273:
180:
36:
27:
470:
759:
575:
473:
475:
733:
determined its correct formula, Laurent gave it its present name. Manufacturing methods in the nineteenth century included oxidation of naphthalene tetrachloride with nitric acid, or, better, oxidation of the hydrocarbon with fuming sulfuric acid, using mercury or mercury(II) sulfate as a catalyst.
906:
Several melting points are reported, for example: (i) 480. K (NIST website), (ii) 210â211 °C with decomposition (Sigma-Aldrich on-line), (iii) 191 °C in a sealed tube (Ullmann's
Encyclopedia of Industrial Chemistry), (iv) 230 °C with conversion to phthalic anhydride and water
999: : 113-125. (Note: The empirical formulae of the compounds that were analyzed in this article are incorrect, in part because, during this period, chemists used incorrect atomic masses for carbon (6 instead of 12) and other elements.)
474:
476:
484:
1062: : 76-99; on page 92, Laurent coins the name "acide phtalique" (phthalic acid) and admits that his earlier empirical formula for phthalic acid was wrong.
588:
922:
547:
498:
322:
973:
725:
naphthalene tetrachloride. Believing the resulting substance to be a naphthalene derivative, he named it "naphthalic acid". After the
1041:(1) : 13-20. (Note: Again, Marignac's empirical formulae are wrong because chemists at this time used incorrect atomic masses.)
583:
939:
730:
287:
117:
595:
670:
1093:
844:
774:
555:
230:
175:
1052:"Sur de nouvelles combinaisons nitrogénées de la naphtaline et sur les acides phtalique et nitrophtalique"
1207:
251:
920:
Lorz, Peter M.; Towae, Friedrich K.; Enke, Walter; et al. (2007). "Phthalic Acid and
Derivatives".
420:
187:
1073:"Ueber neue stickstoffhaltige Verbindungen des Naphtalins, ĂŒber PhtalinsĂ€ure und NitrophtalinsĂ€ure"
674:
268:
26:
1030:
852:
439:
1202:
743:
988:
967:
1072:
1051:
1009:
1054:(On new nitrogenous compounds of naphthalene, and on phthalic acid and nitrophthalic acid),
665:. Although phthalic acid is of modest commercial importance, the closely related derivative
778:
750:, gives Phthalic anhydride, which, through hydrolysis with hot water, gives Phthalic acid.
747:
239:
48:
8:
1187:
157:
83:
1075:(On new nitrogenous compounds of naphthalene, on phthalic acid and nitrophthalic acid),
1031:"Ueber die NaphtalinsĂ€ure und ein bei ihrer Darstellung entstehendes flĂŒchtiges Produkt"
876:
272:
179:
137:
93:
839:
802:
790:
782:
705:
666:
645:
551:
539:
1083:(1) : 98-114; on page 108, Laurent coins the name "PhtalinsÀure" (phthalic acid).
1138:
935:
857:
682:
619:
608:
527:
1033:("On naphthalinic acid and a volatile product that arises during its preparation"),
927:
848:
829:
678:
623:
523:
409:
345:
931:
718:
669:
is a commodity chemical produced on a large scale. Phthalic acid is one of three
661:
517:
219:
1133:
786:
566:
1196:
977:. Vol. 21 (11th ed.). Cambridge University Press. pp. 545â546.
962:
398:
168:
698:
1131:
497:
1161:
726:
694:
543:
483:
35:
490:
370:
188:
148:
966:
834:
722:
296:
InChI=1S/C8H6O4/c9-7(10)5-3-1-2-4-6(5)8(11)12/h1-4H,(H,9,10)(H,11,12)
1020:(1) : 38-50; for the preparation of phthalic acid, see page 41.
781:. Typically phthalate esters are prepared from the widely available
565:
Except where otherwise noted, data are given for materials in their
306:
InChI=1/C8H6O4/c9-7(10)5-3-1-2-4-6(5)8(11)12/h1-4H,(H,9,10)(H,11,12)
616:
456:
116:
715:
650:
491:
388:
206:
758:
712:
128:
106:
256:
1121:(3rd ed.). Philadelphia: W. B. Saunders. p. 602.
693:
Phthalic acid is produced by the catalytic oxidation of
895:
Determination of
Organic Structures by Physical Methods
893:
Brown, H.C., et al., in Baude, E.A. and Nachod, F.C.,
1163:
Microbial degradation of polyvinyl chloride plastics
1132:Richard N. McDonald and Charles E. Reineke (1988).
919:
16:Aromatic organic compound with formula C6H4(COOH)2
1194:
1094:"Oxidation of Naphthalene to Phthalic Anhydride"
218:
1071:Reprinted in German as: Auguste Laurent (1842)
1008:Reprinted in German as: Auguste Laurent (1836)
801:The toxicity of phthalic acid is moderate with
472:
92:
923:Ullmann's Encyclopedia of Industrial Chemistry
708:and a subsequent hydrolysis of the anhydride.
1169:(Ph.D.). Quaid-i-Azam University. p. 47.
1010:"Ueber NaphthalinsÀure und ihre Verbindungen"
989:"Sur l'acide naphtalique et ses combinaisons"
773:s of 2.89 and 5.51. The monopotassium salt,
1159:
1012:(On naphthalenic acid and its compounds),
271:
178:
156:
915:
913:
238:
991:(On naphthalic acid and its compounds),
961:
957:
955:
953:
951:
757:
1188:International Chemical Safety Card 0768
267:
1195:
1116:
910:
403:207 °C (405 °F; 480 K)
169:
948:
753:
299:Key: XNGIFLGASWRNHJ-UHFFFAOYSA-N
136:
711:Phthalic acid was first obtained by
789:in the presence of water gives the
309:Key: XNGIFLGASWRNHJ-UHFFFAOYAX
209:
13:
1056:Revue Scientifique et Industrielle
785:. Reduction of phthalic acid with
731:Jean Charles Galissard de Marignac
468:
14:
1219:
1181:
897:, Academic Press, New York, 1955.
811:
1134:"trans-1,2-Dihydrophthalic Acid"
1077:Annalen der Chemie und Pharmacie
1035:Annalen der Chemie und Pharmacie
993:Annales de Chimie et de Physique
573:
34:
25:
1153:
1125:
1110:
1086:
1065:
820:sp. P1 degrades phthalic acid.
742:Naphthalene, on oxidation with
569:(at 25 °C , 100 kPa).
1160:Ishtiaq Ali, Muhammad (2011).
1119:Chemistry of Organic Compounds
1044:
1023:
1002:
981:
900:
887:
869:
1:
932:10.1002/14356007.a20_181.pub2
863:
688:
53:Benzene-1,2-dicarboxylic acid
845:Potassium hydrogen phthalate
775:potassium hydrogen phthalate
766:It is a dibasic acid, with p
737:
7:
823:
808:(mouse) of 550 mg/kg.
375:166.132 g/mol
10:
1224:
1177:Merck Index, 9th ed, #7178
1148:, vol. 6, p. 461
1098:public.websites.umich.edu
796:
563:
509:
450:
338:
318:
283:
76:
59:
47:
42:
33:
24:
1117:Noller, Carl R. (1965).
675:benzenedicarboxylic acid
1050:Auguste Laurent (1841)
987:Auguste Laurent (1836)
974:EncyclopĂŠdia Britannica
926:. Weinheim: Wiley-VCH.
440:Magnetic susceptibility
1029:C. de Marignac (1841)
968:"Phthalic Acids"
777:is a standard acid in
763:
762:Phthalic acid crystals
744:potassium permanganate
479:
66:Benzene-1,2-dioic acid
1014:Annalen der Pharmacie
761:
478:
62:1,2-Benzenedioic acid
853:acidâbase titrations
779:analytical chemistry
748:potassium dichromate
461:(fire diamond)
330:OC(=O)c1ccccc1C(=O)O
49:Preferred IUPAC name
677:, the others being
410:Solubility in water
21:
1208:Dicarboxylic acids
840:Phthalic anhydride
791:1,3-cyclohexadiene
783:phthalic anhydride
764:
754:Reactions and uses
706:phthalic anhydride
667:phthalic anhydride
596:Infobox references
552:Phthaloyl chloride
540:Phthalic anhydride
510:Related compounds
480:
393:1.593 g/cm, solid
19:
1146:Collected Volumes
1139:Organic Syntheses
907:(J.T.Baker MSDS).
858:Terephthalic acid
683:terephthalic acid
620:dicarboxylic acid
609:organic chemistry
604:Chemical compound
602:
601:
535:Related compounds
528:Terephthalic acid
446:-83.61·10 cm/mol
252:CompTox Dashboard
118:Interactive image
1215:
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849:primary standard
830:Isophthalic acid
679:isophthalic acid
664:
643:
586:
580:
577:
576:
558:dicarboxaldehyde
524:Isophthalic acid
518:carboxylic acids
500:
493:
486:
471:
415:0.6 g / 100 mL
364:
346:Chemical formula
276:
275:
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877:"PHTHALIC ACID"
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719:Auguste Laurent
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591: ?)
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548:Phthalhydrazide
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1182:External links
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965:, ed. (1911).
963:Chisholm, Hugh
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71:-Phthalic acid
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20:Phthalic acid
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1203:Benzoic acids
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816:The bacteria
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613:phthalic acid
610:
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399:Melting point
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64:Phthalic acid
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1162:
1155:
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1118:
1112:
1101:. Retrieved
1097:
1088:
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1038:
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1017:
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817:
815:
800:
793:derivative.
767:
765:
741:
710:
704:directly to
699:
692:
612:
606:
556:Benzene-1,2-
457:
424:
383:white solid
77:Identifiers
68:
60:Other names
818:Pseudomonas
721:in 1836 by
695:naphthalene
544:Phthalimide
433:2.89, 5.51
380:Appearance
339:Properties
176:100.001.703
138:CHEBI:29069
1197:Categories
1103:2024-04-06
881:hazard.com
864:References
689:Production
371:Molar mass
240:6O7F7IX66E
149:ChemSpider
105:3D model (
84:CAS Number
835:Phthalate
738:Synthesis
723:oxidizing
646:structure
197:201-873-2
189:EC Number
824:See also
729:chemist
617:aromatic
516:Related
458:NFPA 704
451:Hazards
442:(χ)
716:chemist
671:isomers
649:HO(O)Câ
624:formula
622:, with
589:what is
587: (
421:Acidity
389:Density
365:
207:PubChem
94:88-99-3
938:
797:Safety
713:French
702:xylene
700:ortho-
662:C(O)OH
615:is an
584:verify
581:
323:SMILES
43:Names
1167:(PDF)
727:Swiss
288:InChI
129:ChEBI
107:JSmol
69:ortho
936:ISBN
851:for
847:, a
681:and
644:and
231:UNII
220:1017
928:doi
746:or
697:or
673:of
635:(CO
607:In
257:EPA
210:CID
158:992
1199::
1143:;
1136:.
1096:.
1081:41
1079:,
1058:,
1039:38
1037:,
1018:19
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971:.
950:^
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423:(p
1150:.
1106:.
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930::
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771:a
768:K
660:â
657:4
655:H
653:6
651:C
641:2
637:2
633:4
631:H
629:6
627:C
579:N
499:0
492:0
485:2
428:a
425:K
362:4
360:O
358:6
356:H
354:8
352:C
259:)
255:(
109:)
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