CN115305066A - Polycyclic aromatic hydrocarbon heat-conducting composition - Google Patents
Polycyclic aromatic hydrocarbon heat-conducting composition Download PDFInfo
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- CN115305066A CN115305066A CN202110494981.XA CN202110494981A CN115305066A CN 115305066 A CN115305066 A CN 115305066A CN 202110494981 A CN202110494981 A CN 202110494981A CN 115305066 A CN115305066 A CN 115305066A
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- 125000005575 polycyclic aromatic hydrocarbon group Chemical group 0.000 title claims abstract description 10
- 150000001491 aromatic compounds Chemical class 0.000 claims abstract description 44
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 claims description 60
- 229910021536 Zeolite Inorganic materials 0.000 claims description 36
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 36
- 239000010457 zeolite Substances 0.000 claims description 36
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims description 28
- 238000006243 chemical reaction Methods 0.000 claims description 25
- GRZJZRHVJAXMRR-UHFFFAOYSA-N 1-cyclohexyl-2-phenylbenzene Chemical group C1CCCCC1C1=CC=CC=C1C1=CC=CC=C1 GRZJZRHVJAXMRR-UHFFFAOYSA-N 0.000 claims description 14
- 238000005804 alkylation reaction Methods 0.000 claims description 14
- 238000009835 boiling Methods 0.000 claims description 12
- HHNHBFLGXIUXCM-GFCCVEGCSA-N cyclohexylbenzene Chemical compound [CH]1CCCC[C@@H]1C1=CC=CC=C1 HHNHBFLGXIUXCM-GFCCVEGCSA-N 0.000 claims description 11
- 239000002808 molecular sieve Substances 0.000 claims description 11
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims description 11
- 239000003377 acid catalyst Substances 0.000 claims description 6
- 230000029936 alkylation Effects 0.000 claims description 5
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- OQXMLPWEDVZNPA-UHFFFAOYSA-N 1,2-dicyclohexylbenzene Chemical compound C1CCCCC1C1=CC=CC=C1C1CCCCC1 OQXMLPWEDVZNPA-UHFFFAOYSA-N 0.000 claims description 4
- OLUVNSGCKHZQJQ-UHFFFAOYSA-N 1-cyclohexyl-4-(4-cyclohexylphenyl)benzene Chemical group C1CCCCC1C1=CC=C(C=2C=CC(=CC=2)C2CCCCC2)C=C1 OLUVNSGCKHZQJQ-UHFFFAOYSA-N 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- 239000003930 superacid Substances 0.000 claims description 4
- IWIOHRVOBOYWQE-UHFFFAOYSA-N (1-cyclohexylcyclohexyl)benzene Chemical compound C1CCCCC1C1(C=2C=CC=CC=2)CCCCC1 IWIOHRVOBOYWQE-UHFFFAOYSA-N 0.000 claims description 3
- UHXXWQVQLDPNKD-UHFFFAOYSA-N 1-cyclohexyl-2-(2-phenylphenyl)benzene Chemical group C1CCCCC1C1=CC=CC=C1C1=CC=CC=C1C1=CC=CC=C1 UHXXWQVQLDPNKD-UHFFFAOYSA-N 0.000 claims description 3
- 230000002194 synthesizing effect Effects 0.000 claims description 3
- HSDRNVLRTNPRNS-UHFFFAOYSA-N 1,2,3-tricyclohexylbenzene Chemical compound C1CCCCC1C1=CC=CC(C2CCCCC2)=C1C1CCCCC1 HSDRNVLRTNPRNS-UHFFFAOYSA-N 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 claims 1
- 238000007710 freezing Methods 0.000 abstract description 7
- 230000008014 freezing Effects 0.000 abstract description 7
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 15
- 239000003054 catalyst Substances 0.000 description 13
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 11
- 239000000047 product Substances 0.000 description 10
- 239000003921 oil Substances 0.000 description 9
- 239000007795 chemical reaction product Substances 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 5
- 238000009833 condensation Methods 0.000 description 5
- 230000005494 condensation Effects 0.000 description 5
- 238000012546 transfer Methods 0.000 description 5
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 3
- 230000006866 deterioration Effects 0.000 description 3
- 238000005265 energy consumption Methods 0.000 description 3
- 239000011973 solid acid Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
- 239000000571 coke Substances 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 238000013112 stability test Methods 0.000 description 2
- 239000004566 building material Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000005272 metallurgy Methods 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 238000010248 power generation Methods 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 239000002918 waste heat Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
- C09K5/08—Materials not undergoing a change of physical state when used
- C09K5/10—Liquid materials
Abstract
The invention discloses a polycyclic aromatic hydrocarbon heat-conducting composition, which mainly comprises the following components: a tricyclic aromatic compound of a C18 component and a tetracyclic aromatic compound of a C24 component, wherein the tetracyclic aromatic compound of the C24 component is present in an amount of 1 to 40 wt%, based on the total weight of the thermally conductive composition. The composition has excellent stability, the maximum use temperature can reach 380 ℃, and the freezing point is less than-15 ℃.
Description
Technical Field
The invention relates to a polycyclic aromatic hydrocarbon heat-conducting composition.
Background
The heat conducting oil is also called heat conducting oil, is a heat transfer medium, has the heat transfer performance of high temperature and low pressure, and has the advantages of high heat efficiency, uniform heat transfer, accurate temperature control, convenient transportation and long service life. The liquid-phase heat carrier has been developed to be the most widely used liquid-phase heat carrier with larger consumption, and is widely applied to the industries of petroleum, light industry, transportation, light industry, building materials, chemical fibers, textiles, artificial boards, organic silicon, electronic circuit boards, solar power generation, petrochemical industry, coatings, printing and dyeing, metallurgy waste heat utilization and the like.
The heat conduction oil used at present is mainly processed from petroleum products, and with the continuous rise of international petroleum price, the use cost of the traditional heat conduction oil is higher and higher. And the common hydrogenated terphenyl type heat conduction oil is prepared by catalytic hydrogenation at high temperature and high pressure, the reaction temperature is high in the technical process, a reaction tube is easy to coke and block, a plurality of devices are required to be operated in parallel, the investment is large, and the energy consumption is large. In addition, the yield of terphenyl is low (only about 18% of biphenyl), and the yield is limited by the market for selling biphenyl, so that the yield of partially hydrogenated terphenyl is seriously influenced.
Therefore, it is necessary to provide a heat transfer oil with excellent performance, such as low preparation cost, low energy and material consumption, and high product yield, and to provide a substance capable of replacing hydrogenated terphenyl to realize the application of the substance in the heat transfer oil.
Disclosure of Invention
The invention aims to overcome the technical defects that hydrogenated tribenzolized heat conducting oil is prepared by catalytic hydrogenation at high temperature and high pressure in the prior art, reaction temperature is high, a reaction tube is easy to coke and block, a plurality of devices are required to be operated in parallel, investment is high, energy consumption is high, and the preparation cost, energy consumption and material consumption are low, and the product yield is high.
The invention provides a polycyclic aromatic hydrocarbon heat-conducting composition, which mainly comprises the following components: a tricyclic aromatic compound of a C18 component and a tetracyclic aromatic compound of a C24 component, wherein the tetracyclic aromatic compound of the C24 component is present in an amount of 1 to 40 wt%, based on the total weight of the thermally conductive composition.
The heat-conducting composition has the advantages of good thermal stability, low condensation point and high working temperature.
The polycyclic aromatic hydrocarbon heat-conducting composition product has excellent heat stability, the maximum use temperature can reach 380 ℃, and the freezing point is less than-15 ℃. Can be used for replacing the traditional hydrogenated terphenyl product in the market.
The invention can be realized by alkylation reaction by using a solid acid catalyst without selective hydrogenation of terphenyl, and the product has the characteristics of excellent performance and low freezing point.
Detailed Description
The endpoints of the ranges and any values disclosed herein are not limited to the precise range or value, and these ranges or values should be understood to encompass values close to these ranges or values. For numerical ranges, each range between its endpoints and individual point values, and each individual point value can be combined with each other to give one or more new numerical ranges, and such numerical ranges should be construed as specifically disclosed herein.
The invention provides a polycyclic aromatic hydrocarbon heat-conducting composition, which mainly comprises the following components: a tricyclic aromatic compound of a C18 component and a tetracyclic aromatic compound of a C24 component, wherein the tetracyclic aromatic compound of the C24 component is present in an amount of 1 to 40 wt%, based on the total weight of the thermally conductive composition. The heat-conducting composition has the advantages of good heat stability, low condensation point and high working temperature.
According to a preferred embodiment of the invention, the tricyclic aromatic compound of the C18 component has a boiling point higher than 350 ℃, preferably higher than 353 ℃; and/or the tetracyclic aromatic compounds of the C24 component have a boiling point above 380 ℃ and preferably above 390 ℃.
According to a preferred embodiment of the present invention, the tetracyclic aromatic compound content of the C24 component is preferably in the range of 2 to 35 wt.%, more preferably 5 to 30 wt.%, even more preferably 10 to 30 wt.%, based on the total weight of the thermally conductive composition.
According to a preferred embodiment of the present invention, the tricyclic aromatic compound of the C18 component is contained in an amount of 60 to 99% by weight based on the total weight of the thermally conductive composition; preferably 70 to 90 wt%.
According to a preferred embodiment of the present invention, the content of the tricyclic aromatic compound of the C18 component is 60 to 99% by weight, and the content of the tetracyclic aromatic compound of the C24 component is 1 to 40% by weight, based on the total weight of the thermally conductive composition; preferably, the content of the tricyclic aromatic compound of the C18 component is 70 to 90% by weight, and the content of the tetracyclic aromatic compound of the C24 component is 10 to 30% by weight. The heat-conducting composition adopting the components has the advantages of good thermal stability, low condensation point and high working temperature.
According to a preferred embodiment of the present invention, the tricyclic aromatic compound of C18 component comprises one or more of cyclohexylphenylcyclohexane, dicyclohexylbenzene and cyclohexylbiphenyl compounds. The tricyclic aromatic compound adopting the C18 component has the advantages of good thermal stability and low condensation point.
According to a preferred embodiment of the present invention, the tetracyclic aromatic compound has a molecular structure comprising at least one aromatic ring, preferably one or more of dicyclohexylbiphenyl, tricyclohexylbenzene and cyclohexylterphenyl.
According to a preferred embodiment of the present invention, the method for synthesizing the tricyclic aromatic compound comprises: under the action of an acid catalyst, cyclohexylbenzene and cyclohexene and/or cyclohexanol undergo alkylation reaction.
According to a preferred embodiment of the present invention, when preparing the tricyclic aromatic compound, the acidic catalyst is selected from one or more of a zeolite molecular sieve, a solid super acid and HF, preferably a zeolite molecular sieve having a 12-membered ring channel structure, more preferably one or more of Y zeolite, MCM-22 zeolite and Beta zeolite, and still more preferably SiO of the zeolite molecular sieve 2 /Al 2 O 3 The molar ratio is from 5 to 100, preferably from 10 to 80.
According to a preferred embodiment of the present invention, when preparing the tricyclic aromatic compound, zeolite Y SiO is more preferred 2 /Al 2 O 3 The molar ratio is 2-10.
According to a preferred embodiment of the present invention, zeolite Beta SiO is used in the preparation of said tricyclic aromatic compound 2 /Al 2 O 3 The molar ratio is 20 to 50.
According to a preferred embodiment of the invention, the preparationSiO of MCM-22 zeolite as the tricyclic aromatic compound 2 /Al 2 O 3 The molar ratio is 20 to 40.
According to a preferred embodiment of the present invention, in preparing the tricyclic aromatic compound, the alkylation reaction conditions include: the reaction temperature is 100-250 ℃, preferably 120-220 ℃; the reaction pressure is 0.5-4 MPa, preferably 1-3 MPa; the molar ratio of the cyclohexylbenzene to the cyclohexene and/or cyclohexanol is 1-10, preferably 2-8; the weight space velocity of the cyclohexene and/or cyclohexanol is 0.1-2 hours -1 Preferably 0.2 to 1 hour -1 。
According to a preferred embodiment of the present invention, the method for synthesizing tetracyclic aromatic compounds comprises: under the action of an acid catalyst, cyclohexyl biphenyl or terphenyl and cyclohexene and/or cyclohexanol are subjected to alkylation reaction.
According to a preferred embodiment of the present invention, in the preparation of the tetracyclic aromatic compound, the acidic catalyst is selected from one or more of a zeolitic molecular sieve, a solid super acid and HF, preferably from a zeolitic molecular sieve having a 12-membered ring channel structure, more preferably from one or more of zeolite Y, zeolite MCM-22 and zeolite Beta.
According to a preferred embodiment of the present invention, zeolite Y, siO, is more preferred in the preparation of the tetracyclic aromatic compound 2 /Al 2 O 3 The molar ratio is 2 to 10.
According to a preferred embodiment of the present invention, zeolite Beta SiO is used in the preparation of the tetracyclic aromatic compound 2 /Al 2 O 3 The molar ratio is 20-50.
According to a preferred embodiment of the present invention, siO of zeolite MCM-22 is used in the preparation of said tetracyclic aromatic compound 2 /Al 2 O 3 The molar ratio is 20 to 40.
According to a preferred embodiment of the present invention, in preparing the tetracyclic aromatic compound, the alkylation conditions comprise: the reaction temperature is 110-260 ℃, preferably 130-230 ℃, and the reaction pressure is 0.5-4 MPa, preferably 1.0-3 MPa; the molar ratio of cyclohexylbiphenyl to cyclohexene and/or cyclohexanol is from 1 to 10, preferably from 2 to 7(ii) a The weight space velocity of the cyclohexene and/or cyclohexanol is 0.1-2 hours -1 Preferably 0.2 to 0.8 hour -1 。
The invention can be realized by alkylation reaction by using solid acid catalyst instead of selective hydrogenation of terphenyl, and the obtained product has the characteristics of excellent performance and low freezing point. The polycyclic aromatic hydrocarbon heat conducting oil mainly comprises a tricyclic aromatic hydrocarbon compound with a C18 component and a tetracyclic aromatic hydrocarbon compound composition with a C24 component. The tricyclic aromatic hydrocarbon compound at least comprises one of cyclohexylphenylcyclohexane, dicyclohexylbenzene, cyclohexylbiphenyl and the like, and has good thermal stability and proper kinematic viscosity. Meanwhile, the boiling point temperature of the heat-conducting composition is wide, and the range of the use temperature of the heat-conducting composition can be obviously improved.
According to a preferred embodiment of the present invention, the present invention provides a polycyclic aromatic hydrocarbon heat conductive composition, the main components of which are a C18 component tricyclic aromatic compound and a C24 component tetracyclic aromatic compound, wherein the C18 component can be derived from the alkylation of cyclohexylbenzene with cyclohexene and/or cyclohexanol to form dicyclohexylbenzene, and the C24 component can be derived from the alkylation of cyclohexylbiphenyl or terphenyl with cyclohexene and/or cyclohexanol to form one or more of dicyclohexylbiphenyl and cyclohexylterphenyl. The composition of the invention is found for the first time, and no prior art reports are found at all.
Cyclohexylbenzene is alkylated with cyclohexene or cyclohexanol and cyclohexylbiphenyl is alkylated with cyclohexene or cyclohexanol using typically acidic catalysts, typically solid acid catalysts, preferably zeolitic molecular sieves typically having a 12-membered ring channel structure, more preferably one or more of zeolite Y, zeolite MCM-22, zeolite Beta.
In the technical scheme, siO of the molecular sieve 2 /Al 2 O 3 The molar ratio is from 5 to 100, preferably from 10 to 80.
In the above technical scheme, the effective reaction conditions of the alkylation reaction of cyclohexylbenzene and cyclohexene or cyclohexanol include: the reaction temperature is 100-250 ℃, preferably 120-220 ℃, and the reaction pressure is 0.5-4 MPa, preferably 1-3 MPa;the cyclohexylbenzene/cyclohexene or cyclohexanol molar ratio is from 1.0 to 10, preferably from 2 to 8; the weight space velocity of the cyclohexene or cyclohexanol is 0.1-2 hours -1 Preferably 0.2 to 1 hour -1 。
In the above technical scheme, the effective reaction conditions for alkylation of cyclohexylbiphenyl with cyclohexene or cyclohexanol include: the reaction temperature is 110-260 ℃, preferably 130-230 ℃, and the reaction pressure is 0.5-4.0 MPa, preferably 1.0-3 MPa; cyclohexyl biphenyl/cyclohexene or cyclohexanol molar ratio 1-10, preferably 2-7; the weight space velocity of cyclohexene or cyclohexanol is 0.1-2 hours -1 Preferably 0.2 to 0.8 hour -1 。
The advantages of the present invention are illustrated in detail by the following examples, which are not intended to limit the scope of the invention.
Example 1
In the case of cyclohexylbenzene: cyclohexene =2.5, reaction temperature 185 ℃, and pressure 1.5MPa, the catalyst is Beta zeolite (SiO) 2 /Al 2 O 3 The molar ratio is 50), the space velocity of the cyclohexene is 0.15h -1 . The reaction product was separated and the fraction with a boiling point of more than 350 ℃ at atmospheric pressure was collected to obtain sample 1.
In the presence of cyclohexyl biphenyl: cyclohexene =2.0, reaction temperature 195 ℃, and pressure 2.0MPa, the catalyst is Beta zeolite (SiO) 2 /Al 2 O 3 The molar ratio is 30), the space velocity of the cyclohexene is 0.25h -1 . The reaction product was separated and the fraction with a boiling point at atmospheric pressure of more than 380 ℃ was collected to obtain sample 2.
Sample 1 was mixed with sample 2 in a composition ratio of 8.
Example 2
In the case of cyclohexylbenzene: cyclohexanol =3, reaction temperature 190 ℃, and pressure 2.0MPa, wherein the catalyst is MCM-22 zeolite (SiO-SiO) 2 /Al 2 O 3 The molar ratio is 30), the space velocity of the cyclohexanol is 0.25h -1 . The reaction product was separated and the fraction with a boiling point at atmospheric pressure greater than 350 c was collected to obtain sample 3.
In the presence of cyclohexyl biphenyl: cyclohexanol =2.0, reaction temperature 220 ℃, and pressure 2.0MPa, wherein the catalyst is Beta zeolite (SiO) 2 /Al 2 O 3 The molar ratio is 40), the space velocity of the cyclohexanol is 0.5h -1 . The reaction product was separated and the fraction with a boiling point of over 380 ℃ at atmospheric pressure was collected to obtain sample 4.
Sample 3 was mixed with sample 4 in a composition ratio of 7.
Example 3
In the presence of cyclohexylbenzene: cyclohexene =2.5, reaction temperature 175 ℃, and pressure 1.8MPa, the catalyst is MCM-22 zeolite (SiO) 2 /Al 2 O 3 The molar ratio is 40), the space velocity of the cyclohexene is 0.5h -1 . The reaction product was separated and the fraction with a boiling point at atmospheric pressure greater than 350 c was collected to obtain sample 5.
In the case of cyclohexyl biphenyl: cyclohexanol =2.0, reaction temperature 200 ℃, and catalyst Y zeolite (SiO zeolite) under pressure 2.5MPa 2 /Al 2 O 3 The molar ratio is 4), the space velocity of cyclohexanol is 0.25h -1 . The reaction product was separated and the fraction with a boiling point of over 380 ℃ at atmospheric pressure was collected to obtain sample 6.
Sample 5 was mixed with sample 6 in a composition ratio of 9.
Example 4
Sample 1 of example 1 was mixed with sample 6 of example 3 in a composition ratio of 6.
Example 5
Sample 3 of example 2 was mixed with sample 2 of example 1 in a composition ratio of 8.5.
Example 6
Sample 5 of example 3 was mixed with sample 4 of example 2 in a composition ratio of 7.5.
Example 7
In the case of terphenyl: cyclohexene =2.5, reaction temperature 190 ℃, and pressure 2.5MPa, the catalyst is Beta zeolite (SiO) 2 /Al 2 O 3 The molar ratio is 30), the space velocity of the cyclohexene is 0.25h -1 . The reaction product was separated and the fraction with a boiling point of over 380 ℃ at atmospheric pressure was collected to obtain sample 7.
Sample 1 of example 1 was mixed with sample 7 in a component ratio of 7.5 to obtain product 7.
Comparative example 1
Sample 1 of example 1 was mixed with sample 2 in a composition ratio of 2.
Comparative example 2
Hydrogenated terphenyl, prepared by conventional techniques on the market, was obtained as comparative example 2.
The above products were subjected to performance tests, and the test results are shown in table 1 below:
TABLE 1
As can be seen from the data in the table above, products 1-7 have several characteristics: firstly, the freezing points are lower and are all lower than-15 ℃, the requirements on the natural environment temperature are low, and the application range is wide; the thermal stability is good, the deterioration rate in the thermal stability test is less than 7.5, and the expected service life is longer. In addition, the products 2 and 4 have a self-ignition point of greater than 380 ℃ and are suitable for higher operating temperatures. Although comparative example 1 also had a higher self-ignition point, its deterioration rate and freezing point were higher; the freezing point of comparative example 2 was relatively high and the deterioration rate in the heat stability test was also relatively high. In conclusion, the heat-conducting composition adopting the components has the comprehensive advantages of good thermal stability, low condensation point and high working temperature.
The preferred embodiments of the present invention have been described above in detail, but the present invention is not limited thereto. Within the scope of the technical idea of the invention, many simple modifications can be made to the technical solution of the invention, including various technical features being combined in any other suitable way, and these simple modifications and combinations should also be regarded as the disclosure of the invention, and all fall within the scope of the invention.
Claims (10)
1. A polycyclic aromatic hydrocarbon heat-conducting composition is characterized in that the main components of the heat-conducting composition comprise: a tricyclic aromatic compound of a C18 component and a tetracyclic aromatic compound of a C24 component, wherein the tetracyclic aromatic compound of the C24 component is present in an amount of 1 to 40 wt%, based on the total weight of the thermally conductive composition.
2. The composition according to claim 1, wherein the tricyclic aromatic compound of the C18 component has a boiling point higher than 350 ℃, preferably higher than 353 ℃; and/or the tetracyclic aromatic compounds of the C24 component have a boiling point above 380 ℃ and preferably above 390 ℃.
3. The composition of claim 1 or 2, wherein the C18-component tricyclic aromatic compound comprises one or more of cyclohexylphenylcyclohexane, dicyclohexylbenzene, and cyclohexylbiphenyl compounds.
4. The composition according to any one of claims 1-3, wherein the tetracyclic aromatic hydrocarbon compound has a molecular structure comprising at least one aromatic ring, preferably one or more of dicyclohexylbiphenyl, tricyclohexylbenzene, and cyclohexylterphenyl, preferably dicyclohexylbiphenyl.
5. The composition of any one of claims 1-4, wherein the method of synthesizing the tricyclic aromatic compound comprises: under the action of an acid catalyst, cyclohexylbenzene and cyclohexene and/or cyclohexanol undergo alkylation reaction.
6. The composition of claim 5, wherein,
the acid catalyst is selected from one or more of zeolite molecular sieve, solid super acid and HF, preferably selected from zeolite molecular sieve with 12-membered ring channel structure, more preferably selected from one or more of Y zeolite, MCM-22 zeolite and Beta zeolite; and/or
The alkylation reaction conditions include: the reaction temperature is 100-250 ℃, preferably 120-220 ℃; the reaction pressure is 0.5-4 MPa, preferably 1-3 MPa; the mol ratio of the cyclohexylbenzene to the cyclohexene and/or cyclohexanol is 1-10, preferably 2-8; the weight space velocity of the cyclohexene and/or cyclohexanol is 0.1-2 hours -1 Preferably 0.2 to 1 hour -1 。
7. The composition of any one of claims 1-6, wherein the method of synthesis of the tetracyclic aromatic compound comprises: under the action of an acid catalyst, cyclohexyl biphenyl and cyclohexene and/or cyclohexanol are subjected to alkylation reaction.
8. The composition of claim 7, wherein the tetracyclic aromatic compound is synthesized by:
the acid catalyst is selected from one or more of zeolite molecular sieve, solid super acid and HF, preferably selected from zeolite molecular sieve with 12-membered ring channel structure, more preferably selected from one or more of Y zeolite, MCM-22 zeolite and Beta zeolite; and/or
The alkylation conditions include: the reaction temperature is 110-260 ℃, preferably 130-230 ℃, and the reaction pressure is 0.5-4 MPa, preferably 1-3 MPa; the molar ratio of the cyclohexyl biphenyl to the cyclohexene and/or cyclohexanol is 1-10, preferably 2-7; the weight space velocity of the cyclohexene and/or cyclohexanol is 0.1-2 hours -1 Preferably 0.2 to 0.8 hour -1 。
9. The composition according to any one of claims 1 to 8, wherein the tetracyclic aromatic hydrocarbon compound content of the C24 component is 2 to 35 wt. -%, more preferably 5 to 30 wt. -%, and still more preferably 10 to 30 wt. -%, based on the total weight of the thermally conductive composition.
10. The composition of any of claims 1-9, wherein the tricyclic aromatic compound of the C18 component is present in an amount of 60 to 99 wt.%, based on the total weight of the thermally conductive composition; preferably 70 to 90 wt%.
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| CN109749778A (en) * | 2018-11-29 | 2019-05-14 | 洛阳瑞华新能源技术发展有限公司 | A kind of hydrogenation modification reaction method of the material of the high aromatic hydrocarbons containing higher boiling |
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2021
- 2021-05-07 CN CN202110494981.XA patent/CN115305066A/en active Pending
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| US5384059A (en) * | 1991-12-13 | 1995-01-24 | Bayer Aktiengesellschaft | Heat transfer fluid and process for its preparation |
| CN105694968A (en) * | 2016-01-02 | 2016-06-22 | 何巨堂 | Reverse feed high-aromatic-hydrocarbon hydro-upgrading method |
| CN109456736A (en) * | 2018-10-19 | 2019-03-12 | 江苏中能化学科技股份有限公司 | A kind of high―temperature nuclei type conduction oil |
| CN109749778A (en) * | 2018-11-29 | 2019-05-14 | 洛阳瑞华新能源技术发展有限公司 | A kind of hydrogenation modification reaction method of the material of the high aromatic hydrocarbons containing higher boiling |
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