Commercial Organofunctional Silanes for. Diagnostics and Separation

Transcription

1 01 Commercial rganofunctional lanes for Diagnostics and Separation

2 Ulrike and Dr. orbert Braunagel Managing Directors of abcr

3 Gute Chemie oreword 1 Gute Chemie. Welcome to abcr. What do you think of when you hear the expression gute Chemie? Does it make you think of top-quality products or people that understand each other really well? nce we set up our company in 1987, we have consistently attempted to combine both. We offer gute Chemie in the form of more than 100,000 specialty chemicals that we supply to major pharmaceuticals and chemical companies. And we also provide gute Chemie in terms of our personal service coupled with an extensive network that links our clients, suppliers and partners all around the world. With this brochure, we would like to invite you to experience all the aspects of gute Chemie. Dr. orbert Braunagel Ulrike Braunagel

4 Commercial rganofunctional lane for Diagnostics and Separation Sciences. rganofunctional silanes are widely used commercially for diagnostics and separation science due to their remarkable versatility. They are hybrid molecules that combine the functionality of a reactive organic group and inorganic functionality into a single molecule. This unique property is used as a molecular bridge to make inorganic materials organically compatible. rganofunctional silanes molecules have two reactive centers, one characterized by at least one hydrolytically stable carbonsilicon bond which allows the introduction of non-reactive or reactive organic functionality such as alkyl, aryl, arylalkyl, perfluorophenylalkyl, amino, epoxy, aldehyde, ethylene and anhydride. The other reactive centers of the silicon atom are characterized by hydrolyzable groups, mainly chloro, alkoxy and amine. The hydrolyzable component of organofunctional silanes will hydrolyze readily with water to form silanols and allow silicon to covalently bond to inorganic surfaces through a siloxane bond. In addition to forming covalent siloxane bonds with inorganic substrates, the hydrophobic nature of the silicon-carbon bond provides improved resistance at the interphase between siloxane bond and substrate to hydrolysis attack under extreme ph conditions. This feature makes stationary phases and the silica support matrix used in liquid chromatography more hydrolytically stable and hence increasing service life by protecting the silica s mechanical properties. The organofunctional silanes can be tri-functional, di-functional and mono-functional. Typical molecular structure for a tri-functional silane X (CH 2 ) n R R R R can an example be for chloro, dimethylamine or methoxy X can an example be for hydrogen, perfluorphenyl, phenyl, amino, oxy or cyano In order to initiate the hydrolysis reaction of organofunctional alkoxysilanes to subsequently form covalent siloxane bonds, a catalyst is generally required; typically a mild acid or base will be sufficient. The most common catalysts are acetic acid and ammonia. Chlorosilanes and aminosilanes are autocatalytic because the hydrolyzable groups will generate in situ, hydrochloric acid or amine thus creating a reaction medium with an acid catalyst with ph 0-1 or a base catalyst with ph The tri-functional silanes, e.g. trimethoxysilanes, hydrolyze first to form a silanol group and then condense with surface hydroxyl groups to form a hydrolytically stable covalent bond and also crosslink to form a multilayer (silsequioxane) coating. This multilayer is formed at the inorganic interphase and can also diffuse into the a porous matrix to create an interpenetrating network within the inorganic substrate which in turn generates a more hydrolytically stable silica support for liquid chromatography. The di-functional silanes, e.g. dimethothoxysilanes also hydrolyze first to form a silanol group and then condense with surface hydroxyl groups to form hydrolytically stable covalent bonds. The di-functional silanes can also form polymeric materials that can adhere to different types of surfaces. Therefore organo- functional silanes that are di-functional can be used to make bonded phases for liquid chromatography or make siloxane polymers for capillary columns used in gas chromatography. The mono-functional silanes due to their single hydrolyzable reactive group will form a self-assemble-monolayer (SAM) on the inorganic substrate thus creating a uniform molecular layer on the inorganic substrate s surface. This may offer advantages because the film thickness is easily controlled where it is well known that for tri- and di- functional silanes: reproducibly controlling the film thickness can be quite challenging. Typically, mono-functional silanes are generally used to make bonded phases for analytical applications while due to the higher hydrolytic stability, the di- and tri-functional silanes are more commonly used to make bonded phases for sample prep-scale chromatography, solid phase extraction (SPE) and preparative chromatography

5 Gute Chemie Commercial rganofunctional lanes Reagents 2 3 for the purification of active pharmaceutical ingredients (API). An important aspect of bonded phases for liquid chromatography is capping (endcapping) of unreacted silanol groups left on the inorganic surfaces after the bonding phase step. These unreacted hydroxyl groups adversely affect performance and are therefore capped with a trimethysilyl group. Hydroxyl and free water scavengers like trimethylchlorosilane and hexamethyldisilazane are efficient however a customized solution of trimethylchlrosilane and hexamethyldisilazane has a higher reactivity and is more effective than either of the reagents alone. In addition, capping of silanols groups will lead to free flowing particles which may aid in the reproducibility of column pressures of bonded silica packed chromatography columns. rganofunctional silanes with a hydrolyzable dimethylamino group are versatile silylating reagents for capping silanols. Due to its extreme reactivity with hydroxyl groups, dimethylaminotrimethylsilane is a highly effective silanol scavenger. The by-product formed, dimethylamine, can be easily removed during reflux or by applying vacuum. It must be noted that dimethylamino silanes are extremely hydrolytically sensitive, even more reactive than chlorosilanes. They will almost instantaneously react with moisture in the air; water contained in polar solvents, adsorbed on the surfaces of glass bottles and GC vials. When handling these types of products during analysis, the use of inert gases, silanized GC vials, anhydrous solvents for syringe cleaning and GC column pre-conditioning are highly recommended. In order to facilitate analysis and process handling these products are also offered as a solution in a non-polar solvent. Depending on the analyte, retention time and selectivity, there are numerous organofunctional silanes available for gas and liquid chromatography. A stationary phase is defined by the specific chemical ligands bonded to the silica support which in combination with solvent and ph, control selectivity and retention time of analytes. The mobile phase is defined by the solvent which contains the analytes. The solvent can be gas as in the case of gas chromatography or non-polar solvents for normal phase chromatography (PC) or polar solvents for reverse-phase chromatography (RPC) and hydrophilic interaction chromatography (HILIC). Gas (GC) and Liquid Chromatography (LC) employ specific modes of separation which are influenced by the polarity of the stationary phase. The most common ligands found in commercial stationary phases are: Alkyl Phases C18 C8 C4 C1 Phenyl Phases Phenyl Perfluorphenylpropyl Phenylalkyl Polar embedded Phases Polar Phases Cyano Amino Hydroxyl In addition, in the field of biochromatography, whole new classes of ligands are being investigated for the analysis and purification of natural compounds that are biologically active. Selectivity and retention time are being optimized based on the affinity of these natural compounds to different ligands. The particular nature of the analyte will determine the choice of organofunctional silane as well as the way in which it bonds to the supporting silica matrix. Through a close cooperation with you, abcr labs develops the ideal product solutions to fulfill your particular demands. abcr is your reliable innovation partner for specialty chemicals.

6 Gute Chemie. abcr and abcr labs.

7 Gute Chemie abcr and abcr labs 4 5 In 2010, abcr GmbH & Co. KG, located in Karlsruhe, Germany, established a new contract manufacturing facility for fine chemicals and specialty materials, abcr labs S.L. in orcarei, Spain. The 6,000 m2 manufacturing site provides contract services for custom synthesis, product and process development, scale-up and commercialisation. abcr labs operates 24 hours a day, 5 days a week. The flexible manufacturing platform consists of a kilo lab, pilot plant and full-scale commercial production facilities. In addition, R&D and analytical laboratories provide technical support and testing for raw materials and in-process and finished products to support manufacturing operations. abcr labs bulk products are shipped to abcr s logistics centre in Karlsruhe, Germany, for final packaging and global distribution. abcr GmbH & Co. KG has been delivering specialty chemicals to renowned pharmaceutical, chemical and material science-oriented companies worldwide since Via the 2,500 m 2 logistic centre in Karlsruhe, Germany, abcr organises product shipping to more than 10,000 individual laboratories worldwide. Competent assistance from our chemists and engineers, worldwide sourcing activities, as well as reliable deliveries at fair prices and excellent quality have made abcr the preferred supplier of many customers. abcr keeps stock of most of their 50,000 items up to semibulk quantities, offering you immediate access to organosilanes, silicones, fluorinated chemicals, organic and inorganic compounds, precious metal compounds, metal-organics, homogeneous and heterogeneous catalysts, nanomaterials, phosphines, rare earth compounds and many more. The products are available in regular catalogue units, as well as on a semi-bulk and bulk scale. abcr Karlsruhe abcr labs Spain abcr Locations/ Distributors

8 Custom synthesis. Gute Chemie paves the way for new products and processes. Lasting Relationships abcr builds lasting relationships with customers by collaborating at all stages of product development, from laboratory scale to commercial production, from gram to ton quantities.

9 Gute Chemie Custom synthesis 6 7 Chemical Process Equipment abcr labs chemical process equipment makes use of batch, semi-batch, reactive distillations and continuous process technology. The portfolio of chemical processes consists of: Condensation Ammonolysis Alkyllithium reaction Grignard formation & reaction Alkoxylation Catalytic hydrogenation Amination Esterification Transesterification Halogenation Hydrolysis Hydrosilylation LAH reduction Lithiation reaction Ring opening polymerisation lylation Applications or more than 20 years, abcr has been supplying specialty chemicals in laboratory-scale and semi-bulk quantities to companies worldwide. These products can be widely used as: lylating and protecting groups Adhesion promoters Reducing agents Derivatisation Various reagents for organic synthesis Reagents for bioactive reactions Blocking agents Surface modification Thinfilm deposition ptical and conductive coatings Catalysis Polymer synthesis and many more

10 In-house production. Gute Chemie means trusting in the quality of the products you make. Kilo Lab: The kilo laboratory facilities manufacture products in the range of 5 to 15 kg; they are equipped with 6 walk-in fume hoods, one bench top fume hood for weighing and two distillation bench tops for fractional distillations. Pilot Plant: Pilot plant facilities are composed of six processing suites, two of which are equipped with two reactor pairs with working capacities of 160 and 400 litres. The automated reactors are Pfaudler-Pharmaglass lined; they have azeotropic, flash and fractional distillation capabilities; they operate from full vacuum to 10 bars of pressure and temperature from -20 C to 220 C. A third suite is equipped with a continuous thin film evaporator for purification of heat sensitive materials and low volatility products. The remaining suites are dedicated for special projects and future expansion.

11 Gute Chemie In-house production 8 9 Commercial Plant: The full scale commercial plant facilities are equipped with automated reactors that are Pfaudler-Pharmaglass lined; have azeotropic, flash and fractional distillation capabilities; operate from full vacuum to 10 bars of pressure and temperatures from -20 C to 220 C. Both reactors are supported by a 1,000 litre (1.2 m 3 ) corrosion resistant alloy eutsche ilter/ dryer equipped with automatic cake discharge for rapid turnover and has an operating temperature range from -20 C to 120 C. The plant has the infrastructure in place for an additional 6 reactors ranging from 2,500 to 8,000 litres.

12 Safety. Gute Chemie gives you a feeling of security from procurement to delivery. Safety: As important as the air we breathe As in the parent company abcr, at abcr labs highest standards of safety are also observed. This equally applies to environment, health and safety regulations. When it comes to quality assurance, abcr accepts no compromises. As is the case at abcr, the modern production facility is climatically supplied by an earth tube which cools the building by up to 7 C in the summer and warms it accordingly in the winter. The plants on the roof serve as a natural buffer for temperature peaks. Quality with responsability abcr has strict standards of quality and is committed to complying with all the environmental, health and safety regulations. ients are welcome to audit the quality systems that are critical to our success.

13 Gute Chemie Safety Your professional partner for products and services Custom synthesis for complex multi-step or air-sensitive reactions Specialty chemicals outsourcing of small or medium-sized products Tailor-made solutions according to customer needs Transfer and up-scaling of new processes from laboratory to commercial scale lanes and specialty silicones Metalorganic compounds rganic intermediates rgano-lanes & licones

14 lexible quantities. Gute Chemie is when you can order any different quantity from the same company.

15 Gute Chemie lexible quantities Glass bottles arrow neck bottle (brown) Wide neck bottle (brown) Septum bottle (brown) Lab glass bottle with scale (white) ml ml ml ml Plastic bottles arrow neck bottle (PA) (off-white) arrow neck bottle (PE) (off-white) Wide neck bottle (PE) (off-white) algene narrow neck bottle (HDPE) ml ml ml ml Stainless steel bottles GL45 Stainless steel bottles with PE cap Stainless steel bottles with Stainless steel cap ml ml Cylinders Steel cylinders Stainless steel cylinders ml 50 ml - 3,78 l (1 Gallone) Stainless steel Bubblers Stainless steel Bubblers with standard valve Stainless steel Bubblers with cross-purge valve 1.5 l - 33 l 150 ml l Plastic canisters Plastic canisters 5-20 l Barrels Combination barrels Steel barrels inside cover Stainless steel barrels Plastic barrels with lid and clamping ring l l l l

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17 Gute Chemie Products 15 Diagnostics and Separation. Table of content C18, n-ctadecylsilanes 17 C8, n-ctylsilanes 18 C4, n-butylsilanes 19 C1, Trimethylsilylating Agents for lanol Capping 19 Arylsilanes 20 Arylalkylsilanes 21 luoroarylsilanes 22 Cyano unctional lanes 23 Amino unctional lanes 24 Epoxy unctional Alkylsilanes 25 Acetoxy and Aldehyde unctional Alkylsilanes 25 Carboxylic Acid unctional Alkylsilanes 25 unctional Alkylsilanes 26 Polar Embedded lanes 27

18 16 C18, n-ctadecylsilanes AB n-ctadecyldiisobutylchlorosilane; 95% AB n-ctadecyldiisobutyl(dimethylamino)silane; 95% (5-10% C18 isomers) AB n-ctadecyldiisobutyl(dimethylamino)silane; 25% in toluene AB n-ctadecyldimethylchlorosilane; 95% (5-10% C18 isomers) AB n-ctadecyldimethylchlorosilane; 70% in toluene AB n-ctadecyldimethyl(dimethylamino)silane; 95% (5-10% C18 isomers) AB n-ctadecyldimethyl(dimethylamino)silane; 25% in toluene AB n-ctadecyldimethylmethoxysilane; 97% AB n-ctadecylmethyldichlorosilane; 97% AB n-ctadecylmethyldichlorosilane, 70% in toluene AB n-ctadecylmethyldimethoxysilane; contains 5-10% C18 isomers Gute Chemie

19 Gute Chemie Diagnostics and Separation 17 AB n-ctadecyltrichlorosilane; 95%, cont. 5-10% branched isomers AB n-ctadecyltrichlorosilane; 70 wt% in toluene AB n-ctadecyltrimethoxysilane; 97% C8, n-ctylsilanes AB n-ctyldiisopropylchlorosilane; 95% AB n-ctyldimethyl(dimethylamino)silane; 95% AB n-ctyldimethyl(dimethylamino)silane; 25% in toluene AB n-ctyldimethylchlorosilane; 97% AB n-ctyldimethylmethoxysilane; 97% AB n-ctylmethyldichlorosilane; 97% AB n-ctylmethyldimethoxysilane; 95% AB n-ctyltrichlorosilane; 97% abcr GmbH & Co. KG Phone ax

20 18 AB n-ctyltrimethoxysilane; 97% C4, n-butylsilanes AB n-butyldimethylchlorosilane; 97% AB n-butyldimethyl(dimethylamino)silane; 95% AB n-butyldimethyl(dimethylamino)silane; 25% in toluene AB n-butyldimethylmethoxysilane AB n-butylmethyldichlorosilane; 97% AB n-butylmethyldimethoxysilane; 97% AB n-butyltrichlorosilane; 97% AB n-butyltrimethoxysilane; 97% C1, Trimethylsilylating Agents for lanol Capping AB (,-Dimethylamino)trimethylsilane; 97% AB (,-Dimethylamino)trimethylsilane; 25% in toluene Gute Chemie

21 Gute Chemie Diagnostics and Separation 19 AB (Trimethylsilyl)imidazole; 97% AB Trimethylchlorosilane; 99% AB Trimethylmethoxysilane; 97% AB Hexamethyldisilazane; 99.5% H AB TMS lylating Solution: Hexamethyldisilazane/Chlorotrimethylsilane; 2:1 volume ratio Arylsilanes AB Phenyldimethylchlorosilane; 97% AB Phenyltrichlorosilane; 97% AB Phenyltrimethoxysilane; 97% AB ,4-Bis(dimethylsilyl)benzene; 97% ,00 H H AB ,4-Bis(hydroxydimethylsilyl)benzene; 95% H H AB Biphenyldimethylchlorosilane; 95% abcr GmbH & Co. KG Phone ax info@abcr.de

22 20 Arylalkylsilanes AB Phenylhexyldimethylchlorosilane; 97% AB Phenylhexyldimethyl(dimethylamino)silane; 95% AB Phenylhexyldimethyl(dimethylamino)silane; 25% in toluene AB Phenylhexyldimethylmethoxysilane; 97% AB Phenylhexylmethyldichlorosilane; 97% AB Phenylhexylmethyldimethoxysilane; 97% AB Phenylhexyltrichlorosilane; 97% AB Phenylhexyltrimethoxysilane; 97% AB Phenylpropyldimethyl(dimethylamino)silane; 95% AB Phenylpropyldimethyl(dimethylamino)silane; 25% in toluene AB Phenylpropyldimethylchlorosilane; 97% AB Phenylpropyldimethylmethoxysilane; 97% Gute Chemie

23 Gute Chemie Diagnostics and Separation 21 AB Phenylpropylmethyldichlorosilane; 97% AB Phenylpropylmethyldimethoxysilane; 97% AB Phenylpropyltrichlorosilane; 97% AB Phenylpropyltrimethoxysilane; 97% luoroarylsilanes AB Pentafluorophenyldimethylchlorosilane; 95% AB Pentafluorophenyldimethylsilyldiethylamine; 98% AB Pentafluorophenylpropyldimethylchlorosilane; 97% AB Pentafluorophenylpropylmethyldichlorosilane; 97% AB Pentafluorophenylpropylmethyldimethoxysilane; 97% AB Pentafluorophenylpropyltrichlorosilane; 95% AB Pentafluorophenylpropyltrimethoxysilane; 97% abcr GmbH & Co. KG Phone ax

24 22 AB Pentafluorophenyltriethoxysilane; 97% Cyano unctional lanes AB Cyanopropyldimethyl(dimethylamino)silane AB Cyanopropyldimethyl(dimethylamino)silane; 25% in toluene AB Cyanopropyldimethylchlorosilane; 97% AB Cyanopropyldimethylmethoxysilane; 97% AB Cyanopropylmethyldichlorosilane; 97% AB Cyanopropylmethyldimethoxysilane; 97% AB Cyanopropylphenyldichlorosilane; 97% AB Cyanopropylphenyldimethoxysilane; 95% AB Cyanopropyltrichlorosilane; 97% AB Cyanopropyltrimethoxysilane; 97% Gute Chemie

25 Gute Chemie Diagnostics and Separation 23 AB Cyanoundecyltrichlorosilane; 95% AB Cyanoundecyltrimethoxysilane; 97% Amino unctional lanes AB p-aminophenyltrimethoxysilane; 95% H2 AB Aminopropyldimethylethoxysilane; 97% H2 AB Aminopropylmethyldimethoxysilane; 95% H 2 AB Aminopropyltrimethoxysilane; 97% H2 AB Aminoundecyltriethoxysilane; 95% H2 AB (3-,-Dimethylaminopropyl)methyldimethoxysilane; 97% AB ,-Dimethylaminopropyl(triethoxy)silane; 97% AB (3-,-Dimethylaminopropyl)trimethoxysilane; 97% AB Phenylaminopropyltrimethoxysilane; 95% H abcr GmbH & Co. KG Phone ax info@abcr.de

26 24 Epoxy unctional Alkylsilanes AB ,6-Epoxyhexyltriethoxysilane; 97% AB (3-Glycidoxypropyl)dimethylethoxysilane; 97% AB (3-Glycidoxypropyl)trimethoxysilane; 98% Acetoxy and Aldehyde unctional Alkylsilanes AB Acetoxyethyldimethylchlorosilane; 97% AB Acetoxyethyltrichlorosilane; 97% AB Acetoxyphenethyltrichlorosilane; 97% AB (Triethoxysilyl)propylsuccinic anhydride; 95% AB (Triethoxysilyl)undecanal; 90% Carboxylic Acid unctional Alkylsilanes AB Triethoxysilylbutanoic acid; 95% H AB Triethoxysilylpentanoic acid; 95% H Gute Chemie

27 Gute Chemie Diagnostics and Separation 25 AB Triethoxysilylhexanoic acid; 95% H AB Triethoxysilylheptanoic acid; 95% H AB Triethoxysilyloctanoic acid; 95% H AB Triethoxysilylnonanoic acid; 95% H AB Triethoxysilyldecanoic acid; 95% H AB Triethoxysilylundecanoic acid; 95% H unctional Alkylsilanes AB ctenyldimethylchlorosilane; 95% AB ctenyldimethylmethoxysilane; 95% AB ctenyltrimethoxysilane; 95% AB Undecenyltrichlorosilane; 95% AB Undecenyltrimethoxysilane; 95% abcr GmbH & Co. KG Phone ax info@abcr.de

28 26 AB Bromoundecyltrichlorosilane; 95% Br AB Bromoundecyltrimethoxysilane; 95% Br Polar Embedded lanes AB [3-(Dimethoxymethylsilyl)propyl]-hexadecanamide; 95% H AB [3-(Methoxydimethylsilyl)propyl]-hexadecanamide; 95% H AB [3-(Trimethoxysilyl)propyl]-hexadecanamide; 95% H Gute Chemie

29 Gute Chemie Diagnostics and Separation 27 CAS Page CAS Page CAS Page , abcr GmbH & Co. KG Phone ax

30 abcr GmbH & Co. KG Im Schlehert Karlsruhe Germany Phone ax zertifiziertes Qualitätsmanagementsystem