KR100239681B1 - Fluorenylalkylsilanes and their preparation methods - Google Patents
Fluorenylalkylsilanes and their preparation methods Download PDFInfo
- Publication number
- KR100239681B1 KR100239681B1 KR1019970054145A KR19970054145A KR100239681B1 KR 100239681 B1 KR100239681 B1 KR 100239681B1 KR 1019970054145 A KR1019970054145 A KR 1019970054145A KR 19970054145 A KR19970054145 A KR 19970054145A KR 100239681 B1 KR100239681 B1 KR 100239681B1
- Authority
- KR
- South Korea
- Prior art keywords
- general formula
- iii
- represented
- silane
- silane compound
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title abstract description 6
- -1 silane compound Chemical class 0.000 claims abstract description 23
- 229910000077 silane Inorganic materials 0.000 claims abstract description 18
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000011968 lewis acid catalyst Substances 0.000 claims abstract description 10
- BXODECZHPWUQFH-UHFFFAOYSA-N 4,4-dichlorobutylsilane Chemical compound [SiH3]CCCC(Cl)Cl BXODECZHPWUQFH-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000005727 Friedel-Crafts reaction Methods 0.000 claims abstract description 7
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000001246 bromo group Chemical group Br* 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 3
- 239000002841 Lewis acid Substances 0.000 claims description 2
- 150000007517 lewis acids Chemical class 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims 1
- 229910052782 aluminium Inorganic materials 0.000 claims 1
- 239000007809 chemical reaction catalyst Substances 0.000 claims 1
- 125000005353 silylalkyl group Chemical group 0.000 claims 1
- 238000005804 alkylation reaction Methods 0.000 abstract description 6
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 abstract description 4
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 abstract description 2
- 239000002685 polymerization catalyst Substances 0.000 abstract description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 235000010290 biphenyl Nutrition 0.000 description 5
- 239000004305 biphenyl Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 150000004756 silanes Chemical class 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- XMWRBQBLMFGWIX-UHFFFAOYSA-N C60 fullerene Chemical group C12=C3C(C4=C56)=C7C8=C5C5=C9C%10=C6C6=C4C1=C1C4=C6C6=C%10C%10=C9C9=C%11C5=C8C5=C8C7=C3C3=C7C2=C1C1=C2C4=C6C4=C%10C6=C9C9=C%11C5=C5C8=C3C3=C7C1=C1C2=C4C6=C2C9=C5C3=C12 XMWRBQBLMFGWIX-UHFFFAOYSA-N 0.000 description 2
- 238000003547 Friedel-Crafts alkylation reaction Methods 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- PGPVQGBPWZXRMK-UHFFFAOYSA-N trichloro(2,3-dichlorobutyl)silane Chemical compound CC(Cl)C(Cl)C[Si](Cl)(Cl)Cl PGPVQGBPWZXRMK-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 150000004074 biphenyls Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- MTEIJBYANFASJV-UHFFFAOYSA-N dichloro-(2,3-dichlorobutyl)-methylsilane Chemical compound CC(Cl)C(Cl)C[Si](C)(Cl)Cl MTEIJBYANFASJV-UHFFFAOYSA-N 0.000 description 1
- 239000002655 kraft paper Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000007523 nucleic acids Chemical class 0.000 description 1
- 102000039446 nucleic acids Human genes 0.000 description 1
- 108020004707 nucleic acids Proteins 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/12—Organo silicon halides
- C07F7/121—Preparation or treatment not provided for in C07F7/14, C07F7/16 or C07F7/20
- C07F7/127—Preparation or treatment not provided for in C07F7/14, C07F7/16 or C07F7/20 by reactions not affecting the linkages to the silicon atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
Abstract
본 발명은 일반식 (III)으로 표시되는 신규 (풀루오레닐알킬)실란 화합물과 이의 제조방법에 관한 것으로 이는 올레핀화합물의 중합촉매에 활용될 수 있으며, 이의 제조는 일반식 (I)로 표시되는 바이페닐 유도체와 일반식 (II)로 표시되는 (디클로로부틸)실란을 루이스산 촉매하에 프리델-크라프트 알킬화 반응에 의해 일반식 (III)으로 표시되는 (풀루오레닐알킬)실란을 제조하는 것이다.The present invention relates to a novel (pluorenylalkyl) silane compound represented by the general formula (III) and a preparation method thereof, which may be utilized in a polymerization catalyst of an olefin compound, and the preparation thereof is represented by the general formula (I) The biphenyl derivative and the (dichlorobutyl) silane represented by the general formula (II) are prepared by the Friedel-Craft alkylation reaction under the Lewis acid catalyst to produce the (pulluenylalkyl) silane represented by the general formula (III).
(I) (II)(I) (II)
(III)(III)
Description
본 발명은 올레핀 화합물의 중합반응에 유용한 촉매로 사용될 수 있는 신규한 (풀루오레닐알킬)실란 화합물 및 이들의 제조방법에 관한 것이다.The present invention relates to novel (puluorenylalkyl) silane compounds that can be used as catalysts useful in the polymerization of olefin compounds and methods for their preparation.
1877년 프리델과 크라프트가 벤젠과 알킬할라이드를 알루미늄클로라이드 존재하에 반응시켜 알킬기가 첨가된 알킬벤젠을 제조하는 방법을 처음으로 발표하였으며, 그 후 이를 프리델-크라프트 반응이라 한다. 이 반응은 루이스산 존재하에 알킬기, 아실기, 아릴기 등을 벤젠 고리에 도입하는 반응으로서, 이는 산업적인 유기화합물의 제조공정에 매우 유용하게 활용되고 있다(R. M. Roberts and A. A. Khalaf, Friedel-Crafts Alkylation Chemistry, Marcel Dekker, Inc., NY, 1984).In 1877 Friedel and Kraft first presented a process for the production of alkylbenzenes to which alkyl groups were added by reacting benzene and alkyl halides in the presence of aluminum chloride, which is called the Friedel-Crafts reaction. This reaction introduces alkyl, acyl and aryl groups into the benzene ring in the presence of Lewis acid, which is very useful for the manufacturing process of industrial organic compounds (RM Roberts and AA Khalaf, Friedel-Crafts Alkylation). Chemistry, Marcel Dekker, Inc., NY, 1984).
본 발명자들은 벤젠 유도체들과 (폴리클로로알킬)실란 화합물들을 알루미늄클로라이드 등의 루이스산 촉매하에서 프리델-크라프트 알킬화 반응으로 알킬기에 치환된 염소의 숫자만큼 벤젠 유도체를 치환시켜 (폴리아릴알킬)실란 화합물을 제조할 수 있음을 발견하고 이를 출원한 바 있다(대한민국 특허출원 제 96-77559 호, 출원일자 : 1996년 12월 30일 ).The present inventors have substituted (polyarylalkyl) silane compounds by substituting benzene derivatives with the number of chlorine substituted by alkyl groups by Friedel-Craft alkylation reactions of benzene derivatives and (polychloroalkyl) silane compounds under Lewis acid catalysts such as aluminum chloride. It was found that it can be manufactured and has filed it (Korean Patent Application No. 96-77559, filed December 30, 1996).
또한, 본 발명자들은 바이페닐 유도체와 디클로로알킬실란 화합물의 프리텔-크라프트 알킬화 반응을 연구하던중 알킬화 반응으로 두개의 페닐기를 연결하는 5각형의 고리화가 일어나 풀루오렌 고리가 치환된 실란 화합물을 제조할 수 있다는 것을 발견하고 이를 출원한 바 있다(대한민국 특허출원 제 97-9346 호, 출원일자 : 1997년 3월 19일 ).In addition, the present inventors, while studying the pretel-craft alkylation reaction of a biphenyl derivative and a dichloroalkylsilane compound, a pentagonal cyclization that connects two phenyl groups by an alkylation reaction occurs to prepare a silane compound substituted with a fullerene ring. It was found and filed (Korean Patent Application No. 97-9346, filed March 19, 1997).
풀루오렌 고리가 치환된 실란 화합물은 상기 본 발명자들이 출원한 한국특허출원 제 97-9346 호에서와 같이 올레핀 중합반응의 촉매로 주목을 받고 있는 풀루오레닐 메탈로센 화합물[ Organometallics, 14, 789 (1995), J. Organomet. Chem., 508, 91 (1996) ]을 제조하는데 유용한 화합물이다.The silane compound substituted with a fullerene ring is a pulleylenyl metallocene compound that is attracting attention as a catalyst for olefin polymerization as described in Korean Patent Application No. 97-9346 filed by the present inventors [Organometallics, 14, 789 ( 1995), J. Organomet. Chem., 508, 91 (1996)] are useful compounds.
한편, 풀루오렌 유도체들은 2번과 7번 탄소 위치에 할로겐을 도입한 후에 아연 금속을 이용하여 할로겐을 제거하고 폴리풀루오렌을 제조하여 광발광 또는 전기발광 재료로 사용될 수 있다고 알려졌다[ J. Am. Chem. Soc. 118, 7416 (1996) ]. 풀루오렌의 9번 탄소에 알킬기가 도입된 유도체를 제조하기 위해서는 알킬리튬과 같은 시약을 사용하는 것이 일반적이다. 그러나 알킬리튬은 고가일 뿐만 아니라 사용시 위험이 따르므로 경제적인 방법이라 할 수 없다.On the other hand, it is known that pullulene derivatives can be used as photoluminescent or electroluminescent materials by introducing halogen at the carbon positions 2 and 7 and then removing halogen using zinc metal and preparing polypululene [J. Am. Chem. Soc. 118, 7416 (1996). It is common to use a reagent such as alkyllithium to prepare a derivative in which an alkyl group is introduced at the carbon number 9 of pullulene. However, alkyllithium is not only economical because it is expensive and risks in use.
본 발명은 일반식 (III)으로 표시되는 (풀루오레닐알킬)실란 화합물에 관한 것이다.The present invention relates to a (pluorenylalkyl) silane compound represented by the general formula (III).
본 발명은 또한 일반식 (I)로 표시되는 바이페닐 유도체와 일반식 (II)로 표시되는 (디클로로부틸)실란을 루이스산 촉매하에 프리델-크라프트 알킬화 반응에 의해 일반식 (III)으로 표시되는 (풀루오레닐알킬)실란 화합물의 제조방법에 관한 것이다.The present invention also relates to a biphenyl derivative represented by general formula (I) and a (dichlorobutyl) silane represented by general formula (II) represented by general formula (III) by a Friedel-Craft alkylation reaction under a Lewis acid catalyst ( It relates to a method for producing a pulluorenylalkyl) silane compound.
본 발명은 일반식 (III)으로 표시되는 (풀루오레닐알킬)실란 화합물에 관한 것이다.The present invention relates to a (pluorenylalkyl) silane compound represented by the general formula (III).
(III)(III)
일반식 (III)에 있어서, n은 0 ∼ 1의 정수이며, Y1와 Y2는 각각 수소, 브로모 또는 페닐이다.In general formula (III), n is an integer of 0-1, YOneWow Y2Are hydrogen, bromo or phenyl, respectively.
본 발명은 또한 일반식 (I)로 표시되는 바이페닐 유도체와 일반식 (II)로 표시되는 (디클로로부틸)실란을 루이스산 촉매하에 프리델-크라프트 알킬화 반응에 의해 일반식 (III)으로 표시되는 (풀루오레닐알킬)실란 화합물의 제조방법에 관한 것이다.The present invention also relates to a biphenyl derivative represented by general formula (I) and a (dichlorobutyl) silane represented by general formula (II) represented by general formula (III) by a Friedel-Craft alkylation reaction under a Lewis acid catalyst ( It relates to a method for producing a pulluorenylalkyl) silane compound.
(I) (II)(I) (II)
일반식 (I)에 있어서, Y1와 Y2는 각각 수소, 브로모 또는 페닐이며, 일반식 (III)에 있어서, n은 0 ∼ 1의 정수이다.In general formula (I), YOneWow Y2Are hydrogen, bromo or phenyl, respectively, and in general formula (III), n is an integer of 0-1.
일반식 (III)으로 표시되는 (풀루오레닐알킬)실란 화합물의 제조방법을 간단히 설명하면, 일반식 (I)로 표시되는 바이페닐 유도체와 일반식 (II)로 표시되는 (디클로로부틸)실란을 루이스산 촉매하에 프리델-크라프트 알킬화 반응에 의해 제조하는 것이다.A brief description will be given of the preparation method of the (pluorenyylalkyl) silane compound represented by the general formula (III). The biphenyl derivative represented by the general formula (I) and the (dichlorobutyl) silane represented by the general formula (II) It is prepared by Friedel-Crafts alkylation reaction under Lewis acid catalyst.
본 발명은 바이페닐에 두개의 염소가 치환된 부틸기가 있는 실란을 프리델-크라프트 반응으로 9번 탄소에 메틸기와 실릴에틸기가 동시에 치환된 풀루오렌 유도체를 제조하는 방법에 관한 것으로, 이를 상세히 설명하면, 일반식 (III)으로 표시되는 (풀루오레닐알킬)실란 화합물은 질소 대기하에서 일반식 (I)로 표시되는 바이페닐 유도체와 루이스산 촉매를 반응조에 넣고 일반식 (II)로 표시되는 (디클로로부틸)실란을 넣어준다. 일반식 (I)로 표시되는 바이페닐 유도체는 일반식 (II)로 표시되는 (디클로로부틸)실란에 대하여 몰비로 1 ∼ 5배를 사용하는 것이 바람직하다. 루이스산 촉매는 일반식 (II)로 표시되는 (디클로로부틸)실란에 대하여 2 - 10몰%정도 사용하는 것이 바람직하다. 반응 용매는 일반식 (I)로 표시되는 바이페닐 유도체에 따라서 사용하기도 하고 사용하지 않기도 한다. 반응조건은 25 ∼ 200℃로 유지된 온도에서 1 ∼ 12시간 정도 교반시키는 것이 바람직하다. 반응이 끝나면 루이스산 촉매를 제거한 다음 진공증류하여 원하는 목적화합물을 분리한다.The present invention relates to a method for preparing a fluoroene derivative in which a methyl group and a silylethyl group are simultaneously substituted on carbon No. 9 by a Friedel-Craft reaction of a butyl group having two chlorine substituted biphenyls. (Pluorenylalkyl) silane compound represented by the general formula (III) is a (dichlorobutyl) represented by the general formula (II) by putting a biphenyl derivative represented by the general formula (I) and a Lewis acid catalyst Add silane. As for the biphenyl derivative represented by general formula (I), it is preferable to use 1-5 times in molar ratio with respect to the (dichlorobutyl) silane represented by general formula (II). It is preferable to use about 2-10 mol% of Lewis acid catalysts with respect to the (dichlorobutyl) silane represented by General formula (II). The reaction solvent may or may not be used depending on the biphenyl derivative represented by the general formula (I). It is preferable to make reaction conditions stir for about 1 to 12 hours at the temperature maintained at 25-200 degreeC. After the reaction, the Lewis acid catalyst is removed and then vacuum distilled to separate the desired compound.
다음 실시예는 본 발명을 더욱 상세히 예증해 줄 것이나 본 발명의 범위가 이에 국한하지는 않는다.The following examples will illustrate the invention in more detail, but the scope of the invention is not limited thereto.
실시예 1Example 1
바이페닐과 (2,3-디클로로부틸)트리클로로실란의 반응Reaction of biphenyl with (2,3-dichlorobutyl) trichlorosilane
50 ml들이 삼구 둥근바닥 플라스크에 환류콘덴서와 자석 교반장치를 장치한 후 건조된 질소기체를 통과시키면서 불꽃 건조시켰다. 알루미늄클로라이드 0.33 g(2.48mmol)과 바이페닐 8.00 g(51.9mmol)을 상기 반응 플라스크에 넣었다. (2,3-디클로로부틸)트리클로로실란 3.38 g(13.0mmol)을 넣고 100℃에서 1시간 동안 교반시켰다. 반응물의 온도를 실온으로 내린뒤 POCl30.35 mol를 가하고 1시간 동안 교반시켜서 알루미늄클로라이드를 비활성화 시켰다. 반응물을 헥산으로 추출하고 이 여과액을 상압에서 증류하여 헥산을 제거하고 진공증류하여 1.49 g의 9-메틸-9-(2-트리클로로실릴에틸) 풀루오렌을 얻었다.A 50 ml three-necked round bottom flask was equipped with a reflux condenser and a magnetic stirrer, and then flame dried while passing the dried nitrogen gas. 0.33 g (2.48 mmol) of aluminum chloride and 8.00 g (51.9 mmol) of biphenyl were placed in the reaction flask. 3.38 g (13.0 mmol) of (2,3-dichlorobutyl) trichlorosilane were added thereto, followed by stirring at 100 ° C. for 1 hour. After lowering the temperature of the reaction to room temperature, 0.35 mol of POCl 3 was added and stirred for 1 hour to inactivate aluminum chloride. The reaction was extracted with hexane and the filtrate was distilled at atmospheric pressure to remove hexane and distilled under vacuum to afford 1.49 g of 9-methyl-9- (2-trichlorosilylethyl) pullulene.
끓는점 : 140 ∼ 142℃/0.2 torr,Boiling Point: 140∼142 ° C / 0.2 torr,
수율 : 34%).Yield 34%).
H-NMR(CDCl3,ppm) : 0.60 ∼ 0.66(m, SiCH2, 2H), 1.54(s, CH3, 2H), 2.24 - 2.30(m, SiCH2CH2 ,2H), 7.31 ∼ 7.40, 7.74 ∼ 7.77(m, ArH, 8H)H-NMR (CDCl 3, ppm): 0.60-0.66 (m, SiCH 2 , 2H), 1.54 (s, CH 3 , 2H), 2.24-2.30 (m, SiCH 2 CH 2 , 2H), 7.31-7.40, 7.74-7.77 (m, ArH, 8H)
실시예 2Example 2
바이페닐과 (2,3-디클로로부틸)메틸디클로로실란의 반응Reaction of Biphenyl with (2,3-Dichlorobutyl) methyldichlorosilane
50 ml들이 삼구 둥근바닥 플라스크에 환류콘덴서와 자석 교반장치를 장치한 후 건조된 질소기체를 통과시키면서 불꽃 건조시켰다. 알루미늄클로라이드 0.20 g(1.58 mmol)과 바이페닐 2.11 g(13.7mmol)을 가하고 100℃에서 1시간 동안 교반시켰다. 반응물의 온도를 실온으로 내린뒤 POCl30.275 g을 넣고 1시간 동안 교반시켜서 알루미늄클로라이드를 비활성화 시켰다. 반응물을 핵산으로 추출하고 이 여과액을 상압에서 증류하여 헥산을 제거하고 진공증류하여 0.20 g의 9-메틸-9(2-메틸디크로로실릴에틸) 풀루오렌을 얻었다.A 50 ml three-necked round bottom flask was equipped with a reflux condenser and a magnetic stirrer, and then flame dried while passing the dried nitrogen gas. 0.20 g (1.58 mmol) of aluminum chloride and 2.11 g (13.7 mmol) of biphenyl were added thereto, and the mixture was stirred at 100 ° C. for 1 hour. After the temperature of the reaction was cooled down to room temperature, 0.275 g of POCl 3 was added and stirred for 1 hour to inactivate aluminum chloride. The reaction was extracted with nucleic acid and the filtrate was distilled at atmospheric pressure to remove hexane and distilled under vacuum to yield 0.20 g of 9-methyl-9 (2-methyldichlorosilylethyl) pullulene.
끊는점 : 138 ∼ 140℃/0.2torrBreaking point: 138 ~ 140 ℃ / 0.2torr
수율 : 9%Yield: 9%
H-NMR(CDCl3, ppm): 0.67(s, SiCH3 ,3H), 1.08 ∼ 1.18(m, SiCH2, 2H), 1.61(s, CH3, 2H), 2.28 ∼ 2.33(m, SiCH2CH2 ,H), 7.31 ∼ 7.83(m, ArH, 8H)H-NMR (CDCl 3 , ppm): 0.67 (s, SiCH 3 , 3H), 1.08 to 1.18 (m, SiCH 2 , 2H), 1.61 (s, CH 3 , 2H), 2.28 to 2.33 (m, SiCH 2 CH 2 , H), 7.31-7.83 (m, ArH, 8H)
본 발명은 일반식 (III)으로 표시되는 신규 (풀루오레닐알킬)실란 화합물과 이의 제조방법에 의해 올레핀화합물의 중합촉매에 활용될 수 있다.The present invention can be utilized in the polymerization catalyst of an olefin compound by a novel (pluorenylalkyl) silane compound represented by the general formula (III) and a preparation method thereof.
Claims (6)
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1019970054145A KR100239681B1 (en) | 1997-10-22 | 1997-10-22 | Fluorenylalkylsilanes and their preparation methods |
US09/044,603 US5847182A (en) | 1997-03-19 | 1998-03-19 | Fluorenyl substituted organosilanes and their preparation methods |
JP07012598A JP3609609B2 (en) | 1997-03-19 | 1998-03-19 | Organosilane derivative substituted with fluorenyl group and method for producing the same |
DE19812191A DE19812191C2 (en) | 1997-03-19 | 1998-03-19 | Fluorenyl-substituted organosilanes and process for their preparation |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1019970054145A KR100239681B1 (en) | 1997-10-22 | 1997-10-22 | Fluorenylalkylsilanes and their preparation methods |
Publications (2)
Publication Number | Publication Date |
---|---|
KR19990032931A KR19990032931A (en) | 1999-05-15 |
KR100239681B1 true KR100239681B1 (en) | 2000-02-01 |
Family
ID=19523176
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019970054145A KR100239681B1 (en) | 1997-03-19 | 1997-10-22 | Fluorenylalkylsilanes and their preparation methods |
Country Status (1)
Country | Link |
---|---|
KR (1) | KR100239681B1 (en) |
-
1997
- 1997-10-22 KR KR1019970054145A patent/KR100239681B1/en not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
KR19990032931A (en) | 1999-05-15 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US5406013A (en) | Cyclopentadiene type compounds and method for making | |
CN100390116C (en) | Method for alpha-olefin trimerization | |
KR100239681B1 (en) | Fluorenylalkylsilanes and their preparation methods | |
US3099691A (en) | Preparation of organic phosphines from phosphorus, an alkyl halide and an organic lithium or sodium compound | |
US4814474A (en) | Method for the production of tertiary-alkyldimethylhalosilane | |
US10457696B2 (en) | Cationic silicon (II) compounds and method for the production thereof | |
EP0590539B1 (en) | Processes for producing tetrathiafulvalene derivatives and their precursors | |
KR100234006B1 (en) | Fluorenylalkylsilane chemical and the preparing method thereof | |
JP3609609B2 (en) | Organosilane derivative substituted with fluorenyl group and method for producing the same | |
JP2535794B2 (en) | Silicon-containing pentacyclic compound and method for producing the same | |
KR0139018B1 (en) | Bis silylpropyl arene and preparation process thereof | |
JP3740180B2 (en) | Method for producing biscyclopentadienyl compound | |
KR0164461B1 (en) | Derivative of polysilylalkylized benzene and process for producing it | |
US5760263A (en) | Alkylferrocenes containing chlorosilyl groups and their preparation methods | |
US5097055A (en) | Production of methylphenyltrisiloxane | |
KR100208478B1 (en) | Alkylferocenes containing chlorosilyl groups and their preparation propcess | |
JP2018145119A (en) | Method for producing alkenylsilane | |
US4847419A (en) | Process for the preparation of bifunctional tertiary aromatic phosphine sulfides, and also several specific representatives of this class of compounds | |
JP2942824B1 (en) | Silylthioalkene compound and method for producing the same | |
JPH08183791A (en) | Bis-phosphepine and its production | |
JP3385354B2 (en) | Tetrakis [bis (trifluoromethanesulfonyloxy) silyl] benzene and process for producing the same | |
JP3728905B2 (en) | Method for producing aryl halogen silane | |
JPS5931505B2 (en) | Method for producing α-halogen-substituted-γ-butyrolactones | |
JPS6250332A (en) | Polyyne polymer containing platinum and silicon in main chain and its production | |
CN115108932A (en) | Preparation method of aromatic amide compound |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A201 | Request for examination | ||
E701 | Decision to grant or registration of patent right | ||
GRNT | Written decision to grant | ||
FPAY | Annual fee payment |
Payment date: 20040910 Year of fee payment: 6 |
|
LAPS | Lapse due to unpaid annual fee |