Chemical Reaction List

Diverse
Organic Synthesis
Technologies

Proposal of the most Appropriate Process for Customers based on our Diverse Reactive Technologies

Through results and experience as a custom manufacturer, we have amassed a great store of diverse reactive technologies including oxidation, reduction, Grignard reaction, halogenations, and cyanation reaction, all of which are at the top level among custom manufacturers in Japan. Recently we have been actively trying to establish new technologies such as optical resolution, asymmetric synthesis, and flow synthesis. Combining this wide range of organic synthesis technologies makes it possible to achieve efficient development of target products in response to our customers’ diverse and complex requirements.

Major Organic Synthesis Technologies

• Acylation
• Alkylation
• Allylation
• Amination
• Bromination
• Carboxylation
• Chlorination
• Condensation
• Coupling
• Cyanation
• Esterification
• Fluorination
• Formylation
• Hydroxylation
• (Meta) Acrylation
• Nitration
• Oxidation
• Optical Resolution
• Reduction
• Ring formation
• Sulfonation and Chlorosulfonation

Examples of Reactions Using the Above Technologies

Synthesis of complex compounds with a combination of multiple unit processes.

Reaction Example (1):

Naphthalenesulfonic acid → (Chlorination) → naphthalenesulfonyl chloride → (Reduction) → naphthothiol

Reaction Example (2):

Naphthol → (Reduction) → Hydroxy-decahydronaphthalene → (Allylation) → Allyloxy-decahydronaphthalene → (Oxidation) → Glycidyloxy-decahydronaphthalene

Reaction Example (3):

Aniline → (Amidation) → 1-Butyl aminobenzene → (Nitration) → 1-Butylamino-2-nitrobenzene → (Reduction) → 1-Butylamino-2-aniline → (Ring formation) → 2-Propylbenzene imidazole

Reaction Example (4):

2-hydroxy-6-naphthoic acid → (Bucherer reaction) → 2-amino-6-naphthoic acid → (Sandmeyer reaction) → 2-bromo-6-naphthoic acid

Low Temperature Reaction

It is possible to carry out reactions as low as -10゜C

Grignard Reaction

We have commercially established the Grignard reaction including preparation of Grignard reagents from Mg metals.

Cyanation Reaction

It is possible to provide various cyanide compounds under safe and effective operation including safely handling NaCN and KCN as well as detoxifying the wastewater system containing CN-.

Reactions with Metal Sodium

It is possible to safely use molten metallic sodium on an industrial scale and to prepare a dispersion solution.
The metal sodium reaction is available for both condensation and reduction.

Reduction

Reduction is one of our best unit processes. In particular, we have achieved excellent results with catalytic hydrogenation which is not harmful to the environment.

Halogenations

The production of various halogenated compounds is possible using technologies that are commercially established for chlorination, bromination, iodination, and fluorination.

Original Products

Dinaphthothiophene Derivatives

Dinaphthothiphene (DNT) is a compound with a very high refractive index (1.82 at 589nm) as a single organic chemical substance. We meet customers’ requirements by providing various derivatives of DNT with functional groups through our organic synthesis technologies. Representative derivatives are shown below.

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Naphthothiol Derivatives

Naphthothiol and its derivatives have a very high refractive index when compared with other organic compounds. In particular, the 1,6-derivative has both a high refractive index and good solubility (compatibility), and we can also supply various derivatives with polymerizable groups.

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Binaphthol Derivatives

Binaphthol derivatives have high value in use as organic compounds with a high refractive index, and we can supply various derivatives.

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Calixarenes

We have two main types of Calixarenes - S series (n=4,6,8) with a sulfonic group and B series (n=4,6,8) with a tert-butyl group.
We can also supply CALXB4-EA which is used as an additive for cyanoacrylate adhesive. Development of monomers with polymerizable groups is also possible. Representative derivatives are shown as below.

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Decaline Derivatives

We develop 2DH, 2DHA (acrylate), and 27DGDHN (glycidyl ether) which have high heat resistance and transparent properties. These Decaline derivatives are expected to be used in optical applications.