CA1082730A - Process for the production of organic sulphides and disulphides - Google Patents
Process for the production of organic sulphides and disulphidesInfo
- Publication number
- CA1082730A CA1082730A CA258,016A CA258016A CA1082730A CA 1082730 A CA1082730 A CA 1082730A CA 258016 A CA258016 A CA 258016A CA 1082730 A CA1082730 A CA 1082730A
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- Canada
- Prior art keywords
- process according
- formula
- mixture
- reaction mixture
- halogen
- Prior art date
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C329/00—Thiocarbonic acids; Halides, esters or anhydrides thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Abstract of the Disclosure Process for producing organic sulphides or disulphides wherein a salt of the formula
Description
~08;~7~0 This invention relates to a ~rocess for the production of organic sulphides and disulphides corresponding to the formula (I) Rl - C - S - C -ll x S S
wherein x is 1 or 2 and R represents a radical corresponding to the formula R2_o- or R ~ , R being an aliphatic or alicyclic hydrocarbon radical N--containing from 1 to 12 carbon atoms whose carbon chain may be interrupted by one or more oxygen atoms and R and R being alkyl groups having 1 to 6 car-bon atoms which process comprises oxidizing a compound of formula (II) Rl - c S9 ~3 .' S
wherein Rl is as defined above and Y is the cation of a monovalent metal, with a halogen or pseudohalogen at a temperature of from -20 to 60 C in a solvent which is a mixture of water and an aliphatic alcohol, the alcohol be-ing from 50 to 80% by weight of the solvent, and then heating the reaction mixture to cause the reaction mixture to separate into an alcoholic phase whieh eontains the required eompound and an aqueous phase.
The oxidation may optionally be carried out in the presence of an inert gas.
Preferred halogens are ehlorine and bromine; preferred pseudohalo-gens are cyanogen chloride and cyanogen bromide.
The oxidation of eompounds corresponding to formula (II) into compounds of formula (I) is basically known. Oxidation reactions of this kind are accompanied by the formation of large quantities of inorganic salts in aqueous solution.
-~ ~"
~ ~ -- 1 --.
10~3~7~o It i8 known from Cnnadian Patent Speci~lcation No.
856,834 thnt isopropyl xanthogenate can be oxidised with sodium hypochlorite in a mixture o~ i~opropanol and water.
Although particularly pure x~nthogen disulphide is said to be formed, large quantitles o~ water have to be used in order to di~solve the sodium hypochlorite, 80 that large quantitie~ Or dilute aqueouR mlneral salt solutions are formcd.
The process according to the invention a~iord~ the advantage over this prior art th~t only small quantities oi water are required. A mixture Or water and aliphatic al~ohol is u~ed ~or carrying out the proce~s. Monohydric or poly-hydric aliphatic alcohols with 2 to 6 carbon atoms are particularly suitable, monohydric alcohol~, especially propanols and butanols~ bein~ particularly preferred.
.. ~
Particularly suitable radicals R2 in formula (I) are alkyl radic~ls with 3 to 12 carbon atoms, cycloalkyl radicals with 5 to 7 carbon atoms and straight-chain, branched-chain and cycloalkyl ether radicals. Examples are isopropyl, n-butyl, hexyl, octyl.
Particularly suitable radicals R3 are methyl, ethyl, i-propyl and n-butyl.
l Cations of monovalent metals are in particular the cat-- ions of sodium and potassium.
Particularly 3uitable starting materials are dlalkyl dithiocarbamates having 1 to 4 carbon atom~ in the alkyl group with sodium as the cation, also aliphatic ~odium xanthog~nates.
Examples o~ suitable starting materials are sodium diethyl i dithio carbamate, 1,~-dioxa-5-ethyl-5-methylene xanthogenate, sodium dimethyl dithio carbamate.
Le A 16 6~2 - 2 -'' -' ~ ' ~ ~ ' . ' . ' ... ' 108~7~0 To carry out the proce~s, the tarting compounds are dis~olved in water/alcohol mixtures, followed by the intro-duction into the resulting solution with vigorous stirring Of halogen or a p~eudohalogen optionally togather with air. The temperatures applied are generally in the range from about -20 to +60C and pre~erably in the range from O to 30C.
The ratio by weight o~ water to alcohol in the mixture generally amounts to between 5 : 95 and 95 : 5 and preferably to between 20:80 and 50:50.
; Halogen or pseudohalogen may be used with advantage insubstantially stoichiometric quantities or even in a deficit or exce~s. It is particularly preferred to use chlorine gus and cyanogen chloride. Inert gas, for example air or nitrogen, may be added to the halogen in a ratio by volume of halogen to inert gas Or I :lOO.
On completion of the reaction (reilected in many cases in a rall in the pH-value), the reaction mixture may be heated to temperatur~ of up to 80~C. As a result the reaction mixture generally separates into two liquid phase~, which the alcoholic phase contains the organic sulphide or disulphide iormed and the aqueous phase contains the mineral salt iormed. The pha~es may readily be separated one rrOm the other.
The quantity Or water in the reaction mi~ture may be selected in such a way that all the mineral salt dissolves, in which ca~e a highly concentrated salt solution~ which may readily be worked up, is obtained. It is also poesible to use a ~maller quantity oi water, in which case some oi the salt is obtained in solid rorm. The alcohol may also Le A 16 632 - 3 -.
10~7~) be used in a quantity sufficient to dissolve the organic sulphide or d~eulphide, in which case a solution 18 obtained which may readily be worked up by distillation after the material has crystallised out. ~lternatively, the alcohol may bc u~ed in a smaller quantity, in which case a suspension of the organic sulphide or disulphide in a concentrated alcoholic solution o~ this substAnce i9 obtained. In all cases, the reaction mixture can be worked up without difficulty. Eifluents containing inorganic snlts are prevented from being formed in large quantities by volume.
., ,. :
. 1 ' .
, , .
: ~, .
':, ~ Le A 16 632 - 4 -:.
101~'~73(~
EX~MPLE 1 Production of tetraethyl thiuram disulphide A suspension Or ~odium diethyl dithiocarba~nte wa~
prepared by kno~nn methods from 275 g o~ water~ 40 g oi NaOH, 76 g of carbon disulphide and 73 g oi diethylamine.
Following the addition of 308 g of isopropanol, the suspension chnnges lnto a homogeneou~ solution. A mixture of chlorine and air in a ratio o~ approximately 1:50 was then introduced with vigorous stirring at room temperature through a gassing stirrer or through a gassing pipe~ After a while the reaction products, sodium cAloride and tetraethyl thluram di3ulphide, began to precipita~e. A~ter the pII-value oi the reaction mixture had fallen from its original level o~ approximately 14.0 to approximately pH 7.0, the introduction of chlorine was stopped and the reaction mixture was heated to approximately 80C. As a result all the solid reaction products were dis~olved, followed by phase separation into an aqueous phase (311.1 g) and an organic phase (458.1 g).
The aqueous phase wa~ concentrated by evaporation in a rotary evaporator, leaving a solid residue o~ 67.3 g (mostly NaCl).
The organic phase was cooled to 0C and the tetraethyl thiuram disulphide precipltated ln the iorm of ilne crystals wa8 eeparated Ori. Yleld 121.3 g (82~ Or the theoretical yield)~ mp 71C. The mother llquor was concentrated by evaporation~ leaving a resldue oi 14.2 g.
Tetraethyl thiuram disulphide The procedure was a~ described in E~ample 1, except that the quantity Or water used was reduced irom 275 g to 215 g Le A 16 632 - 5 -and the quantity Or isopropanol from 308 g to 300 g. The cffect of thie was that not all the dithiocarbamate was dissolved at the beginnlng of oxidation. ~owever, this (loes not have any adverse effect upon the oxidation proce~s.
~queous phase: 252 g, of which 64.9 g are made up by salt-like residue. Organic phaee: 435.2 g. Yield: 124.4 g (85% of the theoretical yield), mp 71C. Residue following evaporation of the mother liquor: 12.5 g.
~XA~IPL~ 3 nis-(1,3-dioxa-5-ethyl-5-hydroxy methyl cyclohexane xanthogen~-disulphide.
The xanthogenate was produced in known manner from 146 g of 1,3-dioxa-5-ethyl-5-hydroxymethyl-cyclohexane ~': ~ O--C~I2 H2C~ C--CH2--; 40 g of sodium hydroxide, 76 g of CS2 and 52 g of water.
Isopropanol (425 g) and water (75 g) were then added to the viscou8 aqueous xanthogenate solution, the mixture was cooled to approximately 0C and a mixture of chlorine gas and air in a ratlo Or 1: 50 was introduced with vigorous - stirring through a gaseing pipe or through a gassing stirrer.
After the chlorine gas/air mixture had been introduced ior about 4 to 6 hours, the end Or the reaction was rerlected in a sudden f811 of the p~ to below 7. The react~on mixture was then heated to 50C, as a result of which all the xanthogen disulphlde and part of the salt were diesolved.
After the ealt (approximately 35 g) had been filtered Ori~
the aqueou~ phase (74.8 g) was eeparated o~f. The product was recryetallised from the organic phaee (679.3 g) at 0C.
Le A 16 632 - 6 -108~73(~
, Yield: 164.7 ~ (75~ of the theoretical yield), ~MPLE 4 Bis-(1,3-~ioxa-5-ethyl-5-hydroxymethyl cyclohexane xanthogen)-disulphide The procedure w~s a~ described in Example 3, e~cept that the xantho~enate solution wa~ diluted with 350 g a~ oppo~ed to 425 g oi isopropanol and with 150 ~ instead of 75 g of water.
Aqueous ~hase: 228.5 g, 57.8 g of salt contained therein.
Or~anic phase: 555.1 g, contained therein: yield 178.7 g (81% of the theoretical yield).
Bis-dimethyl thiocarbamoyl sulphide (tetramethyl thiuram monosulphide) 68 g of cyanogen chloride were added dropwise with vigorous stirring at 25C to 715 g of aqueous sodium dimethyl dithiocarbamatc solution (42~) and 250 g of n-butanol. On `:
completion of the reaction, the pH-value was 8.0 The suspension formed was then heated to 80C, as a result of which the sulphide di~solved and phase separation occurred. The aqueous phase was separated ofi and the product crystallised out from the organic phase at room temperature. Yield:
207.2 g (95% of the theoretical yield).
Bis-dimethyl thiocarbamoyl Yulphide (tetramethyl , .. . .
~- 25 thiuram monosulphide) 300 g oi n-butanol were added to 357 g of an aqueous sodium dimethyl dithiocarbamate solution (40%). A mlxture of chlorine and air (1:50) was introduced with vigorous ~, stirring at room temperature through a ga8sing stirrer.
The end of o~idation wa~ reilected in the sudden iall oi -:~
Le A 16 632 _ 7 _ .~
, .-.. ..
~08;~7~3() the pH-value to below 7Ø Following pH ad~ustment to 8.0 with 50% sodium hydroxlde, 24.5 g Or sodium cyanide were added and the suspension wa~ hea~ed to 80C, resulting in the formatlon of a homogeneous organlc phase containing the sulphide, and an aqueous suspension becQuse not all the salt was di~solved. The organic phase was separated ofr and the product crystallised out at room temperature. Yield:
81.2 g (78% of the theoretical yield).
' .
Le A 16 632 - 8 -
wherein x is 1 or 2 and R represents a radical corresponding to the formula R2_o- or R ~ , R being an aliphatic or alicyclic hydrocarbon radical N--containing from 1 to 12 carbon atoms whose carbon chain may be interrupted by one or more oxygen atoms and R and R being alkyl groups having 1 to 6 car-bon atoms which process comprises oxidizing a compound of formula (II) Rl - c S9 ~3 .' S
wherein Rl is as defined above and Y is the cation of a monovalent metal, with a halogen or pseudohalogen at a temperature of from -20 to 60 C in a solvent which is a mixture of water and an aliphatic alcohol, the alcohol be-ing from 50 to 80% by weight of the solvent, and then heating the reaction mixture to cause the reaction mixture to separate into an alcoholic phase whieh eontains the required eompound and an aqueous phase.
The oxidation may optionally be carried out in the presence of an inert gas.
Preferred halogens are ehlorine and bromine; preferred pseudohalo-gens are cyanogen chloride and cyanogen bromide.
The oxidation of eompounds corresponding to formula (II) into compounds of formula (I) is basically known. Oxidation reactions of this kind are accompanied by the formation of large quantities of inorganic salts in aqueous solution.
-~ ~"
~ ~ -- 1 --.
10~3~7~o It i8 known from Cnnadian Patent Speci~lcation No.
856,834 thnt isopropyl xanthogenate can be oxidised with sodium hypochlorite in a mixture o~ i~opropanol and water.
Although particularly pure x~nthogen disulphide is said to be formed, large quantitles o~ water have to be used in order to di~solve the sodium hypochlorite, 80 that large quantitie~ Or dilute aqueouR mlneral salt solutions are formcd.
The process according to the invention a~iord~ the advantage over this prior art th~t only small quantities oi water are required. A mixture Or water and aliphatic al~ohol is u~ed ~or carrying out the proce~s. Monohydric or poly-hydric aliphatic alcohols with 2 to 6 carbon atoms are particularly suitable, monohydric alcohol~, especially propanols and butanols~ bein~ particularly preferred.
.. ~
Particularly suitable radicals R2 in formula (I) are alkyl radic~ls with 3 to 12 carbon atoms, cycloalkyl radicals with 5 to 7 carbon atoms and straight-chain, branched-chain and cycloalkyl ether radicals. Examples are isopropyl, n-butyl, hexyl, octyl.
Particularly suitable radicals R3 are methyl, ethyl, i-propyl and n-butyl.
l Cations of monovalent metals are in particular the cat-- ions of sodium and potassium.
Particularly 3uitable starting materials are dlalkyl dithiocarbamates having 1 to 4 carbon atom~ in the alkyl group with sodium as the cation, also aliphatic ~odium xanthog~nates.
Examples o~ suitable starting materials are sodium diethyl i dithio carbamate, 1,~-dioxa-5-ethyl-5-methylene xanthogenate, sodium dimethyl dithio carbamate.
Le A 16 6~2 - 2 -'' -' ~ ' ~ ~ ' . ' . ' ... ' 108~7~0 To carry out the proce~s, the tarting compounds are dis~olved in water/alcohol mixtures, followed by the intro-duction into the resulting solution with vigorous stirring Of halogen or a p~eudohalogen optionally togather with air. The temperatures applied are generally in the range from about -20 to +60C and pre~erably in the range from O to 30C.
The ratio by weight o~ water to alcohol in the mixture generally amounts to between 5 : 95 and 95 : 5 and preferably to between 20:80 and 50:50.
; Halogen or pseudohalogen may be used with advantage insubstantially stoichiometric quantities or even in a deficit or exce~s. It is particularly preferred to use chlorine gus and cyanogen chloride. Inert gas, for example air or nitrogen, may be added to the halogen in a ratio by volume of halogen to inert gas Or I :lOO.
On completion of the reaction (reilected in many cases in a rall in the pH-value), the reaction mixture may be heated to temperatur~ of up to 80~C. As a result the reaction mixture generally separates into two liquid phase~, which the alcoholic phase contains the organic sulphide or disulphide iormed and the aqueous phase contains the mineral salt iormed. The pha~es may readily be separated one rrOm the other.
The quantity Or water in the reaction mi~ture may be selected in such a way that all the mineral salt dissolves, in which ca~e a highly concentrated salt solution~ which may readily be worked up, is obtained. It is also poesible to use a ~maller quantity oi water, in which case some oi the salt is obtained in solid rorm. The alcohol may also Le A 16 632 - 3 -.
10~7~) be used in a quantity sufficient to dissolve the organic sulphide or d~eulphide, in which case a solution 18 obtained which may readily be worked up by distillation after the material has crystallised out. ~lternatively, the alcohol may bc u~ed in a smaller quantity, in which case a suspension of the organic sulphide or disulphide in a concentrated alcoholic solution o~ this substAnce i9 obtained. In all cases, the reaction mixture can be worked up without difficulty. Eifluents containing inorganic snlts are prevented from being formed in large quantities by volume.
., ,. :
. 1 ' .
, , .
: ~, .
':, ~ Le A 16 632 - 4 -:.
101~'~73(~
EX~MPLE 1 Production of tetraethyl thiuram disulphide A suspension Or ~odium diethyl dithiocarba~nte wa~
prepared by kno~nn methods from 275 g o~ water~ 40 g oi NaOH, 76 g of carbon disulphide and 73 g oi diethylamine.
Following the addition of 308 g of isopropanol, the suspension chnnges lnto a homogeneou~ solution. A mixture of chlorine and air in a ratio o~ approximately 1:50 was then introduced with vigorous stirring at room temperature through a gassing stirrer or through a gassing pipe~ After a while the reaction products, sodium cAloride and tetraethyl thluram di3ulphide, began to precipita~e. A~ter the pII-value oi the reaction mixture had fallen from its original level o~ approximately 14.0 to approximately pH 7.0, the introduction of chlorine was stopped and the reaction mixture was heated to approximately 80C. As a result all the solid reaction products were dis~olved, followed by phase separation into an aqueous phase (311.1 g) and an organic phase (458.1 g).
The aqueous phase wa~ concentrated by evaporation in a rotary evaporator, leaving a solid residue o~ 67.3 g (mostly NaCl).
The organic phase was cooled to 0C and the tetraethyl thiuram disulphide precipltated ln the iorm of ilne crystals wa8 eeparated Ori. Yleld 121.3 g (82~ Or the theoretical yield)~ mp 71C. The mother llquor was concentrated by evaporation~ leaving a resldue oi 14.2 g.
Tetraethyl thiuram disulphide The procedure was a~ described in E~ample 1, except that the quantity Or water used was reduced irom 275 g to 215 g Le A 16 632 - 5 -and the quantity Or isopropanol from 308 g to 300 g. The cffect of thie was that not all the dithiocarbamate was dissolved at the beginnlng of oxidation. ~owever, this (loes not have any adverse effect upon the oxidation proce~s.
~queous phase: 252 g, of which 64.9 g are made up by salt-like residue. Organic phaee: 435.2 g. Yield: 124.4 g (85% of the theoretical yield), mp 71C. Residue following evaporation of the mother liquor: 12.5 g.
~XA~IPL~ 3 nis-(1,3-dioxa-5-ethyl-5-hydroxy methyl cyclohexane xanthogen~-disulphide.
The xanthogenate was produced in known manner from 146 g of 1,3-dioxa-5-ethyl-5-hydroxymethyl-cyclohexane ~': ~ O--C~I2 H2C~ C--CH2--; 40 g of sodium hydroxide, 76 g of CS2 and 52 g of water.
Isopropanol (425 g) and water (75 g) were then added to the viscou8 aqueous xanthogenate solution, the mixture was cooled to approximately 0C and a mixture of chlorine gas and air in a ratlo Or 1: 50 was introduced with vigorous - stirring through a gaseing pipe or through a gassing stirrer.
After the chlorine gas/air mixture had been introduced ior about 4 to 6 hours, the end Or the reaction was rerlected in a sudden f811 of the p~ to below 7. The react~on mixture was then heated to 50C, as a result of which all the xanthogen disulphlde and part of the salt were diesolved.
After the ealt (approximately 35 g) had been filtered Ori~
the aqueou~ phase (74.8 g) was eeparated o~f. The product was recryetallised from the organic phaee (679.3 g) at 0C.
Le A 16 632 - 6 -108~73(~
, Yield: 164.7 ~ (75~ of the theoretical yield), ~MPLE 4 Bis-(1,3-~ioxa-5-ethyl-5-hydroxymethyl cyclohexane xanthogen)-disulphide The procedure w~s a~ described in Example 3, e~cept that the xantho~enate solution wa~ diluted with 350 g a~ oppo~ed to 425 g oi isopropanol and with 150 ~ instead of 75 g of water.
Aqueous ~hase: 228.5 g, 57.8 g of salt contained therein.
Or~anic phase: 555.1 g, contained therein: yield 178.7 g (81% of the theoretical yield).
Bis-dimethyl thiocarbamoyl sulphide (tetramethyl thiuram monosulphide) 68 g of cyanogen chloride were added dropwise with vigorous stirring at 25C to 715 g of aqueous sodium dimethyl dithiocarbamatc solution (42~) and 250 g of n-butanol. On `:
completion of the reaction, the pH-value was 8.0 The suspension formed was then heated to 80C, as a result of which the sulphide di~solved and phase separation occurred. The aqueous phase was separated ofi and the product crystallised out from the organic phase at room temperature. Yield:
207.2 g (95% of the theoretical yield).
Bis-dimethyl thiocarbamoyl Yulphide (tetramethyl , .. . .
~- 25 thiuram monosulphide) 300 g oi n-butanol were added to 357 g of an aqueous sodium dimethyl dithiocarbamate solution (40%). A mlxture of chlorine and air (1:50) was introduced with vigorous ~, stirring at room temperature through a ga8sing stirrer.
The end of o~idation wa~ reilected in the sudden iall oi -:~
Le A 16 632 _ 7 _ .~
, .-.. ..
~08;~7~3() the pH-value to below 7Ø Following pH ad~ustment to 8.0 with 50% sodium hydroxlde, 24.5 g Or sodium cyanide were added and the suspension wa~ hea~ed to 80C, resulting in the formatlon of a homogeneous organlc phase containing the sulphide, and an aqueous suspension becQuse not all the salt was di~solved. The organic phase was separated ofr and the product crystallised out at room temperature. Yield:
81.2 g (78% of the theoretical yield).
' .
Le A 16 632 - 8 -
Claims (10)
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEPINED AS FOLLOWS:
1. A process for the preparation of an organic sulphide or disulphide of formula I
I
wherein x is 1 or 2 and R1 represents a radical corresponding to the formula R2-O- or , R2 being an aliphatic or alicyclic hydrocarbon radical containing from 1 to 12 carbon atoms whose carbon chain may be interrupted by one or more oxygen atoms and R3 and R4 being alkyl groups having 1 to 6 car-bon atoms which process comprises oxidizing a compound of formula II
II
wherein R1 is as defined above and Y is the cation of a monovalent metal, with a halogen or pseudohalogen at a temperature of from -20 to 60°C in a solvent which is a mixture of water and an aliphatic alcohol, the alcohol be-ing from 50 to 80% by weight of the solvent, and then heating the reaction mixture to cause the reaction mixture to separate into an alcoholic phase which contains the required compound and an aqueous phase.
I
wherein x is 1 or 2 and R1 represents a radical corresponding to the formula R2-O- or , R2 being an aliphatic or alicyclic hydrocarbon radical containing from 1 to 12 carbon atoms whose carbon chain may be interrupted by one or more oxygen atoms and R3 and R4 being alkyl groups having 1 to 6 car-bon atoms which process comprises oxidizing a compound of formula II
II
wherein R1 is as defined above and Y is the cation of a monovalent metal, with a halogen or pseudohalogen at a temperature of from -20 to 60°C in a solvent which is a mixture of water and an aliphatic alcohol, the alcohol be-ing from 50 to 80% by weight of the solvent, and then heating the reaction mixture to cause the reaction mixture to separate into an alcoholic phase which contains the required compound and an aqueous phase.
2. A process according to claim 1 wherein the oxidation is carried out in the presence of an inert gas.
3. A process according to claim 2 wherein the oxidation is carried out in the presence of air.
4. A process according to claim 1, 2 or 3 wherein the aliphatic alcohol is isopropanol.
5. A process according to claim 1, 2 or 3 wherein Y is sodium.
6. A process according to claim 1, 2 or 3 wherein the halogen is chlorine or bromine.
7. A process according to claim 1, 2 or 3 wherein the pseudohalogen is cyanogen chloride or cyanogen bromide.
8. A process according to claim 1, 2 or 3 wherein R1 is a group wherein R3 and R4 are both ethyl or both methyl groups.
9. A process according to claim 1, 2 or 3 wherein R1 is a group R2-O- in which R2 is a 1,3-dioxa-5-methyl-cyclohex-5-yl-methyl group.
10. A process according to claim 1, 2 or 3 wherein the reaction mixture is heated to about 80°C to separate the mixture into two phases.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2533989A DE2533989C2 (en) | 1975-07-30 | 1975-07-30 | Process for the production of organic sulfides and disulfides |
| DEP2533989.3 | 1975-07-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1082730A true CA1082730A (en) | 1980-07-29 |
Family
ID=5952795
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA258,016A Expired CA1082730A (en) | 1975-07-30 | 1976-07-28 | Process for the production of organic sulphides and disulphides |
Country Status (11)
| Country | Link |
|---|---|
| JP (1) | JPS5217421A (en) |
| BE (1) | BE844582A (en) |
| BR (1) | BR7604937A (en) |
| CA (1) | CA1082730A (en) |
| DE (1) | DE2533989C2 (en) |
| ES (1) | ES450269A1 (en) |
| FR (1) | FR2319629A1 (en) |
| GB (1) | GB1535386A (en) |
| IN (1) | IN142683B (en) |
| IT (1) | IT1062640B (en) |
| NL (1) | NL7608379A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3044811A1 (en) * | 1980-11-28 | 1982-07-01 | Bayer Ag, 5090 Leverkusen | XANTHOGEN DISULFIDES, THE PRODUCTION AND USE THEREOF AS THE MOLDER WEIGHT REGULATOR IN THE POLYMERIZATION OF CHLOROPRENE |
| CN106380436B (en) * | 2016-08-10 | 2018-06-01 | 山东阳谷华泰化工股份有限公司 | A kind of preparation method of dithiodiisopropyl xanthate |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL107253C (en) * | 1960-09-08 | |||
| FR1288391A (en) * | 1961-04-14 | 1962-03-24 | Bayer Ag | Process for manufacturing thiuram monosulfides |
-
1975
- 1975-07-30 DE DE2533989A patent/DE2533989C2/en not_active Expired
-
1976
- 1976-06-22 IN IN1106/CAL/1976A patent/IN142683B/en unknown
- 1976-07-23 GB GB30792/76A patent/GB1535386A/en not_active Expired
- 1976-07-27 JP JP51088758A patent/JPS5217421A/en active Pending
- 1976-07-28 BE BE169294A patent/BE844582A/en not_active IP Right Cessation
- 1976-07-28 NL NL7608379A patent/NL7608379A/en not_active Application Discontinuation
- 1976-07-28 IT IT50632/76A patent/IT1062640B/en active
- 1976-07-28 CA CA258,016A patent/CA1082730A/en not_active Expired
- 1976-07-29 BR BR7604937A patent/BR7604937A/en unknown
- 1976-07-29 ES ES450269A patent/ES450269A1/en not_active Expired
- 1976-07-30 FR FR7623441A patent/FR2319629A1/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| GB1535386A (en) | 1978-12-13 |
| BR7604937A (en) | 1977-08-09 |
| IN142683B (en) | 1977-08-13 |
| ES450269A1 (en) | 1977-09-01 |
| BE844582A (en) | 1977-01-28 |
| IT1062640B (en) | 1984-10-20 |
| DE2533989A1 (en) | 1977-02-24 |
| FR2319629A1 (en) | 1977-02-25 |
| FR2319629B1 (en) | 1980-07-25 |
| JPS5217421A (en) | 1977-02-09 |
| DE2533989C2 (en) | 1984-05-17 |
| NL7608379A (en) | 1977-02-01 |
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