JPH08508284A - 製 法 - Google Patents
製 法Info
- Publication number
- JPH08508284A JPH08508284A JP6521779A JP52177994A JPH08508284A JP H08508284 A JPH08508284 A JP H08508284A JP 6521779 A JP6521779 A JP 6521779A JP 52177994 A JP52177994 A JP 52177994A JP H08508284 A JPH08508284 A JP H08508284A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- water
- compound
- reaction
- acid
- 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.)
- Granted
Links
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 30
- 150000001875 compounds Chemical class 0.000 claims abstract description 80
- 238000000034 method Methods 0.000 claims abstract description 68
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 60
- MGRVRXRGTBOSHW-UHFFFAOYSA-N (aminomethyl)phosphonic acid Chemical compound NCP(O)(O)=O MGRVRXRGTBOSHW-UHFFFAOYSA-N 0.000 claims abstract description 58
- 230000003301 hydrolyzing effect Effects 0.000 claims abstract description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 89
- 239000002904 solvent Substances 0.000 claims description 81
- 238000006243 chemical reaction Methods 0.000 claims description 68
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims description 54
- 239000000203 mixture Substances 0.000 claims description 43
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 41
- 238000006460 hydrolysis reaction Methods 0.000 claims description 35
- 238000004821 distillation Methods 0.000 claims description 20
- 239000008346 aqueous phase Substances 0.000 claims description 18
- 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 description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000003107 substituted aryl group Chemical group 0.000 claims description 7
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 claims description 6
- 238000002955 isolation Methods 0.000 claims description 6
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 150000002825 nitriles Chemical class 0.000 claims description 4
- 239000003849 aromatic solvent Substances 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 2
- 238000000354 decomposition reaction Methods 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 239000011574 phosphorus Substances 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 60
- 230000007062 hydrolysis Effects 0.000 description 33
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 28
- QUBQYFYWUJJAAK-UHFFFAOYSA-N oxymethurea Chemical compound OCNC(=O)NCO QUBQYFYWUJJAAK-UHFFFAOYSA-N 0.000 description 23
- 229950005308 oxymethurea Drugs 0.000 description 23
- ALUHJNDTKQCVJX-UHFFFAOYSA-N (phosphonomethylcarbamoylamino)methylphosphonic acid Chemical compound OP(O)(=O)CNC(=O)NCP(O)(O)=O ALUHJNDTKQCVJX-UHFFFAOYSA-N 0.000 description 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
- 238000010992 reflux Methods 0.000 description 19
- 239000000047 product Substances 0.000 description 18
- 239000000243 solution Substances 0.000 description 17
- 239000007858 starting material Substances 0.000 description 16
- 239000002253 acid Substances 0.000 description 15
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 11
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical group O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic acid anhydride Natural products CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 10
- -1 glyoxylic acid ester Chemical class 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000001816 cooling Methods 0.000 description 9
- GTSOBGIMTNKIPJ-UHFFFAOYSA-N OP(Cl)=O Chemical class OP(Cl)=O GTSOBGIMTNKIPJ-UHFFFAOYSA-N 0.000 description 8
- 239000012071 phase Substances 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 7
- 239000008096 xylene Substances 0.000 description 7
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical group [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- 239000012429 reaction media Substances 0.000 description 6
- 239000002002 slurry Substances 0.000 description 6
- 238000013519 translation Methods 0.000 description 6
- 230000014616 translation Effects 0.000 description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 239000004202 carbamide Substances 0.000 description 5
- 239000001569 carbon dioxide Substances 0.000 description 5
- 229910002092 carbon dioxide Inorganic materials 0.000 description 5
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 4
- HHLFWLYXYJOTON-UHFFFAOYSA-N Glyoxylic acid Natural products OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 4
- LXCYSACZTOKNNS-UHFFFAOYSA-N diethoxy(oxo)phosphanium Chemical compound CCO[P+](=O)OCC LXCYSACZTOKNNS-UHFFFAOYSA-N 0.000 description 4
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000012265 solid product Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 238000005292 vacuum distillation Methods 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- VGGLHLAESQEWCR-UHFFFAOYSA-N N-(hydroxymethyl)urea Chemical compound NC(=O)NCO VGGLHLAESQEWCR-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000007810 chemical reaction solvent Substances 0.000 description 3
- 239000013626 chemical specie Substances 0.000 description 3
- INJBDKCHQWVDGT-UHFFFAOYSA-N chloro(diethyl)phosphane Chemical compound CCP(Cl)CC INJBDKCHQWVDGT-UHFFFAOYSA-N 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 3
- XKALZGSIEJZJCZ-UHFFFAOYSA-N 1,3-bis(methoxymethyl)urea Chemical compound COCNC(=O)NCOC XKALZGSIEJZJCZ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- 238000005903 acid hydrolysis reaction Methods 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- SULWMEGSVQCTSK-UHFFFAOYSA-N diethyl hydrogen phosphite Chemical compound CCOP(O)OCC SULWMEGSVQCTSK-UHFFFAOYSA-N 0.000 description 2
- CZHYKKAKFWLGJO-UHFFFAOYSA-N dimethyl phosphite Chemical compound COP([O-])OC CZHYKKAKFWLGJO-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 2
- 229940015043 glyoxal Drugs 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000002363 herbicidal effect Effects 0.000 description 2
- 239000004009 herbicide Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- OTZTYSZKWXNPTG-UHFFFAOYSA-N methanamine;2-(phosphonomethylamino)acetic acid Chemical compound NC.OC(=O)CNCP(O)(O)=O OTZTYSZKWXNPTG-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 2
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- RDBWDQFBWUQTDC-UHFFFAOYSA-N (carbamoylamino)methylphosphonic acid Chemical compound NC(=O)NCP(O)(O)=O RDBWDQFBWUQTDC-UHFFFAOYSA-N 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- 229930194542 Keto Natural products 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- XGEGHDBEHXKFPX-UHFFFAOYSA-N N-methylthiourea Natural products CNC(N)=O XGEGHDBEHXKFPX-UHFFFAOYSA-N 0.000 description 1
- VIHKPMPEMDBCOA-UHFFFAOYSA-N P(O)(O)=O.NC Chemical compound P(O)(O)=O.NC VIHKPMPEMDBCOA-UHFFFAOYSA-N 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- VFCAUIASFOLMEI-UHFFFAOYSA-L disodium;phosphonatomethanamine Chemical compound [Na+].[Na+].NCP([O-])([O-])=O VFCAUIASFOLMEI-UHFFFAOYSA-L 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- XGEGHDBEHXKFPX-NJFSPNSNSA-N methylurea Chemical compound [14CH3]NC(N)=O XGEGHDBEHXKFPX-NJFSPNSNSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical compound OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
- 229910001948 sodium oxide Inorganic materials 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 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)]
-
- 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)]
- C07F9/42—Halides thereof
-
- 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
-
- 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)]
- C07F9/40—Esters thereof
-
- 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)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Glass Compositions (AREA)
- Iron Core Of Rotating Electric Machines (AREA)
- Saccharide Compounds (AREA)
Abstract
Description
Claims (1)
- 【特許請求の範囲】 1.次の工程: (a)式:R−CH2−NH−CO−NH−CH2−R1[式中、RとR1は同一 又は異なる基であり、ホスホン化脱離基を表す]で示される化合物をホスホン化 剤と反応させる工程と;次に (b)工程(a)の生成物を加水分解して、アミノメタンホスホン酸を形成す る工程と を含むアミノメタンホスホン酸の製造方法。 2.RとR1が同一であり、ヒドロキシ又はC1−C4アルコキシを表す請求 項1記載の方法。 3.ホスホン化剤が(i)三塩化リン、(ii)亜リン酸、(iii)ジアルキ ルホスフィット、(iv)式(VI): (Cl)nP(OR1)3-n(VI) [式中、nは1又は2であり、R1は任意に置換されたアルキル、例えば任意に 置換されたC1−C7アルキル若しくは任意に置換されたアリールである] 示される化合物又はこのような化合物の混合物、又は(v)式:R1OH[式中 、R1は本明細書で定義する通りである]のアルコールとの混合物としての三塩 化リンである請求項1又は2に記載の方法。 4.ホスホン化剤が式(VI)[式中、nは1であり、R1はC1−C7アル キルである]の化合物である請求項3記載の方法。 5.ホスホン化剤が三塩化リンと式:R1OH[式中、R1はC1−C7アルキ ルである]のアルコールとの混合物であり、三塩化リン 1モルにつきアルコー ルR1OH 1.8〜2.2モルが用いられる請求項3記載の方法。 6.反応(a)を0℃〜50℃の温度において実施する請求項1〜5のいず れかに記載の方法。 7.加水分解反応(b)を100℃〜200℃の温度において、圧力を適当 に調節して実施する請求項1〜6のいずれかに記載の方法。 8.反応(a)を、ケトン、塩素化炭化水素、芳香族溶媒、ニトリル又は無 水カルボン酸若しくはエステルである溶媒の存在下で実施する請求項1〜7のい ずれかに記載の方法。 9.反応(a)を水混和性溶媒の存在下で実施し、この水混和性溶媒を加水 分解工程(b)の完成前に分離して、水不混和性溶媒と置換する請求項1〜7の いずれかに記載の方法。 10.アミノメタンホスホン酸の製造方法であって、 (1)式:R−CH2−NH−CO−NH−CH2−R1[式中、RとR1は同一 又は異なる基であり、ホスホン化脱離基を表す]で示される化合物を、三塩化リ ン若しくは式:ClP(OR1)2[式中、R1はC1−C7アルキルである]のジ アルキルクロロホスフィネートであるホスホン化剤又は、三塩化リンと式:R1 OHのアルコールとの混合物であるホスホン化剤と、水混和性溶媒の存在下で反 応させて、ホスホン化剤が三塩化リンである場合には式(II)化合物を形成し 、ホスホン化剤がジアルキルクロロホスフィネートであるか、又は三塩化リンと アルコールR1OHとの混合物である場合には式(II’)化合物を形成する工 程 と; (2)式(II)又は式(II’)化合物を緩和な条件下で水によって加水分 解して、式(IV)化合物を形成する工程 と; (3)水混和性溶媒を蒸留によって分離して、これを水不混和性溶媒と置換す る工程と; (4)水を加えて、このようにして形成された水相中に式(IV)化合物を抽 出する工程と; (5)工程(4)からの水相を100℃〜200℃の温度において、圧力を適 当に調節して加水分解し、それによってアミノメタンホスホン酸を形成する工程 と を含む前記製造方法。 11.アミノメタンホスホン酸生成物を、単離せずに、さらに反応させて、 N−ホスホノメチルグリシンを形成する請求項1〜10のいずれかに記載の方法 。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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GB939307235A GB9307235D0 (en) | 1993-04-07 | 1993-04-07 | Process |
GB9307235.3 | 1993-04-07 | ||
PCT/GB1994/000500 WO1994022880A1 (en) | 1993-04-07 | 1994-03-15 | Process for the manufacture of aminomethanephosphonic acid |
Publications (2)
Publication Number | Publication Date |
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JPH08508284A true JPH08508284A (ja) | 1996-09-03 |
JP3547441B2 JP3547441B2 (ja) | 2004-07-28 |
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JP52177994A Expired - Fee Related JP3547441B2 (ja) | 1993-04-07 | 1994-03-15 | 製法 |
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US (1) | US5471000A (ja) |
EP (1) | EP0693074B1 (ja) |
JP (1) | JP3547441B2 (ja) |
KR (1) | KR100253674B1 (ja) |
CN (1) | CN1044250C (ja) |
AT (1) | ATE155789T1 (ja) |
AU (1) | AU680480B2 (ja) |
BG (1) | BG62140B1 (ja) |
BR (1) | BR9406352A (ja) |
CA (1) | CA2158471C (ja) |
CZ (1) | CZ258595A3 (ja) |
DE (1) | DE69404454T2 (ja) |
DK (1) | DK0693074T3 (ja) |
ES (1) | ES2104363T3 (ja) |
FI (1) | FI954786A0 (ja) |
GB (1) | GB9307235D0 (ja) |
GR (1) | GR3024238T3 (ja) |
HU (1) | HU218867B (ja) |
IL (1) | IL108991A (ja) |
MA (1) | MA23155A1 (ja) |
MY (1) | MY110796A (ja) |
NO (1) | NO953992D0 (ja) |
NZ (1) | NZ262449A (ja) |
PL (1) | PL174910B1 (ja) |
SK (1) | SK124795A3 (ja) |
WO (1) | WO1994022880A1 (ja) |
YU (1) | YU14094A (ja) |
ZA (1) | ZA942047B (ja) |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
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DE19717130A1 (de) * | 1997-04-23 | 1998-10-29 | Sueddeutsche Kalkstickstoff | Verfahren zur Herstellung von Aminomethanphosphonsäure |
CN102372594B (zh) * | 2010-08-21 | 2016-02-24 | 武汉工程大学 | 一种反应在制备乙氧氟草醚以及其它有机合成中的应用 |
CN102442957B (zh) * | 2010-10-06 | 2016-01-06 | 武汉工程大学 | Lj反应在光延反应中的应用 |
RU2694047C2 (ru) | 2012-07-17 | 2019-07-09 | МОНСАНТО ТЕКНОЛОДЖИ ЭлЭлСи | Способ синтеза аминоалкиленфосфоновой кислоты |
BR112015000988A2 (pt) | 2012-07-17 | 2017-06-27 | Straitmark Holding Ag | método para a síntese de ácido n-fosfonometiliminodiacético ou derivados do mesmo |
IN2015DN01081A (ja) | 2012-07-17 | 2015-06-26 | Straitmark Holding Ag | |
PL2875037T3 (pl) | 2012-07-17 | 2017-06-30 | Straitmark Holding Ag | Sposób syntezy N-(fosfonometylo)glicyny |
Family Cites Families (8)
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US404406A (en) * | 1889-06-04 | Buckle | ||
US2304156A (en) * | 1940-03-07 | 1942-12-08 | Du Pont | Organic compound and process of preparing the same |
US4044006A (en) * | 1970-06-26 | 1977-08-23 | Stauffer Chemical Company | Oxazine containing ureidoalkylphosphonates |
US3992294A (en) * | 1974-01-07 | 1976-11-16 | Hooker Chemicals & Plastics Corporation | Process for sequestering metal ions |
IL48639A (en) * | 1974-12-11 | 1978-06-15 | Monsanto Co | Process for the production of carbonylaldiminomethanephosphosphonates |
US4221583A (en) * | 1978-12-22 | 1980-09-09 | Monsanto Company | N-Phosphonomethylglycinonitrile and certain derivatives thereof |
US4830788A (en) * | 1987-11-20 | 1989-05-16 | Crompton & Knowles Corporation | Process for preparation of substituted-aminomethylphosphonic acids |
DE4026028A1 (de) * | 1990-08-17 | 1992-02-20 | Hoechst Ag | Verfahren zur herstellung von aminomethanphosphonsaeure und aminomethyl-phosphinsaeuren aus n-hydroxymethyl-amiden |
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1993
- 1993-04-07 GB GB939307235A patent/GB9307235D0/en active Pending
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1994
- 1994-03-15 AU AU62136/94A patent/AU680480B2/en not_active Ceased
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- 1994-03-15 AT AT94909206T patent/ATE155789T1/de not_active IP Right Cessation
- 1994-03-15 CZ CZ952585A patent/CZ258595A3/cs unknown
- 1994-03-15 EP EP94909206A patent/EP0693074B1/en not_active Expired - Lifetime
- 1994-03-15 WO PCT/GB1994/000500 patent/WO1994022880A1/en not_active Application Discontinuation
- 1994-03-15 KR KR1019950704358A patent/KR100253674B1/ko not_active IP Right Cessation
- 1994-03-15 IL IL108991A patent/IL108991A/en not_active IP Right Cessation
- 1994-03-15 DE DE69404454T patent/DE69404454T2/de not_active Expired - Fee Related
- 1994-03-15 NZ NZ262449A patent/NZ262449A/en unknown
- 1994-03-15 ES ES94909206T patent/ES2104363T3/es not_active Expired - Lifetime
- 1994-03-15 DK DK94909206.8T patent/DK0693074T3/da active
- 1994-03-15 BR BR9406352A patent/BR9406352A/pt not_active IP Right Cessation
- 1994-03-15 CA CA002158471A patent/CA2158471C/en not_active Expired - Fee Related
- 1994-03-15 HU HU9502821A patent/HU218867B/hu not_active IP Right Cessation
- 1994-03-15 SK SK1247-95A patent/SK124795A3/sk unknown
- 1994-03-15 JP JP52177994A patent/JP3547441B2/ja not_active Expired - Fee Related
- 1994-03-15 CN CN94191719A patent/CN1044250C/zh not_active Expired - Fee Related
- 1994-03-23 ZA ZA942047A patent/ZA942047B/xx unknown
- 1994-03-24 YU YU14094A patent/YU14094A/sh unknown
- 1994-03-24 US US08/217,399 patent/US5471000A/en not_active Expired - Lifetime
- 1994-04-05 MA MA23460A patent/MA23155A1/fr unknown
- 1994-04-06 MY MYPI94000825A patent/MY110796A/en unknown
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1995
- 1995-10-06 FI FI954786A patent/FI954786A0/fi not_active Application Discontinuation
- 1995-10-06 NO NO953992A patent/NO953992D0/no unknown
- 1995-10-25 BG BG100092A patent/BG62140B1/bg unknown
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1997
- 1997-07-24 GR GR970401526T patent/GR3024238T3/el unknown
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