KR100287363B1 - Method for preparing 1,1-difluoroethylmethyl ether - Google Patents

Method for preparing 1,1-difluoroethylmethyl ether Download PDF

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KR100287363B1
KR100287363B1 KR1019980038445A KR19980038445A KR100287363B1 KR 100287363 B1 KR100287363 B1 KR 100287363B1 KR 1019980038445 A KR1019980038445 A KR 1019980038445A KR 19980038445 A KR19980038445 A KR 19980038445A KR 100287363 B1 KR100287363 B1 KR 100287363B1
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ether
difluoroethylene
difluoroethylmethyl
preparing
alkali carbonate
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KR20000020035A (en
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이현주
김훈식
김홍곤
안병성
이병권
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박호군
한국과학기술연구원
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/05—Preparation of ethers by addition of compounds to unsaturated compounds
    • C07C41/06—Preparation of ethers by addition of compounds to unsaturated compounds by addition of organic compounds only
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
    • C07C43/04—Saturated ethers
    • C07C43/115—Saturated ethers containing carbocyclic rings

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Abstract

M2CO3(M=알칼리금속)의 일반식을 가지는 탄산알칼리의 촉매하에서, 1,1-디플루오로에틸렌과 메탄올을 반응시켜 1,1-디플루오로에틸메틸에테르를 제조하는 방법에 관한 것이다. 본 발명에 따른 신규의 디플루오로메틸에테르의 제조방법은 탄산알칼리 촉매를 사용함으로써, 강염기를 사용한 종래의 제조방법을 개선하여, 장치의 부식을 막고, 부산물의 생성을 감소시키고, 고수율의 산물을 얻을 수 있는 장점이 있다.A method for producing 1,1-difluoroethylmethyl ether by reacting 1,1-difluoroethylene and methanol under a catalyst of alkali carbonate having a general formula of M 2 CO 3 (M = alkali metal) will be. The novel method for producing difluoromethyl ether according to the present invention improves the conventional production method using a strong base by using an alkali carbonate catalyst, thereby preventing corrosion of the device, reducing the formation of by-products, and high yield products. There is an advantage to get it.

Description

1,1-디플루오로에틸메틸에테르의 제조방법Method for preparing 1,1-difluoroethylmethyl ether

본 발명은 탄산알칼리의 존재하에서 디플루오로에틸메틸에테르(CH3CF2OCH3)의 제조방법에 관한 것으로서, 더욱 자세하게는 탄산알칼리의 존재하에서 1,1-디플루오로에틸렌(CF2=CH2)과 메탄올을 반응시켜 1,1-디플루오로에틸메틸에테르(CH3CF2OCH3)를 제조하는 방법에 관한 것이다. 본 발명에 따라 제조된 1,1-디플루오로에틸메틸에테르는 불화에테르 화합물의 일종으로서, 분자내에 염소를 포함하지 않으므로 오존층을 파괴하지 않고 또한 온실효과도 없다. 따라서 제 3세대 CFC대체물질로 유용하다고 알려져 있다.The present invention relates to a method for preparing difluoroethyl methyl ether (CH 3 CF 2 OCH 3 ) in the presence of alkali carbonate, more specifically 1,1-difluoroethylene (CF 2 = CH in the presence of alkali carbonate) 2 ) and methanol to react to produce a 1,1-difluoroethylmethyl ether (CH 3 CF 2 OCH 3 ). The 1,1-difluoroethylmethyl ether produced according to the present invention is a kind of fluorinated ether compound, and does not contain chlorine in its molecule, and thus does not destroy the ozone layer and has no greenhouse effect. Therefore, it is known to be useful as a third generation CFC substitute.

본 발명에 따라 제조된 화합물인 1,1-디플루오로에틸메틸에테르(CH3CF2OCH3)는 분자 내에 수소원자와 산소원자를 동시에 가지고 있어 대기중의 히드록시 라디칼과의 반응성이 크기 때문에 대류권에서 쉽게 분해되는 성질이 있으며, 종래의 CFC-11, CFC-12등과 같은 수준으로 열적 안정성이 우수하고, 고분자화합물에 대한 용해도가 적어 발포제나 분사제뿐만 아니라 냉동기나 열펌프 등에 사용될 수 있으므로 기존 CFC-11, 12, 114의 대체품으로 유용하다.1,1-difluoroethylmethyl ether (CH 3 CF 2 OCH 3 ), a compound prepared according to the present invention, has a hydrogen atom and an oxygen atom in the molecule at the same time, and thus has high reactivity with hydroxy radicals in the atmosphere. It is easily decomposed in the troposphere, and has the same thermal stability as CFC-11, CFC-12, etc. Useful as a replacement for CFC-11, 12, 114.

함불소에테르를 제조하는 방법은 여러 가지가 있는데, 에테르 화합물을 불소화하는 방법과 불소원자를 함유한 화합물을 이용하여 에테르를 제조하는 방법으로 크게 분류할 수 있다. 첫 번째로, 에테르 화합물을 불소화하는 방법으로는 불소(F2)가스를 이용하는 방법(미국특허 제 3,897,502호), 금속불화물을 이용하는 방법(일본특허공개공보 평6-192154), 전해불소화법(미국특허 5,474,657호) 등이 알려져 있고, 두 번째로 불소원자를 함유한 화합물을 이용하여 에테르를 제조하는 방법으로는 함불소 올레핀의 알콜 첨가반응(일본특허 공개공보 평7-25803호), 알콜과 알킬할라이드의 반응(유럽특허 B1 0 603 002호), 그리고 함불소알콜과 술폰산에스테르의 반응(유럽특허 B1 0 814 493호)등이 알려져 있다.There are several methods for producing fluorine-containing ethers, which can be broadly classified into a method of fluorinating an ether compound and a method of preparing ether using a compound containing a fluorine atom. First, as a method of fluorinating an ether compound, a method using fluorine (F 2 ) gas (US Pat. No. 3,897,502), a method using metal fluoride (JP-A-6-192154), an electrofluorination method (US Patent 5,474, 657) and the like, and secondly, the method of preparing ether using a compound containing a fluorine atom includes alcohol addition reaction of fluorine-containing olefins (Japanese Patent Laid-Open Publication No. H7-25803), alcohol and alkyl. The reaction of a halide (European patent B1 0 603 002), and the reaction of a fluorine-containing alcohol and sulfonic acid ester (European patent B1 0 814 493), etc. are known.

일본특허 공개공보 평 7-25803호에는 1,1-디플루오로에틸렌(CF2=CH2)을 메탄올과 반응시켜 1,1-디플루오로에틸메틸에테르를 제조하는 방법이 기재되어 있고, 일본특허 공개공보 평 7-48306호에는 1,1-디플루오로에틸렌(CF2=CH2)을 2,2-디플루오로에탄올(CF2HCH2OH)과 반응시켜 1,1-디플루오로에틸-2,2-디플루오로에틸에테르(CHF2CH2OCF2CH3)를 제조하는 방법에 대하여 기재되어 있다. 또한 일본특허 공개공보 평 7-41447호에는 디플루오로에탄올(CF2HCH2OH)을 트리플루오로에틸렌(CF2=CFH)에 첨가시켜 2,2-디플루오로에틸-1,1,2-트리플루오로에틸에테르를 제조하는 방법이 보고되어 있다.Japanese Patent Laid-Open No. 7-25803 describes a method for producing 1,1-difluoroethylmethyl ether by reacting 1,1-difluoroethylene (CF 2 = CH 2 ) with methanol, and Japan Patent Publication No. 7-48306 discloses 1,1-difluoroethylene by reacting 1,1-difluoroethylene (CF 2 = CH 2 ) with 2,2-difluoroethanol (CF 2 HCH 2 OH). A method for preparing ethyl-2,2-difluoroethyl ether (CHF 2 CH 2 OCF 2 CH 3 ) is described. In addition, Japanese Patent Application Laid-open No. Hei 7-41447 adds difluoroethanol (CF 2 HCH 2 OH) to trifluoroethylene (CF 2 = CFH) to give 2,2-difluoroethyl-1,1,2 A method for preparing trifluoroethyl ether has been reported.

이상의 방법들은 모두 원료인 에틸렌에 대해 당량 이상의 수산화나트륨(NaOH)이나 수산화칼륨(KOH)을 사용하여 50 - 100℃에서 12 - 20시간의 장시간 반응을 통하여 에테르를 제조하고 있는데, 이러한 강염기의 사용은 반응기의 부식을 유발하는 단점을 가지고 있다.All of the above methods produce ethers for a long time of 12-20 hours at 50-100 ℃ using sodium hydroxide (NaOH) or potassium hydroxide (KOH) equivalent to the raw material ethylene. It has the disadvantage of causing corrosion of the reactor.

종래의 디플루오로에틸에테르를 제조하는 방법은 과량의 강염기의 사용으로 인한 장치 부식문제를 줄이고, 고수율의 산물을 얻는 1,1-디플루오로에틸메틸에테르의 신규한 제조방법을 제공하는 것이다.The conventional method for preparing difluoroethyl ether is to provide a novel method for preparing 1,1-difluoroethylmethyl ether, which reduces the problem of device corrosion caused by the use of excess strong bases and yields high yield products. .

본 발명자들은 탄산알칼리를 촉매로 하여 1,1-디플루오로에틸렌을 메탄올과 반응시켜 고수율의 1,1-디플루오로에틸메틸에테르를 제조하는 방법을 제공하는 것이다.The present inventors provide a method for producing high yield of 1,1-difluoroethylmethyl ether by reacting 1,1-difluoroethylene with methanol using alkali carbonate as a catalyst.

본 발명은 디플루오로에틸메틸에테르(CH3CF2OCH3)의 제조방법에 관한 것으로서, 더욱 자세하게는 탄산알칼리의 존재하에서 1,1-디플루오로에틸렌(CF2=CH2)과 메탄올을 반응시켜 1,1-디플루오로에틸메틸에테르(CH3CF2OCH3)를 제조하는 방법에 관한 것이다. 본 발명에 따라 제조된 1,1-디플루오로에틸메틸에테르는 불화에테르 화합물의 일종으로서, 분자내에 염소를 포함하지 않으므로 오존층을 파괴하지 않고 또한 온실효과도 없다. 따라서 제 3세대 CFC대체물질로 유용하다고 알려져 있다.The present invention relates to a method for preparing difluoroethylmethyl ether (CH 3 CF 2 OCH 3 ), and more particularly to 1,1-difluoroethylene (CF 2 = CH 2 ) and methanol in the presence of alkali carbonate. Reaction relates to a method for producing 1,1-difluoroethylmethyl ether (CH 3 CF 2 OCH 3 ). The 1,1-difluoroethylmethyl ether produced according to the present invention is a kind of fluorinated ether compound, and does not contain chlorine in its molecule, and thus does not destroy the ozone layer and has no greenhouse effect. Therefore, it is known to be useful as a third generation CFC substitute.

본 발명자들은 탄산알칼리를 촉매로 하여 1,1-디플루오로에틸렌을 메탄올과 반응시켜 고수율의 1,1-디플루오로에틸메틸에테르를 합성할 수 있음을 발견하였다.The present inventors found that 1,1-difluoroethylmethyl ether of high yield can be synthesized by reacting 1,1-difluoroethylene with methanol using alkali carbonate as a catalyst.

본 발명에 이용되는 탄산알칼리는 Li,Na, K, Rb,Cs등의 탄산염이 사용될 수 있고 사용량은 원료 1,1-디플루오로에틸렌에 대해 0.1 - 50몰%, 바람직하게는 1 - 20몰%이다. 촉매의 사용량이 0.1몰% 미만이면 반응의 수율이 너무 낮고, 50몰%를 초과하면 부산물이 많이 생성되고 필요 이상의 염기를 사용하게 되므로 비경제적이다.Alkaline carbonate used in the present invention can be used carbonates such as Li, Na, K, Rb, Cs and the like amount is 0.1 to 50 mol%, preferably 1 to 20 mol relative to the raw material 1,1-difluoroethylene %to be. If the amount of the catalyst used is less than 0.1 mol%, the yield of the reaction is too low, and if it exceeds 50 mol%, it is uneconomical because many by-products are generated and more than necessary bases are used.

본 발명에서 반응 원료인 동시에 용매로 사용되는 메탄올의 양은 염기의 용해도 및 반응 속도를 고려할 때 1,1-디플루오로에틸렌의 당량비 이상이 바람직하다.In the present invention, the amount of methanol used as a reaction material and a solvent is preferably higher than the equivalent ratio of 1,1-difluoroethylene in consideration of the solubility of the base and the reaction rate.

본 발명의 반응온도는 0 - 200℃ 범위로 선택할 수 있으나 30 - 150℃의 범위가 적당하다. 이 온도범위를 벗어나면 반응속도가 현저히 증가하지 아니할 뿐만 아니라 부산물의 생성 등의 좋지못한 결과가 초래된다.The reaction temperature of the present invention can be selected from 0 to 200 ℃ range, but 30 to 150 ℃ range is suitable. Beyond this temperature range, the reaction rate does not increase markedly, and the bad results such as the formation of by-products are caused.

이하에서 실시예를 들어 본 발명을 보다 상세하게 설명하나, 본 발명의 범위가 이들 실시예로 한정되는 것은 아니다.Although an Example is given to the following and this invention is demonstrated to it in more detail, the scope of the present invention is not limited to these Examples.

실시예Example

실시예 1Example 1

100ml 고압 반응기에 K2CO3(2.78g, 0.02mmol)와 메탄올(64g, 2mol)을 채운 후 1,1-디플루오로에틸렌(12.8g, 0.2mol)을 주입하고 80℃에서 3시간 반응시켰다. 반응 혼합물을 0℃로 냉각 후 GC 및 GC-Mass로 분석한 결과, 1,1-디플루오로에틸렌의 전환율은 47.9%이고 1,1-디플루오로에틸메틸에테르의 선택율은 99.8%였다.K 2 CO 3 (2.78g, 0.02mmol) and methanol (64g, 2mol) were charged in a 100ml high pressure reactor, 1,1-difluoroethylene (12.8g, 0.2mol) was charged and reacted at 80 ° C for 3 hours. . After cooling the reaction mixture to 0 ° C. and analyzing by GC and GC-Mass, the conversion of 1,1-difluoroethylene was 47.9% and the selectivity of 1,1-difluoroethylmethyl ether was 99.8%.

실시예 2-5Example 2-5

실시예 1과 동일한 조건에서 탄산알칼리에서 염기의 종류를 변화시키면서 반응실험을 행한 결과를 표 1에 나타내었다.Table 1 shows the results of the reaction experiments while varying the type of base in alkali carbonate under the same conditions as in Example 1.

M2CO3 M 2 CO 3 1,1-디플루오로에틸렌의 전환율(%)% Conversion of 1,1-difluoroethylene 1,1-디플루오로에틸렌 메틸에테르의 선택율(%)% Selectivity of 1,1-difluoroethylene methyl ether 실시예 2Example 2 Li2CO3 Li 2 CO 3 5.15.1 99.999.9 실시예 3Example 3 Na2CO3 Na 2 CO 3 16.716.7 99.799.7 실시예 4Example 4 Rb2CO3 Rb 2 CO 3 56.456.4 99.299.2 실시예 5Example 5 Cs2CO3 Cs 2 CO 3 68.668.6 99.899.8

실시예 6-10Example 6-10

실시예 1과 동일한 조건에서 탄산알칼리의 양을 변화시키면서 반응실험을 행한 결과 표 2에 나타내었다.Table 2 shows the results of the reaction experiments under varying amounts of alkali carbonate under the same conditions as in Example 1.

M2CO3 M 2 CO 3 M2CO3(몰%)M 2 CO 3 (mol%) 1,1-디플루오로에틸렌의 전환율(%)% Conversion of 1,1-difluoroethylene 1,1-디플루오로에틸렌 메틸에테르의 선택율(%)% Selectivity of 1,1-difluoroethylene methyl ether 실시예 6Example 6 Na2CO3 Na 2 CO 3 1One 0.40.4 99.399.3 실시예 7Example 7 Na2CO3 Na 2 CO 3 2020 25.925.9 99.499.4 실시예 8Example 8 K2CO3 K 2 CO 3 1One 6.36.3 99.899.8 실시예 9Example 9 K2CO3 K 2 CO 3 55 23.423.4 99.299.2 실시예 10Example 10 K2CO3 K 2 CO 3 2020 79.579.5 98.698.6

실시예 11-16Example 11-16

실시예 1과 동일한 조건에서 반응온도를 변화시키면서 반응실험을 행한 결과 표 3에 나타내었다.Table 3 shows the results of the reaction experiments under varying reaction temperatures under the same conditions as in Example 1.

M2CO3 M 2 CO 3 반응온도(℃)Reaction temperature (℃) 1,1-디플루오로에틸렌의 전환율(%)% Conversion of 1,1-difluoroethylene 1,1-디플루오로에틸렌 메틸에테르의 선택율(%)% Selectivity of 1,1-difluoroethylene methyl ether 실시예 11Example 11 Li2CO3 Li 2 CO 3 100100 3.53.5 99.899.8 실시예 12Example 12 Na2CO3 Na 2 CO 3 120120 28.328.3 99.399.3 실시예 13Example 13 Na2CO3 Na 2 CO 3 150150 51.251.2 98.498.4 실시예 14Example 14 K2CO3 K 2 CO 3 3030 7.47.4 99.299.2 실시예 15Example 15 K2CO3 K 2 CO 3 120120 62.862.8 98.998.9 실시예 16Example 16 K2CO3 K 2 CO 3 150150 77.877.8 94.194.1

종래의 강염기를 사용하는 디플루오로에틸메틸에테르의 제조방법과 달리, 본 발명은 촉매량의 탄산알칼리의 존재하에 1,1-디플루오로에틸렌을 메탄올과 반응시켜 1,1-디플루오로에틸메틸에테르를 제조하는 방법을 제공함으로써, 과량의 강염기의 사용으로 인한 문제점인 장시간 반응, 장치 부식를 해결하고, 부산물의 생성을 감소시키고, 고수율의 산물을 얻을 수 있는 장점이 있다. 또한 본 발명에 따라 제조된 고수율의 1,1-디플루오로에틸메틸에테르는 열적 안정성이 우수하고, 고분자 화합물에 대한 용해도가 낮아 제 3세대 CFC대체물질로 유용하다.Unlike the conventional method for preparing difluoroethyl methyl ether using a strong base, the present invention reacts 1,1-difluoroethylene with methanol in the presence of a catalytic amount of alkali carbonate to 1,1-difluoroethylmethyl By providing a method of preparing the ether, there is an advantage that can solve the long-term reaction, device corrosion, which is a problem caused by the use of excess strong base, reduce the production of by-products, and obtain a high yield of the product. In addition, the high yield of 1,1-difluoroethylmethyl ether prepared according to the present invention is excellent as a thermal stability, low solubility in the high molecular compound is useful as a third generation CFC substitute.

Claims (4)

촉매량의 탄산알칼리의 존재하에 1,1-디플루오로에틸렌을 메탄올과 반응시켜 1,1-디플루오로에틸메틸에테르를 제조하는 방법.A process for producing 1,1-difluoroethylmethyl ether by reacting 1,1-difluoroethylene with methanol in the presence of a catalytic amount of alkali carbonate. 제 1 항에 있어서, 상기의 탄산알칼리가 Li2CO3,Na2CO3,K2CO3,Rb2CO3,Cs2CO3인 것을 특징으로 하는 방법.The method according to claim 1, wherein the alkali carbonate is Li 2 CO 3 , Na 2 CO 3 , K 2 CO 3 , Rb 2 CO 3 , Cs 2 CO 3 . 제 1 항에 있어서, 상기 탄산알칼리의 촉매량이 디플루오로에틸렌의 1-20몰%인 것을 특징으로 하는 방법.The method according to claim 1, wherein the catalytic amount of alkali carbonate is 1-20 mol% of difluoroethylene. 제 1 항에 있어서, 반응온도가 30-150℃인 것을 특징으로 하는 방법.The method of claim 1 wherein the reaction temperature is 30-150 ° C.
KR1019980038445A 1998-09-17 1998-09-17 Method for preparing 1,1-difluoroethylmethyl ether KR100287363B1 (en)

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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0725803A (en) * 1992-08-11 1995-01-27 Agency Of Ind Science & Technol 1,1-difluoroethyl methyl ether and its production and working fluid containing the same
JPH09208513A (en) * 1996-01-30 1997-08-12 Kao Corp Production of allyl perfluoroalkyl ether

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0725803A (en) * 1992-08-11 1995-01-27 Agency Of Ind Science & Technol 1,1-difluoroethyl methyl ether and its production and working fluid containing the same
JPH09208513A (en) * 1996-01-30 1997-08-12 Kao Corp Production of allyl perfluoroalkyl ether

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