43:
318:
243:
57:
24:
945:
482:
567:
of this molecule has the carboxylic acid groups rotated out of the plane of the central benzene ring. The molecule adopts a propeller-like conformation in which the tilt of each carboxylic acid group relative to the central benzene ring varies due to intramolecular hydrogen bonding.
689:
forms the acid chloride, which crystallizes in needles, and melts at 190 °C. By heating the ammonium salt of the acid to 150–160 °C while ammonia is evolved, a mixture of paramide (mellimide, molecular formula
140:
495:
715:
is obtained. The mixture may be separated by dissolving out the ammonium euchroate with water. Paramide is a white amorphous powder, insoluble in water and alcohol.
872:
768:
367:
965:
960:
341:
InChI=1S/C12H6O12/c13-7(14)1-2(8(15)16)4(10(19)20)6(12(23)24)5(11(21)22)3(1)9(17)18/h(H,13,14)(H,15,16)(H,17,18)(H,19,20)(H,21,22)(H,23,24)
351:
InChI=1/C12H6O12/c13-7(14)1-2(8(15)16)4(10(19)20)6(12(23)24)5(11(21)22)3(1)9(17)18/h(H,13,14)(H,15,16)(H,17,18)(H,19,20)(H,21,22)(H,23,24)
332:
719:
603:
502:
275:
296:
453:
730:
686:
564:
530:
931:
238:
982:
634:
180:
712:
666:
80:
49:
313:
42:
106:
63:
718:
The high stability of mellitic acid salts and their presence as an endproduct of the oxidation of
750:
577:
56:
918:
Kurmoo M, Estournes C, Oka Y, Kumagai H, Inoue K (2005) Inorganic
Chemistry volume 44, page 217
901:
839:
627:
891:
881:
792:
615:
544:
390:
29:
284:
200:
116:
937:
V.III: The
Chemistry of the Hydrocarbons and their Derivatives on Organic Chemistry: P.V
317:
242:
160:
783:
Bart, J. C. J. (1968). "The crystal structure of a modification of hexaphenylbenzene".
682:
662:
658:
473:
976:
956:
951:
896:
867:
443:
433:
231:
854:
812:
723:
722:, which are present in the solar system, make them a possible organic substance in
611:
685:
it gives carbon dioxide and benzene. Long digestion of the acid with an excess of
264:
654:
638:
589:
796:
413:
191:
599:
541:
905:
886:
23:
650:
631:
623:
596:
581:
211:
220:
969:. Vol. 18 (11th ed.). Cambridge University Press. p. 95.
592:
585:
552:
537:
534:
423:
251:
738:
619:
547:
of the acid. It crystallizes in fine silky needles and is soluble in
171:
472:
Except where otherwise noted, data are given for materials in their
950:
This article incorporates text from a publication now in the
661:
do not react with it. It is decomposed, on dry distillation, into
548:
151:
139:
129:
866:
S. A. Benner; K. G. Devine; L. N. Matveeva; D. H. Powell (2000).
734:
607:
526:
301:
55:
41:
929:
Henry
Enfield Roscoe, Carl Scholemmer, "Mellitene Group", "
841:
Beiträge zur chemischen
Kenntniss der Mineralkörper, Band 3
618:. The acid may also be prepared by the oxidation of pure
826:
Determination of
Organic Structures by Physical Methods
490:
824:
Brown, H.C., et al., in Baude, E.A. and Nachod, F.C.,
576:
Mellitic acid may be prepared by warming mellite with
375:
O=C(O)c1c(c(c(c(c1C(=O)O)C(=O)O)C(=O)O)C(=O)O)C(=O)O
602:, and the ammonium salt of the acid purified by
448:678 °C (1,252 °F; 951 K) (calc.)
438:> 300 °C (572 °F; 573 K)
263:
873:Proceedings of the National Academy of Sciences
606:. The ammonium salt is then converted into the
115:
8:
614:, and the lead salt is then decomposed by
316:
241:
199:
15:
895:
885:
283:
808:
806:
868:"The missing organic molecules on Mars"
813:Curate Data: Predicted Properties: 2244
761:
372:
337:
312:
219:
778:
776:
741:have interesting magnetic properties.
232:
344:Key: YDSWCNNOKPMOTP-UHFFFAOYSA-N
179:
159:
7:
637:in the cold, or by hot concentrated
354:Key: YDSWCNNOKPMOTP-UHFFFAOYAB
254:
939::529. D. Appleton and Co. (1889).
466:5.0, 2.19, 3.31, 4.78, 5.89, 6.96
14:
828:, Academic Press, New York, 1955.
943:
785:Acta Crystallographica Section B
720:polycyclic aromatic hydrocarbons
580:, boiling off the excess of the
480:
22:
729:Mellitates (and salts of other
476:(at 25 °C , 100 kPa).
649:It is a very stable compound;
1:
731:benzene polycarboxylic acids
529:first discovered in 1799 by
610:salt by precipitation with
540:(honeystone), which is the
37:
999:
523:benzenehexacarboxylic acid
418:342.16 g/mol
85:Benzenehexacarboxylic acid
844:(in German). p. 114.
797:10.1107/S0567740868004176
470:
428:1.68 g/cm, 2.078 (calc.)
383:
363:
328:
99:
91:
79:
74:
36:
21:
687:phosphorus pentachloride
531:Martin Heinrich Klaproth
966:Encyclopædia Britannica
932:A Treatise on Chemistry
887:10.1073/pnas.040539497
769:MSDS for mellitic acid
681:; when distilled with
635:potassium permanganate
60:
46:
595:is filtered off, the
588:to the solution. The
59:
45:
81:Preferred IUPAC name
50:Ball-and-stick model
64:Space-filling model
18:
751:Mellitic anhydride
713:ammonium euchroate
578:ammonium carbonate
503:Infobox references
61:
47:
16:
838:Klaproth (1802).
815:. ChemSpider.com.
791:(10): 1277–1287.
667:pyromellitic acid
628:hexamethylbenzene
604:recrystallization
584:salt, and adding
511:Chemical compound
509:
508:
297:CompTox Dashboard
141:Interactive image
70:
69:
990:
970:
949:
947:
946:
919:
916:
910:
909:
899:
889:
880:(6): 2425–2430.
863:
857:
852:
846:
845:
835:
829:
822:
816:
810:
801:
800:
780:
771:
766:
710:
709:
708:
700:
699:
616:hydrogen sulfide
493:
487:
484:
483:
391:Chemical formula
321:
320:
305:
303:
287:
267:
256:
245:
234:
223:
203:
183:
163:
143:
119:
38:
30:Skeletal formula
26:
19:
998:
997:
993:
992:
991:
989:
988:
987:
973:
972:
959:, ed. (1911). "
955:
944:
942:
927:
925:Further reading
922:
917:
913:
865:
864:
860:
855:WebElements.com
853:
849:
837:
836:
832:
823:
819:
811:
804:
782:
781:
774:
767:
763:
759:
747:
707:
704:
703:
702:
698:
695:
694:
693:
691:
680:
676:
672:
653:, concentrated
647:
574:
561:
512:
505:
500:
499:
498: ?)
489:
485:
481:
477:
462:
407:
403:
399:
393:
379:
376:
371:
370:
359:
356:
355:
352:
346:
345:
342:
336:
335:
324:
306:
299:
290:
270:
257:
226:
206:
186:
166:
146:
133:
122:
109:
95:
87:
86:
66:
52:
32:
27:
12:
11:
5:
996:
994:
986:
985:
975:
974:
957:Chisholm, Hugh
926:
923:
921:
920:
911:
858:
847:
830:
817:
802:
772:
760:
758:
755:
754:
753:
746:
743:
705:
696:
678:
674:
670:
663:carbon dioxide
659:hydriodic acid
646:
643:
573:
570:
560:
557:
519:graphitic acid
517:, also called
510:
507:
506:
501:
479:
478:
474:standard state
471:
468:
467:
464:
460:
450:
449:
446:
440:
439:
436:
430:
429:
426:
420:
419:
416:
410:
409:
405:
401:
397:
394:
389:
386:
385:
381:
380:
378:
377:
374:
366:
365:
364:
361:
360:
358:
357:
353:
350:
349:
347:
343:
340:
339:
331:
330:
329:
326:
325:
323:
322:
314:DTXSID50199650
309:
307:
295:
292:
291:
289:
288:
280:
278:
272:
271:
269:
268:
260:
258:
250:
247:
246:
236:
228:
227:
225:
224:
216:
214:
208:
207:
205:
204:
196:
194:
188:
187:
185:
184:
176:
174:
168:
167:
165:
164:
156:
154:
148:
147:
145:
144:
136:
134:
127:
124:
123:
121:
120:
112:
110:
105:
102:
101:
97:
96:
94:Graphitic acid
93:
89:
88:
84:
83:
77:
76:
72:
71:
68:
67:
62:
53:
48:
34:
33:
28:
17:Mellitic acid
13:
10:
9:
6:
4:
3:
2:
995:
984:
983:Benzoic acids
981:
980:
978:
971:
968:
967:
962:
961:Mellitic Acid
958:
953:
952:public domain
940:
938:
934:
933:
924:
915:
912:
907:
903:
898:
893:
888:
883:
879:
875:
874:
869:
862:
859:
856:
851:
848:
843:
842:
834:
831:
827:
821:
818:
814:
809:
807:
803:
798:
794:
790:
786:
779:
777:
773:
770:
765:
762:
756:
752:
749:
748:
744:
742:
740:
736:
732:
727:
725:
721:
716:
714:
688:
684:
668:
664:
660:
656:
652:
644:
642:
640:
636:
633:
629:
625:
621:
617:
613:
609:
605:
601:
598:
594:
591:
587:
583:
579:
571:
569:
566:
558:
556:
554:
550:
546:
543:
539:
536:
532:
528:
524:
520:
516:
515:Mellitic acid
504:
497:
492:
475:
469:
465:
459:
455:
452:
451:
447:
445:
444:Boiling point
442:
441:
437:
435:
434:Melting point
432:
431:
427:
425:
422:
421:
417:
415:
412:
411:
395:
392:
388:
387:
382:
373:
369:
362:
348:
338:
334:
327:
319:
315:
311:
310:
308:
298:
294:
293:
286:
282:
281:
279:
277:
274:
273:
266:
262:
261:
259:
253:
249:
248:
244:
240:
237:
235:
233:ECHA InfoCard
230:
229:
222:
218:
217:
215:
213:
210:
209:
202:
198:
197:
195:
193:
190:
189:
182:
181:ChEMBL1231329
178:
177:
175:
173:
170:
169:
162:
158:
157:
155:
153:
150:
149:
142:
138:
137:
135:
131:
126:
125:
118:
114:
113:
111:
108:
104:
103:
98:
90:
82:
78:
73:
65:
58:
54:
51:
44:
40:
39:
35:
31:
25:
20:
964:
941:
936:
930:
928:
914:
877:
871:
861:
850:
840:
833:
825:
820:
788:
784:
764:
728:
724:Martian soil
717:
648:
612:lead acetate
590:precipitated
575:
565:conformation
562:
522:
518:
514:
513:
457:
100:Identifiers
92:Other names
655:nitric acid
639:nitric acid
572:Preparation
563:The stable
384:Properties
239:100.007.495
161:CHEBI:41089
757:References
600:evaporated
414:Molar mass
285:P80QSP14DM
192:ChemSpider
128:3D model (
107:CAS Number
645:Reactions
559:Structure
542:aluminium
977:Category
906:10706606
745:See also
701:(CONHCO)
651:chlorine
632:alkaline
624:graphite
597:filtrate
582:ammonium
525:, is an
212:DrugBank
117:517-60-2
954::
711:), and
593:alumina
586:ammonia
553:alcohol
538:mellite
535:mineral
533:in the
496:what is
494: (
454:Acidity
424:Density
408:
252:PubChem
221:DB01681
948:
904:
894:
739:cobalt
620:carbon
491:verify
488:
368:SMILES
172:ChEMBL
75:Names
897:15945
733:) of
630:, by
549:water
333:InChI
152:ChEBI
130:JSmol
902:PMID
737:and
735:iron
683:lime
665:and
657:and
608:lead
551:and
545:salt
527:acid
276:UNII
265:2334
201:2244
963:".
892:PMC
882:doi
793:doi
669:, C
626:or
521:or
302:EPA
255:CID
979::
935::
900:.
890:.
878:97
876:.
870:.
805:^
789:24
787:.
775:^
726:.
671:10
641:.
622:,
555:.
463:)
456:(p
406:12
398:12
908:.
884::
799:.
795::
706:3
697:6
692:C
679:8
677:O
675:6
673:H
486:N
461:a
458:K
404:O
402:6
400:H
396:C
304:)
300:(
132:)
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
