CN101838228B - Clean synthesis method for di-tert-butyl disulfide - Google Patents
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- CN101838228B CN101838228B CN2010101980155A CN201010198015A CN101838228B CN 101838228 B CN101838228 B CN 101838228B CN 2010101980155 A CN2010101980155 A CN 2010101980155A CN 201010198015 A CN201010198015 A CN 201010198015A CN 101838228 B CN101838228 B CN 101838228B
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Abstract
The invention belongs to the field of organic synthesis and particularly relates to a clean synthesis method for di-tert-butyl disulfide, which comprises the following steps: adding tert-butyl mercaptan, a catalyst and a solvent, i.e. acetone, into a reactor container, or only adding the tert-butyl mercaptan and the catalyst into the reactor container firstly and then adding an oxidizer, i.e. oxyful, or a mixture of acetone and oxyful into the reactor container with stirring; controlling a reaction temperature between minus 20 DEG C and 70 DEG C to perform a reaction sufficiently; after the reaction is completed, post-processing the obtained product to obtain the di-tert-butyl disulfide, wherein the catalyst is cuprous chloride, copper chloride or a mixture of the cuprous chloride and the copper chloride in random mass proportion. The invention meets the requirement for clean production. The catalyst and the reaction solvent have low price, can be conveniently recycled, have small usage in the reaction and have excellent catalytic performance. Meanwhile, the process has short reaction time, the conversion rate of the tert-butyl mercaptan reaches 98 to 100 percent, the selectivity of the di-tert-butyl disulfide is between 90 and 96 percent, the reaction yield is high and the clean synthesis method is suitable for industrial production.
Description
(1) technical field
The invention belongs to the organic synthesis field, particularly a kind of clean synthesis method of di-tert-butyl disulfide.
(2) background technology
Disulfide has important use to be worth in Food science, biological chemistry and flavor chemistry field.At first in industry, organic disulfide is applied to tree elastomer, viton and elastomerics as vulcanizing agent, gives their good tensile strength; The organic disulfide extreme-pressure additive is one type of important oil dope in addition, and the withstand load ability is big, and corrodibility is little, has superior high temperature extreme pressure property, is widely used in the lubricating oil extreme-pressure anti-wear, fields such as metal processing extreme boundary lubrication.From synthetic and biochemical viewpoint, organic disulfide is the important intermediate of synthetic sulfenylation compound, oxysulfide.
The English Di-tert-butyl-disulfide by name of di-tert-butyl disulfide, molecular formula is (CH
3)
3C-S-S-C (CH
3)
3, be a kind of important organic synthesis intermediate, can synthesize a lot of important organism by it, application prospect is boundless aspect chemistry, biology and organic materials.Its structure is complicated than the structure of other symmetrical butyl disulfides.The preparation route of di-tert-butyl disulfide can be divided into two big types according to raw material.A kind of is to be raw material with tertiary butyl halogen (tertiary butyl chloride and tert.-butyl bromide), warp and disulphide (like sodium disulfide etc.) prepared in reaction disulfide.But, when the preparation di-tert-butyl disulfide, because the tertiary butyl is sterically hindered bigger in the tertiary butyl halogen, the preparation difficulty, effect is relatively poor.In order to obtain the reaction conditions that satisfied productive rate generally need be strengthened.Be reported in use solvent N like document, dinethylformamide (DMF), phase-transfer catalyst PEG-400, and under microwave reinforced condition, be substrate with the tertiary butyl chloride, the di-tert-butyl disulfide productive rate can reach 90%.But this system is complicated, and catalyzer, solvent all reclaim than difficult, and uses NaOH; And be microwave reaction; Its industrial applications (reference Jin-Xian Wang, Li-juan Gao, Dan-feng Huang.A rapid and efficient synthesis of symmetricaldisulfides under microwave irradiation conditions [J] .SyntheticCommunications have been limited; 2002,32 (7): 963-969).Another kind is to be main raw material with the tert-butyl mercaptan, uses the oxygenant oxidation to prepare di-tert-butyl disulfide.The oxygenant of being selected for use has bromine, ydrogen peroxide 50, metal-salt etc.For the direct reaction system of using metal-salt such as cupric chloride as oxygenant; Though reaction yield, selectivity are all better; But what be to use is a large amount of cupric chloride (mercaptan molar weight 4 times), and catalyzer will recycle, and uses toxicity, the higher acetonitrile of price to be solvent; Higher (the reference KimYong Hae of cost; Shinhama Koichi, Oae Shigeru.New synthesis of alkylpolysulfides by treatment of thiols, disulfides and thionitrites withanhydrous copper (II) chloride [J] .Bulletin of the Chemical Society ofJapan; 1979,52 (10): 3117-3118.).And document is the method that oxygenant prepares di-tert-butyl disulfide with the bromine; Can obtain 97% yield; But system need be used a large amount of silica gel; Perhaps need alkali (organic bases or mineral alkali) as Fu's acid agent, and the bromine price is higher, higher (the reference Mohammed Hashmat Ali of the cost of preparation; Mario McDermott.Oxidation of thiols todisulfides with molecular bromine on hydrated silica gelsupport [J] .Tetrahedron Letters, 43 (2002): 62716273).And the method that document prepares di-tert-butyl disulfide with nitrogen chlorosuccinimide (NCS) oxidation tert-butyl mercaptan is under the condition that the methylene dichloride medium exists, to be di-tert-butyl disulfide with nitrogen chlorosuccinimide (NCS) oxidation tert-butyl mercaptan; The yield of this method is 80%; This method nitrogen chlorosuccinimide (NCS) price is higher; And oxygenant NCS is to light and moisture-sensitive; Need anhydrous, dark place operation, aftertreatment needs a large amount of alkali lye, the yield of reaction also lower (80%) (reference Hashemi Mohammed; Ghafuri Hossein; Karimi-Jaberi Zahed.N-Chlorosuccinimide:A simple and efficientreagent for the preparation of symmetrical disulfides [J] .Journal ofSulfur Chemistry, 2006,27 (2): 165-167).And use the scheme of methyl-sulphoxide as oxygenant, though selectivity, productive rate are all higher, the reaction times is longer; The trichlorine molybdous oxide complex compound catalyst of particularly employed methyl-sulphoxide complexing is difficult for reclaiming; And cost an arm and a leg, limited its industrial applications (reference Li Wen, Zhang Yadong; Fan Lulu. the method [P] of the synthetic di-tert-butyl disulfide of the trichlorine molybdous oxide catalysis of methyl-sulphoxide (DMSO) complexing, number of patent application: CN200910065348.8).And use chromic acid cerium salt [Ce (NO
3)
3]
2CrO
4Being the scheme of oxygenant, is solvent with benzene, and long reaction time, yield are low to be 80%.(reference Firouzabadi H., Iranpoor N., Parham H., et al.Oxidation of thiols to their disulfides with bis [trinitratocerium (IV)] chromate [Ce (NO
3)
3]
2CrO
4And pyridinum chlorochromate [J] .SyntheticCommunications, 1984,14 (8): 717-723).
(3) summary of the invention
The object of the present invention is to provide a kind of clean synthesis method of di-tert-butyl disulfide, overcome in the prior art or use the big or catalyzer of solvent toxicity to be difficult for defectives such as recoverys, cost height, suitable industrial applications.
The technical scheme that the present invention adopts is following:
A kind of clean synthesis method of di-tert-butyl disulfide; With in tert-butyl mercaptan, catalyzer, the solvent acetone adding reaction vessel or only with in tert-butyl mercaptan, the catalyzer elder generation adding reaction vessel; Stir the mixture that adds oxidant hydrogen peroxide or acetone and ydrogen peroxide 50 down; Control reaction temperature is fully reaction between-20 ℃ to 70 ℃, reaction finish after aftertreatment get final product described di-tert-butyl disulfide; Described catalyzer is the mixture of cuprous chloride, cupric chloride or both any mass ratios.
Tert-butyl mercaptan is 1: 0.0005～0.05: 0.5～1 with the amount of substance ratio that feeds intake of catalyzer, ydrogen peroxide 50, preferred 1: 0.001～0.01: 0.5～0.75; The TV that solvent acetone adds and the volume ratio of tert-butyl mercaptan are 1～9: 1.
Described ydrogen peroxide 50 massfraction (H
2O
2Quality/(H
2O
2Quality+H
2The quality of O) * 100% be 10～75%), preferably use the ydrogen peroxide 50 of 27.5%, 30%, 35%, 50% specification of stipulating in the national standard; More than relate to the part of ydrogen peroxide 50 charging capacity, with the hydrogen peroxide (H in the ydrogen peroxide 50
2O
2) the amount of substance meter.
Temperature of reaction preferably is controlled at-10～60 ℃.
Concrete, in experimentation, whether fully monitor for reaction, adopt the mercaptans content in the GC-9800 type gas chromatographic detection reaction product: capillary column SE-54, Φ 1 μ m (I.D.) * 30m; The hydrogen flame ion detects: 260 ℃ of sensing chamber's temperature, and 260 ℃ of temperature of vaporization chamber, carrier gas is a nitrogen, presses 0.045MPa before the post; Take temperature programming: 70 ℃ of initial temperatures, keep 6min, the speed with 20 ℃/min is raised to 240 ℃ then, keeps 3min.If reach 98%～100% through detecting the tert-butyl mercaptan transformation efficiency, promptly can be considered sufficient reacting, stopped reaction.
Described aftertreatment is removed acetone again for removing by filter catalyzer, and standing demix is got oil phase.
The present invention has following advantage with respect to prior art:
The present invention uses ydrogen peroxide 50 to be oxygenant, only generates water byproduct, meets the requirement of cleaner production; Use cuprous chloride, cupric chloride or both mixtures to be catalyzer, with methyl-sulphoxide (DMSO), nitrogen chlorosuccinimide (NCS), chromic acid cerium salt ([Ce (NO
3)
3]
2CrO
4), Br
2, I
2Compare cheaply in oxygenant, and can conveniently reclaim, consumption is few in reaction, and catalytic performance is good; According to the characteristics that this reaction tert-butyl mercaptan and ydrogen peroxide 50 do not dissolve each other mutually, it is reaction solvent that body series is selected acetone, and intermiscibility is good; Compare with acetonitrile or hexafluoroisopropanol equal solvent that tradition adopts; Its convenient sources, price is cheaper, reclaims easy the recycling; Obvious energy conservation, the explained hereafter cost is low.Simultaneously, this technological reaction time is short, and speed of response is fast, and the tert-butyl mercaptan transformation efficiency is up to 98%～100%, and di-tert-butyl disulfide selectivity 90%～96%, reaction yield height are suitable for suitability for industrialized production.
(4) description of drawings
Fig. 1 is the mass spectrum of the di-tert-butyl disulfide that obtains among the embodiment.
(5) embodiment:
Below with specific embodiment technical scheme of the present invention is described, but protection scope of the present invention is not limited thereto:
Adopt the mercaptans content in GC-9800 type gc (Shanghai Kechuang Chromatograph Instruments Co., Ltd.) the detection reaction product in following examples: capillary column SE-54, Φ 1 μ m (I.D.) * 30m, the Lanzhou Chemistry and Physics Institute of the Chinese Academy of Sciences; The hydrogen flame ion detects: 260 ℃ of sensing chamber's temperature, and 260 ℃ of temperature of vaporization chamber, carrier gas is a nitrogen, presses 0.045MPa before the post; Take temperature programming: 70 ℃ of initial temperatures, keep 6min, be raised to 240 ℃ with the speed of 20 ℃/min, keep 3min.
Embodiment 1
In reaction vessel, add Catalysts Cu Cl 2.18mmol; Acetone 100mL; Add tert-butyl mercaptan (t-Bu-SH) 867mmol; Agitation condition adds the ydrogen peroxide 50 54g (476.5mmol) of 30% (massfraction of hydrogen peroxide in the ydrogen peroxide 50, down together) and the mixed solution of 150mL acetone, [n (CuCl): n (t-Bu-SH): n (H down
2O
2)=2.5: 1000: 550 (representing each amount of substance ratio, down together), the TV that solvent acetone adds and the volume ratio of tert-butyl mercaptan are 2.5: 1], control reaction temperature is between 40 ± 5 ℃, and reaction is to reaching 99.8%, stopped reaction through detection mercaptan transformation efficiency.Remove by filter catalyzer, and then remove acetone, behind the standing demix, get oil reservoir and be di-tert-butyl disulfide, selectivity reaches 94.5%.Mass spectrum is seen Fig. 1, molecular ion peak 178, base peak 57.
Embodiment 2
In reaction vessel, add Catalysts Cu Cl 0.0434mmol, acetone 20mL adds tert-butyl mercaptan 86.7mmol, the ydrogen peroxide 50 3.5g (51.5mmol) of adding 50% and the mixed solution of 10mL acetone under the agitation condition, [n (CuCl): n (t-Bu-SH): n (H
2O
2)=0.50: 1000: 594, the TV that solvent acetone adds and the volume ratio of tert-butyl mercaptan are 3.0: 1], control reaction temperature is at 35 ± 5 ℃, and reaction is to reaching 99.6%, stopped reaction through detecting the mercaptan transformation efficiency.Remove by filter catalyzer, and then remove acetone, behind the standing demix, get oil reservoir and be di-tert-butyl disulfide, selectivity reaches 93.8%.Mass spectrum is seen Fig. 1.
Embodiment 3
In reaction vessel, add Catalysts Cu Cl 0.0606mmol, acetone 20mL adds tert-butyl mercaptan 86.7mmol, the ydrogen peroxide 50 2.2g (48.5mmol) of adding 75% and the mixed solution of 10mL acetone under the agitation condition, [n (CuCl): n (t-Bu-SH): n (H
2O
2)=0.699: 1000: 560, the TV that solvent acetone adds and the volume ratio of tert-butyl mercaptan are 3.0: 1], control reaction temperature is at 40 ± 3 ℃, and reaction to warp detects the mercaptan transformation efficiency and reaches 98.4%, i.e. stopped reaction.Remove by filter catalyzer, and then remove acetone, behind the standing demix, get oil reservoir and be di-tert-butyl disulfide, selectivity reaches 93.7%.Mass spectrum is seen Fig. 1.
Embodiment 4
In reaction vessel, add Catalysts Cu Cl 0.263mmol, acetone 20mL adds tert-butyl mercaptan 86.7mmol, the ydrogen peroxide 50 5g (44mmol) of adding 30% and the mixed solution of 10mL acetone under the agitation condition, [n (CuCl): n (t-Bu-SH): n (H
2O
2)=3: 1000: 507, the TV that solvent acetone adds and the volume ratio of tert-butyl mercaptan are 3.0: 1], control reaction temperature is at 20 ± 5 ℃, and reaction is to reaching 99.6%, stopped reaction through detecting the mercaptan transformation efficiency.Remove by filter catalyzer, and then remove acetone, behind the standing demix, get oil reservoir and be di-tert-butyl disulfide, selectivity reaches 93.8%.Mass spectrum is seen Fig. 1.
Embodiment 5
In reaction vessel, add Catalysts Cu Cl 5.05mmol, acetone 300mL adds tert-butyl mercaptan 2000mmol, the ydrogen peroxide 50 69.4g (1021mmol) of adding 50% and the mixed solution of 200mL acetone under the agitation condition, [n (CuCl): n (t-Bu-SH): n (H
2O
2)=2.53: 1000: 510.5, the TV that solvent acetone adds and the volume ratio of tert-butyl mercaptan are 2.2: 1], control reaction temperature is at 35 ± 5 ℃, and reaction is to reaching 99.2%, stopped reaction through detecting the mercaptan transformation efficiency.Remove by filter catalyzer, and then remove acetone, behind the standing demix, get oil reservoir and be di-tert-butyl disulfide, selectivity reaches 94.4%.
Embodiment 6
In reaction vessel, add Catalysts Cu Cl 5.6mmol, acetone 200mL adds tert-butyl mercaptan 2000mmol, the ydrogen peroxide 50 70g (1029mmol) of adding 50% and the mixed solution of 200mL acetone under the agitation condition, [n (CuCl): n (t-Bu-SH): n (H
2O
2)=2.8: 1000: 514.5, the TV that solvent acetone adds and the volume ratio of tert-butyl mercaptan are 1.8: 1], control reaction temperature is at 35 ± 4 ℃, and reaction is to reaching 99.1%, stopped reaction through detecting the mercaptan transformation efficiency.Remove by filter catalyzer, and then remove acetone, behind the standing demix, get oil reservoir and be di-tert-butyl disulfide, selectivity reaches 92.9%.Mass spectrum is seen Fig. 1.
Embodiment 7
In reaction vessel, add Catalysts Cu Cl 12mmol, acetone 600mL adds tert-butyl mercaptan 4000mmol, the ydrogen peroxide 50 230g (2030mmol) of adding 30% and the mixed solution of 400mL acetone under the agitation condition, [n (CuCl): n (t-Bu-SH): n (H
2O
2)=3: 1000: 507.5, the TV that solvent acetone adds and the volume ratio of tert-butyl mercaptan are 2.2: 1], control reaction temperature is at 40 ± 3 ℃, and reaction is to reaching 99.4%, stopped reaction through detecting the mercaptan transformation efficiency.Remove by filter catalyzer, and then remove acetone, behind the standing demix, get oil reservoir and be di-tert-butyl disulfide, selectivity reaches 94.1%.Mass spectrum is seen Fig. 1.
Embodiment 8
In reaction vessel, add Catalysts Cu Cl 10mmol, acetone 400mL adds tert-butyl mercaptan 4000mmol, the ydrogen peroxide 50 150g (2210mmol) of adding 50% and the mixed solution of 400mL acetone under the agitation condition, [n (CuCl): n (t-Bu-SH): n (H
2O
2)=2.5: 1000: 552.5, the TV that solvent acetone adds and the volume ratio of tert-butyl mercaptan are 1.8: 1], control reaction temperature is at 45 ± 5 ℃, and reaction is to reaching 99.2%, stopped reaction through detecting the mercaptan transformation efficiency.Remove by filter catalyzer, and then remove acetone, behind the standing demix, get oil reservoir and be di-tert-butyl disulfide, selectivity reaches 94.2%.Mass spectrum is seen Fig. 1.
Embodiment 9
In reactor drum, add Catalysts Cu Cl 5mmol, acetone 30ml adds tert-butyl mercaptan 100mmol, and agitation condition adds 50% ydrogen peroxide 50 5.1g (75mmol) (not adding acetone this moment), [n (CuCl): n (t-Bu-SH): n (H down
2O
2)=50: 1000: 750, the TV that solvent acetone adds and the volume ratio of tert-butyl mercaptan are 2.6: 1], control reaction temperature is at 40 ± 5 ℃, and reaction is to reaching 98%, stopped reaction through detecting the mercaptan transformation efficiency.Remove by filter catalyzer, and then remove acetone, behind the standing demix, get oil reservoir and be di-tert-butyl disulfide, selectivity reaches 92.1%.Mass spectrum is seen Fig. 1.
In reaction vessel, add Catalysts Cu Cl
20.0434mmol acetone 20mL adds tert-butyl mercaptan 86.7mmol, the ydrogen peroxide 50 3.0g (44.1mmol) of adding 50% and the mixed solution of 10mL acetone under the agitation condition, [n (CuCl): n (t-Bu-SH): n (H
2O
2)=0.5: 1000: 509, the TV that solvent acetone adds and the volume ratio of tert-butyl mercaptan are 3.0: 1], control reaction temperature is at 45 ± 3 ℃, and reaction is to reaching 98.9%, stopped reaction through detecting the mercaptan transformation efficiency.Remove by filter catalyzer, and then remove acetone, behind the standing demix, get oil reservoir and be di-tert-butyl disulfide, selectivity reaches 92.3%.Mass spectrum is seen Fig. 1.
Embodiment 11
In reaction vessel, add Catalysts Cu Cl 0.074mmol, CuCl
20.0263mmol acetone 20mL adds tert-butyl mercaptan 86.7mmol, the ydrogen peroxide 50 3.5g (51.5mmol) of adding 50% and the mixed solution of 10mL acetone under the agitation condition, [n (CuCl): n (CuCl
2): n (t-Bu-SH): n (H
2O
2)=0.85: 0.30: 1000: 594, the TV that solvent acetone adds and the volume ratio of tert-butyl mercaptan are 3.0: 1], control reaction temperature is at 45 ± 4 ℃, and reaction is to reaching 98.9%, stopped reaction through detecting the mercaptan transformation efficiency.Remove by filter catalyzer, and then remove acetone, behind the standing demix, get oil reservoir and be di-tert-butyl disulfide, selectivity reaches 93.4%.Mass spectrum is seen Fig. 1.
Embodiment 12
In reactor drum, add Catalysts Cu Cl 0.526mmol, add tert-butyl mercaptan 100mmol, the ydrogen peroxide 50 5.1g (75mmol) of adding 50% and mixed solution [n (CuCl): the n (t-Bu-SH): n (H of 40ml acetone under the agitation condition
2O
2)=5.3: 1000: 750, the TV that solvent acetone adds and the volume ratio of tert-butyl mercaptan are 3.5: 1], control reaction temperature is at 40 ± 5 ℃, and reaction is to reaching 99.1%, stopped reaction through detecting the mercaptan transformation efficiency.Remove by filter catalyzer, and then remove acetone, behind the standing demix, get oil reservoir and be di-tert-butyl disulfide, selectivity reaches 92.7%.Mass spectrum is seen Fig. 1.
Claims (4)
1. the clean synthesis method of a di-tert-butyl disulfide; It is characterized in that, tert-butyl mercaptan, catalyzer, solvent acetone are added in the reaction vessel, stir the mixture that adds oxidant hydrogen peroxide or acetone and ydrogen peroxide 50 down; Or only add tert-butyl mercaptan, catalyzer in the reaction vessel earlier; Stir the mixture that adds acetone and ydrogen peroxide 50 down, control reaction temperature is fully reaction between-20 ℃ to 70 ℃, the reaction end after aftertreatment get final product described di-tert-butyl disulfide; Described catalyzer is the mixture of cuprous chloride, cupric chloride or both any mass ratios; Tert-butyl mercaptan feeds intake amount of substance than being 1:0.0005～0.05:0.5～1 with catalyzer, ydrogen peroxide 50; The TV that solvent acetone adds and the volume ratio of tert-butyl mercaptan are 1～9:1.
2. the clean synthesis method of di-tert-butyl disulfide as claimed in claim 1 is characterized in that, tert-butyl mercaptan feeds intake amount of substance than being 1:0.001～0.01:0.5～0.75 with catalyzer, ydrogen peroxide 50.
3. the clean synthesis method of di-tert-butyl disulfide as claimed in claim 1 is characterized in that, temperature of reaction is controlled at-10 ℃～60 ℃.
4. the clean synthesis method of di-tert-butyl disulfide as claimed in claim 1 is characterized in that, described ydrogen peroxide 50 massfraction is 10%～75%.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5231114A (en) * | 1990-06-22 | 1993-07-27 | Wakunaga Seiyaku Kabushiki Kaisha | Polysulfides compounds and lipid peroxidation inhibitor containing the polysulfide compounds as active ingredient |
| CN101704772A (en) * | 2009-11-19 | 2010-05-12 | 郑州大学 | Method for preparing isopropyl mercaptan |
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2010
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5231114A (en) * | 1990-06-22 | 1993-07-27 | Wakunaga Seiyaku Kabushiki Kaisha | Polysulfides compounds and lipid peroxidation inhibitor containing the polysulfide compounds as active ingredient |
| CN101704772A (en) * | 2009-11-19 | 2010-05-12 | 郑州大学 | Method for preparing isopropyl mercaptan |
Non-Patent Citations (2)
| Title |
|---|
| New synthesis of alkyl polysulfides by treatment of thiols, disulfides and thionitrites with anhydrous Copper(Ⅱ) Chloride;Yong Hae Kim et al.,;《Bulletin of the Chemical Society of Japan》;19791031;第52卷(第10期);3117-3118 * |
| Yong Hae Kim et al.,.New synthesis of alkyl polysulfides by treatment of thiols, disulfides and thionitrites with anhydrous Copper(Ⅱ) Chloride.《Bulletin of the Chemical Society of Japan》.1979,第52卷(第10期),3117-3118. |
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