CN1156434C - 8-烷基-8-三环癸基5-降冰片烯-2-羧酸酯及其制备方法 - Google Patents
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- 238000000034 method Methods 0.000 title claims abstract description 9
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 title claims description 12
- -1 norbornene carboxylate compound Chemical class 0.000 claims abstract description 22
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 5
- 238000006243 chemical reaction Methods 0.000 claims description 25
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 claims description 18
- FWLDHHJLVGRRHD-UHFFFAOYSA-N decyl prop-2-enoate Chemical compound CCCCCCCCCCOC(=O)C=C FWLDHHJLVGRRHD-UHFFFAOYSA-N 0.000 claims description 9
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 8
- 239000007818 Grignard reagent Substances 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 4
- 150000004795 grignard reagents Chemical class 0.000 claims description 4
- NPSSWQJHYLDCNV-UHFFFAOYSA-N prop-2-enoic acid;hydrochloride Chemical compound Cl.OC(=O)C=C NPSSWQJHYLDCNV-UHFFFAOYSA-N 0.000 claims description 4
- 238000005698 Diels-Alder reaction Methods 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 239000003153 chemical reaction reagent Substances 0.000 claims description 3
- 229910052744 lithium Inorganic materials 0.000 claims description 3
- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 claims description 3
- YCCXQARVHOPWFJ-UHFFFAOYSA-M magnesium;ethane;chloride Chemical compound [Mg+2].[Cl-].[CH2-]C YCCXQARVHOPWFJ-UHFFFAOYSA-M 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- 229910001623 magnesium bromide Inorganic materials 0.000 claims description 2
- FYGUSUBEMUKACF-UHFFFAOYSA-N bicyclo[2.2.1]hept-2-ene-5-carboxylic acid Chemical compound C1C2C(C(=O)O)CC1C=C2 FYGUSUBEMUKACF-UHFFFAOYSA-N 0.000 abstract 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 238000002360 preparation method Methods 0.000 description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 125000005574 norbornylene group Chemical group 0.000 description 6
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 239000003063 flame retardant Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000013019 agitation Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 230000005311 nuclear magnetism Effects 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 2
- JZEPSDIWGBJOEH-UHFFFAOYSA-N 4-decylbicyclo[2.2.1]hept-2-ene Chemical group C1CC2C=CC1(CCCCCCCCCC)C2 JZEPSDIWGBJOEH-UHFFFAOYSA-N 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 238000003747 Grignard reaction Methods 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 150000001334 alicyclic compounds Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
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- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C69/753—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring of polycyclic acids
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
- C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C67/347—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by addition to unsaturated carbon-to-carbon bonds
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- C07C2603/58—Ring systems containing bridged rings containing three rings
- C07C2603/60—Ring systems containing bridged rings containing three rings containing at least one ring with less than six members
- C07C2603/66—Ring systems containing bridged rings containing three rings containing at least one ring with less than six members containing five-membered rings
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Abstract
本发明提供了一种降冰片烯羧酸酯化合物及其制备方法。该降冰片烯羧酸酯化合物为分子式(1)所示的8-烷基-8-三环癸基5-降冰片烯-2-羧酸酯,其中R为甲基或乙基。
Description
本发明涉及-种新型降冰片烯羧酸酯化合物及其制备方法,尤其是涉及8-烷基-8-三环癸基5-降冰片烯-2-羧酸酯化合物及其制备方法。
降冰片烯是二环[2.2.1]-2-庚烯的俗称,是一种脂环烃化合物,由于其环状双键具有很高的反应活性,因此广泛用在各种化学反应中。特别地,在带有引入降冰片烯的羧基的降冰片烯羧酸酯化合物中,降冰片烯很容易被大的取代基取代。特别地,含有脂环化合物(低化学反应活性)的大取代基应用很广泛。
带有大的脂环取代基的降冰片烯化合物工业化用作各种阻燃剂。此外,带有大的脂环取代基的降冰片烯化合物能够与现有单体共聚,然后用作聚合物阻燃剂。因此,带有大取代基的降冰片烯化合物的制备受到了很大关注。
但是,普通带有大的脂肪族取代基的降冰片烯羧酸酯化合物反应条件很难控制,导致产率低且不易提纯。因此,工业化制备普通降冰片烯羧酸酯化合物是很困难的。
为了解决上述问题,本发明的一个目的是提供一种降冰片烯羧酸酯化合物,其能够通过简单的适于工业化制备的方法制备和提纯。
本发明的另一个目的是提供一种制备降冰片烯羧酸酯化合物的方法。
此外,为了达到第一个目的,本发明提供下述式(1)表示的8-烷基-8-三环癸基5-降冰片烯-2-羧酸酯:
其中R为甲基或乙基。
为了达到第二个目的,本发明提供一种制备上述式(1)所示的化合物的方法,其包括以下步骤:a)由三环癸基-8-酮与烷基格利雅试剂或烷基锂试剂反应合成8-烷基-8-三环癸醇;b)由步骤a)中合成的8-烷基-8-三环癸醇与丙烯酰氯反应合成8-烷基-8-三环癸基丙烯酸酯;c)用步骤b)中合成的8-烷基-8-三环癸基丙烯酸酯与环戊二烯进行狄尔斯-阿德耳反应。
在步骤a)中,烷基为甲基或乙基。
优选地,格利雅试剂选用烷基溴化镁或烷基氯化镁。
根据本发明,在降冰片烯化合物的制备方法中,可以在每个步骤结束以后进行分离。但是,也可以在所有步骤都进行完之后,再就地进行分离。
参考下列附图,通过本发明的优选实施例的详细描述,可以更加清楚地了解本发明的上述目的和优点:
图1是本发明实施例1中所制备的8-乙基-8-三环癸基5-降冰片烯-2-羧酸酯的NMR(核磁)谱图;
图2是本发明实施例1中所制备的8-乙基-8-三环癸基5-降冰片烯-2-羧酸酯的FT-IR(傅立叶-红外光)谱图。
优选实施例的描述
现在详细描述本发明所述的8-烷基-8-三环癸基5-降冰片烯-2-羧酸酯的制备方法。
如下面的反应流程(1)所示,由三环癸基-8-酮与烷基格利雅试剂或烷基锂试剂反应以便在三环癸基-8-酮的8位引入烷基,从而合成8-烷基-8-三环癸基醇。
[反应流程(1)]
其中R为甲基或乙基,X为Cl或Br。
考虑到侧基对反应的阻止作用和对反应产率的影响,如果想要得到8-乙基-8-三环癸基5-降冰片烯-2-羧酸酯化合物,则优选地用乙基溴化镁或乙基氯化镁作为格利雅试剂。
由于上述反应是通过普通的格利雅反应机理进行的,所以在本发明中,反应温度和压力是没有意义的。
接着,如反应流程(2)所示,由8-烷基-8-三环癸醇与丙烯酰氯反应合成8-烷基-8-三环癸基丙烯酸酯。
[反应流程(2)]
最后,如反应流程(3)所示,由8-烷基-8-三环癸基丙烯酸酯与环戊二烯进行Diels-Alder反应制备降冰片烯取代基,从而得8-烷基-8-三环癸基5-降冰片烯-2-羧酸酯。
[反应流程(3)]
下面参考下列实施例详细描述本发明,实施例是为了举例说明而不是为了限制本发明。
实施例1 8-乙基-8-三环癸基5-降冰片烯-2-羧酸酯
a.8-乙基-8-三环癸醇的合成
将440ml乙基溴化镁的四氢呋喃溶液(1.0M)用100ml四氢呋喃(THF)稀释。然后,将上述溶液倒入1升的烧瓶中,再保持在0℃下。用滴液漏斗缓慢滴入三环癸基-8-酮(60g,0.4mol),然后在搅拌下于室温反应大约12小时。反应结束后,用旋转蒸发仪除去过量THF,然后将终产物倒入水中。然后,用稀硫酸中和终产物,并用二乙基醚萃取,再然后在硫酸镁上干燥。所获得的产物通过柱状色谱法(乙烷∶乙酸乙酯=8∶1)过滤,以制备出所需产物8-乙基-8-三环癸醇(产率:70%)。b.8-乙基-8-三环癸基丙烯酸酯的合成
将8-乙基-8-三环癸醇(36g,0.2mol)和三乙基胺(0.22mol)溶解在250mlTHF中,然后用滴液漏斗缓慢滴入丙烯酰氯(19g,0.21mol)。然后,在搅拌下于室温反应大约12小时。反应结束后,用旋转蒸发仪除去过量THF,然后将终产物倒入水中。然后,用稀盐酸中和终产物,并用二乙基醚萃取,再然后在硫酸镁上干燥。所获得的产物通过柱状色谱法(己烷∶乙酸乙酯=4∶1)过滤,以制备出所需产物8-乙基-8-三环癸基丙烯酸酯(产率:80%)。
1H-NMR(CDCl3;ppm):6.3(1H,d),6.1(1H,dd),5.7(1H,d),2.5(1H,s),
2.2(2H,m),1.4(2H,d),0.8(3H,t)
FT-IR(NaCl;cm-1):2947,2863,1722,1638,1621,1402,1205C.8-乙基-8-三环癸基5-降冰片烯-2-羧酸酯的合成
将8-乙基-8-三环癸基丙烯酸酯(47g,0.2mol)溶解在250mlTHF中,在0℃下缓慢加入环戊二烯(20g,0.3mol),然后将反应温度升高到50℃左右。然后,在搅拌下反应20小时左右。反应结束后,用旋转蒸发仪除去过量的THF,然后真空蒸馏以制备出所要的无色粘稠液体(产率:90%)。图1和图2分别是该化合物的NMR和FT-IR谱图。
1H-NMR(CDCl3;ppm):6.2(1H,m),6.1(1H,s),5.9(1H,m),3.2(1H,s),
2.9(2H.m),2.4-0.8(m)
FT-IR(NaCl;cm-1): 2944,2863,1727,1335,1270,1177,712
实施例2 8-甲基-8-三环癸基5-降冰片烯-2-羧酸酯
目标化合物的制备方法同实施例1,只是用3.0M的甲基溴化镁的二乙基醚溶液代替1.0M的乙基氯化镁的THF溶液(产率:70%)。
本发明所述的8-烷基-8-三环癸基5-降冰片烯-2-羧酸酯能够通过简单的方法以很高的产率制备,且有利于工业化大批量生产。带有大取代基的降冰片烯化合物不仅可以大量用作各种类型的阻燃剂,而且能够与现有单体共聚用作聚合物阻燃剂。此外,降冰片烯在要求降冰片烯特定反应性的各种应用中是有用的。
Claims (4)
1.由下述式(1)表示的8-烷基-8-三环癸基5-降冰片烯-2-羧酸酯:
其中R为甲基或乙基。
2.制备如权利要求1所述的化合物的方法,其由下列步骤组成:
a)由三环癸-8-酮与烷基格利雅试剂或烷基锂试剂反应合成8-烷基-8-三环癸醇;
b)由步骤a)中合成的8-烷基-8-三环癸醇与丙烯酰氯反应合成8-烷基-8-三环癸基丙烯酸酯;
c)用步骤b)中合成的8-烷基-8-三环癸基丙烯酸酯与环戊二烯进行狄尔斯-阿德耳反应。
3.根据权利要求2所述的方法,其中格利雅试剂为烷基溴化镁或烷基氯化镁。
4.根据权利要求2所述的方法,其中当烷基是乙基时,格利雅试剂选用乙基溴化镁或乙基氯化镁。
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KR1020000008033A KR20010081852A (ko) | 2000-02-19 | 2000-02-19 | 8-알킬-8-트리싸이클로데카닐5-노르보르넨-2-카르복실레이트 및 그 제조방법 |
KR8033/2000 | 2000-02-19 |
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KR100441734B1 (ko) * | 1998-11-02 | 2004-08-04 | 신에쓰 가가꾸 고교 가부시끼가이샤 | 신규한 에스테르 화합물, 고분자 화합물, 레지스트 재료및 패턴 형성 방법 |
JP4529245B2 (ja) * | 1999-12-03 | 2010-08-25 | 住友化学株式会社 | 化学増幅型ポジ型レジスト組成物 |
KR20010081854A (ko) * | 2000-02-19 | 2001-08-29 | 김동석 | 8-알킬-8-트리싸이클로데카닐 (메타)아크릴레이트 및 그제조방법 |
KR20010081853A (ko) * | 2000-02-19 | 2001-08-29 | 김동석 | 2-알킬-2-아다만틸 5-노르보르넨-2-카르복실레이트 및 그제조방법 |
US6777157B1 (en) * | 2000-02-26 | 2004-08-17 | Shipley Company, L.L.C. | Copolymers and photoresist compositions comprising same |
JP2002145827A (ja) * | 2000-11-08 | 2002-05-22 | Nissan Chem Ind Ltd | 脂環式3級(メタ)アクリレート化合物及びその製造法 |
KR100865864B1 (ko) * | 2002-11-04 | 2008-10-29 | 주식회사 동진쎄미켐 | 사이클로도데실이 결합된 펜던트 기를 가지는 화학적으로증폭된 고분자와 그 제조방법, 및 이를 포함하는 레지스트조성물 |
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EP0141610B1 (en) * | 1983-10-24 | 1991-01-30 | Hitachi Chemical Co., Ltd. | Optical elements comprising polymers of (meth)acrylate esters |
EP0409291B1 (en) * | 1987-11-17 | 1996-02-14 | Japan Synthetic Rubber Co., Ltd. | Thermoplastic resin composition |
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2000
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- 2000-03-01 US US09/516,613 patent/US6153785A/en not_active Expired - Fee Related
- 2000-10-13 JP JP2000313913A patent/JP2001233833A/ja active Pending
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2001
- 2001-02-19 EP EP01301458A patent/EP1125918A1/en not_active Withdrawn
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Publication number | Publication date |
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CN1310166A (zh) | 2001-08-29 |
US6153785A (en) | 2000-11-28 |
EP1125918A1 (en) | 2001-08-22 |
JP2001233833A (ja) | 2001-08-28 |
KR20010081852A (ko) | 2001-08-29 |
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