CA1043341A - Synthese d'acides pyrrolidone diphosphoniques-5,5 - Google Patents

Synthese d'acides pyrrolidone diphosphoniques-5,5

Info

Publication number: CA1043341A
Authority: CA; Canada
Prior art keywords: pyrrolidone; acid; group; phosphorus; diphosphonic
Prior art date: 1973-08-27
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

Application number

CA290,283A

Other languages

English (en)

Inventor

Walter Ploger

Manfred Schmidt-Dunker

Christian Gloxhuber

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Henkel AG and Co KGaA

Original Assignee

Henkel AG and Co KGaA

Priority date (The priority date 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 date listed.)

1973-08-27

Filing date

1977-11-07

Publication date

1978-11-28

1973-08-27 Priority claimed from DE2343147A external-priority patent/DE2343147C2/de

1977-11-07 Application filed by Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA

1978-11-28 Application granted granted Critical

1978-11-28 Publication of CA1043341A publication Critical patent/CA1043341A/fr

Status Expired legal-status Critical Current

Links

HEJXJRDSBLXLAG-UHFFFAOYSA-N (5-oxo-2-phosphonopyrrolidin-2-yl)phosphonic acid Chemical class OP(O)(=O)C1(P(O)(O)=O)CCC(=O)N1 HEJXJRDSBLXLAG-UHFFFAOYSA-N 0.000 title claims abstract description 14
238000004519 manufacturing process Methods 0.000 title claims description 7
229910052698 phosphorus Inorganic materials 0.000 claims abstract description 22
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims abstract description 21
239000011574 phosphorus Substances 0.000 claims abstract description 21
150000001875 compounds Chemical class 0.000 claims abstract description 20
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 18
239000001257 hydrogen Substances 0.000 claims abstract description 14
150000003839 salts Chemical class 0.000 claims abstract description 14
238000000034 method Methods 0.000 claims abstract description 12
125000000217 alkyl group Chemical group 0.000 claims abstract description 11
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 11
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 10
239000000203 mixture Substances 0.000 claims abstract description 8
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 6
230000007062 hydrolysis Effects 0.000 claims abstract description 5
238000006460 hydrolysis reaction Methods 0.000 claims abstract description 5
235000014786 phosphorus Nutrition 0.000 claims description 19
KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical class OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 8
239000007795 chemical reaction product Substances 0.000 claims description 6
239000000376 reactant Substances 0.000 claims description 4
239000002253 acid Substances 0.000 abstract description 26
229910052602 gypsum Inorganic materials 0.000 abstract description 8
239000010440 gypsum Substances 0.000 abstract description 8
150000007513 acids Chemical class 0.000 abstract description 6
239000003352 sequestering agent Substances 0.000 abstract description 4
229910001420 alkaline earth metal ion Inorganic materials 0.000 abstract description 3
XQRLCLUYWUNEEH-UHFFFAOYSA-N diphosphonic acid Chemical class OP(=O)OP(O)=O XQRLCLUYWUNEEH-UHFFFAOYSA-N 0.000 abstract description 2
239000003381 stabilizer Substances 0.000 abstract 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 31
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 26
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
239000000243 solution Substances 0.000 description 16
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
239000000047 product Substances 0.000 description 8
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
150000001768 cations Chemical class 0.000 description 6
238000001035 drying Methods 0.000 description 6
239000000126 substance Substances 0.000 description 5
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
238000002329 infrared spectrum Methods 0.000 description 4
229910052751 metal Inorganic materials 0.000 description 4
239000002184 metal Substances 0.000 description 4
150000004682 monohydrates Chemical class 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
239000011734 sodium Substances 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 3
150000003863 ammonium salts Chemical class 0.000 description 3
239000002585 base Substances 0.000 description 3
239000011575 calcium Substances 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
239000000463 material Substances 0.000 description 3
229910052700 potassium Inorganic materials 0.000 description 3
239000011591 potassium Substances 0.000 description 3
238000001556 precipitation Methods 0.000 description 3
159000000000 sodium salts Chemical class 0.000 description 3
AFDOVWBBOLLVHJ-UHFFFAOYSA-N (1-ethyl-5-oxo-2-phosphonopyrrolidin-2-yl)phosphonic acid Chemical compound CCN1C(=O)CCC1(P(O)(O)=O)P(O)(O)=O AFDOVWBBOLLVHJ-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
229910052791 calcium Inorganic materials 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
229910003002 lithium salt Inorganic materials 0.000 description 2
239000011777 magnesium Substances 0.000 description 2
150000003009 phosphonic acids Chemical class 0.000 description 2
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
230000009919 sequestration Effects 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
239000001384 succinic acid Substances 0.000 description 2
150000003751 zinc Chemical class 0.000 description 2
IIQMHCALCOZBQF-UHFFFAOYSA-N (1-butyl-5-oxo-2-phosphonopyrrolidin-2-yl)phosphonic acid Chemical compound CCCCN1C(=O)CCC1(P(O)(O)=O)P(O)(O)=O IIQMHCALCOZBQF-UHFFFAOYSA-N 0.000 description 1
PSJKMWOFTYGXGF-UHFFFAOYSA-N (1-methyl-5-oxo-2-phosphonopyrrolidin-2-yl)phosphonic acid Chemical compound CN1C(=O)CCC1(P(O)(O)=O)P(O)(O)=O PSJKMWOFTYGXGF-UHFFFAOYSA-N 0.000 description 1
JLLYLQLDYORLBB-UHFFFAOYSA-N 5-bromo-n-methylthiophene-2-sulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(Br)S1 JLLYLQLDYORLBB-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
229910017974 NH40H Inorganic materials 0.000 description 1
229910020667 PBr3 Inorganic materials 0.000 description 1
ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
-1 alkali metal salts Chemical class 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
239000012670 alkaline solution Substances 0.000 description 1
125000003368 amide group Chemical group 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
238000009835 boiling Methods 0.000 description 1
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
125000005587 carbonate group Chemical group 0.000 description 1
239000000919 ceramic Substances 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
239000003599 detergent Substances 0.000 description 1
150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
159000000002 lithium salts Chemical class 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
159000000003 magnesium salts Chemical class 0.000 description 1
229910021645 metal ion Inorganic materials 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
IPNPIHIZVLFAFP-UHFFFAOYSA-N phosphorus tribromide Chemical compound BrP(Br)Br IPNPIHIZVLFAFP-UHFFFAOYSA-N 0.000 description 1
239000011505 plaster Substances 0.000 description 1
230000002265 prevention Effects 0.000 description 1
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
239000004576 sand Substances 0.000 description 1
RBWSWDPRDBEWCR-RKJRWTFHSA-N sodium;(2r)-2-[(2r)-3,4-dihydroxy-5-oxo-2h-furan-2-yl]-2-hydroxyethanolate Chemical class [Na+].[O-]C[C@@H](O)[C@H]1OC(=O)C(O)=C1O RBWSWDPRDBEWCR-RKJRWTFHSA-N 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

CA290,283A 1973-08-27 1977-11-07 Synthese d'acides pyrrolidone diphosphoniques-5,5 Expired CA1043341A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE2343147A DE2343147C2 (de)	1973-08-27	1973-08-27	Pyrrolidon-5,5-diphosphonsäuren, deren wasserlösliche Salze, und Verfahren zu ihrer Herstellung
CA207,803A CA1027576A (fr)	1973-08-27	1974-08-26	Acides pyrrolidone-5,5-diphosphoniques

Publications (1)

Publication Number	Publication Date
CA1043341A true CA1043341A (fr)	1978-11-28

Family

ID=25667670

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA290,283A Expired CA1043341A (fr)	1973-08-27	1977-11-07	Synthese d'acides pyrrolidone diphosphoniques-5,5

Country Status (1)

Country	Link
CA (1)	CA1043341A (fr)

1977
- 1977-11-07 CA CA290,283A patent/CA1043341A/fr not_active Expired

Publication	Publication Date	Title
US3960888A (en)	1976-06-01	Pyrrolidone-5,5-diphosphonic acids
US4407761A (en)	1983-10-04	Process for the production of ω-amino-1-hydroxyalkylidene-1,1-bisphosphonic acid
KR0137455B1 (ko)	1998-05-01	4-아미노-1-하이드록시부틸리덴-1, 1-비스포스폰산 또는 이의 염의 제조방법
US3941772A (en)	1976-03-02	Azacycloalkane-2,2-diphosphonic acids
US3846420A (en)	1974-11-05	Process for the preparation of 1-aminoalkane-1,-diphosphonic acids and their salts
CA2281922A1 (fr)	1998-09-11	Sel composite d'acide polyphosphorique avec melamine, melam et melem et procede de preparation de celui-ci
GB1436843A (en)	1976-05-26	Preparation of n-phosphonomethyl-glycine
JPS54151955A (en)	1979-11-29	Production of 9-styrylanthracene and relative compounds
US4999437A (en)	1991-03-12	Preparation of ascorbic acid 2-phosphate and of 5, 6-isopropylideneascorbic acid and potassium magnesium l-ascorbate 2-phosphate as an advantageous salt of l-ascorbic acid 2- phosphate
US4034086A (en)	1977-07-05	Pyrrolidone-5,5-diphosphonic acids
US3979385A (en)	1976-09-07	1-Aminoalkane-1,1-diphosphonic acids and their salts
Kaboudin et al.	2003	Microwave-assisted synthesis of α-aminophosphinic acids from hypophosphorus acid salts under solvent free conditions
US3959361A (en)	1976-05-25	Process of producing amino methylene phosphonic acids
CA1043341A (fr)	1978-11-28	Synthese d'acides pyrrolidone diphosphoniques-5,5
US3681416A (en)	1972-08-01	Process for the production of metal chelates
US3452049A (en)	1969-06-24	Mono-magnesium polyamino ethylenediamine tetraacetate:glucono citrate complex
CA2054743C (fr)	2001-11-20	Methode d'obtention de derives de l'acide ascorbique
US4259495A (en)	1981-03-31	Process for producing 2,3,5,6-tetrachloropyridine
US3984543A (en)	1976-10-05	Therapeutic methods employing cyclic aminophosphonic acids
Granoth et al.	1970	Studies in the phenoxaphosphine series
SU790698A1 (ru)	1981-12-30	Способ получени щелочных солей комплексов оксиэтилидендифосфоновой кислоты с металлами п группы
SU539034A1 (ru)	1976-12-15	Способ получени 2,3,5,6,-тетрахлорпиридина
US3870750A (en)	1975-03-11	Process for the production of aminomethane-diphosphonic acid and its salts
PL91814B1 (fr)	1977-03-31
WATANABE et al.	1991	The synthesis and thermal property of sodium diimidotriphosphate