JPH0138776B2 - - Google Patents
Info
- Publication number
- JPH0138776B2 JPH0138776B2 JP58014816A JP1481683A JPH0138776B2 JP H0138776 B2 JPH0138776 B2 JP H0138776B2 JP 58014816 A JP58014816 A JP 58014816A JP 1481683 A JP1481683 A JP 1481683A JP H0138776 B2 JPH0138776 B2 JP H0138776B2
- Authority
- JP
- Japan
- Prior art keywords
- phosphoric acid
- formula
- halogenated
- reaction
- mol
- 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.)
- Expired
Links
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 24
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 12
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 12
- 150000001298 alcohols Chemical class 0.000 description 10
- 239000010779 crude oil Substances 0.000 description 8
- -1 propionate ester Chemical class 0.000 description 8
- 238000009835 boiling Methods 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- ACIAHEMYLLBZOI-ZZXKWVIFSA-N Unsaturated alcohol Chemical compound CC\C(CO)=C/C ACIAHEMYLLBZOI-ZZXKWVIFSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 150000003151 propanoic acid esters Chemical class 0.000 description 2
- WSPZFVOCHITLIY-UHFFFAOYSA-N 2,2,3,3-tetrachlorobutane Chemical compound CC(Cl)(Cl)C(C)(Cl)Cl WSPZFVOCHITLIY-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-N Metaphosphoric acid Chemical compound OP(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 150000002168 ethanoic acid esters Chemical class 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000005338 heat storage Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000002418 insect attractant Substances 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- XONPDZSGENTBNJ-UHFFFAOYSA-N molecular hydrogen;sodium Chemical compound [Na].[H][H] XONPDZSGENTBNJ-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
本発明は一般式 The present invention is based on the general formula
【式】
（式中のR1、R2は水素原子またはアルキル基、
X1、X2、X3およびX4はハロゲン原子である）の
ハロゲン化アルコールのプロピオン酸エステルの
製法の改良方法で、さらに詳しく言えば、ハロゲ
ン化アルコールよりプロピオン酸エステルを製造
する際に不飽和アルコールおよび不飽和アルコー
ルのプロピオン酸エステルの生成を極力おさえ
て、目的のハロゲン化プロピオン酸エステルの収
率を向上させる方法に関するものである。
本発明者は先に、ハロゲン化アルコールの酢酸
エステルを、塩素含有不飽和アルコールと無水酢
酸の混合液中にリン酸を滴下することによつて、
塩素含有アルコールの酢酸エステルの製造方法を
提案した。（日本特許第783105号）しかし、この
方法をプロピオン酸エステルの製造に適要した場
合に、前記のようにハロゲン化不飽和アルコール
およびハロゲン化不飽和エステルを副生する欠点
がある。このため、本発明者は、副生するハロゲ
ン化不飽和アルコールおよびそのエステルの生成
を極力おさえて、目的のプロピオン酸エステルの
収率を向上させる努力を行なつた結果、本発明を
なすに至つた。
本発明に従うと、一般式[Formula] (In the formula, R 1 and R 2 are hydrogen atoms or alkyl groups,
X 1 , X 2 , X 3 and The present invention relates to a method of suppressing the production of propionate esters of saturated alcohols and unsaturated alcohols as much as possible to improve the yield of the target halogenated propionate esters. The present inventor first prepared an acetic acid ester of a halogenated alcohol by dropping phosphoric acid into a mixture of a chlorine-containing unsaturated alcohol and acetic anhydride.
A method for producing acetate esters of chlorine-containing alcohols was proposed. (Japanese Patent No. 783105) However, when this method is applied to the production of propionic acid esters, it has the drawback of producing halogenated unsaturated alcohols and halogenated unsaturated esters as by-products as described above. Therefore, the present inventor made efforts to improve the yield of the target propionate ester by suppressing the production of by-product halogenated unsaturated alcohol and its ester as much as possible, and as a result, the present invention was achieved. Ivy. According to the invention, the general formula
【式】
（式中のR1、R2、X1、X2、X3およびX4は前記
と同じ意味を持つ）で表わされるハロゲン化アル
コールを無水プロピオン酸とリン酸の混合液中に
滴下後加熱反応せしめることを特徴とする。
一般式
（式中のR1、R2、X1、X2、X3およびX4は前記
と同じ意味を持つ）で示されるハロゲン化プロピ
オン酸エステルの製法である。
本発明方法において原料として用いられるハロ
ゲン化アルコールは直鎖状または枝分かれ状のい
ずれでもよいが、ハロゲン化アルコールの炭素数
は３〜10までが適当である。
ハロゲンとしてはフツ素原子、塩素原子、臭素
原子などが用いられる。無水プロピオン酸と混合
するリン酸は60゜Beを用い、場合によつてはメタ
リン酸、ポリリン酸を併用して用いることができ
る。
しかし、リン酸の濃度が高い場合などは次式で
示す反応により不飽和結合を有する化合物（）、
（）が生成する。
このため、無水プロピオン酸とリン酸を混合し
たのち、ハロゲン化アルコールと滴下反応させる
ことによつて（）、（）への反応が極力おさえ
られることがわかつた。
無水プロピオン酸はハロゲン化アルコール１に
対して１〜10が適当で、５〜６が最も好ましい。
この割合が少ないと副生物の生成が増加する。リ
ン酸は60℃Beのものであれば充分で、原料ハロ
ゲン化アルコールに対して30〜40モル％程度が適
当である。反応時間は１〜３時間で温度は90〜
100℃で充分である。
本発明のハロゲン化プロピオン酸エステルは、
昆虫の誘引物質としてまた臭素化して難燃処理剤
製造などが用いられる。また脱ハロゲン化を行な
つてアセチレン化合物となし、光エネルギーを蓄
えることのできる有機蓄熱剤の合成原料として有
用なものである。
次に本発明を実施例によつて、さらに詳細に説
明する。
実施例 １
２，２，３，３−テトラクロロプロパン−１−
オール12.69ｇ（0.05モル）を無水プロピオン酸
39.05ｇ（0.30モル）と60゜Beリン酸2.26ｇ（0.02
モル）の混合液中に０〜−５℃で30分かかつて滴
下する。滴下後反応液を90〜95℃の温度に徐々に
上昇させたのち、その温度で３時間加熱反応させ
た。反応後氷水中に投入分解し、四塩化炭素で抽
出する。抽出液は酸性水素ナトリウム水溶液およ
び塩化ナトリウムの飽和水溶液で洗つたのち亡硝
で乾燥した。抽出液より四塩化炭素および未反応
プロピオン酸を留去し、粗油19.80ｇを得た。粗
油を蒸留して沸点46.0〜108.0℃／10mmHgの留分
17.63ｇを得た。これを分留して沸点95.0℃／７
mmHg（d20 41.4213、n20 D1.4824）の留分12.10ｇ（収
率95.3％）を得た。この留分の元素分析値は、
Ｈ：3.09；Ｃ：28.58；Cl：55.73で分子式
C6H8O2Cl4の元素分析値Ｈ：3.17；Ｃ：28.37；
Cl：55.84の値とよく一致する。また赤外線吸収
スペクトルは、波数1753cm-1に強いエステルのカ
ルボニルのＣ＝Ｏの伸縮振動を示し、目的の１−
プロピオニルオキシ−２，２，３，３−テトラク
ロロプロパンである。
実施例 ２
３，３，４，４−テトラクロロベタン−２−オ
ール13.39ｇ（0.05モル）を無水プロピオン酸
39.05ｇ（0.30モル）と60゜Beリン酸2.26ｇ（0.02
モル）の混合液中に０〜−５℃で30分かかつて滴
下する。滴下後反応液を90〜95℃の温度に徐々に
上昇させたのち、その温度で３時間反応させた。
反応後、実施例１と同様に処理して粗油24.16ｇ
を得た。粗油を蒸留して沸点45.0〜112.0℃／10
mmHgの留分17.06ｇを得た。これをさらに分留し
て沸点101.0℃／７mmHg（d20 41.3849、n20 D1.4828、
Cl52.93％）の２−プロピオニルオキシ−３，３，
４，４−テトラクロロブタン11.77ｇ（収率87.8
％）を得た。
実施例 ３
４，４，５，５−テトラクロロペンタン−３−
オール14.09ｇ（0.05モル）を無水プロピオン酸
39.05ｇ（0.30モル）と60゜Beリン酸2.26ｇ（0.02
モル）の混合液中に０〜−５℃で30分かかつて滴
下する。滴下後、反応液は90〜95℃の温度で３時
間反応させた。反応後、実施例１と同様に処理し
て粗油19.94ｇを得た。粗油を分留して沸点110.0
℃／７mmHg（d20 41.3458、n20 D1.4847、Cl50.09％）
の３−プロピオニルオキシ−４，４，５，５−テ
トラクロロペンタン11.29ｇ（収率80.0％）を得
た。
実施例 ４
２−メチル−３，３，４，４−テトラクロロブ
タン−２−オール14.09ｇ（0.05モル）を無水プ
ロピオン酸39.05ｇ（0.30モル）を60゜Beリン酸
2.26ｇ（0.02モル）の混合液中に０〜−５℃で30
分かかつて滴下する。滴下後、反応液を90〜95℃
で３時間反応させた。反応後、実施例１と同様に
処理して粗油37.69ｇを得た。これに分留して沸
点124〜126.0℃／10mmHg（Cl50.13％）の２−プロ
ピオニルオキシ−２−メチル−３，３，４，４−
テトラクロロブタン14.05ｇ（収率100％）を得
た。
実施例 ５
５，５，６，６−テトラクロロヘキサン−４−
オール14.80ｇ（0.05モル）を無水プロピオン酸
39.05ｇ（0.30モル）と60゜Beリン酸2.26ｇ（0.02
モル）の混合液に０〜−５℃で30分かかつて滴下
する。滴下後、反応液を90〜95℃で３時間反応さ
せた。反応後、実施例１と同様に処理して粗油
21.62ｇを得た。これを分留して沸点120.0℃／７
mmHg（d20 41.3071、n20 D1.4824、Cl47.88％）の４−
プロピオニルオキシ−５，５，６，６−テトラク
ロロヘキサン14.80ｇ（収率100％）を得た。[Formula] (In the formula, R 1 , R 2 , X 1 , X 2 , X 3 and X 4 have the same meanings as above) is added to a mixture of propionic anhydride and phosphoric acid. It is characterized by causing a heating reaction after dropping. general formula This is a method for producing a halogenated propionic acid ester represented by the formula (R 1 , R 2 , X 1 , X 2 , X 3 and X 4 have the same meanings as above). The halogenated alcohol used as a raw material in the method of the present invention may be linear or branched, but it is appropriate that the halogenated alcohol has 3 to 10 carbon atoms. As the halogen, a fluorine atom, a chlorine atom, a bromine atom, etc. are used. As the phosphoric acid to be mixed with propionic anhydride, 60°Be is used, and in some cases, metaphosphoric acid and polyphosphoric acid can be used in combination. However, when the concentration of phosphoric acid is high, compounds with unsaturated bonds (),
() generates. Therefore, it was found that the reaction to () and () can be suppressed as much as possible by mixing propionic anhydride and phosphoric acid and then reacting them dropwise with a halogenated alcohol. The proportion of propionic anhydride is suitably 1 to 10 per 1 of the halogenated alcohol, most preferably 5 to 6.
If this ratio is low, the formation of by-products will increase. It is sufficient that the phosphoric acid has a temperature of 60°C Be, and is suitably in an amount of about 30 to 40 mol % based on the raw material halogenated alcohol. Reaction time is 1-3 hours and temperature is 90-90℃.
100℃ is sufficient. The halogenated propionate ester of the present invention is
It is used as an insect attractant and in the production of flame retardants by bromination. It is also dehalogenated to form an acetylene compound, which is useful as a raw material for the synthesis of organic heat storage agents that can store light energy. Next, the present invention will be explained in more detail with reference to Examples. Example 1 2,2,3,3-tetrachloropropane-1-
All 12.69g (0.05mol) of propionic anhydride
39.05g (0.30mol) and 2.26g (0.02mol) of 60°Be phosphoric acid
mol) at 0 to -5°C for 30 minutes. After the dropwise addition, the temperature of the reaction solution was gradually raised to 90 to 95° C., and then heated and reacted at that temperature for 3 hours. After the reaction, it is decomposed in ice water and extracted with carbon tetrachloride. The extract was washed with an acidic sodium hydrogen aqueous solution and a saturated sodium chloride aqueous solution, and then dried over cold nitrogen. Carbon tetrachloride and unreacted propionic acid were distilled off from the extract to obtain 19.80 g of crude oil. Distill crude oil to obtain a fraction with a boiling point of 46.0 to 108.0℃/10mmHg
17.63g was obtained. This is fractionated and the boiling point is 95.0℃/7
12.10 g (yield 95.3%) of a fraction of mmHg (d 20 4 1.4213, n 20 D 1.4824) was obtained. The elemental analysis value of this fraction is
Molecular formula: H: 3.09; C: 28.58; Cl: 55.73
Elemental analysis value of C 6 H 8 O 2 Cl 4 H: 3.17; C: 28.37;
Cl: agrees well with the value of 55.84. In addition, the infrared absorption spectrum shows a strong stretching vibration of C=O of the carbonyl of the ester at a wave number of 1753 cm -1 , and the target 1-
Propionyloxy-2,2,3,3-tetrachloropropane. Example 2 13.39 g (0.05 mol) of 3,3,4,4-tetrachlorobetan-2-ol was added to propionic anhydride.
39.05g (0.30mol) and 2.26g (0.02mol) of 60°Be phosphoric acid
mol) at 0 to -5°C for 30 minutes. After the dropwise addition, the reaction solution was gradually raised to a temperature of 90 to 95°C, and then reacted at that temperature for 3 hours.
After the reaction, 24.16g of crude oil was processed in the same manner as in Example 1.
I got it. Distill crude oil to boiling point 45.0-112.0℃/10
17.06 g of mmHg fraction was obtained. This was further fractionated to obtain a boiling point of 101.0℃/7mmHg (d 20 4 1.3849, n 20 D 1.4828,
2-propionyloxy-3,3,
4,4-tetrachlorobutane 11.77g (yield 87.8
%) was obtained. Example 3 4,4,5,5-tetrachloropentane-3-
All 14.09g (0.05mol) of propionic anhydride
39.05g (0.30mol) and 2.26g (0.02mol) of 60°Be phosphoric acid
mol) at 0 to -5°C for 30 minutes. After the dropwise addition, the reaction solution was allowed to react at a temperature of 90 to 95°C for 3 hours. After the reaction, the mixture was treated in the same manner as in Example 1 to obtain 19.94 g of crude oil. Fractional distillation of crude oil to boiling point 110.0
℃/7mmHg (d 20 4 1.3458, n 20 D 1.4847, Cl50.09%)
11.29 g (yield: 80.0%) of 3-propionyloxy-4,4,5,5-tetrachloropentane was obtained. Example 4 14.09 g (0.05 mol) of 2-methyl-3,3,4,4-tetrachlorobutan-2-ol was mixed with 39.05 g (0.30 mol) of propionic anhydride and 60° Be phosphoric acid.
2.26 g (0.02 mol) in a mixed solution at 0 to -5°C.
Drips within minutes. After dropping, heat the reaction solution to 90-95℃.
The mixture was allowed to react for 3 hours. After the reaction, it was treated in the same manner as in Example 1 to obtain 37.69 g of crude oil. This was fractionated to produce 2-propionyloxy-2-methyl-3,3,4,4- with a boiling point of 124-126.0℃/10mmHg (Cl50.13%).
14.05 g (yield 100%) of tetrachlorobutane was obtained. Example 5 5,5,6,6-tetrachlorohexane-4-
All 14.80g (0.05mol) of propionic anhydride
39.05g (0.30mol) and 2.26g (0.02mol) of 60°Be phosphoric acid
mol) at 0 to -5°C for 30 minutes. After the dropwise addition, the reaction solution was reacted at 90 to 95°C for 3 hours. After the reaction, the crude oil was processed in the same manner as in Example 1.
21.62g was obtained. This is fractionated and the boiling point is 120.0℃/7
4- of mmHg (d 20 4 1.3071, n 20 D 1.4824, Cl47.88%)
14.80 g (yield 100%) of propionyloxy-5,5,6,6-tetrachlorohexane was obtained.
Claims (1)
X1、X2X3およびX4はハロゲン原子である）のハ
ロゲン化アルコールを無水プロピオン酸とリン酸
の混合液中で反応させ 一般式 【式】 （R1、R2、X1、X2、X3およびX4は前記と同じ
意味を持つ）で表わされるハロゲン化プロピオン
酸エステルの製法。[Claims] 1 General formula [Formula] (In the formula, R 1 and R 2 are hydrogen atoms or alkyl groups,
X 1 , X 2 , X 3 and X 4 are halogen atoms) are reacted in a mixture of propionic anhydride and phosphoric acid. 2 , X 3 and X 4 have the same meanings as above).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58014816A JPS59141538A (en) | 1983-02-01 | 1983-02-01 | Production of halogenated propionic acid ester |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58014816A JPS59141538A (en) | 1983-02-01 | 1983-02-01 | Production of halogenated propionic acid ester |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59141538A JPS59141538A (en) | 1984-08-14 |
| JPH0138776B2 true JPH0138776B2 (en) | 1989-08-16 |
Family
ID=11871560
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58014816A Granted JPS59141538A (en) | 1983-02-01 | 1983-02-01 | Production of halogenated propionic acid ester |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59141538A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4590292A (en) * | 1985-06-10 | 1986-05-20 | Ciba-Geigy Corporation | Process for the manufacture of cyclopropylamine |
| NO165188C (en) * | 1986-12-22 | 1991-01-09 | Atochem | SYNTHESIS OF 1,1,2,2-TETRAHYDROPERFLUORAL CHANNELS AND THEIR ESTERS. |
-
1983
- 1983-02-01 JP JP58014816A patent/JPS59141538A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS59141538A (en) | 1984-08-14 |
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