CN104876791A - Preparation method of 1,1,1,2,2,3,3-heptafluoro-7-bromoheptane - Google Patents

Preparation method of 1,1,1,2,2,3,3-heptafluoro-7-bromoheptane Download PDF

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CN104876791A
CN104876791A CN201510189079.1A CN201510189079A CN104876791A CN 104876791 A CN104876791 A CN 104876791A CN 201510189079 A CN201510189079 A CN 201510189079A CN 104876791 A CN104876791 A CN 104876791A
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dibromobutane
nitrae
isosorbide
propane
preparation
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张超智
王宏明
顾智杰
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SUZHOU JIUWANG NEW MATERIAL RESEARCH AND DEVELOPMENT Co Ltd
SUZHOU JIUWANG ENVIRONMENTAL PROTECTION TECHNOLOGY Co Ltd
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SUZHOU JIUWANG NEW MATERIAL RESEARCH AND DEVELOPMENT Co Ltd
SUZHOU JIUWANG ENVIRONMENTAL PROTECTION TECHNOLOGY Co Ltd
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Abstract

The invention relates to a preparation method of 1,1,1,2,2,3,3-heptafluoro-7-bromoheptane. The method comprises the following steps: adding a tetrahydrofuran solvent to magnesium chips; feeding elemental iodine as an initiator, heating and dropwise adding 1-bromine heptafluoropropane, and heating to prepare a grignard reagent; dropwise adding the prepared grignard reagent to 1,4-dibromobutane and reacting; carrying out reduced pressure distillation to distil out the residual solvent 1,4-dibromobutane; and further washing the produced 1,1,1,2,2,3,3-heptafluoro-7-bromoheptane with boiling water, carrying out reduced pressure distillation, drying in vacuum and purifying. The preparation method is low in cost, high in efficiency, simple in equipment and operation method, and free from pollution to environment.

Description

The preparation method of the fluoro-7-heptyl bromide of a kind of 1,1,1,2,2,3,3-seven
Technical field
The present invention relates to chemical technology field, refer in particular to the preparation method of the fluoro-7-heptyl bromide of a kind of 1,1,1,2,2,3,3-seven.
Background technology
The fluoro-7-heptyl bromide of 1,1,1,2,2,3,3-seven, as conventional organic synthesis intermediate, because making its easier and other intermediates react containing active carbon bromine key, or carries out modification to other resins; Fluorine element electronegativity in molecule is large, and carbon-fluorine bond can be strong, makes the product synthesized have unique various features such as chemical stability, rotproofness, flame retardant resistance, hydro-oleophobicity, didirtresistance; Due to the growth at full speed of China's economy, the fields such as China's chemical industry, building, ocean exploitation and medicine industry are to 1,1,1,2,2, the demand of the fluoro-7-heptyl bromide of 3,3-seven rapidly increases, and does not currently also have disclosed preparation 1,1,1,2,2, the method of the fluoro-7-heptyl bromide of 3,3-seven, but only gordian technique is grasped by external large-lot producer always and is controlled;
1-bromine heptafluoro-propane and Isosorbide-5-Nitrae-dibromobutane are all important organic synthesis raw materials, are wherein liquid under 1-bromine heptafluoro-propane normal temperature, can be used for the aromatic substance of synthesizing perhaloalkyl radical, also can be used as medicine intermediate; Be colourless or weak yellow liquid under Isosorbide-5-Nitrae-dibromobutane normal temperature, for the manufacture of aminophylline, pentoxiverin, monopar etc., for this reason, we have developed a kind of 1,1,1,2,2,3, the preparation method of the fluoro-7-heptyl bromide of 3-seven, cost is low, and efficiency is high, and equipment and working method are simply, environmentally safe.
Summary of the invention
The present invention seeks to the preparation method providing a kind of 1,1,1,2,2,3,3-seven fluoro-7-heptyl bromide in order to overcome the deficiencies in the prior art, cost is low, and efficiency is high, and equipment and working method are simply, environmentally safe.
For achieving the above object, the technical solution used in the present invention is: a kind of 1, 1, 1, 2, 2, 3, the preparation method of the fluoro-7-heptyl bromide of 3-seven, magnesium chips is added in tetrahydrofuran solvent, drop into elemental iodine and make initiator, heat while drip 1-bromine heptafluoro-propane, grignard reagent is prepared in heating, the grignard reagent prepared dropwise is added drop-wise to 1, lower reaction is carried out in 4-dibromobutane, underpressure distillation afterwards steams remaining solvent 1, 4-dibromobutane, produce 1, 1, 1, 2, 2, 3, 3-seven fluoro-7-heptyl bromide washs through further boiling water, underpressure distillation, vacuum-drying, purify.
Preferably, described 1-bromine heptafluoro-propane is 1:3 to 1:5 with the ratio of the dosage of Isosorbide-5-Nitrae-dibromobutane.
Preferably, the temperature of reaction of described grignard reagent and Isosorbide-5-Nitrae-dibromobutane is 20 to 60 to spend.
Preferably, the reaction times of described grignard reagent and Isosorbide-5-Nitrae-dibromobutane is 1 to 3 hours.
Due to the utilization of technique scheme, the present invention compared with prior art has following advantages:
Of the present invention 1,1,1,2, the preparation method of the fluoro-7-heptyl bromide of 2,3,3-seven is prepared into grignard reagent by 1-bromine heptafluoro-propane and magnesium, add Isosorbide-5-Nitrae-dibromobutane again and make 1,1,1,2,2, the fluoro-7-heptyl bromide of 3,3-seven, cost is low, efficiency is high, and equipment and working method are simply, environmentally safe.
Accompanying drawing explanation
Below in conjunction with accompanying drawing, technical solution of the present invention is described further:
Accompanying drawing 1 is the chemical formula of 1-bromine heptafluoro-propane in the preparation method of 1,1,1,2,2,3,3-seven fluoro-7-heptyl bromide of the present invention;
Accompanying drawing 2 is the chemical formula of Isosorbide-5-Nitrae-dibromobutane in the preparation method of 1,1,1,2,2,3,3-seven fluoro-7-heptyl bromide of the present invention;
Accompanying drawing 3 is the chemical formula of 1,1,1,2,2,3,3-seven fluoro-7-heptyl bromide in the preparation method of 1,1,1,2,2,3,3-seven fluoro-7-heptyl bromide of the present invention;
Accompanying drawing 4 is reaction equation in the preparation method of 1,1,1,2,2,3,3-seven fluoro-7-heptyl bromide of the present invention;
Embodiment
Below in conjunction with drawings and the specific embodiments, the present invention is described in further detail.
Accompanying drawing 1-4 is the preparation method of 1,1,1,2,2,3,3-seven fluoro-7-heptyl bromide of the present invention:
Example 1:(optimum reaction condition, temperature of reaction T=40 DEG C)
In three-necked bottle, add magnesium chips 0.24g (0.01mol), tetrahydrofuran (THF) 20ml is as solvent, add two elemental iodines and make initiator, drip 1-bromine heptafluoro-propane 2.49g (0.01mol) under heating condition, reacting by heating afterwards, prepares grignard reagent; Separately get a 250ml four-necked bottle, add Isosorbide-5-Nitrae-dibromobutane 10.80g (0.05mol), thermometer and condensation reflux unit are installed, under temperature of reaction 40 DEG C of conditions, the grignard reagent of preparation are added drop-wise in four-necked bottle, to drip after terminating back flow reaction 2h under 40 DEG C of conditions, be chilled to room temperature after reaction terminates, 100 DEG C of underpressure distillation steam solvent Isosorbide-5-Nitrae-dibromobutane, product is obtained: 1,1,1 after vacuum-drying, 2, the fluoro-7-heptyl bromide of 2,3,3-seven.Claim quality is 3.03g, productive rate (calculating with theoretical yield) is for 96.19%.
Wherein, linked reaction temperature is 40 DEG C, and temperature is too high, has by product and produces, reduce product purity; Temperature of reaction is low, long reaction time, and productive rate is low; Reaction times is 2h, and the time is too short, and react insufficient, productive rate is low; Time is oversize, and productive rate promotes not obvious, loses time and the energy; Grignard reagent is added drop-wise in Isosorbide-5-Nitrae-dibromobutane, and Isosorbide-5-Nitrae-dibromobutane is reactant, is again solvent, so will ensure that Isosorbide-5-Nitrae-dibromobutane is excessive, thus makes C-Br key and the form reagent react of one end in Isosorbide-5-Nitrae-dibromobutane; Isosorbide-5-Nitrae-dibromobutane optimum dosage is five times of 1-bromine heptafluoro-propane, too low, the C-Br key at two ends in Isosorbide-5-Nitrae-dibromobutane can be made all to react, cause by product to increase, affect productive rate, too many raising productive rate DeGrain, and causes the waste of resource.
Example 2-5,1-bromine heptafluoro-propane: Isosorbide-5-Nitrae-dibromobutane=1:5; Temperature of reaction T=40 DEG C
Example 2 3 4 5
1-bromine heptafluoro-propane/g 2.49 2.49 2.49 2.49
Isosorbide-5-Nitrae-dibromobutane/g 10.80 10.80 10.80 10.80
Time/h 1 1.5 2.5 3
Product quality/g 2.94 3.00 3.03 3.02
Productive rate/% 93.33 95.24 96.19 95.87
Example 6-10,1-bromine heptafluoro-propane: Isosorbide-5-Nitrae-dibromobutane=1:5; Temperature of reaction T=20 DEG C
Example 6 7 8 9 10
1-bromine heptafluoro-propane/g 2.49 2.49 2.49 2.49 2.49
Isosorbide-5-Nitrae-dibromobutane/g 10.80 10.80 10.80 10.80 10.80
Time/h 1 1.5 2.0 2.5 3
Product quality/g 2.84 2.90 2.96 2.96 2.97
Productive rate/% 90.16 92.06 93.97 93.97 94.29
Example 11-15,1-bromine heptafluoro-propane: Isosorbide-5-Nitrae-dibromobutane=1:5; Temperature of reaction T=30 DEG C
Example 11 12 13 14 15
1-bromine heptafluoro-propane/g 2.49 2.49 2.49 2.49 2.49
Isosorbide-5-Nitrae-dibromobutane/g 10.80 10.80 10.80 10.80 10.80
Time/h 1 1.5 2.0 2.5 3
Product quality/g 2.91 2.95 2.98 2.99 2.99
Productive rate/% 92.38 93.65 94.60 94.92 94.92
Example 16-20,1-bromine heptafluoro-propane: Isosorbide-5-Nitrae-dibromobutane=1:5; Temperature of reaction T=50 DEG C
Example 16 17 18 19 20
1-bromine heptafluoro-propane/g 2.49 2.49 2.49 2.49 2.49
Isosorbide-5-Nitrae-dibromobutane/g 10.80 10.80 10.80 10.80 10.80
Time/h 1 1.5 2.0 2.5 3
Product quality/g 2.90 2.92 2.94 2.95 2.93
Productive rate/% 92.06 92.70 93.33 93.65 93.02
Example 21-25,1-bromine heptafluoro-propane: Isosorbide-5-Nitrae-dibromobutane=1:5; Temperature of reaction T=60 DEG C
Example 21 22 23 24 25
1-bromine heptafluoro-propane/g 2.49 2.49 2.49 2.49 2.49
Isosorbide-5-Nitrae-dibromobutane/g 10.80 10.80 10.80 10.80 10.80
Time/h 1 1.5 2.0 2.5 3
Product quality/g 2.88 2.90 2.93 2.93 2.92
Productive rate/% 91.43 92.06 93.02 93.02 92.70
Example 26-30,1-bromine heptafluoro-propane: Isosorbide-5-Nitrae-dibromobutane=1:3; Temperature of reaction T=20 DEG C
Example 6 7 8 9 10
1-bromine heptafluoro-propane/g 2.49 2.49 2.49 2.49 2.49
Isosorbide-5-Nitrae-dibromobutane/g 6.48 6.48 6.48 6.48 6.48
Time/h 1 1.5 2.0 2.5 3
Product quality/g 2.01 2.19 2.28 2.27 2.28
Productive rate/% 63.81 69.52 72.38 72.06 72.38
Example 31-35,1-bromine heptafluoro-propane: Isosorbide-5-Nitrae-dibromobutane=1:3; Temperature of reaction T=30 DEG C
Example 6 7 8 9 10
1-bromine heptafluoro-propane/g 2.49 2.49 2.49 2.49 2.49
Isosorbide-5-Nitrae-dibromobutane/g 6.48 6.48 6.48 6.48 6.48
Time/h 1 1.5 2.0 2.5 3
Product quality/g 2.05 2.23 2.30 2.30 2.31
Productive rate/% 65.08 70.79 73.02 73.02 73.33
Example 36-40,1-bromine heptafluoro-propane: Isosorbide-5-Nitrae-dibromobutane=1:3; Temperature of reaction T=40 DEG C
Example 6 7 8 9 10
1-bromine heptafluoro-propane/g 2.49 2.49 2.49 2.49 2.49
Isosorbide-5-Nitrae-dibromobutane/g 6.48 6.48 6.48 6.48 6.48
Time/h 1 1.5 2.0 2.5 3
Product quality/g 2.05 2.26 2.33 2.35 2.33
Productive rate/% 65.08 71.75 73.97 74.60 73.97
Example 41-45,1-bromine heptafluoro-propane: Isosorbide-5-Nitrae-dibromobutane=1:3; Temperature of reaction T=50 DEG C
Example 6 7 8 9 10
1-bromine heptafluoro-propane/g 2.49 2.49 2.49 2.49 2.49
Isosorbide-5-Nitrae-dibromobutane/g 6.48 6.48 6.48 6.48 6.48
Time/h 1 1.5 2.0 2.5 3
Product quality/g 2.04 2.27 2.35 2.35 2.37
Productive rate/% 64.76 72.06 74.60 74.60 75.24
Example 46-50,1-bromine heptafluoro-propane: Isosorbide-5-Nitrae-dibromobutane=1:3; Temperature of reaction T=60 DEG C
Example 6 7 8 9 10
1-bromine heptafluoro-propane/g 2.49 2.49 2.49 2.49 2.49
Isosorbide-5-Nitrae-dibromobutane/g 6.48 6.48 6.48 6.48 6.48
Time/h 1 1.5 2.0 2.5 3
Product quality/g 2.01 2.09 2.14 2.14 2.15
Productive rate/% 63.81 66.35 67.94 67.94 68.25
Example 51-55,1-bromine heptafluoro-propane: Isosorbide-5-Nitrae-dibromobutane=1:4; Temperature of reaction T=20 DEG C
Example 6 7 8 9 10
1-bromine heptafluoro-propane/g 2.49 2.49 2.49 2.49 2.49
Isosorbide-5-Nitrae-dibromobutane/g 8.64 8.64 8.64 8.64 8.64
Time/h 1 1.5 2.0 2.5 3
Product quality/g 2.66 2.71 2.86 2.87 2.87
Productive rate/% 84.44 86.03 90.79 91.11 91.11
Example 56-60,1-bromine heptafluoro-propane: Isosorbide-5-Nitrae-dibromobutane=1:4; Temperature of reaction T=30 DEG C
Example 6 7 8 9 10
1-bromine heptafluoro-propane/g 2.49 2.49 2.49 2.49 2.49
Isosorbide-5-Nitrae-dibromobutane/g 8.64 8.64 8.64 8.64 8.64
Time/h 1 1.5 2.0 2.5 3
Product quality/g 2.69 2.77 2.96 2.97 2.96
Productive rate/% 85.40 87.94 93.97 94.29 93.97
Example 61-65,1-bromine heptafluoro-propane: Isosorbide-5-Nitrae-dibromobutane=1:4; Temperature of reaction T=40 DEG C
Example 6 7 8 9 10
1-bromine heptafluoro-propane/g 2.49 2.49 2.49 2.49 2.49
Isosorbide-5-Nitrae-dibromobutane/g 8.64 8.64 8.64 8.64 8.64
Time/h 1 1.5 2.0 2.5 3
Product quality/g 2.72 2.89 2.99 2.97 2.98
Productive rate/% 86.35 91.75 94.92 94.29 94.60
Example 66-70,1-bromine heptafluoro-propane: Isosorbide-5-Nitrae-dibromobutane=1:4; Temperature of reaction T=50 DEG C
Example 6 7 8 9 10
1-bromine heptafluoro-propane/g 2.49 2.49 2.49 2.49 2.49
Isosorbide-5-Nitrae-dibromobutane/g 8.64 8.64 8.64 8.64 8.64
Time/h 1 1.5 2.0 2.5 3
Product quality/g 2.74 2.90 2.96 2.96 2.97
Productive rate/% 86.98 92.06 93.97 93.97 94.29
Example 71-75,1-bromine heptafluoro-propane: Isosorbide-5-Nitrae-dibromobutane=1:4; Temperature of reaction T=60 DEG C
Example 6 7 8 9 10
1-bromine heptafluoro-propane/g 2.49 2.49 2.49 2.49 2.49
Isosorbide-5-Nitrae-dibromobutane/g 8.64 8.64 8.64 8.64 8.64
Time/h 1 1.5 2.0 2.5 3
Product quality/g 2.67 2.75 2.88 2.89 2.87
Productive rate/% 84.76 87.30 91.43 91.75 91.11
Example 76-80,1-bromine heptafluoro-propane: Isosorbide-5-Nitrae-dibromobutane=1:6; Temperature of reaction T=20 DEG C
Example 6 7 8 9 10
1-bromine heptafluoro-propane/g 2.49 2.49 2.49 2.49 2.49
Isosorbide-5-Nitrae-dibromobutane/g 12.96 12.96 12.96 12.96 12.96
Time/h 1 1.5 2.0 2.5 3
Product quality/g 2.85 2.89 2.96 2.97 2.97
Productive rate/% 90.48 91.75 93.97 94.29 94.29
Example 81-85,1-bromine heptafluoro-propane: Isosorbide-5-Nitrae-dibromobutane=1:6; Temperature of reaction T=30 DEG C
Example 6 7 8 9 10
1-bromine heptafluoro-propane/g 2.49 2.49 2.49 2.49 2.49
Isosorbide-5-Nitrae-dibromobutane/g 12.96 12.96 12.96 12.96 12.96
Time/h 1 1.5 2.0 2.5 3
Product quality/g 2.92 2.94 2.98 2.98 2.97
Productive rate/% 92.70 93.33 94.60 94.60 94.29
Example 86-90,1-bromine heptafluoro-propane: Isosorbide-5-Nitrae-dibromobutane=1:6; Temperature of reaction T=40 DEG C
Example 6 7 8 9 10
1-bromine heptafluoro-propane/g 2.49 2.49 2.49 2.49 2.49
Isosorbide-5-Nitrae-dibromobutane/g 12.96 12.96 12.96 12.96 12.96
Time/h 1 1.5 2.0 2.5 3
Product quality/g 2.97 2.99 3.02 3.03 3.03
Productive rate/% 94.29 94.92 95.87 96.19 96.19
Example 91-95,1-bromine heptafluoro-propane: Isosorbide-5-Nitrae-dibromobutane=1:6; Temperature of reaction T=50 DEG C
Example 6 7 8 9 10
1-bromine heptafluoro-propane/g 2.49 2.49 2.49 2.49 2.49
Isosorbide-5-Nitrae-dibromobutane/g 12.96 12.96 12.96 12.96 12.96
Time/h 1 1.5 2.0 2.5 3
Product quality/g 2.91 2.91 2.95 2.93 2.95
Productive rate/% 92.38 92.38 93.65 93.02 93.65
Example 96-100,1-bromine heptafluoro-propane: Isosorbide-5-Nitrae-dibromobutane=1:6; Temperature of reaction T=60 DEG C
Example 6 7 8 9 10
1-bromine heptafluoro-propane/g 2.49 2.49 2.49 2.49 2.49
Isosorbide-5-Nitrae-dibromobutane/g 12.96 12.96 12.96 12.96 12.96
Time/h 1 1.5 2.0 2.5 3
Product quality/g 2.86 2.90 2.94 2.93 2.92
Productive rate/% 90.79 92.06 93.33 93.02 92.70
Due to the utilization of technique scheme, the present invention compared with prior art has following advantages:
Of the present invention 1,1,1,2, the preparation method of the fluoro-7-heptyl bromide of 2,3,3-seven is prepared into grignard reagent by 1-bromine heptafluoro-propane and magnesium, add Isosorbide-5-Nitrae-dibromobutane again and make 1,1,1,2,2, the fluoro-7-heptyl bromide of 3,3-seven, cost is low, efficiency is high, and equipment and working method are simply, environmentally safe.
Below be only embody rule example of the present invention, protection scope of the present invention is not constituted any limitation.The technical scheme that all employing equivalents or equivalence are replaced and formed, all drops within rights protection scope of the present invention.

Claims (4)

1. one kind 1,1,1,2,2,3, the preparation method of the fluoro-7-heptyl bromide of 3-seven, it is characterized in that: magnesium chips is added in tetrahydrofuran solvent, drop into elemental iodine and make initiator, heat and drip 1-bromine heptafluoro-propane, grignard reagent is prepared in heating, dropwise be added drop-wise in Isosorbide-5-Nitrae-dibromobutane by the grignard reagent prepared and carry out lower reaction, underpressure distillation afterwards steams remaining solvent 1,4-dibromobutane, produce 1,1,1,2,2,3,3-seven fluoro-7-heptyl bromide washs through further boiling water, underpressure distillation, vacuum-drying, purification.
2. the preparation method of 1,1,1,2,2,3,3-seven fluoro-7-heptyl bromide according to claim 1, is characterized in that: described 1-bromine heptafluoro-propane is 1:3 to 1:5 with the ratio of the dosage of Isosorbide-5-Nitrae-dibromobutane.
3. the preparation method of 1,1,1,2,2,3,3-seven fluoro-7-heptyl bromide according to claim 1, is characterized in that: the temperature of reaction of described grignard reagent and Isosorbide-5-Nitrae-dibromobutane is 20 to 60 to spend.
4. the preparation method of 1,1,1,2,2,3,3-seven fluoro-7-heptyl bromide according to claim 1, is characterized in that: the reaction times of described grignard reagent and Isosorbide-5-Nitrae-dibromobutane is 1 to 3 hours.
CN201510189079.1A 2015-04-21 2015-04-21 Preparation method of 1,1,1,2,2,3,3-heptafluoro-7-bromoheptane Pending CN104876791A (en)

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Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101696153A (en) * 2009-10-23 2010-04-21 济南大学 Preparation method of 3,3-dimethyl-1-butanol

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101696153A (en) * 2009-10-23 2010-04-21 济南大学 Preparation method of 3,3-dimethyl-1-butanol

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
D.D.DENSON ET AL: "SYNTHESIS OF PERFLUOROALIPHATIC GRIGNARD REAGENTS", 《JOURNAL OF FLUORINE CHEMISTRY》 *

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Application publication date: 20150902