TWI247734B - Purified fluoroalcohol - Google Patents
Purified fluoroalcohol Download PDFInfo
- Publication number
- TWI247734B TWI247734B TW093132813A TW93132813A TWI247734B TW I247734 B TWI247734 B TW I247734B TW 093132813 A TW093132813 A TW 093132813A TW 93132813 A TW93132813 A TW 93132813A TW I247734 B TWI247734 B TW I247734B
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- Prior art keywords
- fluoroalcohol
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- AQYSYJUIMQTRMV-UHFFFAOYSA-N hypofluorous acid Chemical compound FO AQYSYJUIMQTRMV-UHFFFAOYSA-N 0.000 title claims abstract description 28
- 238000001704 evaporation Methods 0.000 claims description 17
- 230000008020 evaporation Effects 0.000 claims description 17
- 238000004519 manufacturing process Methods 0.000 claims description 11
- 239000000758 substrate Substances 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 3
- 238000002347 injection Methods 0.000 claims description 3
- 239000007924 injection Substances 0.000 claims description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract description 39
- 238000000034 method Methods 0.000 abstract description 14
- 150000003254 radicals Chemical class 0.000 abstract description 10
- 239000011541 reaction mixture Substances 0.000 abstract description 6
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 abstract description 6
- 238000004821 distillation Methods 0.000 abstract description 4
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical group FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 abstract description 3
- 238000002835 absorbance Methods 0.000 description 9
- 239000010410 layer Substances 0.000 description 9
- 239000007789 gas Substances 0.000 description 7
- 239000012535 impurity Substances 0.000 description 7
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- -1 alkali metal alkoxide Chemical class 0.000 description 5
- 239000003999 initiator Substances 0.000 description 5
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 239000000049 pigment Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229930182558 Sterol Natural products 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 150000003432 sterols Chemical class 0.000 description 3
- 235000003702 sterols Nutrition 0.000 description 3
- NBUKAOOFKZFCGD-UHFFFAOYSA-N 2,2,3,3-tetrafluoropropan-1-ol Chemical compound OCC(F)(F)C(F)F NBUKAOOFKZFCGD-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 150000004703 alkoxides Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 125000005739 1,1,2,2-tetrafluoroethanediyl group Chemical group FC(F)([*:1])C(F)(F)[*:2] 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- PAOHAQSLJSMLAT-UHFFFAOYSA-N 1-butylperoxybutane Chemical compound CCCCOOCCCC PAOHAQSLJSMLAT-UHFFFAOYSA-N 0.000 description 1
- LARHPWJUFVCDON-UHFFFAOYSA-N 1-butylperoxybutane;propan-2-yl hydrogen carbonate Chemical compound CC(C)OC(O)=O.CCCCOOCCCC LARHPWJUFVCDON-UHFFFAOYSA-N 0.000 description 1
- SZVMZLJAAGWNPG-UHFFFAOYSA-N 1-tert-butylperoxyoctane Chemical compound CCCCCCCCOOC(C)(C)C SZVMZLJAAGWNPG-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- OEIJRRGCTVHYTH-UHFFFAOYSA-N Favan-3-ol Chemical compound OC1CC2=CC=CC=C2OC1C1=CC=CC=C1 OEIJRRGCTVHYTH-UHFFFAOYSA-N 0.000 description 1
- CITFYDYEWQIEPX-UHFFFAOYSA-N Flavanol Natural products O1C2=CC(OCC=C(C)C)=CC(O)=C2C(=O)C(O)C1C1=CC=C(O)C=C1 CITFYDYEWQIEPX-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 235000006040 Prunus persica var persica Nutrition 0.000 description 1
- 240000006413 Prunus persica var. persica Species 0.000 description 1
- 101100067761 Rattus norvegicus Gast gene Proteins 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- AYJRCSIUFZENHW-DEQYMQKBSA-L barium(2+);oxomethanediolate Chemical compound [Ba+2].[O-][14C]([O-])=O AYJRCSIUFZENHW-DEQYMQKBSA-L 0.000 description 1
- XKLVLDXNZDIDKQ-UHFFFAOYSA-N butylhydrazine Chemical compound CCCCNN XKLVLDXNZDIDKQ-UHFFFAOYSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 210000000078 claw Anatomy 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 235000011987 flavanols Nutrition 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910052746 lanthanum Inorganic materials 0.000 description 1
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 108091008695 photoreceptors Proteins 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 1
- 229910052939 potassium sulfate Inorganic materials 0.000 description 1
- 239000001120 potassium sulphate Substances 0.000 description 1
- 235000011151 potassium sulphates Nutrition 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000012465 retentate Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- HUAUNKAZQWMVFY-UHFFFAOYSA-M sodium;oxocalcium;hydroxide Chemical compound [OH-].[Na+].[Ca]=O HUAUNKAZQWMVFY-UHFFFAOYSA-M 0.000 description 1
- RCOSUMRTSQULBK-UHFFFAOYSA-N sodium;propan-1-olate Chemical compound [Na+].CCC[O-] RCOSUMRTSQULBK-UHFFFAOYSA-N 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
Classifications
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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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/34—Halogenated alcohols
- C07C31/38—Halogenated alcohols containing only fluorine as halogen
-
- 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
- C07C29/44—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by addition reactions, i.e. reactions involving at least one carbon-to-carbon double or triple bond
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12C—BEER; PREPARATION OF BEER BY FERMENTATION; PREPARATION OF MALT FOR MAKING BEER; PREPARATION OF HOPS FOR MAKING BEER
- C12C11/00—Fermentation processes for beer
- C12C11/02—Pitching yeast
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- G—PHYSICS
- G11—INFORMATION STORAGE
- G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
- G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
- G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
- G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
- G11B7/242—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers
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- G—PHYSICS
- G11—INFORMATION STORAGE
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- G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
- G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
- G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
- G11B7/242—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers
- G11B7/244—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only
- G11B7/246—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing dyes
-
- G—PHYSICS
- G11—INFORMATION STORAGE
- G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
- G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
- G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
- G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
- G11B7/242—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers
- G11B7/244—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only
- G11B7/246—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing dyes
- G11B7/247—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing dyes methine or polymethine dyes
- G11B7/2472—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing dyes methine or polymethine dyes cyanine
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- G—PHYSICS
- G11—INFORMATION STORAGE
- G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
- G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
- G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
- G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
- G11B7/242—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers
- G11B7/244—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only
- G11B7/246—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing dyes
- G11B7/248—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing dyes porphines; azaporphines, e.g. phthalocyanines
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- G—PHYSICS
- G11—INFORMATION STORAGE
- G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
- G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
- G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
- G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
- G11B7/242—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers
- G11B7/244—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only
- G11B7/249—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing organometallic compounds
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- G—PHYSICS
- G11—INFORMATION STORAGE
- G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
- G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
- G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
- G11B7/26—Apparatus or processes specially adapted for the manufacture of record carriers
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- Chemical & Material Sciences (AREA)
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- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Food Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Microbiology (AREA)
- Mycology (AREA)
- Genetics & Genomics (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Optical Record Carriers And Manufacture Thereof (AREA)
- Thermal Transfer Or Thermal Recording In General (AREA)
Description
1247734 九、發明說明： 【發明所屬之技術領域】 本發明係關於一般式(1) H(CFRiCF2)nCH2OH (1) 〔η二1時氏表示F或CF3，表示F〕所表示之 氟醇之製造方法，特別是關於在實質上不含不純物之氟醇及 其基板上設置可用雷射書寫或讀取資訊之記錄層的資訊記錄 媒體製造用的用途。 ' 【先前技術】 H(CF2CF2)nCH2〇H(n=l、2)之製造法，有如特開昭 54-154707號公報及美國專利第2559628號所記載者般，係藉 由使曱醇與四氟合乙烯在有t-丁辛基過氧化物之存在下產生 反應’而付到H(CFzCF2)nCH2〇H(n最南為12)之調聚物(telomer) 混合物。 惟，將以前述方法所得之調聚物混合物以蒸餾之方法精 製時，因仍有數百ppm程度之蒸發殘份無法除去，例如作為 於CD-R或DVD-R等之基板上設有以雷射等寫入及讀出資訊 用之記錄層的資訊媒體製造時之溶劑使用時，因蒸發殘份的 影響’有不適於製作高品質之資訊記錄媒體之缺點。 本發明之目的在於提供實質上不含蒸發殘份及uv吸收 成份等之不純物之一般式(1) H(CFR1CF2)nCH2OH (1) 〔式中n、R!係如前之定義者〕所表示之氟醇之製 造方法’及利用该氟醇在基板上設置雷射可寫入及讀取之記 錄層之作為資訊記錄媒體製造用溶劑之用途，及利用該氣醇 所製造之基板上設置雷射可寫入及讀取之記錄層所成之資訊 記錄媒體者。 1247734 【發明内容】 士發明係有關於下述第1項至第20項。 項一種氟醇之純化方法，其係使甲醇、四氟合乙 稀f/、氟合丙稀在有自由基產生源之情形下產生反應，而製 造出下式(1)所表示之氟醇， H(CFR1CF2)nCH2OH ⑴ 〔11一1時以1表示卩或[卩3，11=2時1^1表示|7〕 其特欲為··具有將反應液在有鹼之存在下實行蒗餾， 使反^液與鹼接觸之後蒸餾之工程。 .....〆 係為^^員。如第1項之氟醇之純化方法，其中前述驗之pKb 如第1項或第2項之氣醇之純化方法，其中前述 鹼為鹼金屬醇鹽或鹼金屬氫氧化物者。 务，至P項之任—者所述之_之純化方 :選=醇鹽、氣氧化納或氣氧化卸之群體中 法，^ϊίίΓ之任一者所述之氣醇之純化方 H(CFR1CF2)nCH2〇H ⑴ 殘份為〔ilij細叙絲者〕所麵之_中之蒸發 第6項如第5項所述之氟醇之純化 H(CFR1CF2)nCH2OH (1) 。〒式(1) 之蒸發 殘份為25ppm以下 係如前之定義者〕所絲之氟醇中. 〔式中n、R〗係如前之定義者〕所表示 殘份為lOppm以下。 弗匕 醇中之蒸 發 1247734 、、#·,甘第 =、如第1項〜第7項之任一者所述之氟醇之純化方 #、’心中d自由基產生麟由反賴始劑、uv及熱三者中 所忠出之至少一種。 h第9項如第8項所述之氟醇之純化方法，其中前述自由 土產生〃源係反應溫度巾之半減__小時之反應開始劑。 第10項如第8項或第9項所述之氟醇之純化方法，其中 月’J述自由基產生源為過氧化物。 第11項如第8項所述之氟醇之純化方法，其中前述自由 基產生源為高丁基D、高丁基j或高丁基〇。 =2項如第1項至第5項之任一者所述之氟醇之純化方 去，其係一併使用自由基產生源與受酸劑。 苐項種氟醇’其係以蒸發殘份為50ppm以下之下述 式⑴表示： H(CFR1CF2)nCH2OH (1) —〔η二1時1表示F或CF3，的時!^表示F〕。 第14項如第13項所述之氟醇，其蒸發殘份為25PPm以 下。 第15項如第13項或第14項所述之氣醇，其蒸發殘 lOppm以下。 第16項如第13項至第15項之任一者所述之氣醇，苴在 甲醇中之吸光度(190〜30〇nm)為〇.2abs以下。 、 >第17項如第13項至第16項之任—者所述之氟醇，其在 甲醇中之吸光度(205nm)為(Xiabs以下。 第18項如第17項所述之氟醇，其在曱醇中之吸光度 (205nm)為-0.2abs。 第19項-種資訊記錄媒體之製造方法，係於_項至 第18項之任-者所述之氟醇所製成之基板上設置可用雷射 入及/或讀取資訊之記錄層。 ” 第20項一種資訊記錄媒體，係於以第i項至第12項之任 7 1247734 一者所述之方法所製造之以下式表示之氟醇， H(CFR1CF2)nCH2OH (1) 〔11=1時&1表示？或0?3，11=2時尺1表示？〕 或於以第13項至第18項之任一者所述之以下式表示之 氟醇 H(CFR1CF2)nCH2OH (1) 〔11=1時以1表示卩或€?3，11=2時111表示？〕 所製成之基板上，設置可用雷射寫入及/或讀取資訊之記 錄層。 曰本發明之製造法中，係對四氟合乙烯或六氟合丙稀使用 過$之甲醇。反應溫度為4〇〜140°C左右，反應時間為3〜12小 日守左右/反應壓力為〇·2〜i.2Mpa左右。反應例如可用高壓反 應锅進行。反應系内以氮氣或氬氣等惰性氣體加以置換較佳。 反應終了後，依須要將過多之曱醇蒸餾除去，可於有鹼 存在之情形下實行。又，於反應混合物中含有 H(CF2CF2)nCH2OH(n^ 3 ^ Ji) ^H(CF(CF3)CF2)nCH2OH(n^ 2 以上)之不純物時，藉由蒸館之方法將之事絲去較佳。 —条館為將包含有H(CFRlCF2)nCH2〇H〔n、化為如前述 軸反應混合物，在有齡在之情形下， ΐί3應ί合物與驗接觸之後實行。加人反應混合物中， i鹼則;ί =可舉出PKb為2以下之驗。 趨女甲％納、乙醇鈉、丙醇鈉、鉀t·丁醇金屬 =等屬醇鹽’或氫氧化鈉、氳氧化鉀或氫氧 ι μ 氣氧化物，或氫氧化詞、氳氧化铭、氫氧化 二物^之灰等。每1公斤重量的曱醇以外之反應混 ^。α之使用1為_〜〗.〇莫耳左右，最佳桃卜⑽莫耳左 哮r i乍上ϋ’1-’可ΐ出碳酸詞、破酸鎂、碳酸納、礙酸鉀、 火-义η反·喊鉀等之驗金屬，或驗土類金屬之礙酸鹽及 1247734 碳酸氫鹽、，化鈣、氫氧化鈣、鹼石灰或碳酸鋇等。受酸劑 以不使反應系成為強驗性，及可將反應時所產生 ^ 以捕集者較佳。 ^卞 ，酸劑^使用量並無特別之限定，每一莫耳四氟合乙 或/、氣合丙細使用0.001〜〇1莫耳左右即可。 作為自由基產生源，可使用自反應開始劑、爪及 構成之群體中所選出之至少一種。當自由基產生源為清時， 例如可使用中壓或咼壓水銀燈所產生之UV。當自由基產生源 為熱時，例如可為250〜300°C之溫度。而作為反應開始劑可例、 示過氧化物，較佳者可例舉反應溫度中之半減期為約1〇 之反應開始劑。 、 較佳之自由基產生源可例舉出高丁基D(雙+丁基過氧 化物)〃、高丁基o(t-丁基過氧化物_2_乙基己醇)或高丁基1(1_丁 费過氧化物異丙基碳酸脂）。反應開始劑之使用量通常為每一 莫耳四氟合乙烯或六氟合丙烯使用0.005〜0.1莫耳左右。 本务明所仔之氟醇之蒸發殘份為50ppm以下，較佳為 25ppm以下’更佳為lOppm以下。 。蒸發殘份可利用下述之方式求得。亦即，測量氟醇之在 4(TC及以5mmHg濃縮時之殘份之重量，並以相對於 HCF2CF2CH2OH 的 wt.ppm表示。 本發明所得之以一般式(1)所表示之氟醇22〇5nm中之 在甲醇中之吸光度為〇 labS以下，較佳為以下，更佳為 -〇.2abs以下。甲醇中之吸光度係以在一般式⑴之氣醇imi中、 加入甲醇3ml所成之物品為測量試料。作為參考者係使用甲醇 作測量。 女含本+發明之氟醇，所謂「實質上不含不純物」者，係指① 氟醇之蒸發殘份為5〇PPm以下，較佳為25ppm以下，更佳為 10ppm以下；及/或(ϋ)在甲醇中之吸光度(205nm)為 O.labs以下，較佳為-〇.labs以下，更佳為_〇.2油5以下。 1247734 而於基板上設置可官 μ 資訊記錄髓，胁胃㈣訊之記闕所成之 包含該氟醇之⑽、溶針=()之_的溶劑，較佳為於 記錄層。前述色素;以含有色素之 金翁系色素、硫代呢喃全夸手' tt敵菁系色素、咖南 烧系色素、苯酮系色音、知狀輪糸色素、三苯甲 金屬錯鹽系色素等。色謀里烏姆系色素及 =性及提高接著力及防止i錄間可= 至層，而於s己錄層上設置保護層亦可。 - 、巧本f明’可容易地製造出於基板上設有可用雷射寫人 及/或讀取資訊之記錄層的資訊記錄媒體(CD_R、dvd_r&之 光碟片等)及軟片等之感光體之製造所適用的實質上不含有 不純物之 hcf2cf2ch2oh、h(cf2cf2)2ch2oh 及 hcf(cf3)cf2ch2oh。 【實施方式】 以下使用實施例詳細說明本發明。 實施例1 於高壓反應鍋中送入甲醇(2L)、高丁基D(45g)及碳酸詞 (3〇g)。將反應鋼以鼠氣置換後’以初期速度6〇〇g/hr送入四氧 合乙烯，控制至溫度125°C及壓力0.8Mpa，使反應六小時。將 反應混合物冷卻後蒸餾，分離甲醇，接著分離 H(CF2CF2)nCH2OH(n為2以上之整數)，即得到HCF2CF2CH2OH 之存留物(1.2L)。所得到之HCF2CF2CH2OH之存留份之蒸發殘 份為600ppm左右，吸光度(205nm)為2.0abs。又，以毛細管 1247734 GC/MASS分析時，發現混合有曱醛、HCF2CF2CHO、 hcf2chfcho 、 hcf2cf2cf2cho 、 HCF2COOCH2CH=CHCHO、HCF2CH2COOCH=CHCHO 及 HCF2CF2CH(OH)OCH2CHO等之各種醛類成份。 將上述存留份反覆蒸餾時，此等不純物之含量、蒸發殘 存份量及吸光度(205nm)等幾不變化。 對所得之HCF2CF2CH2〇H之存留份(1L)加入28%甲醇納 (30g)，於加熱下實施蒸餾，即得到實質上不含不純物之 HCF2CF2CH2〇H。所得到的HCF2CF2CH2〇H之蒸發殘份為 lOppm以下，吸光度(2〇5nm)為-0.2abs以下。又，上述醛類成 份為GC/MASS之檢知界限以下。 以下揭示GC/MASS之分析條件。 胃 1) 管柱(column):液相 DB-1301 膜厚：1.00/zm 管柱尺寸：60mx0.247mm 2) 分析條件 載體He : 200kPa 空氣：40kPa H2 · 50kPa 溫度：50°C(5分)〜220°C15分(以15°C/分昇溫） 喷射(injection) : 200°C 春 實施例2 再度分離H(CF2CF2)nCH2〇H(n=2以上)之存留份，得到 H(CF2CF2)2CH2〇H之區分物，對該區分物與上述實施例1相同 加入曱醇鈉並加以蒸餾，藉此，得到蒸發殘份為25ppm以下 -之H(CF2CF2)2CH2OH。 實施例3 11
Claims (1)
1247734 Η： ： 50kPa 溫度：50°C(5分)〜220°C15分(以15°C/分昇溫) 庄入溫度(injection temperature) : 200〇C。 9·一種資訊記錄媒體之製造方法，包含步驟： 敗醇組成物 挺供一由申請專利範圍第1項至第8項之任一 所製成之基板；
在所述基板上形成可用雷射寫入及/或讀取資訊之記錄 10·—種資訊記錄媒體，包含： 由一氟醇組成物所製成的一基板，其中所述氟醇組成物 包含以下式表示之氟 HCCFR^Fo^^OH (1) 〔η二1時R〗表示F或CF3，n=2時Ri表示F〕；以及含量為〇·〇01 ppm至50ppm的蒸發殘份：以及 一位在所述基板上而可用雷射寫入及/或讀取資訊之記 錄層。 14
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1999
- 1999-02-25 JP JP11048446A patent/JP3029618B1/ja not_active Expired - Lifetime
- 1999-05-31 TW TW088109006A patent/TWI247733B/zh not_active IP Right Cessation
- 1999-05-31 TW TW093132813A patent/TWI247734B/zh not_active IP Right Cessation
- 1999-08-30 AU AU44844/99A patent/AU724446B2/en not_active Expired
- 1999-09-01 IL IL13168199A patent/IL131681A0/xx unknown
- 1999-09-01 US US09/388,384 patent/US6392105B1/en not_active Expired - Lifetime
- 1999-09-02 NZ NZ337609A patent/NZ337609A/xx not_active IP Right Cessation
- 1999-09-08 DE DE69904117T patent/DE69904117T2/de not_active Expired - Lifetime
- 1999-09-08 AT AT99117436T patent/ATE228494T1/de active
- 1999-09-08 CA CA002282063A patent/CA2282063C/en not_active Expired - Lifetime
- 1999-09-08 EP EP99117436A patent/EP0967193B1/en not_active Expired - Lifetime
- 1999-09-08 EP EP01124226A patent/EP1179521A1/en not_active Withdrawn
- 1999-09-08 ES ES99117436T patent/ES2186286T3/es not_active Expired - Lifetime
- 1999-09-14 CN CN031014704A patent/CN1600766B/zh not_active Expired - Lifetime
- 1999-09-14 CN CN99119085A patent/CN1117053C/zh not_active Expired - Lifetime
- 1999-09-20 BG BG103746A patent/BG103746A/xx unknown
- 1999-09-24 MX MXPA99008815A patent/MXPA99008815A/es not_active Application Discontinuation
- 1999-09-29 BR BR9904405-6A patent/BR9904405A/pt not_active IP Right Cessation
- 1999-10-29 KR KR1019990047371A patent/KR100330273B1/ko not_active IP Right Cessation
- 1999-12-27 RU RU99127444/04A patent/RU2198160C2/ru active
- 1999-12-28 SG SG1999006653A patent/SG76643A1/en unknown
-
2001
- 2001-12-06 KR KR10-2001-0077064A patent/KR100386834B1/ko not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CA2282063A1 (en) | 2000-06-28 |
| AU4484499A (en) | 2000-06-29 |
| KR100386834B1 (ko) | 2003-06-09 |
| CN1258669A (zh) | 2000-07-05 |
| US6392105B1 (en) | 2002-05-21 |
| NZ337609A (en) | 2000-09-29 |
| ES2186286T3 (es) | 2003-05-01 |
| CA2282063C (en) | 2003-11-18 |
| EP1179521A1 (en) | 2002-02-13 |
| KR20010112910A (ko) | 2001-12-22 |
| EP0967193B1 (en) | 2002-11-27 |
| RU2198160C2 (ru) | 2003-02-10 |
| KR20000047569A (ko) | 2000-07-25 |
| TW200510285A (en) | 2005-03-16 |
| JP3029618B1 (ja) | 2000-04-04 |
| CN1600766A (zh) | 2005-03-30 |
| IL131681A0 (en) | 2001-03-19 |
| KR100330273B1 (ko) | 2002-04-01 |
| SG76643A1 (en) | 2000-11-21 |
| TWI247733B (en) | 2006-01-21 |
| ATE228494T1 (de) | 2002-12-15 |
| BG103746A (en) | 2001-08-31 |
| BR9904405A (pt) | 2000-09-19 |
| DE69904117T2 (de) | 2003-07-24 |
| MXPA99008815A (es) | 2007-07-02 |
| EP0967193A2 (en) | 1999-12-29 |
| EP0967193A3 (en) | 2000-04-26 |
| CN1117053C (zh) | 2003-08-06 |
| DE69904117D1 (de) | 2003-01-09 |
| AU724446B2 (en) | 2000-09-21 |
| CN1600766B (zh) | 2010-05-26 |
| JP2000247916A (ja) | 2000-09-12 |
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| MK4A | Expiration of patent term of an invention patent |