JPH04173750A - Method for stabilizing 1,1-dichloro-2,2,2-trifluoroethane - Google Patents
Method for stabilizing 1,1-dichloro-2,2,2-trifluoroethaneInfo
- Publication number
- JPH04173750A JPH04173750A JP29972190A JP29972190A JPH04173750A JP H04173750 A JPH04173750 A JP H04173750A JP 29972190 A JP29972190 A JP 29972190A JP 29972190 A JP29972190 A JP 29972190A JP H04173750 A JPH04173750 A JP H04173750A
- Authority
- JP
- Japan
- Prior art keywords
- trifluoroethane
- dichloro
- generation
- phenols
- title compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- OHMHBGPWCHTMQE-UHFFFAOYSA-N 2,2-dichloro-1,1,1-trifluoroethane Chemical compound FC(F)(F)C(Cl)Cl OHMHBGPWCHTMQE-UHFFFAOYSA-N 0.000 title abstract 2
- 238000000034 method Methods 0.000 title description 4
- 230000000087 stabilizing effect Effects 0.000 title 1
- 238000000354 decomposition reaction Methods 0.000 claims abstract description 13
- 150000002989 phenols Chemical class 0.000 claims abstract description 9
- UJPMYEOUBPIPHQ-UHFFFAOYSA-N 1,1,1-trifluoroethane Chemical compound CC(F)(F)F UJPMYEOUBPIPHQ-UHFFFAOYSA-N 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 abstract description 5
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 abstract description 4
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 abstract description 4
- MGSRCZKZVOBKFT-UHFFFAOYSA-N thymol Chemical compound CC(C)C1=CC=C(C)C=C1O MGSRCZKZVOBKFT-UHFFFAOYSA-N 0.000 abstract description 4
- 239000000443 aerosol Substances 0.000 abstract description 3
- 239000002904 solvent Substances 0.000 abstract description 3
- JIGUICYYOYEXFS-UHFFFAOYSA-N 3-tert-butylbenzene-1,2-diol Chemical compound CC(C)(C)C1=CC=CC(O)=C1O JIGUICYYOYEXFS-UHFFFAOYSA-N 0.000 abstract description 2
- NPBVQXIMTZKSBA-UHFFFAOYSA-N Chavibetol Natural products COC1=CC=C(CC=C)C=C1O NPBVQXIMTZKSBA-UHFFFAOYSA-N 0.000 abstract description 2
- 239000005770 Eugenol Substances 0.000 abstract description 2
- BJIOGJUNALELMI-ONEGZZNKSA-N Isoeugenol Natural products COC1=CC(\C=C\C)=CC=C1O BJIOGJUNALELMI-ONEGZZNKSA-N 0.000 abstract description 2
- UVMRYBDEERADNV-UHFFFAOYSA-N Pseudoeugenol Natural products COC1=CC(C(C)=C)=CC=C1O UVMRYBDEERADNV-UHFFFAOYSA-N 0.000 abstract description 2
- 239000005844 Thymol Substances 0.000 abstract description 2
- BJIOGJUNALELMI-ARJAWSKDSA-N cis-isoeugenol Chemical compound COC1=CC(\C=C/C)=CC=C1O BJIOGJUNALELMI-ARJAWSKDSA-N 0.000 abstract description 2
- 229960002217 eugenol Drugs 0.000 abstract description 2
- 239000004088 foaming agent Substances 0.000 abstract description 2
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 abstract description 2
- 229960000790 thymol Drugs 0.000 abstract description 2
- BJIOGJUNALELMI-UHFFFAOYSA-N trans-isoeugenol Natural products COC1=CC(C=CC)=CC=C1O BJIOGJUNALELMI-UHFFFAOYSA-N 0.000 abstract description 2
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 abstract description 2
- 229940029284 trichlorofluoromethane Drugs 0.000 abstract description 2
- CYXIKYKBLDZZNW-UHFFFAOYSA-N 2-Chloro-1,1,1-trifluoroethane Chemical compound FC(F)(F)CCl CYXIKYKBLDZZNW-UHFFFAOYSA-N 0.000 abstract 2
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 abstract 1
- 239000003183 carcinogenic agent Substances 0.000 abstract 1
- 239000002609 medium Substances 0.000 abstract 1
- 238000005057 refrigeration Methods 0.000 abstract 1
- 239000003381 stabilizer Substances 0.000 description 8
- 230000000694 effects Effects 0.000 description 5
- 229920002635 polyurethane Polymers 0.000 description 5
- 239000004814 polyurethane Substances 0.000 description 5
- 238000005187 foaming Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- -1 0-methoxyphenol Chemical compound 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000010687 lubricating oil Substances 0.000 description 3
- 229920005862 polyol Polymers 0.000 description 3
- 150000003077 polyols Chemical class 0.000 description 3
- 239000003507 refrigerant Substances 0.000 description 3
- ASHGTJPOSUFTGB-UHFFFAOYSA-N 3-methoxyphenol Chemical compound COC1=CC=CC(O)=C1 ASHGTJPOSUFTGB-UHFFFAOYSA-N 0.000 description 2
- 239000004604 Blowing Agent Substances 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 229910000039 hydrogen halide Inorganic materials 0.000 description 2
- 239000012433 hydrogen halide Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- MMSLOZQEMPDGPI-UHFFFAOYSA-N p-Mentha-1,3,5,8-tetraene Chemical compound CC(=C)C1=CC=C(C)C=C1 MMSLOZQEMPDGPI-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- CZBZUDVBLSSABA-UHFFFAOYSA-N butylated hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1.COC1=CC=C(O)C=C1C(C)(C)C CZBZUDVBLSSABA-UHFFFAOYSA-N 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 231100000315 carcinogenic Toxicity 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000012611 container material Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 150000003739 xylenols Chemical class 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
[産業上の利用分野]
本発明は、t、i−ジクロロ−2,2,2−1−リフル
オロエタンC以下、R123という)の安定化を行い、
分解生成物であるl−クロロ−2,2,2−トリフルオ
ロエタン(以下、R133aという)の発生を抑制する
方法に関するものである。Detailed Description of the Invention [Industrial Application Field] The present invention stabilizes t,i-dichloro-2,2,2-1-lifluoroethane C (hereinafter referred to as R123),
The present invention relates to a method for suppressing the generation of l-chloro-2,2,2-trifluoroethane (hereinafter referred to as R133a), which is a decomposition product.
[従来の技術]
従来、ポリウレタン発泡、ターボ冷凍機、洗浄等におい
て、トリクロロフルオロメタン(以下、R11という)
が使用されてきた。しかし、完全ハロゲン化炭化水素類
は、オゾン層に対する環境問題が指摘されており、代替
物質の開発が急務となっている。[Prior Art] Conventionally, trichlorofluoromethane (hereinafter referred to as R11) has been used in polyurethane foaming, turbo chillers, cleaning, etc.
has been used. However, fully halogenated hydrocarbons have been pointed out to pose environmental problems to the ozone layer, and there is an urgent need to develop alternative substances.
R11代替物質としてR123が有力視されている。R123 is considered to be a promising substitute for R11.
R123は安定性が優れているが、各種化合物が共存す
る場合には、安定性が低下し、各種分解生成物を生じる
といわれている。分解を促進する共存物質としては、例
えば、溶剤においては溶解性を高める目的より、アルコ
ールが添加されていると共に、洗浄機や被洗物材料との
接触、油等の汚れ成分や水分の混入等があげられる。一
方、プロペラントにおいては水溶性有効成分を溶解させ
る目的よりアルコールが添加されていると共に、容器材
料があげられる。Although R123 has excellent stability, it is said that when various compounds coexist, the stability decreases and various decomposition products are produced. Coexisting substances that promote decomposition include, for example, alcohol is added to solvents to increase solubility, contact with washing machines and materials to be washed, contamination components such as oil, and moisture contamination. can be given. On the other hand, in propellants, alcohol is added for the purpose of dissolving water-soluble active ingredients, and container materials are also included.
又、発泡剤として使用するポリウレタン発泡に纏いては
、ポリウレタン原料であるポリオールや触媒、整泡剤や
発泡機とR123が接触する。ターボ冷凍機等の冷媒と
して使用する場合には、冷凍機を構成する材料や潤滑油
があげられる。In addition, when foaming polyurethane used as a foaming agent, R123 comes into contact with polyol, which is a polyurethane raw material, a catalyst, a foam stabilizer, and a foaming machine. When used as a refrigerant for a centrifugal refrigerator or the like, examples include materials constituting the refrigerator and lubricating oil.
R123の分解が起こると、例えば、エアゾール製品に
おいては、アルコールの酸化されたものによる臭気や液
の着色、あるいは分解生成物であるハロゲン化水素によ
る容器の腐食、又、ポリウレタン発泡においては、触媒
の不活性化による発泡倍率の低下、原料ポリオールの粘
度の上昇、製品の黄褐色化、冷凍機においては、分解生
成物であるハロゲン化水素により機械の腐食や潤滑油の
劣化に基づく機械の故障等好ましからざる問題を発生さ
せる。更に、大きな問題としては、R123の分解の結
果、R133aが発生する。When decomposition of R123 occurs, for example, in aerosol products, it causes odor and coloring of the liquid due to oxidized alcohol, or corrosion of the container due to hydrogen halide, which is a decomposition product, and in polyurethane foaming, it causes damage to the catalyst. Decrease in expansion ratio due to inactivation, increase in the viscosity of the raw material polyol, yellowing of the product, corrosion of the machine due to hydrogen halide which is a decomposition product in refrigerators, machine failure due to deterioration of lubricating oil, etc. cause undesirable problems. Furthermore, a major problem is that R133a is generated as a result of the decomposition of R123.
[発明が解決しようとする課題]
R123の分解の結果生成するR133aは発癌性の疑
いが持たれており、安全性の点より、発生を抑制するの
が極めて重要である。[Problems to be Solved by the Invention] R133a produced as a result of the decomposition of R123 is suspected of being carcinogenic, and from the standpoint of safety, it is extremely important to suppress its occurrence.
[課題を解決するための手段]
本発明は前述の問題点を解決すべく、R123の安定剤
検討を重ねた結果、本発明者らは、フェノール類が著し
いR133a生成抑制効果を発揮できることを見いだし
本発明を完成するに至った。[Means for Solving the Problems] In order to solve the above-mentioned problems, the present inventors have repeatedly investigated stabilizers for R123, and as a result, the present inventors have discovered that phenols can exhibit a remarkable effect of suppressing the production of R133a. The present invention has now been completed.
すなわち、本発明は、フェノール類を含有せしめること
を特徴とするR123からのR133a発生を抑制する
方法に関するものである。That is, the present invention relates to a method for suppressing the generation of R133a from R123, which is characterized by containing a phenol.
本発明におけるフェノール類としては、水酸基以外にア
ルキル基、アルケニル基、アルコキシ基、カルボキシル
基、カルボニル基、ハロゲン等各種の置換基を含むフェ
ノール類も含むものである。例えば、2,6−ジーt−
ブチル−p−クレゾール、0−クレゾール、■−クレゾ
ール、p−クレゾール、チモール、p−t−ブチルフェ
ノール、0−メトキシフェノール、m−メトキシフェノ
ール、p−メトキシフェノール、オイゲノール、イソオ
イゲノール、ブチルヒドロキシアニソール、フェノール
、キシレノール等の1価のフェノールあるいはt−ブチ
ルカテコール、2.5−ジ−t−アミルハイドロキノン
、2.5−ジ−t−ブチルハイドロキノン等の2価のフ
ェノール等である。Phenols in the present invention include phenols containing various substituents other than hydroxyl groups, such as alkyl groups, alkenyl groups, alkoxy groups, carboxyl groups, carbonyl groups, and halogens. For example, 2,6-G-t-
Butyl-p-cresol, 0-cresol, ■-cresol, p-cresol, thymol, p-t-butylphenol, 0-methoxyphenol, m-methoxyphenol, p-methoxyphenol, eugenol, isoeugenol, butylhydroxyanisole, These include monovalent phenols such as phenol and xylenol, and divalent phenols such as t-butylcatechol, 2.5-di-t-amylhydroquinone, and 2.5-di-t-butylhydroquinone.
本発明における安定剤の含有割合は特に限定されないが
、R123に対して0.0005〜10wt%、好まし
くは、0.001〜5wt%が適当である。The content of the stabilizer in the present invention is not particularly limited, but is suitably 0.0005 to 10 wt%, preferably 0.001 to 5 wt%, based on R123.
又、本発明の安定剤にさらに他の安定剤、例えば、エポ
キシ化合物、ニトロ基を含有する炭化水素類、α−メチ
ルスチレンやp−イソプロペニルトルエン等の炭化水素
類等を0.001〜5wt%〜添加することも可能であ
る。In addition, 0.001 to 5 wt of other stabilizers such as epoxy compounds, hydrocarbons containing a nitro group, hydrocarbons such as α-methylstyrene and p-isopropenyltoluene may be added to the stabilizer of the present invention. It is also possible to add up to %.
【実施例]
以下、本発明を実施例により具体的に説明するが、本発
明はこれらの実施例のみに限定されるものではない。[Examples] Hereinafter, the present invention will be specifically explained using Examples, but the present invention is not limited to these Examples.
ポリウレタン発泡剤としての結果を表1に示す。試料と
して次に示す混合液を調製し、ポリオール EL−7
50ED 100重量部(旭オーリン社製)
触 媒 Dabco 33LV 2重量部
(三共エアープロダクト社製)
整 泡 剤 5H−1932重量部
(東しシリコーン社製)
純水 4重量部R123(C
HC12CF3) 40重量部これに安定剤
の所定量を混合し、これを耐圧ガラス容器に封入し、熱
風循環型恒温槽中で温度90℃に保持し、3日間加熱試
験を行う。加熱試験後に、分解生成物であるR133a
の発生量をガスクロマトグラフィーを用い分析すること
により、R133a発生抑制効果を測定できる。Table 1 shows the results as a polyurethane blowing agent. The following mixed solution was prepared as a sample, and polyol EL-7
50ED 100 parts by weight (manufactured by Asahi Olin Co., Ltd.) Catalyst Dabco 33LV 2 parts by weight (manufactured by Sankyo Air Products Co., Ltd.) Foam stabilizer 5H-1932 parts by weight (manufactured by Toshi Silicone Co., Ltd.) Pure water 4 parts by weight R123 (C
40 parts by weight of HC12CF3) A predetermined amount of a stabilizer is mixed with this, sealed in a pressure-resistant glass container, maintained at a temperature of 90° C. in a hot air circulation thermostat, and subjected to a heating test for 3 days. After the heating test, the decomposition product R133a
The effect of suppressing R133a generation can be measured by analyzing the amount of R133a generated using gas chromatography.
表1
一方、冷媒としての結果を表2に示す。試料として次に
示す混合液を調製し、
潤滑油 肛ソ4GS 50重量部(日本
サン石油社製)
R123(CHCl、CF、) 100重量部
金属(SS41. Cu、 Al)
これに安定剤の所定量を混合し、これを耐圧金属容器に
封入し、熱風循環型恒温槽中で温度130℃に保持し、
14日間加熱試験を行う。加熱試験後に、分解生成物で
あるR133aの発生量をガスクロマトグラフィーを用
い分析することにより、R133a発生抑制効果を測定
できる。Table 1 On the other hand, Table 2 shows the results as a refrigerant. Prepare the following mixed solution as a sample, and add a stabilizer to this: 50 parts by weight of lubricating oil 4GS (manufactured by Nippon Sun Oil Co., Ltd.), 100 parts by weight of R123 (CHCl, CF,) metals (SS41. Cu, Al). Mix a fixed amount, seal it in a pressure-resistant metal container, and maintain it at a temperature of 130°C in a hot air circulation type constant temperature bath.
A heating test is conducted for 14 days. After the heating test, the R133a generation suppressing effect can be measured by analyzing the amount of R133a, which is a decomposition product, generated using gas chromatography.
表2
[発明の効果]
本発明の方法に従って安定化されたR123は、発泡剤
、冷媒、エアゾール用あるいは溶剤用等に使用でき、優
れたR133aの発生抑制効果がある。Table 2 [Effects of the Invention] R123 stabilized according to the method of the present invention can be used as a blowing agent, refrigerant, aerosol, or solvent, and has an excellent effect of suppressing the generation of R133a.
Claims (2)
,1,−ジクロロ−2,2,2−トリフルオロエタンを
安定化する方法。(1) 1 characterized by containing phenols
, 1,-dichloro-2,2,2-trifluoroethane.
2,2,2−トリフルオロエタンの分解生成物である1
−クロロ−2,2,2−トリフルオロエタンの発生を抑
制することにより、1,1,−ジクロロ−2,2,2−
トリフルオロエタンを安定化する方法。(2) Contains phenols, 1,1-dichloro-
1, which is a decomposition product of 2,2,2-trifluoroethane
By suppressing the generation of -chloro-2,2,2-trifluoroethane, 1,1,-dichloro-2,2,2-
How to stabilize trifluoroethane.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP29972190A JPH04173750A (en) | 1990-11-07 | 1990-11-07 | Method for stabilizing 1,1-dichloro-2,2,2-trifluoroethane |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP29972190A JPH04173750A (en) | 1990-11-07 | 1990-11-07 | Method for stabilizing 1,1-dichloro-2,2,2-trifluoroethane |
Publications (1)
Publication Number | Publication Date |
---|---|
JPH04173750A true JPH04173750A (en) | 1992-06-22 |
Family
ID=17876165
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP29972190A Pending JPH04173750A (en) | 1990-11-07 | 1990-11-07 | Method for stabilizing 1,1-dichloro-2,2,2-trifluoroethane |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH04173750A (en) |
-
1990
- 1990-11-07 JP JP29972190A patent/JPH04173750A/en active Pending
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