GB1230121A - - Google Patents
Info
- Publication number
- GB1230121A GB1230121A GB1230121DA GB1230121A GB 1230121 A GB1230121 A GB 1230121A GB 1230121D A GB1230121D A GB 1230121DA GB 1230121 A GB1230121 A GB 1230121A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkylene
- formaldehyde
- aldehyde
- group
- preferred
- 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
- 150000001299 aldehydes Chemical class 0.000 abstract 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 3
- 125000002947 alkylene group Chemical group 0.000 abstract 3
- -1 methylene phosphonic acids Chemical class 0.000 abstract 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 abstract 2
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 2
- 150000002576 ketones Chemical class 0.000 abstract 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 abstract 2
- 229910052698 phosphorus Inorganic materials 0.000 abstract 2
- 239000011574 phosphorus Substances 0.000 abstract 2
- 229920000768 polyamine Polymers 0.000 abstract 2
- 238000002360 preparation method Methods 0.000 abstract 2
- 239000000376 reactant Substances 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 abstract 1
- YTGSYRVSBPFKMQ-UHFFFAOYSA-N 2,2,2-tribromoacetaldehyde Chemical compound BrC(Br)(Br)C=O YTGSYRVSBPFKMQ-UHFFFAOYSA-N 0.000 abstract 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 abstract 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 abstract 1
- SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 abstract 1
- 229930040373 Paraformaldehyde Natural products 0.000 abstract 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 abstract 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000005263 alkylenediamine group Chemical group 0.000 abstract 1
- 150000003863 ammonium salts Chemical class 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 150000004985 diamines Chemical class 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- NFDRPXJGHKJRLJ-UHFFFAOYSA-N edtmp Chemical compound OP(O)(=O)CN(CP(O)(O)=O)CCN(CP(O)(O)=O)CP(O)(O)=O NFDRPXJGHKJRLJ-UHFFFAOYSA-N 0.000 abstract 1
- 239000003995 emulsifying agent Substances 0.000 abstract 1
- OUDSFQBUEBFSPS-UHFFFAOYSA-N ethylenediaminetriacetic acid Chemical compound OC(=O)CNCCN(CC(O)=O)CC(O)=O OUDSFQBUEBFSPS-UHFFFAOYSA-N 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 238000006386 neutralization reaction Methods 0.000 abstract 1
- 229920002866 paraformaldehyde Polymers 0.000 abstract 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 abstract 1
- 229920001281 polyalkylene Polymers 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- HFFLGKNGCAIQMO-UHFFFAOYSA-N trichloroacetaldehyde Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-UHFFFAOYSA-N 0.000 abstract 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
- C07F9/3808—Acyclic saturated acids which can have further substituents on alkyl
- C07F9/3817—Acids containing the structure (RX)2P(=X)-alk-N...P (X = O, S, Se)
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
Abstract
1,230,121. Preparation of polyamino methylene phosphonic acids. ALBRIGHT & WILSON (MFG) Ltd. 26 April, 1968 [27 Jan., 1967], No. 20017/68. Divided out of 1,142,294. Addition to 1,142,294. Heading C2C. Alkylene polyamino methylene phosphonic acids of the formula (where R is an alkylene group, R<SP>1</SP> is hydrogen, a hydrocarbyl or substituted hydrocarbyl group, R<SP>11</SP> is hydrogen, a substituted or unsubstituted alkyl group of from 1 to 20 carbon atoms or a phosphomethylene group and n is an integer from 1 to 5) are prepared by reacting together (1) an alkylene polyamine of the formula- R<SP>11</SP>[R<SP>11</SP>NR] n NR<SP>11</SP>H or a hydrate or salt thereof, (2) an aldehyde or ketone R<SP>1</SP>R<SP>1</SP>CO and (3) a phosphorus trihalide, in the presence of more than two moles of water per mole of phosphorus trihalide. The preferred reactants are phosphorus trichloride, formaldehyde and ethylene diamine. However, other alkylene diamines or polyalkylene diamines may be used e.g. diethylene, triamine and hexamethylene diamine, and also substituted polyamines e.g. ethylene diaminetriacetic acid. Specified aldehydes and ketones are formaldehyde, acetaldehyde, chloral, bromal, glutaraldehyde and acetone. Formaldehyde, which is the preferred aldehyde, may be used in the form of trioxane or paraformaldehyde or in the form of its concentrated aqueous solution containing 37% by weight of the aldehyde. The reaction is normally carried out at 30‹ to 60‹ C. and is desirably completed by heating at 100‹ to 120‹ C. for a short time. During the reaction a pH of not more than 2À0 is preferred. If the reactants are not water soluble, a water-miscible organic diluent or an emulsifying agent may be used. The phosphonic acid products may be obtained in the form of metal or ammonium salts by appropriate neutralization of the free acid. Examples describe the preparation of ethylenediamine tetrakis (methylene phosphonic acid).
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2001768 | 1967-01-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1230121A true GB1230121A (en) | 1971-04-28 |
Family
ID=10138971
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1230121D Expired GB1230121A (en) | 1967-01-27 | 1967-01-27 |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1230121A (en) |
Cited By (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4000012A (en) | 1973-10-06 | 1976-12-28 | Ciba-Geigy Corporation | Anticorrosive coating of steel |
| US4079006A (en) * | 1973-05-17 | 1978-03-14 | Monsanto Company | Methods of scale inhibition |
| US4383066A (en) | 1980-04-15 | 1983-05-10 | Mitsubishi Gas Chemical Company, Inc. | Polyphenylene ether resin composition |
| WO1985000038A1 (en) * | 1983-06-17 | 1985-01-03 | Kenogard Ab | Guanidated aminophosphonic acid compounds |
| US4707306A (en) * | 1986-12-11 | 1987-11-17 | National Starch And Chemical Corporation | Alpha-aminomethylene phosphonate betaines and polymers prepared therewith |
| US4778865A (en) * | 1986-12-11 | 1988-10-18 | National Starch And Chemical Corporation | Alpha-aminomethylene phosphonate betaines and polymers prepared therewith |
| US4894320A (en) * | 1986-09-25 | 1990-01-16 | Fuji Photo Film Co., Ltd. | Photographic method using bleaching solution containing ferric complex salts and an aromatic compound |
| US5094762A (en) * | 1990-05-09 | 1992-03-10 | Lahalih Shawqui M | Mud drilling fluids, additives and process for making the same |
| US5495042A (en) * | 1993-11-04 | 1996-02-27 | Cytogen Corporation | Non-alkaline purification of aminophosphonic acids |
| EP2112156A1 (en) | 2008-04-25 | 2009-10-28 | Thermphos International B.V. | Method for the Manufacture of Aminoalkylene Phosphonic Acid |
| WO2010136566A1 (en) | 2009-05-28 | 2010-12-02 | Straitmark Holding Ag | Method for the manufacture of amino alkylene phosphonic acids |
| CN102229619A (en) * | 2011-04-26 | 2011-11-02 | 河南清水源科技股份有限公司 | Tetraethylenepentamine heptamethylene phosphonic acid and preparation technology thereof |
| WO2014012990A1 (en) | 2012-07-17 | 2014-01-23 | Straitmark Holding Ag | Method for the synthesis of alpha-aminoalkylenephosphonic acid |
| US8884053B2 (en) | 2008-04-25 | 2014-11-11 | Straitmark Holding Ag | Method for the manufacture of aminoalkylene phosphonic acid |
| CN105152370A (en) * | 2015-09-09 | 2015-12-16 | 西安石油大学 | Preparation method of bis-imidazoline phosphate corrosion and scale inhibitor |
| US9676799B2 (en) | 2012-07-17 | 2017-06-13 | Straitmark Holding Ag | Method for the synthesis of N-(phosphonomethyl)glycine |
| US10280189B2 (en) | 2012-07-17 | 2019-05-07 | Monsanto Technology Llc | Method for the synthesis of aminoalkylenephosphonic acid |
| US10364262B2 (en) | 2012-07-17 | 2019-07-30 | Monsanto Technology Llc | Method for the synthesis of N-phosphonomethyliminodiacetic acid |
-
1967
- 1967-01-27 GB GB1230121D patent/GB1230121A/en not_active Expired
Cited By (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4079006A (en) * | 1973-05-17 | 1978-03-14 | Monsanto Company | Methods of scale inhibition |
| US4000012A (en) | 1973-10-06 | 1976-12-28 | Ciba-Geigy Corporation | Anticorrosive coating of steel |
| US4383066A (en) | 1980-04-15 | 1983-05-10 | Mitsubishi Gas Chemical Company, Inc. | Polyphenylene ether resin composition |
| WO1985000038A1 (en) * | 1983-06-17 | 1985-01-03 | Kenogard Ab | Guanidated aminophosphonic acid compounds |
| US4600429A (en) * | 1983-06-17 | 1986-07-15 | Kenogard Ab | Guanidated aminophosphonic acid compounds |
| US4894320A (en) * | 1986-09-25 | 1990-01-16 | Fuji Photo Film Co., Ltd. | Photographic method using bleaching solution containing ferric complex salts and an aromatic compound |
| US4707306A (en) * | 1986-12-11 | 1987-11-17 | National Starch And Chemical Corporation | Alpha-aminomethylene phosphonate betaines and polymers prepared therewith |
| US4778865A (en) * | 1986-12-11 | 1988-10-18 | National Starch And Chemical Corporation | Alpha-aminomethylene phosphonate betaines and polymers prepared therewith |
| US5094762A (en) * | 1990-05-09 | 1992-03-10 | Lahalih Shawqui M | Mud drilling fluids, additives and process for making the same |
| US5495042A (en) * | 1993-11-04 | 1996-02-27 | Cytogen Corporation | Non-alkaline purification of aminophosphonic acids |
| EP2112156A1 (en) | 2008-04-25 | 2009-10-28 | Thermphos International B.V. | Method for the Manufacture of Aminoalkylene Phosphonic Acid |
| US8884053B2 (en) | 2008-04-25 | 2014-11-11 | Straitmark Holding Ag | Method for the manufacture of aminoalkylene phosphonic acid |
| WO2010136566A1 (en) | 2009-05-28 | 2010-12-02 | Straitmark Holding Ag | Method for the manufacture of amino alkylene phosphonic acids |
| CN102229619A (en) * | 2011-04-26 | 2011-11-02 | 河南清水源科技股份有限公司 | Tetraethylenepentamine heptamethylene phosphonic acid and preparation technology thereof |
| WO2014012990A1 (en) | 2012-07-17 | 2014-01-23 | Straitmark Holding Ag | Method for the synthesis of alpha-aminoalkylenephosphonic acid |
| US9676799B2 (en) | 2012-07-17 | 2017-06-13 | Straitmark Holding Ag | Method for the synthesis of N-(phosphonomethyl)glycine |
| US10280189B2 (en) | 2012-07-17 | 2019-05-07 | Monsanto Technology Llc | Method for the synthesis of aminoalkylenephosphonic acid |
| US10364262B2 (en) | 2012-07-17 | 2019-07-30 | Monsanto Technology Llc | Method for the synthesis of N-phosphonomethyliminodiacetic acid |
| US10464958B2 (en) | 2012-07-17 | 2019-11-05 | Monsanto Technology Llc | Method for the synthesis of alpha-aminoalkylenephosphonic acid |
| CN105152370A (en) * | 2015-09-09 | 2015-12-16 | 西安石油大学 | Preparation method of bis-imidazoline phosphate corrosion and scale inhibitor |
| CN105152370B (en) * | 2015-09-09 | 2017-08-25 | 西安石油大学 | A kind of preparation method of bi-imidazoline phosphonate corrosion inhibiting and descaling agent |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PE | Patent expired |