CN111690004A - Ionic liquid modified silica gel loaded aluminum chloride catalyst - Google Patents

Ionic liquid modified silica gel loaded aluminum chloride catalyst Download PDF

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Publication number
CN111690004A
CN111690004A CN202010689848.5A CN202010689848A CN111690004A CN 111690004 A CN111690004 A CN 111690004A CN 202010689848 A CN202010689848 A CN 202010689848A CN 111690004 A CN111690004 A CN 111690004A
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ionic liquid
silica gel
modified silica
aluminum chloride
liquid modified
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CN111690004B (en
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李娟�
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Shandong Pharmaceutical Stone Co ltd
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Shandong Zhuojun Industrial Co ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/50—Organo-phosphines
    • C07F9/52—Halophosphines
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0277—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature
    • B01J31/0278—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre
    • B01J31/0281—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre the nitrogen being a ring member
    • B01J31/0284—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre the nitrogen being a ring member of an aromatic ring, e.g. pyridinium
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0277—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature
    • B01J31/0292—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature immobilised on a substrate
    • B01J31/0295—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature immobilised on a substrate by covalent attachment to the substrate, e.g. silica
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
    • B01J2231/42—Catalytic cross-coupling, i.e. connection of previously not connected C-atoms or C- and X-atoms without rearrangement
    • B01J2231/4277—C-X Cross-coupling, e.g. nucleophilic aromatic amination, alkoxylation or analogues

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Catalysts (AREA)

Abstract

The invention provides an ionic liquid modified silica gel loaded aluminum chloride catalyst for preparing phenyl phosphine dichloride through catalysis, which is prepared by the following preparation method: a. mixing and stirring the ionic liquid and the silica gel uniformly, heating to the temperature of 100-150 ℃, keeping the temperature, stirring for 1-2h, cooling to room temperature, and precipitating, filtering and drying the solid to obtain the ionic liquid modified silica gel; b. and (b) adding the ionic liquid modified silica gel obtained in the step (a) into ethanol, adding aluminum chloride while stirring, continuously stirring for 1-2h, removing the ethanol under reduced pressure, heating the mixture to 160 ℃ under the protection of nitrogen, and reacting for 5-10h to obtain yellow powder. The method has the advantages of stable property, high reaction activity, high yield (more than 90%) achieved by using a small amount of catalyst in the process of preparing the phenylphosphonic dichloride, simple post-treatment of the catalyst, capability of removing the catalyst by filtering, and capability of recycling after drying.

Description

Ionic liquid modified silica gel loaded aluminum chloride catalyst
Technical Field
The invention relates to the field of organic synthesis, in particular to a liquid modified silica gel loaded aluminum chloride catalyst and application of the catalyst in preparation of phenyl phosphine dichloride.
Background
Phenylphosphonic Dichloride (DCPP), also known as phenylphosphonic dichloride, is one of the most important monomers for synthesizing aromatic organic phosphine compounds, and is also an intermediate for preparing flame retardants, plasticizers, pesticides, nylon stabilizers, dyes and photoinitiators. Among them, phosphine-based reactive flame retardants prepared from phenylphosphonic dichloride are widely used in the preparation of permanent flame retardant products from polyester resins.
Currently, the synthesis methods of phenyl phosphine dichloride mainly comprise the following steps:
(1) aluminum trichloride catalysis method. The method is characterized in that aluminum trichloride is used as a catalyst, benzene and phosphorus trichloride are used as raw materials and are prepared through a Friedel-crafts reaction, a complex of phenyl phosphine dichloride and aluminum trichloride is obtained firstly, then a decomplexer is needed to replace a product, the method is long in process and complex in process, aluminum trichloride can release a large amount of hydrogen chloride gas after being decomposed in water, and moreover, aluminum trichloride is poor in stability and prone to reacting with water in the air to lose efficacy, and further has strong corrosivity and dangerousness in operation and treatment, the aluminum trichloride is high in exothermic reaction after being decomposed in water, so that the reaction product is complicated, organic matter pollution is caused, an acid solution rich in aluminum is difficult to treat industrially, and the like.
(2) Ionic liquid catalysis. The ionic liquid is one of research hotspots of the Friedel-crafts reaction in recent years, has the advantages of small using amount and no complexing with a target product, can greatly save resources, and is environment-friendly, but has the defects of short service life of the catalyst, volatile effect and low product yield.
(3) Free radical initiation. The method takes simple substance phosphorus and chlorobenzene or phenylphosphine and phosphorus trichloride as raw materials, partial bonds are broken under the high-temperature condition to generate free radicals, and then substitution reaction is carried out among different free radicals to generate the phenylphosphine dichloride. The method has the advantages of simple operation, convenient post-treatment, good product quality, less residue, cyclic utilization of unreacted phosphorus trichloride and chlorobenzene raw materials, and reduction of the production cost of the phenyl phosphine dichloride. However, the reaction needs to be carried out at high temperature and high pressure, and phosphorus trichloride has strong corrosivity and higher requirements on reaction equipment.
Disclosure of Invention
Based on the problem, the invention provides a method for preparing phenyl phosphine dichloride by taking ionic liquid modified silica gel loaded aluminum chloride as a catalyst, the method does not need a decomplexation catalyst, the dosage of the catalyst is small, the reaction is mild, the process is simple, and the yield of the product is high.
The invention is realized by the following technical scheme:
a method for preparing phenyl phosphine dichloride comprises the step of carrying out catalytic reaction by taking benzene and phosphorus trichloride as raw materials and taking ionic liquid modified silica gel loaded aluminum chloride as a catalyst.
The ionic liquid modified silica gel loaded aluminum chloride catalyst is prepared by the following preparation method: a. mixing and stirring the ionic liquid and the silica gel uniformly, heating to the temperature of 100-150 ℃, keeping the temperature, stirring for 1-2h, cooling to room temperature, and precipitating, filtering and drying the solid to obtain the ionic liquid modified silica gel;
b. and (b) adding the ionic liquid modified silica gel obtained in the step (a) into ethanol, adding aluminum chloride while stirring, continuously stirring for 1-2h, removing the ethanol under reduced pressure, heating the mixture to 160 ℃ under the protection of nitrogen, and reacting for 5-10h to obtain yellow powder, namely the ionic liquid modified silica gel loaded aluminum chloride catalyst.
Preferably, the ionic liquid is imidazole ionic liquid.
Further preferably, the ionic liquid is selected from 1-ethyl-3-methylimidazolium tetrafluoroborate, 1-butyl-3-methylimidazolium bromide, 1-butyl-3-methylimidazolium chloride or 1-ethyl-3-methylimidazolium trifluoroacetate.
The silica gel is selected from 300-400 mesh silica gel.
The mass ratio of the silica gel to the ionic liquid is 1: 5-10.
Preferably, 5-10mL of ethanol, 0.1-1g of aluminum chloride is used per g of ionic liquid-modified silica gel.
Preferably, the method further comprises the steps of placing benzene and phosphorus trichloride in a reaction container, stirring uniformly, adding an ionic liquid modified silica gel loaded aluminum chloride catalyst, heating to reflux, keeping for 0.5-2h, filtering to remove the catalyst after the reaction is finished, and rectifying the crude product under reduced pressure to obtain the product.
Preferably, the molar ratio of the benzene to the phosphorus trichloride is 1: 1-2.
Preferably, the feeding ratio of the benzene to the catalyst is 10-1: 1 mol/g.
The invention also provides an ionic liquid modified silica gel loaded aluminum chloride catalyst.
The invention also provides a preparation method of the ionic liquid modified silica gel loaded aluminum chloride catalyst.
Compared with the prior art, the invention has the advantages that: the ionic liquid modified silica gel loaded aluminum chloride catalyst is simple to prepare, the obtained catalyst has the catalytic properties of both the ionic liquid and the aluminum chloride, the property is stable, the reaction activity is high, and the product can reach high yield by using a small amount of catalyst in the process of preparing the phenyl phosphine dichloride. In addition, the post-treatment of the catalyst is simple, the catalyst can be removed only by filtering, and the catalyst can still be recycled after being dried.
Detailed Description
In order to make the objects, technical solutions and advantages of the embodiments of the present disclosure more apparent, the technical solutions of the embodiments of the present disclosure are clearly and completely described. It is to be understood that the described embodiments are only a few embodiments of the present disclosure, and not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the described embodiments of the disclosure without any inventive step, are within the scope of protection of the disclosure.
Unless otherwise defined, technical or scientific terms used herein shall have the ordinary meaning as understood by one of ordinary skill in the art to which this disclosure belongs.
Example 1
a. Mixing 25g of 1-ethyl-3-methylimidazole tetrafluoroborate and 5g of 400-mesh silica gel, uniformly stirring, heating to 120 ℃, keeping the temperature, stirring for 2 hours, cooling to room temperature, and precipitating, filtering and drying the solid to obtain ionic liquid modified silica gel;
b. adding 3g of ionic liquid modified silica gel into 15ml of ethanol, adding 0.5g of aluminum chloride under stirring, continuously stirring for 2h, removing the ethanol under reduced pressure, heating the mixture to 120 ℃ under the protection of nitrogen, and reacting for 10h to obtain yellow powder, namely the ionic liquid modified silica gel loaded aluminum chloride catalyst.
Example 2
a. Mixing 30g of 1-butyl-3-methylimidazole tetrafluoroborate and 3g of 300-mesh 400-mesh silica gel, uniformly stirring, heating to 150 ℃, keeping the temperature, stirring for 1 hour, cooling to room temperature, and precipitating, filtering and drying the solid to obtain ionic liquid modified silica gel;
b. adding 2g of ionic liquid modified silica gel into 20ml of ethanol, adding 2g of aluminum chloride under stirring, continuously stirring for 2h, removing the ethanol under reduced pressure, heating the mixture to 160 ℃ under the protection of nitrogen, and reacting for 5h to obtain yellow powder, namely the ionic liquid modified silica gel loaded aluminum chloride catalyst.
Example 3
a. Mixing 30g of 1-butyl-3-methylimidazolium bromide and 5g of 300-mesh 400-mesh silica gel, uniformly stirring, heating to 150 ℃, keeping the temperature, stirring for 1 hour, cooling to room temperature, and precipitating, filtering and drying the solid to obtain ionic liquid modified silica gel;
b. adding 2g of ionic liquid modified silica gel into 18ml of ethanol, adding 1.5g of aluminum chloride under stirring, continuously stirring for 1h, removing the ethanol under reduced pressure, heating the mixture to 150 ℃ under the protection of nitrogen, and reacting for 5h to obtain yellow powder, namely the ionic liquid modified silica gel loaded aluminum chloride catalyst.
Example 4
Placing 1mol of benzene and 1mol of phosphorus trichloride in a reaction container, stirring uniformly, adding 1g of the ionic liquid modified silica gel loaded aluminum chloride catalyst prepared in the embodiment 1, heating to reflux, keeping for 0.5h, filtering to remove the catalyst after the reaction is finished, and rectifying the crude product under reduced pressure to obtain the product with the yield of 90% (calculated on benzene).
Example 5
Placing 1mol of benzene and 2mol of phosphorus trichloride in a reaction container, stirring uniformly, adding 0.5g of the ionic liquid modified silica gel loaded aluminum chloride catalyst prepared in the embodiment 2, heating to reflux, keeping for 2 hours, filtering to remove the catalyst after the reaction is finished, and rectifying the crude product under reduced pressure to obtain the product, wherein the yield is 91.5% (calculated by benzene).
Example 6
Placing 1mol of benzene and 1.5mol of phosphorus trichloride in a reaction container, stirring uniformly, adding 1g of the ionic liquid modified silica gel loaded aluminum chloride catalyst prepared in the embodiment 3, heating to reflux, keeping for 2h, filtering to remove the catalyst after the reaction is finished, and rectifying the crude product under reduced pressure to obtain the product, wherein the yield is 93.6% (calculated by benzene).
Example 7
Placing 1mol of benzene and 1mol of phosphorus trichloride in a reaction container, stirring uniformly, adding 0.1g of the ionic liquid modified silica gel loaded aluminum chloride catalyst prepared in the embodiment 1, heating to reflux, keeping for 2 hours, filtering to remove the catalyst after the reaction is finished, and rectifying the crude product under reduced pressure to obtain the product, wherein the yield is 92.1% (calculated by benzene).
Example 8
Placing 1mol of benzene and 1mol of phosphorus trichloride in a reaction container, stirring uniformly, adding 0.1g of the ionic liquid modified silica gel loaded aluminum chloride catalyst prepared in the embodiment 2, heating to reflux, keeping for 2 hours, filtering to remove the catalyst after the reaction is finished, and rectifying the crude product under reduced pressure to obtain the product, wherein the yield is 90.8% (calculated by benzene).
Example 9
Placing 1mol of benzene and 1mol of phosphorus trichloride in a reaction container, stirring uniformly, adding 0.1g of the ionic liquid modified silica gel loaded aluminum chloride catalyst prepared in the embodiment 3, heating to reflux, keeping for 2 hours, filtering to remove the catalyst after the reaction is finished, and rectifying the crude product under reduced pressure to obtain the product, wherein the yield is 91.1% (calculated by benzene).
Example 10
The catalyst of example 9 was filtered off, washed repeatedly with distilled water, dried in a drying oven to give the catalyst, which was substituted for the catalyst of example 9, and the procedure of example 9 was repeated to give a final product yield of 90.3% (based on benzene).
Finally, it should be noted that: it should be understood that the above examples are only for clearly illustrating the present invention and are not intended to limit the embodiments. Other variations and modifications will be apparent to persons skilled in the art in light of the above description. And are neither required nor exhaustive of all embodiments. And obvious variations or modifications of the invention may be made without departing from the scope of the invention.

Claims (10)

1. An ionic liquid modified silica gel loaded aluminum chloride catalyst for preparing phenyl phosphine dichloride through catalysis is characterized in that the catalyst is prepared by the following preparation method: a. mixing and stirring the ionic liquid and the silica gel uniformly, heating to the temperature of 100-150 ℃, keeping the temperature, stirring for 1-2h, cooling to room temperature, and precipitating, filtering and drying the solid to obtain the ionic liquid modified silica gel;
b. and (b) adding the ionic liquid modified silica gel obtained in the step (a) into ethanol, adding aluminum chloride while stirring, continuously stirring for 1-2h, removing the ethanol under reduced pressure, heating the mixture to 160 ℃ under the protection of nitrogen, and reacting for 5-10h to obtain yellow powder, namely the ionic liquid modified silica gel loaded aluminum chloride catalyst.
2. The ionic liquid modified silica gel loaded aluminum chloride catalyst for preparing the phenylphosphonic dichloride through catalysis according to claim 1, wherein the ionic liquid is imidazole ionic liquid.
3. An ionic liquid modified silica gel supported aluminum chloride catalyst for the catalytic production of phenylphosphonic dichloride according to claim 1 or 2, wherein the ionic liquid is selected from 1-ethyl-3-methylimidazolium tetrafluoroborate, 1-butyl-3-methylimidazolium bromide, 1-butyl-3-methylimidazolium chloride or 1-ethyl-3-methylimidazolium trifluoroacetate.
4. The ionic liquid modified silica gel supported aluminum chloride catalyst for the catalytic preparation of phenylphosphine dichloride according to claim 1 or 2, wherein the silica gel is selected from 300-400 mesh silica gel.
5. The ionic liquid modified silica gel supported aluminum chloride catalyst for catalytically preparing the phenyl phosphine dichloride according to claim 1 or 2, wherein the mass ratio of the silica gel to the ionic liquid is 1: 5-10.
6. The ionic liquid modified silica gel supported aluminum chloride catalyst for the catalytic preparation of phenylphosphine dichloride according to claim 1 or 2, using 5-10mL of ethanol, 0.1-1g of aluminum chloride per g of ionic liquid modified silica gel.
7. Use of an ionic liquid modified silica gel supported aluminum chloride catalyst as claimed in any one of claims 1 to 6 in the preparation of phenylphosphine dichloride.
8. The application of the ionic liquid modified silica gel loaded aluminum chloride catalyst in the preparation of the phenyl phosphine dichloride according to claim 7 comprises the steps of placing benzene and phosphorus trichloride in a reaction container, stirring uniformly, adding the ionic liquid modified silica gel loaded aluminum chloride catalyst, heating to reflux, keeping for 0.5-2h, filtering to remove the catalyst after the reaction is finished, and rectifying a crude product under reduced pressure to obtain a product.
9. The use of the ionic liquid modified silica gel supported aluminum chloride catalyst according to claim 8 in the preparation of phenyl phosphine dichloride, wherein the molar ratio of benzene to phosphorus trichloride is 1: 1-2.
10. The use of the ionic liquid modified silica gel supported aluminum chloride catalyst according to claim 8 in the preparation of phenyl phosphine dichloride, wherein the feeding ratio of benzene to the catalyst is 10-1: 1 mol/g.
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Cited By (1)

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