48702/62A GB957772A (en) 1959-04-13 1962-12-27 Polythiahydrocarbylphosphono compounds and compositions containing them
FR919847A FR83758E (fr) 1959-04-13 1962-12-27 Composés hydrocarbylmercaptométhyl-phosphono et compositions en contenant
US305809A US3198826A (en) 1959-04-13 1963-08-30 Alkyl mercaptomethylphosphonic acids
US312329A US3316332A (en) 1959-04-13 1963-09-30 Sulfoxy alkyl phosphono compounds
US472663A US3309428A (en) 1959-04-13 1965-07-16 Oil-soluble bis(methylphosphonodisulfides

Applications Claiming Priority (8)

Application Number Priority Date Filing Date Title
US805686A US3112271A (en) 1959-04-13 1959-04-13 Liquid hydrocarbon composition
US77830A US3112269A (en) 1960-12-23 1960-12-23 Lubricating compositions containing sulfoxy alkyl phosphono compounds
US77817A US3238131A (en) 1960-12-23 1960-12-23 Lubricating compositions containing bis(phosphono-methyl) disulfides
US162924A US3226322A (en) 1961-12-28 1961-12-28 Liquid hydrocarbon composition and additives therefor
US183036A US3232882A (en) 1962-03-28 1962-03-28 Lubricating oil compositions
US305809A US3198826A (en) 1959-04-13 1963-08-30 Alkyl mercaptomethylphosphonic acids
US312329A US3316332A (en) 1959-04-13 1963-09-30 Sulfoxy alkyl phosphono compounds
US472663A US3309428A (en) 1959-04-13 1965-07-16 Oil-soluble bis(methylphosphonodisulfides

Publications (1)

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US3198826A true US3198826A (en) 1965-08-03

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US305809A Expired - Lifetime US3198826A (en) 1959-04-13 1963-08-30 Alkyl mercaptomethylphosphonic acids
US312329A Expired - Lifetime US3316332A (en) 1959-04-13 1963-09-30 Sulfoxy alkyl phosphono compounds
US472663A Expired - Lifetime US3309428A (en) 1959-04-13 1965-07-16 Oil-soluble bis(methylphosphonodisulfides

Family Applications After (2)

Application Number Title Priority Date Filing Date
US312329A Expired - Lifetime US3316332A (en) 1959-04-13 1963-09-30 Sulfoxy alkyl phosphono compounds
US472663A Expired - Lifetime US3309428A (en) 1959-04-13 1965-07-16 Oil-soluble bis(methylphosphonodisulfides

Country Status (5)

Country Link
US (3) US3198826A (el)
BE (2) BE611851A (el)
DE (1) DE1151085B (el)
GB (4) GB904968A (el)
NL (5) NL287245A (el)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3957858A (en) * 1970-04-13 1976-05-18 Monsanto Company Substituted ethane diphosphonic acids and salts and esters thereof

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1357745A (en) * 1971-05-05 1974-06-26 Exxon Research Engineering Co Lubricating oil compositions
US4082793A (en) * 1977-02-09 1978-04-04 The United States Of America As Represented By The Secretary Of The Navy Aromatic phosphinic acids containing sulfone linkage
US4317795A (en) * 1979-04-05 1982-03-02 Phillips Petroleum Company Catalytic alkylation of hydrocarbons
FR2631039A1 (el) * 1988-05-06 1989-11-10 Elf France
US5443744A (en) * 1993-12-17 1995-08-22 Exxon Chemical Patent Inc. Non silicone aggresive alkyl phosphates as lubrication oil additives

Citations (3)

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US2535174A (en) * 1949-04-07 1950-12-26 Us Rubber Co Mercaptoethanephosphonates
US2793225A (en) * 1955-08-19 1957-05-21 Union Oil Co Process for preparing phosphonic acid esters
US2963505A (en) * 1954-11-06 1960-12-06 Bayer Ag Sulphoxides-containing esters of the phosphoric and thiophosphoric acids

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US2708204A (en) * 1950-08-11 1955-05-10 Shell Dev Halogen- and phosphorus-containing compounds
DE935547C (de) * 1952-12-09 1955-11-24 Henkel & Cie Gmbh Verfahren zur Herstellung von Kondensationsprodukten mit organisch gebundenem Phosphor
US2857304A (en) * 1954-11-23 1958-10-21 Monsanto Chemicals Dithiodimethylene diphosphonates

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2535174A (en) * 1949-04-07 1950-12-26 Us Rubber Co Mercaptoethanephosphonates
US2963505A (en) * 1954-11-06 1960-12-06 Bayer Ag Sulphoxides-containing esters of the phosphoric and thiophosphoric acids
US2793225A (en) * 1955-08-19 1957-05-21 Union Oil Co Process for preparing phosphonic acid esters

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3957858A (en) * 1970-04-13 1976-05-18 Monsanto Company Substituted ethane diphosphonic acids and salts and esters thereof

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GB957772A (en) 1964-05-13
US3309428A (en) 1967-03-14
NL109943C (el)
DE1151085B (de) 1963-07-04
GB904968A (en) 1962-09-05
NL250415A (el)
NL272804A (el)
NL272803A (el)
NL287245A (el)
GB955357A (en) 1964-04-15
GB1010536A (en) 1965-11-17
BE611851A (el)
BE626579A (el)
US3316332A (en) 1967-04-25

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