CN105130752A - Preparation method of 1,1,1,3,3,3-hexafluoro-2-(4-styrene)propanol - Google Patents
Preparation method of 1,1,1,3,3,3-hexafluoro-2-(4-styrene)propanol Download PDFInfo
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- CN105130752A CN105130752A CN201510508250.0A CN201510508250A CN105130752A CN 105130752 A CN105130752 A CN 105130752A CN 201510508250 A CN201510508250 A CN 201510508250A CN 105130752 A CN105130752 A CN 105130752A
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- vinylbenzene
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/64—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by simultaneous introduction of -OH groups and halogens
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Abstract
The invention discloses a preparation method of 1,1,1,3,3,3-hexafluoro-2-(4-styrene)propanol. According to the preparation method, phenylethenyl magnesium chloride Grignard reagent is reacted with hexafluoroacetone at a low temperature, and an obtained product is subjected to washing and refining so as to obtain a finished product with a content of 99.0% or higher. Cheaper raw materials are adopted in the preparation method, the raw materials are safer for storage, transportation, and using, and requirement on operator protection and equipment is low; the preparation method is more reasonable, safe, simple, low in energy consumption, high in yield, and low in environmental pollution; the finished product is a high-activity organic intermediate with a fluorine double bond structure, augmented products of the finished product are more, application range is extremely wide, and market prospect is promising; an obtained three wastes byproduct is magnesium chloride which is an excellent flame-resistant material in the field of building material, and can be recycled; and three wastes processing of chlorine-containing waste water is convenient, and less pollution on the environment is caused.
Description
Technical field
The present invention relates to the synthesis intermediates such as a kind of medicine, agricultural chemicals, rubber, be specifically related to a kind of preparation technology of 1,1,1,3,3,3-hexafluoro-2-(4-vinylbenzene) propyl alcohol.
Background technology
At present, the preparation of 1,1,1,3,3,3-hexafluoro-2-(4-vinylbenzene) propyl alcohol, what generally adopt is that vinylbenzene magnesium bromide and Perfluoroacetone carry out producing as raw material, and its shortcoming is: the prices of raw and semifnished materials are expensive; Difficulty is larger using, when storing for Perfluoroacetone, to the protection of operator and equipment requirements also higher, Perfluoroacetone still belongs to 2.3 class toxic gases, and toxic hazard is large; Also the bad process such as the three wastes by product magnesium bromide of final generation, brominated waste water are large to environmental influence.
Summary of the invention
The object of the present invention is to provide a kind of 1,1,1, the preparation technology of 3,3,3-hexafluoro-2-(4-vinylbenzene) propyl alcohol, present invention employs more cheap raw material, and the raw material more easily storage of safety, transport and use, to the protection of operator and equipment requirements also low; Present invention process more rationally, safely, simple, energy consumption is low, yield is high, environmental pollution is little; The finished product of the present invention are high reactivity organic intermediates of fluorine-containing double bond structure, and its extension product is more, and widely, market outlook are fine for Application Areas; The three wastes by-product magnesium chloride of final generation is also good fire retardant material in material of construction, can recycling; Chlorine-contained wastewater is also compare easy to handle on three-protection design, and environmental pollution is little.
For achieving the above object, technical scheme of the present invention is the preparation technology of a kind of 1,1,1,3,3,3-hexafluoro of design-2-(4-vinylbenzene) propyl alcohol, comprises the steps:
214.5 mass parts three hydration Perfluoroacetones are generated Perfluoroacetone gas through 500 mass parts 98% sulfuric acid processed;
Perfluoroacetone gas is chilled to-5 ~ 5 DEG C in advance, synthesis under normal pressure is carried out at-20 ~-40 DEG C again with 500 mass parts vinylbenzene chloride Grignard reagents, tail gas imports Water spray and absorbs, ventilation terminates sampling analysis GC, control reaction end, to reach home back balance 30 minutes (interior temperature does not control), crude product 622.8 mass parts obtained;
Cancellation is carried out again with 1000 mass parts 1mol/l sulfuric acid, temperature is made to be no more than 30 DEG C, isolated oil reservoir 600 mass parts saturated aqueous common salts clean, isolated oil reservoir 35 mass parts anhydrous magnesium sulfate dryings, filtration again, to carry out rectifying with rotatory evaporator and finally obtains content product 147.6 mass parts (yield 84%) of (GC detection) more than 99% by crude product.
Preferably, proportion >=1.59 of described three hydration Perfluoroacetones.
Preferably, the temperature of described processed controls at 110 ~ 135 DEG C.
Preferably, control sulfuric acid concentration in described dehydration process and be not less than 85%.
Preferably, the concentration of described vinylbenzene chloride Grignard reagents is 1.3 ~ 1.5mol/kg.
Advantage of the present invention and beneficial effect are: provide a kind of 1,1,1,3, the preparation technology of 3,3-hexafluoro-2-(4-vinylbenzene) propyl alcohol, present invention employs more cheap raw material, and the raw material more easily storage of safety, transport and use, to the protection of operator and equipment requirements also low; Present invention process more rationally, safely, simple, energy consumption is low, yield is high, environmental pollution is little; The finished product of the present invention are high reactivity organic intermediates of fluorine-containing double bond structure, and its extension product is more, and widely, market outlook are fine for Application Areas; The three wastes by-product magnesium chloride of final generation is also good fire retardant material in material of construction, can recycling; Chlorine-contained wastewater is also compare easy to handle on three-protection design, and environmental pollution is little.
Accompanying drawing explanation
Fig. 1 is the chemical equation that the present invention prepares 1,1,1,3,3,3-hexafluoro-2-(4-vinylbenzene) propyl alcohol.
Embodiment
Below in conjunction with drawings and Examples, the specific embodiment of the present invention is further described.Following examples only for technical scheme of the present invention is clearly described, and can not limit the scope of the invention with this.
The technical scheme that the present invention specifically implements is:
A kind of preparation technology of 1,1,1,3,3,3-hexafluoro-2-(4-vinylbenzene) propyl alcohol, comprises the steps:
214.5 gram of three hydration Perfluoroacetone (proportion >=1.59) is generated Perfluoroacetone gas through 500 gram of 98% sulfuric acid (constant temperature 110 ~ 135 degree) processed (control sulfuric acid concentration and be not less than 85%);
Perfluoroacetone gas is chilled to-5 ~ 5 DEG C in advance, synthesis under normal pressure is carried out at-20 ~-40 DEG C again with 500 grams of vinylbenzene chloride Grignard reagents (concentration: 1.3 ~ 1.5mol/kg), tail gas imports Water spray and absorbs, ventilation terminates sampling analysis GC, control reaction end, to reach home back balance 30 minutes (interior temperature does not control), the crude product obtained 622.8 grams;
Cancellation is carried out with 1000 grams of 1mol/l sulfuric acid, temperature is made to be no more than 30 DEG C, isolated oil reservoir cleans with 600 grams of saturated aqueous common salts (sodium-chlor), isolated oil reservoir 35 grams of anhydrous magnesium sulfate dryings, filtration again, to carry out rectifying with rotatory evaporator and finally obtains content product 147.6 grams (yield 84%) of (GC detection) more than 99% by crude product.
The present invention prepares the chemical equation of 1,1,1,3,3,3-hexafluoro-2-(4-vinylbenzene) propyl alcohol as shown in Figure 1.
The above is only the preferred embodiment of the present invention; it should be pointed out that for those skilled in the art, under the prerequisite not departing from the technology of the present invention principle; can also make some improvements and modifications, these improvements and modifications also should be considered as protection scope of the present invention.
Claims (5)
1. the preparation technology of hexafluoro-2-(4-vinylbenzene) propyl alcohol, is characterized in that, comprise the steps:
214.5 mass parts three hydration Perfluoroacetones are generated Perfluoroacetone gas through 500 mass parts 98% sulfuric acid processed;
Perfluoroacetone gas is chilled to-5 ~ 5 DEG C in advance, synthesis under normal pressure is carried out at-20 ~-40 DEG C again with 500 mass parts vinylbenzene chloride Grignard reagents, tail gas imports Water spray and absorbs, ventilation terminates sampling analysis GC, control reaction end, to reach home back balance 30 minutes, crude product 622.8 mass parts obtained;
Cancellation is carried out again with 1000 mass parts 1mol/l sulfuric acid, temperature is made to be no more than 30 DEG C, isolated oil reservoir 600 mass parts saturated aqueous common salts clean, isolated oil reservoir 35 mass parts anhydrous magnesium sulfate dryings, filtration again, carries out rectifying with rotatory evaporator by crude product and finally obtains product 147.6 mass parts of content more than 99%.
2. the preparation technology of 1,1,1,3,3,3-hexafluoro-2-(4-vinylbenzene) propyl alcohol according to claim 1, is characterized in that, proportion >=1.59 of described three hydration Perfluoroacetones.
3. the preparation technology of 1,1,1,3,3,3-hexafluoro-2-(4-vinylbenzene) propyl alcohol according to claim 1 and 2, it is characterized in that, the temperature of described processed controls at 110 ~ 135 DEG C.
4. the preparation technology of 1,1,1,3,3,3-hexafluoro-2-(4-vinylbenzene) propyl alcohol according to claim 3, is characterized in that, control sulfuric acid concentration and be not less than 85% in described dehydration process.
5. the preparation technology of 1,1,1,3,3,3-hexafluoro-2-(4-vinylbenzene) propyl alcohol according to claim 4, it is characterized in that, the concentration of described vinylbenzene chloride Grignard reagents is 1.3 ~ 1.5mol/kg.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510508250.0A CN105130752A (en) | 2015-08-18 | 2015-08-18 | Preparation method of 1,1,1,3,3,3-hexafluoro-2-(4-styrene)propanol |
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| CN201510508250.0A CN105130752A (en) | 2015-08-18 | 2015-08-18 | Preparation method of 1,1,1,3,3,3-hexafluoro-2-(4-styrene)propanol |
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| CN201510508250.0A Pending CN105130752A (en) | 2015-08-18 | 2015-08-18 | Preparation method of 1,1,1,3,3,3-hexafluoro-2-(4-styrene)propanol |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106565418A (en) * | 2016-11-14 | 2017-04-19 | 河南工业大学 | Preparation method of 1,1,1,3,3-hexafluoro-2-(4-vinylphenyl)-2-propanol |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002069043A2 (en) * | 2001-02-23 | 2002-09-06 | Massachusetts Institute Of Technology | Low absorbing resists for 157 nm lithography |
| US20020155376A1 (en) * | 2000-09-11 | 2002-10-24 | Kazuhiko Hashimoto | Positive resist composition |
| CN1762952A (en) * | 2005-11-07 | 2006-04-26 | 上海三爱富新材料股份有限公司 | Hexafluoroacetone hydrate dehydrolyzing method |
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2015
- 2015-08-18 CN CN201510508250.0A patent/CN105130752A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20020155376A1 (en) * | 2000-09-11 | 2002-10-24 | Kazuhiko Hashimoto | Positive resist composition |
| WO2002069043A2 (en) * | 2001-02-23 | 2002-09-06 | Massachusetts Institute Of Technology | Low absorbing resists for 157 nm lithography |
| CN1762952A (en) * | 2005-11-07 | 2006-04-26 | 上海三爱富新材料股份有限公司 | Hexafluoroacetone hydrate dehydrolyzing method |
Non-Patent Citations (2)
| Title |
|---|
| DANIEL S. HALL，ET AL.: "Dissolution behavior of fluoroalcohol substituted polystyrenes", 《PROCEEDINGS OF SPIE-THE INTERNATIONAL SOCIETY FOR OPTICAL ENGINEERING》 * |
| MIETHCHEN, RALF，ET AL.: "Direct ketalisation of vic-diols with hexafluoroacetone. Conversion of D-glucose and L-rhamnose derivatives to hexafluoroacetone ketals", 《TETRAHEDRON》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106565418A (en) * | 2016-11-14 | 2017-04-19 | 河南工业大学 | Preparation method of 1,1,1,3,3-hexafluoro-2-(4-vinylphenyl)-2-propanol |
| CN106565418B (en) * | 2016-11-14 | 2020-02-14 | 河南工业大学 | Preparation method of 1,1,1,3,3, 3-hexafluoro-2- (4-vinyl phenyl) -2-propanol |
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Application publication date: 20151209 |