CN112442339B - Preparation method for synthesizing heat conduction oil at high temperature - Google Patents
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- tetrahydronaphthalene
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- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- 230000002194 synthesizing effect Effects 0.000 title claims description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims abstract description 24
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 claims abstract description 22
- 238000006243 chemical reaction Methods 0.000 claims abstract description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 18
- 238000003756 stirring Methods 0.000 claims abstract description 12
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 12
- 239000003377 acid catalyst Substances 0.000 claims abstract description 11
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 11
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000003054 catalyst Substances 0.000 claims abstract description 9
- 239000002904 solvent Substances 0.000 claims abstract description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 238000001816 cooling Methods 0.000 claims abstract description 4
- 239000007789 gas Substances 0.000 claims abstract description 4
- 238000010438 heat treatment Methods 0.000 claims abstract description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 14
- 238000012546 transfer Methods 0.000 claims description 11
- HQCUSXPGMKCZGE-UHFFFAOYSA-N 1-(1-phenylethyl)-1,2,3,4-tetrahydronaphthalene Chemical compound C1CCC2=CC=CC=C2C1C(C)C1=CC=CC=C1 HQCUSXPGMKCZGE-UHFFFAOYSA-N 0.000 claims description 9
- TXOHWLOHKUPUKO-UHFFFAOYSA-N 5-(1-phenylethyl)-1,2,3,4-tetrahydronaphthalene Chemical compound C=1C=CC=2CCCCC=2C=1C(C)C1=CC=CC=C1 TXOHWLOHKUPUKO-UHFFFAOYSA-N 0.000 claims description 9
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical group S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 239000007868 Raney catalyst Substances 0.000 claims description 4
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 4
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 4
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 4
- 239000011968 lewis acid catalyst Substances 0.000 claims description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 3
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical group Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 3
- 229910015900 BF3 Inorganic materials 0.000 claims description 2
- DSVGQVZAZSZEEX-UHFFFAOYSA-N [C].[Pt] Chemical compound [C].[Pt] DSVGQVZAZSZEEX-UHFFFAOYSA-N 0.000 claims description 2
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 claims description 2
- 238000004321 preservation Methods 0.000 abstract description 4
- 238000000926 separation method Methods 0.000 abstract 1
- 239000003921 oil Substances 0.000 description 23
- 238000009835 boiling Methods 0.000 description 5
- 238000004817 gas chromatography Methods 0.000 description 5
- 238000010992 reflux Methods 0.000 description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- MHCVCKDNQYMGEX-UHFFFAOYSA-N 1,1'-biphenyl;phenoxybenzene Chemical compound C1=CC=CC=C1C1=CC=CC=C1.C=1C=CC=CC=1OC1=CC=CC=C1 MHCVCKDNQYMGEX-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000003442 catalytic alkylation reaction Methods 0.000 description 1
- 238000004523 catalytic cracking Methods 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000004134 energy conservation Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000008676 import Effects 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
Classifications
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- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/54—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition of unsaturated hydrocarbons to saturated hydrocarbons or to hydrocarbons containing a six-membered aromatic ring with no unsaturation outside the aromatic ring
- C07C2/64—Addition to a carbon atom of a six-membered aromatic ring
- C07C2/66—Catalytic processes
- C07C2/68—Catalytic processes with halides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/54—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition of unsaturated hydrocarbons to saturated hydrocarbons or to hydrocarbons containing a six-membered aromatic ring with no unsaturation outside the aromatic ring
- C07C2/72—Addition to a non-aromatic carbon atom of hydrocarbons containing a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/02—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation
- C07C5/10—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation of aromatic six-membered rings
- C07C5/11—Partial hydrogenation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/04—Purification; Separation; Use of additives by distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2525/00—Catalysts of the Raney type
- C07C2525/02—Raney nickel
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- C07C2527/06—Halogens; Compounds thereof
- C07C2527/125—Compounds comprising a halogen and scandium, yttrium, aluminium, gallium, indium or thallium
- C07C2527/126—Aluminium chloride
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
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- Chemical & Material Sciences (AREA)
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- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Physics & Mathematics (AREA)
- Combustion & Propulsion (AREA)
- Thermal Sciences (AREA)
- Materials Engineering (AREA)
- Analytical Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Water Supply & Treatment (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a preparation method for high-temperature synthesis of heat conduction oil, which comprises the following steps: putting naphthalene into an autoclave, adding 2.5-3.8% of catalyst, after gas replacement, heating to 150-300 ℃, stirring, introducing hydrogen at the pressure of 3.2-4.0 Mpa, cooling after reaction, removing the catalyst, and rectifying the separated tetrahydronaphthalene; adding tetrahydronaphthalene into a reaction kettle, adding a solvent, adding 1-5% of an acid catalyst, stirring, dropwise adding styrene, wherein the molar ratio of styrene to tetrahydronaphthalene is 0.7-0.9: 1, the dropwise adding temperature is 75-85 ℃, carrying out heat preservation reaction for 1-5 hours after dropwise adding, adding water, standing for layering, separating a water layer, and carrying out rectification separation to obtain a finished product.
Description
Technical Field
The invention relates to the technical field of conductor heat flow, in particular to a preparation method for high-temperature synthesis of heat conduction oil.
Background
The heat conducting oil is an organic heat carrier and is divided into a synthetic type and a mineral type. The mineral heat conducting oil is prepared by refining distillate oil which is formed in the process of carrying out high-temperature cracking or catalytic cracking on petroleum and is used as a raw material after adding an additive, and the main component is a hydrocarbon mixture; the synthetic heat conducting oil is produced by a chemical synthesis process, has a certain chemical structure and a determined chemical name, and is mainly characterized in that the molecular structure contains aromatic hydrocarbon or naphthenic hydrocarbon structures, and most of the aromatic hydrocarbon compounds are aromatic hydrocarbon compounds with two rings or three rings.
The synthetic heat transfer oil has wider use temperature range, can be used at low, medium and high temperature, and the mineral heat transfer oil can only be used at low and medium temperature; the synthetic heat transfer oil has better thermal stability and longer service life, the synthetic heat transfer oil can be reused after regeneration, and the mineral oil can not be regenerated.
The industrial production of synthetic heat-conducting oil in developed countries such as Europe, America and Japan starts from 30 s of the 20 th century, the research and development starts in the 60 s of the 20 th century, and the development is rapid after the 90 s. At present, a plurality of kinds of synthetic heat transfer oil cannot be produced domestically, and only can be imported, Dowtherm RP produced by Dow chemical in America belongs to the category, and is an isomer mixture of 1,2,3, 4-tetrahydro-1- (1-phenethyl) naphthalene and 1,2,3, 4-tetrahydro-5- (1-phenethyl) naphthalene. The steam generator has the advantages of high use temperature, low saturated steam pressure, good thermal stability and the like, is not produced at home at present, and can only depend on import for use by customers. In order to break through the technical monopoly of foreign and international companies and fill up the blank of domestic technology and market, the preparation method of the heat conduction oil needs to be researched and invented.
Disclosure of Invention
The invention aims to overcome the defects in the prior art and provides a preparation method for synthesizing heat conduction oil at high temperature.
In order to achieve the purpose, the technical scheme adopted by the invention is as follows:
the invention provides a preparation method for synthesizing heat conduction oil at high temperature, which comprises the following steps:
the method comprises the following steps: synthesis of tetrahydronaphthalenes
Putting naphthalene into an autoclave, adding 2.5-3.8% of catalyst, after gas replacement, heating to 150-300 ℃, stirring, introducing hydrogen at the pressure of 3.2-4.0 Mpa, cooling after reaction, removing the catalyst, and rectifying the separated tetrahydronaphthalene;
step two: synthesis of heat transfer oil
Adding tetrahydronaphthalene into a reaction kettle, adding a solvent, adding 1-5% of an acid catalyst, stirring, dropwise adding styrene at a molar ratio of styrene to tetrahydronaphthalene of 0.7-0.9: 1 at 75-85 ℃, carrying out heat preservation reaction for 1-5 hours after dropwise adding, adding water, standing for layering, removing a water layer, and carrying out reduced pressure distillation to obtain a finished product.
As a preferred embodiment of the invention, the finished product is an isomeric mixture of 1,2,3, 4-tetrahydro-1- (1-phenylethyl) naphthalene and 1,2,3, 4-tetrahydro-5- (1-phenylethyl) naphthalene.
As a preferred embodiment of the present invention, the molar ratio of ethylene to tetrahydronaphthalene is 0.8: 1.
As a preferred embodiment of the present invention, the catalyst in the first step is selected from Raney nickel, palladium carbon or platinum carbon.
As a preferred embodiment of the present invention, the acid catalyst in the second step is selected from lewis acid catalysts or protonic acid catalysts.
As a preferred embodiment of the present invention, the lewis acid catalyst is selected from iron trichloride, aluminum trichloride or boron trifluoride and the protonic acid catalyst is selected from sulfuric acid or phosphoric acid.
As a preferred embodiment of the present invention, the step two solvent is selected from dichloroethane or carbon tetrachloride.
As a preferred embodiment of the invention, the adding amount of the solvent in the second step is 2-6 times of the mass of the tetrahydronaphthalene.
As a preferred embodiment of the invention, the amount of water added in the second step is 1-5 times of the mass of the acid catalyst.
Adopt the produced beneficial effect of above-mentioned technical scheme to lie in:
the technical scheme of the invention is to prepare high-temperature heat-conducting oil by taking naphthalene as a raw material through catalytic hydrogenation and alkylation reactions.
The hydrogenation reduction reaction of the technical scheme provided by the invention adopts the most advanced and green process at present, and the material directly reacts with hydrogen under the action of the catalyst, so that the cost is low, no pollution is caused, the product yield is high, and the quality is good.
The technical scheme provided by the invention adopts the alkylation of tetrahydronaphthalene and styrene to synthesize the heat conduction oil, the reaction is carried out at low temperature and low pressure, the safety and the reliability are realized, the solvent can be recycled, the cost is low, and no pollution is caused.
The method provided by the invention has the advantages of low raw material cost, mild conditions, energy conservation, consumption reduction and environmental friendliness, and is suitable for industrial mass production.
The high-temperature heat conduction oil prepared by the technical scheme of the invention is an isomer mixture of 1,2,3, 4-tetrahydro-1- (1-phenethyl) naphthalene and 1,2,3, 4-tetrahydro-5- (1-phenethyl) naphthalene, and has the advantages of low viscosity, high flash point and high boiling point.
The method provided by the invention effectively breaks through the technical blockade of developed countries such as Europe and America to our country, and fills the domestic blank.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention will be described in detail and fully with reference to the following embodiments.
EXAMPLE 1 Synthesis of Tetrahydronaphthalenes
Putting naphthalene into a high-pressure kettle, adding 3.1% Raney nickel, replacing gas, heating to 180 ℃, stirring, introducing hydrogen at the pressure of 3.0Mpa, cooling to room temperature after the reaction is finished, removing Raney nickel, and rectifying separated tetrahydronaphthalene.
Example 2 Synthesis of Heat transfer oils
Adding 400g of tetrahydronaphthalene into a reaction kettle, adding 1600g of carbon tetrachloride, adding 12g of aluminum trichloride, stirring, then dropwise adding 226g of styrene, wherein the dropwise adding temperature is the reflux temperature of the carbon tetrachloride, carrying out heat preservation reaction for 3 hours after dropwise adding, adding 36g of water, standing for layering, separating out a water layer, rectifying and separating to obtain a finished product, and analyzing by gas chromatography: 1,2,3, 4-tetrahydro-1- (1-phenylethyl) naphthalene and 1,2,3, 4-tetrahydro-5- (1-phenylethyl) naphthalene in a ratio of 8:2 and a kinematic viscosity of 15mm2The boiling point at standard conditions was 338 ℃ and the flash point (open) was 196 ℃.
Example 3 Synthesis of Heat transfer oils
Adding 400g of tetrahydronaphthalene into a reaction kettle, adding 2400g of dichloroethane, adding 20g of sulfuric acid, stirring, then dropwise adding 226g of styrene, wherein the dropwise adding temperature is the reflux temperature of carbon tetrachloride, carrying out heat preservation reaction for 3 hours after dropwise adding, adding 100g of water, standing for layering, separating a water layer, rectifying and separating to obtain a finished product, and analyzing by gas chromatography: 1,2,3, 4-tetrahydro-1- (1-phenylethyl) naphthalene and 1,2,3, 4-tetrahydro-5- (1-phenylethyl) naphthalene in a ratio of 8:2 and a kinematic viscosity of 15mm2The boiling point at standard conditions was 338 ℃ and the flash point (open) was 196 ℃.
Example 4 Synthesis of Heat transfer oils
Adding 400g of tetrahydronaphthalene into a reaction kettle, adding 800g of dichloroethane, adding 4g of ferric trichloride, stirring, then dropwise adding 254g of styrene, wherein the dropwise adding temperature is the reflux temperature of carbon tetrachloride, keeping warm after dropwise adding for reaction for 3 hours, adding 12g of water, standing for layering, separating a water layer, rectifying and separating to obtain a finished product, and analyzing by gas chromatography: 1,2,3, 4-tetrahydro-1- (1-phenylethyl) naphthalene and 1,2,3, 4-tetrahydro-5- (1-phenylethyl) naphthalene in a ratio of 8:2 and a kinematic viscosity of 15mm2The boiling point at standard conditions was 338 ℃ and the flash point (open) was 196 ℃.
338 ℃ and a flash point (open) of 196 ℃.
Example 5 Synthesis of Heat transfer oils
Adding 400g of tetrahydronaphthalene into a reaction kettle, adding 1600g of dichloroethane, adding 12g of phosphoric acid, stirring, then dropwise adding 198g of styrene, wherein the dropwise adding temperature is the reflux temperature of carbon tetrachloride, keeping warm after dropwise adding for reaction for 4 hours, adding 48g of water, standing for layering, separating a water layer, rectifying and separating to obtain a finished product, and analyzing by gas chromatography: 1,2,3, 4-tetrahydro-1- (1-phenylethyl) naphthalene and 1,2,3, 4-tetrahydro-5- (1-phenylethyl) naphthalene in a ratio of 8:2 and a kinematic viscosity of 15mm2The boiling point at standard conditions was 338 ℃ and the flash point (open) was 196 ℃.
Comparative example 1
Adding 400g of tetrahydronaphthalene into a reaction kettle, adding 12g of phosphoric acid, stirring, then dropwise adding 198g of styrene, keeping the dropwise adding temperature at 78 ℃, reacting for 4 hours after dropwise adding, adding 48g of water, standing for layering, separating a water layer, rectifying and separating to obtain a finished product, and analyzing by gas chromatography: 1,2,3, 4-tetrahydro-1- (1-phenylethyl) naphthalene and 1,2,3, 4-tetrahydro-5- (1-phenylethyl) naphthalene in a ratio of 3:7 and a kinematic viscosity of 24mm2S, flash point (open) 185 ℃.
Finally, it should be noted that: the above examples are only intended to illustrate the technical solution of the present invention, but not to limit it; although the present invention has been described in detail with reference to the foregoing embodiments, it will be understood by those of ordinary skill in the art that: the technical solutions described in the foregoing embodiments may still be modified, or some technical features may be equivalently replaced; and such modifications or substitutions do not depart from the spirit and scope of the corresponding technical solutions of the embodiments of the present invention.
Claims (1)
1. The preparation method for synthesizing the heat conduction oil at the high temperature is characterized by comprising the following steps of:
the method comprises the following steps: synthesis of tetrahydronaphthalenes
Putting naphthalene into an autoclave, adding 2-3.8% of catalyst, after gas replacement, heating to 150-300 ℃, stirring, introducing hydrogen at the pressure of 3.2-4.0 Mpa, cooling after reaction, removing the catalyst, and rectifying the separated tetrahydronaphthalene;
step two: synthesis of heat transfer oil
Adding tetrahydronaphthalene into a reaction kettle, adding a solvent, adding 1-5% of an acid catalyst, stirring, dropwise adding styrene, wherein the molar ratio of styrene to tetrahydronaphthalene is 0.8:1, the dropwise adding temperature is 75-85 ℃, keeping the temperature for reaction for 1-5 hours after dropwise adding, adding water, standing for layering, removing a water layer, and rectifying and separating to obtain a finished product, wherein the finished product is an isomer mixture of 1,2,3, 4-tetrahydro-1- (1-phenylethyl) naphthalene and 1,2,3, 4-tetrahydro-5- (1-phenylethyl) naphthalene;
the solvent in the second step is selected from dichloroethane or carbon tetrachloride;
the catalyst in the first step is selected from Raney nickel, palladium carbon or platinum carbon;
the acid catalyst in the second step is selected from Lewis acid catalyst or protonic acid catalyst;
the Lewis acid catalyst is selected from ferric trichloride, aluminum trichloride or boron trifluoride;
the protonic acid catalyst is selected from sulfuric acid or phosphoric acid;
the adding amount of the solvent in the second step is 2-6 times of the mass of the tetrahydronaphthalene;
and in the second step, the amount of water added is 1-5 times of the mass of the acid catalyst.
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| CN102627952A (en) * | 2012-03-21 | 2012-08-08 | 常州市武进东方绝缘油有限公司 | 1,1-phenyltetralylethane isomer used as heat transfer fluid and synthetic method thereof |
| CN103508834A (en) * | 2013-10-09 | 2014-01-15 | 江苏中能化学有限公司 | High-selectivity method for synthesizing 1, 1-phenyltetralyl ethane isomer as heat-conducting fluid |
| CN104193578A (en) * | 2014-08-21 | 2014-12-10 | 邯郸惠达化工有限公司 | Method for producing decahydronaphthalene and tetrahydronaphthalene by naphthalene hydrogenation |
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Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4689436A (en) * | 1985-05-13 | 1987-08-25 | Idemitsu Kosan Company Limited | Process for producing alkenyl-aromatic hydrocarbon derivatives |
| US6888036B2 (en) * | 2000-03-29 | 2005-05-03 | Arkema | Mono-and polybenzyl-1,2,3,4-tetrahydronaphthalene compositions, use of said compositions or mixture of monobenzyl-,1,2,3,4-tetrahydronaphthalene as heat transfer fluid |
| CN102627952A (en) * | 2012-03-21 | 2012-08-08 | 常州市武进东方绝缘油有限公司 | 1,1-phenyltetralylethane isomer used as heat transfer fluid and synthetic method thereof |
| CN103508834A (en) * | 2013-10-09 | 2014-01-15 | 江苏中能化学有限公司 | High-selectivity method for synthesizing 1, 1-phenyltetralyl ethane isomer as heat-conducting fluid |
| CN104193578A (en) * | 2014-08-21 | 2014-12-10 | 邯郸惠达化工有限公司 | Method for producing decahydronaphthalene and tetrahydronaphthalene by naphthalene hydrogenation |
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