1, 1-bis (4-hydroxybenzene)-tetrahydronaphthalene as well as preparation method and application thereof
By melting the 1-tetrahydronaphthalone and phenol under inert gas atmosphere and catalyst conditions, the problems of harsh reaction conditions and poor selectivity in the prior art were solved, and the efficient synthesis of 1,1-bis(4-hydroxybenzene)-tetrahydronaphthalene was achieved, which improved the purity and yield of the product, and broadened the application range of polyaryletherketone materials.
Patent Information
- Application Number
- CN202510669874.4
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Filing Date
- 2025-05-23
- Publication Date
- 2025-09-05
AI Technical Summary
The current synthesis research of 1,1-bis(4-hydroxybenzene)-tetrahydronaphthalene is in its infancy, with harsh reaction conditions, low catalyst efficiency and complex side reactions, which seriously restrict the industrial production and large-scale application of PAEK materials containing tetrahydronaphthalene structure.
Under the inert gas atmosphere and catalyst conditions, 1-tetrahydronaphthalone and phenol were melted, and methanesulfonic acid-mercaptopropionic acid was used as the catalyst to control the reaction temperature and time, and achieve high selective synthesis and simple separation and purification of the product.
The efficient preparation of 1,1-bis(4-hydroxybenzene)-tetrahydronaphthalene was achieved, with a synthesis yield of more than 85% and a purity of more than 88%. The product can participate in the polymerization reaction as a key monomer, broadening the molecular design space of polyaryletherketone materials.
Smart Images
Figure CN120590247A_ABST
Abstract
Description
Technical Field
[0001] The present application belongs to the technical field of organic synthesis, and in particular relates to 1,1-bis(4-hydroxybenzene)-tetralin and its preparation method and application. Background Art
[0002] Polyaryletherketone (PAEK), a high-performance engineering thermoplastic, holds a key position in aerospace, defense, and electronic information manufacturing due to its exceptional mechanical strength, chemical stability, and radiation resistance. Its unique molecular chain structure maintains stable physical and chemical properties even at high temperatures, making it an ideal choice for manufacturing critical components under extreme conditions.
[0003] 1,1-Bis(4-hydroxyphenyl)tetralin, a typical organic compound containing a rigid tetralin structural unit, plays a key role in the molecular design of PAEK. Its introduction into the PAEK backbone effectively restricts the free rotation of the molecular chain through the rigid skeleton of the tetralin group, significantly increasing the material's glass transition temperature and heat deformation temperature. This demonstrates irreplaceable technical advantages in electronic devices used in extreme high-temperature environments.
[0004] However, research on the synthesis of 1,1-bis(4-hydroxyphenyl)tetralin is still in its infancy. Public literature only sporadically explores some synthetic pathways, and existing processes often suffer from harsh reaction conditions, low catalyst efficiency, and complex side reactions, severely hindering the industrial production and large-scale application of PAEK materials containing tetralin. Therefore, developing a green synthesis process that combines high atom economy, mild reaction conditions, and high selectivity to achieve the efficient preparation of 1,1-bis(4-hydroxyphenyl)tetralin has become a bottleneck in improving the performance of PAEK materials. Summary of the Invention
[0005] The present application discloses 1,1-bis(4-hydroxybenzene)-tetralin and its preparation method and application, aiming to solve the technical problems of the existing 1,1-bis(4-hydroxybenzene)-tetralin preparation process, such as harsh reaction conditions, low yield and poor selectivity.
[0006] In order to achieve the above objectives, the technical solution of this application is:
[0007] The first aspect of the present application provides a method for preparing 1,1-bis(4-hydroxybenzene)-tetralin, the method comprising:
[0008] Under inert gas atmosphere and catalyst conditions, 1-tetralone and phenol are melted and reacted, and then separated and purified to obtain the 1,1-bis(4-hydroxybenzene)-tetralin.
[0009] In combination with the first aspect, preferably, the molar ratio of 1-tetralone to phenol is 1:(2.5-10).
[0010] In combination with the first aspect, preferably, the molar ratio of 1-tetralone to phenol is 1:4.
[0011] In combination with the first aspect, preferably, the catalyst is a methanesulfonic acid-mercaptopropionic acid composite acid.
[0012] In combination with the first aspect, preferably, the added amount of the catalyst is 0.05-0.5 of the molar equivalent of 1-tetralone.
[0013] In combination with the first aspect, preferably, the added amount of methanesulfonic acid is 10-50 times the molar equivalent of mercaptopropionic acid.
[0014] In combination with the first aspect, preferably, when the melt reaction is carried out, the reaction temperature is 45-65° C. and the reaction time is 6-24 h.
[0015] The second aspect of the present application provides 1,1-bis(4-hydroxybenzene)-tetralin prepared by the preparation method of the first aspect, which has the chemical structure shown in Formula I:
[0016]
[0017] The third aspect of the present application provides the use of polyaryletherketone prepared from 1,1-bis(4-hydroxybenzene)-tetralin as described in the second aspect in an integrated circuit board.
[0018] Compared with the prior art, the advantages or beneficial effects of the embodiments of the present application include at least:
[0019] The preparation process provided in the present application is prepared by melt reaction of 1-tetralone and phenol under inert gas atmosphere and catalyst conditions. On the one hand, the homogeneous characteristics of the melt reaction system are utilized to allow the reactants to fully contact and undergo directional condensation, and the product can be purified by simple separation and purification, which greatly reduces the difficulty of product synthesis and purification. The synthesis yield can reach more than 85% and the purity can reach more than 88%; on the other hand, the catalyst system used in the process is highly selective and can accurately control the reaction path, effectively inhibit the occurrence of side reactions, and reduce the generation of by-products, which not only improves the atomic utilization rate but also ensures the high purity of the product; thirdly, the large-scale preparation of 1,1-bis(4-hydroxybenzene)-tetralin is successfully achieved for the first time. The high-purity compound obtained by this process can be used as a key monomer to participate in polymerization reactions, broadening the molecular design space of high-performance polyaryletherketone materials. BRIEF DESCRIPTION OF THE DRAWINGS
[0020] To more clearly illustrate the technical solutions of the embodiments of this application, the following briefly introduces the drawings required for describing the embodiments. Obviously, the drawings described below are only some of the embodiments described in this application. For those skilled in the art, other drawings can be derived from these drawings without inventive effort.
[0021] Figure 1 This is the NMR spectrum of 1,1-bis(4-hydroxybenzene)-tetralin prepared in the examples of this application. DETAILED DESCRIPTION
[0022] The following will be combined with the accompanying drawings in the embodiments of this application to clearly and completely describe the technical solutions in the embodiments of this application. Obviously, the described embodiments are part of the embodiments of this application, not all of the embodiments. Based on the embodiments in this application, all other embodiments obtained by ordinary technicians in this field without making creative efforts are within the scope of protection of this application.
[0023] In the following description of this embodiment, the term "and / or" is used to describe the association relationship between associated objects, indicating that three relationships can exist. For example, A and / or B can represent: A exists alone, B exists alone, and A and B exist at the same time. A and B can be singular or plural.
[0024] In the following description of this embodiment, the term "at least one" refers to one or more, and "plurality" refers to two or more. "At least one of the following" or similar expressions refers to any combination of these items, including any combination of single items or plural items. For example, "at least one of a, b, or c", or "at least one of a, b, and c" can all represent: a, b, c, ab (i.e., a and b), ac, bc, or abc, where a, b, and c can be single or multiple.
[0025] Those skilled in the art should understand that in the following description of the embodiments of the present application, the order of serial numbers does not mean the order of execution, some or all of the steps can be executed in parallel or sequentially, and the execution order of each process should be determined by its function and internal logic, and should not constitute any limitation on the implementation process of the embodiments of the present application.
[0026] The terms used in the embodiments of the present application are only for the purpose of describing specific embodiments and are not intended to limit the present application. The singular forms "a", "an" and "the" used in the embodiments of the present application and the appended claims are also intended to include plural forms unless the context clearly indicates otherwise.
[0027] It should be noted that all raw materials and reagents in the examples of the present application were purchased on the market or prepared according to conventional methods well known to those skilled in the art.
[0028] In a first aspect, an embodiment of the present application provides a method for preparing 1,1-bis(4-hydroxybenzene)-tetralin, the preparation method comprising:
[0029] Under inert gas atmosphere and catalyst conditions, 1-tetralone and phenol are melted and reacted, and then separated and purified to obtain the 1,1-bis(4-hydroxybenzene)-tetralin.
[0030] Among them, on the one hand, the homogeneous characteristics of the molten reaction system are utilized to ensure that the reactants are fully contacted and directional condensation occurs. The product purification can be achieved only through simple separation and purification, which greatly reduces the difficulty of product synthesis and purification, and the synthesis yield can reach more than 85%; on the other hand, the catalyst system used in the process is highly selective and can accurately control the reaction path, effectively inhibit the occurrence of side reactions, and reduce the generation of by-products, which not only improves the atomic utilization rate but also ensures the high purity of the product; thirdly, the large-scale preparation of 1,1-bis(4-hydroxybenzene)-tetralin was successfully achieved for the first time. The high-purity compound obtained by this process can be used as a key monomer to participate in polymerization reactions, greatly broadening the molecular design space of high-performance polyaryletherketone materials.
[0031] It should be noted that the reaction equation 1 of 1,1-bis(4-hydroxybenzene)-tetralin prepared in this application is as follows:
[0032]
[0033] Reaction equation 1
[0034] In the examples of the present application, the molar ratio of 1-tetralone to phenol is preferably 1:(2.5-10), more preferably 1:4.5. By controlling the molar ratio of 1-tetralone to phenol, while ensuring product quality and yield, the raw materials are utilized to the maximum extent, the waste of raw materials and the generation of by-products are reduced, thereby improving the selectivity and yield of the target product.
[0035] In the embodiment of the present application, the catalyst is preferably a methanesulfonic acid-mercaptopropionic acid composite acid, wherein methanesulfonic acid has strong acidity and is relatively mild, has low corrosiveness, good thermal stability, is environmentally friendly, and has low toxicity; mercaptopropionic acid has mild stability and reducibility, and its catalytic effect is relatively efficient. By controlling the selection of this composite acid, the reaction can be better catalyzed.
[0036] In the embodiments of the present application, the amount of the catalyst added is preferably 0.05-0.5 of the molar equivalent of 1-tetralone, and the amount of methanesulfonic acid added is preferably 10-50 times the molar equivalent of mercaptopropionic acid. By controlling the amount of catalyst added, the reaction can be carried out under relatively mild conditions such as temperature and pressure, which reduces the requirements for reaction equipment and is also conducive to the rational use of energy and cost savings. It can also reduce the activation energy of the reaction, thereby accelerating the reaction rate. Adding a catalyst can enable the reaction to achieve a higher conversion rate in a shorter period of time, thereby improving production efficiency. If the amount of catalyst added is too little, the reaction rate may be too slow, resulting in an extension of the production cycle; and if the amount added is too much, the reaction rate may be too fast, difficult to control, and may even trigger side reactions.
[0037] In the examples of the present application, when performing the melt reaction, the reaction temperature is preferably 45-65°C, more preferably 50°C, and the reaction time is preferably 6-24 hours, more preferably 8 hours. Controlling the reaction conditions can increase the reaction rate, shorten the reaction time, and thus improve production efficiency. It can also suppress the occurrence of side reactions and improve the purity of the product.
[0038] In a second aspect, the present invention also provides 1,1-bis(4-hydroxybenzene)-tetralin prepared by the preparation method described in the first aspect, which has the chemical structure shown in Formula I:
[0039]
[0040] It should be noted that the 1,1-bis(4-hydroxybenzene)-tetralin prepared in the present application can increase the rigidity of the polyaryletherketone molecular chain and restrict the movement of the molecular chain when used in the preparation of polyaryletherketone molecules, thereby improving the heat resistance of the polyaryletherketone, enabling the material to maintain stable performance at higher temperatures and expand its application range in high-temperature environments; it also helps to improve the mechanical properties of the polyaryletherketone, increase the strength and modulus of the material, and make it more suitable for use in situations where it can withstand greater external forces.
[0041] In a third aspect, embodiments of the present application further provide the use of polyaryletherketones prepared from 1,1-bis(4-hydroxyphenyl)tetralin as described in the second aspect in integrated circuit boards. The 1,1-bis(4-hydroxyphenyl)tetralin prepared above can impart excellent heat resistance and mechanical properties to the polyaryletherketones, and thus has broad application prospects in integrated circuit boards subjected to extremely high temperature environments.
[0042] The technical solution of the present application will be further described below in conjunction with specific embodiments.
[0043] Example 1
[0044] This embodiment provides a method for preparing A1-1,1-bis(4-hydroxybenzene)-tetralin, which specifically comprises:
[0045] To a 500 mL four-necked reaction flask, add 29.24 g (0.2 mole) of 1-tetralone, 56.47 g (0.6 mole) of phenol, 0.96 g (0.01 mole) of methanesulfonic acid, and 0.106 g (0.001 mole) of mercaptopropionic acid. After heating to 50°C and reacting for 12 hours, HPLC was used to confirm that the residual 1-tetralone was less than 1%. After completion of the reaction, the reaction system was subjected to reduced pressure distillation at 80°C to recover unreacted phenol. The resulting viscous solid was washed several times with 50°C hot water and then recrystallized from 5 parts ethanol to obtain A1-1,1-bis(4-hydroxyphenyl)-tetralin.
[0046] A1-1,1-bis(4-hydroxybenzene)-tetralin prepared in Example 1 of the present application is a white solid with a product purity (HPLC) of 93.6% and a yield of 85.2%.
[0047] Example 2
[0048] This embodiment provides a method for preparing A2-1,1-bis(4-hydroxybenzene)-tetralin, which specifically comprises:
[0049] To a 500 mL four-necked reaction flask, add 29.24 g (0.2 mole) of 1-tetralone, 75.29 g (0.8 mole) of phenol, 1.92 g (0.02 mole) of methanesulfonic acid, and 0.106 g (0.001 mole) of mercaptopropionic acid. After heating to 50°C and reacting for 8 hours, HPLC was used to confirm that the residual 1-tetralone was less than 1%. After the reaction was completed, the reaction system was subjected to reduced pressure distillation at 80°C to recover unreacted phenol. The resulting viscous solid was washed several times with 50°C hot water and then recrystallized from 5 parts ethanol to obtain A2-1,1-bis(4-hydroxyphenyl)-tetralin.
[0050] A2-1,1-bis(4-hydroxybenzene)-tetralin prepared in Example 2 of the present application is a white solid with a product purity (HPLC) of 98.2% and a yield of 90.3%.
[0051] In order to verify the structural properties of the prepared A2-1,1-bis(4-hydroxybenzene)-tetralin, nuclear magnetic resonance testing was performed on it.
[0052] according to Figure 1 Shown is the nuclear magnetic spectrum of A2-1,1-bis(4-hydroxybenzene)-tetralin, 1H-NMR (CDCl3) δ: 1.72 (2H, m, -CH2-), 2.18 (2H, t, -CH2-), 2.70 (2H, t, Ar-CH2), 6.67 (4H, d, ArH), 6.92-7.01 (8H, d, ArH), 9.06 (2H, s, -OH).
[0053] Example 3
[0054] This embodiment provides a method for preparing A3-1,1-bis(4-hydroxybenzene)-tetralin, which specifically comprises:
[0055] To a 500 mL four-necked reaction flask, add 29.24 g (0.2 mole) of 1-tetralone, 122.34 g (1.3 mole) of phenol, 2.88 g (0.03 mole) of methanesulfonic acid, and 0.106 g (0.001 mole) of mercaptopropionic acid. The mixture was heated to 55°C and reacted for 12 hours. HPLC confirmed that the residual 1-tetralone was less than 1%. After the reaction, the reaction system was subjected to reduced pressure distillation at 80°C to recover unreacted phenol. The resulting viscous solid was washed several times with 50°C hot water and then recrystallized from 5 parts ethanol to obtain A3-1,1-bis(4-hydroxyphenyl)tetralin.
[0056] A3-1,1-bis(4-hydroxybenzene)-tetralin prepared in Example 3 of the present application is a white solid, the product purity (HPLC) is 93.6%, and the yield is 87.3%.
[0057] Example 4
[0058] This embodiment provides a method for preparing A4-1,1-bis(4-hydroxybenzene)-tetralin, which specifically comprises:
[0059] To a 500 mL four-necked reaction flask, add 29.20 g (0.2 mole) of 1-tetralone, 75.29 g (0.8 mole) of phenol, 0.96 g (0.01 mole) of methanesulfonic acid, and 0.106 g (0.001 mole) of mercaptopropionic acid. The mixture was heated to 55°C and reacted for 12 hours. HPLC confirmed that the residual 1-tetralone was less than 1%. After the reaction, the reaction system was subjected to reduced pressure distillation at 80°C to recover unreacted phenol. The resulting viscous solid was washed several times with 50°C hot water and then recrystallized from 5 parts ethanol to obtain A4-1,1-bis(4-hydroxyphenyl)tetralin.
[0060] A4-1,1-bis(4-hydroxybenzene)-tetralin prepared in Example 4 of the present application is a white solid with a product purity (HPLC) of 88.7% and a yield of 79.8%.
[0061] Example 5
[0062] This embodiment provides a method for preparing A5-1,1-bis(4-hydroxybenzene)-tetralin, which specifically comprises:
[0063] To a 500 mL four-necked reaction flask, add 29.20 g (0.2 mole) of 1-tetralone, 188.22 g (2 moles) of phenol, 4.80 g (0.05 mole) of methanesulfonic acid, and 0.106 g (0.001 mole) of mercaptopropionic acid. The mixture was heated to 55°C and reacted for 12 hours. HPLC confirmed that the residual 1-tetralone was less than 1%. After the reaction, the reaction system was subjected to reduced pressure distillation at 80°C to recover unreacted phenol. The resulting viscous solid was washed several times with 50°C hot water and then recrystallized from 5 parts ethanol to obtain A5-1,1-bis(4-hydroxyphenyl)tetralin.
[0064] A5-1,1-bis(4-hydroxybenzene)-tetralin prepared in Example 5 of the present application is a white solid with a product purity (HPLC) of 91.5% and a yield of 86.1%.
[0065] At the same time, in order to verify the comprehensive performance of 1,1-bis(4-hydroxybenzene)-tetralin prepared in the above examples, the present application provides the following comparative examples for detailed description.
[0066] Comparative Example 1
[0067] This comparative example provides a preparation method of B1-1,1-bis(4-hydroxybenzene)-tetralin, which specifically comprises:
[0068] In a 500 mL four-necked reaction flask, add 29.20 g (0.2 mole) of 1-tetralone, 75.29 g (0.8 mole) of phenol, and 5 g (0.05 mole) of 98% sulfuric acid. After heating to 55°C and reacting for 12 hours, HPLC confirmed that the residual 1-tetralone was less than 1%. After the reaction, the reaction system was subjected to vacuum distillation at 80°C to recover unreacted phenol. The resulting viscous solid was washed several times with 60°C hot water and then recrystallized from 5 parts ethanol to obtain B1-1,1-bis(4-hydroxyphenyl)tetralin.
[0069] The B1-1,1-bis(4-hydroxybenzene)-tetralin prepared in Comparative Example 1 of the present application is a white solid with a product purity (HPLC) of 88.6% and a yield of 70.3%.
[0070] Comparative Example 2
[0071] This comparative example provides a method for preparing B2-1,1-bis(4-hydroxybenzene)-tetralin, which specifically comprises:
[0072] To a 500 mL four-necked reaction flask, add 29.20 g (0.2 mole) of 1-tetralone, 75.29 g (0.8 mole) of phenol, 5 g (0.05 mole) of 98% sulfuric acid, and 0.106 g (0.001 mole) of mercaptopropionic acid. After heating to 55°C and reacting for 12 hours, HPLC confirmed that the residual 1-tetralone was less than 1%. After completion of the reaction, the reaction system was subjected to vacuum distillation at 80°C to recover unreacted phenol. The resulting viscous solid was washed several times with 60°C hot water and then recrystallized from 5 parts ethanol to obtain B2-1,1-bis(4-hydroxyphenyl)tetralin.
[0073] B2-1,1-bis(4-hydroxybenzene)-tetralin prepared in Comparative Example 2 of the present application is a white solid with a product purity (HPLC) of 88.3% and a yield of 75.6%.
[0074] Comparative Example 3
[0075] This comparative example provides a preparation method of B3-1,1-bis(4-hydroxybenzene)-tetralin, which specifically comprises:
[0076] To a 500 mL four-necked reaction flask, add 29.20 g (0.2 mole) of 1-tetralone, 75.29 g (0.8 mole) of phenol, 4.8 g (0.05 mole) of methanesulfonic acid, and 0.159 g (0.0015 mole) of mercaptopropionic acid. After heating to 55°C and reacting for 12 hours, HPLC confirmed that the residual 1-tetralone was less than 1%. After completion of the reaction, the reaction system was subjected to vacuum distillation at 80°C to recover unreacted phenol. The resulting viscous solid was washed several times with 60°C hot water and then recrystallized from 5 parts ethanol to obtain B3-1,1-bis(4-hydroxyphenyl)tetralin.
[0077] B3-1,1-bis(4-hydroxybenzene)-tetralin prepared in Comparative Example 3 of the present application is a white solid with a product purity (HPLC) of 88.6% and a yield of 68.5%.
[0078] Comparative Example 4
[0079] This comparative example provides a method for preparing B4-1,1-bis(4-hydroxybenzene)-tetralin, which specifically comprises:
[0080] To a 500 mL four-necked reaction flask, add 29.20 g (0.2 mole) of 1-tetralone, 150.57 g (1.6 mole) of phenol, 0.96 g (0.01 mole) of methanesulfonic acid, and 0.742 g (0.007 mole) of mercaptopropionic acid. After heating to 55°C and reacting for 12 hours, HPLC confirmed that the residual 1-tetralone was less than 1%. After completion of the reaction, the reaction system was subjected to vacuum distillation at 80°C to recover unreacted phenol. The resulting viscous solid was washed several times with 60°C hot water and then recrystallized from 5 parts ethanol to obtain B4-1,1-bis(4-hydroxyphenyl)tetralin.
[0081] The B4-1,1-bis(4-hydroxybenzene)-tetralin prepared in Comparative Example 4 of the present application is a white solid with a product purity (HPLC) of 91.5% and a yield of 80.6%.
[0082] The purity and yield data of 1,1-bis(4-hydroxybenzene)-tetralin prepared in Examples 1-5 and Comparative Examples 1-4 of the present application are shown in Table 1.
[0083] Table 1 Purity and yield data of Examples and Comparative Examples
[0084] Serial number purity Yield Example 1 93.6 85.2 Example 2 98.2 90.3 Example 3 93.6 87.3 Example 4 88.7 79.8 Example 5 91.5 86.1 Comparative Example 1 88.6 70.3 Comparative Example 2 88.3 75.6 Comparative Example 3 88.6 68.5 Comparative Example 4 91.5 80.6
[0085] As can be seen from the data in Table 1, the preparation method of the present application does not require a complex purification process, and the target product 1,1-bis(4-hydroxyphenyl)tetralin has a high purity and yield, with a purity of >88.7% and a yield of 79.8-90.3%. However, the difference between Comparative Example 1 and Example 2 is that only sulfuric acid is used as a catalyst, which significantly reduces the purity and yield; the difference between Comparative Example 2 and Example 2 is that sulfuric acid and mercaptopropionic acid composite acid are used as catalysts, which significantly reduces the purity and yield; the difference between Comparative Example 3 and Example 2 is that sulfuric acid and mercaptopropionic acid composite acid are used as catalysts, which significantly reduces the purity and yield; and the difference between Comparative Example 4 and Example 2 is that sulfuric acid and mercaptopropionic acid composite acid are used as catalysts, which significantly reduces the purity and yield.
[0086] Therefore, the preparation process provided in the present application is prepared by melt-reacting 1-tetralone and phenol under inert gas atmosphere and catalyst conditions. The homogeneous characteristics of the melt reaction system are utilized to allow the reactants to fully contact and undergo directional condensation. The product can be purified by simple separation and purification, which greatly reduces the difficulty of product synthesis and purification. The synthesis yield can reach more than 85% and the purity can reach more than 88%. This is the first successful large-scale preparation of 1,1-bis(4-hydroxybenzene)-tetralin. The high-purity compound obtained by this process can be used as a key monomer to participate in polymerization reactions, greatly broadening the molecular design space of high-performance polyaryletherketone materials and having broad application prospects in integrated circuit boards.
[0087] The various embodiments in this specification are described in a progressive manner. The same or similar parts between the various embodiments can be referenced to each other, and each embodiment focuses on the differences from other embodiments.
[0088] The above embodiments are only used to illustrate the technical solutions of the present application, rather than to limit the present application. Although the present application has been described in detail with reference to the aforementioned embodiments, a person skilled in the art should understand that the technical solutions described in the aforementioned embodiments can still be modified, or some or all of the technical features therein can be replaced by equivalents. However, these modifications or replacements do not cause the essence of the corresponding technical solutions to deviate from the scope of the technical solutions of the present application.
Claims
1. A method for preparing 1,1-bis(4-hydroxybenzene)-tetralin, characterized in that: The preparation method comprises: Under inert gas atmosphere and catalyst conditions, 1-tetralone and phenol are melted and reacted, and then separated and purified to obtain the 1,1-bis(4-hydroxybenzene)-tetralin.
2. The method for preparing 1,1-bis(4-hydroxybenzene)-tetralin according to claim 1, wherein The molar ratio of 1-tetralone to phenol is 1:(2.5-10).
3. The method for preparing 1,1-bis(4-hydroxybenzene)-tetralin according to claim 2, wherein: The molar ratio of the 1-tetralone to the phenol is 1:
4.
4. The method for preparing 1,1-bis(4-hydroxybenzene)-tetralin according to claim 1, wherein: The catalyst is a methanesulfonic acid-mercaptopropionic acid composite acid.
5. The method for preparing 1,1-bis(4-hydroxybenzene)-tetralin according to claim 1, characterized in that: The added amount of the catalyst is 0.05-0.5 of the molar equivalent of 1-tetralone.
6. The method for preparing 1,1-bis(4-hydroxybenzene)-tetralin according to claim 1, characterized in that: The amount of methanesulfonic acid added is 10-50 times the molar equivalent of mercaptopropionic acid.
7. The method for preparing 1,1-bis(4-hydroxybenzene)-tetralin according to claim 1, characterized in that: When the melt reaction is carried out, the reaction temperature is 45-65° C. and the reaction time is 6-24 hours.
8. 1,1-bis(4-hydroxybenzene)-tetralin prepared by the preparation method according to any one of claims 1 to 7, characterized in that: It has the chemical structure shown in Formula I:
9. Use of polyaryletherketone prepared from 1,1-bis(4-hydroxyphenyl)tetralin according to claim 8 in integrated circuit boards.