CA1077518A - Process for producing 1-aminoalkane-1,1-diphosphonic acids - Google Patents
Process for producing 1-aminoalkane-1,1-diphosphonic acidsInfo
- Publication number
- CA1077518A CA1077518A CA278,707A CA278707A CA1077518A CA 1077518 A CA1077518 A CA 1077518A CA 278707 A CA278707 A CA 278707A CA 1077518 A CA1077518 A CA 1077518A
- Authority
- CA
- Canada
- Prior art keywords
- nitrile
- acid
- phosphorous acid
- reaction
- producing
- 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
- 238000000034 method Methods 0.000 title claims abstract description 15
- 239000002253 acid Substances 0.000 title description 12
- 150000007513 acids Chemical class 0.000 title description 7
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 claims abstract description 18
- 150000002825 nitriles Chemical class 0.000 claims abstract description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 7
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 6
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 36
- -1 Lewis acid compound Chemical class 0.000 claims description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- 238000009835 boiling Methods 0.000 claims description 5
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 4
- PQLAYKMGZDUDLQ-UHFFFAOYSA-K aluminium bromide Chemical compound Br[Al](Br)Br PQLAYKMGZDUDLQ-UHFFFAOYSA-K 0.000 claims description 3
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 3
- ZDULHUHNYHJYKA-UHFFFAOYSA-N 2-propan-2-ylsulfonylpropane Chemical compound CC(C)S(=O)(=O)C(C)C ZDULHUHNYHJYKA-UHFFFAOYSA-N 0.000 claims description 2
- 239000002841 Lewis acid Substances 0.000 claims description 2
- 239000000010 aprotic solvent Substances 0.000 claims description 2
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- WKJHMKQSIBMURP-UHFFFAOYSA-N tridecanenitrile Chemical compound CCCCCCCCCCCCC#N WKJHMKQSIBMURP-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 238000001035 drying Methods 0.000 description 7
- 239000000203 mixture Substances 0.000 description 6
- 229910052698 phosphorus Inorganic materials 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 3
- XQRLCLUYWUNEEH-UHFFFAOYSA-N diphosphonic acid Chemical compound OP(=O)OP(O)=O XQRLCLUYWUNEEH-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- ZJIPHXXDPROMEF-UHFFFAOYSA-N dihydroxyphosphanyl dihydrogen phosphite Chemical compound OP(O)OP(O)O ZJIPHXXDPROMEF-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 235000011007 phosphoric acid Nutrition 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- 241001584898 Cerma Species 0.000 description 1
- VXCUURYYWGCLIH-UHFFFAOYSA-N Dodecanenitrile Chemical compound CCCCCCCCCCCC#N VXCUURYYWGCLIH-UHFFFAOYSA-N 0.000 description 1
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical compound Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000009089 cytolysis Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3839—Polyphosphonic acids
- C07F9/3873—Polyphosphonic acids containing nitrogen substituent, e.g. N.....H or N-hydrocarbon group which can be substituted by halogen or nitro(so), N.....O, N.....S, N.....C(=X)- (X =O, S), N.....N, N...C(=X)...N (X =O, S)
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2625767A DE2625767C3 (de) | 1976-06-09 | 1976-06-09 | Verfahren zur Herstellung von 1-Aminoalkan-1,1 -diphosphonsäuren |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1077518A true CA1077518A (en) | 1980-05-13 |
Family
ID=5980129
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA278,707A Expired CA1077518A (en) | 1976-06-09 | 1977-05-18 | Process for producing 1-aminoalkane-1,1-diphosphonic acids |
Country Status (11)
| Country | Link |
|---|---|
| AT (1) | AT348545B (da) |
| BE (1) | BE855548A (da) |
| CA (1) | CA1077518A (da) |
| DE (1) | DE2625767C3 (da) |
| DK (1) | DK143565C (da) |
| FR (1) | FR2354339A1 (da) |
| GB (1) | GB1530856A (da) |
| IT (1) | IT1076181B (da) |
| LU (1) | LU77509A1 (da) |
| NL (1) | NL7706256A (da) |
| SE (1) | SE7706659L (da) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3047107A1 (de) * | 1980-12-13 | 1982-07-29 | Hoechst Ag, 6000 Frankfurt | Verfahren zur hertellung von 1-amino-alkan-1,1-diphosphonsaeuren |
| DE3149454A1 (de) * | 1981-12-14 | 1983-06-23 | Chemische Werke Hüls AG, 4370 Marl | Verfahren zur herstellung von polyacrylnitrilpolyphosphonsaeure und ihre verwendung als flammschutzmittel |
| DE3232753A1 (de) * | 1982-04-19 | 1984-03-08 | Chemische Fabrik Budenheim Rudolf A. Oetker, 6501 Budenheim | Verfahren zur herstellung von 1-aminoalkan-1,1-diphosphonsaeuren |
| DE3214307A1 (de) * | 1982-04-19 | 1983-11-17 | Chemische Fabrik Budenheim Rudolf A. Oetker, 6501 Budenheim | Verfahren zur herstellung von 1-amino-alkan-1,1-diphosphonsaeuren |
| DE3611522A1 (de) * | 1986-04-05 | 1987-10-08 | Henkel Kgaa | Diphosphonylierte oxonitrille, verfahren zu ihrer herstellung und ihre verwendung in mikrobistatischen zusammensetzungen sowie mikrobistatisch wirksame, diphosphonylierte oxonitrile enthaltende zusammensetzungen |
| DE3724653A1 (de) * | 1987-07-25 | 1989-02-02 | Henkel Kgaa | Olefinische diphosphonsaeuren, verfahren zu ihrer herstellung und ihre verwendung als thresholder sowie komplexierend wirkende, olefinische diphosphonsaeuren enthaltende zusammensetzungen |
| DE3724654A1 (de) * | 1987-07-25 | 1989-02-02 | Henkel Kgaa | Hydroxyacetonitrildiphosphonsaeure, verfahren zu ihrer herstellung und ihre verwendung |
| US5043099A (en) * | 1990-07-13 | 1991-08-27 | Kreh Robert P | Mono- and di-substituted (diphosphonoalkylamino methyl)-4-hydroxybenzenesulfonic acid |
| US5221487A (en) * | 1991-10-24 | 1993-06-22 | W. R. Grace & Co.-Conn. | Inhibition of scale formation and corrosion by sulfonated organophosphonates |
-
1976
- 1976-06-09 DE DE2625767A patent/DE2625767C3/de not_active Expired
-
1977
- 1977-02-16 IT IT20348/77A patent/IT1076181B/it active
- 1977-05-18 CA CA278,707A patent/CA1077518A/en not_active Expired
- 1977-05-23 GB GB21603/77A patent/GB1530856A/en not_active Expired
- 1977-06-07 DK DK251577A patent/DK143565C/da active
- 1977-06-07 AT AT402677A patent/AT348545B/de not_active IP Right Cessation
- 1977-06-07 NL NL7706256A patent/NL7706256A/xx not_active Application Discontinuation
- 1977-06-08 SE SE7706659A patent/SE7706659L/xx unknown
- 1977-06-08 FR FR7717529A patent/FR2354339A1/fr not_active Withdrawn
- 1977-06-09 LU LU77509A patent/LU77509A1/xx unknown
- 1977-06-09 BE BE178334A patent/BE855548A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK251577A (da) | 1977-12-10 |
| FR2354339A1 (fr) | 1978-01-06 |
| DE2625767C3 (de) | 1980-06-04 |
| BE855548A (fr) | 1977-10-03 |
| LU77509A1 (da) | 1977-09-19 |
| SE7706659L (sv) | 1977-12-10 |
| DE2625767B2 (de) | 1979-08-23 |
| DK143565B (da) | 1981-09-07 |
| AT348545B (de) | 1979-02-26 |
| DK143565C (da) | 1982-02-01 |
| GB1530856A (en) | 1978-11-01 |
| ATA402677A (de) | 1978-07-15 |
| DE2625767A1 (de) | 1977-12-15 |
| IT1076181B (it) | 1985-04-27 |
| NL7706256A (nl) | 1977-12-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |