US2092359A - Solid diazo salts - Google Patents
Solid diazo salts Download PDFInfo
- Publication number
- US2092359A US2092359A US113082A US11308236A US2092359A US 2092359 A US2092359 A US 2092359A US 113082 A US113082 A US 113082A US 11308236 A US11308236 A US 11308236A US 2092359 A US2092359 A US 2092359A
- Authority
- US
- United States
- Prior art keywords
- diazo
- salts
- solid
- parts
- stands
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title description 9
- 239000007787 solid Substances 0.000 title description 7
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 9
- 150000003839 salts Chemical class 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 229910052718 tin Inorganic materials 0.000 description 5
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical class NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 229910052793 cadmium Inorganic materials 0.000 description 4
- YKYOUMDCQGMQQO-UHFFFAOYSA-L cadmium dichloride Chemical compound Cl[Cd]Cl YKYOUMDCQGMQQO-UHFFFAOYSA-L 0.000 description 4
- 239000012954 diazonium Substances 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 239000011592 zinc chloride Substances 0.000 description 4
- 235000005074 zinc chloride Nutrition 0.000 description 4
- 229960001939 zinc chloride Drugs 0.000 description 4
- 150000008049 diazo compounds Chemical class 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000006193 diazotization reaction Methods 0.000 description 2
- LZDSILRDTDCIQT-UHFFFAOYSA-N dinitrogen trioxide Chemical compound [O-][N+](=O)N=O LZDSILRDTDCIQT-UHFFFAOYSA-N 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 2
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical class NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- RCANFVUNFLBTJG-UHFFFAOYSA-N 2-bromo-6-chlorobenzene-1,4-diamine Chemical compound NC1=CC(Cl)=C(N)C(Br)=C1 RCANFVUNFLBTJG-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- CZLRHMPTJLCJKQ-UHFFFAOYSA-N ac1n60v3 Chemical class N[N+]#N CZLRHMPTJLCJKQ-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- DIZPMCHEQGEION-UHFFFAOYSA-H aluminium sulfate (anhydrous) Chemical class [Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O DIZPMCHEQGEION-UHFFFAOYSA-H 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- -1 for instance Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- ZTQDYDIRBKMMQB-UHFFFAOYSA-N n-(4-aminophenyl)nitramide Chemical compound NC1=CC=C(N[N+]([O-])=O)C=C1 ZTQDYDIRBKMMQB-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/06—Zinc compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/08—Cadmium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/22—Tin compounds
Definitions
- Y stands for halogen
- Me stands for a metal of the group consisting of Zn, Cd and Sn
- the diazo salts may be obtained by diazotizing unilaterally 1,4-diaminobenzenes, halogenated in the nucleus and being free. from sulfonic acid or carboxylic acid groups, 1. e. by treating the said 1,4-diaminobenzenes with thequantity of mineral acid and nitrous acid, necessary for diazotizing one amino group, and by precipitating the diazo compounds, thus obtained, in the form of stabilized diazo compounds, such as, for instance, zinc chloride-, tin chlorideor cadmium chloride-double salts.
- stabilized diazo compounds such as, for instance, zinc chloride-, tin chlorideor cadmium chloride-double salts.
- diaminobenzenes could be transformed in a smooth reaction into aminodiazonium salts in the presence of mineral acid and it could, fur thermore, not be foreseen whether these monodiazo compounds could easily be precipitated and whether they would be stable enough for being used on an industrial scale as dyeing salts.
- Heep-NP Z1101, 1 2 Q is salted out by addition of sodium chloride, worked up as usual and, if desired, adjusted to the usual commercial form by addition of, for instance, anhydrous sodium sulfate or partly dehydrated aluminium sulfate.
- the salt is very stable and easily soluble.
- the precipitation may also be effected by means of a zinc chloride solution which has a small content of SnCLi.
- diazonium zinc chloride double salts of other halogen-lA-diaminobenzenes for instance, of 2-ch1oro-, 2-ch1oro-5-methy1- and 2- chloro-fi-bromo-lA-diaminobenzene.
- Y stands for halogen
- Z stands for one of the group consisting of hydrogen, halogen and alkyl
- Me stands for a metal of the; group consisting of Zn, Cd and Sn, and m for a num- 25 her corresponding to the highest valence of the metal signified by Me, being very stable and easily soluble in water.
- Y stands for halogen
- Z stands for one wherein Me stands for a metal of the group consisting of Zn, Cd and Sn, and m for a number. corresponding to the highest valence of the metal signinfied by Me, being very stable and easily soluble in water.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL35261D NL35261C (fr) | 1932-05-21 | ||
| DEI44494D DE586355C (de) | 1932-05-21 | 1932-05-22 | Verfahren zur Herstellung von Diazoverbindungen in fester Form |
| US671590A US2067132A (en) | 1932-05-21 | 1933-05-17 | Solid diazo salts |
| GB14808/33A GB403013A (en) | 1932-05-21 | 1933-05-22 | Manufacture of solid diazo-salts |
| FR755889D FR755889A (fr) | 1932-05-21 | 1933-05-22 | Nouveaux sels diazoïques solides et leur procédé de préparation |
| US113082A US2092359A (en) | 1932-05-21 | 1936-11-27 | Solid diazo salts |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE403013X | 1932-05-21 | ||
| US671590A US2067132A (en) | 1932-05-21 | 1933-05-17 | Solid diazo salts |
| US113082A US2092359A (en) | 1932-05-21 | 1936-11-27 | Solid diazo salts |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2092359A true US2092359A (en) | 1937-09-07 |
Family
ID=31998324
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US113082A Expired - Lifetime US2092359A (en) | 1932-05-21 | 1936-11-27 | Solid diazo salts |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US2092359A (fr) |
| FR (1) | FR755889A (fr) |
| GB (1) | GB403013A (fr) |
| NL (1) | NL35261C (fr) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3300471A (en) * | 1964-01-02 | 1967-01-24 | Universal Oil Prod Co | p-(nu-cyanoalkyl-nu-hydrocarbylamino)-benzenediazonium chlorides |
-
0
- NL NL35261D patent/NL35261C/xx active
-
1933
- 1933-05-22 FR FR755889D patent/FR755889A/fr not_active Expired
- 1933-05-22 GB GB14808/33A patent/GB403013A/en not_active Expired
-
1936
- 1936-11-27 US US113082A patent/US2092359A/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3300471A (en) * | 1964-01-02 | 1967-01-24 | Universal Oil Prod Co | p-(nu-cyanoalkyl-nu-hydrocarbylamino)-benzenediazonium chlorides |
Also Published As
| Publication number | Publication date |
|---|---|
| FR755889A (fr) | 1933-12-01 |
| NL35261C (fr) | |
| GB403013A (en) | 1933-12-14 |
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