DE2649530C3 - Bis-isothiuronium-Salze, Verfahren zu ihrer Herstellung und Ihre Verwendung zur Reinigung von anionische Farbstoffe und/oder anionische Tenside enthaltenden Abwässern - Google Patents
Bis-isothiuronium-Salze, Verfahren zu ihrer Herstellung und Ihre Verwendung zur Reinigung von anionische Farbstoffe und/oder anionische Tenside enthaltenden AbwässernInfo
- Publication number
- DE2649530C3 DE2649530C3 DE2649530A DE2649530A DE2649530C3 DE 2649530 C3 DE2649530 C3 DE 2649530C3 DE 2649530 A DE2649530 A DE 2649530A DE 2649530 A DE2649530 A DE 2649530A DE 2649530 C3 DE2649530 C3 DE 2649530C3
- Authority
- DE
- Germany
- Prior art keywords
- bis
- isothiuronium salt
- isothiuronium
- anionic
- thiourea
- 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
- 239000000975 dye Substances 0.000 title description 11
- 125000000129 anionic group Chemical group 0.000 title description 6
- 239000002351 wastewater Substances 0.000 title description 6
- 238000004140 cleaning Methods 0.000 title description 5
- 239000003945 anionic surfactant Substances 0.000 title description 4
- 238000000034 method Methods 0.000 title description 2
- 238000004519 manufacturing process Methods 0.000 title 1
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 29
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 239000011541 reaction mixture Substances 0.000 description 15
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 14
- 150000001875 compounds Chemical class 0.000 description 11
- 239000000243 solution Substances 0.000 description 8
- JALHTPIEJQBDEN-UHFFFAOYSA-N 1,5-bis(chloromethyl)-2,4-dimethylbenzene Chemical compound CC1=CC(C)=C(CCl)C=C1CCl JALHTPIEJQBDEN-UHFFFAOYSA-N 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 6
- FULZLIGZKMKICU-UHFFFAOYSA-N N-phenylthiourea Chemical compound NC(=S)NC1=CC=CC=C1 FULZLIGZKMKICU-UHFFFAOYSA-N 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- ZZHIDJWUJRKHGX-UHFFFAOYSA-N 1,4-bis(chloromethyl)benzene Chemical compound ClCC1=CC=C(CCl)C=C1 ZZHIDJWUJRKHGX-UHFFFAOYSA-N 0.000 description 4
- SGRHVVLXEBNBDV-UHFFFAOYSA-N 1,6-dibromohexane Chemical compound BrCCCCCCBr SGRHVVLXEBNBDV-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- LEEHHPPLIOFGSC-UHFFFAOYSA-N cyclohexylthiourea Chemical compound NC(=S)NC1CCCCC1 LEEHHPPLIOFGSC-UHFFFAOYSA-N 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- GTQHJCOHNAFHRE-UHFFFAOYSA-N 1,10-dibromodecane Chemical compound BrCCCCCCCCCCBr GTQHJCOHNAFHRE-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 230000001376 precipitating effect Effects 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000006228 supernatant Substances 0.000 description 3
- ILOBCCAMDOHZGW-UHFFFAOYSA-N 1,2-bis(chloromethyl)naphthalene Chemical compound C1=CC=CC2=C(CCl)C(CCl)=CC=C21 ILOBCCAMDOHZGW-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical group [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- KQJQICVXLJTWQD-UHFFFAOYSA-N N-Methylthiourea Chemical compound CNC(N)=S KQJQICVXLJTWQD-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- -1 aliphatic ketones Chemical class 0.000 description 2
- 150000001449 anionic compounds Chemical class 0.000 description 2
- 229940006460 bromide ion Drugs 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 150000001805 chlorine compounds Chemical group 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000010842 industrial wastewater Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000010865 sewage Substances 0.000 description 2
- 239000010802 sludge Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 150000003585 thioureas Chemical class 0.000 description 2
- FMGGHNGKHRCJLL-UHFFFAOYSA-N 1,2-bis(chloromethyl)benzene Chemical compound ClCC1=CC=CC=C1CCl FMGGHNGKHRCJLL-UHFFFAOYSA-N 0.000 description 1
- XMWGTKZEDLCVIG-UHFFFAOYSA-N 1-(chloromethyl)naphthalene Chemical class C1=CC=C2C(CCl)=CC=CC2=C1 XMWGTKZEDLCVIG-UHFFFAOYSA-N 0.000 description 1
- SGYZXAIDBJJFIC-UHFFFAOYSA-N 1-(dichloromethyl)-2,4-dimethylbenzene Chemical compound CC1=CC=C(C(Cl)Cl)C(C)=C1 SGYZXAIDBJJFIC-UHFFFAOYSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- UOSROERWQJTVNU-UHFFFAOYSA-N 9,10-bis(chloromethyl)anthracene Chemical compound C1=CC=C2C(CCl)=C(C=CC=C3)C3=C(CCl)C2=C1 UOSROERWQJTVNU-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241001465754 Metazoa Species 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
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 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 1
- 238000006065 biodegradation reaction Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- CEZCCHQBSQPRMU-UHFFFAOYSA-L chembl174821 Chemical compound [Na+].[Na+].COC1=CC(S([O-])(=O)=O)=C(C)C=C1N=NC1=C(O)C=CC2=CC(S([O-])(=O)=O)=CC=C12 CEZCCHQBSQPRMU-UHFFFAOYSA-L 0.000 description 1
- 239000000701 coagulant Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 239000000986 disperse dye Substances 0.000 description 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical class CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- XXUJMEYKYHETBZ-UHFFFAOYSA-N ethyl 4-nitrophenyl ethylphosphonate Chemical compound CCOP(=O)(CC)OC1=CC=C([N+]([O-])=O)C=C1 XXUJMEYKYHETBZ-UHFFFAOYSA-N 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical group OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 235000021190 leftovers Nutrition 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000009972 noncorrosive effect Effects 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- DHHGSXPASZBLGC-VPMNAVQSSA-L remazole orange-3R Chemical compound [Na+].[Na+].OC=1C2=CC(NC(=O)C)=CC=C2C=C(S([O-])(=O)=O)C=1\N=N\C1=CC=C(S(=O)(=O)CCOS([O-])(=O)=O)C=C1 DHHGSXPASZBLGC-VPMNAVQSSA-L 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/30—Isothioureas
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/52—Treatment of water, waste water, or sewage by flocculation or precipitation of suspended impurities
- C02F1/5272—Treatment of water, waste water, or sewage by flocculation or precipitation of suspended impurities using specific organic precipitants
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/24—Anthracenes; Hydrogenated anthracenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Hydrology & Water Resources (AREA)
- Engineering & Computer Science (AREA)
- Environmental & Geological Engineering (AREA)
- Water Supply & Treatment (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Removal Of Specific Substances (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT29190/75A IT1054324B (it) | 1975-11-11 | 1975-11-11 | Metodo per la purificazione di acque di scarico contenenti composti organici di carattere anionico mezzi adatti allo scopo e procedimento per la loro preparazione |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2649530A1 DE2649530A1 (de) | 1977-05-18 |
| DE2649530B2 DE2649530B2 (de) | 1978-08-10 |
| DE2649530C3 true DE2649530C3 (de) | 1979-04-12 |
Family
ID=11226522
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2649530A Expired DE2649530C3 (de) | 1975-11-11 | 1976-10-29 | Bis-isothiuronium-Salze, Verfahren zu ihrer Herstellung und Ihre Verwendung zur Reinigung von anionische Farbstoffe und/oder anionische Tenside enthaltenden Abwässern |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS5277015A (enExample) |
| AT (1) | AT344725B (enExample) |
| BE (1) | BE848215A (enExample) |
| CH (1) | CH627448A5 (enExample) |
| DE (1) | DE2649530C3 (enExample) |
| FR (1) | FR2331555A1 (enExample) |
| GB (1) | GB1545077A (enExample) |
| IT (1) | IT1054324B (enExample) |
| NL (1) | NL7612500A (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5764662A (en) * | 1980-10-04 | 1982-04-19 | Otsuka Pharmaceut Co Ltd | Alkylene disulfur derivative |
| FR2840908B1 (fr) * | 2002-06-12 | 2005-02-18 | Michelin Soc Tech | Composition de caoutchouc comprenant un sel de thiouronium, son procede de preparation, pneumatique a base d'une telle composition et utilisation a titre d'agent anti-reversion d'un sel de thiouronium |
-
1975
- 1975-11-11 IT IT29190/75A patent/IT1054324B/it active
-
1976
- 1976-10-29 DE DE2649530A patent/DE2649530C3/de not_active Expired
- 1976-11-05 JP JP51132509A patent/JPS5277015A/ja active Pending
- 1976-11-09 FR FR7633784A patent/FR2331555A1/fr active Granted
- 1976-11-10 NL NL7612500A patent/NL7612500A/xx not_active Application Discontinuation
- 1976-11-10 AT AT834276A patent/AT344725B/de not_active IP Right Cessation
- 1976-11-10 BE BE172260A patent/BE848215A/xx unknown
- 1976-11-10 GB GB46854/76A patent/GB1545077A/en not_active Expired
- 1976-11-10 CH CH1417976A patent/CH627448A5/it not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CH627448A5 (en) | 1982-01-15 |
| BE848215A (fr) | 1977-05-10 |
| NL7612500A (nl) | 1977-05-13 |
| ATA834276A (de) | 1977-12-15 |
| GB1545077A (en) | 1979-05-02 |
| DE2649530A1 (de) | 1977-05-18 |
| JPS5277015A (en) | 1977-06-29 |
| FR2331555A1 (fr) | 1977-06-10 |
| FR2331555B1 (enExample) | 1979-03-02 |
| IT1054324B (it) | 1981-11-10 |
| AT344725B (de) | 1978-08-10 |
| DE2649530B2 (de) | 1978-08-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE3048283C2 (de) | Verfahren zur Herstellung von Hydroxyalkylaminosulfonsäuren | |
| DE2649530C3 (de) | Bis-isothiuronium-Salze, Verfahren zu ihrer Herstellung und Ihre Verwendung zur Reinigung von anionische Farbstoffe und/oder anionische Tenside enthaltenden Abwässern | |
| DE69013061T2 (de) | Verfahren zur Herstellung von Kohlensäureestern. | |
| DE2707764C2 (de) | Bis- und Trisguanylhydrazoniumsalze, Verfahren zu ihrer Herstellung und ihre Verwendung zur Abwasserreinigung | |
| DE2425923C3 (de) | Verfahren zur Abtrennung von Kaliumkationen von Natriumkationen | |
| DE1445470A1 (de) | Verfahren zur Herstellung von heterocyclischen organischen Verbindungen | |
| EP0163233A2 (de) | Quartäre Ammoniumsalze sulfonierter Triarylphosphine | |
| DE767071C (de) | Verfahren zur Herstellung von Kondensationserzeugnissen | |
| DE2831118A1 (de) | Verfahren zur herstellung von p-hydroxyphenylglycin und seiner n-alkyl- und n,n-dialkylderivate | |
| DE833959C (de) | Verfahren zur Herstellung von chemotherapeutisch wertvollen Biguanidderivaten | |
| DE1695892A1 (de) | Neue Pyridinderivate und Verfahren zu ihrer Herstellung | |
| DE88557C (enExample) | ||
| AT360446B (de) | Verfahren zur reinigung von abwaessern | |
| DE2538541A1 (de) | Verfahren zur herstellung von ammonium-p-styrolsulfonat | |
| AT353712B (de) | Reinigung von anionische organische ver- bindungen enthaltenden abwaessern | |
| DE572723C (de) | Verfahren zur Darstellung von Chlor- und Bromderivaten der 2-Aminonaphthalin-1-sulfonsaeure | |
| DE68903049T2 (de) | Verfahren zur rueckgewinnung von gallium. | |
| DE924513C (de) | Verfahren zur Herstellung von Biguanidderivaten | |
| DE930209C (de) | Verfahren zur Herstellung von N-Aryl-azo-sultamen | |
| DE91721C (enExample) | ||
| DE1518880A1 (de) | Verfahren zur Anreicherung von Sulfonaten | |
| DE657118C (de) | Verfahren zur Darstellung von Abkoemmlingen des p-Phenanthrolins | |
| DE690895C (de) | Verfahren zur Herstellung von sulfonierten Phenolaethern | |
| DE2628042B2 (de) | 3-Amino-tricyclo [53.1.0.3A1 -undecan, dessen Säureadditionssalze und Verfahren zur Herstellung dieser Verbindungen | |
| DE2201162C3 (de) | Auraminfarbstoff, Verfahren zu seiner Herstellung und dessen Verwendung |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |