Fundamental processes of dye chemistry. 1949

454 TABLE XVI.

: co	ceo
	«U !*o
	¥
	.ceo
Zn or Al	^co^

O;JDNH2

See Table XIX

		N02		N02
		,0:0
				C6H5N(CH3)2
		NO2 T		NH2
		O:O
		X NH;. T		NH2
		'W^i
		AoXj
				Ice, then
				saponification >
		OHwn		\jnOH
			,co^^OH
		H03S ^^00^^,-
		HOWCO' GS03H
	Anthracene blue SWX OH			OH
	Alizarin cyanine S
Indanthrene dark blue BD		OH		OH
		(^CO^oH
		"°^OHC0^>OH
		Anthracene blue WR
		Alizarin cyanine
Compound		Principal Use
1. Benzanthrone		Vat dyes
2.	foz-1-Chlorobenzanthrone	Vat dyes
3.	Isodibenzanthrone (indanthrene violet R)	Vat dye
4. Dibenzanthrone (indanthrene dark blue BO)		Vat dye
5.	Dibenzopyrenequinone (indanthrene golden	Vat dye
	yellow GK) (No. 1, Table XV)
6.	1,4,5,8-Tetraaminoanthraquinone	Acetate dye
7. Anthracene blue SWX (alizarin cyanine S)		Mordant dye

Derivatives of Anthraquinone

	A1C13	CO
COAx1	p. 225
	Oleum + Hg	Ger. Pat. 149801
	p. 230
Na2S ceo	See Table XVII
		NH2

455

* O

oco

See Table XVIII

NHCOCfiHs

NHCOC6H5

NHCOC0H5

C«HnCOHN ~. Indanthrene yellow GK

O

NHCOC6H5

Indanthrene yellow 3GF

NH2	I /—\
	NH-( ^CH3

Anthraquinone blue SR SO-H

C«H5COHN OH

Algol brilliant red 2B

Compound

8.Anthracene blue WR (alizarin cyanine)

9.Anthracene blue GG

10.Indanthrene yellow 3 GF

11.1,5-Diaminoanthraquinone

12.Anthraquinone blue SR

13.1,8-Diaminoanthraquinone

14.Indanthrene yellow GK

15.Algol brilliant red 2 B

Principal Use

Mordant dye Mordant dye

Vat dye

Vat dyes, acid wool dyes Acid wool dye

Vat dyes, acid wool dyes

Vat dye Vat dye

456

Algol orange R

Compound

1.2-Chloroanthraquinone

2.2-Aminoanthraquinone

3.l,3-Dibromo-2-aminoanthraquinone

4.Algol orange

5.2,6-Diaminoanthraquinone

6.Benzanthronequinoune

TABLE XVII.

cooS03H

Algol yellow GCN

Principal Use

Vat dyes

Vat dyes

Vat dyes

Vat dye

Vat dyes

Vat dyes

Derivatives of Anthraquinone-/?-sulfonic Acid

457

-cccr

OH

HO CCOC

Flavopurpurin

OH OH

OH OH

Alizarin brilliant cyanine R

H03S

- cor coo

			•	a:o
	OH	If <!§		OHJ^
OHnT	AnthrapurpurinOH
OH	OH

NH

Aniline

S03H

NH

	Erweco alizarin acid blue R
Compound		Principal Use
7. 1,2,6-Trihydroxyanthraquinone (flavopurpurin)		Mordant dyes
8.	1,2,4,5,6,8-Hexahydroxyanthraquinone	Mordant dye
	(alizarin brilliant cyanine R)
9.	1,2,7-Trihydroxyanthraquinone (anthrapurpurin)	Mordant dye
10. Erweco alizarin acid blue R		Acid wool dye

458 TABLE XVIII.

oco		p. 233		ceo
		NaClO3 + HC1 Ger. Pat. 205195		SO3H
	NH2		' ^' ^ NHCH3 v	w T u OH
gceoSee Table XIX			ceo	ceo
X
\		ceo	cco	ceo
ceo
	Cl	OCH3	T NHCH3	T OH

NH

Qcol cb kxXsco>xx

Alizarin astrol B

S03H

CH3

	Alizarin geranol B
Compound		Principal Use
1. Anthraquinoneacridone (No. 4, Table XIX,		Vat dyes
	and No. 9, Table XXI)
2.	Alizarin astrol B	Acid wool dye
3.	Alizarin geranol B	Acid wool dye
4.	4-Broino- 1-acetylmethylaminoanthraquinone	Vat dyes, acid wool dyes
5.	Alizarin rubinol R	Acid wool dye
6.	Alizarin irisol R	Acid wool dye
7.	a-Anthrol	Indigoid dyes

Derivatives of Anthraquinone-a-sulfonic Acid	459
Oleum -|- Hg Ger. Pat. 157123

cf. Table XVII

OH

OH

COO JSCO CCO I

C1

//_* C1 -2 I r^. »... OH . + I I Ger. Pat.

O 158531

^^OC6H5

T

NO7 ^ OC6H8(NO2)2 NO2 OH

~ CO^^ ^^JCO.

oco-

" OH

N02

OH NH2

Alizarin saphirol SE

Ger. Pat. 119228

CH3		OCOOH NHCOC6H5
Anthraquinone violet
\	Indanthrene brilliant violet BBK
Indanthrene Bordeaux B
	Compound		Principal Use
	8.	Anthraquinone violet	Acid wool dye
	9.	1,5-Dichloroanthraquinone	Vat dyes
	10. Indanthrene brilliant violet BBK		Vat dye
	11.	Alizarin saphirol B	Acid wool dye
	12.	Alizarin saphirol SE	Acid wool dye
	13. 1,8-Dihydroxyanthraquinone (chrysazin)		Pharmaceutical
	14.	1,4,8-Trihydroxyanthraquinone	Acid wool dyes

460	TABLE XIX.

o™^

1-Chloroanthraquinone

Ger. Pat. 162824

CO CO CO CO

Algol gray B

02N/ V-NH—( \N02

}-~A r~\

CO CO CO

tf

Helindone yellow RW

H2N /	VNH— /		\ NH2
)—(		)—(
CO	CO	CO	CO

/ Vc	--/^ V-NH— CO-/ \

CO CO CO CO

/ 3 V-CO NH-^		\-NH-/		V-NH ,-CO-Q	CO CO	CO CO	CO CO
	)—(		)—(
	CO	CO	CO	CO
	Indanthrene olive R					Helindone brown
Compound					Principal Use
1. Helindone yellow RW					Vat dye
2.	Algol grey B				Vat dye
3.	Indanthrene olive R				Vat dye
4.	Anthraquinoneacridone (No. 1, Table XVIII,				Vat dyes
	and No. 9, Table XXI)				Vat dyes, acid wool dyes, azo dyes
5.	a-Aminoanthraquinone(fast red AL base)
6.	Anthrapyridone				Vat dyes
7.	Helindone brown				Vat dye

Derivatives of a-Aminoanthraquinone

461

NH2

Algol yellow WG

_ NHCOCOOH

OlO

NHCOCOOH

COO

N02

			CH3
	Alizarin saphirol A	Alizarin pure blue B
Compound			Principal C/*e
8.	1-Aminoanthraquinone-2-sulfonic acid		Acid wool dyes
9.	4-Bromo-l-aminoanthraquinone-2-sulfonic acid		Acid wool dyes
10. Alizarin pure blue B			Acid wool dye
11.	2,4-Dibromo-l-aminoanthraquinone		Acid wool dyes
12.	Alizarin saphirol A		Acid wool dye
13.	Algol yellow WG		Vat dye
14.	1,4-Diaminoanthraquinone		Acetate dye, acid wool dyes, vat dyes
15. Indanthrene red 5 GK			Vat dye

462

TABLE XX.

OH

		Oleum
	'H	/~	Oleum + Hg \	OH
	AlizarinS	J^Hco ^T	Ger. Pat. 205965 ^ ..
				CO w^
		r-V^Y-^OH	^	V T^OH

CC&

OH

OH

OH

un

Reduction	f^f C° T^^l °H
i —	3
Ger. Pat. 90722	*X^^CO'
OH QH	/ OH
	Alizarin Bordeaux R
	1I
	OH
	Y^Y^OH
	J-Co-^
	OH
	1
	!_
	c/>

COOH

s,S03H

I Ger. Pat. 84509 Alizarin viridine FF

\°H Alizarin brilliant

Bordeaux R

^ OH

OH

Mn°2 OCO'

OH OH

Alizaril

n cyanine

OH

0CO

, OH

Quinizarin green

^^NRNH2^2 OHOH

£^FCiiS0 "

^^^^co^^

[ T OH NH2

COOH

Alizarin brilliant cyanine GG

Compound			Principal Use
1.	l,2-Dihydroxyanthraquinone-3-sulfonic acid	(alizarin S)	Mordant dye
2.	Alizarin viridine FF		Acid wool dye
3.	1,2,5,8-Tetrahydroxyanthraquinone (alizarin Bordeaux R)		Mordant dye
4.	Alizarin brilliant cyanine GG		Mordant dye
5.	l,2-Dihydroxyanthraquinone-5-sulfonic acid	(Erweco acid	Mordant dye
	alizarin red)
6.	1,2,5-Trihydroxyanthraquinone (alizarin brilliant Bordeaux R)		Mordant dye
7.	1,2,4,5,8-Pentahydroxyanthraquinone (alizarin cyanine R)		Mordant dye
8.	1,4-Dihydroxyanthraquinone (quinizarin)		Acid wool dyes

Derivatives of Alizarin		463
OH		OH
HN03
		-800;NO2
,a:o'		OH
CO^^ OH		A^ann orange A i *£
' co .	N02
,CO	^^ ~.r	Alizarin maroon
	lUrl

NH2

Alizarin garnet

oco-o

OH

S03H

OH

Alizarin heliotrope

OH

Compound

9.1,2-Dihydroxyanthraquinone (alizarin)

10.1,2,4-Trihydroxyanthraquinone (purpurin)

11.Alizarin heliotrope

12.4-Amino-l,2-dihydroxyanthraquinone (alizarin garnet)

13.Alizarin green S

14.3-Nitro-l,2-dihydroxyanthraquinone (alizarin orange A)

15.3-Amino-l,2-dihydroxyanthraquinone (alizarin maroon)

16.Alizarin blue S

Alizarin blue S

Principal Use

Mordant dye

Mordant dye

Acid wool dye

Mordant dye

Mordant dye

Mordant dye

Mordant dye

Mordant dye

464

TABLE XXI.

Derivatives of /?-Methylanthraquinone

465

OCQ

^C^crV^cH	II
n T
TTO\x^co^
N	^	CO'

Indanthrene golden orange G

Compound

1.Pyranthrone (indanthrene golden orange G)

2.l-Chloroanthraquinone-2-carboxylic acid

3.Dimethyl-meso-benzodianthrone

4.oHo-meso-Naphthodianthrone

5.meso-Anthradianthrone

6.Cyananthrol

p. 227

CCCr-

455583 f'^Tf'

\X^CO

Principal Use

Vat dye

Vat dyes ( acridones )

Vat dyes

Vat dyes

Vat dyes

Acid wool dye

Cl	Ger. Pat. 216715	CODCHCIj

ceo-

r^Vcov^cooH	COOH
Xx^CO'kx^^W.
	iCOOH

Compound		Principal Use
7.	Anthraflavone G	Vat dye
8.	Anthraquinonethioxanthone	Vat dyes
9.	Anthraquinoneacridone (No. 1, Table XVIII,	Vat dyes
10.	and No. 4, Table XIX)
	Same as No. 2
11.	l-Aminoanthraquinone-2-carboxylic acid	Vat dyes (acridones)

SUBJECT INDEX

Italicized page numbers refer to sections describing the synthesis of the substance in question.

Absorption spectrum, 48 Accounting, 371, 378 Acenaphthene, 1 l-Acetamino-8-naphthol-3,6-

disulfonic acid, 263 p-Acetaminophenol, 52 Acetanilide, 93, 130, 131 Acetoacetanilide, 140, 267 Aceto-p-phenylenediamine, 132

diazotization, 245 Acet-0-toluidide, 9, 67 Acet-p-toluidide, 52

Acetyl-H acid, see l-Acetamino-8- naphthol-3,6-disulfonic acid

Acid IV (C acid), see 2-Naphthyl- amine-4,8-disulfonic acid

Acid anthracene red G, 124, 294 Acid orange A, 262, 378

Air as oxidizing agent, 8 Aldehyde group, introduction, 10 Algol yellow WG, 323

Alizarin, 90, 314

Alizarin cyanine green G, 317 Alizarin pure blue B, 232 Alizarin saphirol B and SE, 319 Alkali fusion

apparatus, 86, 87 general, 88 oxidative, 90 partial, 89

side reactions, 89 Alkaline earth salts, 58

Alkoxy groups, introduction, 8 Alloys, iron, 363, 364

Alsace green J, 201 Aluminum, 364

Aluminum chloride, 60, 226, 227 Aluminum chloride-pyridine, 60 Aluminum sodium chloride, 60, 223

Amidonaphthol red G, 263 Amines

determination, 386 separation, 27

p-Aminoacetanilide, 132 1-Aminoanthraquinone, 59, 231 2-Aminoanthraquinone, 8, 58,

229, 321

technical observations, 229 l-Aminoanthraquinone-2-sulfonic

acid, 59 p-Aminoazobenzene, 270

diazotization, 245 l-Amino-2-bromo-4-p-toluidino-

anthraquinone, 233 l-Amino-2,4-dibromoanthraqui-

none, 60, 233

1-Amino-2,4-dimethoxy-5- chlorobenzene, 98 p-Aminodimethylaniline, 311

p-Aminodiphenylamine, diazotization, 249

Aminodiphenylaminesulfonic acid, 100

1-Amino-gamma acid, see 1,2-Di- amino-8-naphthol-6-sulfonic acid

Amino groups introduction, 8 orienting power, 52

protection by acylation, 67 Amino-H acid, see l,7-diamino-8-

naphthol-3,6-disulfonic acid 1-Amino-2-methylanthraquinone,

228

Aminonaphthalene-, see Naphthylamine

1-Amino-8-naphthol-2,4-disulfonic acid, 165, 207, 210

467

[

468	SUBJECT INDEX

l-Amino-8-naphthol-3,6-disulfonic acid, 3, 211, 213, 214

acetylation, 263 determination, 389

dyes from, 263, 288, 291 solubility, 214

p-toluenesulfonyl derivative, 407 l-Amino-2-naphthol-4-sulfonicacid,

80, 85, 178, 201 diazotization, 248

l-Amino-5-naphthol-2-sulfonic acid, 218

l-Amino-8-naphthol-4-sulfonic acid, 217, 220

2-Amino-5-naphthol-7-sulfonic acid, 204, 207

2-Amino-8-naphthol-6-sulfonic acid, 204, 207, 208, 286

Aminonaphtholsulfonic acids, determination, 389

p-Aminophenol, 78 2-Aminophenol-4,6-disulfonic acid,

153

4-Aminophenol-3,5-disulfonic acid,

202

Aminophenols, separation, 30 p-Aminophenyloxamie acid, 94 Aminophenyltolylaminesulfonic

acid, 100 p-Aminosalicylic acid, 156 Aminosulfonic acids

determination, 388 separation, 32

Ammonia, temperature-pressure curves, 92

Analysis of commercial dyes, 399 ff. Analysis of dyes, Knecht method,

392

Analytical procedures, 383 ff. Aniline

by catalytic reduction, 76 diazotization, 243, 259 from chlorobenzene, 76 from nitrobenzene, 75 solubility in water, 75 technical observations, 75

Aniline black, 76 Aniline-2,5-disulfonic acid, 106 Aniline-o-sulfonic acid, 122

Aniline-m-sulfonie acid, 120 Aniline-p-sulfonic acid, 126 o-Anisidine, 93, 99

Anisole, 8 Anthracene, 1, 224

Anthranilic acid, 174, 323, 330 Anthraquinone, 224, 226

halogen derivatives, 60 hydroxylamine derivatives, 58 hydroxyl derivatives, 58 monosulfonic acid derivatives, 56 sulfonation, 56, 228, 230, 234

Anthraquinone-1,5-disulfonic acid, 57, 234

Anthraquinone-1,6-disulfonic acid, 57

Anthraquinone-1,7-disulfonic acid, 57

Anthraquinone-1,8-disulfonic acid, 57, 234

Anthraquinone-2,6-disulfonic acid, 56

Anthraquinone-2,7-disulfonic acid, 56

Anthraquinone dyes, 314 ff. Anthraquinone series, orientation,

56

Anthraquinone-1-sulfonic acid, 56, 230

Anthraquinone-2-sulfonic acid, 56,

228, 314

1-Anthraquinonyloxamic acid, 231 Anthrarufin, see 1,5-Dihydroxy-

anthraquinone Antimony-lead, 365 Antipyrene, 129 Apparatus, materials for, 16 Aqua regia, 67 Armstrong-Wynne rule, 54 Arsenic acid, 58, 229 Arylsulfonamides, 52 Auramine G, 299 Auramine OO, 298

Aurine dyes, 155 Autoclaves, 350 ff.

general rules on use, 361 Azine dyes, 99 Azobenzene, 78, 125

Azobenzenedisulfonic acid, 123

SUBJECT INDEX

469

Azo dark green, 289 Azo dyes

general, 239-262 isolation, 257 ff. reductive splitting, 402 titration with TiCU, 394

Azo flavine FF, 272 Azosalicylic acid, 295 Azoxybenzene, 78 Azoxybenzenesulfonic acid, 123 Azo yellow, 273, 275

Azo yellow G, 276

B

Bakelite, 368

Baking process, 52, 84, 126, 181 apparatus, 181

Bechamp-Brimmeyr reduction, 77 Benzal chloride, 158

technical observations, 159 Benzaldehyde, 158 Benzaldehydedisulfonic acid, 303 Benzanthrone, 60

Benzene, 1 Benzene-m-disulfonic acid, 143 Benzene hexachloride, 62 Benzene compounds, 62 ff. Benzenesulfonic acid, 80

Bakelite process, 82 Benzidine, 124

by electrolytic reduction, 126 technical observations, 126 tetrazotization, 261

Benzidine-3,3'-dicarboxylic acid,

164

Benzidine-2,2'-disulfonic acid, 123, 294

technical observations, 124 Benzidine dyes, 285 ff. Benzidine rearrangement, 99 Benzidine-salicylic acid inter-

mediate, 285 Benzoic acid, 159

Benzo light blue 2GL, 279

Benzo light grey BL, analysis, 407 Benzopurpurin 4B, 294 Benzotrichloride, 159 o-Benzoylbenzoic acid, 225

Benzoyl chloride, 60 Benzpyrenequinone, 224 Benzyl alcohol, 159 Benzyl chloride, 159 Biebrich scarlet dyes, 279 Bindschedler's green, 312 Biphenyl, 61

Bismarck brown G and R, 282 Blending, 377

Bohn-Schmidt reaction, 60 Boiling point determination, 40 Boiling rods, 22

Boiling stones, 22 Boric acid, 59

esters, 59

Brilliant indigo 4G, 164 Brilliant sulfo flavine, 409 Brilliant yellow, 283 Bromination, 67

Bronze, 364

Bucherer reaction, 8, 182, 201, 203, 209

C acid (acid IV), see 2-naphthyl- amine-4,8-disulfonic acid

Caledon jade green, 8 Cancer of the bladder, 76 Carbazole, 1

Carbazole series, orientation, 60 Carbazole vat dyes, 60

Carbon tetrachloride, 66 Carboxylic acids, separation, 31 o-Carboxyphenylthiogylcolic acid,

330

Cast iron, 362 Catalytic oxidation, 171 Cements, 365 Centrifuge, 18

Chicago acid (SS acid), see l-Amino-8-naphthol-2,4- disulfonic acid

Chicago blue, 148 Chloramine yellow FF, 335 Chloranil, 67, 146 Chloranisidine P, 109 Chlorate, 67

Chlorinated rubber, 368

470	SUBJECT INDEX

Chlorination apparatus, 63 Chlorination hydrochloric acid, 65 Chlorination reactions

replacement of substituent groups, 67

solvents for, 66 Chlorine

nascent, 9, 67 toxicity, 66

2-Chloro-5-aminobenzoic acid, 169, 295

4-Chloro-2-aminophenol, 110, 406

2-Chloro-4-aminophenolbenzyl ether, 406

p-Chloroaniline, diazotization, 244 4-Chloro-2-anisidine, 109 1-Chloroanthraquinone, 57, 233 2-Chloroanthraquinone, 8, 57, 226 Chlorobenzene, 51, 58, 62

newer methods of preparation, 65 nitration, 90

technical observations, 65 p-Chlorobenzenesulfonic acid, 104 o-Chlorobenzoic acid, 169 p-Chlorobenzotrichloride, 67 2-Chloro-4-dimethylamino-

benzaldehyde, 119, 305 o-Chlorometanilic acid, 107 Chloronitro-, see also Nitrochloro- 2-Chloro-4-nitroaniline, 66 4-Chloro-2-nitroanisole, 109 2-Chloro-5-nitrobenzoic acid, 169 4-Chloro-2-nitrophenol, 109, 406 2-Chloro-5-nitrotoluene-4-sulfonic

acid, 53 oChlorophenol, 10, 67, 145

p-Chlorophenol, 10, 52, 58, 67, 145, 237

Chlorosulfonic acid, 84, 199 o-Chlorotoluene, 4, 9, 67, 163 p-Chlorotoluene, 52 2-Chlorotoluene-4-sulfonic acid, 53,

163

4-Chloro-2-toluidine, 164

6-Chloro-2-toluidine, 161, 164 Chrome brown R, 115 Chromic acid, 8

Chromium sulfate, 4

Chromocitronine, 124, 295 Chromotropic acid, see 1,8-Dihy-

droxynaphthalene-3,6- disulfonic acid

Chrysazin, see 1,8-dihydroxy- anthraquinone

Chrysene, 1 Chrysophenine G, 149, 283 Clayton yellow, 336

Cleaning of reaction vessels, 10 Cleve acids, see 1,6- and 1,7-Naph-

thylaminesulfonic acids Coal tar, 1

Columbia black, 187 Commercial dyes, analysis, 399 Compressed air, 373 Condensers, 22, 26

Congo red, 293 test paper, 395

Construction materials, 362 ff. Copper, 364

as catalyst, 88, 90 Costs, 372

calculation, 378 ff. Cotton, 368

Coupling reactions, general, 249 ff. p-Cresol, 52

o-Cresotinic acid, 155 Cuprous chloride, 161 Cyanosis, 76

D

Deep black V, 292 Dehydrothiotoluidine, 332 Dialkyl sulfates, 8 Diamine brown M, 286 Diamine fast red F, 286 Diamine green B, 288 Diamine pure blue, 148

1,4-Diaminoanthraquinone, 232

1,5-Diaminoanthraquinone, 237 Diaminodibenzyldisulfonic acid,

162, 284 Diaminodiphenylaminesulfonic

acid, 100 l,7-Diamino-8-naphthol-3,6-

disulfonic acid, 405

SUBJECT INDEX

471

l,2-Diamino-8-naphthol-6-sulfonic acid, 407

Diaminostilbenedisulfonic acid, 167, 283

Dianil brown 3GN, 286 2,5-Dianiline-3,5-dichloroquinone,

147 o-Dianisidine, 93, 99

diazotization, 261 DianthraqUinonylamines, 59 Diazoaminobenzene, 270 Diazosulfanilic acid, 128 Diazotization, 241 ff.

technical procedures, 259 Dibenzanthrone, 90 Dibenzopyrenequinone, 60 1,5-Dibenzoylaminoanthraquinone,

322

3,8-Dibenzoylpyrene, 223

2,5-Dichloroaniline, 109 diazotization, 244

1,5-Dichloroanthraquinone, 236

2,6-Dichlorobenzal chloride, 162

2,6-Dichlorobenzaldehyde, 162 technical observations, 163

o-Dichlorobenzene, 65, 72 m-Dichlorobenzene, 67 p-Dichlorobenzene, 65, 108 1,2-Dichlorobenzene-4-sulfonic

acid, 53 2,6-Dichloro-4-nitroaniline, 66 l,4-Dichloro-5-nitrobenzene, 93,

108

2,6-Dichlorotoluene, 161 Diethylaniline, 133

physical properties, 135, 136 1,2-Dihydroxyanthraquinone, see

Alizarin

1,4-Dihydroxyanthraquinone, see Quinizarin

1,5-Dihydroxyanthraquinone, 236,

319

1,8-Dihydroxyanthraquinone, 236

2,3-Dihydroxynaphthalene, 89

1,8-Dihydroxynaphthalene-3,6- disulfonic acid, 212, 264

Dihydroxynaphthalenes, determination, 388

2,8-Dihydroxynaphthalene-6-

sulfonic acid, 204, 208 Dimethoxydibenzanthrone, 8 Dimethylamine, 202 Dimethylaniline, 133 2,4-Dinitroaniline, 102

diazotization, 247 2,4-Dinitroanisole, 98, 116 1,5-Dinitroanthraquinone, 57, 236 1,6-Dinitroanthraquinone, 57 1,7-Dinitroanthraquinone, 57 1,8-Dinitroanthraquinone, 57 m-Dinitrobenzene, 111

purification, 112 toxicity, 112

2,4-Dinitrobenzenesulfonic acid, 85, 103

2,4-Dinitrochlorobenzene, 101, 122,

337 toxicity, 102

Dinitrochlorobenzenesulfonic acid, 122

Dinitrodiphenylamine, 102 o,o'-Dinitrodiphenyldisulfide, 85 1,5-Dinitronaphthalene, 55 1,8-Dinitronaphthalene, 55 2,4-Dinitro-l-naphthol, 151 1,2-Dinitro-4-naphthol-7-sulf onic

acid, 151 Dinitrophenol, 102, 337

Dinitrostilbenedisulfonic acid, 167 Dioxine N, 201

Diphenylamine, 140 technical observations, 142

Diphenylguanidine, 76 Diphenylmethane dyes, 298 Diphenylphthalide, 226 Direct deep black EW, 291 Direct fast violet RR, 278 Disazo dyes, 282

secondary, 277 Distillation

fractional, 24, 64, 341 ff. laboratory, 21-27, 34 with steam, 25

with superheated steam, 141, 142 Distilling off solvents, 21 Dithiosalicylic acid, 330

Dow Chemical Company, 76, 88 Drying, 375

472	SUBJECT INDEX

Drying agents, 22

Drying oven, 373

Eczema, 102

Enamel, 367

Epsilon acid, see 1-Naphthylamine- 3,8-disulfonic acid

Erika red dyes, 335 Eriochrome azurol, 111, 155 Eriochrome black A and T, 202 Eriochrome blue-black R, 202 Eriochrome flavine A, 295 Eriochrome red B, 265 Erioglaucine, 301

Erioviridine B, 301 Ethylberizylaniline, 134 Ethylbenzylanilinesulfonic acid,

136, 305

Ethyl chloride, 148 Eutectic mixture, 91 Evaporation, 22

Evaporators, triple-stage, 372

Factory management, 369 ff. Fast light yellow G, 129, 265 Fastness to light, determination,

411

Fast red 3GL base, 109 Fast red KB base, 164 Fast red R base, 109 Fast scarlet TR base, 164 Fast yellow, 271

Fehling solution, 118 Ferric chloride, 9 Ferric oxide, 75 Filter centrifuge, 18 Filter materials, 19 Filter presses, 348 Filters

fluted, 20 portable, 151

Filtration in the laboratory, 18 Flasks, multiple-necked, 16 Flotation processes, 179 Fluorescence, 47, 48

Fluorination, 67

Formanek absorption tables, 402 Formanilide, 93, 133

Fractional distillation, 24, 64,341ff. Fractional precipitation, 38 Fractionating columns, 24, 342 Fractionating flasks, 23

Freund acid, see 1-Naphthylamine- 3,6-disulfonic acid

Fuchsin fusion, 69

G acid (G-salt), see 2-Naphthol-6,8- disulfonic acid

Gallamide, 170, 308 Gallamine blue, 171, 309 Gallic acid, 170, 308 Gallocyanine, 310

Gamma acid, see 2-Amino-8- naphthol-6-sulfonic acid

Glacial acetic acid, 66, 72 Glass, 366

apparatus, 16 filter cloths, 368 filter funnels, 19

Glucose as reducing agent, 80 Green, dye tables, 399 Griess, Peter, 153

Grinding, 377

Guaiacol, 348

H

H acid, see l-Amino-8-naphthol- 3,6-disulfonic acid

Halogenation, general, 65 Halogen atoms

active, 85, 103 introduction, 9 Halogen carriers, 66

Hansa yellow, 133, 143, 266 Helianthine, 275

Helio Bordeaux BL, 268 Heliogen blue B, 338 Hemp, 368 Hexanitrophenylamine, 102 Houben, 59

SUBJECT INDEX

473

Hydraulic press, 79 Hydrazoanisole, 99 Hydrazobenzene, 124 Hydrazobenzenedisulfonic acid,

123

Hydrocyanocarbodiphenylimide, 325, 326

Hydrogen bromide, 67 2-Hydroxyanthraquinone, 90 Hydroxyl group, introduction, 7 Hydroxynaphthalene, see Naphthol 2-Hydroxy-l-naphthoic acid, 54 2-Hydroxy-3-naphthoic acid, 54,

155

3-Hydroxythionaphthene, 331 Hypochlorite, 9, 145, 167

Ice colors, 109

Indanthrene blue GCD, BCS, 322 Indanthrene blue RS, 321 Indanthrene brilliant blue, 322 Indanthrene brilliant orange GR,

223

Indanthrene golden yellow GK, 60 Indanthrene red 5 GK, 232, 323 Indanthrene scarlet 2G, 223 Indanthrene yellow GK, 232, 322 Indene, 1

Indian yellow, 275 Indigo, 90

Heumann synthesis, 323 Sandmeyer synthesis, 324 Indoxylcarboxylic acid, 324

Intermediates, 2 lodination, 67 Iron, 362

nails, 77, 212

quality for reductions, 75, 77 shavings, 77

Isatin, 328 a-Isatinanilide, 325, 327

Iso-gamma acid (J acid), see 2-Amino-5-naphthol-7- sulfonic acid

J

J acid (iso-gamma acid), see Amino-5-naphthol-7- sulfonic acid

Jute, 368

Kekule, 1

Koch acid, see 1-Naphthylamine- 3.6,8-trisulfonic acid

Kolbe-Schmitt reaction, 154 Kranzlein, Georg, 59

Laboratory notebooks, 14 Laboratory reports, 14 Lake colors, 109

Lake red P, 99 Lauth violet, 314 Lead, 365

hard, 69, 365 homogeneous, 365

Lead dioxide, see Lead peroxide Lead paper, 396

Lead peroxide, 9 Lead peroxide paste

evaluation, 397 preparation, 138

Lead-tin bath metal, 364 Leather, 368

Leuco malachite green, 299 Light fastness

determination, 411 standards, 412

Light green SF (yellowish), 301 Liming, 81, 83

Lithol fast yellow R, 133 Lithol red R, 201 Litmus paper, 395 Lunge nitrometer, 69, 72

M

M acid, see l-Amino-5-naphthol-7- sulfonic acid

Magnesium salts, 58