CA2085144A1 - Method for processing waste waters containing organic phosphorus compounds, in particular sulfonted arylphosphines - Google Patents
Method for processing waste waters containing organic phosphorus compounds, in particular sulfonted arylphosphinesInfo
- Publication number
- CA2085144A1 CA2085144A1 CA002085144A CA2085144A CA2085144A1 CA 2085144 A1 CA2085144 A1 CA 2085144A1 CA 002085144 A CA002085144 A CA 002085144A CA 2085144 A CA2085144 A CA 2085144A CA 2085144 A1 CA2085144 A1 CA 2085144A1
- Authority
- CA
- Canada
- Prior art keywords
- amine
- water
- waste waters
- organic
- dissolved
- 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.)
- Abandoned
Links
- 239000002351 wastewater Substances 0.000 title claims abstract description 38
- 150000002903 organophosphorus compounds Chemical class 0.000 title claims abstract description 8
- 238000000034 method Methods 0.000 title claims description 31
- 238000012545 processing Methods 0.000 title claims description 7
- 150000001412 amines Chemical class 0.000 claims abstract description 40
- 239000000356 contaminant Substances 0.000 claims abstract description 15
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- 150000007522 mineralic acids Chemical class 0.000 claims abstract description 8
- -1 hydrogen ions Chemical class 0.000 claims description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- 238000000605 extraction Methods 0.000 claims description 9
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 7
- 239000008346 aqueous phase Substances 0.000 claims description 6
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 5
- 239000012074 organic phase Substances 0.000 claims description 5
- YKGBNAGNNUEZQC-UHFFFAOYSA-N 6-methyl-n,n-bis(6-methylheptyl)heptan-1-amine Chemical compound CC(C)CCCCCN(CCCCCC(C)C)CCCCCC(C)C YKGBNAGNNUEZQC-UHFFFAOYSA-N 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 238000000926 separation method Methods 0.000 claims description 4
- 125000002015 acyclic group Chemical group 0.000 claims description 3
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims description 3
- 150000008041 alkali metal carbonates Chemical class 0.000 claims description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims 1
- 150000007942 carboxylates Chemical group 0.000 claims 1
- 150000005619 secondary aliphatic amines Chemical class 0.000 claims 1
- 150000003510 tertiary aliphatic amines Chemical class 0.000 claims 1
- 239000000243 solution Substances 0.000 description 16
- 239000002253 acid Substances 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000012071 phase Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 238000006277 sulfonation reaction Methods 0.000 description 5
- 238000010494 dissociation reaction Methods 0.000 description 4
- 230000005593 dissociations Effects 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 150000003018 phosphorus compounds Chemical class 0.000 description 3
- MYAJTCUQMQREFZ-UHFFFAOYSA-K tppts Chemical compound [Na+].[Na+].[Na+].[O-]S(=O)(=O)C1=CC=CC(P(C=2C=C(C=CC=2)S([O-])(=O)=O)C=2C=C(C=CC=2)S([O-])(=O)=O)=C1 MYAJTCUQMQREFZ-UHFFFAOYSA-K 0.000 description 3
- 239000002699 waste material Substances 0.000 description 3
- NGKIIKNJVVBNNE-UHFFFAOYSA-N 11-methyldodecan-1-amine Chemical compound CC(C)CCCCCCCCCCN NGKIIKNJVVBNNE-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 150000004679 hydroxides Chemical class 0.000 description 2
- 238000009434 installation Methods 0.000 description 2
- XTAZYLNFDRKIHJ-UHFFFAOYSA-N n,n-dioctyloctan-1-amine Chemical compound CCCCCCCCN(CCCCCCCC)CCCCCCCC XTAZYLNFDRKIHJ-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 150000003003 phosphines Chemical class 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- KMUONIBRACKNSN-UHFFFAOYSA-N potassium dichromate Chemical compound [K+].[K+].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O KMUONIBRACKNSN-UHFFFAOYSA-N 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- WSANLGASBHUYGD-UHFFFAOYSA-N sulfidophosphanium Chemical class S=[PH3] WSANLGASBHUYGD-UHFFFAOYSA-N 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- HNJDTFYDPQQFPN-UHFFFAOYSA-N 3-[phenyl-(3-sulfophenyl)phosphinothioyl]benzenesulfonic acid Chemical compound OS(=O)(=O)c1cccc(c1)P(=S)(c1ccccc1)c1cccc(c1)S(O)(=O)=O HNJDTFYDPQQFPN-UHFFFAOYSA-N 0.000 description 1
- UNCGIYQODVQKIT-UHFFFAOYSA-N 3-[phenyl-(3-sulfophenyl)phosphoryl]benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC(P(=O)(C=2C=CC=CC=2)C=2C=C(C=CC=2)S(O)(=O)=O)=C1 UNCGIYQODVQKIT-UHFFFAOYSA-N 0.000 description 1
- ZBMZOFSLQIPSPW-UHFFFAOYSA-N 3-bis(3-sulfophenyl)phosphanylbenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC(P(C=2C=C(C=CC=2)S(O)(=O)=O)C=2C=C(C=CC=2)S(O)(=O)=O)=C1 ZBMZOFSLQIPSPW-UHFFFAOYSA-N 0.000 description 1
- OVMZAPIQTPIOAI-UHFFFAOYSA-N 3-bis(3-sulfophenyl)phosphinothioylbenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC(P(=S)(C=2C=C(C=CC=2)S(O)(=O)=O)C=2C=C(C=CC=2)S(O)(=O)=O)=C1 OVMZAPIQTPIOAI-UHFFFAOYSA-N 0.000 description 1
- QUKFQRAUORIVKQ-UHFFFAOYSA-N 3-bis(3-sulfophenyl)phosphorylbenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC(P(=O)(C=2C=C(C=CC=2)S(O)(=O)=O)C=2C=C(C=CC=2)S(O)(=O)=O)=C1 QUKFQRAUORIVKQ-UHFFFAOYSA-N 0.000 description 1
- YGLJGOMFUHQSBN-UHFFFAOYSA-N 7-methyl-n,n-bis(7-methyloctyl)octan-1-amine Chemical compound CC(C)CCCCCCN(CCCCCCC(C)C)CCCCCCC(C)C YGLJGOMFUHQSBN-UHFFFAOYSA-N 0.000 description 1
- SAIKULLUBZKPDA-UHFFFAOYSA-N Bis(2-ethylhexyl) amine Chemical compound CCCCC(CC)CNCC(CC)CCCC SAIKULLUBZKPDA-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 239000004135 Bone phosphate Substances 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 238000006887 Ullmann reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000005210 alkyl ammonium group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- NAPSCFZYZVSQHF-UHFFFAOYSA-N dimantine Chemical compound CCCCCCCCCCCCCCCCCCN(C)C NAPSCFZYZVSQHF-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- DIAIBWNEUYXDNL-UHFFFAOYSA-N n,n-dihexylhexan-1-amine Chemical compound CCCCCCN(CCCCCC)CCCCCC DIAIBWNEUYXDNL-UHFFFAOYSA-N 0.000 description 1
- NHLUVTZJQOJKCC-UHFFFAOYSA-N n,n-dimethylhexadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCN(C)C NHLUVTZJQOJKCC-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000012476 oxidizable substance Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- RPGWZZNNEUHDAQ-UHFFFAOYSA-N phenylphosphine Chemical compound PC1=CC=CC=C1 RPGWZZNNEUHDAQ-UHFFFAOYSA-N 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 150000007519 polyprotic acids Polymers 0.000 description 1
- 238000011403 purification operation Methods 0.000 description 1
- 238000011946 reduction process Methods 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- 238000012958 reprocessing Methods 0.000 description 1
- 150000003284 rhodium compounds Chemical class 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- AXORVIZLPOGIRG-UHFFFAOYSA-N β-methylphenethylamine Chemical compound NCC(C)C1=CC=CC=C1 AXORVIZLPOGIRG-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C02F1/26—Treatment of water, waste water, or sewage by extraction
-
- 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
- C02F1/58—Treatment of water, waste water, or sewage by removing specified dissolved compounds
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Hydrology & Water Resources (AREA)
- Engineering & Computer Science (AREA)
- Environmental & Geological Engineering (AREA)
- Water Supply & Treatment (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Removal Of Specific Substances (AREA)
- Physical Water Treatments (AREA)
- Extraction Or Liquid Replacement (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP4141772.0 | 1991-12-18 | ||
| DE4141772A DE4141772A1 (de) | 1991-12-18 | 1991-12-18 | Verfahren zur aufarbeitung organischer phosphorverbindungen, insbesondere sulfonierte arylphosphine enthaltender abwaesser |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2085144A1 true CA2085144A1 (en) | 1993-06-19 |
Family
ID=6447361
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002085144A Abandoned CA2085144A1 (en) | 1991-12-18 | 1992-12-11 | Method for processing waste waters containing organic phosphorus compounds, in particular sulfonted arylphosphines |
Country Status (11)
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4140062A1 (de) * | 1991-12-05 | 1993-06-09 | Hoechst Ag, 6230 Frankfurt, De | Verfahren zur aufarbeitung rhodiumverbindungen, derivate organischer phosphine und weitere verunreinigungen geloest enthaltender abwaesser |
| DE19732074A1 (de) * | 1997-07-25 | 1999-01-28 | Bayer Ag | Verfahren zur Reinigung von organischen und gegebenenfalls anorganischen Schwefelverbindungen enthaltenden Abwässern |
| EP2591268A1 (en) | 2010-07-09 | 2013-05-15 | Dresser Wayne AB | Fuel dispensing unit comprising a locking member for retaining a fuel conduit in a locked position |
| US10578230B2 (en) | 2010-07-09 | 2020-03-03 | Wayne Fueling Systems Sweden Ab | Fuel dispensing unit comprising a locking member for retaining a fuel conduit in a locked position |
| CN103011326B (zh) * | 2012-12-14 | 2017-10-24 | 中国环境科学研究院 | 一种减少金刚烷胺生产废水中有机物的方法 |
| CN102963948A (zh) * | 2012-12-14 | 2013-03-13 | 中国环境科学研究院 | 一种萃取法处理金刚烷胺化废水的方法 |
| KR20170009797A (ko) * | 2015-07-17 | 2017-01-25 | 릴라이언스 인더스트리즈 리미티드 | 폐수로부터 오염물질을 분리하기 위한 방법 및 그 시스템 |
| KR102702919B1 (ko) * | 2020-10-28 | 2024-09-03 | 한화솔루션 주식회사 | 설폰화 아릴 포스핀의 제조방법 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS55109213A (en) * | 1979-02-10 | 1980-08-22 | Nippon Soretsukusu Kk | Recovering phosphate ion |
| CH663781A5 (de) * | 1985-07-05 | 1988-01-15 | Ciba Geigy Ag | Verfahren zur reinigung von abwaessern. |
| DE3718725A1 (de) * | 1987-06-04 | 1988-12-22 | Hoechst Ag | Verfahren zur abtrennung von halogenierten hydroxy-aromaten aus waessrigen loesungen |
| DE68904070T2 (de) * | 1989-05-09 | 1993-04-29 | Bayer Antwerpen Nv | Verfahren zur entfernung von nitrat und organischen verunreinigungen aus abwaessern. |
-
1991
- 1991-12-18 DE DE4141772A patent/DE4141772A1/de not_active Withdrawn
-
1992
- 1992-10-30 TW TW081108644A patent/TW210325B/zh active
- 1992-11-30 KR KR1019920022913A patent/KR930012594A/ko not_active Ceased
- 1992-12-09 EP EP92120951A patent/EP0547487A1/de not_active Withdrawn
- 1992-12-11 ZA ZA929646A patent/ZA929646B/xx unknown
- 1992-12-11 MX MX9207179A patent/MX9207179A/es unknown
- 1992-12-11 CA CA002085144A patent/CA2085144A1/en not_active Abandoned
- 1992-12-11 JP JP4332012A patent/JPH05317848A/ja active Pending
- 1992-12-16 AU AU30291/92A patent/AU3029192A/en not_active Abandoned
- 1992-12-16 BR BR9205030A patent/BR9205030A/pt unknown
- 1992-12-17 CN CN92114473A patent/CN1073665A/zh active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| CN1073665A (zh) | 1993-06-30 |
| AU3029192A (en) | 1993-06-24 |
| EP0547487A1 (de) | 1993-06-23 |
| MX9207179A (es) | 1993-06-01 |
| ZA929646B (en) | 1993-06-09 |
| DE4141772A1 (de) | 1993-06-24 |
| TW210325B (enrdf_load_html_response) | 1993-08-01 |
| KR930012594A (ko) | 1993-07-20 |
| BR9205030A (pt) | 1993-06-22 |
| JPH05317848A (ja) | 1993-12-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Dead |