Journ al of Scientifi c & Industri al Research Vol. 59, May 2000, pp 339-349
New Dimensions on Value Added Aldol Chemicals of Acetone
K V Ramanamurty and G S Salvapati * Coal Division, Indi an In stitut e of Chemical Technology, Hyderabad 500007, India
Aldol co nd ensati on of acetone provides a class of va lu e added chemicals: O'. , ~-un sa tur a t ed ketones and phenols. O'.,~ Unsaturated ket ones are formcd by va ri ous cross co ndensati on and Mi chael reacti ons of ald ol products with acetonc or betwccn themse lves and phenol s are formed by either condensation of acetone with meth anol or ~-k e t o-a l co h o l or iso propanaldehyde or by di enone-phenol rcarrangement of O'. , ~-un sa turated ketone such as isophorone or by alk ylati on of iso ph orone wi th mcthano l. These proccsses are hi ghl y eco-fri endly and economi ca ll y viab le and are also ve ry selecti ve. All th e products can be separated and recovered by di still ati on and opti onall y, a more va lu able ketone iso ph orone ca n be obtained frec of other products by selecti ve ly co nverting them bac k to th e startin g materi al acc tone, thu s abso lutely requiring no diluent treatment. All thesc processes highli ght many new dimensions in th e production and emergin g trends in the unconventi onal utility in wide range of industries ex tending to pharmaceutical , food and vege tab le and aillied industries.
Introduction ketones and phenols. Acetone is a cheaper raw mate ri al Acetone serves as an important industrial intenne and the processes for producing these compounds are diate leading to numerous chemicals, thus making it a hi ghly selective compared to the established industri al frontline raw material in many industries. There are many processes and it is abundantly available in India. HOCL reviews on acetone-based chemicals; it is not the inten produces 24,000 MT while Herdillia has a capacity of tion of this paper to add to this line. In recent years, ac 18 ,000 MT mostly by oxidation of cumene, NOCIL makes 14,000 MT from isopropyl alcohol I. Regarding etone is gaining significance as the starting material for the conventional end use pattern, 60% of the total de making selectively a,~-unsaturated ketones, wherein the mand is accounted by DAA, MIBK and methyl meth aldol products formed from acetone (Chart I) undergo acrylate. In this direction, the future production and end various cross condensation and Michael reactions with use potential of aldol products of acetone have been hi gh acetone or between themselves, leading to a variety of lighted. products and the production line extends to dimethyl and trimethyl phenol s by ecofriendly processes (water a.,~-Unsaturated Ketones from Acetone is the only byproduct) (Chart 2). These chemicals find many industrial applications and, in fact, the primary Auto-condensation of acetone proceeds by ald ol condensation product, 4-hydroxy-4-methyl-2-pentanone condensation which can be catalysed by acids as we ll as (diacetone alcohol, DAA) exhibits some wondeIi'u I prop bases. A large number of products (Chart I) are formed et1ies and it may be tenned as "viagra" to elephants. Thus, through either competitive paths at the addition-dehy the aim of this paper is to reveal new dimensions of these dration stage of diacetone alcohol itself or with the un aldol products of acetone in many areas in term s of th e used reactant, acetone. The major products in the reac versati Iity of the process, selectivity, ecofri endl i ness, tion are: diacetone alcohol , mesityl oxide, phorone, mesi absolutely requiring no efflu ent treatment and als o wide tylene, triacetone dialcohol , isophorone and isoxylitones range of industrial applications extending their utility in which have significant market pote ntiaj2 - I ~ (Table I). A pharmaceutical, food, vegetable and allied industri es in detailed di scussion on the reaction pathways of forma recent years. tion of these products has been reported earl ier"()ll. The basic raw material is acetone and under mild Though multiplicity of products arise in the product, re process conditions, the process is very viable for th e pro action can be optimised for the desired product through duction of two classes of compounds, a,~-unsaturated proper choice of process conditions (temperature, pres sure and catalyst) . . Author for correspondence 340 J SCI IND RES VOL S9 MAY 2000
Chart 1
Reaction pathways of formation of aldol products from acetone
1 Fonnation of Diacetone alcohol by aldol condensation of Acetone 000 2CH - C - CH -- (CH3}2C - CH - C- CH 3 " 3 ""2 3 2 Formation of Mesityl oxide by dehydration of Diacetone alcohol OH 0 0 CI " - H20 " (CH3}2 - CH2- C - CH3 --- (CH3}2C = CH - C - CH 3
3 Formation of Triacetone dialcoho! by aldo! condensation of Diacetone alcohol with Acetone o OH 0 " OH 0 OH I II + CH3 - C - CH3 I " I (CH }2 C - CH - C - CH .. (CH3)2C - CH - C - CH - C(CH }2 3 2 3 2 2 3 4 Fonnation of Phorone by dehydration of Triacetone Dislcohol
5 Fonnation of Phorone by aldol condensation of Mesltyl oxide with Acetone
6 Fonnation of Isophorone by 1,S-Michael cydization of Phorone o
c (CH3l,C=CH-tCH=C(CH3)2 - H3 D H3C CH3 7 Fonnation of Mesitylene from Mesityl oxide and Acetone by aldol condensation and 1,S-internal cydization reaction
Contd ..... RAMANAMURTY & SALVAPATI : VALUE ADDED ALDOL CHEM ICALS OF ACETONE 34 1
Chart 1-Contd
8 Formation of Semiphorone by dehydration of triacetone dialcohol
OH 0 OH OH 0 I II I I II C (CH 3)2 - CH 2 - C - CH2- C(CH 3) - (CH3)2C - CH 2 - C - CH =C(CH 3)2 9 Formation of Semiphorone by hydration of Phorone 0000 II I II C (CH3)2 =CH - C - CH = C(CH3)2 + H20 - (H3C}2C -CH2- C - CH = C(CH 3)2 10 Formation of t..ifetralone by reaction of Isophorone with Mesityl oxide o
HC A I C ~ 3 ~ + (CH3 )2 =CH-C-CH3 _ H3C CH 3 o 11 Formation of lsoxylitones by aldol condensation of lsophorone with Acetone
12 Formation of Isoxylitones by self,condensation of MesItyt oxide
13 Formation of 2,2,6,6,-Tetramethyl pyron-4-one by cydization of Semiphorone o
(C~3)2r CH,- g. CH = C (CH3l:. - . H3cDCH, H3C 0 CH 3
14 Formation of 3,3,6,8-Tetramethyl tetralone by reaction of lsophorone with Mesityl oxide
o C~ 0
H C + (CH3)2C=CH.tCH, 3~A C H3C CH3 H3 342 J SC I INO RES VOL S9 MAY 2000
Chart 2
Reaction paths of formation of phenols from acetone
Formation of m-Cresol by condensation of Methanol with Acetone
CH30H --- CH20 + H20
CH3·CO.CH3+ CH20 - CH3·CO.CH2·CHzOH
CH3·CO.CHz·CH20H --- CH3·CO.CH2·CHO + H2 OH
CH ·CO.CH ·CHO + CH ·CO.CH --- + 0 3 2 3 3 ~ 2H2 CH3 2 Fonnation of 3,5-Xylenol by condensation of ethanol with Acetone
CH3·CH2 0H - CH3·CHO + H2
CH ·CHO CH ·CO.CH - CH ·CO.CH ·CHOH.CH 3 + 3 3 3 2 3
CH3·CO.CH2·CHOH.CH3 - CH3·CO.CH2·CO.CH3 + H2 OH
+ + 0 CH,.CO.CH2CO.CH, CH,COCH, -~ 2H 2 C H3 CH 3 3 Fonnation of 3,5-Xylenol by die none-phenol rearrangement of lsophorone (fanned from Acetone) 0
H,cD + 2H20 C H3 CH 3 o 0 H,cD C H3 CH 3 H3Cn CH 3 4 Fonnatlon of 2,3,5-Trimethyl phenol and m~resol by disproportionation of 3,5-Xylenol OH OH OH
H~C ~ CH' ~ CH' + H,che::: 5 Fonnation of 2,3,5-Trimethyl phenol by alkylation of lsophorone with Methanol CH H,C + CH,OH -.. - , + CH, + H0 ~ k 2 H3C~CH3 H3C CH3 6 Fonnation of 2,3- and 2,5-xyIenols by decomposition of 2,3,5-Trimethyl phenol CH 2 + , + CH, ~ CH' ~(H' iir 2 H3C ~ CH3 CH 3 H3C RAMANAMURTY & SALVAPATI : VAL UE ADD ED ALDOL CHEMI CA LS OF ACETO E 343
Tab le I - Industri al app li ca ti ons of aldol chemicals from acetone
SI No. Produ ct Indus tri al Applications
Di acetone alcohol Bacteri cidal to S t a phyloco cc i ~
In bra kc fluid s 1 In polyv in ylacetate. styrene-butadiene latex compositions· In printing ink s without envi ronm ent al haza rd s' In corrosion in hibiting paints, leuco vat dyes compositions" 2 Mes it yl ox ide As so lvent and plas ti ciser in PVC formul ati ons7 In paint remover formulations and in remov ing resins or chl orin ated rubber coatin ti ngs' Perfume il nd fra grance co mpositionsY As solvent of' polymer in phenoli c resi ns, polys tryrenes, epoxy resins and pol yisoeyanates" l 3 Isophoron e In ph enol-form aldehyde and phenol furural res in s" In PVC compositions, swelling agent s'l Indu strial solven t for epoxy and phenoli c resins" Chl ori nat ed isophorone as fun gicide'· In making 3,5-xylenol and 2,3,5-trimeth yl ph enol'; 4 Mes it ylene In offse t press for cleanin g rubber bl ank et'" In di sinfecting and clean in g pastes' 7 5 Phorone As stimul an t for stem and leaf growth s in beans " Fo r dec reasin g th e storage breakdown of appl es'"
The formation of di acetone alcohol is equilibrium D e hydrati o n of triaceto ne dialcoho l y ie lds controlled so that reverse reacti on to acetone or dehy semiphorone. 2,2,6,6-Tetramethyl-pyron-4-one is the 2 dration to mesityl oxide can occur. Triacetone di alcohol cycli zation product of he miphoro ne '1 . Tetralone is is formed by the condensati on of acetone with diacetone formed by the reaction of mesityl oxiode with isoph orone alcohol, but it gets either reverted to acetone rapidly or with the loss of methane. Isoxylitones are formed by e i dehydrated to phorone over the catalyst. The condensa ther the condensation of acetone with isophorone or by 26 ti on reaction of acetone with mesityl oxide anion gives auto-condensation of mesityl oxide . phorone which can undergo I ,6-intemal Michael cycli za The processes in volving the formation of ald ol li on to isophorone. Isophorone can also be obtained products of acetone are govern ed by acid-base catalys is. through condensation of acetone ani on with mesityl ox The steps aimed at achieving th e selectivity of desired ide and subsequent 1,6-aldol reacti on. Mesilyle ne is product and process conditions have been reported in 2o 21 fo rmed by either condensation of acetone with mesityl detail earii er . • Now stage is set for th e ne xt step, sepa ox ide anion or acetone anion with mesit yl ox ide fo ll owed rati on of products. Aldolization of acetone constitutes 2 1 by 1,6-aldol reaction • such a versatile process whereby the process conditi ons As menti oned above, it is essential to exercise con can be very satisfactoril y achieved for obtaining th e de tTol over process conditions; otherwise th e reacti ons lead sired product. Though a , ~-un sa turated ketones and to hi gher condensation products. For example, self-con phenols synthesized from acetone differ significantly in densati on of mesityl oxide on ani on-exchange resin yields their boiling points and can be separated by di still ation, 22 4-isopropy I idene-3,5,5-tri methy 1- 2-cyclohexenone , the separation of ketones forms a separate entity by it mesityl ox ide can also dimerize over lithium 10 give 6- self. Isophorone can be separated from other ketones by 27 acetyl- I ,3,5,5-tetramethyl-2-cyclohaxanoF' . Formation distillation • If th e sample is coloured, decolourisation of2-acetyl- 1, ],3,4,4-pentaethylcyclo- pentene and 5-(2- may be effected by heating it to 90- ISO°C wi th acid methy I-I-propeny 1-) 2,4,4,5-tetrameth yl di hydrofuran fullers earth of pH 4.02X . In case mesityl oxide and 24 has also been reported . diacetone alcohol are to be removed, they can be freed .144 J SC I I D RES VOL 59 MAY 2000
Table 2 - In dustria l applications of phenols made from aeetone.lO.70
51 No. Product Industrial App li ca ti ons
III-Cresol For the production of thymol, methanol and III-t oluidinc") Startin g material for pcrfume fixat ive mu sk ambrcttc'O Antioxidant for polycthylcnc and pol ypropy lene-'o Ch loroderi vat i vcs nrc disi nfectant s and preserva ti vcs'o 2 3.5-Xylenol Fica repe ll cnt ' ) Lamin ating paper ad hesivcs'! Antimi crobial powders, salves, deodourant sprays" Di sinfectant and clea ning pastes and antiseptic shampoos'" Antioxidan t for butadienc-styrenc, but adiene-acrylonit ri lc po lymcrs'. In copolymers with urca, furans and form aldehydc''; 3 2,J ,5-Trimcthyl phenol In thc sy nthcs is of vit am in P " In making leuo dyc thcrmo-rccording IlHllCrial ,7 In thc manufac ture of cpoxy rcsin s" In rad iati on sensiti vc res in co mpositions''! In fungicidal compos iti onsW 4 2,5-X ylcnol As a stabili zcr to polyo lerins agai nst heat and light") In injecti on mouldablc phenoplast co mposi ti ons"! In di sinfcctant compositions for use in poultry and anim al hu sbandry',J In hair dye compositi ons·' As antiviral agcn t aga inst herpes-meas les-influenza-and sancari os virus'" As stab ili scr to vi nyl chl oridc res in s"" 5 2,J-Xylcnol As antioxidan t and li ght stabi lizer for polyoxadiazonc fibrcs, sheets and mou ldings"7
In mak ing cpoxy hased and po lyurethane elect ri ca ll y insulati on coatings 6X In fungicidal co mposi ti ons"'! In pcrfume composit ions70
by treatment at 130-200DC with sufficient amount of 0. 1N etone. Further, if by chance, hi gher condensation prod NaOH solution so that they are converted back to ac ucts - isoxylitones - are formed in the process, they can 2 D etone without affecting isophorone ') . If the product is to be hydrolysed with 2.6% alkali solution at 175 C under J2 be cleansed of mesityl oxide and phorone, treatment with a pressure of 10 atm to give isophorone . Thus, produc 3% aqueous FeCI or NH C1 soluti on at 100DC reverts tion of a,p-unsaturated ketones from acetone is economi 1 4 them to acetone, whil e isophorone remain s unchanged call y viabl e and a very eco-friendly process since all the in the solutionJ(). byproducts can be converted back to acetone and th e Another interesting fact is th at the product can be effluents contain onl y water and do not necessiate any freed of mesitylene by azeotropic di stillation with ace treatment. J I ti c acid . Thus, a more va luable ketone, isophorone, can Phenols from Acetone be recovered optionall y from the product while other Phenols are valu able industrial intermediates ketones are reverted back to th e starting compound, ac- (Table 2) for obtaining various bactericidals, polymers, RAMANAMURTY & SALVAPATI : VALUE ADDED ALDOL CHEM ICALS OF ACETONE 345
res in s, dyestuffs, etc. A number of processes such as acetone to isophorone and dienone-phenol rearrangement alkl ylation of phenol" , sulphonati on of benzene homo of isoph orone to 3,5-xy lenol. These processes gave 80% 34 logues , hydrodealkylati on of polya lkylated phenols" , yield of3,5-xylenol at 95% selectivity4('. The aromatiza ox id ation of aromatic hydrocarb ons'(', pyrol ys is of ti on ac ti vit y of these metal ox ides is ascri bed to 17 Mannich bases of 2-methyl cyclohexanones , cal'ulytic coordinatively un saturated cati on sites (e.g. Cr}+), ac conversion of aromati c carboxy lic ac id s}X, etc. are avail compani ed by the formation of carbanion which rear ab le for makin g phenol s. Phenol s can also be sourced ran ges to the di enone leading fin all y to 3,5-xy lenol. Jt is from tars of low temperature carbonization of Indi an also found that the aromati zati on reaction is a fun cti on coals·w . Phenol contents can vary from 30% in of the extent of c..}+s pec ies present on th e surface of th e 47 Koth agudem coals (S in gareni Collieries) to 40% in catalys t . I11-Creso I and 2,3 ,5-tri meth y I phen ol are l ambad -Bow la or upper Kajora coals. About 62 indi formed in the reacti on by di sproportionati on of 3,5- vidual phenols such as cresols, dimeth yl- , trimeth yl- , xylenol. Alternatively, 2,3,5-trimethyl phenol can also eth yl-phenols, 4,5-indanols, meth yl dih ydri c phenols be prepared by methylation of 3,5-xylenol with metha have been characterized and separated by Rao et 01. 40 nol (Tabl e 3). A sin gle step process by alkylati on of (Indi an In stitute of Chemical Technology, Hyderabad). isophorone with methanol has also been reported to give However, it is not viable to produce any individual phe 2,3,5 -trimeth ylphenoI4x . The mechani sti c pathway fo r nol from coal tars. In thi s context, it is menti oned th at thi s reaction is not yet established. It is possible that 2,3 ,5- processes have been developed and patented for the se trimethyl phenol formation can be routed in wh ich lective preparati on of alkyl phenols, in particular, 0- isophorone is aromatized to 3,5-xylenol which in turn 41 cresol, 2,6-x ylenoI , 2,3,6-trimeth yl phenol and 3,5- gets methylated to 2,3,5-trimethylphenol, or isophorone 42 xy lenol . itself can get methylated foll owed by dienone-phenol 4 Ph enol, m-cresol, 2,5 xy lenol and 3,5-xylenol can rearrangement leading to 2,3,5-trimethyl phenoI with acetone to give CH}.CO.CH 1.CH10H. This com Patterns in the End-use of Aldol Chemicals pound yields read il y CH}CO.CH1CHO, which in turn , condenses with acetone to yield phenol and water in the The final scenario regarding the ald ol chemic.als product (Table 3). Similarly, catalytic condensati on of centres round the new dimensions in the end-use pattern 44 eth anol with acetone gives 3,5-x ylenoI . of two classes of compounds - phenols and a , ~-un sat m-Cresol can also be prepared by urated ketones. The end-use pattern of phenol is: about cyclocondensati on of acetone with a ~-ketoalcohol over 60% in the manufacture of phenolic res ins, 10% in alky l D FeoO - AI ?O catalyst at 400 C. The required ~- phenol s, 7% in epoxy resin s and 4% in tanning agents. - } -} ketoalcohol, 2-butanone-4-01 can be obtained by the re- The utility is now increasingly bein g ex tended to per ac ti on of acetone and fo rmaldehyde in 60-62 % yield . sonal and health care market which is gaining @ 10% 4 7.6% yield of phenol is reported at 24.5% conversion 'i . annually. Phenols are increas in gly finding applications Phenols can also be prepared by dehydrogenation in such areas as eye make-up, hair toni cs and dyes, mouth condensat ion of acetone with isopropanaldehyde over wash , ge rmicides in soap, deodourants, shampoos, bio chromi a supported on magnesia. Phenol, l11-cresol, 3,5- cides and in sect repellantsx7. However, the aldol prod xy lenol and m-ethyl phenol can be prepared in 12-34% ucts besides possessin g indu strial applications are up 4 yield } • holding th eir utility in nascent areas. Diacetone alcohol Phenols, in general 3,5-xylenol, can be prepared is reported to affect chemi cal communications among selective ly from acetone in hi gh yield s (Table 3). Sev As ian Elelph antsXX eliciting Flehm an response and erec eral improved processes have been developed and pat ti on in elephants wit h amazin g effect, indicatin g its po ented with various catalysts such as magnesia, nickel tenti al use in pharmaceutical industry. White crystallil e chromium-iron, chromia-alumin a, etc. 42. 1n principle, the reaction products of urea, acetone and mes ityl oxide in reaction takes place in two steps, dehydrocyclization of the proportion 1-10% are used either directl y or di spersed 346 J SCI I D RES VOL 59 MAY 2000 Table 3 - Proven processes and selectivities of aldol chemicals of acetone SI No. Aldol Catalyst React ioll Reactor, reaction Yield Selectivi ty Ref. chemical tcmp.oC pcriod (h) (%) (%) Diacetone a metal n Batch 26.7 92.1 7 1 l (3gr of feed 5 Ca(OHh:Ba(OHh,8H1O 20 Flow 12- 13 100 72 ( I : 1- 15 ) (NA)* BaO 0 batch 22.9 100 7.' 1.5 2 Mesityl SiCIjZn powder Room tcmp. Lab. Batch 25.9 60.n 7-1 oxide ZnO - Zr01 (82: I ~ % ) 450 0.8 Adiabatic 17.9 77.2 75 l Oxides / hydroxides of Ce, ISO (LHSV 0.7#h· ) K, Zr, Hf, Ta, C r I h batch 15.9 87.4 76 Z110-Cr10.1 300 (NA) Fixed bed 14.2 ~7.7 77 Activated wilh Fe10.1 (LHSV 0.3#h' l) :I Isophorol1e Alkali hydroxide 240 Fixed bed Flow 13.8 54.9 7'11. (93 Ig/h) (0.36 h) Fixed bed 2 1.8 64.5 79 LHSV 2.0#h' l Fixed bed 13.7 36.0 !lO LHSV) 4 Phorone AICI, . 10% Roomlemp. Lab. balch 22 24 8 1 5 Mesilylene HCI 200 Balch 39 3 1 X2 (NA) AI 10 .1+ IO %Mo0.1 253 Fixed bed 38 74 83 (28 atm) (LHSV 0.99#h' l) 6 3,5-Xylenol Lithium phosphale 530 Fixed ved 75.4 80.7 84 (NA) MgO 580 Fixed bed 74.2 82.S 42 (LHS V 1.0) Fixed bed 79.6 83.2 42 (LHSV 0.5#h' l) 7 2.3.5- Magnesium 400-600 Fixed bed 8.6 A 85 Trimelhyl carbonalc / Mg (OH)2 (LHSV 0.1-3) phenol Cr10-Alp, / Cr10.r CuO :iOO-600 Fixed bed 100 ~6 7.6 3 1 45 8 III-Cresol Fe20.rAI10.1 400 Fixed bed NA = Dala not availahle RAMANAMURTY & SALVAPATI : VALUE ADDED ALDOL CHEMICALS OF ACETONE 347 in edible feeds for cattle, sheep, foxes, minks, skumps providing facilities to carry out this work and giving and poultry animalsx9 . permission to publish this paper. India is the second largest (next to China) producer References of vegetables (33 million tonnes) with a share of 13.38% Chem WeekLy, ( 19 May 1998),49. in total global output. It is also a large producer of fruits 2 Cooper E A, J Soc Chem Ind, 64 ( 1945) 51. (47 million tonnes), accounting for 10% of the world 3 Reynault L, Fr Pat, 872,936, 23 June 1946; Chem Abstr, 43 production. India occupies top position with regard to (1949) 4791. mangoes, bananas, grapes and chikku. But, our country 4 Tess R W & Schwartz R D, Off Dig Fed Paints Varnish Prod is a very poor global player and its global market share CLubs, 29 (1957) 1346; Chem Abstr, 53 (1959) 13621. is a meagre I %. It is worth noting that only 1.3% of the 5 Jones R T & Clifford T J (Jr), US Pat, 4,990,186 (to Eastman total fruits are processed against 40% in the developed Kodak Co), 05 February 1991 ; Chem Abstr, 114 ( 1991 ) 166563. countries. Though many reasons are given for these short 6 Me Aulay A E, US Pat, 2,615,815 (10 Shell Development Co) 28 falls, it needs attention for remedy regarding the use of October 1952; Chem Abstr, 47 ( 1953) 2120. obsolete technology, traditional methods of processing, 7 Charony & Circy, Fr Pat, 982,926 (to Socieli anon des manufac lack of awareness with respect to scientific methods, etc. tures des glorces et products Chemique de Saint Go bain), 18 Aldol products of acetone show promising trends in this June 1951; Chem Abstr, 49 (1955) 4332. area also. To brief a few, phorone is reported to stimu 8 Swiss Pat, 292,806 (to Reinturex A.-G.), 16 November 195 3; late greatly the stem and leaf growth in beanslx. It also Chem Abstr, 51 ( 1957) 3880. showed marked reduction in the disorders regarding core 9 Kanehira K, Fujita Y, ElIr Pat, 231 ,896 (to Kuraray Co. Ltd) 12 flush, superficial scald and bitter pit in apples. It also August 1987; Chem Abstr, 108 ( 1988) 166977. l9 decreased storage breakdown in apples too. Aldol 10 Edelenj & Wolfran E, Rodando EOI/'os Niminatac Sect Chilli. 11 chemicals are also found useful as perfume and fragrance (1969) 125; Chem Abstr, 73 ( 1970) 110369 Nakatsy, Y & Miura, compounds. They are reported to impart roasted chicken S, Japan Pat, 6,927,471 (to Teijin Ltd), 14 November 1969; like odour to certain food preparations911 . Chem Abstr, 72 ( 1970) 112239. II Sevestri J, Double diasiall No.97 ( 1963) 61; Chem Abstr, 66 Diacetone a1coholls bactericidal to staphylococei, ( 1967) 66798 and it considerably increases the bactericidal action of 12 Br Pat, 799,374 (to CIBA Ltd) 6 August 1958; Chem. Abstr, 53 phenol'JI. The condensation product of diacetone alco ( 1959) 2638, Sen-I-Gakkaishi 13 ( 1957) 8; Chan Abstr, 52 ( 1958) 5829. hol with urea, diacetone monourea, is reported to im 13 Kohl C F Jr, US Pat, 2,686,739, 17 August 1954; Chelll Abstr, prove the egg laying capacity of hens92. Chlorionated 48 ( 1954) 14295. isophorones are fungicides l4 . Isophorone is a selective insecticide against Ceratitis capitata, Daens olenc, 14 Hawley R S, US Pat, 2,583,435 (to Standard Oil Development Co.), 22 Jan uary 1952; Chem Abstr, 46 ( 1952) 5252, Ger Pat, Rhagoletis cerasi and Anastopha ludens but has limited 1,012,113 (to ESSO Research and Engineering Col), II Jul y affect on Musca domesfica (housefly) 93 . 1957, Chem Abstr, 54 ( 1960) 16730). 15 Salvapati G S , Ramanamurty K V, Janardanarao M & Hence, it may bp. concluded that acetone provides Vaidyeswaran R, Ind Pat, 167,840 (10 CSIR), Yoshida Y, Japan a potential source of a class of aldol chemicals a,~- un·, Pat, 08,245,486 (to Daicell Chem Japan), 24 Sept 1996; Chel/l saturated ketones and phenols which be"ides being very Ab.l'tr, 126 ( 1997) 7740; N etll Pal , 6 ,713 ,25 3 (Shell important indmtrial intemediates show f!eW dimensions Intemationale Research Maat schappij NV) 0 I April 1968; Chem Abstr, 69 ( 1968) 96221. in their uti! i::y i.!1 pharmaceutical, foC'd ,'/ eget~ble and 16 Helmond V & Johannel PC M, Neth Pat, 7,113,138; 27 March allied indust { ~ e~ . The Jrocesses are ver;' ecofriendly leav 1973; Chel/l Abstr, 79 (1973) 67649. ing p' ~. s~d(, ;]!"Iyjuct except water necessiating nc efflu 17 Vinarski i M S, Mikitenko L N, Kochergin V A, Bibll L M & e 1.t treat ,!,F; n ~ . 'Che processp.s <> fP. als0 so versatile that by Kuznetsova T I, USSR Pat, 467,927 (From Otkrytiya lzobrct proper Gi'.oice process :; o rlli itlon ~ the reaction can be ::Jf prom Obraztsy Tovarnye Znaki, 52 ( 15) ( 1975) 46) 25 April o~timized for the desired produc~ . 1975; Chell! Abstr, 83 ( 1975) 117634. Acknowledgement 18 Worley J F & Drowne M E, Nature, 223 ( 1969) 1386. The authors thank Dr K.V Raghavan, Director, 19 Wills R B H & Scott K J, J Hort Sci, 49 (2) ( 1974) 11 9: Chem Indian Institute 'J~ Chemlcal Technology, Hyderabad for Abstr, 81 ( 1974) 146785. 348 J SCI IND RES VOL 59 MAY 2000 20 Salvapati G S & Janardanarao M, 1 Sci Ind Res, 42 (1983) 261. 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