CA1106843A - Procede d'obtention d'acides n-carboxy-alcane- aminoalcane-diphosphoniques, d'acides n-carboxy- alcane-azocydoalcane-diphosphonique et d'acides n- carboxy-alcane-aminoarylalcane-disphosphoniques - Google Patents

Procede d'obtention d'acides n-carboxy-alcane- aminoalcane-diphosphoniques, d'acides n-carboxy- alcane-azocydoalcane-diphosphonique et d'acides n- carboxy-alcane-aminoarylalcane-disphosphoniques

Info

Publication number: CA1106843A
Authority: CA; Canada
Prior art keywords: acid; carboxy; alkane; diphosphonic; diphosphonic acid
Prior art date: 1977-08-18
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

CA309,547A

Other languages

English (en)

Inventor

Klaus Sommer

Hans-Adolf Rohlfs

Gunter Raab

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.)

BK Giulini Chemie GmbH

Original Assignee

Benckiser Knapsack GmbH

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.)

1977-08-18

Filing date

1978-08-17

Publication date

1981-08-11

1978-08-17 Application filed by Benckiser Knapsack GmbH filed Critical Benckiser Knapsack GmbH

1981-08-11 Application granted granted Critical

1981-08-11 Publication of CA1106843A publication Critical patent/CA1106843A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims description 14
239000002253 acid Substances 0.000 title abstract description 29
150000007513 acids Chemical class 0.000 title abstract description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 17
150000001875 compounds Chemical class 0.000 claims abstract description 7
229910018828 PO3H2 Inorganic materials 0.000 claims abstract description 6
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 3
FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 claims description 8
FRCICXIVPRNPLM-UHFFFAOYSA-N [amino(phosphono)methyl]phosphonic acid Chemical compound OP(=O)(O)C(N)P(O)(O)=O FRCICXIVPRNPLM-UHFFFAOYSA-N 0.000 claims description 7
-1 haloalkane monocarboxylic acid Chemical class 0.000 claims description 7
150000003977 halocarboxylic acids Chemical class 0.000 claims description 7
WTCJJEJMYYASNT-UHFFFAOYSA-N 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid Chemical compound C12=NC(Cl)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1=CC=C(F)C=C1F WTCJJEJMYYASNT-UHFFFAOYSA-N 0.000 claims description 6
QEYMMOKECZBKAC-UHFFFAOYSA-N 3-chloropropanoic acid Chemical compound OC(=O)CCCl QEYMMOKECZBKAC-UHFFFAOYSA-N 0.000 claims description 5
ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 5
NVRVNSHHLPQGCU-UHFFFAOYSA-N 6-bromohexanoic acid Chemical compound OC(=O)CCCCCBr NVRVNSHHLPQGCU-UHFFFAOYSA-N 0.000 claims description 4
229910052783 alkali metal Inorganic materials 0.000 claims description 4
QQWGVQWAEANRTK-UHFFFAOYSA-N bromosuccinic acid Chemical compound OC(=O)CC(Br)C(O)=O QQWGVQWAEANRTK-UHFFFAOYSA-N 0.000 claims description 4
WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 claims description 4
150000008044 alkali metal hydroxides Chemical class 0.000 claims description 3
IJCDULQTWJJMNB-UHFFFAOYSA-N (1-amino-3-hydroxy-1-phosphonopropyl)phosphonic acid Chemical compound OP(=O)(O)C(P(O)(O)=O)(N)CCO IJCDULQTWJJMNB-UHFFFAOYSA-N 0.000 claims description 2
BYOBJKVGOIXVED-UHFFFAOYSA-N (2-phosphonoazepan-2-yl)phosphonic acid Chemical compound OP(O)(=O)C1(P(O)(O)=O)CCCCCN1 BYOBJKVGOIXVED-UHFFFAOYSA-N 0.000 claims description 2
CZHOSQVLPPLTGF-UHFFFAOYSA-N 3-amino-3,3-diphosphonopropanoic acid Chemical compound OP(=O)(O)C(P(O)(O)=O)(N)CC(O)=O CZHOSQVLPPLTGF-UHFFFAOYSA-N 0.000 claims description 2
WNXNUPJZWYOKMW-UHFFFAOYSA-N 5-bromopentanoic acid Chemical compound OC(=O)CCCCBr WNXNUPJZWYOKMW-UHFFFAOYSA-N 0.000 claims description 2
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 2
XZTIUQAKASWQJM-UHFFFAOYSA-N OP(=O)OP(O)=O.NCC1=CC=CC=C1 Chemical compound OP(=O)OP(O)=O.NCC1=CC=CC=C1 XZTIUQAKASWQJM-UHFFFAOYSA-N 0.000 claims description 2
239000012736 aqueous medium Substances 0.000 claims description 2
150000002148 esters Chemical class 0.000 claims description 2
QABLOFMHHSOFRJ-UHFFFAOYSA-N methyl 2-chloroacetate Chemical compound COC(=O)CCl QABLOFMHHSOFRJ-UHFFFAOYSA-N 0.000 claims description 2
229940116254 phosphonic acid Drugs 0.000 claims 4
GPCTYPSWRBUGFH-UHFFFAOYSA-N (1-amino-1-phosphonoethyl)phosphonic acid Chemical compound OP(=O)(O)C(N)(C)P(O)(O)=O GPCTYPSWRBUGFH-UHFFFAOYSA-N 0.000 claims 2
IUDGNRWYNOEIKF-UHFFFAOYSA-N 11-bromo-undecanoic acid Chemical compound OC(=O)CCCCCCCCCCBr IUDGNRWYNOEIKF-UHFFFAOYSA-N 0.000 claims 2
VMBKQCJPBAHOJQ-UHFFFAOYSA-N (1-amino-1-phosphonododecyl)phosphonic acid Chemical compound CCCCCCCCCCCC(N)(P(O)(O)=O)P(O)(O)=O VMBKQCJPBAHOJQ-UHFFFAOYSA-N 0.000 claims 1
PCTMREJZUSEOQD-UHFFFAOYSA-N (1-amino-1-phosphonopropyl)phosphonic acid Chemical compound CCC(N)(P(O)(O)=O)P(O)(O)=O PCTMREJZUSEOQD-UHFFFAOYSA-N 0.000 claims 1
YBJGQSNSAWZZHL-UHFFFAOYSA-N 3-chloro-2,2-dimethylpropanoic acid Chemical compound ClCC(C)(C)C(O)=O YBJGQSNSAWZZHL-UHFFFAOYSA-N 0.000 claims 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims 1
150000001350 alkyl halides Chemical class 0.000 claims 1
XQRLCLUYWUNEEH-UHFFFAOYSA-N diphosphonic acid Chemical compound OP(=O)OP(O)=O XQRLCLUYWUNEEH-UHFFFAOYSA-N 0.000 claims 1
230000003472 neutralizing effect Effects 0.000 claims 1
238000005260 corrosion Methods 0.000 abstract description 2
230000007797 corrosion Effects 0.000 abstract description 2
239000003112 inhibitor Substances 0.000 abstract description 2
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 48
235000011118 potassium hydroxide Nutrition 0.000 description 16
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
238000004458 analytical method Methods 0.000 description 11
238000010992 reflux Methods 0.000 description 11
238000006243 chemical reaction Methods 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
238000003756 stirring Methods 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
238000009835 boiling Methods 0.000 description 5
239000003513 alkali Substances 0.000 description 4
150000001768 cations Chemical class 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
239000000047 product Substances 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
238000001816 cooling Methods 0.000 description 3
238000001035 drying Methods 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
238000006386 neutralization reaction Methods 0.000 description 3
PTMHPRAIXMAOOB-UHFFFAOYSA-N phosphoramidic acid Chemical compound NP(O)(O)=O PTMHPRAIXMAOOB-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 2
230000021523 carboxylation Effects 0.000 description 2
238000006473 carboxylation reaction Methods 0.000 description 2
229910021645 metal ion Inorganic materials 0.000 description 2
239000000203 mixture Substances 0.000 description 2
150000003009 phosphonic acids Chemical class 0.000 description 2
239000000376 reactant Substances 0.000 description 2
235000011121 sodium hydroxide Nutrition 0.000 description 2
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 1
NGWKGSCSHDHHAJ-YPFQVHCOSA-N Liquoric acid Chemical compound C1C[C@H](O)C(C)(C)C2CC[C@@]3(C)[C@]4(C)C[C@H]5O[C@@H]([C@](C6)(C)C(O)=O)C[C@@]5(C)[C@@H]6C4=CC(=O)C3[C@]21C NGWKGSCSHDHHAJ-YPFQVHCOSA-N 0.000 description 1
NFVZIERLAZUYBQ-UHFFFAOYSA-N [K].[Zn] Chemical compound [K].[Zn] NFVZIERLAZUYBQ-UHFFFAOYSA-N 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
ANBBXQWFNXMHLD-UHFFFAOYSA-N aluminum;sodium;oxygen(2-) Chemical compound [O-2].[O-2].[Na+].[Al+3] ANBBXQWFNXMHLD-UHFFFAOYSA-N 0.000 description 1
125000003277 amino group Chemical group 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
125000004432 carbon atom Chemical group C* 0.000 description 1
230000000536 complexating effect Effects 0.000 description 1
239000013078 crystal Substances 0.000 description 1
230000001627 detrimental effect Effects 0.000 description 1
TVQLLNFANZSCGY-UHFFFAOYSA-N disodium;dioxido(oxo)tin Chemical compound [Na+].[Na+].[O-][Sn]([O-])=O TVQLLNFANZSCGY-UHFFFAOYSA-N 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
239000008233 hard water Substances 0.000 description 1
229910001385 heavy metal Inorganic materials 0.000 description 1
238000005342 ion exchange Methods 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
239000002609 medium Substances 0.000 description 1
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
UOURRHZRLGCVDA-UHFFFAOYSA-D pentazinc;dicarbonate;hexahydroxide Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Zn+2].[Zn+2].[Zn+2].[Zn+2].[Zn+2].[O-]C([O-])=O.[O-]C([O-])=O UOURRHZRLGCVDA-UHFFFAOYSA-D 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
150000003141 primary amines Chemical group 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
229910001388 sodium aluminate Inorganic materials 0.000 description 1
229940079864 sodium stannate Drugs 0.000 description 1
HVTHJRMZXBWFNE-UHFFFAOYSA-J sodium zincate Chemical compound [OH-].[OH-].[OH-].[OH-].[Na+].[Na+].[Zn+2] HVTHJRMZXBWFNE-UHFFFAOYSA-J 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000004753 textile Substances 0.000 description 1
238000004809 thin layer chromatography Methods 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)
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F5/00—Softening water; Preventing scale; Adding scale preventatives or scale removers to water, e.g. adding sequestering agents
- C02F5/08—Treatment of water with complexing chemicals or other solubilising agents for softening, scale prevention or scale removal, e.g. adding sequestering agents
- C02F5/10—Treatment of water with complexing chemicals or other solubilising agents for softening, scale prevention or scale removal, e.g. adding sequestering agents using organic substances
- C02F5/14—Treatment of water with complexing chemicals or other solubilising agents for softening, scale prevention or scale removal, e.g. adding sequestering agents using organic substances containing phosphorus
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C5/00—Photographic processes or agents therefor; Regeneration of such processing agents
- G03C5/26—Processes using silver-salt-containing photosensitive materials or agents therefor
- G03C5/29—Development processes or agents therefor
- G03C5/305—Additives other than developers
- G03C5/3053—Tensio-active agents or sequestering agents, e.g. water-softening or wetting agents

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Environmental & Geological Engineering (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Hydrology & Water Resources (AREA)
Engineering & Computer Science (AREA)
Physics & Mathematics (AREA)
Water Supply & Treatment (AREA)
General Physics & Mathematics (AREA)
Health & Medical Sciences (AREA)
Biochemistry (AREA)
General Health & Medical Sciences (AREA)
Molecular Biology (AREA)
Detergent Compositions (AREA)

CA309,547A 1977-08-18 1978-08-17 Procede d'obtention d'acides n-carboxy-alcane- aminoalcane-diphosphoniques, d'acides n-carboxy- alcane-azocydoalcane-diphosphonique et d'acides n- carboxy-alcane-aminoarylalcane-disphosphoniques Expired CA1106843A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DEP2737259.4		1977-08-18
DE19772737259 DE2737259A1 (de)	1977-08-18	1977-08-18	N-carboxyalkan-aminoalkan-diphosphonsaeuren, n-carboxyalkan-azacycloalkan-diphosphonsaeuren und n-carboxyalkan-aminoarylalkan-diphosphonsaeuren sowie verfahren zu ihrer herstellung

Publications (1)

Publication Number	Publication Date
CA1106843A true CA1106843A (fr)	1981-08-11

Family

ID=6016730

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA309,547A Expired CA1106843A (fr)	1977-08-18	1978-08-17	Procede d'obtention d'acides n-carboxy-alcane- aminoalcane-diphosphoniques, d'acides n-carboxy- alcane-azocydoalcane-diphosphonique et d'acides n- carboxy-alcane-aminoarylalcane-disphosphoniques

Country Status (8)

Country	Link
EP (1)	EP0000930B1 (fr)
JP (1)	JPS5470222A (fr)
AT (1)	AT369015B (fr)
CA (1)	CA1106843A (fr)
DE (2)	DE2737259A1 (fr)
DK (1)	DK364478A (fr)
IE (1)	IE47653B1 (fr)
IT (1)	IT1098368B (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3107673A1 (de) *	1981-02-28	1982-09-16	Benckiser-Knapsack Gmbh, 6802 Ladenburg	"verfahren zur herstellung von n-(carboxy-alkyl)-1-amino-alkan-1,1-diphosphonsaeuren und deren alkalisalze"
US4501667A (en) *	1983-03-03	1985-02-26	Ciba-Geigy Corporation	Process of inhibiting corrosion of metal surfaces and/or deposition of scale thereon
IT1215423B (it) *	1987-04-13	1990-02-08	Minnesota Mining & Mfg	Composizioni di sviluppo per materiali fotografici agli alogenuri d'argento.
EP3860956B1 (fr)	2018-10-03	2024-11-27	Italmatch Chemicals S.p.A.	Procédé de fabrication d'acides aminés de n-alkyl-diphosphonate

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NL7404705A (fr) *	1973-04-12	1974-10-15

1977
- 1977-08-18 DE DE19772737259 patent/DE2737259A1/de not_active Withdrawn
1978
- 1978-08-09 IT IT26633/78A patent/IT1098368B/it active
- 1978-08-17 EP EP78100697A patent/EP0000930B1/fr not_active Expired
- 1978-08-17 DE DE7878100697T patent/DE2860812D1/de not_active Expired
- 1978-08-17 DK DK364478A patent/DK364478A/da unknown
- 1978-08-17 JP JP9957578A patent/JPS5470222A/ja active Pending
- 1978-08-17 CA CA309,547A patent/CA1106843A/fr not_active Expired
- 1978-08-18 IE IE1681/78A patent/IE47653B1/en unknown
- 1978-08-18 AT AT0602778A patent/AT369015B/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
EP0000930B1 (fr)	1981-07-01
IE781681L (en)	1979-02-18
EP0000930A1 (fr)	1979-03-07
DE2860812D1 (en)	1981-10-08
DE2737259A1 (de)	1979-03-01
IT7826633A0 (it)	1978-08-09
ATA602778A (de)	1982-04-15
IT1098368B (it)	1985-09-07
AT369015B (de)	1982-11-25
JPS5470222A (en)	1979-06-05
DK364478A (da)	1979-02-19
IE47653B1 (en)	1984-05-16

Legal Events

Date	Code	Title	Description
1998-08-11	MKEX	Expiry

Publication	Publication Date	Title
US2917528A (en)	1959-12-15	Alkanolaminealkanephosphonic acids and salts thereof
US4088678A (en)	1978-05-09	Substituted succinic acid compounds and their use as chelants
KR870001766B1 (ko)	1987-10-06	N, n-디아세트산아미노메틸렌포스폰산의 제조방법
CA1112664A (fr)	1981-11-17	Procede d'obtention de n-carboxyalcanes-aminoalcanes pour les acides polyphosphoniques et leurs sels alcalins
CA1062278A (fr)	1979-09-11	Acides n-phosphonemethylenemonoaminoalcane-mono et polyphosphonique ou n-phosphonemethylenediamicoalcanepolyphosphonique et procede pour leur preparation
FR2567507A1 (fr)	1986-01-17	Methode pour empecher la formation de tartre dans des milieux aqueux
US3833690A (en)	1974-09-03	Ethane diphosphonic acid esters
US4079006A (en)	1978-03-14	Methods of scale inhibition
US3468935A (en)	1969-09-23	Preparation of organophosphonic acids
CA1106843A (fr)	1981-08-11	Procede d'obtention d'acides n-carboxy-alcane- aminoalcane-diphosphoniques, d'acides n-carboxy- alcane-azocydoalcane-diphosphonique et d'acides n- carboxy-alcane-aminoarylalcane-disphosphoniques
US5312973A (en)	1994-05-17	Process for producing n-phosphono-methyl-imino-diacetic acid
US3689544A (en)	1972-09-05	Process for preparing chelating agents
US3988360A (en)	1976-10-26	Process for preparing iminodiacetonitrile
US3032500A (en)	1962-05-01	Sequestration of metal ions
KR20000053014A (ko)	2000-08-25	엔-포스포노메틸 이미노디아세트산의 제조시 모노소듐 이미노디아세트산 용액의 사용
EP0494844B1 (fr)	1995-04-19	Procédé de préparation d'acides diphosphoniques et de leurs sels
US3453301A (en)	1969-07-01	Tris-betahydroxyethyl phosphonomethylene ammonium compounds
US3864378A (en)	1975-02-04	Process for preparing 2-hydroxyethyliminodiacetonitrile
US3567752A (en)	1971-03-02	Substituted hydroxyethylglycine compounds
CA1113475A (fr)	1981-12-01	Procede de fabrication d'acides carboxy-alcane- aminoalcane diphosphoniques et d'acides carboxy- alcane-aminoaryl-alcane diphosphoniques
US2477869A (en)	1949-08-02	Nitro sulfonates from beta-nitro alkanols
US4243591A (en)	1981-01-06	Poly(vinyl phosphonomethylene amino carboxylates) and process for preparation
US3592830A (en)	1971-07-13	Alkylenediamine derivatives containing carbohydrates
US2811550A (en)	1957-10-29	Aliphatic amino polycarboxylic acids and process of producing the same
US2840611A (en)	1958-06-24	Preparation of acrylamide