GB1061473A - Bicyclic sulphur containing olefines - Google Patents

Bicyclic sulphur containing olefines

Info

Publication number
GB1061473A
GB1061473A GB5314/64A GB531464A GB1061473A GB 1061473 A GB1061473 A GB 1061473A GB 5314/64 A GB5314/64 A GB 5314/64A GB 531464 A GB531464 A GB 531464A GB 1061473 A GB1061473 A GB 1061473A
Authority
GB
United Kingdom
Prior art keywords
radical
carbon atom
acyl
removal
sulphur
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
GB5314/64A
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.)
Hooker Chemical Corp
Original Assignee
Hooker Chemical 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
Application filed by Hooker Chemical Corp filed Critical Hooker Chemical Corp
Publication of GB1061473A publication Critical patent/GB1061473A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/08—Bridged systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
    • C07D495/14—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
    • C10M135/32—Heterocyclic sulfur, selenium or tellurium compounds
    • C10M135/34—Heterocyclic sulfur, selenium or tellurium compounds the ring containing sulfur and carbon only
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
    • C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
    • C10M137/04—Phosphate esters
    • C10M137/10—Thio derivatives
    • C10M137/105—Thio derivatives not containing metal
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C10M2219/102—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon only in the ring
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
    • C10M2219/106—Thiadiazoles
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2221/00—Organic macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2221/04—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/042—Metal salts thereof
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/047—Thioderivatives not containing metallic elements
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
    • C10M2223/065—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds containing sulfur
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/02—Groups 1 or 11
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/04—Groups 2 or 12
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/08—Groups 4 or 14
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/14—Group 7
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/20—Metal working
    • C10N2040/22—Metal working with essential removal of material, e.g. cutting, grinding or drilling

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Lubricants (AREA)

Abstract

The invention comprises 9-thiabicyclononenes of the general formula <PICT:1061473/C2/1> wherein the carbon atoms to which the sulphur bridge is attached are separated by at least two carbon atoms, t is 0, 1 or 2, X is one of the following: (1) a halogen atom; (2) a radical of formula RZ where R is a hydrogen atom or a "hydrocarbyl" or "acyl" radical or a pyridyl radical and Z is oxygen or sulphur; (3) a radical of the formula NR1R2(R3)n <FORM:1061473/C2/1> wherein R1 and R2 are each a hydrogen atom or an "acyl" or "hydrocarbyl" radical or may be conjoined or may together with N form a heterocyclic ring, R3 is a hydrogen atom or "hydrocarbyl" radical, n is 0 or 1, n being 0 when either R1 or R2 is acyl, Y is an anion of valence v, and n1 is 0 when N is tertiary and 1 when N is quaternary; (4) a carboxyl radical or a salt, nitrile, amide, ester or acid halide thereof; or (5) a radical of the formula -N=C=Z, wherein Z is oxygen or sulphur, and wherein the X substituent is bonded to the carbon atom 5 when the sulphur bridge extends from carbon atom 1 to carbon atom 6, and the X substituent is bonded to carbon atom 6 when the sulphur bridge extends from carbon atom 1 to carbon atom 5. The term "hydrocarbyl" is defined as being the radical derived from a hydrocarbon or substituted hydrocarbon by removal of one or more hydrogen atoms from one or more carbon atoms and the term "acyl" is defined as the radical derived from an acid by the removal of an OH group or in the case of a dicarboxylic acid optionally by removal of two OH groups each free valence then being attached to a 9-thiabicyclo[4,2,1] or [3,3,1]-nonenyl group and in the case of thiolo acids by removal of an -SH group. The compounds of the invention are prepared by various methods from halo-9-thiabicyclononenes which halo compounds are obtained by heating a dihalo-9-thiabicyclononane at 110 DEG to 220 DEG C. until substantially 1 molar equivalent of hydrogen halide is evolved. This dehydrohalogenation may be catalysed by addition of Lewis acids or extended-surface solids having catalytic properties.ALSO:Biocidal compositions comprise a compound of the general formula <FORM:1061473/A5-A6/1> wherein the carbon atoms to which the sulphur bridge is attached are separated by at least two carbon atoms, t is 0, 1 or 2, X is one of the following: (1) a halogen atom; (2) a radical of formula RZ where R is a hydrogen atom or a "hydrocarbyl" or "acyl" radical or a pyridyl radical and Z is oxygen or sulphur; (3) a radical of the formula NR1R2(R3)n 7(n\sv/v) wherein R1 and R2 are each a hydrogen atom or an "acyl" or "hydrocarbyl" radical or may be conjoined or may together with N form a heterocyclic ring, R3 is a hydrogen atom or a "hyrocarbyl" radical, n is 0 or 1, n being 0 when either R1 or R2 is acyl, 7 is an anion of valence v, and n\sv is 0 when N is tertiary or 1 when N is quaternary; (4) a carboxyl radical or a salt, nitrile, amide, ester or acid halide thereof; or (5) a radical of the formula -N=C=Z, wherein Z is oxygen or sulphur, and wherein the X substituent is bonded to the carbon atom 5 when the sulphur bridge extends from carbon atom 1 to carbon atom 6, and the X substituent is bonded to carbon atom 6 when the sulphur bridge extends from carbon atom 1 to carbon atom 5 together with a diluent or carrier therefor. The term "hydrocarbyl" is defined as being the radical derived from a hydrocarbon or substituted hydrocarbon by removal of one or more hydrogen atoms from one or more carbon atoms and the term "acyl" is defined as the radical derived from an acid by removal of an OH group or in the case of a dicarboxylic acid optionally by removal of two OH groups each free valence then being attached to a 9-thialicyclo [4,2,1] or [3,3,1]-nonenyl group and in the case of thiolo acids by removal of an -SH group. The biocidal compositions may be organic solutions, aqueous dispersions, aqueous emulsions and wettable powders and may contain other pesticides or insecticides or synergists, e.g. piperaryl butoxide. The solid formulations may also contain surface active agents, sticking agents, stabilizing agents or binders.
GB5314/64A 1963-02-25 1964-02-07 Bicyclic sulphur containing olefines Expired GB1061473A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US26124963A 1963-02-25 1963-02-25
US26090963A 1963-02-25 1963-02-25

Publications (1)

Publication Number Publication Date
GB1061473A true GB1061473A (en) 1967-03-15

Family

ID=26948260

Family Applications (2)

Application Number Title Priority Date Filing Date
GB5166/64A Expired GB1061472A (en) 1963-02-25 1964-02-06 Bicyclic sulphur-containing organic compounds, their preparation and use
GB5314/64A Expired GB1061473A (en) 1963-02-25 1964-02-07 Bicyclic sulphur containing olefines

Family Applications Before (1)

Application Number Title Priority Date Filing Date
GB5166/64A Expired GB1061472A (en) 1963-02-25 1964-02-06 Bicyclic sulphur-containing organic compounds, their preparation and use

Country Status (6)

Country Link
BE (1) BE673676A (en)
DE (5) DE1543648B1 (en)
FR (1) FR1412397A (en)
GB (2) GB1061472A (en)
IT (1) IT1193788B (en)
NL (3) NL6401629A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4458061A (en) * 1982-09-29 1984-07-03 The Dow Chemical Company 9-Thiabicyclononanediisocyanates and polymers made therefrom
WO1986000318A1 (en) * 1984-06-29 1986-01-16 The Dow Chemical Company 9-thiabicyclononanediisocyanates and polymers prepared therefrom
WO1986000317A1 (en) * 1984-06-29 1986-01-16 The Dow Chemical Company Alkyl-substituted thiapolycyclic polyahls and polymers prepared therefrom
US4581435A (en) * 1982-12-29 1986-04-08 The Dow Chemical Company Alkyl-substituted thiapolycyclic polyahl and polyurethanes, polyamides and polyureas based thereon

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB9510459D0 (en) 1995-05-24 1995-07-19 Zeneca Ltd Bicyclic amines
IL126882A0 (en) * 1996-05-13 1999-09-22 Zeneca Ltd Bicyclic amines as insecticides
GB9623944D0 (en) * 1996-11-15 1997-01-08 Zeneca Ltd Bicyclic amine derivatives
GB9624114D0 (en) * 1996-11-20 1997-01-08 Zeneca Ltd Pesticidal bicyclic amine derivatives
GB9624611D0 (en) * 1996-11-26 1997-01-15 Zeneca Ltd Bicyclic amine compounds
WO1998025924A1 (en) 1996-11-26 1998-06-18 Zeneca Limited 8-azabicyclo[3.2.1]octane-, 8-azabicyclo[3.2.1]oct-6-ene-, 9-azabicyclo[3.3.1]nonane-, 9-aza-3-oxabicyclo[3.3.1]nonane- and 9-aza-3-thiabicyclo[3.3.1]nonane derivatives, their preparation and their use as insecticides

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4458061A (en) * 1982-09-29 1984-07-03 The Dow Chemical Company 9-Thiabicyclononanediisocyanates and polymers made therefrom
US4581435A (en) * 1982-12-29 1986-04-08 The Dow Chemical Company Alkyl-substituted thiapolycyclic polyahl and polyurethanes, polyamides and polyureas based thereon
WO1986000318A1 (en) * 1984-06-29 1986-01-16 The Dow Chemical Company 9-thiabicyclononanediisocyanates and polymers prepared therefrom
WO1986000317A1 (en) * 1984-06-29 1986-01-16 The Dow Chemical Company Alkyl-substituted thiapolycyclic polyahls and polymers prepared therefrom

Also Published As

Publication number Publication date
FR1412397A (en) 1965-10-01
GB1061472A (en) 1967-03-15
DE1543648B1 (en) 1970-04-02
NL6401629A (en) 1964-10-26
NL129205C (en)
DE1232976B (en) 1967-01-26
DE1229102B (en) 1966-11-24
IT1193788B (en) 1988-08-24
DE1295567B (en) 1969-05-22
BE673676A (en) 1966-04-01
DE1297111B (en) 1969-06-12
NL6401628A (en) 1964-08-26

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