Triazîne Ring Goes Commercial - C&EN Global Enterprise (ACS

Nov 5, 2010 - American Cyanamid makes this cyanuric chloride under a licensing arrangement with Deutsche Gold- und Silber-Scheideanstalt (Degussa)...
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PRODUCTION

Triazîne Ring Goes Commercial American Cyanamid's cyanuric chloride offers its unique triazine ring for chemical exploitation A CHEMICAL t h a t has cured 100% of

^ * a certain type of rat cancer, a heat resistant plastic, an insecticide, a powerful optical bleach—these and many more new products can be made from a compound now being commercially produced for the first time a t American Cyanamid's Warners plant in New Jersey. American Cyanamid makes this cyanuric chloride under a licensing arrangement with Deutsche Goldund Silber-Scheideanstalt ( D e g u s s a ) . Cyanuric chloride is extremely reactive; must b e produced in a closed system to prevent hydrolysis with air-borne moisture. It is toxic upon hydrolysis, a severe irritant t o mucous membranes. Cyanuric chloride is made from hy-

drogen cyanide a n d chlorine. T h e hydrogen cyanide is produced at Warners from calcium cyanide brought down in hopper cars from Niagara Falls. Raw materials first react to form cyanogen chloride, hydrochloric acid. Cl 2 + 2HCN - > 2CNC1 -h 2HC1 This product mixture is fed to a stripper where acid and excess chlorine a r e removed, then to either of two converter feed tanks, kept at t h e proper temperature by circulating brine. A steam heated vaporizer is followed by a Dowtherm-heated super-heater. The cyanogen chloride vapor next passes through a b e d of carbon-type catalyst in a reactor, where it is changed to cyanuric chloride.

Drum loacling and obeclc weighing

American Cyanamid's Cyanuric Chloride Process

HCN CYANOGEN CHLORIDE

(CNCI) 3

VENT SCRUBBER

REACTOR, STRIPPER STRIPPED CYANOGEN CHLORIDE REACTOR FEED TANK

'COOLING WATER

REACTOR S^. FEED IT*" TANK DOWTHERM BRINE

BRINE HOOD

.STEAM

PRODUCT DRUM VAPORIZER

SUPERHEATER DOWTHERM

798

NaOH CIRCULATING PUMP BLOWER

CHEMICAL

AND

ENGINEERING

NEWS

Boost in Maleic Anhydride Yield Using new Scientific Design reaction system for maleic anhydride production, Reichhold plans to double output to about five million pounds per year A

Cyanuric scrubber

3 CNC1 —

CI—C

O-CI

II-

I

SI

N

Vs Cl A w a t e r - c o o l e d s c r a p e r condenser cools t h e v a p o r b e l o w t h e sublimation p o i n t , d r o p s t h e c r y s t a l l i z e d product into d r u m s . P r o d u c t i o n c a p a c i t y is in excess of a ton p e r d a y . T a n k a n d r e c e i v e r vent lines* sampling hoods, and drumming station h o o d a r e v e n t e d t h r o u g h a continuous c a u s t i c s c r u b b e r . P r o d u c t loss, corrosion, a n d d a n g e r from toxicity w o u l d result from system leaks. Main p r o d u c t i o n p r o b l e m is k e e p i n g the system tight. C y a n u r i c c h l o r i d e is an i n t e r m e d i a t e for t r i e t h y l e n e m e l a m i n e , a c o m p o u n d w h i c h h a s b e c o m e w e l l established as a d r u g for t r e a t m e n t of leulcemias a n d lymphomas. It h a s effected 1007c c u r e s o n c e r t a i n t y p e s of r a t cancers, t h e first t i m e a c h e m i c a l has s h o w n 1 0 0 % efficiency a g a i n s t anixnal c a n c e r . Clear, heat-stable plastics can b e m a d e from triallyl c y a n u r a b e , p r e p a r e d b y a l l o w i n g c y a n u r i c c h l o r i d e to r e a c t w i t h allyl alcohol. T A C c a n b& p o l y m e r i z e d b y itself, or c o p o l y m e r i z e d w i t h s t y r e n e , methacrylat«es, u n s a t u r a t e d a l k y d s . It also h a s p r o m i s e for u s e a s a n a n t i c o n v u l s a n t , insecticide, plasticizer. C o p o l y m e r s w r t h a m a l e i c a l k y d h a v e y i e l d e d resins w i t h excellent p r o p e r t i e s at t e m p e r a t u r e s to 500° F . C y a n u r i c c h l o r i d e is now used as a n i n t e r m e d i a t e in p r o d u c t i o n of d y e s , optical bleaches, pharmaceuticals, and h a s p o t e n t i a l for m o t h p r o o f i n g c o m p o sitions, s u r f a c t a n t s , explosives. The u n i q u e t r i a z i n e r i n g may encourage n e w a p p r o a c h e s t o m a n y o^ther c h e m i cal fields. VOLUME

?3,

NO.

8 •

M O D I F I E D R E A C T I O N s y s t e m for

the

-**- p r o d u c t i o n of m a l e i c a n h y d r i d e b y Reichhold has been completed. Cond u c t e d b y Scientific D e s i g n , t h e d e v e l o p m e n t p r o g r a m h a s led t o a p r o c e s s w h i c h , a c c o r d i n g t o R e i c h h o l d a n d Scientific D e s i g n , r e s u l t s in s u b s t a n t i a l l y i n c r e a s e d yields. T h e r e v a m p e d p r o c ess, w h i c h u s e s a n e w c a t a l y s t , is in operation at Reichhold's Elizabeth, N . J., p l a n t . B a s e d on t h i s p r o c e s s , Reichhold plans to expand the plant, m o r e t h a n d o u b l i n g its c a p a c i t y , t o a b o u t five m i l l i o n p o u n d s p e r y e a r . In t h e process used by Reichhold, b e n z e n e is o x i d i z e d in a fixed-bed r e a c tor. T h e resulting maleic anhydride v a p o r is s c r u b b e d w i t h w a t e r to r e m o v e m a l e i c a n h y d r i d e from t h e g a s ; a n d t h e s o l u t i o n is d e h y d r a t e d u n d e r s p e c i a l conditions. T h e crude maleic anhyd r i d e is purified b y f u r t h e r distillation, and then processed b y a pelleting mac h i n e . R e i c h h o l d is t h e first m a n u f a c t u r e r of m a l e i c a n h y d r i d e in p e l l e t form. M a l e i c a n h y d r i d e is u s e d in t h e m a n u f a c t u r e of a l k y d resins, p o l y e s t e r resins, f u n g i c i d e s , plasticizers, and numerous specialty chemicals. Scientific D e s i g n will u s e t h e s a m e

reactor design a n d t h e same catalyst as in u s e a t R e i c h h o l d ' s p l a n t in a maleic anhydride plant near Paris w h i c h t h e y will e n g i n e e r for t h e F r e n c h firm, Campagnie Francaise des M a t i e r e s C o l o r a n t e s , a s u b s i d i a r y of K u h l m a n n . T h e p l a n t will b e t h e sixth in w h i c h Scientific D e s i g n h a s t r a n s f e r r e d p r o c e s s d a t a from o n e s i d e of t h e A t l a n t i c to t h e o t h e r . Scientific Design has arranged with the F r e n c h firm to m a k e a v a i l a b l e i m p r o v e m e n t s d e v e l o p e d in t h e i r p l a n t to o t h e r licensees of S D in this field. Scientific D e sign says t h i s is t o a s s u r e a c o n t i n u i n g a n d fruitful i n t e r n a t i o n a l d e v e l o p m e n t in t h e m a n u f a c t u r e of m a l e i c a n h y dride. T h e Reichhold process and t h e process p l a n n e d for t h e F r e n c h p l a n t a r e a l i k e in t h a t b o t h r e p r e s e n t t h e b e s t balance between, performance a n d capit a l i n v e s t m e n t for p l a n t s of t h e i r si/.e, says Scientific D e s i g n . The central p r o b l e m in t h e R e i c h h o l d p r o j e c t w a s t h a t t h e p r o c e s s h a d b e e n in o p e r a t i o n for s e v e n y e a r s a n d r e p r e s e n t e d a c o n s i d e r a b l e i n v e s t m e n t in c a p i t a l e q u i p ment. Modifications w e r e t h u s m a d e within the existing physical structure.

Scientific Design's team, Alfred Saffer, research director; Robert Egbert, vice president in charge of engineering; and Mitchell Becker, group leader, look over plans for maleic anhydride production at Reichhold's Elizabeth, N. J., plant. I n developing t h e n e w modified reaction system, the Scientific Design team worked in close cooperation with t h e staff of Reichhold, including S. H. Baum, vice president; J. D . D'Angelo, plant m a n a g e r ; and Dexter Stud well, superintendent of t h e maleic anhydride plant

• FEBRUARY

2 1,

1955

799