DE2521650C3 - - Google Patents
Info
- Publication number
- DE2521650C3 DE2521650C3 DE19752521650 DE2521650A DE2521650C3 DE 2521650 C3 DE2521650 C3 DE 2521650C3 DE 19752521650 DE19752521650 DE 19752521650 DE 2521650 A DE2521650 A DE 2521650A DE 2521650 C3 DE2521650 C3 DE 2521650C3
- Authority
- DE
- Germany
- Prior art keywords
- diazonium
- parts
- water
- sodium sulfate
- diazonium salt
- 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
Links
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 55
- 239000012954 diazonium Substances 0.000 claims description 51
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 29
- 150000001989 diazonium salts Chemical class 0.000 claims description 28
- 229910052938 sodium sulfate Inorganic materials 0.000 claims description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 claims description 20
- 238000002360 preparation method Methods 0.000 claims description 19
- 235000011152 sodium sulphate Nutrition 0.000 claims description 19
- 239000013078 crystal Substances 0.000 claims description 14
- 238000010438 heat treatment Methods 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 13
- 238000001035 drying Methods 0.000 claims description 10
- RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 7
- 238000002156 mixing Methods 0.000 claims description 6
- 238000001556 precipitation Methods 0.000 claims description 5
- 238000006193 diazotization reaction Methods 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 150000004677 hydrates Chemical class 0.000 claims description 3
- 239000000725 suspension Substances 0.000 claims description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 20
- 239000000243 solution Substances 0.000 description 20
- 239000000047 product Substances 0.000 description 17
- 238000012360 testing method Methods 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 239000011780 sodium chloride Substances 0.000 description 10
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 10
- 238000001816 cooling Methods 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 8
- -1 sodium sulphate Diazonium salt Chemical class 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 238000004880 explosion Methods 0.000 description 7
- 238000002425 crystallisation Methods 0.000 description 6
- 230000008025 crystallization Effects 0.000 description 6
- DIZPMCHEQGEION-UHFFFAOYSA-H aluminium sulfate (anhydrous) Chemical compound [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 5
- JQOREDBDOLZSJY-UHFFFAOYSA-H bis(2,2-dioxo-1,3,2,4-dioxathialumetan-4-yl) sulfate hexahydrate Chemical compound O.O.O.O.O.O.[Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O JQOREDBDOLZSJY-UHFFFAOYSA-H 0.000 description 5
- 150000004691 decahydrates Chemical class 0.000 description 5
- 239000002360 explosive Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 235000005074 zinc chloride Nutrition 0.000 description 5
- 239000011592 zinc chloride Substances 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical class [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 230000001133 acceleration Effects 0.000 description 4
- 238000013459 approach Methods 0.000 description 4
- 230000036571 hydration Effects 0.000 description 4
- 238000006703 hydration reaction Methods 0.000 description 4
- 235000010288 sodium nitrite Nutrition 0.000 description 4
- BUADGGPZZZMHBR-UHFFFAOYSA-N 2-methoxy-5-nitrobenzenediazonium Chemical compound COC1=CC=C([N+]([O-])=O)C=C1[N+]#N BUADGGPZZZMHBR-UHFFFAOYSA-N 0.000 description 3
- 229910000831 Steel Inorganic materials 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000012452 mother liquor Substances 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 239000010959 steel Substances 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- CIZVQWNPBGYCGK-UHFFFAOYSA-N benzenediazonium Chemical class N#[N+]C1=CC=CC=C1 CIZVQWNPBGYCGK-UHFFFAOYSA-N 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 229940076230 magnesium sulfate monohydrate Drugs 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- LFCFXZHKDRJMNS-UHFFFAOYSA-L magnesium;sulfate;hydrate Chemical compound O.[Mg+2].[O-]S([O-])(=O)=O LFCFXZHKDRJMNS-UHFFFAOYSA-L 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 229910052573 porcelain Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- NIPDVSLAMPAWTP-UHFFFAOYSA-N 2-methoxy-5-nitroaniline Chemical compound COC1=CC=C([N+]([O-])=O)C=C1N NIPDVSLAMPAWTP-UHFFFAOYSA-N 0.000 description 1
- JRBJSXQPQWSCCF-UHFFFAOYSA-N 3,3'-Dimethoxybenzidine Chemical group C1=C(N)C(OC)=CC(C=2C=C(OC)C(N)=CC=2)=C1 JRBJSXQPQWSCCF-UHFFFAOYSA-N 0.000 description 1
- PBGKNXWGYQPUJK-UHFFFAOYSA-N 4-chloro-2-nitroaniline Chemical compound NC1=CC=C(Cl)C=C1[N+]([O-])=O PBGKNXWGYQPUJK-UHFFFAOYSA-N 0.000 description 1
- PKGYYZYRNOVFKK-UHFFFAOYSA-N 4-chloro-2-nitrobenzenediazonium Chemical compound [O-][N+](=O)C1=CC(Cl)=CC=C1[N+]#N PKGYYZYRNOVFKK-UHFFFAOYSA-N 0.000 description 1
- YPYLIAJGOHBBQK-UHFFFAOYSA-N 4-phenyldiazenylbenzenediazonium Chemical compound C1=CC([N+]#N)=CC=C1N=NC1=CC=CC=C1 YPYLIAJGOHBBQK-UHFFFAOYSA-N 0.000 description 1
- AYWYBCRYWKVVBR-UHFFFAOYSA-N 9,10-dioxoanthracene-1-diazonium Chemical class C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1[N+]#N AYWYBCRYWKVVBR-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical group OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 206010039509 Scab Diseases 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- TYYRFZAVEXQXSN-UHFFFAOYSA-H aluminium sulfate hexadecahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.[Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O TYYRFZAVEXQXSN-UHFFFAOYSA-H 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000001769 aryl amino group Chemical group 0.000 description 1
- 125000005228 aryl sulfonate group Chemical group 0.000 description 1
- 125000005362 aryl sulfone group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- BLUAEPBSVDJDRI-UHFFFAOYSA-H bis(2,2-dioxo-1,3,2,4-dioxathialumetan-4-yl) sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O BLUAEPBSVDJDRI-UHFFFAOYSA-H 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- BUACSMWVFUNQET-UHFFFAOYSA-H dialuminum;trisulfate;hydrate Chemical compound O.[Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O BUACSMWVFUNQET-UHFFFAOYSA-H 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229960003390 magnesium sulfate Drugs 0.000 description 1
- SBSZHUBPJCUAAL-UHFFFAOYSA-L magnesium;sulfate;tetrahydrate Chemical compound O.O.O.O.[Mg+2].[O-]S([O-])(=O)=O SBSZHUBPJCUAAL-UHFFFAOYSA-L 0.000 description 1
- RGNFPYSMVGGFPL-UHFFFAOYSA-N naphthalene-1-diazonium Chemical class C1=CC=C2C([N+]#N)=CC=CC2=C1 RGNFPYSMVGGFPL-UHFFFAOYSA-N 0.000 description 1
- VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910001495 sodium tetrafluoroborate Inorganic materials 0.000 description 1
- KEAYESYHFKHZAL-BJUDXGSMSA-N sodium-22 Chemical compound [22Na] KEAYESYHFKHZAL-BJUDXGSMSA-N 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical class [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- 229960001763 zinc sulfate Drugs 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752521650 DE2521650B2 (de) | 1975-05-15 | 1975-05-15 | Verfahren zur Herstellung trockener Diazoniumsalzpräparate |
| CH594776A CH620198A5 (en) | 1975-05-15 | 1976-05-12 | Process for the safe preparation of diazonium salt products and their precursors |
| IT2322676A IT1060566B (it) | 1975-05-15 | 1976-05-13 | Processo per la produzione sicura di preparati di sali di diazonio e loro precursori |
| JP5446476A JPS51141819A (en) | 1975-05-15 | 1976-05-14 | Modified matter of diazonium salts and safe preparation of its precoursor |
| FR7614764A FR2311000A1 (fr) | 1975-05-15 | 1976-05-17 | Procede de preparation de compositions de sels de diazonium et de leurs precurseurs |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752521650 DE2521650B2 (de) | 1975-05-15 | 1975-05-15 | Verfahren zur Herstellung trockener Diazoniumsalzpräparate |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2521650A1 DE2521650A1 (de) | 1976-12-02 |
| DE2521650B2 DE2521650B2 (de) | 1978-04-27 |
| DE2521650C3 true DE2521650C3 (enrdf_load_stackoverflow) | 1978-12-14 |
Family
ID=5946646
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752521650 Granted DE2521650B2 (de) | 1975-05-15 | 1975-05-15 | Verfahren zur Herstellung trockener Diazoniumsalzpräparate |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS51141819A (enrdf_load_stackoverflow) |
| CH (1) | CH620198A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2521650B2 (enrdf_load_stackoverflow) |
| FR (1) | FR2311000A1 (enrdf_load_stackoverflow) |
| IT (1) | IT1060566B (enrdf_load_stackoverflow) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3317883A1 (de) * | 1983-05-17 | 1984-11-22 | Merck Patent Gmbh, 6100 Darmstadt | Phlegmatisierte formen explosionsgefaehrlicher, organischer diazo-bzw. azidoverbindungen f. strahlungsempfindliche zusammensetzungen |
| EP0158233B1 (de) * | 1984-04-09 | 1989-12-13 | Hoechst Aktiengesellschaft | Verfahren zur Herstellung flüssiger, salzarmer, wässriger Farbstoffzubereitungen |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2062873A (en) * | 1936-12-01 | Unitfd statfs patfnt offitf | ||
| CH193528A (de) * | 1936-03-09 | 1937-10-15 | Chem Ind Basel | Verfahren zur Herstellung einer neuen Diazoniumverbindung. |
-
1975
- 1975-05-15 DE DE19752521650 patent/DE2521650B2/de active Granted
-
1976
- 1976-05-12 CH CH594776A patent/CH620198A5/de not_active IP Right Cessation
- 1976-05-13 IT IT2322676A patent/IT1060566B/it active
- 1976-05-14 JP JP5446476A patent/JPS51141819A/ja active Granted
- 1976-05-17 FR FR7614764A patent/FR2311000A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS51141819A (en) | 1976-12-07 |
| FR2311000A1 (fr) | 1976-12-10 |
| DE2521650A1 (de) | 1976-12-02 |
| FR2311000B1 (enrdf_load_stackoverflow) | 1980-10-24 |
| DE2521650B2 (de) | 1978-04-27 |
| JPS612653B2 (enrdf_load_stackoverflow) | 1986-01-27 |
| IT1060566B (it) | 1982-08-20 |
| CH620198A5 (en) | 1980-11-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) |