KR960701880A - 아미노메탄포스폰산의 제조방법(process for the manufacture of aminomethanephosphonic acid) - Google Patents
아미노메탄포스폰산의 제조방법(process for the manufacture of aminomethanephosphonic acid)Info
- Publication number
- KR960701880A KR960701880A KR1019950704358A KR19950704358A KR960701880A KR 960701880 A KR960701880 A KR 960701880A KR 1019950704358 A KR1019950704358 A KR 1019950704358A KR 19950704358 A KR19950704358 A KR 19950704358A KR 960701880 A KR960701880 A KR 960701880A
- Authority
- KR
- South Korea
- Prior art keywords
- formula
- compound
- phosphorus trichloride
- phosphonating agent
- alcohol
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract 10
- MGRVRXRGTBOSHW-UHFFFAOYSA-N (aminomethyl)phosphonic acid Chemical compound NCP(O)(O)=O MGRVRXRGTBOSHW-UHFFFAOYSA-N 0.000 title claims abstract 6
- 238000004519 manufacturing process Methods 0.000 title claims abstract 3
- 150000001875 compounds Chemical class 0.000 claims abstract 12
- 239000003795 chemical substances by application Substances 0.000 claims abstract 10
- 230000003301 hydrolyzing effect Effects 0.000 claims abstract 4
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims 8
- 239000002904 solvent Substances 0.000 claims 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 5
- 239000000203 mixture Substances 0.000 claims 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 238000006243 chemical reaction Methods 0.000 claims 3
- GTSOBGIMTNKIPJ-UHFFFAOYSA-N OP(Cl)=O Chemical compound OP(Cl)=O GTSOBGIMTNKIPJ-UHFFFAOYSA-N 0.000 claims 2
- 239000008346 aqueous phase Substances 0.000 claims 2
- 238000006460 hydrolysis reaction Methods 0.000 claims 2
- UIQSKEDQPSEGAU-UHFFFAOYSA-N 1-Aminoethylphosphonic Acid Chemical compound CC(N)P(O)(O)=O UIQSKEDQPSEGAU-UHFFFAOYSA-N 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 239000003849 aromatic solvent Substances 0.000 claims 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 150000002576 ketones Chemical class 0.000 claims 1
- 150000002825 nitriles Chemical class 0.000 claims 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- 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 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
본 발명은 a) 식 R-CH2-NH-CO-NH-CH2-R1(식중, R 및 R1은 동일하거나 상이할 수 있으며 포스폰화이탈그룹을 나타냄)의 화합물과 포스폰화제를 반응시키는 단계 및 계속하여 b) 단계 (a)의 생성물을 가수분해시켜 아미노메탄포스폰산을 얻는 단계로 구성되는 아미노메탄포스폰산의 제조방법에 관한다.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (11)
- a) 식 R-CH2-NH-CO-NH-CH2-R1(식중, R 및 R1은 동일하거나 상이할 수도 있으며 포스폰화 이탈 그룹임.)의 화합물을 포스폰화제와 반응시키는 단계 및 계속하여 b) 단계 (a)의 생성물을 가수분해시켜 아미노에탄포스폰산을 얻는 단계로 구성되는 아미노메탄포스폰산의 제조방법.
- 제1항에 있어서, R 및 R1이 동일하고 하이드록시 또는 C1-4알콕시인 방법.
- 제1항 또는 제2항에 있어서, 포스폰화제가 (i) 포스포러스 트리클로라이드, (ii) 아인산, (iii) 디알킬 포스파이트, (iv) 하기 식(Ⅵ)의 화합물 또는 이러한 화합물들의 혼합물 또는 (V) 식 R1OH(식중, R1은 앞에서 정의한 바와 같음)의 알콜과 혼합된 포스포러스 트리클로라이드인 방법.(Cl)nP (OR1)3-n(Ⅵ)식중, n은 1 또는 2이고, R1은 임의 치환된 알킬 또는 임의 치환된 아릴임.
- 제3항에 있어서, 포스폰화제가 상기 식(Ⅵ)(식중, n은 1이고 R1은 C1-7알킬임)의 화합물인 방법.
- 제3항에 있어서, 포스폰화제가 포스포러스 트리클로라이드 및 식 R1OH(식중, R1은 C1-7알킬임)의 알콜의 혼합물이고 포스포러스 트리클로라이드 몰당 1.8-2.2 몰의 알콜(R1OH)을 사용하는 방법.
- 전기한 항들 중 어느 한 항에 있어서, 반응 (a)가 0-50℃의 온도에서 일어나는 방법.
- 전기한 항들 중 어느 항에 있어서, 가수분해 반응 (b)가 100-200℃의 온도 및 이에 따라 조절된 압력에서 일어나는 방법.
- 전기한 항들 중 어느 항에 있어서, 반응 (a)가 케톤, 염소화된 탄화수소, 방향족 용매, 니트릴 또는 무수카복실산 또는 에스테르인 용매의 존재하에서 일어나는 방법.
- 제1항 내지 제7항 중 어느 한 항에 있어서, 반응 (a)가 가수분해 단계 (b)의 종료전에 분리되어 수불혼화성 용매로 대체되는 수혼화성 용매의 존재하에서 일어나는 방법.
- 1) 포스포러스 트리클로라이드 또는 식 ClP(OR1)2(식중, R1은 C1-7알킬임)의 디알킬 클로로포스피네이트인 포스폰화제 또는 식 R1OH의 알콜 및 포스포러스 트리클로라이드의 혼합물인 포스폰화제와, 식 R-CH2-NH-CO-NH-CH2-R1(식중, R 및 R1은 동일하거나 상이할 수 있으며, 포스폰화 이탈그룹임)의 화합물을수혼화성 용매의 존재하에 반응시켜 포스폰화제가 포스포러스 트리클로라이드일 경우 하기 식(Ⅱ)의 화합물을, 포스폰화제가 디알킬 클로로포스피네이트이거나 포스포러스 트리클로라이드 및 알콜(R1OH)의 혼합물일 경우 하기 식(Ⅱ')의 화합물을 얻는 단계2) 온건한 조건하에서 상기 식(Ⅱ) 또는 (Ⅱ')의 화합물을 물로 가수분해시켜 하기 식(Ⅳ)의 화합물을 얻는 단계3) 중류시켜 수혼화성 용매를 분리시킨 다음 이렇계 분리된 수혼화성 용매를 수불혼화성 용매를 대체시키는단계 4) 물을 가하고, 이렇계 형성된 수성상으로 상기 식(Ⅳ)의 화합물을 추출시키는 단계 5) 100-200℃의 온도 및 이에 따라 조절된 압력에서 단제 (4)로부터 얻은 수성 상을 가수분해시켜 아미노메탄포스폰산을 얻는단계로 구성되는 아미노메탄포스폰산의 제조방법.
- 전기한 항들 중 어느 항에 있어서, 아미노메탄포스폰산 생성물을 분리시키지 않고 계속 반응시켜 N-포스포노메틸글리신을 얻는 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
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 |
---|---|
KR960701880A true KR960701880A (ko) | 1996-03-28 |
KR100253674B1 KR100253674B1 (ko) | 2000-05-01 |
Family
ID=10733471
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019950704358A KR100253674B1 (ko) | 1993-04-07 | 1994-03-15 | 아미노메탄포스폰산의 제조방법 |
Country Status (28)
Country | Link |
---|---|
US (1) | US5471000A (ko) |
EP (1) | EP0693074B1 (ko) |
JP (1) | JP3547441B2 (ko) |
KR (1) | KR100253674B1 (ko) |
CN (1) | CN1044250C (ko) |
AT (1) | ATE155789T1 (ko) |
AU (1) | AU680480B2 (ko) |
BG (1) | BG62140B1 (ko) |
BR (1) | BR9406352A (ko) |
CA (1) | CA2158471C (ko) |
CZ (1) | CZ258595A3 (ko) |
DE (1) | DE69404454T2 (ko) |
DK (1) | DK0693074T3 (ko) |
ES (1) | ES2104363T3 (ko) |
FI (1) | FI954786A (ko) |
GB (1) | GB9307235D0 (ko) |
GR (1) | GR3024238T3 (ko) |
HU (1) | HU218867B (ko) |
IL (1) | IL108991A (ko) |
MA (1) | MA23155A1 (ko) |
MY (1) | MY110796A (ko) |
NO (1) | NO953992L (ko) |
NZ (1) | NZ262449A (ko) |
PL (1) | PL174910B1 (ko) |
SK (1) | SK124795A3 (ko) |
WO (1) | WO1994022880A1 (ko) |
YU (1) | YU14094A (ko) |
ZA (1) | ZA942047B (ko) |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
WO2014012986A1 (en) | 2012-07-17 | 2014-01-23 | Straitmark Holding Ag | Method for the synthesis of n-phosphonomethyliminodiacetic acid |
US9676799B2 (en) | 2012-07-17 | 2017-06-13 | Straitmark Holding Ag | Method for the synthesis of N-(phosphonomethyl)glycine |
RU2674022C9 (ru) | 2012-07-17 | 2019-01-24 | МОНСАНТО ТЕКНОЛОДЖИ ЭлЭлСи | Способ синтеза альфа-аминоалкиленфосфоновой кислоты |
RU2694047C2 (ru) | 2012-07-17 | 2019-07-09 | МОНСАНТО ТЕКНОЛОДЖИ ЭлЭлСи | Способ синтеза аминоалкиленфосфоновой кислоты |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
ES443323A1 (es) * | 1974-12-11 | 1977-04-16 | Monsanto Co | Un procedimiento para obtener compuestos de carbonilaldimi- nometanfosfonato. |
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 |
-
1993
- 1993-04-07 GB GB939307235A patent/GB9307235D0/en active Pending
-
1994
- 1994-03-15 CA CA002158471A patent/CA2158471C/en not_active Expired - Fee Related
- 1994-03-15 BR BR9406352A patent/BR9406352A/pt not_active IP Right Cessation
- 1994-03-15 JP JP52177994A patent/JP3547441B2/ja not_active Expired - Fee Related
- 1994-03-15 ES ES94909206T patent/ES2104363T3/es not_active Expired - Lifetime
- 1994-03-15 AU AU62136/94A patent/AU680480B2/en not_active Ceased
- 1994-03-15 AT AT94909206T patent/ATE155789T1/de not_active IP Right Cessation
- 1994-03-15 DE DE69404454T patent/DE69404454T2/de not_active Expired - Fee Related
- 1994-03-15 CZ CZ952585A patent/CZ258595A3/cs unknown
- 1994-03-15 CN CN94191719A patent/CN1044250C/zh not_active Expired - Fee Related
- 1994-03-15 HU HU9502821A patent/HU218867B/hu not_active IP Right Cessation
- 1994-03-15 WO PCT/GB1994/000500 patent/WO1994022880A1/en not_active Application Discontinuation
- 1994-03-15 SK SK1247-95A patent/SK124795A3/sk unknown
- 1994-03-15 EP EP94909206A patent/EP0693074B1/en not_active Expired - Lifetime
- 1994-03-15 DK DK94909206.8T patent/DK0693074T3/da active
- 1994-03-15 IL IL108991A patent/IL108991A/en not_active IP Right Cessation
- 1994-03-15 NZ NZ262449A patent/NZ262449A/en unknown
- 1994-03-15 PL PL94311002A patent/PL174910B1/pl not_active IP Right Cessation
- 1994-03-15 KR KR1019950704358A patent/KR100253674B1/ko not_active IP Right Cessation
- 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
-
1995
- 1995-10-06 NO NO953992A patent/NO953992L/no unknown
- 1995-10-06 FI FI954786A patent/FI954786A/fi not_active Application Discontinuation
- 1995-10-25 BG BG100092A patent/BG62140B1/bg unknown
-
1997
- 1997-07-24 GR GR970401526T patent/GR3024238T3/el unknown
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