CN1257074A - 制备有机硅二硫烷的方法 - Google Patents
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- dithioane
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- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 title claims description 13
- 229910052710 silicon Inorganic materials 0.000 title claims description 11
- 239000010703 silicon Substances 0.000 title claims description 11
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 claims description 9
- 150000002148 esters Chemical class 0.000 claims description 8
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical class SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 abstract description 8
- 238000002360 preparation method Methods 0.000 abstract description 4
- 239000003513 alkali Substances 0.000 abstract 1
- 238000011065 in-situ storage Methods 0.000 abstract 1
- 238000002955 isolation Methods 0.000 abstract 1
- 150000003567 thiocyanates Chemical class 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- 229910052799 carbon Inorganic materials 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000011734 sodium Substances 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 5
- KSCAZPYHLGGNPZ-UHFFFAOYSA-N 3-chloropropyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)CCCCl KSCAZPYHLGGNPZ-UHFFFAOYSA-N 0.000 description 4
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- -1 chlorine alkyl silane Chemical class 0.000 description 4
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- MCEBKLYUUDGVMD-UHFFFAOYSA-N [SiH3]S(=O)=O Chemical compound [SiH3]S(=O)=O MCEBKLYUUDGVMD-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 230000007812 deficiency Effects 0.000 description 3
- 229920001971 elastomer Polymers 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000000000 cycloalkoxy group Chemical group 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- VGTPCRGMBIAPIM-UHFFFAOYSA-M sodium thiocyanate Chemical compound [Na+].[S-]C#N VGTPCRGMBIAPIM-UHFFFAOYSA-M 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- 238000007738 vacuum evaporation Methods 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 229960004217 benzyl alcohol Drugs 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910000064 phosphane Inorganic materials 0.000 description 1
- 150000003002 phosphanes Chemical class 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000003377 silicon compounds Chemical class 0.000 description 1
- 229960001866 silicon dioxide Drugs 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 238000005406 washing Methods 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
-
- 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
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
- C07F7/1872—Preparation; Treatments not provided for in C07F7/20
- C07F7/1892—Preparation; Treatments not provided for in C07F7/20 by reactions not provided for in C07F7/1876 - C07F7/1888
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
Abstract
用碱金属醇化物使有机硅硫氰酸酯分解制备有机硅二硫烷。
Description
本发明涉及制备有机硅二硫烷的方法。
有机硅二硫烷可用于制造含有二氧化硅填料的橡胶制品。在这方面,人们特别感兴趣的是使用高纯度的有机硅二硫烷(EP-A0 732 362;L.Panzer,American Chem.Soc.,Rubber Div.Meeting1997)。
高纯度的有机硅二硫烷的制备对于专家来说也是困难的,因为已知的方法,例如3-氯丙基三乙氧基硅烷与Na2S2的反应,得到的产品混合物中含有单硫烷或长链寡硫烷组分。但是这些组分是不希望存在的,因为单硫烷在应用中是不活拨的,而长链寡硫烷会对混和过程产生不希望的影响。
已知可以通过多硫烷与氰化物,磷酸盐(phosphanes)或亚硫酸盐一起进行二硫化反应来制备高纯度的有机硅二硫烷(EP-A 0 773224)。
上述方法的不足在于,首先必须制备多硫烷,然后再使多硫烷降解为二硫烷。另一个不足是使用有毒的物质,例如氰化物和磷化物。
已知还可以通过用MnO2或SO2Cl2氧化相应的巯基硅烷来制备有机硅二硫烷(EP-A 0 718 392; DE-A 23 60 470)。
上述已知方法的不足在于使用巯基硅烷作为离析物,而巯基硅烷需要采用工业方法,由相应的氯烷基硅烷和硫脲反应,然后裂解thiruronium盐来制备。
本发明提供了一种制备有机硅二硫烷的方法,其特征在于,在碱金属醇化物存在下使有机硅硫氰酸酯分解,该有机硅硫氰酸酯就地生成,或者经过分离。
在本发明的一个实施方案中,有机硅二硫烷相应的通式为:
Z-Alk-S2-Alk-Z (I),其中Z代表如下基团:其中R1表示含有1-5个碳原子的直链或支化烷基,含有5-8个碳原子的环烷基,苄基,或可选择地带有甲基,乙基或氯取代基的苯基,R2表示含有包括1-5个碳原子的直链或支化碳链的烷氧基,或者表示含有5-8个碳原子的环烷氧基,苯氧基,或苄氧基,其中R1和R2在各例中可以相同或不同,Alk表示含有1-10个碳原子的二价饱和直链或支化烃基,或者基团其中n为1-6。
可以使用的硫氰酸酯是化学式如下的化合物:
Z-Alk-SCN (II),其中Z和Alk具有上述的含义。
碱金属醇化物可以使用化学式如下的化合物:
R3O-Me (III),其中R3O表示含有1-5个碳原子的直链或支化碳链的烷氧基,或者表示含有5-8个碳原子的环烷氧基,苯氧基,或苄氧基,Me是钠或钾。
醇化物的烷氧基R3O优选相当于有机硅硫氰酸酯的烷氧基R1。
在本发明的一个优选实施方案中,本发明所使用的硫氰酸酯,可以不必使用分离的或纯化的最终产品,而是可以使用单釜反应的未经分离的粗产品,该产品的合成在本质上是已知的,来自于化学式如下的卤代有机硅化合物:
Z-Alk-Hal (IV),其中Z和Alk具有上述含义,Hal表示氯,溴,或碘原子,和碱金属硫氰酸盐
Me-SCN (V),其中Me表示Na,K或铵。
有机硅硫氰酸酯与碱金属醇化物的反应可以在有机溶剂中进行。
可以使用的有机溶剂,原则上是所有不与化学式II的有机硅化合物反应的极性物质。
含有1-5个碳原子的直链或支链醇,例如甲醇,乙醇,丙醇,丁醇或戊醇,可优选用作有机溶剂。含有5-8个碳原子的环烷醇,苯酚或苄醇也是合适的。
反应可以在环境压力条件下进行,也可以在升高的或降低的压力下进行。反应温度要求在环境温度和特定溶剂的沸点温度之间,该温度是根据所使用的压力条件确定的。反应温度优选接近所使用溶剂的沸点,以便使反应时间较短。
采用本发明方法,得到一种高纯度的二硫烷,其纯度显著超过EP-A 0 732 362中用于用二氧化硅增强的橡胶所要求的值,即至少80%,并且不必经过进一步的纯化步骤,该二硫烷在二硫化物含量方面还显著优于按照现有技术制备的产品。
实施例1由3-氰硫基丙基三乙氧基硅烷制备双(3,3’-三乙氧基硅丙基)二硫烷
在一套包括一个500ml三口瓶,滴液漏斗和回流冷凝器的玻璃装置内,在氮气氛下,将2.3g(0.10mol)金属钠溶解在100ml乙醇中。在所有的钠都已反应形成乙醇钠后,将该混合物加热到沸腾温度,并且当开始回流时,用30分钟,将52.7g(0.20mol)3-氰硫基丙基三乙氧基硅烷滴加进去。滴加完毕后,使该混合物再回流反应3小时。冷却到室温后,使该含有无色沉淀的微黄色溶液在80℃下真空蒸发(最终的真空度为40mbar)。过滤掉无色沉淀物,得到39.6g(0.08mol)双(3,3’-三乙氧基硅丙基)二硫烷。产物经1H-NMR谱确正。实施例2由3-氯丙基三乙氧基硅烷,硫氰酸钠和甲醇钠制备双(3,3’-三乙氧基硅丙基)二硫烷
在一台高压釜内,将48.16g(0.20mol)3-氯丙基三乙氧基硅烷,和18.65g(0.23mol)硫氰酸钠,在100ml乙醇中于120℃加热10小时。冷却后,将得到的粗品滴加到装在实施例1的装置中的沸腾的乙醇钠溶液中,该乙醇钠溶液是由2.3g(0.10mol)金属钠和50ml乙醇制备的。滴加完毕后,该混合物再加热回流3小时,冷却,然后过滤。滤饼用乙醇洗涤两次,每次用30ml乙醇,合并滤液,然后在80℃下真空蒸发(最终的真空度为40mbar)。蒸发残余物再次过滤后,得到37.8g(0.08mol)双(3,3’-三乙氧基硅丙基)二硫烷(基于3-氯丙基三乙氧基硅烷的产率为80%)。产物及其纯度经1H-NMR谱证实。
Claims (1)
1.制备有机硅二硫烷的方法,其特征在于,在碱金属醇化物存在下使有机硅硫氰酸酯分解,该有机硅硫氰酸酯就地生成,或者经过分离。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19848482.8 | 1998-10-21 | ||
DE19848482A DE19848482C1 (de) | 1998-10-21 | 1998-10-21 | Verfahren zur Herstellung von Organosiliciumdisulfanen |
Publications (1)
Publication Number | Publication Date |
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CN1257074A true CN1257074A (zh) | 2000-06-21 |
Family
ID=7885153
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN99121858A Pending CN1257074A (zh) | 1998-10-21 | 1999-10-20 | 制备有机硅二硫烷的方法 |
Country Status (6)
Country | Link |
---|---|
US (1) | US6147241A (zh) |
EP (1) | EP0995754A3 (zh) |
JP (1) | JP2000128889A (zh) |
KR (1) | KR20000029199A (zh) |
CN (1) | CN1257074A (zh) |
DE (1) | DE19848482C1 (zh) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6518335B2 (en) * | 2000-01-05 | 2003-02-11 | Crompton Corporation | Sulfur-containing silane coupling agents |
US6433206B1 (en) | 2001-11-05 | 2002-08-13 | Crompton Corporation | Process for preparing silylorganomercaptans |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2360470A1 (de) * | 1973-12-05 | 1975-06-12 | Dynamit Nobel Ag | Bis-eckige klammer auf gamma -(trialkoxisilyl)-propyl eckige klammer zu disulfide hoher reinheit |
DE2823820A1 (de) * | 1978-05-31 | 1979-12-06 | Siemens Ag | Verfahren zur vernetzung und stabilisierung von radikalisch vernetzbaren polymeren |
US5440064A (en) * | 1994-12-23 | 1995-08-08 | The Goodyear Tire & Rubber Company | Process for the preparation of organosilicon disulfide compounds |
DE19541404A1 (de) * | 1995-11-07 | 1997-05-15 | Degussa | Verfahren zur selektiven Synthese von Silylalkyldisulfiden |
DE19732725A1 (de) * | 1997-07-30 | 1999-02-04 | Degussa | Mischungen, bestehend aus Bis(silylorganyl)polysulfanen und Silylorganylthiocyanaten, ihre Herstellung und Verwendung |
-
1998
- 1998-10-21 DE DE19848482A patent/DE19848482C1/de not_active Expired - Fee Related
-
1999
- 1999-10-14 US US09/417,897 patent/US6147241A/en not_active Expired - Fee Related
- 1999-10-19 EP EP99120687A patent/EP0995754A3/de not_active Withdrawn
- 1999-10-19 JP JP11297169A patent/JP2000128889A/ja active Pending
- 1999-10-20 CN CN99121858A patent/CN1257074A/zh active Pending
- 1999-10-20 KR KR1019990045533A patent/KR20000029199A/ko not_active Application Discontinuation
Also Published As
Publication number | Publication date |
---|---|
EP0995754A3 (de) | 2001-05-23 |
KR20000029199A (ko) | 2000-05-25 |
JP2000128889A (ja) | 2000-05-09 |
US6147241A (en) | 2000-11-14 |
EP0995754A2 (de) | 2000-04-26 |
DE19848482C1 (de) | 2000-06-08 |
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