CN109970521A - A kind of preparation method of dodecyl diphenyl oxide - Google Patents
A kind of preparation method of dodecyl diphenyl oxide Download PDFInfo
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- CN109970521A CN109970521A CN201910386191.2A CN201910386191A CN109970521A CN 109970521 A CN109970521 A CN 109970521A CN 201910386191 A CN201910386191 A CN 201910386191A CN 109970521 A CN109970521 A CN 109970521A
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- dodecyl diphenyl
- diphenyl oxide
- dodecanol
- diphenyl ether
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/30—Preparation of ethers by reactions not forming ether-oxygen bonds by increasing the number of carbon atoms, e.g. by oligomerisation
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
- C10M105/18—Ethers, e.g. epoxides
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
- C10M2207/0406—Ethers; Acetals; Ortho-esters; Ortho-carbonates used as base material
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Abstract
The present invention relates to a kind of preparation methods of dodecyl diphenyl oxide comprising following steps: after n-dodecanol and diphenyl ether are mixed, being heated to 55 DEG C~65 DEG C, inorganic acid catalyst is added dropwise, react 6~10h, obtain dodecyl diphenyl oxide crude product；It after the dodecyl diphenyl oxide crude product and sodium hydrate aqueous solution are mixed, is extracted with organic solvent, collects organic phase, anhydrous sodium sulfate is added, after mixing, filtered, collect filtrate rotary evaporation at 45~55 DEG C, obtain the dodecyl diphenyl oxide.The beneficial effects of the present invention are: the lubricating oil by-product that the 1, present invention synthesizes is few, physicochemical property and excellent lubricating properties；2, present invention process operates easier, energy conservation and environmental protection, is convenient for industrializing implementation.
Description
Technical field
The present invention relates to a kind of preparation methods of dodecyl diphenyl oxide, belong to technical field of organic synthesis.
Background technique
Lubricating oil is used in various types automobile, on mechanical equipment to reduce friction, protection is mechanical and the liquid of workpiece
Or semisolid lubricants, the effects of mainly playing lubrication, cooling, antirust, cleaning, sealing and buffer.
The most basic traditional production method of lube base oil is physical method, i.e., " old three sets " traditional skills, including solvent essence
3 main production link " old three sets " traditional handicrafts such as system, solvent dewaxing and clay finishing have low in cost, base oil
Yield is high, the high feature of byproduct paraffin melting point, and also contains on a small quantity in the base oil produced by method for refining solvent
Aromatic hydrocarbons, therefore all there is very strong solvability to oxidation product and additive, old three sets of technique because of its irreplaceable advantage,
Still it is play an important role in lube base oil production.
And in " old three sets " method, using method for refining solvent production lube base oil to crude quality dependence very
Greatly, not all crude oil can use production lube base oil, and can not produce Viscosity Index height, II low class of pour point
And III class base oil.Solvent dewaxing process has loss to the viscosity of raw material, and operating condition is harsh.Clay finishing technique can have
The polar compound of residual solvent and sulfur-bearing, nitrogen, oxygen in effect ground removing oil product, but there are carclazyte dosage is big in technical process,
The problems such as serious refined oil loss of dust pollution is big.
In recent years, many lubrication products such as lubricating oil or lubricating grease is required in high temperature, high pressure and high load capacity etc. it is harsh
Under the conditions of use, therefore, modern lubricant has to the heat resistance and inoxidizability that have excellent.
It is important to obtain balance between the cost and performance of base oil, to provide low cost but high performance lubrication
Oil and lubricating grease.Alkyl diphenyl ether has excellent thermal stability and oxidisability, and evaporation is few when especially using at high temperature, glues
Degree variation is small, and other universal synthetic lubricants can hardly obtain such characteristic.
The preparation method of present dodecyl diphenyl oxide is synthesized under 270 DEG C or more hot conditions, generally
Preparation is not able to satisfy in laboratory condition to require.
Summary of the invention
For the defects in the prior art, the object of the present invention is to provide a kind of preparation methods of dodecyl diphenyl oxide.
The present invention is achieved by the following technical solutions:
A kind of preparation method of dodecyl diphenyl oxide comprising following steps:
After n-dodecanol and diphenyl ether are mixed, 55 DEG C~65 DEG C are heated to, is added dropwise inorganic acid catalyst, reaction 6~
10h obtains dodecyl diphenyl oxide crude product；
It after the dodecyl diphenyl oxide crude product and sodium hydrate aqueous solution are mixed, is extracted, is received with organic solvent
Collect organic phase, anhydrous sodium sulfate is added, after mixing, filters, collect filtrate rotary evaporation at 45~55 DEG C, obtain described 12
Alkyl diphenyl ether.
Reaction route are as follows:
Preferably, the molar ratio of the n-dodecanol and diphenyl ether is 1: (0.5~2.0).
Preferably, the additional amount of the inorganic acid catalyst is the 1% of n-dodecanol weight.
Preferably, the inorganic acid catalyst is the concentrated sulfuric acid.
A kind of purposes by the dodecyl diphenyl oxide of preceding method preparation in lube base oil.
Compared with prior art, the present invention have it is following the utility model has the advantages that
1, the lubricating oil by-product that the present invention synthesizes is few, physicochemical property and excellent lubricating properties；
2, present invention process operates easier, energy conservation and environmental protection, is convenient for industrializing implementation.
Detailed description of the invention
Upon reading the detailed description of non-limiting embodiments with reference to the following drawings, other feature of the invention,
Objects and advantages will become more apparent upon:
Fig. 1 is that the 1H-NMR of 1 product of embodiment schemes；
Fig. 2 is that the 1H-NMR of 2 product of embodiment schemes；
Fig. 3 is that the 1H-NMR of 3 product of embodiment schemes；
Fig. 4 is that the 1H-NMR of 4 product of embodiment schemes；
Fig. 5 is that the 1H-NMR of 5 product of embodiment schemes；
Fig. 6 is that the 1H-NMR of 6 product of embodiment schemes；
Fig. 7 is that the 1H-NMR of 7 product of embodiment schemes；
Fig. 8 is that the 1H-NMR of 8 product of embodiment schemes；
Fig. 9 is that the 1H-NMR of 9 product of embodiment schemes；
Figure 10 is that the 1H-NMR of 10 product of embodiment schemes；
Figure 11 is that the 1H-NMR of 11 product of embodiment schemes；
Figure 12 is that the 1H-NMR of 12 product of embodiment schemes.
Specific embodiment
The present invention is described in detail combined with specific embodiments below.Following embodiment will be helpful to the technology of this field
Personnel further understand the present invention, but the invention is not limited in any way.It should be pointed out that the ordinary skill of this field
For personnel, without departing from the inventive concept of the premise, various modifications and improvements can be made.These belong to the present invention
Protection scope.
Embodiment 1
(1) take following raw material for standby: diphenyl ether (99%), n-dodecanol (analyze pure, the limited public affairs of Chinese medicines group chemical reagent
Department), the concentrated sulfuric acid (98%), sodium hydroxide (analyze pure, Sinopharm Chemical Reagent Co., Ltd.), ethyl acetate (analyze pure, state
Chemical reagent Co., Ltd, medicine group), anhydrous sodium sulfate (analyze pure, Sinopharm Chemical Reagent Co., Ltd.).
(2) using n-dodecanol and diphenyl ether as raw material, using organic acid as catalyst, in the round-bottomed flask with condenser pipe
N-dodecanol 3.72g is added, magneton is added in diphenyl ether 1.7g (n-dodecanol: the molar ratio of diphenyl ether is 1: 0.5).Round bottom is burnt
Bottle merging 60 DEG C of thermostatical oil baths in, the concentrated sulfuric acid of 1.22mL is slowly added dropwise while stirring, 1min is added dropwise, keep temperature in
60 DEG C, the reaction was continued 6h.
(3) after reaction, reactant is cooled to room temperature, and pours into the beaker for filling sodium hydrate aqueous solution (5mol/L)
In, it is poured into separatory funnel after being sufficiently mixed, in separatory funnel plus lower water is isolated in ethyl acetate extraction, standing liquid separation
Phase collects upper organic phase, then lower layer's water phase is repeated extraction 2 times.
(4) appropriate anhydrous sodium sulfate is added in the upper organic phase gathered, is filtered after standing 3h, takes filtrate.Rotation
Filtrate rotation is evaporated by evaporimeter temperature at 45 DEG C~55 DEG C, when filtrate is all no longer blistered in 5min, collects product.It produces
Object is dodecyl diphenyl oxide.
The 1H-NMR of dodecyl diphenyl oxide manufactured in the present embodiment scheme as shown in Figure 1, chemical shift 6.9~7.5 it
Between be hydrogen peak on diphenyl ether, chemical shift is the hydrogen peak on benzyl, chemical potential between 2.0~2.5 and 3.5~4.5
Shifting is the hydrogen peak on alkyl between 0.5~2.0.
Embodiment 2
(1) take following raw material for standby: diphenyl ether (99%), n-dodecanol (analyze pure, the limited public affairs of Chinese medicines group chemical reagent
Department), the concentrated sulfuric acid (98%), sodium hydroxide (analyze pure, Sinopharm Chemical Reagent Co., Ltd.), ethyl acetate (analyze pure, state
Chemical reagent Co., Ltd, medicine group), anhydrous sodium sulfate (analyze pure, Sinopharm Chemical Reagent Co., Ltd.).
(2) using n-dodecanol and diphenyl ether as raw material, using organic acid as catalyst, in the round-bottomed flask with condenser pipe
N-dodecanol 3.72g is added, magneton is added in diphenyl ether 3.4g (n-dodecanol: the molar ratio of diphenyl ether is 1: 1.0).Round bottom is burnt
Bottle merging 60 DEG C of thermostatical oil baths in, the concentrated sulfuric acid of 1.22mL is slowly added dropwise while stirring, 1min is added dropwise, keep temperature in
60 DEG C, the reaction was continued 6h.
(3) after reaction, reactant is cooled to room temperature, and pours into the beaker for filling sodium hydrate aqueous solution (5mol/L)
In, it is poured into separatory funnel after being sufficiently mixed, in separatory funnel plus lower water is isolated in ethyl acetate extraction, standing liquid separation
Phase collects upper organic phase, then lower layer's water phase is repeated extraction 2 times.
(4) appropriate anhydrous sodium sulfate is added in the upper organic phase gathered, is filtered after standing 3h, takes filtrate.Rotation
Filtrate rotation is evaporated by evaporimeter temperature at 45 DEG C~55 DEG C, when filtrate is all no longer blistered in 5min, collects product.It produces
Object is dodecyl diphenyl oxide.
The 1H-NMR of dodecyl diphenyl oxide manufactured in the present embodiment scheme as shown in Fig. 2, chemical shift 6.9~7.5 it
Between be hydrogen peak on diphenyl ether, chemical shift is the hydrogen peak on benzyl, chemical potential between 2.0~2.5 and 3.5~4.5
Shifting is the hydrogen peak on alkyl between 0.5~2.0.
Embodiment 3
(1) take following raw material for standby: diphenyl ether (99%), n-dodecanol (analyze pure, the limited public affairs of Chinese medicines group chemical reagent
Department), the concentrated sulfuric acid (98%), sodium hydroxide (analyze pure, Sinopharm Chemical Reagent Co., Ltd.), ethyl acetate (analyze pure, state
Chemical reagent Co., Ltd, medicine group), anhydrous sodium sulfate (analyze pure, Sinopharm Chemical Reagent Co., Ltd.).
(2) using n-dodecanol and diphenyl ether as raw material, using organic acid as catalyst, in the round-bottomed flask with condenser pipe
N-dodecanol 3.72g is added, magneton is added in diphenyl ether 5.1g (n-dodecanol: the molar ratio of diphenyl ether is 1: 1.5).Round bottom is burnt
Bottle merging 60 DEG C of thermostatical oil baths in, the concentrated sulfuric acid of 1.22mL is slowly added dropwise while stirring, 1min is added dropwise, keep temperature in
60 DEG C, the reaction was continued 6h.
(3) after reaction, reactant is cooled to room temperature, and pours into the beaker for filling sodium hydrate aqueous solution (5mol/L)
In, it is poured into separatory funnel after being sufficiently mixed, in separatory funnel plus lower water is isolated in ethyl acetate extraction, standing liquid separation
Phase collects upper organic phase, then lower layer's water phase is repeated extraction 2 times.
(4) appropriate anhydrous sodium sulfate is added in the upper organic phase gathered, is filtered after standing 3h, takes filtrate.Rotation
Filtrate rotation is evaporated by evaporimeter temperature at 45 DEG C~55 DEG C, when filtrate is all no longer blistered in 5min, collects product.It produces
Object is dodecyl diphenyl oxide.
The 1H-NMR of dodecyl diphenyl oxide manufactured in the present embodiment scheme as shown in figure 3, chemical shift 6.9~7.5 it
Between be hydrogen peak on diphenyl ether, chemical shift is the hydrogen peak on benzyl, chemical potential between 2.0~2.5 and 4.0~4.5
Shifting is the hydrogen peak on alkyl between 0.5~2.0.
Embodiment 4
(1) take following raw material for standby: diphenyl ether (99%), n-dodecanol (analyze pure, the limited public affairs of Chinese medicines group chemical reagent
Department), the concentrated sulfuric acid (98%), sodium hydroxide (analyze pure, Sinopharm Chemical Reagent Co., Ltd.), ethyl acetate (analyze pure, state
Chemical reagent Co., Ltd, medicine group), anhydrous sodium sulfate (analyze pure, Sinopharm Chemical Reagent Co., Ltd.).
(2) using n-dodecanol and diphenyl ether as raw material, using organic acid as catalyst, in the round-bottomed flask with condenser pipe
N-dodecanol 3.72g is added, magneton is added in diphenyl ether 6.8g (n-dodecanol: the molar ratio of diphenyl ether is 1: 2.0).Round bottom is burnt
Bottle merging 60 DEG C of thermostatical oil baths in, the concentrated sulfuric acid of 1.22mL is slowly added dropwise while stirring, 1min is added dropwise, keep temperature in
60 DEG C, the reaction was continued 6h.
(3) after reaction, reactant is cooled to room temperature, and pours into the beaker for filling sodium hydrate aqueous solution (5mol/L)
In, it is poured into separatory funnel after being sufficiently mixed, in separatory funnel plus lower water is isolated in ethyl acetate extraction, standing liquid separation
Phase collects upper organic phase, then lower layer's water phase is repeated extraction 2 times.
(4) appropriate anhydrous sodium sulfate is added in the upper organic phase gathered, is filtered after standing 3h, takes filtrate.Rotation
Filtrate rotation is evaporated by evaporimeter temperature at 45 DEG C~55 DEG C, when filtrate is all no longer blistered in 5min, collects product.It produces
Object is dodecyl diphenyl oxide.
The 1H-NMR of dodecyl diphenyl oxide manufactured in the present embodiment scheme as shown in figure 4, chemical shift 6.9~7.5 it
Between be hydrogen peak on diphenyl ether, chemical shift is the hydrogen peak on benzyl, chemical potential between 2.0~2.5 and 3.5~4.5
Shifting is the hydrogen peak on alkyl between 0.5~2.0.
Embodiment 5
(1) take following raw material for standby: diphenyl ether (99%), n-dodecanol (analyze pure, the limited public affairs of Chinese medicines group chemical reagent
Department), the concentrated sulfuric acid (98%), sodium hydroxide (analyze pure, Sinopharm Chemical Reagent Co., Ltd.), ethyl acetate (analyze pure, state
Chemical reagent Co., Ltd, medicine group), anhydrous sodium sulfate (analyze pure, Sinopharm Chemical Reagent Co., Ltd.).
(2) using n-dodecanol and diphenyl ether as raw material, using organic acid as catalyst, in the round-bottomed flask with condenser pipe
N-dodecanol 3.72g is added, magneton is added in diphenyl ether 1.7g (n-dodecanol: the molar ratio of diphenyl ether is 1: 0.5).Round bottom is burnt
Bottle merging 60 DEG C of thermostatical oil baths in, the concentrated sulfuric acid of 1.22mL is slowly added dropwise while stirring, 1min is added dropwise, keep temperature in
60 DEG C, the reaction was continued 8h.
(3) after reaction, reactant is cooled to room temperature, and pours into the beaker for filling sodium hydrate aqueous solution (5mol/L)
In, it is poured into separatory funnel after being sufficiently mixed, in separatory funnel plus lower water is isolated in ethyl acetate extraction, standing liquid separation
Phase collects upper organic phase, then lower layer's water phase is repeated extraction 2 times.
(4) appropriate anhydrous sodium sulfate is added in the upper organic phase gathered, is filtered after standing 3h, takes filtrate.Rotation
Filtrate rotation is evaporated by evaporimeter temperature at 45 DEG C~55 DEG C, when filtrate is all no longer blistered in 5min, collects product.It produces
Object is dodecyl diphenyl oxide.
The 1H-NMR of dodecyl diphenyl oxide manufactured in the present embodiment scheme as shown in figure 5, chemical shift 6.9~7.5 it
Between be hydrogen peak on diphenyl ether, chemical shift is the hydrogen peak on benzyl, chemical potential between 2.0~2.5 and 3.5~4.5
Shifting is the hydrogen peak on alkyl between 0.0~2.0.
Embodiment 6
(1) take following raw material for standby: diphenyl ether (99%), n-dodecanol (analyze pure, the limited public affairs of Chinese medicines group chemical reagent
Department), the concentrated sulfuric acid (98%), sodium hydroxide (analyze pure, Sinopharm Chemical Reagent Co., Ltd.), ethyl acetate (analyze pure, state
Chemical reagent Co., Ltd, medicine group), anhydrous sodium sulfate (analyze pure, Sinopharm Chemical Reagent Co., Ltd.).
(2) using n-dodecanol and diphenyl ether as raw material, using organic acid as catalyst, in the round-bottomed flask with condenser pipe
N-dodecanol 3.72g is added, magneton is added in diphenyl ether 3.4g (n-dodecanol: the molar ratio of diphenyl ether is 1: 1.0).Round bottom is burnt
Bottle merging 60 DEG C of thermostatical oil baths in, the concentrated sulfuric acid of 1.22mL is slowly added dropwise while stirring, 1min is added dropwise, keep temperature in
60 DEG C, the reaction was continued 8h.
(3) after reaction, reactant is cooled to room temperature, and pours into the beaker for filling sodium hydrate aqueous solution (5mol/L)
In, it is poured into separatory funnel after being sufficiently mixed, in separatory funnel plus lower water is isolated in ethyl acetate extraction, standing liquid separation
Phase collects upper organic phase, then lower layer's water phase is repeated extraction 2 times.
(4) appropriate anhydrous sodium sulfate is added in the upper organic phase gathered, is filtered after standing 3h, takes filtrate.Rotation
Filtrate rotation is evaporated by evaporimeter temperature at 45 DEG C~55 DEG C, when filtrate is all no longer blistered in 5min, collects product.It produces
Object is dodecyl diphenyl oxide.
The 1H-NMR of dodecyl diphenyl oxide manufactured in the present embodiment scheme as shown in fig. 6, chemical shift 6.9~7.5 it
Between be hydrogen peak on diphenyl ether, chemical shift is the hydrogen peak on benzyl, chemical potential between 2.0~2.5 and 3.5~4.5
Shifting is the hydrogen peak on alkyl between 0.0~2.0.
Embodiment 7
(1) take following raw material for standby: diphenyl ether (99%), n-dodecanol (analyze pure, the limited public affairs of Chinese medicines group chemical reagent
Department), the concentrated sulfuric acid (98%), sodium hydroxide (analyze pure, Sinopharm Chemical Reagent Co., Ltd.), ethyl acetate (analyze pure, state
Chemical reagent Co., Ltd, medicine group), anhydrous sodium sulfate (analyze pure, Sinopharm Chemical Reagent Co., Ltd.).
(2) using n-dodecanol and diphenyl ether as raw material, using organic acid as catalyst, in the round-bottomed flask with condenser pipe
N-dodecanol 3.72g is added, magneton is added in diphenyl ether 5.1g (n-dodecanol: the molar ratio of diphenyl ether is 1: 1.5).Round bottom is burnt
Bottle merging 60 DEG C of thermostatical oil baths in, the concentrated sulfuric acid of 1.22mL is slowly added dropwise while stirring, 1min is added dropwise, keep temperature in
60 DEG C, the reaction was continued 8h.
(3) after reaction, reactant is cooled to room temperature, and pours into the beaker for filling sodium hydrate aqueous solution (5mol/L)
In, it is poured into separatory funnel after being sufficiently mixed, in separatory funnel plus lower water is isolated in ethyl acetate extraction, standing liquid separation
Phase collects upper organic phase, then lower layer's water phase is repeated extraction 2 times.
(4) appropriate anhydrous sodium sulfate is added in the upper organic phase gathered, is filtered after standing 3h, takes filtrate.Rotation
Filtrate rotation is evaporated by evaporimeter temperature at 45 DEG C~55 DEG C, when filtrate is all no longer blistered in 5min, collects product.It produces
Object is dodecyl diphenyl oxide.
The 1H-NMR of dodecyl diphenyl oxide manufactured in the present embodiment scheme as shown in fig. 7, chemical shift 6.9~7.5 it
Between be hydrogen peak on diphenyl ether, chemical shift is the hydrogen peak on benzyl, chemical potential between 2.0~2.5 and 3.5~4.5
Shifting is the hydrogen peak on alkyl between 0.0~2.0.
Embodiment 8
(1) take following raw material for standby: diphenyl ether (99%), n-dodecanol (analyze pure, the limited public affairs of Chinese medicines group chemical reagent
Department), the concentrated sulfuric acid (98%), sodium hydroxide (analyze pure, Sinopharm Chemical Reagent Co., Ltd.), ethyl acetate (analyze pure, state
Chemical reagent Co., Ltd, medicine group), anhydrous sodium sulfate (analyze pure, Sinopharm Chemical Reagent Co., Ltd.).
(2) using n-dodecanol and diphenyl ether as raw material, using organic acid as catalyst, in the round-bottomed flask with condenser pipe
N-dodecanol 3.72g is added, magneton is added in diphenyl ether 6.8g (n-dodecanol: the molar ratio of diphenyl ether is 1: 2.0).Round bottom is burnt
Bottle merging 60 DEG C of thermostatical oil baths in, the concentrated sulfuric acid of 1.22mL is slowly added dropwise while stirring, 1min is added dropwise, keep temperature in
60 DEG C, the reaction was continued 8h.
(3) after reaction, reactant is cooled to room temperature, and pours into the beaker for filling sodium hydrate aqueous solution (5mol/L)
In, it is poured into separatory funnel after being sufficiently mixed, in separatory funnel plus lower water is isolated in ethyl acetate extraction, standing liquid separation
Phase collects upper organic phase, then lower layer's water phase is repeated extraction 2 times.
(4) appropriate anhydrous sodium sulfate is added in the upper organic phase gathered, is filtered after standing 3h, takes filtrate.Rotation
Filtrate rotation is evaporated by evaporimeter temperature at 45 DEG C~55 DEG C, when filtrate is all no longer blistered in 5min, collects product.It produces
Object is dodecyl diphenyl oxide.
The 1H-NMR of dodecyl diphenyl oxide manufactured in the present embodiment scheme as shown in figure 8, chemical shift 6.9~7.5 it
Between be hydrogen peak on diphenyl ether, chemical shift is the hydrogen peak on benzyl, chemical potential between 2.0~2.5 and 3.5~4.5
Shifting is the hydrogen peak on alkyl between 0.0~2.0.
Embodiment 9
(1) take following raw material for standby: diphenyl ether (99%), n-dodecanol (analyze pure, the limited public affairs of Chinese medicines group chemical reagent
Department), the concentrated sulfuric acid (98%), sodium hydroxide (analyze pure, Sinopharm Chemical Reagent Co., Ltd.), ethyl acetate (analyze pure, state
Chemical reagent Co., Ltd, medicine group), anhydrous sodium sulfate (analyze pure, Sinopharm Chemical Reagent Co., Ltd.).
(2) using n-dodecanol and diphenyl ether as raw material, using organic acid as catalyst, in the round-bottomed flask with condenser pipe
N-dodecanol 3.72g is added, magneton is added in diphenyl ether 1.7g (n-dodecanol: the molar ratio of diphenyl ether is 1: 0.5).Round bottom is burnt
Bottle merging 60 DEG C of thermostatical oil baths in, the concentrated sulfuric acid of 1.22mL is slowly added dropwise while stirring, 1min is added dropwise, keep temperature in
60 DEG C, the reaction was continued 10h.
(3) after reaction, reactant is cooled to room temperature, and pours into the beaker for filling sodium hydrate aqueous solution (5mol/L)
In, it is poured into separatory funnel after being sufficiently mixed, in separatory funnel plus lower water is isolated in ethyl acetate extraction, standing liquid separation
Phase collects upper organic phase, then lower layer's water phase is repeated extraction 2 times.
(4) appropriate anhydrous sodium sulfate is added in the upper organic phase gathered, is filtered after standing 3h, takes filtrate.Rotation
Filtrate rotation is evaporated by evaporimeter temperature at 45 DEG C~55 DEG C, when filtrate is all no longer blistered in 5min, collects product.It produces
Object is dodecyl diphenyl oxide.
The 1H-NMR of dodecyl diphenyl oxide manufactured in the present embodiment scheme as shown in figure 9, chemical shift 6.9~7.5 it
Between be hydrogen peak on diphenyl ether, chemical shift is the hydrogen peak on benzyl, chemical potential between 2.0~2.5 and 3.5~4.5
Shifting is the hydrogen peak on alkyl between 0.5~2.0.
Embodiment 10
(1) take following raw material for standby: diphenyl ether (99%), n-dodecanol (analyze pure, the limited public affairs of Chinese medicines group chemical reagent
Department), the concentrated sulfuric acid (98%), sodium hydroxide (analyze pure, Sinopharm Chemical Reagent Co., Ltd.), ethyl acetate (analyze pure, state
Chemical reagent Co., Ltd, medicine group), anhydrous sodium sulfate (analyze pure, Sinopharm Chemical Reagent Co., Ltd.).
(2) using n-dodecanol and diphenyl ether as raw material, using organic acid as catalyst, in the round-bottomed flask with condenser pipe
N-dodecanol 3.72g is added, magneton is added in diphenyl ether 3.4g (n-dodecanol: the molar ratio of diphenyl ether is 1: 1.0).Round bottom is burnt
Bottle merging 60 DEG C of thermostatical oil baths in, the concentrated sulfuric acid of 1.22mL is slowly added dropwise while stirring, 1min is added dropwise, keep temperature in
60 DEG C, the reaction was continued 10h.
(3) after reaction, reactant is cooled to room temperature, and pours into the beaker for filling sodium hydrate aqueous solution (5mol/L)
In, it is poured into separatory funnel after being sufficiently mixed, in separatory funnel plus lower water is isolated in ethyl acetate extraction, standing liquid separation
Phase collects upper organic phase, then lower layer's water phase is repeated extraction 2 times.
(4) appropriate anhydrous sodium sulfate is added in the upper organic phase gathered, is filtered after standing 3h, takes filtrate.Rotation
Filtrate rotation is evaporated by evaporimeter temperature at 45 DEG C~55 DEG C, when filtrate is all no longer blistered in 5min, collects product.It produces
Object is dodecyl diphenyl oxide.
Dodecyl diphenyl oxide manufactured in the present embodiment 1H-NMR figure as shown in Figure 10, chemical shift 6.9~7.5 it
Between be hydrogen peak on diphenyl ether, chemical shift is the hydrogen peak on benzyl, chemical potential between 2.0~2.5 and 3.5~4.5
Shifting is the hydrogen peak on alkyl between 0.0~2.0.
Embodiment 11
(1) take following raw material for standby: diphenyl ether (99%), n-dodecanol (analyze pure, the limited public affairs of Chinese medicines group chemical reagent
Department), the concentrated sulfuric acid (98%), sodium hydroxide (analyze pure, Sinopharm Chemical Reagent Co., Ltd.), ethyl acetate (analyze pure, state
Chemical reagent Co., Ltd, medicine group), anhydrous sodium sulfate (analyze pure, Sinopharm Chemical Reagent Co., Ltd.).
(2) using n-dodecanol and diphenyl ether as raw material, using organic acid as catalyst, in the round-bottomed flask with condenser pipe
N-dodecanol 3.72g is added, magneton is added in diphenyl ether 5.1g (n-dodecanol: the molar ratio of diphenyl ether is 1: 1.5).Round bottom is burnt
Bottle merging 60 DEG C of thermostatical oil baths in, the concentrated sulfuric acid of 1.22mL is slowly added dropwise while stirring, 1min is added dropwise, keep temperature in
60 DEG C, the reaction was continued 10h.
(3) after reaction, reactant is cooled to room temperature, and pours into the beaker for filling sodium hydrate aqueous solution (5mol/L)
In, it is poured into separatory funnel after being sufficiently mixed, in separatory funnel plus lower water is isolated in ethyl acetate extraction, standing liquid separation
Phase collects upper organic phase, then lower layer's water phase is repeated extraction 2 times.
(4) appropriate anhydrous sodium sulfate is added in the upper organic phase gathered, is filtered after standing 3h, takes filtrate.Rotation
Filtrate rotation is evaporated by evaporimeter temperature at 45 DEG C~55 DEG C, when filtrate is all no longer blistered in 5min, collects product.It produces
Object is dodecyl diphenyl oxide.
Dodecyl diphenyl oxide manufactured in the present embodiment 1H-NMR figure as shown in figure 11, chemical shift 6.9~7.5 it
Between be hydrogen peak on diphenyl ether, chemical shift is the hydrogen peak on benzyl, chemical potential between 2.0~2.5 and 3.5~4.5
Shifting is the hydrogen peak on alkyl between 0.0~2.0.
Embodiment 12
(1) take following raw material for standby: diphenyl ether (99%), n-dodecanol (analyze pure, the limited public affairs of Chinese medicines group chemical reagent
Department), the concentrated sulfuric acid (98%), sodium hydroxide (analyze pure, Sinopharm Chemical Reagent Co., Ltd.), ethyl acetate (analyze pure, state
Chemical reagent Co., Ltd, medicine group), anhydrous sodium sulfate (analyze pure, Sinopharm Chemical Reagent Co., Ltd.).
(2) using n-dodecanol and diphenyl ether as raw material, using organic acid as catalyst, in the round-bottomed flask with condenser pipe
N-dodecanol 3.72g is added, magneton is added in diphenyl ether 6.8g (n-dodecanol: the molar ratio of diphenyl ether is 1: 2.0).Round bottom is burnt
Bottle merging 60 DEG C of thermostatical oil baths in, the concentrated sulfuric acid of 1.22mL is slowly added dropwise while stirring, 1min is added dropwise, keep temperature in
60 DEG C, the reaction was continued 10h.
(3) after reaction, reactant is cooled to room temperature, and pours into the beaker for filling sodium hydrate aqueous solution (5mol/L)
In, it is poured into separatory funnel after being sufficiently mixed, in separatory funnel plus lower water is isolated in ethyl acetate extraction, standing liquid separation
Phase collects upper organic phase, then lower layer's water phase is repeated extraction 2 times.
(4) appropriate anhydrous sodium sulfate is added in the upper organic phase gathered, is filtered after standing 3h, takes filtrate.
Filtrate rotation is evaporated by Rotary Evaporators temperature at 45 DEG C~55 DEG C, when filtrate is all no longer blistered in 5min, is collected and is produced
Object.Product is dodecyl diphenyl oxide.
Dodecyl diphenyl oxide manufactured in the present embodiment 1H-NMR figure as shown in figure 12, chemical shift 6.9~7.5 it
Between be hydrogen peak on diphenyl ether, chemical shift is the hydrogen peak on benzyl, chemical potential between 2.0~2.5 and 3.5~4.5
Shifting is the hydrogen peak on alkyl between 0.0~2.0.
Specific embodiments of the present invention are described above.It is to be appreciated that the invention is not limited to above-mentioned
Particular implementation, those skilled in the art can make various deformations or amendments within the scope of the claims, this not shadow
Ring substantive content of the invention.
Claims (5)
1. a kind of preparation method of dodecyl diphenyl oxide, which comprises the steps of:
After n-dodecanol and diphenyl ether are mixed, 55 DEG C~65 DEG C are heated to, inorganic acid catalyst is added dropwise, 6~10h is reacted, obtains
To dodecyl diphenyl oxide crude product；
After the dodecyl diphenyl oxide crude product and sodium hydrate aqueous solution are mixed, extracted with organic solvent, collection has
Anhydrous sodium sulfate is added in machine phase, after mixing, filters, collects filtrate rotary evaporation at 45~55 DEG C, obtain the dodecyl
Diphenyl ether.
2. the preparation method of dodecyl diphenyl oxide as described in claim 1, which is characterized in that the n-dodecanol and hexichol
The molar ratio of ether is 1: (0.5~2.0).
3. the preparation method of dodecyl diphenyl oxide as described in claim 1, which is characterized in that the inorganic acid catalyst
Additional amount is the 1% of n-dodecanol weight.
4. the preparation method of dodecyl diphenyl oxide as claimed in claim 1 or 3, which is characterized in that the inorganic acid catalysis
Agent is the concentrated sulfuric acid.
5. a kind of purposes by the dodecyl diphenyl oxide of claim 1 the method preparation in lube base oil.
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Citations (5)
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| CN105175234A (en) * | 2015-07-23 | 2015-12-23 | 厦门大学 | Synthetic method for dodecyl diphenyl ether |
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| US5552071A (en) * | 1991-01-04 | 1996-09-03 | Mobil Oil Corporation | Alkylated diphenyl ether lubricants |
| CN1524839A (en) * | 2003-02-27 | 2004-09-01 | 北京大学 | Method for synthesizing linear alkyl diphenyl ether |
| CN1915969A (en) * | 2006-09-05 | 2007-02-21 | 太原理工大学 | Method for synthesizing alkyl diphenyl ether sulfonate |
| CN105175234A (en) * | 2015-07-23 | 2015-12-23 | 厦门大学 | Synthetic method for dodecyl diphenyl ether |
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