CN1316983A - 1,1,1,3,3-五氟丁烷的纯化 - Google Patents
1,1,1,3,3-五氟丁烷的纯化 Download PDFInfo
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- WZLFPVPRZGTCKP-UHFFFAOYSA-N 1,1,1,3,3-pentafluorobutane Chemical compound CC(F)(F)CC(F)(F)F WZLFPVPRZGTCKP-UHFFFAOYSA-N 0.000 title abstract description 6
- 238000000746 purification Methods 0.000 title abstract description 6
- 238000000034 method Methods 0.000 claims abstract description 16
- 150000001875 compounds Chemical class 0.000 claims abstract description 15
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 15
- 239000012535 impurity Substances 0.000 claims abstract description 14
- LFMIQNJMJJKICW-UHFFFAOYSA-N 1,1,2-trichloro-2-fluoroethene Chemical group FC(Cl)=C(Cl)Cl LFMIQNJMJJKICW-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000011737 fluorine Substances 0.000 claims abstract description 13
- 239000007787 solid Substances 0.000 claims abstract description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000000460 chlorine Substances 0.000 claims abstract description 6
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 6
- 239000007791 liquid phase Substances 0.000 claims abstract description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 0.000 claims abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract 6
- 239000002594 sorbent Substances 0.000 claims description 15
- 238000012544 monitoring process Methods 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 8
- 238000012545 processing Methods 0.000 claims description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 6
- 239000007789 gas Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 4
- 239000000377 silicon dioxide Substances 0.000 claims description 3
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 2
- 229960001866 silicon dioxide Drugs 0.000 claims description 2
- 235000012239 silicon dioxide Nutrition 0.000 claims description 2
- HXELGNKCCDGMMN-UHFFFAOYSA-N [F].[Cl] Chemical class [F].[Cl] HXELGNKCCDGMMN-UHFFFAOYSA-N 0.000 claims 1
- 229910021417 amorphous silicon Inorganic materials 0.000 claims 1
- 229910052756 noble gas Inorganic materials 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract description 9
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 abstract description 9
- 229910000041 hydrogen chloride Inorganic materials 0.000 abstract description 9
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 abstract description 4
- 229910000040 hydrogen fluoride Inorganic materials 0.000 abstract description 4
- 239000003795 chemical substances by application Substances 0.000 abstract description 2
- 230000003247 decreasing effect Effects 0.000 abstract 4
- 238000001179 sorption measurement Methods 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 7
- 239000012043 crude product Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 238000004817 gas chromatography Methods 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 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
- 229910004298 SiO 2 Inorganic materials 0.000 description 2
- 238000011088 calibration curve Methods 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- BSRRYOGYBQJAFP-UHFFFAOYSA-N 1,1,1,2,2,3-hexafluorobutane Chemical compound CC(F)C(F)(F)C(F)(F)F BSRRYOGYBQJAFP-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- XRPKRSLLVXAECN-UHFFFAOYSA-N CCCC.[F] Chemical compound CCCC.[F] XRPKRSLLVXAECN-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 150000001722 carbon compounds Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000004334 fluoridation Methods 0.000 description 1
- 238000003682 fluorination reaction Methods 0.000 description 1
- 150000005826 halohydrocarbons Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical class CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- -1 pentachloro-butane compound Chemical class 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/38—Separation; Purification; Stabilisation; Use of additives
- C07C17/389—Separation; Purification; Stabilisation; Use of additives by adsorption on solids
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B7/00—Halogens; Halogen acids
- C01B7/01—Chlorine; Hydrogen chloride
- C01B7/07—Purification ; Separation
- C01B7/0706—Purification ; Separation of hydrogen chloride
- C01B7/0718—Purification ; Separation of hydrogen chloride by adsorption
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B7/00—Halogens; Halogen acids
- C01B7/19—Fluorine; Hydrogen fluoride
- C01B7/191—Hydrogen fluoride
- C01B7/195—Separation; Purification
- C01B7/197—Separation; Purification by adsorption
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/38—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/38—Separation; Purification; Stabilisation; Use of additives
- C07C17/395—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to a chemical modification of at least one compound
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Treatment Of Liquids With Adsorbents In General (AREA)
Abstract
本发明涉及制备具有降低含量的HCl、HF或不饱和杂质的纯化的1,1,1,3,3-五氟丁烷(HFC-365mfc)的方法。为此,将待纯化的原料于液相中用固体无机吸附剂或用双原子的、可加成至C-C多重键的分子处理。优选用元素氟处理待纯化的产物。氟化氢和氯化氢的含量可降至低于1ppm,不饱和(氯)-氟-化合物的含量可降至低于20ppm,不饱和C2-化合物的含量可降至低于10ppm。此外,还发现,在监控1,1,1,3,3-五氟丁烷的纯化时,可将氟三氯乙烯作为监控物质。
Description
本发明涉及纯化的1,1,1,3,3-五氟丁烷(HFC-365mfc)的制备方法。
1,1,1,3,3-五氟丁烷例如作为发泡剂用于制备发泡塑料。它可例如由相应的五氯丁烷化合物、氟化氢和氟化催化剂制备。以这种方式制备的1,1,1,3,3-五氟丁烷可含有氯化氢、氟化氢及不饱和碳化合物,其来自于氟化反应或使用的原料。由不纯的产物制得纯化的产物是所希望的。这一任务由本发明的方法得以实现。
在本发明方法中,由粗1,1,1,3,3-五氟丁烷制备具有减少含量的HCl、HF和/或不饱和杂质的纯化的1,1,1,3,3-五氟丁烷,其中将粗1,1,1,3,3-五氟丁烷于液相中用固体无机吸附剂或双原子的可加成至C-C多重键上的分子处理并分离出处理的1,1,1,3,3-五氟丁烷。
选择压力和温度,以使在液相中进行操作。优选的压力为1-5大气压(绝对的)。
使用固体无机吸附剂既可分离酸性组分,也可分离不饱和杂质。使用双原子分子成功地将不饱和化合物衍生化成非毒性和/或可蒸馏分离的化合物。
优选的固体无机吸附剂是活性炭和基于氧化铝或二氧化硅的吸附剂。它们特别适于分离氯化氢和/或氟化氢。
用吸附剂处理宜在-30℃至+100℃,优选15至25℃温度下进行。
为了减少不饱和化合物的含量,使用氯化氢或元素氟、氯或氢作为优选的双原子分子。
其中可设计成这样,即首先借助于所述的双原子分子降低不饱和化合物的含量并且接着借助于固体无机吸附剂降低其它杂质的含量。
特别优选的是,为了降低不饱和化合物的含量,使用元素氟、优选其与惰性气体如氮气或氩气的混合物。用元素氟(或其与惰性气体的混合物)进行的处理宜在-80至+20℃、优选-20至-10℃温度下进行。即使在低至10体积%的氟浓度下,就已观察到了良好的作用。
取决于处理时间或起纯化作用的试剂的用量,可以将杂质或多或少地完全分离。因此如果例如使用比加成至不饱和杂质所需量更少的氟,则在纯化产物中存留相应量的杂质。但这可以通过简单的试验和产物分析来计算。优选用元素氟或其与惰性气体的混合物处理这样长的时间,以使获得的1,1,1,3,3-五氟丁烷含有最高含量为20ppm的不饱和氯-氟-化合物和10ppm的不饱和C2-化合物。处理进行这样长的时间直至氯化氢和/或氟化氢的含量最高各为1ppm,为此尤其使用无定形二氧化硅或氧化铝处理。
如果已用双原子分子对粗产物进行过处理,可以通过分级冷凝或例如通过蒸馏来将所得的产物分离成纯的五氟丁烷和其它卤代烃。
借助于本发明方法使得可能制备最高含有1ppmHF、1ppmHCl。10ppm不饱和(氯)-氟-化合物和10ppm不饱和C2-化合物的1,1,1,3,3-五氟丁烷。这种高纯的五氟丁烷是新颖的并且同样是本发明的主题。
本发明方法特别适于纯化这样的1,1,1,3,3-五氟丁烷,它被氟三氯乙烯(作为唯一的杂质或是杂质的成分)污染。已证实氟三氯乙烯尤其难以被分离,因为它是很惰性的。使用本发明方法可以将这一杂质降低至最高为20ppm的含量,甚至低于0.1ppm的含量。
基于其反应惰性,在被氟三氯乙烯和其它不饱和化合物污染的1,1,1,3,3-五氟丁烷的纯化监测(监控)中,可将氟三氯乙烯作为监控物质(Kontrollsubstanz)。出乎预料地发现,只需监测氟三氯乙烯的贫化,而不需要同时监测其它不饱和化合物的贫化。当氟三氯乙烯降至所需含量时,其它不饱和化合物同样已被贫化。在监控包含氟三氯乙烯和其它不饱和化合物作为杂质的1,1,1,3,3-五氟丁烷的纯化时,应用氟三氯乙烯作为监控物质同样是本发明的主题。在此可借助于GC-MS(SIM-Lauf=选择性离子质量)进行监测。在使用气相色谱(GC)-热导性测定(t.c.d.,热传导性检测)进行测定时,CFC1111的检测极限为100ppm。使用SIM-Lauf-Modus(SIM操作状态)的GC-MS(g.c.-m.s.)时,CFC1111的检测极限为0.1ppm。
借助于本发明的纯化方法可以制得高纯的1,1,1,3,3-五氟丁烷。迄今这类纯化操作仅在较高稳定性的氟化或全卤化化合物的情况下进行。用元素氟处理尤其带来了令人惊异的结果,因为人们会担心不是加成至不饱和化合物上,而是在五氟丁烷上发生取代反应形成六氟丁烷、七氟丁烷或全氟丁烷。根据本发明在监控时使用氟三氯乙烯作为监控物质导致节省了时间,因为在记录和评价光谱时,可以集中在记录氟三氯乙烯的部分。在液相中操作节省了能源。
以下实施例进一步说明本发明,而并非要对其范围加以限制。所有的试验在液相中进行。
实施例1:分离不饱和组分
a)使用含有0.22%(气相色谱面积百分比)CFC-1111和99.4%HFC365mfc的HFC365mfc。
aⅠ)将84.8g粗产物与6.8g氯气在0.2g FeCl3存在下于40℃反应。蒸馏反应混合物。在馏份中还检测到0.11%CFC-1111。因此该杂质的含量已经减半。
aⅡ)于高压釜中,将115.3g粗产物在催化剂上(4.5重量%Pd;0.5重量%Rh,于活性炭上)用0.8g H2氢化。在反应混合物中仅含有0.03%CFC-1111。
b)使用含有0.16%(气相色谱面积百分比)CFC-1111和99.68%HFC 365mfc的HFC 365mfc作为粗产物
bⅠ)将93.6g粗产物与2.3g碘(KI/I2形式)反应。在反应混合物中还存在0.08%CFC-1111。
bⅡ)将195.6g粗产物与0.72升F2/N2混合物(10%F2)于-20℃反应。在反应混合物中检测不到CFC-1111。
实施例2:分离CFC-1111和酸性组分
使用CFC-1111含量为约0.2%(GB中的面积百分比)的272kgHFC365mfc。该含量相当于约2,000ppm。反应在具有循环路线的反应器中进行。在冷却至-12℃时,每小时通入150升F2/N2混合物(3体积%F2)。历时12小时,之后温热反应混合物并蒸馏出HFC 365mfc。将馏份与SiO2基的吸附剂接触,酸性组分(尤其HCl和HF)的含量。为此使用“AF400”作为吸附剂。这是一种无铝、基于SiO2的珠状吸附剂,其孔直径为400A(40nm),供应商为:Kali-Chemie/Engelhard,Nienburg。
将HFC 365mfc与吸附剂分离后,HCl的含量低于1ppm,HF的含量同样低于1ppm。
(注解:为了测定CFC-1111在产物中的含量,在GC-MS仪器的Sim-MS状态下操作。首先作出校正曲线,以便确定在0.1ppm CFC-1111和10ppm时的离子流(为此使用HFC 365mfc和相应浓度的CFC-1111的已制备好的混合物)。借助于校正曲线和观察到的离子流,确定相应的CFC-1111浓度。)
Claims (11)
1.由粗1,1,1,3,3-五氟丁烷制备具有降低含量的HCl、HF和/或不饱和杂质的纯化1,1,1,3,3-五氟丁烷的方法,其中将粗1,1,1,3,3-五氟丁烷于液相中用固体无机吸附剂或双原子的、可加成至C-C多重键上的分子处理和将处理的1,1,1,3,3-五氟丁烷分离。
2.根据权利要求1的方法,其特征在于,使用活性炭或基于氧化铝或二氧化硅的吸附剂作为固体无机吸附剂。
3.根据权利要求2的方法,其特征在于,所述吸附剂用于分离HCl和/或HF。
4.根据权利要求1的方法,其特征在于,用吸附剂的处理在-30至+100,优选15至25℃温度下进行。
5.根据权利要求1的方法,其特征在于,为降低不饱和化合物含量,使用HCl或元素氟、氯或氢作为双原子分子。
6.根据权利要求5的方法,其特征在于,使用与惰性气体混合的元素氟。
7.根据权利要求6的方法,其特征在于,在-80至+20℃的温度下进行用元素氟的处理。
8.根据权利要求6或7的方法,其特征在于,用元素氟或氟与惰性气体混合物处理这样长的时间,直至获得的1,1,1,3,3-五氟丁烷中最高含有20ppm的不饱和(氯)一氟一化合物和10ppm的不饱和C2-化合物。
9.根据权利要求1的方法,其特征在于,用无定形SiO2或Al2O3处理这样长的时间,直至HCl和/或HF的最高含量各为1ppm。
10.1,1,1,3,3-五氟丁烷,其特征在于,它最高含有1ppm HF,1ppm HCl,20ppm不饱和(氯)-氟-化合物和10ppm不饱和C2-化合物。
11.在监控含有氟三氯乙烯和其它不饱和化合物作为杂质的1,1,1,3,3-五氟丁烷的纯化时,氟三氯乙烯作为监控物质的应用。
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Application Number | Priority Date | Filing Date | Title |
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DE19840099 | 1998-09-03 | ||
DE19840099.3 | 1998-09-03 |
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US (1) | US6500994B1 (zh) |
EP (2) | EP1109766B1 (zh) |
JP (1) | JP4520638B2 (zh) |
KR (1) | KR100633784B1 (zh) |
CN (1) | CN1166601C (zh) |
AT (1) | ATE281422T1 (zh) |
AU (1) | AU755192B2 (zh) |
BR (1) | BR9913453A (zh) |
CA (1) | CA2342925C (zh) |
DE (2) | DE19940104A1 (zh) |
DK (1) | DK1109766T3 (zh) |
ES (1) | ES2229816T3 (zh) |
HK (1) | HK1039777B (zh) |
PT (1) | PT1109766E (zh) |
WO (1) | WO2000014040A1 (zh) |
ZA (1) | ZA200101801B (zh) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101913982A (zh) * | 2010-09-07 | 2010-12-15 | 西安近代化学研究所 | 1,1,1,3,3-五氟丁烷的制备方法 |
Families Citing this family (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ATE281422T1 (de) | 1998-09-03 | 2004-11-15 | Solvay Fluor & Derivate | Reinigung von 1,1,1,3,3-pentafluorbutan |
JP4552246B2 (ja) * | 1999-12-28 | 2010-09-29 | 株式会社クレハ | 精製フルオロカーボン又はクロロフルオロカーボンの製造方法 |
FR2806077B1 (fr) * | 2000-03-07 | 2004-01-30 | Solvay | Procede pour l'obtention d'un hydrofluoroalcane epure, hydrofluoroalcane epure, utilisation de l'hydrofluoroalcane et methode d'analyse d'un hydrofluoroalcane |
FR2812872A1 (fr) * | 2000-08-10 | 2002-02-15 | Solvay | Procede d'obtention d'un hydrofluoalcane epure |
EP1985601A3 (en) | 2000-08-10 | 2008-12-17 | SOLVAY (Société Anonyme) | Process for obtaining a purified hydrofluoroalkane |
FR2812869A1 (fr) * | 2000-08-10 | 2002-02-15 | Solvay | Procede d'obtention d'un hydrofluoroalcane epure |
FR2812871A1 (fr) * | 2000-08-10 | 2002-02-15 | Solvay | Procede d'obtention d'un hydrofluoroalcane epure |
US8158139B2 (en) * | 2004-07-12 | 2012-04-17 | Taro Pharmaceuticals North America, Inc. | Topical gel formulation comprising organophosphate insecticide and preparation thereof |
WO2006017263A1 (en) | 2004-07-12 | 2006-02-16 | Taro Pharmaceutical Industries Ltd. | Topical gel formulation comprising organophosphate insecticide and its preparation thereof |
US7560445B2 (en) * | 2005-07-06 | 2009-07-14 | Taro Pharmaceuticals North America, Inc. | Process for preparing malathion for pharmaceutical use |
JP2008237989A (ja) * | 2007-03-26 | 2008-10-09 | Toyobo Co Ltd | 有機溶剤処理装置 |
EP2170789A1 (en) * | 2007-07-20 | 2010-04-07 | Solvay Fluor GmbH | Process for obtaining a purified hydrofluoroalkane |
JP6206198B2 (ja) | 2013-07-19 | 2017-10-04 | 日本ゼオン株式会社 | 2−フルオロブタンの精製方法 |
US10472308B2 (en) | 2016-08-25 | 2019-11-12 | Zeon Corporation | Butene conversion method and monofluorobutane purification method |
CN110092707B (zh) * | 2018-01-30 | 2020-08-11 | 中昊晨光化工研究院有限公司 | 一种四氟乙烯生产过程中去除氟化氢的方法 |
Family Cites Families (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3696156A (en) * | 1970-04-03 | 1972-10-03 | Du Pont | Process for purification of fluoroperhalocarbons |
DE2310749A1 (de) * | 1973-03-03 | 1974-09-12 | Bayer Ag | Verfahren zur entfernung von fluorwasserstoff aus organischen fluorverbindungen |
DE3311751A1 (de) | 1983-03-31 | 1984-10-04 | Hoechst Ag, 6230 Frankfurt | Verfahren zur reinigung von fluorkohlenwasserstoffen |
ATE108429T1 (de) * | 1988-11-22 | 1994-07-15 | Du Pont | Verfahren zur reinigung von gesättigten halokohlenwasserstoffen. |
US5001287A (en) * | 1989-02-02 | 1991-03-19 | E. I. Du Pont De Nemours And Company | Purification of saturated halocarbons |
US5300714A (en) * | 1990-05-18 | 1994-04-05 | Minnesota Mining And Manufacturing Company | Method of purifying saturated fluoroperhalocarbon liquids |
JPH0656713A (ja) * | 1991-04-27 | 1994-03-01 | Hoechst Ag | クロロフルオロ炭化水素の精製方法 |
JPH0570381A (ja) * | 1991-09-11 | 1993-03-23 | Central Glass Co Ltd | 1,1−ジクロロ−1−フルオロエタンの精製方法 |
US5569797A (en) | 1992-01-07 | 1996-10-29 | E. I. Du Pont De Nemours And Company | Method of removing olefinic impurities from hydrochlorofluorocarbons |
RU2058283C1 (ru) * | 1993-06-24 | 1996-04-20 | Акционерное общество открытого типа "Кирово-Чепецкий химический комбинат им.Б.П.Константинова" | Способ очистки низших флорхлоралканов |
FR2724167B1 (fr) * | 1994-09-05 | 1996-11-29 | Solvay | Procede pour l'hydrofluoration de chloro (fluoro) butane |
DE19510159A1 (de) | 1995-03-21 | 1996-09-26 | Hoechst Ag | Verfahren zur Entfernung von olefinischen Verunreinigungen aus 2H-Heptafluorpropan (R 227) |
EP0902776B1 (en) | 1996-04-04 | 2002-06-19 | Honeywell International Inc. | PURIFICATION OF 1,1,1,3,3-PENTAFLUOROPROPANE (R-245fa) |
FR2754815B1 (fr) | 1996-10-18 | 1998-12-04 | Atochem Elf Sa | Purification du pentafluoroethane |
FR2768717B1 (fr) | 1997-09-24 | 1999-11-12 | Solvay | Procede de separation de fluorure d'hydrogene de ses melanges avec un hydrofluoroalcane contenant de 3 a 6 atomes de carbone |
ATE281422T1 (de) | 1998-09-03 | 2004-11-15 | Solvay Fluor & Derivate | Reinigung von 1,1,1,3,3-pentafluorbutan |
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1999
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- 1999-08-24 DK DK99968662T patent/DK1109766T3/da active
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- 1999-08-24 ES ES99968662T patent/ES2229816T3/es not_active Expired - Lifetime
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- 1999-08-24 KR KR1020017002269A patent/KR100633784B1/ko not_active IP Right Cessation
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101913982A (zh) * | 2010-09-07 | 2010-12-15 | 西安近代化学研究所 | 1,1,1,3,3-五氟丁烷的制备方法 |
Also Published As
Publication number | Publication date |
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DE19940104A1 (de) | 2000-03-09 |
KR100633784B1 (ko) | 2006-10-16 |
DE59911007D1 (de) | 2004-12-09 |
EP1109766B1 (de) | 2004-11-03 |
EP1500640A1 (de) | 2005-01-26 |
HK1039777A1 (en) | 2002-05-10 |
DK1109766T3 (da) | 2005-02-21 |
HK1039777B (zh) | 2005-03-11 |
AU1147700A (en) | 2000-03-27 |
CA2342925A1 (en) | 2000-03-16 |
US6500994B1 (en) | 2002-12-31 |
EP1109766A1 (de) | 2001-06-27 |
JP2002524431A (ja) | 2002-08-06 |
ATE281422T1 (de) | 2004-11-15 |
WO2000014040A1 (de) | 2000-03-16 |
CA2342925C (en) | 2009-01-20 |
KR20010072868A (ko) | 2001-07-31 |
AU755192B2 (en) | 2002-12-05 |
ES2229816T3 (es) | 2005-04-16 |
JP4520638B2 (ja) | 2010-08-11 |
BR9913453A (pt) | 2001-07-24 |
CN1166601C (zh) | 2004-09-15 |
ZA200101801B (en) | 2001-07-16 |
PT1109766E (pt) | 2005-02-28 |
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