CN106083679A - A kind of preparation method of dialkoxy xanthate polysulfide - Google Patents
A kind of preparation method of dialkoxy xanthate polysulfide Download PDFInfo
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- CN106083679A CN106083679A CN201610438177.9A CN201610438177A CN106083679A CN 106083679 A CN106083679 A CN 106083679A CN 201610438177 A CN201610438177 A CN 201610438177A CN 106083679 A CN106083679 A CN 106083679A
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- dialkoxy
- xanthate
- polysulfide
- organic solvent
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C329/00—Thiocarbonic acids; Halides, esters or anhydrides thereof
- C07C329/12—Dithiocarbonic acids; Derivatives thereof
- C07C329/14—Esters of dithiocarbonic acids
Abstract
A kind of preparation method of dialkoxy xanthate polysulfide, first synthesize diisopropyl disulfide in organic solvent for sodium formate with fatty alcohol, Carbon bisulfide and powdered sodium hydroxide, drip Disulfur dichloride (sulfur monochloride or sulfur dichloride) the most again, reaction prepares dialkoxy xanthate polysulfide, after having reacted, sucking filtration isolates inorganic salt sodium chloride, sell as by-product after simple process, liquid carries out rotation and steams the prepared product of separation, and the organic solvent distilled can reuse.This preparation method flow process is short, product yield and stay in grade, and production efficiency is high.Inorganic salt sodium chloride recovery process is succinct, and without other inorganic salt impurities, purity is high, is conducive to recycling.
Description
Technical field:
The present invention relates to the preparation method of a kind of new type rubber auxiliary agent, specifically a kind of many sulfurations of dialkoxy xanthate
The preparation method of thing, belongs to technical field of fine.
Background technology:
Dialkoxy xanthate polysulfide is a kind of vulcanizing agent accelerator, is applied to natural rubber and synthetic rubber.
Dialkoxy xanthate polysulphide molecules does not contains nitrogen, noxious substance will not be produced after using, such as: thiourea, different sulfur cyanogen
Acid fat, sulfocyanic ester, N-nitrosamine etc..Dialkoxy xanthate polysulfide is used for the compounding of latex and solid rubber
Agent, it is possible to reduce the consumption of many rubber accelerators, be suitable for other accelerator with the use of, such as: ZBED, TBZTD, MBTS
Deng；Dialkoxy xanthate polysulfide can also be used for ore dressing, is a kind of excellent dressing agent.
Existing dialkoxy xanthate polysulfide synthesis technique divides 3 stages to complete.First stage: first with fat
It is yellow that alcohol, organic solvent, Carbon bisulfide and sodium hydroxide (dry method or solvent method) under certain conditions reaction obtains dialkoxy
Ortho acid sodium；Second stage: by oxidized for dialkoxy sodium xanthogenate dose of (sodium hypochlorite, hydrogen peroxide, sym-closene, dichloro
Isocyanuric acid, sodium peroxydisulfate, potassium permanganate, sodium permanganate or potassium peroxydisulfate etc.) oxidation generation curing dialkoxy xanthan
Acid esters；Phase III: curing dialkoxy xanthate and sulfur are reacted in solvent or water, generate dialkoxy
Xanthate polysulfide.
This synthesis technique long flow path and complexity are loaded down with trivial details, and yield and quality are unstable, and the inorganic salt produced is sodium sulfate
With the mixture of sodium chloride, bring to recovery inorganic salt re-using unfavorable.
Summary of the invention:
For the deficiencies in the prior art, the present invention provides the preparation method of a kind of dialkoxy xanthate polysulfide,
This preparation method flow process is short, product yield and stay in grade, and inorganic salt sodium chloride reclaims simple synthesis technique；Concise in technology
Environmental protection, is suitable for industrialized production.
Summary of the invention:
The preparation method of the present invention, first synthesizes two in organic solvent with fatty alcohol, Carbon bisulfide and powdered sodium hydroxide
Isopropyl dithiocarbonic acid sodium, drips Disulfur dichloride (sulfur monochloride or sulfur dichloride) the most again, and reaction prepares dialkoxy xanthan
Acid esters polysulfide, after having reacted, sucking filtration isolates inorganic salt sodium chloride, sells as by-product, liquid after simple process
Body portion carries out rotation and steams the available product of separation, and the organic solvent distilled can reuse.
Detailed Description Of The Invention:
A kind of dialkoxy xanthate polysulfide, structural formula is as follows:
Wherein, alkoxyl (CXH2X+1O) X=1 in, 2,3 ..., for N-alkanes epoxide and/or isomeric alkane epoxide.
The preparation method of above-mentioned dialkoxy xanthate polysulfide, comprises the following steps that
(1) fatty alcohol, powdered sodium hydroxide are joined in organic solvent, at normal temperatures stirring 20-40 minute, then to
System is slowly added to Carbon bisulfide, after having reacted, prepares the mixture of dialkoxy dithiocarbonic acid sodium, fatty alcohol: two sulfur
Change carbon: sodium hydroxide: the mol ratio of organic solvent is (1.0～1.5): (1.0～1.5): 1.0:(5.0～20.0)；
(2) mixture of the dialkoxy dithiocarbonic acid sodium prepared to step (1) is slowly added to Disulfur dichloride, Disulfur dichloride
The mol ratio of addition and Carbon bisulfide be: (0.5～1.0): (1.0～1.5), after dropping, the material obtained is carried out
Sucking filtration, filtrate carries out rotation and steams separation, isolated organic solvent and dialkoxy xanthate polysulfide.
Currently preferred, step (2), the vacuum-0.01～-0.10MPa that rotation steaming separates, temperature is 40～100 DEG C.
The organic solvent that separated goes out collects recycling.
Currently preferred, step (2), the isolated filtering residue of sucking filtration is inorganic salt sodium chloride, after vacuum dried process
As by-product.
Currently preferred, step (1), described organic solvent is aliphatic hydrocarbon organic solvent, cycloalkane organic solvent, virtue
Fragrant hydrocarbon organic solvent, chlorination aromatic hydrocarbon organic solvent, heterocyclic organic solvent, sulfoxide type organic solvent low viscosity are organic molten
Agent, solvent viscosity requires at 20 DEG C less than 5cp@.
It is further preferred that described organic solvent be toluene, dimethylbenzene, benzene, chlorobenzene, normal heptane, No. 120 solvent naphthas,
Paraffin oil, oxolane, carbon dichloride, carbon trichloride or carbon tetrachloride etc..
Currently preferred, step (1), fatty alcohol: Carbon bisulfide: sodium hydroxide: the mol ratio of organic solvent is (1.0
～1.2): (1.0～1.2): 1.0:(5.0～15.0).
Currently preferred, step (1), described fatty alcohol is isopropanol, butanol, ethanol or methanol.
Currently preferred, step (1), the dropping speed of Carbon bisulfide is about 0.9-1.3 gram/minute.
Currently preferred, step (2), described Disulfur dichloride is sulfur monochloride or sulfur dichloride.
Currently preferred, step (2), the rate of addition of Disulfur dichloride is about 0.6-0.9 gram/minute.
Beneficial effect:
1, this preparation method flow process is short, product yield and stay in grade, and production efficiency is high.
2, inorganic salt sodium chloride recovery process is succinct, and without other inorganic salt impurities, purity is high, is conducive to recycling.
3, present invention process produces without waste water, and the most existing technique is more environmentally-friendly.
Accompanying drawing illustrates:
Fig. 1 is the preparation technology flow chart of dialkoxy xanthate polysulfide of the present invention.
Detailed description of the invention
Below in conjunction with embodiment, the present invention will be further described, but is not limited to this.
Embodiment 1
The preparation method of a kind of dialkoxy xanthate polysulfide, as it is shown in figure 1, specifically comprise the following steps that
(1) 60 grams of isopropanols, 40 grams of powdered sodium hydroxides and 460 grams of toluene are joined four mouthfuls of band thermometer and stirring
In flask, stirring 30 minutes at normal temperatures, then weigh 76 grams of Carbon bisulfide with in constant pressure funnel, in 1.0 hours slowly to
Dropping in four-hole boiling flask, drips and prepares the diisopropyl disulfide mixture for sodium formate after complete reaction completes；
(2) weigh 51.5 grams of sulfur dichloride again in constant pressure funnel, slowly dripped in four-hole boiling flask in 1.5 hours
Adding, after dropping, material is carried out sucking filtration, the isolated filtering residue of sucking filtration is inorganic salt sodium chloride, makees after vacuum dried process
For by-product, filtrate is transferred in rotary evaporation bottle, separated at vacuum-0.05MPa and 80 DEG C, isolated toluene
With dialkoxy xanthate polysulfide, toluene solvant collects recycling, the transfer of dialkoxy xanthate polysulfide
In clean vial, yield 99.5%.
Embodiment 2
The preparation method of a kind of dialkoxy xanthate polysulfide, specifically comprises the following steps that
(1) 74 grams of butanol, 40 grams of powdered sodium hydroxides and 550 grams of dimethylbenzene are joined four mouthfuls of band thermometer and stirring
In flask, stirring 40 minutes at normal temperatures, then weigh in 83.6 grams of Carbon bisulfide and constant pressure funnel, in 1.5 hours slowly
Drip in four-hole boiling flask, drip and after complete reaction completes, prepare the diisopropyl disulfide mixture for sodium formate；
(2) weigh 53.5 grams of sulfur dichloride again in constant pressure funnel, slowly dripped in four-hole boiling flask in 1.0 hours
Adding, after dropping, material is carried out sucking filtration, the isolated filtering residue of sucking filtration is inorganic salt sodium chloride, makees after vacuum dried process
For by-product, filtrate is transferred in rotary evaporation bottle, separated at vacuum-0.07MPa and 75 DEG C, isolated diformazan
Benzene and dialkoxy xanthate polysulfide, toluene solvant collection recycling, dialkoxy xanthate polysulfide turns
Move on in clean vial, yield 98.9%.
Embodiment 3
The preparation method of a kind of dialkoxy xanthate polysulfide, specifically comprises the following steps that
(1) 46 grams of ethanol, 40 grams of powdered sodium hydroxides and 500 grams of normal heptane are joined four mouthfuls of band thermometer and stirring
In flask, stirring 35 minutes at normal temperatures, then weigh in 79.8 grams of Carbon bisulfide and constant pressure funnel, in 1.2 hours slowly
Drip in four-hole boiling flask, drip and after complete reaction completes, prepare the diisopropyl disulfide mixture for sodium formate；
(2) weigh 52.5 grams of sulfur dichloride again in constant pressure funnel, slowly dripped in four-hole boiling flask in 1.3 hours
Adding, after dropping, material is carried out sucking filtration, the isolated filtering residue of sucking filtration is inorganic salt sodium chloride, makees after vacuum dried process
For by-product, filtrate is transferred in rotary evaporation bottle, separated at vacuum-0.07MPa and 75 DEG C, isolated positive heptan
Alkane and dialkoxy xanthate polysulfide, toluene solvant collection recycling, dialkoxy xanthate polysulfide turns
Move on in clean vial, yield 99.1%.
Embodiment 4
The preparation method of a kind of dialkoxy xanthate polysulfide, specifically comprises the following steps that
(1) 32 grams of methanol, 40 grams of powdered sodium hydroxides and 678 grams of chlorobenzenes are joined four mouthfuls of burnings of band thermometer and stirring
In Ping, stirring 25 minutes at normal temperatures, then weigh 91.2 grams of Carbon bisulfide with in constant pressure funnel, in 1.5 hours slowly to
Dropping in four-hole boiling flask, drips and prepares the diisopropyl disulfide mixture for sodium formate after complete reaction completes；
(2) weigh 56.7 grams of sulfur dichloride again in constant pressure funnel, slowly dripped in four-hole boiling flask in 1.5 hours
Adding, after dropping, material is carried out sucking filtration, the isolated filtering residue of sucking filtration is inorganic salt sodium chloride, makees after vacuum dried process
For by-product, filtrate is transferred in rotary evaporation bottle, separated at vacuum-0.07MPa and 75 DEG C, isolated chlorobenzene
With dialkoxy xanthate polysulfide, toluene solvant collects recycling, the transfer of dialkoxy xanthate polysulfide
In clean vial, yield 98.1%.
Claims (10)
1. a dialkoxy xanthate polysulfide, structural formula is as follows:
Wherein, alkoxyl (CXH2X+1O) X=1 in, 2,3 ..., for N-alkanes epoxide and/or isomeric alkane epoxide.
2. the preparation method of the dialkoxy xanthate polysulfide described in claim 1, comprises the following steps that
(1) fatty alcohol, powdered sodium hydroxide are joined in organic solvent, at normal temperatures stirring 20-40 minute, then to system
In be slowly added to Carbon bisulfide, after having reacted prepare dialkoxy dithiocarbonic acid sodium mixture, fatty alcohol: curing
Carbon: sodium hydroxide: the mol ratio of organic solvent is (1.0～1.5): (1.0～1.5): 1.0:(5.0～20.0)；
(2) mixture of the dialkoxy dithiocarbonic acid sodium prepared to step (1) is slowly added to Disulfur dichloride, adding of Disulfur dichloride
The mol ratio entering amount and Carbon bisulfide is: (0.5～1.0): (1.0～1.5), is taken out by the material obtained after dropping
Filter, filtrate carries out rotation and steams separation, isolated organic solvent and dialkoxy xanthate polysulfide.
The preparation method of dialkoxy xanthate polysulfide the most according to claim 2, it is characterised in that step
(2), the vacuum-0.01～-0.10MPa separated is steamed in rotation, and temperature is 40～100 DEG C, and the organic solvent that separated goes out is collected
Recycling.
The preparation method of dialkoxy xanthate polysulfide the most according to claim 2, it is characterised in that step
(2), the isolated filtering residue of sucking filtration is inorganic salt sodium chloride, as by-product after vacuum dried process.
The preparation method of dialkoxy xanthate polysulfide the most according to claim 2, it is characterised in that step
(1), described organic solvent is aliphatic hydrocarbon organic solvent, and cycloalkane organic solvent, aromatic hydrocarbon organic solvent, chlorination aromatic hydrocarbon have
Machine solvent, heterocyclic organic solvent, sulfoxide type organic solvent low viscosity organic solvent, solvent viscosity requires to be less than at 20 DEG C
5cp@；It is further preferred that described organic solvent is toluene, dimethylbenzene, benzene, chlorobenzene, normal heptane, No. 120 solvent naphthas, paraffin
Oil, oxolane, carbon dichloride, carbon trichloride or carbon tetrachloride etc..
The preparation method of dialkoxy xanthate polysulfide the most according to claim 2, it is characterised in that step
(1), fatty alcohol: Carbon bisulfide: sodium hydroxide: the mol ratio of organic solvent is (1.0～1.2): (1.0～1.2): 1.0:(5.0
～15.0).
The preparation method of dialkoxy xanthate polysulfide the most according to claim 2, it is characterised in that step
(1), described fatty alcohol is isopropanol, butanol, ethanol or methanol.
The preparation method of dialkoxy xanthate polysulfide the most according to claim 2, it is characterised in that step
(1), the dropping speed of Carbon bisulfide is about 0.9-1.3 gram/minute.
The preparation method of dialkoxy xanthate polysulfide the most according to claim 2, it is characterised in that step
(2), described Disulfur dichloride is sulfur monochloride or sulfur dichloride.
The preparation method of dialkoxy xanthate polysulfide the most according to claim 2, it is characterised in that step
(2), the rate of addition of Disulfur dichloride is about 0.6-0.9 gram/minute.
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| CN201610438177.9A CN106083679A (en) | 2016-06-17 | 2016-06-17 | A kind of preparation method of dialkoxy xanthate polysulfide |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111870862A (en) * | 2020-07-29 | 2020-11-03 | 沈阳有研矿物化工有限公司 | Harmless treatment method for waste salt in production of alkylxanthate beneficiation reagent |
| CN114920677A (en) * | 2022-04-14 | 2022-08-19 | 鹤壁中昊新材料科技有限公司 | Synthesis process of rubber accelerator diisopropyl xanthogen disulfide |
| CN115536562A (en) * | 2022-10-12 | 2022-12-30 | 鹤壁元昊新材料集团股份有限公司 | Preparation method of alkyl xanthate tetrasulfide |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1634924A (en) * | 1926-01-27 | 1927-07-05 | Roessler & Hasslacher Chemical | Accelerator for the vulcanization of rubber |
| US2374385A (en) * | 1941-05-17 | 1945-04-24 | Goodrich Co B F | Vulcanization of copolymers of conjugated diene hydrocarbons and alpha-methylene nitriles |
-
2016
- 2016-06-17 CN CN201610438177.9A patent/CN106083679A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1634924A (en) * | 1926-01-27 | 1927-07-05 | Roessler & Hasslacher Chemical | Accelerator for the vulcanization of rubber |
| US2374385A (en) * | 1941-05-17 | 1945-04-24 | Goodrich Co B F | Vulcanization of copolymers of conjugated diene hydrocarbons and alpha-methylene nitriles |
Non-Patent Citations (1)
| Title |
|---|
| 杜学军，等: "异丙基黄原酸酯多硫化物合成工艺的研究", 《橡胶科技》 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111870862A (en) * | 2020-07-29 | 2020-11-03 | 沈阳有研矿物化工有限公司 | Harmless treatment method for waste salt in production of alkylxanthate beneficiation reagent |
| CN114920677A (en) * | 2022-04-14 | 2022-08-19 | 鹤壁中昊新材料科技有限公司 | Synthesis process of rubber accelerator diisopropyl xanthogen disulfide |
| CN115536562A (en) * | 2022-10-12 | 2022-12-30 | 鹤壁元昊新材料集团股份有限公司 | Preparation method of alkyl xanthate tetrasulfide |
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