CN110876962A - Catalyst for catalytic preparation of tert-dodecyl mercaptan and preparation method thereof - Google Patents
Catalyst for catalytic preparation of tert-dodecyl mercaptan and preparation method thereof Download PDFInfo
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- CN110876962A CN110876962A CN201911308908.8A CN201911308908A CN110876962A CN 110876962 A CN110876962 A CN 110876962A CN 201911308908 A CN201911308908 A CN 201911308908A CN 110876962 A CN110876962 A CN 110876962A
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- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
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- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
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- C07C319/02—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of thiols
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Abstract
A catalyst for preparing tert-dodecyl mercaptan by catalysis and a preparation method thereof belong to the field of catalysts for preparing tert-dodecyl mercaptan by catalysis. The catalyst is an acidic liquid prepared from anhydrous aluminum chloride, an aromatic hydrocarbon assistant and a chloralkane assistant, wherein the molar ratio of the anhydrous aluminum chloride to the aromatic hydrocarbon assistant to the chloralkane assistant is 1: 0.5-5: 0.1-1, the aromatic hydrocarbon assistant is benzene, toluene, ethylbenzene, xylene, chlorobenzene and nitrobenzene, and the chloralkane assistant is methane chloride, dichloromethane, trichloromethane, monochloroethane and dichloroethane. The method comprises the following steps: and (2) rapidly adding anhydrous aluminum chloride into the aromatic hydrocarbon auxiliary agent in batches while stirring, then dropwise adding the chloroalkane auxiliary agent under the condition of temperature-controlled stirring, and continuing to perform temperature-controlled stirring reaction for a certain time after completing dropwise adding to prepare the catalyst for catalytically preparing tert-dodecyl mercaptan. The selectivity of the tertiary dodecyl mercaptan prepared by the method is over 98 percent, and the catalytic reaction condition is mild.
Description
Technical Field
The invention belongs to the field of catalysts for catalytic reaction of tertiary dodecyl mercaptan; in particular to a catalyst for preparing tert-dodecyl mercaptan by catalysis and a preparation method thereof.
Background
The tert-dodecyl mercaptan is mainly used as a molecular weight regulator in the polymerization reaction process of ABS resin, styrene-butadiene rubber, nitrile rubber and high impact polystyrene product production, can also be used as a stabilizer and an antioxidant of polyolefin such as polyvinyl chloride, polyethylene and the like, and can also be used for synthesizing certain products such as medicines, nonionic surfactants, lubricating oil additives, insecticides, bactericides, spices and the like.
Tert-dodecyl mercaptan is generally synthesized by the addition reaction of mixed dodecenes (tetrapropylene or triisobutylene) with hydrogen sulfide. The main catalysts are: lewis acid catalyst, zeolite molecular sieve, ion exchange resin and solid super acid. Although the catalytic method using solid-phase catalysts such as zeolite molecular sieves, ion exchange resins, solid superacids and the like has the characteristics of environmental protection, the catalytic method has the major defects of short service life of the catalyst, volatile activity, unstable catalytic reaction selectivity and the like which are not beneficial to industrial production.
The first Lewis acid catalyst used for the synthesis of tertiary dodecyl mercaptan was BF3. Due to BF3Expensive price, high activity, high toxicity, difficult storage and treatment, and strict requirements on reaction conditions (low temperature below 5 ℃ and large cold consumption), so the AlCl is gradually used3Instead. Due to solid AlCl3Is not compatible with mixed dodecenes, and solid AlCl is directly used3When used as a catalyst, the catalyst has poor mass transfer efficiency and low reaction activity. In 1979, the United WEB chemical plant of Democratic Germany proposed the use of AlCl3The-methyl phenyl ether-benzene mixed catalyst catalyzes the addition reaction of the mixed dodecene and hydrogen sulfide, so that the reaction catalyst becomes liquid, and the mass transfer capacity is effectively improved. In 1983, in order to increase the chlorine content of the catalytic system, AlCl was proposed in combination with a WEB chemical plant3The toluene-HCl mixture is used as the catalyst, so that a good effect is achieved, but the adopted hydrogen chloride gas with high toxicity and high corrosivity greatly increases the difficulty of catalyst preparation.
Disclosure of Invention
The invention aims to provide a catalyst for preparing tert-dodecyl mercaptan by catalysis and a preparation method thereof, wherein the catalyst has high catalytic efficiency.
The invention is realized by the following technical scheme:
the catalyst for preparing tert-dodecyl mercaptan in a catalytic manner is mainly prepared from anhydrous aluminum chloride, an aromatic hydrocarbon assistant and a chloralkane assistant, wherein the molar ratio of the anhydrous aluminum chloride to the aromatic hydrocarbon assistant to the chloralkane assistant is 1: 0.5-5: 0.1-1.
The invention relates to a catalyst for preparing tert-dodecyl mercaptan by catalysis, wherein an aromatic hydrocarbon auxiliary agent is one of benzene, toluene, ethylbenzene, xylene, chlorobenzene and nitrobenzene.
The catalyst for preparing tert-dodecyl mercaptan in a catalytic manner is characterized in that the chloralkane auxiliary agent is one of methane chloride, dichloromethane, trichloromethane, monochloroethane and dichloroethane.
The catalyst for preparing tert-dodecyl mercaptan by catalysis is characterized in that the molar ratio of the anhydrous aluminum chloride to the aromatic hydrocarbon auxiliary agent to the chloralkane auxiliary agent is 1:2: 0.5.
The catalyst for preparing tert-dodecyl mercaptan by catalysis is characterized in that the molar ratio of the anhydrous aluminum chloride to the aromatic hydrocarbon auxiliary agent to the chloralkane auxiliary agent is 1:5: 1.
The catalyst for preparing tert-dodecyl mercaptan by catalysis is characterized in that the molar ratio of the anhydrous aluminum chloride to the aromatic hydrocarbon auxiliary agent to the chloralkane auxiliary agent is 1:0.5: 0.1.
The catalyst for preparing tert-dodecyl mercaptan by catalysis is acidic liquid, and the pH value is less than or equal to 5.
The preparation method of the catalyst for preparing tert-dodecyl mercaptan comprises the following steps:
step one, respectively weighing a certain mass of anhydrous aluminum chloride, an aromatic hydrocarbon assistant and a chloralkane assistant according to a molar ratio for later use; step two, rapidly adding weighed anhydrous aluminum chloride into the aromatic hydrocarbon auxiliary agent weighed in the step one while stirring, and uniformly mixing; and thirdly, dropwise adding the weighed chloralkane assistant under the condition of temperature-controlled stirring for 0.1-1 h, continuing to perform temperature-controlled stirring reaction for 0.1-1 h after the dropwise adding is finished, and recovering to room temperature to prepare the acidic liquid catalyst for catalytic preparation of tert-dodecyl mercaptan.
The preparation method of the catalyst for preparing tert-dodecyl mercaptan in a catalytic manner comprises the third step of controlling the stirring temperature at 20-60 ℃ and the stirring speed at 50-500 r/min.
The invention relates to an application of a catalyst for catalyzing and preparing tert-dodecyl mercaptan, and the catalyst for catalyzing and preparing tert-dodecyl mercaptan is used for catalyzing the synthesis reaction of tert-dodecyl mercaptan.
The catalyst is used for catalyzing the synthetic reaction of tetrapropylene or triisobutene and hydrogen sulfide to prepare tert-dodecyl mercaptan.
The catalyst for preparing tert-dodecyl mercaptan by catalysis provided by the invention effectively provides a chlorine source through chemical and physical changes of anhydrous aluminum chloride, an aromatic hydrocarbon auxiliary agent and a chloralkane auxiliary agent after being mixed under specific conditions, is easy to operate and treat, is safer and more convenient in the preparation process of the catalyst, and solves the problems of harsh catalytic reaction conditions, complex preparation operation of the catalyst and low catalytic reaction selectivity existing in the existing method for preparing tert-dodecyl mercaptan by homogeneous addition of mixed dodecene and hydrogen sulfide.
The catalyst for preparing tert-dodecyl mercaptan in a catalytic manner is used for catalytically synthesizing tert-butyl mercaptan, tert-amyl mercaptan, tert-hexyl mercaptan, tert-heptyl mercaptan, tert-octyl mercaptan, tert-nonyl mercaptan, tert-decyl mercaptan, tert-undecyl mercaptan and other branched chain mercaptans, the catalytic reaction selectivity is over 95 percent, and the reaction condition is mild.
The catalyst for preparing tert-dodecyl mercaptan by catalysis has the advantages of catalytic synthesis of tert-dodecyl mercaptan, catalytic reaction selectivity of over 98 percent and mild reaction conditions.
Detailed Description
The first embodiment is as follows:
the catalyst for preparing tert-dodecyl mercaptan by catalysis is mainly prepared from anhydrous aluminum chloride, an aromatic hydrocarbon auxiliary agent and a chloralkane auxiliary agent, wherein the molar ratio of the anhydrous aluminum chloride to the aromatic hydrocarbon auxiliary agent to the chloralkane auxiliary agent is 1:5: 1.
In the catalyst for catalytic preparation of tertiary dodecyl mercaptan, the aromatic hydrocarbon auxiliary agent is benzene.
In the catalyst for catalytic preparation of tert-dodecyl mercaptan, the chloroalkane auxiliary agent is methyl chloride.
The second embodiment is as follows:
according to the first embodiment, the preparation method of the catalyst for catalytically preparing tert-dodecyl mercaptan comprises the following steps:
step one, respectively weighing a certain mass of anhydrous aluminum chloride, an aromatic hydrocarbon assistant and a chloralkane assistant according to a molar ratio for later use; step two, rapidly adding weighed anhydrous aluminum chloride into the aromatic hydrocarbon auxiliary agent weighed in the step one while stirring, and uniformly mixing; and step three, dropwise adding the weighed chloralkane assistant under the condition of temperature-controlled stirring for 0.5h, continuing to perform temperature-controlled stirring reaction for 0.5h after dropwise adding is finished, and recovering to room temperature to prepare the acidic liquid catalyst for catalytic preparation of tert-dodecyl mercaptan.
In the preparation method of the catalyst for catalytic preparation of tertiary dodecyl mercaptan, the temperature is controlled at 30 ℃ in the third step, and the stirring speed is 100 r/min.
The catalyst for catalytic preparation of tert-dodecyl mercaptan, which is prepared by the preparation method of the catalyst for catalytic preparation of tert-dodecyl mercaptan according to the embodiment, is an acidic liquid, and the pH value is less than or equal to 5.
The third concrete implementation mode:
the application of the catalyst for catalyzing and preparing tert-dodecyl mercaptan in the first embodiment is used for catalyzing the synthetic reaction of tetrapropylene and hydrogen sulfide.
In the application of the catalyst for catalytic preparation of tertiary dodecyl mercaptan, 100g of tetrapropylene is added into a 250ml four-neck flask, 9g of the prepared catalyst for catalytic preparation of tertiary dodecyl mercaptan is added dropwise under stirring, the introduction amount of hydrogen sulfide is controlled to be 30g/h, the temperature of a reaction solution in the four-neck flask is controlled to be 20-25 ℃, the introduction of hydrogen sulfide is stopped after 1h, stirring is continued for 20 minutes, 126.2g of the reaction solution is obtained, sampling analysis is performed, and the weight composition of the reaction solution is as follows: 11.73 wt% of dodecene, 79.64 wt% of t-dodecyl mercaptan, 1.41 wt% of dodecyl sulfide, and the balance of 7.22 wt% mainly consisting of catalyst components and dissolved hydrogen sulfide, the tetrapropylene conversion was 85.2%, and the selectivity of t-dodecyl mercaptan was 98.1%.
The application of the catalyst for preparing tert-dodecyl mercaptan in a catalytic manner in the embodiment is mild in reaction conditions.
The fourth concrete implementation mode:
the catalyst for preparing tert-dodecyl mercaptan by catalysis is mainly prepared from anhydrous aluminum chloride, an aromatic hydrocarbon assistant and a chloralkane assistant, wherein the molar ratio of the anhydrous aluminum chloride to the aromatic hydrocarbon assistant to the chloralkane assistant is 1:2: 0.5.
In the catalyst for catalytic preparation of tert-dodecyl mercaptan, the aromatic hydrocarbon auxiliary agent is toluene.
In the catalyst for catalytic preparation of tert-dodecyl mercaptan, the chloroalkane assistant is dichloromethane.
The fifth concrete implementation mode:
a method for preparing a catalyst for the catalytic preparation of tertiary dodecyl mercaptan according to embodiment four, comprising the steps of:
step one, respectively weighing a certain mass of anhydrous aluminum chloride, an aromatic hydrocarbon assistant and a chloralkane assistant according to a molar ratio for later use; step two, rapidly adding weighed anhydrous aluminum chloride into the aromatic hydrocarbon auxiliary agent weighed in the step one while stirring, and uniformly mixing; and step three, dropwise adding the weighed chloralkane assistant under the condition of temperature-controlled stirring for 0.33h, continuing to perform temperature-controlled stirring reaction for 0.33h after dropwise adding is finished, and recovering to room temperature to prepare the acidic liquid catalyst for catalytic preparation of tert-dodecyl mercaptan.
In the preparation method of the catalyst for catalytic preparation of tertiary dodecyl mercaptan, the temperature is controlled at 40 ℃ in the third step, and the stirring speed is 200 r/min.
The catalyst for catalytic preparation of tert-dodecyl mercaptan, which is prepared by the preparation method of the catalyst for catalytic preparation of tert-dodecyl mercaptan according to the embodiment, is an acidic liquid, and the pH value is less than or equal to 5.
The sixth specific implementation mode:
the application of the catalyst for preparing tert-dodecyl mercaptan in a catalytic manner is described in the fourth embodiment, and the catalyst is used for catalyzing the synthesis reaction of triisobutene and hydrogen sulfide.
In the application of the catalyst for catalytic preparation of tert-dodecyl mercaptan, 100g of triisobutene is added into a 250ml four-neck flask, 9g of the prepared catalyst for catalytic preparation of tert-dodecyl mercaptan is added dropwise under stirring, the introduction amount of hydrogen sulfide is controlled to be 30g/h, the temperature of a reaction solution in the four-neck flask is controlled to be 20-25 ℃, the introduction of hydrogen sulfide is stopped after 1h, stirring is continued for 20 minutes, and sampling analysis shows that the conversion rate of triisobutene is 71% and the selectivity of tert-dodecyl mercaptan is 98.5%.
The application of the catalyst for preparing tert-dodecyl mercaptan in a catalytic manner in the embodiment is mild in reaction conditions.
The seventh embodiment:
the catalyst for preparing tert-dodecyl mercaptan in a catalytic manner is mainly prepared from anhydrous aluminum chloride, an aromatic hydrocarbon assistant and a chloralkane assistant, wherein the molar ratio of the anhydrous aluminum chloride to the aromatic hydrocarbon assistant to the chloralkane assistant is 1: 0.5-5: 0.1-1.
The preparation method of the catalyst for preparing tertiary dodecyl mercaptan in a catalytic mode comprises the following steps: step one, respectively weighing a certain mass of anhydrous aluminum chloride, an aromatic hydrocarbon assistant and a chloralkane assistant according to a molar ratio for later use; step two, rapidly adding weighed anhydrous aluminum chloride into the aromatic hydrocarbon auxiliary agent weighed in the step one while stirring, and uniformly mixing; and thirdly, dropwise adding the weighed chloralkane assistant under the condition of temperature-controlled stirring for 0.1-1 h, continuing to perform temperature-controlled stirring reaction for 0.1-1 h after the dropwise adding is finished, and recovering to room temperature to prepare the acidic liquid catalyst for catalytic preparation of tert-dodecyl mercaptan.
The preparation method of the catalyst for catalytic preparation of tertiary dodecyl mercaptan in the embodiment comprises the third step of controlling the stirring temperature at 20-60 ℃ and the stirring speed at 50-500 r/min.
The catalyst for catalytic preparation of tert-dodecyl mercaptan, which is prepared by the preparation method of the catalyst for catalytic preparation of tert-dodecyl mercaptan according to the embodiment, is an acidic liquid, and the pH value is less than or equal to 5.
The specific implementation mode is eight:
the seventh embodiment is different from the seventh embodiment in that: the aromatic hydrocarbon assistant is toluene, and the rest is the same as the seventh embodiment.
The specific implementation method nine:
the seventh and eighth embodiments are different from the specific embodiments in that: the aromatic hydrocarbon auxiliary agent is ethylbenzene, and the rest is the same as the seventh embodiment and the eighth embodiment.
The detailed implementation mode is ten:
the seventh, eighth and ninth embodiments of the present invention are different from the seventh, eighth and ninth embodiments in that: the aromatic hydrocarbon auxiliary agent is dimethylbenzene, and the rest is the same as one of the seventh embodiment, the eighth embodiment and the ninth embodiment.
The concrete implementation mode eleven:
the seventh, eighth, ninth and tenth embodiments are different from the specific embodiments in that: the aromatic hydrocarbon additive is chlorobenzene, and the rest is the same as the formula of one of seven, eight, nine and ten of the specific embodiments.
The specific implementation mode twelve:
the present embodiment differs from the specific embodiments by seven, eight, nine, ten, and eleven: the aromatic hydrocarbon assistant is nitrobenzene, and the others are the same as the seventh, eighth, ninth, tenth and eleventh concrete embodiments.
The specific implementation mode is thirteen:
the seventh, eighth, ninth, tenth, eleventh, and twelfth embodiments of the present invention are different from the first embodiment in that: the chloralkane assistant is monochloromethane, and the others are the same as the embodiments in one of seven, eight, nine, ten, eleven and twelve.
The specific implementation mode is fourteen:
the present embodiment differs from the specific embodiments by seven, eight, nine, ten, eleven, twelve, and thirteen: the chloralkane assistant is dichloromethane, and the rest is the same as the seventh, eighth, ninth, tenth, eleventh, twelfth and thirteenth of the specific embodiment.
The concrete implementation mode is fifteen:
this embodiment differs from the specific embodiments by seven, eight, nine, ten, eleven, twelve, thirteen, and fourteen: the chloralkane assistant is monochloroethane, and the rest is the same as the seventh, eighth, ninth, tenth, eleventh, twelfth, thirteenth and fourteenth embodiment.
The specific implementation mode is sixteen:
this embodiment differs from the embodiment seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen in that: the chloralkane assistant is dichloroethane, and the rest is the same as one of the seven, eight, nine, ten, eleven, twelve, thirteen, fourteen and fifteen of the specific embodiments.
Seventeenth embodiment:
this embodiment differs from the embodiment by seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen: the chloralkane assistant is trichloromethane, and the rest is the same as the seventh, eighth, ninth, tenth, eleventh, twelfth, thirteenth, fourteenth, fifteenth and sixteenth of the specific embodiments.
The specific implementation mode is eighteen:
the use of a catalyst for the catalytic preparation of tertiary dodecyl mercaptan according to any one of embodiments seven to seventeen, wherein the catalyst for the catalytic preparation of tertiary dodecyl mercaptan is used for catalyzing the synthesis reaction of tertiary dodecyl mercaptan, and the reaction selectivity is 95% or more.
The application of the catalyst for catalytic preparation of tert-dodecyl mercaptan in the embodiment is to catalytically synthesize other branched mercaptans such as tert-butyl mercaptan, tert-amyl mercaptan, tert-hexyl mercaptan, tert-heptyl mercaptan, tert-octyl mercaptan, tert-nonyl mercaptan, tert-decyl mercaptan, tert-undecyl mercaptan and the like, and the catalyst also has a good catalytic effect, and the reaction selectivity is over 95%.
The application of the catalyst for preparing tert-dodecyl mercaptan in a catalytic manner in the embodiment is mild in reaction conditions.
The detailed embodiment is nineteen:
according to the seventh to seventeenth embodiments, the catalyst is used for catalyzing the synthesis reaction of tetrapropylene or triisobutene and hydrogen sulfide, and the reaction selectivity is over 98%.
The application of the catalyst for preparing tert-dodecyl mercaptan in a catalytic manner in the embodiment is mild in reaction conditions.
Claims (10)
1. A catalyst for the catalytic preparation of tertiary dodecyl mercaptan, characterized in that: the catalyst for preparing tert-dodecyl mercaptan by catalysis is mainly prepared from anhydrous aluminum chloride, an aromatic hydrocarbon assistant and a chloralkane assistant, wherein the molar ratio of the anhydrous aluminum chloride to the aromatic hydrocarbon assistant to the chloralkane assistant is 1: 0.5-5: 0.1-1.
2. The catalyst for the catalytic preparation of tertiary dodecyl mercaptan according to claim 1, wherein: the aromatic hydrocarbon auxiliary agent is one of benzene, toluene, ethylbenzene, xylene, chlorobenzene and nitrobenzene.
3. The catalyst for the catalytic preparation of tertiary dodecyl mercaptan according to claim 1, wherein: the chloralkane assistant is one of monochloromethane, dichloromethane, trichloromethane, monochloroethane and dichloroethane.
4. A catalyst for the catalytic preparation of tertiary dodecyl mercaptan according to claim 2 or 3, characterized in that: the molar ratio of the anhydrous aluminum chloride to the aromatic hydrocarbon auxiliary agent to the chloralkane auxiliary agent is 1:2: 0.5.
5. A catalyst for the catalytic preparation of tertiary dodecyl mercaptan according to claim 2 or 3, characterized in that: the molar ratio of the anhydrous aluminum chloride to the aromatic hydrocarbon auxiliary agent to the chloralkane auxiliary agent is 1:5: 1.
6. A catalyst for the catalytic preparation of tertiary dodecyl mercaptan according to claim 2 or 3, characterized in that: the molar ratio of the anhydrous aluminum chloride to the aromatic hydrocarbon auxiliary agent to the chloralkane auxiliary agent is 1:0.5: 0.1.
7. A process for the preparation of a catalyst for the catalytic preparation of tert-dodecyl mercaptan as claimed in claims 1 to 6, characterized in that: the method comprises the following steps:
step one, respectively weighing a certain mass of anhydrous aluminum chloride, an aromatic hydrocarbon assistant and a chloralkane assistant according to a molar ratio for later use; step two, rapidly adding weighed anhydrous aluminum chloride into the aromatic hydrocarbon auxiliary agent weighed in the step one while stirring, and uniformly mixing; and thirdly, dropwise adding the weighed chloralkane assistant under the condition of temperature-controlled stirring for 0.1-1 h, continuing to perform temperature-controlled stirring reaction for 0.1-1 h after the dropwise adding is finished, and recovering to room temperature to prepare the acidic liquid catalyst for catalytic preparation of tert-dodecyl mercaptan.
8. The process according to claim 7 for preparing a catalyst for the catalytic preparation of tert-dodecanethiol, characterized in that: in the third step, the temperature is controlled at 20-60 ℃ and the stirring speed is 50-500 r/min.
9. Use of a catalyst according to any one of claims 1 to 8 for the catalytic preparation of tert-dodecyl mercaptan, characterized in that: the catalyst for catalyzing and preparing tert-dodecyl mercaptan is used for catalyzing the synthesis reaction of tert-mercaptan.
10. Use of a catalyst according to claim 9 for the catalytic preparation of tert-dodecyl mercaptan, characterized in that: the catalyst is used for catalyzing the synthetic reaction of tetrapropylene or triisobutene and hydrogen sulfide to prepare tert-dodecyl mercaptan.
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Cited By (1)
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| CN115850132A (en) * | 2022-12-07 | 2023-03-28 | 万华化学集团股份有限公司 | Preparation method of tert-dodecyl mercaptan |
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Application publication date: 20200313 |