CN102766022A - Method for synthesizing 3,3,3-trifluoro-propyl alcohol - Google Patents
Method for synthesizing 3,3,3-trifluoro-propyl alcohol Download PDFInfo
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- CN102766022A CN102766022A CN201210286304XA CN201210286304A CN102766022A CN 102766022 A CN102766022 A CN 102766022A CN 201210286304X A CN201210286304X A CN 201210286304XA CN 201210286304 A CN201210286304 A CN 201210286304A CN 102766022 A CN102766022 A CN 102766022A
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Abstract
The invention discloses a method for synthesizing 3,3,3-trifluoro-propyl alcohol. 2-dibromo3,3,3-trifluoropropene serves as the raw material, and the method includes the following steps: (1) adding methanol and alkali in stirring mode, then adding 2-dibromo3,3,3-trifluoropropene, warming to 70 DEG C, reacting for 6h, and obtaining 3,3,3-trifluoropropene-methyl ether by washing reaction liquor, wherein mole ratio of 2-dibromo3,3,3-trifluoropropene: methanol: alkali is 1:(3-8):(2.4-6.2); and (2) adding 3,3,3-trifluoropropene-methyl ether, organic ester and activated Raney Ni catalysts into an autoclave, leading hydrogen pressure to be 5MPa, stirring to lead temperature to rise to 60-120 DEG C, reacting for 4-8h, and filtering and distilling reaction liquor to obtain 3,3,3-trifluoro-propyl alcohol, wherein mass ratio of 3,3,3-trifluoropropene-methyl ether: organic ester: catalysts is 1:(1.2-2.0):(0.05-0.2). The method is mainly used for preparing 3,3,3-trifluoro-propyl alcohol.
Description
Technical field
The present invention relates to a kind ofly 3,3, the compound method of 3-trifluoropropanol relates in particular to a kind ofly with 2-bromine 3,3, and the 3-trifluoro propene is 3,3 of a raw material, the preparation method of 3-trifluoropropanol.
Background technology
3,3, the 3-trifluoropropanol can be used as the midbody of synthetic medicine, agricultural chemicals, also can be used as the raw material or the midbody of synthesized high-performance material." Investigation of the factors controlling the regioselectivity of the hydroboration of fluoroolefins " Chemical communication, 2002,386～387 disclose a kind of 3; 3; The preparation method of 3-trifluoropropanol, this method are that raw material prepares 3,3 through two-step reaction with the trifluoro propene; The 3-trifluoropropanol, reactions step is following:
At first, trifluoro propene and the reaction of dibromo borine make boron cpd, and hydrolysis oxidation obtains trifluoropropanol again, reaction yield 41%.But this method reaction yield is lower; And the reaction of second step is aqueous systems, and there are azeotropic in trifluoropropanol and water, and it is difficult that the product last handling process separates purification.
Summary of the invention
The technical problem that the present invention will solve is deficiency and the defective that overcomes in the background technology, provide that a kind of reaction yield is higher, product separate better simply 3,3, the preparation method of 3-trifluoropropanol.
Synthetic route of the present invention is:
In order to solve the problems of the technologies described above, of the present invention 3,3, the preparation method of 3-trifluoropropanol, this method are with 2-bromine 3,3, and the 3-trifluoro propene is a raw material, comprises the steps:
(1) stir down, methyl alcohol, alkali are joined in the reactor drum, add 2-bromine 3,3 again, the 3-trifluoro propene, heat temperature raising to 70 ℃, reaction 6h, reaction solution obtains 3,3 through water-washing step, 3-trifluoro-propenyl methyl ether; Wherein the 2-bromine 3,3,3-trifluoro propene: methyl alcohol: the mol ratio of alkali is 1: 3～8: 2.4～6; Said alkali is sodium hydroxide, Pottasium Hydroxide.(2) with 3,3, the Raney Ni catalyzer that 3-trifluoro-propenyl methyl ether, organic ester and activation are good joins in the autoclave, is 5MPa at hydrogen pressure; Stirring heating is warming up to 60 ℃～120 ℃, reaction 4h～8h, and reaction solution is through filtration, distilation steps; Obtain 3,3, the 3-trifluoropropanol; Wherein 3,3,3-trifluoro-propenyl methyl ether: organic ester: the catalyst quality ratio is 1: 1.2～2.0: 0.05～0.2; Described ester is the aliphatic ester of C4～C6 or the aromatic ester of C7～C9.
The present invention is preferred 3,3, and the preparation method of 3-trifluoropropanol comprises the steps:
(1) stirs down, 3 mole, of methanol 96g and 2 molar sodium hydroxide 80g are joined in the reactor drum, add 0.5 mole of 2-bromo-3,3 again, 3-trifluoro propene 87.5g, heat temperature raising to 70 ℃, reaction 6h; Reaction solution obtains 3,3 through water-washing step, 3-trifluoro-propenyl methyl ether.(2) with 44.1g 3,3, the Raney Ni catalyzer that 3-trifluoro-propenyl methyl ether, 61.7g methyl valerate and 5g activation are good joins in the autoclave, and filling hydrogen pressure is 5MPa; Stir down, be warming up to 100 ℃, reaction 6h, reaction solution is through filtration, distilation steps; Obtain 3,3, the 3-trifluoropropanol.
Beneficial effect of the present invention:
Reaction yield of the present invention is higher, and 3,3, the yield of 3-trifluoropropanol can reach 62%; And the method in the documents, 3,3, the yield of 3-trifluoropropanol is 41%; In addition, method 3,3 of the present invention, the aftertreatment of 3-trifluoropropanol is simple, only can obtain the trifluoropropanol of purity 98% through distillation; And in the documents 3,3, the aftertreatment of 3-trifluoropropanol is loaded down with trivial details, must obtain the trifluoropropanol of purity 98% through azeotropic distillation.
Embodiment
Through specific embodiment the present invention is done further explain below, but protection scope of the present invention is not limited to this.
Purity check instrument: extra large glad GC-930 type gas chromatograph, the 30m DB-5 of the Agilent company (capillary chromatographic column of 50m * 0.32mm).
Analysis condition: 50 ℃ of post stove initial temperatures, constant temperature 4min, 10 ℃/min temperature programming to 250 ℃, it is 250 ℃ with detector temperature that temperature of vaporization chamber is 280 ℃.
Raney Ni catalyst activation process: stir down, with in 150g alumino nickel and the 500g water adding reactor drum, heat temperature raising to 70 ℃; Under this temperature, drip 30% sodium hydroxide solution 1000g, after dripping, heat temperature raising to 80 ℃; Reaction 4h is cooled to room temperature, topples over the reaction solution upper strata and removes aqueous sodium hydroxide solution; Lower floor's catalyst layer is washed three times to neutral with 1000g, is stored in the water catalyzer subsequent use.
Embodiment 1
(1) stir down, with 96g methyl alcohol, 80g sodium hydroxide adds in the reactor drum, adds 87.5g 2-bromine 3,3 again; The 3-trifluoro propene, heat temperature raising to 70 ℃, reaction 6h is cooled to room temperature; Discharging, reaction solution is washed three times to neutral with 100g, removes methyl alcohol, Sodium Bromide and sodium hydroxide, obtains 3; 3,3-trifluoro-propenyl methyl ether 44.1g, yield 70%, purity is 98%.
(2) with 44.1g 3,3, the RaneyNi catalyzer that 3-trifluoro-propenyl methyl ether, 61.7g methyl valerate and 5g activation are good joins in the autoclave, and filling hydrogen pressure is 5MPa, stirs down; Heat temperature raising to 100 ℃, reaction 6h is cooled to room temperature, shifts out reaction solution, filtering reacting liquid; Catalyzer is separated with reaction solution, and air distillation gained filtrating is collected 87～89 ℃ of cuts, gets 3,3; 3-trifluoropropanol 36.1g, yield 88.7%, purity 98%, two step total recovery 62%.
Intermediate structure is identified:
MS：m/z?126(M
+)，91(100)。
IR(KBr)，υ/cm
-1：3002，2951，1681，1465，1291，1139，975。
13CNMR(CDCl
3)，δ/ppm：147.6(CH，C1)，121.5(CF
3，C3)，93.8(CH，C2)，55.90(OCH3)。
1HNMR(CDCl
3)，δ/ppm：6.79(d，1H)，4.70(d，1H)3.80(s，3H)。
The said structure appraising datum confirms that method gained material of the present invention is 3,3 really, 3-trifluoro-propenyl methyl ether.
Product structure is identified:
MS：m/z114(M
+)，31(100)。
IR(KBr)，υ/cm
-1：3363，2962，1387，1256，1148，1003。
13CNNR(CDCl
3)，δ/ppm：127.57(CF
3，C3)，56.18(C，C1)，36.86(CH
2，C2)。
1HNMR(CDCl
3)，δ/ppm：3.90(m，2H)，2.38(m，2H)。
The said structure appraising datum confirms that method gained material of the present invention is 3,3 really, the 3-trifluoropropanol.
Embodiment 2
(1) stir down, with 128g methyl alcohol, 80g sodium hydroxide adds in the reactor drum, adds 87.5g2-bromine 3,3 again; The 3-trifluoro propene is warming up to 70 ℃, and reaction 6h is cooled to room temperature; Discharging, reaction solution is washed three times to neutral with 100g, removes methyl alcohol, Sodium Bromide and sodium hydroxide, obtains 3; 3,3-trifluoro-propenyl methyl ether 42.8g, yield 68.0%, purity is 98%.
(2) with 42.8g 3,3,3-trifluoro-propenyl methyl ether, the RaneyNi catalyzer that 68.5g butyl valerate and 4.3g activation are good adds in the autoclave, and filling hydrogen pressure is 5MPa; Stir down, be warming up to 100 ℃, reaction 6h is cooled to room temperature, shifts out reaction solution; Filtering reacting liquid separates catalyzer with reaction solution, air distillation gained filtrating is collected 87～89 ℃ of cuts, gets 3; 3,3-trifluoropropanol 32.5g, yield 82.5%, purity 98%.Two step total recoverys 56.1%
Embodiment 3
(1) stir down, with 128g methyl alcohol, 120g sodium hydroxide adds in the reactor drum, adds 87.5g2-bromine 3,3 again; The 3-trifluoro propene is warming up to 70 ℃, and reaction 6h is cooled to room temperature; Discharging, reaction solution is washed three times to neutral with 100g, removes methyl alcohol, Sodium Bromide and sodium hydroxide, obtains 3; 3,3-trifluoro-propenyl methyl ether 43.5g, yield 69.1%, purity is 98%.
(2) with 43.5g 3,3,3-trifluoro-propenyl methyl ether, the RaneyNi catalyzer that 52.2g butyl butyrate and 3.0g activation are good adds in the autoclave, and filling hydrogen pressure is 5MPa; Stir down, be warming up to 70 ℃, reaction 6h is cooled to room temperature, shifts out reaction solution; Filtering reacting liquid separates catalyzer with reaction solution, air distillation gained filtrating is collected 87～89 ℃ of cuts, gets 3; 3,3-trifluoropropanol 31.5g, yield 78.5%, purity 98%.Two step total recoverys 54.3%
Embodiment 4
(1) stirs down, 48g methyl alcohol and 48g sodium hydroxide are added in the reactor drum, add 87.5g2-bromine 3,3 again; The 3-trifluoro propene is warming up to 70 ℃, and reaction 6h is cooled to room temperature; Discharging, reaction solution is washed three times to neutral with 100g, removes methyl alcohol, Sodium Bromide and sodium hydroxide, obtains 3; 3,3-trifluoro-propenyl methyl ether 41.1g, yield 65.2%, purity is 98%.
(2) with 41.1g 3,3,3-trifluoro-propenyl methyl ether, the Raney Ni catalyzer that 74.0g oil of Niobe and 3.3g activation are good adds in the autoclave, and filling hydrogen pressure is 5MPa; Stir down, be warming up to 90 ℃, reaction 6h is cooled to room temperature, shifts out reaction solution; Filtering reacting liquid separates catalyzer with reaction solution, air distillation gained filtrating is collected 87～89 ℃ of cuts, gets 3; 3,3-trifluoropropanol 32.7g, yield 88.1%, purity 98%.Two step total recoverys 57.4%.
Embodiment 5
(1) stirs down, 96g methyl alcohol and 60g sodium hydroxide are added in the reactor drum, add 87.5g 2-bromine 3,3 again, the 3-trifluoro propene; Be warming up to 70 ℃, reaction 6h is cooled to room temperature, discharging; Reaction solution is washed three times to neutral with 100g, removes methyl alcohol, Sodium Bromide and sodium hydroxide, obtains 3,3; 3-trifluoro-propenyl methyl ether, 43.9g, yield 69.7%, purity is 98%.
(2) with 43.9g 3,3,3-trifluoro-propenyl methyl ether, the Raney Ni catalyzer that 61.5g ethyl benzoate and 6.5g activation are good adds in the autoclave, and filling hydrogen pressure is 5MPa; Stir down, be warming up to 80 ℃, reaction 6h is cooled to room temperature, shifts out reaction solution; Filtering reacting liquid separates catalyzer with reaction solution, air distillation gained filtrating is collected 87～89 ℃ of cuts, gets 3; 3,3-trifluoropropanol 35.0g, yield 88.1%, purity 98%.Two step total recoverys 61.4%.
Embodiment 6
(1) stir down, with 112g methyl alcohol, 100g sodium hydroxide adds in the reactor drum, adds 128g1 again, 2-two bromo-3; 3,3-trifluoro propane is warming up to 70 ℃, and reaction 6h is cooled to room temperature; Discharging, reaction solution is washed three times to neutral with 100g, removes methyl alcohol, Sodium Bromide and sodium hydroxide, obtains 3,3; 3-trifluoro-propenyl methyl ether, 43.0g, yield 68.2%, purity is 98%.
(2) with 43.0g 3,3,3-trifluoro-propenyl methyl ether, the Raney Ni catalyzer that 64.5g diethyl succinate and 5.2g activation are good adds in the autoclave, and filling hydrogen pressure is 5MPa; Stir down, be warming up to 110 ℃, reaction 6h is cooled to room temperature, shifts out reaction solution; Filtering reacting liquid separates catalyzer with reaction solution, air distillation gained filtrating is collected 87～89 ℃ of cuts, gets 3; 3,3-trifluoropropanol 33.7g, yield 86.7%, purity 98%.Two step total recoverys 59.1%
Embodiment 7
(1) stir down, with 128g methyl alcohol, 48g sodium hydroxide adds in the reactor drum, adds 128g 1 again, 2-two bromo-3; 3,3-trifluoro propane is warming up to 70 ℃, and reaction 6h is cooled to room temperature; Discharging, reaction solution is washed three times to neutral with 100g, removes methyl alcohol, Sodium Bromide and sodium hydroxide, obtains 3,3; 3-trifluoro-propenyl methyl ether, 40.5g, yield 64.3%, purity is 98%.
(2) with 40.5g 3,3,3-trifluoro-propenyl methyl ether, the Raney Ni catalyzer that 77.0g diethylene adipate and 5.3g activation are good adds in the autoclave, and filling hydrogen pressure is 5MPa; Stir down, be warming up to 120 ℃, reaction 6h is cooled to room temperature, shifts out reaction solution; Filtering reacting liquid separates catalyzer with reaction solution, air distillation gained filtrating is collected 87～89 ℃ of cuts, gets 3; 3,3-trifluoropropanol 31.5g, yield 86.0%, purity 98%.Two step total recoverys 55.3%
Embodiment 8
(1) stir down, with 96g methyl alcohol, 48g sodium hydroxide adds in the reactor drum, adds 128g 1 again, 2-two bromo-3; 3,3-trifluoro propane is warming up to 70 ℃, and reaction 6h is cooled to room temperature; Discharging, reaction solution is washed three times to neutral with 100g, removes methyl alcohol, Sodium Bromide and sodium hydroxide, obtains 3,3; 3-trifluoro-propenyl methyl ether, 42.7g, yield 67.7%, purity is 98%.
(2) with 42.7g 3,3,3-trifluoro-propenyl methyl ether, the Raney Ni catalyzer that 72.6g dimethyl phthalate and 5.9g activation are good adds in the autoclave, and filling hydrogen pressure is 5MPa; Stir down, be warming up to 100 ℃, reaction 6h is cooled to room temperature, shifts out reaction solution; Filtering reacting liquid separates catalyzer with reaction solution, air distillation gained filtrating is collected 87～89 ℃ of cuts, gets 3; 3,3-trifluoropropanol 33.7g, yield 87.3%, purity 98%.Two step total recoverys 59.1%
Embodiment 9
(1) stir down, with 80g methyl alcohol, 48g sodium hydroxide adds in the reactor drum, adds 128g 1 again, 2-two bromo-3; 3,3-trifluoro propane is warming up to 70 ℃, and reaction 6h is cooled to room temperature; Discharging, reaction solution is washed three times to neutral with 100g, removes methyl alcohol, Sodium Bromide and sodium hydroxide, obtains 3,3; 3-trifluoro-propenyl methyl ether, 42.8g, yield 67.9%, purity is 98%.
(2) with 42.8g 3,3,3-trifluoro-propenyl methyl ether, the RaneyNi catalyzer that 85.6g gamma-butyrolactone and 6.8g activation are good adds in the autoclave, and filling hydrogen pressure is 5MPa; Stir down, be warming up to 60 ℃, reaction 6h is cooled to room temperature, shifts out reaction solution; Filtering reacting liquid separates catalyzer with reaction solution, air distillation gained filtrating is collected 87～89 ℃ of cuts, gets 3; 3,3-trifluoropropanol 32.0g, yield 82.7%, purity 98%.Two step total recoverys 56.2%
Embodiment 10
(1) stir down, with 112g methyl alcohol, 110g sodium hydroxide adds in the reactor drum, adds 128g1 again, 2-two bromo-3; 3,3-trifluoro propane is warming up to 70 ℃, and reaction 6h is cooled to room temperature; Discharging, reaction solution is washed three times to neutral with 100g, removes methyl alcohol, Sodium Bromide and sodium hydroxide, obtains 3,3; 3-trifluoro-propenyl methyl ether, 41.8g, yield 66.4%, purity is 98%.
(2) with 41.8g 3,3,3-trifluoro-propenyl methyl ether, the RaneyNi catalyzer that 66.9g butylacetate and 8.3g activation are good adds in the autoclave, and filling hydrogen pressure is 5MPa; Stir down, be warming up to 70 ℃, reaction 6h is cooled to room temperature, shifts out reaction solution; Filtering reacting liquid separates catalyzer with reaction solution, air distillation gained filtrating is collected 87～89 ℃ of cuts, gets 3; 3,3-trifluoropropanol 33.0g, yield 87.3%, purity 98%.Two step total recoverys 58.0%
Embodiment 11
(1) stir down, with 128g methyl alcohol, 112g Pottasium Hydroxide adds in the reactor drum, adds 128g1 again, 2-two bromo-3; 3,3-trifluoro propane is warming up to 70 ℃, and reaction 6h is cooled to room temperature; Discharging, reaction solution is washed three times to neutral with 100g, removes methyl alcohol, Sodium Bromide and sodium hydroxide, obtains 3,3; 3-trifluoro-propenyl methyl ether, 40.8g, yield 65.2%, purity is 98%.
(2) with 40.8g 3,3,3-trifluoro-propenyl methyl ether, 53.1g reclaim and use methyl valerate and 4.2g to reclaim in the Raney Ni catalyzer adding autoclave, and filling hydrogen pressure is 5MPa; Stir down, be warming up to 80 ℃, reaction 6h is cooled to room temperature, shifts out reaction solution; Filtering reacting liquid separates catalyzer with reaction solution, air distillation gained filtrating is collected 87～89 ℃ of cuts, gets 3; 3,3-trifluoropropanol 32.3g, yield 87.6%, purity 98%.Two step total recoverys 57.1%
Claims (2)
1. one kind 3,3, the preparation method of 3-trifluoropropanol, this method are with 2-bromine 3,3, and the 3-trifluoro propene is a raw material, comprises the steps:
(1) stir down, methyl alcohol and alkali are joined in the reactor drum, add 2-bromine 3,3 again, the 3-trifluoro propene, heat temperature raising to 70 ℃ reacts 6h, and reaction solution obtains 3,3 through water-washing step, 3-trifluoro-propenyl methyl ether; Wherein the 2-bromine 3,3,3-trifluoro propene: methyl alcohol: the mol ratio of alkali is 1: 3～8: 2.4～6; Described alkali is sodium hydroxide, Pottasium Hydroxide.(2) with 3,3, the Raney Ni catalyzer that 3-trifluoro-propenyl methyl ether, organic ester and activation are good joins in the autoclave, is 5MPa at hydrogen pressure; Stirring heating is warming up to 60 ℃～120 ℃, reaction 4h～8h, and reaction solution is through filtration, distilation steps; Obtain 3,3, the 3-trifluoropropanol; Wherein 3,3,3-trifluoro-propenyl methyl ether: organic ester: the catalyst quality ratio is 1: 1.2～2.0: 0.05～0.2; Described ester is the aliphatic ester of C4～C6 or the aromatic ester of C7～C9.
2. according to claim 13,3, the preparation method of 3-trifluoropropanol comprises the steps:
(1) stirs down, 3 mole, of methanol 96g and 2 molar sodium hydroxide 80g are joined in the reactor drum, add 0.5 mole of 2-bromo-3,3 again, 3-trifluoro propene 87.5g, heat temperature raising to 70 ℃, reaction 6h; Reaction solution obtains 3,3 through water-washing step, 3-trifluoro-propenyl methyl ether.(2) with 44.1g 3,3, the Raney Ni catalyzer that 3-trifluoro-propenyl methyl ether, 61.7g methyl valerate and 5g activation are good joins in the autoclave, and filling hydrogen pressure is 5MPa; Stir down, heat temperature raising to 100 ℃, reaction 6h, reaction solution through filter, distilation steps; Obtain 3,3, the 3-trifluoropropanol.
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115073268A (en) * | 2022-06-30 | 2022-09-20 | 上海瑞合达医药科技有限公司 | 3,3, 3-trifluoropropanol and preparation method thereof |
| CN116514639A (en) * | 2023-03-13 | 2023-08-01 | 北京宇极科技发展有限公司 | Hydrofluoro alkenyl ether, preparation method and application thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN115073268A (en) * | 2022-06-30 | 2022-09-20 | 上海瑞合达医药科技有限公司 | 3,3, 3-trifluoropropanol and preparation method thereof |
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| CN116514639A (en) * | 2023-03-13 | 2023-08-01 | 北京宇极科技发展有限公司 | Hydrofluoro alkenyl ether, preparation method and application thereof |
| CN116514639B (en) * | 2023-03-13 | 2023-10-20 | 北京宇极科技发展有限公司 | Hydrofluoro alkenyl ether, preparation method and application thereof |
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Application publication date: 20121107 |