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Lonza's Chemical Network Diketene and HCN Derivatives, Heterocycles

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Lonza's Chemical Network Diketene and HCN Derivatives, Heterocycles Lonza’s chemical network Diketene and HCN derivatives, heterocycles and basic chemicals catalog Pharma&Biotech Nutrition Agriculture MaterialsScience PersonalCare Diketene and HCN derivatives, heterocycles and basic chemicals catalog Content About Lonza 3 Introduction 4 Diketene / ketene derivatives 6 Esters 6 Arylides 7 Alkylamides 8 Pyrazolones 9 Dehydroacetic acid 9 Lonzamon monomers 10 Other diketene derivatives 10 HCN derivatives 12 Heterocycles 14 Basic chemicals 16 Others 17 Alphabetical index 18 About Lonza Lonza is the global leader in the production and support of active phar- From 1897 to the present day combining Swiss tradition with global maceutical ingredients both chemically and biotechnologically. Biophar- experience, the company has had an enterprising character, adapting maceuticals are one of the key growth drivers of the pharmaceutical and its offerings and services to the needs of customers and to changing biotechnology industries. technologies. Throughout our history, we have maintained a strong culture of performance, results and dependability that is valued by all Lonza has strong capabilities in large and small molecules, peptides, of our customers. amino acids and niche bioproducts which play an important role in the development of novel medicines and healthcare products. In addition, Lonza’s cracker in Visp is the back bone of a comprehensive fully back- Lonza is a leader in cell-based research, endotoxin detection and cell ward integrated chemical network. Our product portfolio consists of therapy manufacturing. Furthermore, the company is a leading provider HCN- and diketene derivatives as well as basic chemicals which are key of chemical and biotech ingredients to the nutrition, hygiene, preserva- raw materials and intermediates for many sophisticated applications. tion, agro and personal care markets. 3 Diketene and HCN derivatives, heterocycles and basic chemicals catalog Diketenes / ketenes Diketene is a colorless liquid produced by dimerization of ketene. It is Alkylamides: Aliphatic amines react with diketene to result in alkyl- a highly reactive building block which can be combined with numerous amides. Major products such as monomethyl- or dimethylacetoacet- other chemical compounds to make a wide range of products. Because amides are manufactured as aqueous solutions with continuous pro- of its high energy content, transport of diketene is forbidden. It is pro- cesses; other derivatives and water-free compounds are produced with cessed further at the site of manufacture. Lonza is one of the world’s batch processes. The (alkyl-) acetoacetamides are used principally in leading suppliers of diketene derivatives manufactured in its production the manufacture of insecticides. The derivatives are also deployed in facility in Visp, Switzerland. Our diketene derivatives are used in the the pigment, pharmaceutical and polymer industries. pharmaceutical, vitamin, agrochemical and pigment industries. The niche markets are in cosmetics, plasticizers, paints. The acetoacyl group DHS / NaDHS: The catalytic dimerization of diketene yields dehydroacetic in diketene derivatives has a broad functionality which can be used acid (DHS), which is a solid material. The free acid can be neutralized for the production of further products. Lonza’s most comprehensive with sodium hydroxide and is available as the salt NaDHS or its monohy- diketene product lines are those made with alcohols (aceto-acetic acid drate NaDHS-H2O. These products are used above all in the manufacture and acrylate derivatives), aliphatic amines (alkylamides) and aromatic of PVC stabilizers and as preservatives in the cosmetic industries. amines (arylamides). Lonza uses some of these to produce further components (pyrazolones, aminocrotonates, side chains). Acrylic acid esters (acetoacetoxy monomers): Acetoacetoxyethyl meth- acrylate (AAEMA), the most important product of this group, is made The following summary provides an overview of the diketene derivative in a multipurpose batch production plant. It is used as a copolymer for product groups: coatings and adhesives in emulsion polymerization (waterborne disper- sions) or solvent polymerization (high solids), and provides improved Diketene esters (acetoacetates): “Major” products such as methyl, mechanical and solvent resistance to water or organic solvents. It also ethyl, isopropylester of acetoacetic acid are produced in a continuous promotes adhesion to metallic, mineral and wood surfaces. process and purified by distillation. “Minor” derivatives are produced batchwise in stirred vessel reactors. The products are used mostly in Other diketene derivatives: 4-Chloroacetoacetic acid ester is a highly the dye, agrochemical, pharmaceutical and vitamin industries. versatile diketene derivative. It can be used in syntheses of various pharmaceutical intermediates. Arylamides: A large variety of arylamides are obtained by the reaction of aromatic amines with diketene. Our most important products are AAA, Ketene: Lonza has the specific capability to perform a variety of reac- AAOT, AAMX, AAOA, and AAOC; others are made regularly or on special tions with ketene. The production of ethyl 4, 4, 4-trifluoroacetoacetate request. These derivatives are used mainly in the production of azo is one example for such a ketene reaction. pigments; but also in the dye and agrochemical industries. For more information about ketene / diketene chemistry and its various derivatives, please ask for specific brochures and related literature or send mail to [email protected]. 4 Hydrocyanic acid (HCN) Hydrogen cyanide is a extremely poisonous colorless or pale-blue liquid that undergoes a wide variety of reactions. Lonza has manufacturing capabilities to offer a solution of hydrogen cyanide in water (hydrocy- anic acid) and producing its derivatives. HCN is used in metallurgical and photographic processes. Furthermore, HCN is a starting material for cyanogen chloride, cyanoacetates, cyanohydrins, sodium cyanide, chelating agents and many more. Cyanogen chloride is a functional building block for other Lonza products like cyanuric chloride and malo- nonitrile. The cyanohydrins, give access to a variety of useful organic compounds including the monomer methyl methacrylate, amino acids via the Strecker synthesis, and the chelating agents EDTA and NTA. Basic chemicals Beside ketene and HCN chemicals Lonza’s cracker related product port- folio also offers a selective number of basic chemicals. The chemicals can be used as starting materials and processed further to yield coat- ings, colorants, adhesives, medicines, agrochemicals and more. Icons Pharma Colorants Agriculture Polymers Nutrition Various 5 Diketene and HCN derivatives, heterocycles and basic chemicals catalog Methyl acetoacetate (MAA) Ethyl acetoacetate (EAA) Diketene / Esters C H O C H O ketene 5 8 3 5 10 3 derivatives Molecular weight 116.12 130.14 CAS RN 105-45-3 141-97-9 Minimum assay 99.0 % 99.0 % Minimum stability 2 years 2 years Melting point ca. –28°C –43°C Boiling point ca. 170°C 180°C Density g/cm3 (20°C) 1.077 1.03 EU labeling Xi irritant – Packaging drums, bulk drums, bulk Transport information not restricted not restricted Isopropyl acetoacetate (IPAA) Isobutyl acetoacetate (AAisobutyl) t-Butyl acetoacetate (AA-t-butyl) C7H12O3 C8H14O3 C8H14O3 Molecular weight 144.17 158.20 158.20 CAS RN 542-08-5 7779-75-1 1694-31-1 Minimum assay 98.5 % 98.0 % 98.0 % Minimum stability 2 years 2 years 2 years Melting point ca. –27°C –20.5°C –38°C Boiling point ca. 185°C 205°C 71°C / 15hPa Density g/cm3 (20°C) 0.998 0.974 0.970 EU labeling Xi irritant – – Packaging drums, bulk drums drums Transport information not restricted not restricted not restricted N-Benzyl-N-methyl-2-aminoethyl- Benzyl acetoacetate (BAA) acetoacetate (AABME) Dodecyl acetoacetate (AAdodecyl) C11H12O3 C14H19NO3 C16H30O3 Molecular weight 192.22 249.31 270.42 CAS RN 5396-89-4 54527-65-0 52406-22-1 Minimum assay – 95.0 % 96.0 % Minimum stability 2 years 8 months 2–3 years Melting point ca. 12°C – – Boiling point ca. 275°C dec. 175°C dec. 190°C /20 hPa Density g/cm3 (20°C) 1.114 1.067 0.914 EU labeling Xi irritant – Xi irritant Packaging drums drums drums Transport information not restricted not restricted not restricted 6 2-Methoxyethyl acetoacetate 4-Nitrobenzyl acetoacetate Ethyl benzoylacetate-91 (BESethyl-91) (AAmethoxyethyl) (30 % in toluene) (PNBAA 30T) C11H12O3 C7H12O4 C11H11NO5 Molecular weight 192.22 160.16 237.21 CAS RN 94-02-0 22502-03-0 61312-84-3 Minimum assay 91.0 % 97.5 % 270-330 g/l Minimum stability 2 years 2 years 9 months Melting point ca. – – – Boiling point ca. 93°C / 10 Pa 118°C / 26hPa – Density g/cm3 (20°C) – 1.091 – EU labeling – T toxic F, Xn; R11-38-48/20-63-65-67 Packaging drums drums iron drums 56.25 kg, 187.5 kg Transport information not restricted not restricted UN 1993, 3, PG II Acetoacetanilide (AAA) Acetoacetanilide, flakes( AAA,flakes) Arylides C10H11NO2 C10H11NO2 Molecular weight 177.20 177.20 CAS RN 102-01-2 102-01-2 Minimum assay 99.5 % 95.0 % Minimum stability 2 years 9 months Melting point ca. 83.0°C 62.0°C Boiling point ca. – – Density g/cm3 (20°C) – – EU labeling Xn harmful Xn harmful Packaging paper bags, big bags big bags Transport information not restricted not restricted Acetoacet-o-toluidide (AAOT) Acetoacet-m-xylidide (AAMX) C H NO C H NO 11 13 2 12 15 2 Pharma Colorants Agriculture Molecular weight 191.23 205.26 CAS RN 93-68-5 97-36-9 Minimum assay 99.5 % 99.5 % Polymers Minimum stability 2 years 2 years Melting point ca. 103.5°C 89°C Boiling point ca. – – Nutrition Density g/cm3 (20°C) – – EU labeling Xn harmful Xn harmful Various Packaging paper bags, big bags paper bags, big bags Transport information not restricted not restricted 7 Diketene and HCN derivatives, heterocycles and basic chemicals catalog Acetoacet-4-chloro-2,5-dimethoxy- Acetoacet-o-chloroanilide (AAOC) Acetoacet-o-anisidide (AAOA) anilide (ASIRG) Diketene / C H ClNO C H NO C H ClNO ketene 10 10 2 11 13 3 12 14 4 derivatives Molecular weight 211.65 207.23 271.70 CAS RN 93-70-9 92-15-9 4433-79-8 Minimum assay 99.5 % 99.5 % 98.0 % Minimum stability 2 years 2 years 2 years Melting point ca.
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