WO2001012636A1 - Procede de production d'hexamethyldisilazane - Google Patents

Procede de production d'hexamethyldisilazane Download PDF

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Publication number
WO2001012636A1
WO2001012636A1 PCT/EP2000/007437 EP0007437W WO0112636A1 WO 2001012636 A1 WO2001012636 A1 WO 2001012636A1 EP 0007437 W EP0007437 W EP 0007437W WO 0112636 A1 WO0112636 A1 WO 0112636A1
Authority
WO
WIPO (PCT)
Prior art keywords
ammonia
pressure
chlorotrimethylsilane
hexamethyldisilazane
temperature
Prior art date
Application number
PCT/EP2000/007437
Other languages
German (de)
English (en)
Inventor
Helmut Kraus
Lutz Heuer
Original Assignee
Bayer Aktiengesellschaft
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Bayer Aktiengesellschaft filed Critical Bayer Aktiengesellschaft
Priority to AU62790/00A priority Critical patent/AU6279000A/en
Publication of WO2001012636A1 publication Critical patent/WO2001012636A1/fr

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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
    • C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage

Definitions

  • the present invention relates to an improved process for the preparation of hexamethyldisilazane of the formula (CH 3 ) 3 Si-NH-Si (CH 3 ) 3 from chlorotrimethylsilane and ammonia.
  • Hexamethyldisilazane is a chemical that can be used industrially in many different ways. It is used, for example, as a silylation reagent in the manufacture of penicillins, cephalosporins and vitamins, for the hydrophobization of surfaces and polymers which have OH groups and as an aid in phosgenation.
  • n-Hexane Common organic solvents, e.g. n-Hexane must be used in amounts of at least 4 parts by weight, better at least 6 parts by weight (based on 1 part by weight of chlorotrimethylsilane), because otherwise reaction mixtures which are difficult or impossible to stir are obtained. If hexamethyldisilazane which has already been prepared is used as the solvent, it can be used in small amounts. That as
  • By-product resulting ammonium chloride then contains part of the hexamethyldisilazane and cannot be separated from it by normal distillation. You either have to use a thin-film evaporator or convert the hexamethyldisilazane contained in the ammonium chloride to hexamethyldisiloxane with dilute hydrochloric acid. It is also possible that the reaction mixture despite the Use of excess ammonia still contains unreacted chlorotrimethylsilane (see DE-OS 26 45 792).
  • DE-OS 26 45 703 describes the preparation of hexamethyldisilazane from chlorotrimethylsilane and ammonia in hexamethyldisilazane as solvent (at least 1 part by weight of solvent per part by weight of chlorotrimethylsilane), with large amounts of water being added to work up the reaction mixture and the ammonium chloride as aqueous Solution is separated.
  • Reaction vessels with special stirrers carried out a so-called high-shear agitation, so that the ammonium chloride is obtained in a more manageable form.
  • extremely difficult to handle sodium amide is added to the hexamethyldisilazane prepared before the distillation in order to remove the ammonium chloride contained therein.
  • Dewar vessels are used to handle liquefied gases at low temperatures and cork stoppers can only be used at normal pressure or reduced pressure, it is obvious that work was carried out at temperatures below -33 ° C and under normal pressure. There is therefore still a need for a process for the preparation of hexamethyldisilazane which does not require solvents or special apparatus, which gives the desired product in high yields and which can be used with shorter metering and reaction times.
  • a process has now been found for the preparation of hexamethyldisilazane from chlorotrimethylsilane and ammonia, which is characterized in that ammonia and chlorotrimethylsilane are brought together in a pressure-resistant vessel at 60 to 150 ° C. and the reaction mixture is cooled to -10 to + 45 ° C. - is working.
  • ammonia e.g. Use in 1.5 to 6 times, preferably in 2 to 4 times the amount that is theoretically required.
  • Ammonia and chlorotrimethylsilane are preferably brought together at 70 to 120 ° C. You can e.g. proceed in such a way that the ammonia is placed in the pressure-resistant reaction vessel, heated to the desired temperature and then the chlorotrimethylsilane is pumped in, for example, over the course of 5-60 minutes. Ammonia and chlorotrimethylsilane can also be pumped simultaneously into the pressure-resistant reaction vessel at the desired temperature. Continuous operation is also possible, in which the starting materials are introduced simultaneously or alternately in succession into a pressure-resistant reaction tube kept at the desired temperature.
  • the pressure can be, for example, 30 to 100 bar. It is preferably in the range from 35 to 80 bar. If necessary, the chlorotrimethylsilane inlet tube can be flushed or cleared with nitrogen immediately before the start of the inlet, for example by pressing 1 to 5 bar of nitrogen through the inlet tube into the pressure-resistant reaction vessel.
  • the temperature can e.g. deviate from the reaction temperature by up to + 20 ° C or fall during stirring, e.g. up to room temperature or up to 10 ° C above room temperature.
  • reaction mixture present is then cooled to -10 to + 45 ° C., preferably -5 to + 15 ° C.
  • the workup can then be carried out in various ways.
  • the pressure can now be released and the ammonium chloride formed can be separated from the present suspension by filtration and, if appropriate, the filtrate distilled.
  • the cooled reaction mixture which is still under pressure, e.g. 1 to 2 equivalents, preferably 1.1 to 1.5 equivalents of aqueous alkali lye, the temperature being kept in the range from -10 to + 50 ° C, preferably -5 to + 20 ° C, e.g. by pre-cooling the alkali and / or cooling the reaction mixture. Then you can relax and separate the aqueous phase from the product phase.
  • the product phase can e.g. by
  • ammonium chloride present in the aqueous phase can optionally be worked up separately to form ammonia and a saline solution.
  • the aqueous alkali can also be added only after partial or complete pressure release. Other processing methods are also possible.
  • the inventive method allows the production of hexamethyldisilazane in a simple manner, without the use of solvents, without the use of
  • the product phase contained 97.6% hexamethyldisilazane.
  • the TOC value of the water phase was 340 mg / 1.
  • Example 2 was repeated, but only 153 g of ammonia were used. A product phase was obtained which contained 95.5% hexamethyldisilazane.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)

Abstract

L'invention concerne un procédé de production d'hexaméthyldisilazane, de manière avantageuse à partir de chlorotriméthylsilane et d'ammoniac. Ce procédé consiste à mélanger l'ammoniac et le chlorotriméthylsilane dans un récipient résistant à la pression, à une température comprise entre 60 et 150 °C, puis à traiter le mélange réactionnel après refroidissement à une température comprise entre -10 °C et +45 °C.
PCT/EP2000/007437 1999-08-13 2000-07-31 Procede de production d'hexamethyldisilazane WO2001012636A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU62790/00A AU6279000A (en) 1999-08-13 2000-07-31 Method of producing hexamethyldisilazane

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19938475.4 1999-08-13
DE1999138475 DE19938475A1 (de) 1999-08-13 1999-08-13 Verfahren zur Herstellung von Hexamethyldisilazan

Publications (1)

Publication Number Publication Date
WO2001012636A1 true WO2001012636A1 (fr) 2001-02-22

Family

ID=7918336

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2000/007437 WO2001012636A1 (fr) 1999-08-13 2000-07-31 Procede de production d'hexamethyldisilazane

Country Status (3)

Country Link
AU (1) AU6279000A (fr)
DE (1) DE19938475A1 (fr)
WO (1) WO2001012636A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106883257A (zh) * 2017-01-19 2017-06-23 浙江硕而博化工有限公司 三甲基氯硅烷生产六甲基二硅氮烷新工艺

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102004051899A1 (de) * 2004-10-26 2006-04-27 Wacker Chemie Ag Verfahren zur Herstellung von Organosilazanen
US11311952B2 (en) 2018-01-31 2022-04-26 Milwaukee Electric Tool Corporation Reciprocating saw

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
R. O. SAUER; R. H. HASEK: "Derivatives of Methylchlorosilanes. IV Amines", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 68, 1946, pages 241 - 244, XP002149017 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106883257A (zh) * 2017-01-19 2017-06-23 浙江硕而博化工有限公司 三甲基氯硅烷生产六甲基二硅氮烷新工艺

Also Published As

Publication number Publication date
DE19938475A1 (de) 2001-02-15
AU6279000A (en) 2001-03-13

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