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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 diketene@lonza.com.
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
N-Benzyl-N-methyl-2-aminoethyl-
Benzyl acetoacetate (BAA) acetoacetate (AABME) Dodecyl acetoacetate (AAdodecyl)
6
2-Methoxyethyl acetoacetate 4-Nitrobenzyl acetoacetate
Ethyl benzoylacetate-91 (BESethyl-91) (AAmethoxyethyl) (30 % in toluene) (PNBAA 30T)
C11H13NO2 C12H15NO2
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 / C10H10ClNO2 C11H13NO3 C12H14ClNO4
ketene
derivatives
N,N-Dimethylacetoacetamide
N-Methylacetoacetamide (MMAA) (DMAA-80) N,N-Diethylacetoacetamide (DEAA)
8
Acetoacetamide (AAmid) 3-Methyl-5-pyrazolone (MP)
C8H7O4Na C8H9O5Na
Pharma
Colorants
Agriculture
Molecular weight 190.13 208.15
CAS RN 4418-26-2 64039-28-7
Minimum assay 99.0 % 98.0 % Polymers
Minimum stability 2 years 2 years
Melting point ca. – 109°C
Boiling point ca. – – Nutrition
Density g/cm3 (20°C) – –
EU labeling Xn harmful Xn harmful Various
Packaging drums drums
Transport information not restricted not restricted
9
Diketene and HCN derivatives, heterocycles
and basic chemicals catalog
Diacetoacet-1,4-phenylenediamide Diacetoacet-2,5-dimethyl-1,4-
Diacetoacet-o-tolidide (DiAA-o-tolidid) (DiAAphen) phenylenediamide (DiAA DM)
10
Diacetoacet-2-chloro-5-methyl-1,4- Diacetoacet-2,5-dichloro-1,4-
phenylenediamide (DiAA MC) phenylenediamide (DiAA DC) Methyl 3-aminocrotonate (ACMe)
1,4-Butyleneglycolbis Thiodiglycolbis
(3-aminocrotonate) (BGAC) Diketene-acetone adduct (DAA) (3-aminocrotonate) (TGAC)
2,5-Dimethyl-2,4-dihydro-
pyrazol-3-on (DMPO) Ethyl 4-chloroacetoacetate (CAAEt)
C5H8N2O C6H9ClO3
Pharma
Colorants
Agriculture
Molecular weight 112.13 164.59
CAS RN 2749-59-9 638-07-3
Minimum assay >98.0 % 97.0 % Polymers
Minimum stability – 1 year
Melting point ca. 117–118°C –8.5°C
Boiling point ca. 105–115°C / 8 hPa 220°C Nutrition
Density g/cm3 (20°C) 1.14 1.212
EU labeling Xi irritant T toxic, N environment Various
Packaging – drums
Transport information not restricted UN-No.: 2922, 8, PG II
11
Diketene and HCN derivatives, heterocycles
and basic chemicals catalog
Methyl 4-methyl-3-oxopentanoate
(OPMe, 4-methyl)
C7H12O3
Pharma
Colorants
Agriculture
Molecular weight 144.17
CAS RN 42558-54-3
Minimum assay 98.0 % Polymers
Minimum stability 12 months
Melting point ca. –75°C
Boiling point ca. 192°C Nutrition
Density g/cm3 (20°C) 1.01
EU labeling – Various
Packaging drum or iso-container
Transport information not restricted
12
2-Methoxyethyl cyanoacetate
Allyl cyanoacetate (CNESallyl) Butyl cyanoacetate (CNESbutyl) (CNES methoxyet)
13
Diketene and HCN derivatives, heterocycles
and basic chemicals catalog
Molecular weight – – –
CAS RN 68391-11-7 68391-11-7 68391-11-7
Minimum assay – – –
Minimum stability – – –
Melting point ca. – – –
Boiling point ca. – – –
Density g/cm3 (20°C) 0.978–0.990 1.018–1.034 1.024–1.038
EU labeling – – –
Packaging iron drum, bulk iron drum, bulk iron drum, bulk
Transport information not restricted not restricted not restricted
14
Niacin min. 99.5 % (NS fg) Niacinamide USP (NSA USP) Meta™ metaldehyde (META tc)
4,6-Dimethoxy-2-[(phenoxy-
Pyrimidine (<0.5 % water) carbonyl)amino]pyrimidine
(Pyrimidine W<0.5) (ADMP-carbamat)
C4H4N2 C13H13N3O4
Pharma
Colorants
Agriculture
Molecular weight 80.09 275.26
CAS RN 289-95-2 89392-03-0
Minimum assay 98.5–100.0 % 97.0–101.0 % Polymers
Minimum stability 2 years 2 years
Melting point ca. 20–22°C 120–122°C
Boiling point ca. 122–24°C > 250°C Nutrition
Density g/cm3 (20°C) 1.016 –
EU labeling – – Various
Packaging drums drums
Transport information not restricted not restricted
15
Diketene and HCN derivatives, heterocycles
and basic chemicals catalog
Acetaldehyde (AcAl) Acetic acid (glacial) (ES 99) Acetic anhydride (ESanhydrid)
Basic C2H4O C2H4O2 C4H6O3
chemicals
HNO5S C3H4O4
16
2,6-Diethyl-4-methylaniline (DEMA) 2,6-Diisopropylaniline (DIPA) 4,4-Dimethoxy-butan-2-one (DMB)
Others C11H17N C12H19N C6H12O3
Valeronitrile (VN)
C5H9N
Pharma
Colorants
Agriculture
Molecular weight 83.13
CAS RN 110-59-8
Minimum assay 99.5 % Polymers
Minimum stability 2 years
Melting point ca. –
Boiling point ca. 139–141°C / 1013 hPa Nutrition
Density g/cm3 (20°C) 0.7990
EU labeling – Various
Packaging drums, bulk
Transport information not restricted
17
Diketene and HCN derivatives, heterocycles
and basic chemicals catalog
Alphabetical index
A D
6
1 Acetaldehyde AcAl 9 Dehydroacetic acid DHS
16 Acetic acid (glacial) ES 99 9 Dehydroacetic acid sodium salt monohydrate NaDHS-H2O
16 Acetic anhydride ESanhydrid 9 Dehydroacetic acid sodium salt NaDHS
9 Acetoacetamide AAamid 11 Diacetoacet-2-chloro-5-methyl-1,4-phenylenediamide DiAA MC
7 Acetoacetanilide AAA 11 Diacetoacet-2,5-dichloro-1,4-phenylenediamide DiAA DC
8 Acetoacet-4-chloro-2,5-dimethoxyanilide ASIRG 10 Diacetoacet-2,5-dimethyl-1,4-phenylenediamide DiAA DM
8 Acetoacet-5-chloro-2-methoxyanilide AAMOC 10 Diacetoacet-1,4-phenylenediamide DiAAphen
7 Acetoacet-m-xylidide AAMX 10 Diacetoacet-o-tolidide DiAA-o-tolidid
8 Acetoacet-o-anisidide AAOA 8 N,N-Diethylacetoacetamide DEAA
8 Acetoacet-o-chloroanilide AAOC 10 Diethyl squarate QS, diethyl
7 Acetoacet-o-toluidide AAOT 16 2,6-Diethyl-4-methylaniline DEMA
10 2-(Acetoacetoxy)ethyl methacrylate AAEMA 11 Diketene-acetone adduct DAA
12 Adenine Adenine 16 2,6-Diisopropylaniline DIPA
14 Akolidine 10 Akolidine 10 16 4,4-Dimethoxy-butan-2-one DMB
14 Akolidine 11 Akolidine 11 15 4,6-Dimethoxy-2-[(phenoxy-carbonyl)amino]pyrimidine (ADMP-carbamat)
14 Akolidine 12 Akolidine 12 8 N,N-Dimethylacetoacetamide DMAA
13 Allyl cyanoacetate CNESallyl 11 2,5-Dimethyl-2,4-dihydro-pyrazol-3-on DMPO
14 2-Amino-4,6-dimethoxypyrimidine ADMP 9 3,5-Dimethylpyrazole DMP
13 3-Aminocrotononitrile Diacetonitril 6 Dodecyl acetoacetate AAdodecyl
16 Ammonia aqueous approx. 24.5–24.9 % chemically pure Ammonia 24
10 Ammonia techn. Ammonia tc E
6 Ethyl acetoacetate EAA
B 7 Ethyl benzoylacetate BESethyl
6 Benzyl acetoacetate BAA 11 Ethyl 4-chloroacetoacetate CAAEt
6 N-Benzyl-N-methyl-2-aminoethylacetoacetate AABME 14 5-Ethyl-2-methylpyridine MEP
13 Butyl cyanoacetate CNESbutyl 14 2-(5-Ethyl-2-pyridyl)ethanol PRD-2-etol, 5-Et
6 t-Butyl cyanoacetate AA-t-butyl 12 Ethyl 4,4,4-trifluoroacetoacetate ETFAA
11 1,4-Butyleneglycolbis(3-aminocrotonate) BGAC
H
C 14 6-Hydroxynicotinic acid NS,6-Hydroxy
4
1 2-Chloro-4,6-dimethoxypyrimidine DMP, 2-Chlor
13 Chlorosulfonyl isocyanate CSI I
12 Cyanuric chloride A CC A 6 Isobutyl acetoacetate AAisobutyl
12 Cyanuric chloride AS CC AS 6 Isopropyl acetoacetate IPAA
M
6
1 Malonic acid MA
13 Malononitrile (85 % in methanol) MDN
13 Malononitrile MDN
15 Meta™ metaldehyde META tc
7 2-Methoxyethyl acetoacetate AAmethoxyethyl
13 2-Methoxyethyl cyanoacetate CNES methoxyet
9 3-Methyl-5-pyrazolone MP
12 Methyl 3,3-dimethoxypropanoate PRSMe,DM
11 Methyl 3-aminocrotonate ACMe
12 (E)-Methyl 3-methoxyacrylate E-MMA
12 Methyl 4-methyl-3-oxopentanoate OPMe, 4-methyl
8 N-Methylacetoacetamide MMAA
6 Methyl acetoacetate MAA
18
Page Product Abbreviation
N
5
1 Niacin min. 99.5 % NS fg
15 Niacinamide USP NSA USP
16 Nitric acid 65 %
7 4-Nitrobenzyl acetoacetate (30 % in toluene) PNBAA 30T
16 Nitrosylsulfuric acid 40 % SS,Nitrosyl 40
P
5
1 Paraldehyde PARA
15 2-Picoline Picoine,2
15 4-Picoline Picoline,4
8 Potassium N-(acetoacetyl)sulfanilate AAsulfanil-K
10 Propane-1,1,1-triyltrimethyl tris(acetoacetate) AATMP
15 Pyrimidine (<0.5 % water) Pyrimidine W<0.5
S
3
1 Sodium dicyanamide Na-dicyanamide
14 Sodium nicotinate NS-Na
10 Squaric acid QS
T
3
1 1,1,3,3-Tetramethylguanidine TMG
11 Thiodiglycolbis(3-aminocrotonate) TGAC
V
16 Valeronitrile VN
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