CN1020448C - 用于制备齐格勒-纳塔催化剂的二醚 - Google Patents

用于制备齐格勒-纳塔催化剂的二醚 Download PDF

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CN1020448C
CN1020448C CN89107675A CN89107675A CN1020448C CN 1020448 C CN1020448 C CN 1020448C CN 89107675 A CN89107675 A CN 89107675A CN 89107675 A CN89107675 A CN 89107675A CN 1020448 C CN1020448 C CN 1020448C
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乔瓦尼·阿尼斯
詹彼得罗·波索蒂
朱利亚纳·斯基佩纳
伊丽莎白塔·巴巴莎
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Abstract

通式(Ⅰ)的二醚，其中：R、RⅠ、RⅡ、RⅢ、RⅣ和RⅤ可相同或不同，代表H或有1-18个碳原子的直链或支化烷基、环烷基、芳基、烷芳基或芳烷基，条件是R和RⅠ不都是H或CH3，或不是CH3和正丙基；RⅥ和RⅦ可相同或不同，代表有1-18个碳原子的直链或支化烷基、环烷基、芳基、烷芳基；R至RⅦ的一个或多个基团键接成环状结构。该二醚特别适用于制备齐格勒-纳塔催化剂。

Description

本发明是关于一类新型二醚。
本发明的二醚可用作燃料添加剂（使燃料的辛烷值增加）、溶剂、金属离子的络合剂以及用于齐格勒-纳塔催化剂的制备。
此类二醚具有下列通式：
其中：R、RⅠ、RⅡ、RⅢ、RⅣ和RⅤ可相同或不同，代表H或有1-18个碳原子的直链或支化烷基、环烷基、芳基、烷芳基或芳烷基，条件是R和RⅠ不能都是H或CH3，或不是CH3和正丙基;RⅥ和RⅦ可相同或不同，代表有1-18个碳原子的直链或支化烷基、环烷基、芳基、烷芳基;R至RⅢ的一个或多个基团可键接形成环状结构。较好的RⅥ和RⅦ是有1-6个碳原子的烷基，RⅡ、RⅢ、RⅣ和RⅤ是氢。当R和RⅠ是烷基时，它们较好的是有3个或更多个碳原子。此类新型二醚可用各种方法来制备。例如，可按如下述所列的已知醚化反应来制备，以通式Ⅱ的相应二元醇为起始原料：
Figure 891076751_IMG5
1）式Ⅱ的二元醇或相应的碱性醇化物与式RⅥ-X、RⅦ-X化合物或其混合物（其中：X为Cl、Br、I、C6H5-SO3、对CH3C6H5SO3·CH3SO3）反应，其中R、RⅠ、RⅡ、RⅢ、RⅣ和RⅤ具有前述相同的定义。
2）式Ⅱ的二元醇与式RⅥ 2SO4或RⅦ 2SO4的二烷基硫化物在碱性环境中反应。
3）用已知技术由式Ⅱ的二元醇为起始物制得的通式Ⅲ的衍生物与RⅥ-OM和RⅦ-OM醇化物（其中M为Na、K、Mg、Ca）或其混合物反应。
Figure 891076751_IMG6
其中，R至RⅤ和X具有上述定义。
4）通式（Ⅱ）的二元醇与RⅥOH或RⅦOH醇类或其混合物的混合物加热脱水或催化脱水。
上述及其它适用的方法在下列文献中有所描述：
1）Houben    Weil-Metoden    der    Organischem    Chemie    Vol    Ⅵ/3 Verlag    ed.Stuttgar    d    1965.
2）G.W.Gokel和Coll.Synthesis    1976，168.
3）G.Johns和Coll.Synthesis    1976，515.
4）D.Achet和Coll.Synthesis    1986，642.
另外，通式（Ⅱ）的二元醇可按照已知的方法合成，例如将通式Ⅵ和Ⅴ的相应二酯、二醛、二酮、酮醛或二羧酸和通式（Ⅵ）的酮酯和醛酯还原;
Figure 891076751_IMG7
其中：基团R、RⅠ、RⅡ、RⅢ具有上述定义。
这些方法的例子有：
-H.Adkins，Organic    Reactions    8，1（1954）
-N.G.Gaylord，Reduction    with    Complex    Metal    Hydrides，Interscience    Publishers，N.Y.，London    1956.
-R.F.Nystom，W.G.Brown，J.Am.Chem.Soc.69，1197（1947）。
式Ⅱ的二元醇（其中RⅡ、RⅢ、RⅣ和RⅤ是H）还可以由通式Ⅶ的醛按照坎尼扎罗（Cannizzaro）反应进行碱甲醛作用而制备，例如参见Organic Reactions第Ⅱ册，94页，J.While著N.Y.1944。
其中：R和RⅠ具有前述定义。
通式Ⅱ的二元醇可按已知方法很容易地转化成相应的式Ⅲ衍生物（参见Houben    Weil，Methoden    der    organischem，Chemie，Band    V/3，V/4，Ⅸ    Verlag著，Stuttgard）。
下列的实例说明了本发明的下列醚类及其制备方法：
2-甲基-2-异丙基-1，3-二甲氧基丙烷
2，2-二异丁基-1，3-二甲氧基丙烷
2，2-二苯基-1，3-二甲氧基丙烷
2，2-二苯甲基-1，3-二甲氧基丙烷
2，2-双（环己甲基）-1，3-二甲氧基丙烷
2，2-二异丁基-1，3-二丁氧基丙烷
2，2-二异丁基-1，3-二乙氧基丙烷
2-异戊基-2-异丙基-1，3-二甲氧基丙烷
2，2，4-三甲基-1，3-二甲氧基戊烷
1，1′-双甲氧基甲基环己烷
（+/-）2，2′-双（甲氧甲基）降冰片烷（外消旋混合物）。
其它一些醚的例子是：
2-异丙基-2-3，7-二甲辛基-1，3-二甲氧基丙烷
2，2-二异丙基-1，3-二甲氧基丙烷
2-异丙基-2-环己甲基-1，3-二甲氧基丙烷
2，2-二异戊基-1，3-二甲氧基丙烷
2-异丙基-2-环己基-1，3-二甲氧基丙烷
2-异丙基-2-环戊基-1，3-二甲氧基丙烷
2，2-二环戊基-1，3-二甲氧基丙烷
2-庚基-2-戊基-1，3-二甲氧基丙烷
2，2-二环己基-1，3-二甲氧基丙烷
2-异丙基-2-异丁基-1，3-二甲氧基丙烷
2，2-二丙基-1，3-二甲氧基丙烷
实例1
2，2-二异丁基-1，3-二甲氧基丙烷的制备
a）二异丁基丙二酸乙酯的制备
在氮气流下将100克无水乙醇和5克（0.22摩尔）钠加入到装有搅拌器、冷却液、进料漏斗、温度计和导气管的250毫升烧瓶中。在钠完全溶解后，输入16克（0.1摩尔）丙二酸二乙酯，在室温下搅拌几分钟。然后加入28克异丁基溴（0.21摩尔），混合物在搅拌下回流6小时。其后，加入7.5克无水乙醇钠（0.12摩尔）和14克异丁基溴（0.1摩尔），继续搅拌加热回流8小时。
在减压下（50mmHg）蒸发出大部分溶剂，残留物用200毫升己烷提取。从蒸馏的己烷溶液得到15.5克二异丁基丙二酸乙酯，沸点为145-146℃/20毫米汞柱。产物的气相色谱法纯度（主峰面积）为97.5%，与按照Bently和Perkin，J.Chem.Soc.73，61所制备的二异丁基丙二酸乙酯试样相符。
b）2，2-二异丁基-1，3-丙二醇的制备
在氮气流下向上述（a）所述相同烧瓶中输入100毫升二***和3克LiAlH4（0.079摩尔）。然后，在剧烈搅拌下用1小时时间逐滴加入上述（a）制得的15.5克二异丁基丙二酸乙酯，并将混合物回流30分钟。
其后，将反应混合物倒入含有用稀盐酸酸化的100克冰的容器中并用100毫升***提取三次。蒸发掉***，制得10克粗产品，用己烷结晶，得到8.5克2，2-二异丁基-1，3-丙二醇，熔点为75-77℃，元素分析：C为70.3%，H为12.6%。C11H24O2的理论计算值：C为70.21%， H为12.7%。
c）2，2-二异丁基-1，3-二甲氧基丙烷的制备
在氮气下，向前述a）所述的相同烧瓶中装入8.5克（0.06摩尔）2，2-二异丁基-1，3-丙二醇、200毫升二噁烷和15.4克（0.136摩尔）叔丁醇钾。将该混合物在室温下搅拌30分钟，然后逐滴加入20克CHI（0.14摩尔）。在此过程中，温度自行升至50℃。2小时后，再加入154克（0.136摩尔）叔丁醇钾和20克（0.14摩尔）CH3I，并将混合物回流1小时。将反应物过滤，滤液在减压下蒸馏。在这些产物中，得到7.4克2，2-二异丁基-1，3-二甲氧基丙烷，沸点为100-101℃/22mmHg，气相色谱法（GLC）表明其纯度为99%（色谱峰面积）。折射率为：nD 20＝1.4337。核磁共振数据如下：
1HNMR（300MHz，CDCl3，TMS为内标）：
0.89ppm双峰12H
1.21ppm双峰4H
1.68ppm多峰2H
3.16ppm单峰4H
3.26ppm单峰6H
用上述a）、b）和c）的方法，制得下列化合物
1）2-甲基-2-异丙基-1，3-二甲氧基丙烷
nD 20＝1.4209，沸点：160℃-161℃/760mmHg
2）2，2-二苯甲基-1，3-二甲氧基丙烷
p.f.105℃（用石油醚）
3）2，2-二异丁基-1，3-二丁氧基丙烷
nD 20＝1.4378，沸点115℃-117℃/1mmHg
4）2，2-二异丁基-1，3-二乙氧基丙烷
nD 20＝1.4302，沸点118℃-120℃/20mmHg
实例2
2，2-双（环己甲基）-1，3-二甲氧基丙烷的制备
向带有锚式搅拌装置的不锈钢高压釜中加入5.8克（0.02摩尔）实例1制备的（C6H5CH2）2C（CH2OCH3）2、100毫升正己烷和10克阮内镍，该阮内镍先用3份50毫升无水乙醇，然后用3份50毫升己烷倾析洗涤。
高压釜用17个大气压氢气加压，在搅拌下加热至135℃（内温）8小时。冷却后，反应混合物滤出催化剂，真空蒸发，得到5.9克无色油状物，纯度为99%，nD 20＝1.4790。用薄层色谱法（TLC）测定仅有一种化合物，为2，2-双（环己基、甲基）-1，3-二甲氧基丙烷。
1HNMR（300MHz，CDCl3，TMS为内标）数据：
0.96ppm多峰4H
1.18ppm多峰12H
1.63ppm多峰10H
3.15ppm单峰4H
3.27ppm单峰6H
实例3：
2，2-二苯基-1，3-二甲氧基丙烷的制备
a）2，2-二苯基-1，3-丙二醇的制备
向实例1（a）所述的同样烧瓶中加入10.6克（0.054摩尔）（C6H5）2-CHCHO（Fluka），4.03克（0.028摩尔）K2CO3，10毫升水，13.2毫升40%甲醛水溶液（0.176摩尔）和35毫升纯度为99%的乙醇。将混合物搅拌并回流6小时，冷却，用200毫升水稀释。将这样制成的沉淀物滤出，用水洗涤，用苯结晶，得到9.6克2，2-二苯基-1，3-丙二醇，m.p.102-104℃。
b）2，2-二苯基-1，3-二甲氧基丙烷的制备
向前述a）所述同样的烧瓶中装入9.6克2，2-二苯基-1，3-丙二醇溶 解在400毫升无水四氢呋喃的溶液，并在氮气下与3.8克NaH（55%NaH，分散在凡士林油中）一起搅拌，直到不产生氢气为止。用20分钟时间加入9.6毫升CH3I，并连续搅拌2小时。蒸发出大部分的四氢呋喃，然后产物用水（200毫升）稀释，用每次50毫升***提取2次。用真空蒸馏法由醚提取物得到3.5克2，2-二苯基-1，3-二甲氧基丙烷，沸点188℃-190℃/20mmHg，经TLC色谱法鉴定为单一化合物，nD 20＝1.5558。
按照前述a）和b）所述相同的方法，制备了下列化合物，起始物分别是六氢苯甲醛和降冰片-2-羧甲醛。
A）1，1-双甲氧基甲基环己烷
沸点：97-98℃/20mmHg;nD 20＝1.4487
1HNMR（300MHz，CDCl3，TMS为内标）：
1.36ppm多峰10H
3.20ppm多峰4H
3.29ppm多峰6H
B）（+/-）2，2-双甲氧甲基降冰片烷
沸点：106-108℃/20mmHg;nD 20＝1.4659
1HNMR（300MHz，CDCl3，TMS为内标）
0.72ppm双峰1H
1.14ppm双峰1H
1.06ppm多峰1H
1.34ppm多峰2H
1.51ppm多峰3H
1.97ppm单峰（宽）1H
2.15ppm单峰（宽）1H
3.06ppmAB系1H
3.14ppmAB系1H
3.33ppmAB系1H
3.36ppmAB系1H
3.29ppm多峰6H
实例4
2，2，4-三甲基-1，3-二甲氧基戊烷的制备
在氮气流下向一个2升的烧瓶中装入29.2克（0.2摩尔）2，2，4-三甲基-1，3-丙二醇、600毫升二噁烷和10克（0.2摩尔）NaH（在凡士林油中，浓度为50%），该烧瓶装有一个搅拌器、冷却液、加料漏斗、温度计和导气管。搅拌内含物，直到停止产生气体为止;然后加热至80℃，逐滴加入18毫升CH3I（0.28摩尔）。2小时后，加入10克NaH（0.2摩尔）（50%的凡士林油）和40毫升CH3I（0.62摩尔）。加热回流8小时后，反应混合物用1.5升水稀释，用3份己烷（每份100毫升）提取。提取物用水洗涤，干燥后，进行真空蒸馏，得到22.5克2，2，4-三甲基-1，3-二甲氧基丙烷，沸点为105℃/70mmHg，GLC法纯度为98.6%（峰面积），nD 20＝1.4227。
1HNMR（60MHz，CDCl3，TMS为内标）
1.5ppm多峰12H
3.7ppm多峰3H
4.1ppm多峰6H
实例5
2-异戊基-2-异丙基-1，3-二甲氧基丙烷的制备
a）异亚戊基异戊醛的制备
按照DRP643341（1933，I.G.Farb.）和DRP544192（1933，I.G.Farb.））所述的方法，使50克异戊醛反应，得到27克2-异亚戊基异戊醛，沸点98-102℃/20mmHg。
b）2-异戊基异戊醛的制备
按照J.V.Braun和G.Manz，Ber.1969，67（1934）所述氢化的方法，用27克2-异亚戊基异戊醛为起始物，得到27克粗产物，没有标定。测得的氢吸收峰与所报导的反应相一致。
c）2-异丙基-2-异戊基-1，3-丙二醇的制备
向实例1a）同样的烧瓶中装入27克前述b）制备的粗醛产物、16克K2CO3、200毫升纯度为99%的乙醇和52毫升CH2O的40%水溶液，搅拌回流4小时。然后，反应混合物用1升水稀释，用***提取2次，每次250毫升。蒸发掉醚，并将醚提取物干燥，然后在减压下蒸馏，得到（在其它化合物中）9克2-异丙基-2-异戊基-1，3-丙二醇，沸点为165℃/20mmHg，TLC测定是单一的。该物料不必进一步分析就可用于下面反应。
d）2-异丙基-2-异戊基-1，3-二甲氧基丙烷的制备
在氮气流下向实例1a）的同样烧瓶中装入9克上述c）制得的粗产物、200毫升二噁烷和15克叔丁醇钾，搅拌约30分钟。然后用1小时时间加入10毫升CH3I，将混合物回流5小时，反应混合物用1升水稀释，用***提取。蒸发掉醚，醚提取物干燥后减压蒸馏。在其它化合物中，得到7.3克2-异丙基-2-异戊基-1，3-二甲氧基丙烷，沸点为130-133℃/35mmHg，气相色谱纯度为98.6%（峰面积）。nD 20＝1.4365。
1HNMR（300MHz、CDCl3、TMS为内标）
0.87ppm双峰6H
8.89ppm双峰6H
1.11ppm多峰2H
1.28ppm多峰2H
1.42ppm多峰1H
1.76ppm多峰1H
3.23ppm单峰2H
3.24ppm单峰2H
实例6
在搅拌下，向500毫升烧瓶中装入60毫升正庚烷和67毫升叔正丁氧基钛，加热至45℃。用3小时时间，逐渐地加入AlEt2Cl（44.8毫升）的正庚烷（108毫升）溶液。使温度升至60℃，维持1小时然后冷却至室温。分离出固体，每次用100毫升庚烷洗涤4次，然后真空干燥。
将8.1克上述固体和20.3毫摩尔四氯化钛、20.3毫升甲苯、20.3毫摩尔2，2-二异丁基-1，3-二甲氧基丙烷一起加入到烧瓶中，加热至60℃维持1小时，然后在100℃温度下加热4小时。反应混合物在室温下冷却，分离出固态产物，用正庚烷洗涤直到滤液中没有氯离子为止，并在氮气流下在烘箱中干燥。
在氮气流下干燥后，向装有磁性搅拌器的120毫升高压釜中加入250毫克AlEt2Cl、12.4毫克上述制备的固体物和80毫升液态丙烯，加热至60℃，并在此温度下搅拌1小时。排出过量的未反应丙烯，得到16.9克聚丙烯，全同立构指数为96.8%（用正庚烷沸腾4小时提取）。

Claims (3)

1、一种制备式(Ⅰ)的二醚的方法，
Figure 891076751_IMG2
其中：R、RⅠ、RⅡ、RⅢ、RⅡ和RⅠ可相同或不同，代表H或有1-18个碳原子的直链或支化烷基、环烷基、芳基、烷芳基或芳烷基，条件是R和R不能都是H或CH3，或不是CH3和正丙基；RⅡ和RⅢ可相同或不同，代表有1-6个碳原子的烷基；R至RⅡ中的一个或多个基团可键接形成环状结构，
该方法包括使相应的式Ⅱ的二醇进行醚化反应，
Figure 891076751_IMG3
其中R、RⅠ、RⅡ、RⅢ、RⅡ和RⅠ定义同上。
2、根据权利要求1的方法，其中所述二醚中RⅡ和RⅢ是有1-6个碳原子的烷基，RⅡ、RⅢ、RⅡ和RⅠ是氢，而当R和RⅠ是烷基时，它们有3个或更多个碳原子。
3、根据权利要求2的方法，其中所述二醚选自2，2-二异丁基-1，3-二甲氧基丙烷、2，2-二苯基-1，3-二甲氧基丙烷、2，2-二苯甲基-1，3-二甲氧基丙烷、2，2-双（环己甲基）-1，3-二甲氧基丙烷、2-异戊基-2-异丙基-1，3-二甲氧基丙烷、
2-异丙基-2-3，7-二甲辛基-1，3-二甲氧基丙烷
2，2-二异丙基-1，3-二甲氧基丙烷
2-异丙基-2-环己甲基-1，3-二甲氧基丙烷
2，2-二异戊基-1，3-二甲氧基丙烷
2-异丙基-2-环己基-1，3-二甲氧基丙烷
2-异丙基-2-环戊基-1，3-二甲氧基丙烷
2，2-二环戊基-1，3-二甲氧基丙烷
2-庚基-2-戊基-1，3-二甲氧基丙烷
2，2-二环己基-1，3-二甲氧基丙烷
2-异丙基-2-异丁基-1，3-二甲氧基丙烷
2，2-二丙基-1，3-二甲氧基丙烷
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NO171676B (no) 1993-01-11
HUT53304A (en) 1990-10-28
FI894628A0 (fi) 1989-09-29
MX17734A (es) 1993-12-01
AU620154B2 (en) 1992-02-13
US5095153A (en) 1992-03-10
CZ554689A3 (en) 1994-04-13
NO893899D0 (no) 1989-09-29
KR0149006B1 (ko) 1998-10-15
FI894628A (fi) 1990-03-31
DE68919460T2 (de) 1995-04-20
DE68919460D1 (de) 1995-01-05
JP2804117B2 (ja) 1998-09-24
IL91684A0 (en) 1990-04-29
NO893899L (no) 1990-04-02
HU206644B (en) 1992-12-28
CZ278978B6 (en) 1994-11-16
NO171676C (no) 1993-04-21
FI93721B (fi) 1995-02-15
RU2027695C1 (ru) 1995-01-27
ZA897439B (en) 1990-07-25
EP0361493B1 (en) 1994-11-23
JPH02256633A (ja) 1990-10-17
PT91864B (pt) 1995-05-31
FI93721C (fi) 1995-05-26
CN1041752A (zh) 1990-05-02
AU4252489A (en) 1990-04-05
UA39914C2 (uk) 2001-07-16
EP0361493A1 (en) 1990-04-04
YU187789A (en) 1991-04-30
ES2064413T3 (es) 1995-02-01
KR900004664A (ko) 1990-04-12
CA1340195C (en) 1998-12-15
IT8822152A0 (it) 1988-09-30
BR8904951A (pt) 1990-05-08
PT91864A (pt) 1990-03-30

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