KR840005155A - N-포스포노메틸글리신의 제조방법 - Google Patents
N-포스포노메틸글리신의 제조방법 Download PDFInfo
- Publication number
- KR840005155A KR840005155A KR1019830001694A KR830001694A KR840005155A KR 840005155 A KR840005155 A KR 840005155A KR 1019830001694 A KR1019830001694 A KR 1019830001694A KR 830001694 A KR830001694 A KR 830001694A KR 840005155 A KR840005155 A KR 840005155A
- Authority
- KR
- South Korea
- Prior art keywords
- salt
- iminourea
- formula
- aryl
- phosphonomethylglycine
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 7
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 title claims 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical class NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims 10
- 229960004198 guanidine Drugs 0.000 claims 9
- 229910052757 nitrogen Inorganic materials 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- AZIHIQIVLANVKD-UHFFFAOYSA-N N-(phosphonomethyl)iminodiacetic acid Chemical compound OC(=O)CN(CC(O)=O)CP(O)(O)=O AZIHIQIVLANVKD-UHFFFAOYSA-N 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 150000001768 cations Chemical class 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 125000005037 alkyl phenyl group Chemical group 0.000 claims 3
- 125000003118 aryl group Chemical group 0.000 claims 3
- -1 aryl iminourea Chemical compound 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 238000007254 oxidation reaction Methods 0.000 claims 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims 2
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 2
- 150000004985 diamines Chemical class 0.000 claims 2
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims 2
- ZEKANFGSDXODPD-UHFFFAOYSA-N glyphosate-isopropylammonium Chemical compound CC(C)N.OC(=O)CNCP(O)(O)=O ZEKANFGSDXODPD-UHFFFAOYSA-N 0.000 claims 2
- 125000005059 halophenyl group Chemical group 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- OWRCNXZUPFZXOS-UHFFFAOYSA-N 1,3-diphenylguanidine Chemical compound C=1C=CC=CC=1NC(=N)NC1=CC=CC=C1 OWRCNXZUPFZXOS-UHFFFAOYSA-N 0.000 claims 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000002877 alkyl aryl group Chemical group 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 238000001914 filtration Methods 0.000 claims 1
- 239000007789 gas Substances 0.000 claims 1
- 150000002332 glycine derivatives Chemical class 0.000 claims 1
- 229910052736 halogen Chemical group 0.000 claims 1
- 150000002367 halogens Chemical group 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 230000002363 herbicidal effect Effects 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 239000007800 oxidant agent Substances 0.000 claims 1
- 239000012266 salt solution Substances 0.000 claims 1
- 239000000243 solution Substances 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 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)]
- C07F9/44—Amides thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
- A01N57/20—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing acyclic or cycloaliphatic radicals
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides
- A01N47/42—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides containing —N=CX2 groups, e.g. isothiourea
-
- 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
- C07F9/3813—N-Phosphonomethylglycine; Salts or complexes thereof
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (9)
- 하기 구조식 Ⅵ의 N-포스포노메틸이미노디아세트산의 아릴치환 이미노우레아를 산화하여 하기 구조식 Ⅶ의 -포스포노메틸글리신 이미노우레아염을 제조한후, 구조식 의 상기 염을 분자량이 600이하이고 pKa가 10 이상인 수용액 형태의 아민, 이미노우레아, 디아민, 또는 디이미노우레아와 반응시킨 다음, 형성된 수용된 N-포스포노레틸굴리신염 생성물로 비수용성 아릴 이미노우레아를 분리하는 것으로 구성된 것을 특징으로 하는 N-포스포노메틸이미노디아세트산 유도체로부터 수용성 모노 및 디 -N-포스포노메틸글리신 아민과 이미노우레아염을 제조하는 방법.상기에서 Ar1과 Ar2는 각가 페닐, 알킬페닐 및 할로페닐로부터 선택된다.
- 제1항에 있어서, 하기 구조식 Ⅵ을 갖는 N-포스포노메틸 이미노디아세트산의 아릴치환 이미노우레아염을 산화하여 하기 구조식 Ⅶ의 N-포스포노메틸글리신 이모노우레아염을 제조한 다음, 구조식 Ⅶ의 염을 적당한 아민, 이미노우레아, 디아민 또는 디이미노우레아와 반응시켜 하기 일반구조식 I의 N-포스포토메틸 글리신 유도체를 제조하는 방법.상기에서, Ar1및 Ar2는 페닐, 알킬페닐 및 할로페닐로부터 각각 독자적으로 선정되며,a) R1, R2및 R3는 수소와 -OR4로부터 독자적으로 선정되며, 여기서 R4는 하기 구조식 Ⅱ의 염-형성양이온 이미노우레아 유도체이며;상기에서, R5, R5′, R6, R6′및 R7은 각각 H, NH2, CH2OH,또는 하이드록시 또는 할로겐에 의해 선택적으로 치환된 아릴, 시클로알킬 또는 직쇄 또는 측쇄알킬 또는 알케닐기, 또는 알킬아릴기이며, 단 1) R1, R2및 R3중 1-2는 R4이고, 2) R5, R5′, R6, R6′중 하나는 아릴 또는 치환된 아릴이며 3)R5, R5′, R6, R6′ 및 중 R7하나는 CH2OH; 또는b) R1, R2및 R3는 수소와 R16으로부터 독자적으로 선택되며, 여기서 R16은 1급, 2급 및 3급 알킬로부터 선정된 유기암모늄의 양이온(이들중 어떠한 것도 2 이상의 아민기르 갖지 않음)과 헤테로싸이클 아민으로부터 선택된 염-형성 양이온이며(단, R1, R2및 R3중 2 이하는 -R16임 );또는c) R1및 R2는 수소이고, R3는 R17이며, 여기서 R17은 하기구조식을 갖는 염-형성 양이온이며;상기에서, R은 C2-C12직쇄 또는 측쇄알킬렌 라이칼로부터 선택되며, R8과 R9는 각각 H 또는 C1-C4알킬기이며; 또는d)R1과 R2는 H이고, R3는 하기 구조식 Ⅳ의 염-형성 양이온이다;상기에서, Y는 N이고 R18은 탄소수 1-12를 갖는 직쇄 또는 측쇄 알킬렌 라이카이고 R19, R11, R12및 R10은 각각 H, 알킬 페닐 또는 알릴이다(단, R19와 R10중 하나만이 알킬, 알릴 또는 페닐이고, R11및 R12중 하나만이 알킬, 아릴 또는 페닐임).
- 제1항에 있어서, 생성된 NPMG염 용액은 재생된 아릴-치환 이미노우레아로부터 여과에 의해 분리되고, 상기 이미노우래아는 구조식 Ⅵ의 염을 제조하는데 사용하기 위해 정제 및 재순환되는 것을 특징으로 하는 방법.
- 제1항에 있어서, 상기 산화반응이 산화제로서 과산화수소를 사용하여 실시되는 것을 특징으로 하는 방법.
- 제1항에 있어서, 상기 산화반응이 금속 또는 활성화 탄소촉매 존재하에 산소 분자 -함유가스를 사용하여 실시되는 것을 특징으로 하는 방법.
- 제1항에 있어서, N,N′-디페닐 구아니딘, N,N′-디-0-톨릴구아니딘, N,N-디-P-톨릴구아니딘, N,N-디-4-에틸페닐 구아니딘, N,N-디-4-클로로페닐 구아니딘과 N,N-디-4-브로모페닐 구아니딘으로부터 선정된 이미노우레아와 N-포스포노메틸이미노디아세트산을 혼합한 다음 깨끗한 용액이 얻어질때까지 혼합물을 가열하믈써 구조식 Ⅵ의 염을 제조하는 방법.
- 제1항에 있어서, 상기 산화반응이 약 70°-120℃에서 실시되는 것을 특징으로 하는 방법.
- 제1항의 공정에 의해 제조된 구조 I의 N-포스포노메틸글리신 이소프로필아민염.
- 제1항의 공정에 의해 제조된 구조식 I의 N-포스포노메틸글리신 이소프로필아민염을 함유하는 제초제조성물.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IL66137A IL66137A (en) | 1982-06-25 | 1982-06-25 | Process for producing n-phosphonomethylglycine isopropyl amine salt and herbicidal compositions prepared therewith |
IL66137 | 1982-06-25 | ||
IL66824A IL66824A0 (en) | 1982-06-25 | 1982-09-17 | Process for producing n-phosphonomethylglycine derivatives and herbicidal compounds and compositions prepared thereby |
IL66824 | 1982-09-17 |
Publications (1)
Publication Number | Publication Date |
---|---|
KR840005155A true KR840005155A (ko) | 1984-11-03 |
Family
ID=26321054
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019830001694A KR840005155A (ko) | 1982-06-25 | 1983-04-21 | N-포스포노메틸글리신의 제조방법 |
Country Status (13)
Country | Link |
---|---|
US (1) | US4486356A (ko) |
EP (1) | EP0098034A3 (ko) |
KR (1) | KR840005155A (ko) |
AU (1) | AU1350283A (ko) |
BR (1) | BR8303513A (ko) |
DK (1) | DK157683A (ko) |
FI (1) | FI831204L (ko) |
GR (1) | GR81421B (ko) |
IL (1) | IL66824A0 (ko) |
NO (1) | NO831287L (ko) |
PL (1) | PL242678A1 (ko) |
PT (1) | PT76635B (ko) |
RO (1) | RO87143A (ko) |
Families Citing this family (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IL68716A (en) * | 1983-05-17 | 1987-03-31 | Geshuri Lab Ltd | Process for producing n-phosphonomethylglycine |
US4579689A (en) * | 1985-02-11 | 1986-04-01 | Monsanto Company | Oxidation with coated catalyst |
US4582650A (en) * | 1985-02-11 | 1986-04-15 | Monsanto Company | Oxidation with encapsulated co-catalyst |
HU204533B (en) * | 1988-11-02 | 1992-01-28 | Nitrokemia Ipartelepek | Process for producing n-phosphono-methyl-glycine |
US5023369A (en) * | 1990-06-25 | 1991-06-11 | Monsanto Company | Process for producing N-phosphonomethylglycine |
IL101539A (en) * | 1991-04-16 | 1998-09-24 | Monsanto Europe Sa | Mono-ammonium salts of the history of N phosphonomethyl glycyl which are not hygroscopes, their preparations and pesticides containing |
US5948938A (en) * | 1995-03-07 | 1999-09-07 | Sankyo Company, Limited | Process for preparing N-phosphonomethylglycine |
ITTO980048A1 (it) * | 1998-01-20 | 1999-07-20 | Ipici Spa | Composizioni erbicide, procedimenti per la loro preparazione ed impieghi |
US6417133B1 (en) | 1998-02-25 | 2002-07-09 | Monsanto Technology Llc | Deeply reduced oxidation catalyst and its use for catalyzing liquid phase oxidation reactions |
DE69905894T2 (de) * | 1998-07-06 | 2003-12-04 | Syngenta Participations Ag | Herstellung von n-phosphonomethylglycin salzen |
DE60115019T2 (de) * | 2000-05-22 | 2006-08-03 | Monsanto Technology Llc. | Reaktionssysteme zur herstellung von n-(phosphonomethyl)glyzin verbindungen |
TW200624171A (en) * | 2004-09-15 | 2006-07-16 | Monsanto Technology Llc | Oxidation catalyst and its use for catalyzing liquid phase oxidation reactions |
US9615463B2 (en) * | 2006-09-22 | 2017-04-04 | Oscar Khaselev | Method for producing a high-aspect ratio conductive pattern on a substrate |
US8252953B2 (en) | 2008-05-01 | 2012-08-28 | Monsanto Technology Llc | Metal utilization in supported, metal-containing catalysts |
WO2010048164A2 (en) * | 2008-10-20 | 2010-04-29 | University Of South Florida | N,n'-di-p-bromophenyl guanidine treatment for stroke at delayed timepoints |
CN104854117B (zh) * | 2012-07-17 | 2018-12-25 | 孟山都技术有限责任公司 | 用于合成n-膦酰基甲基亚氨基二乙酸的方法 |
US11109591B2 (en) * | 2017-04-24 | 2021-09-07 | Taminco Bvba | Single phase liquids of alkanolamine salts of dicamba |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3853530A (en) * | 1971-03-10 | 1974-12-10 | Monsanto Co | Regulating plants with n-phosphonomethylglycine and derivatives thereof |
US3977860A (en) * | 1971-08-09 | 1976-08-31 | Monsanto Company | Herbicidal compositions and methods employing esters of N-phosphonomethylglycine |
US3954848A (en) * | 1972-05-31 | 1976-05-04 | Monsanto Company | Process for producing N-phosphonomethyl glycine |
US3950402A (en) * | 1972-05-31 | 1976-04-13 | Monsanto Company | Process for producing N-phosphonomethyl glycine |
US3969398A (en) * | 1974-05-01 | 1976-07-13 | Monsanto Company | Process for producing N-phosphonomethyl glycine |
US3957431A (en) * | 1975-03-28 | 1976-05-18 | Basf Aktiengesellschaft | Process for easy-care finishing cellulosics |
MX4703E (es) * | 1976-12-20 | 1982-08-04 | Monsanto Co | Procedimiento mejorado para la preparacion de mono y disales de n-fosfonometilglicina |
CH634968A5 (de) * | 1977-04-01 | 1983-03-15 | Ciba Geigy Ag | Herbizides und pflanzenwuchsregulierendes mittel enthaltend eine neue phosphinsaeure oder deren salze, ester, amide oder hydrazide sowie verwendung derselben. |
IL65187A (en) * | 1982-03-08 | 1985-03-31 | Geshuri Lab Ltd | N-phosphonomethylglycine derivatives,processes for their preparation and herbicidal compositions containing them |
-
1982
- 1982-09-17 IL IL66824A patent/IL66824A0/xx unknown
-
1983
- 1983-04-11 DK DK157683A patent/DK157683A/da not_active IP Right Cessation
- 1983-04-11 FI FI831204A patent/FI831204L/fi not_active Application Discontinuation
- 1983-04-12 NO NO831287A patent/NO831287L/no unknown
- 1983-04-13 AU AU13502/83A patent/AU1350283A/en not_active Abandoned
- 1983-04-15 GR GR71101A patent/GR81421B/el unknown
- 1983-04-15 US US06/485,501 patent/US4486356A/en not_active Expired - Fee Related
- 1983-04-21 KR KR1019830001694A patent/KR840005155A/ko not_active Application Discontinuation
- 1983-04-22 EP EP83302314A patent/EP0098034A3/en not_active Withdrawn
- 1983-04-25 RO RO83110775A patent/RO87143A/ro unknown
- 1983-05-04 PT PT76635A patent/PT76635B/pt unknown
- 1983-06-24 BR BR8303513A patent/BR8303513A/pt unknown
- 1983-06-24 PL PL24267883A patent/PL242678A1/xx unknown
Also Published As
Publication number | Publication date |
---|---|
FI831204A0 (fi) | 1983-04-11 |
NO831287L (no) | 1983-12-27 |
FI831204L (fi) | 1983-12-26 |
US4486356A (en) | 1984-12-04 |
PL242678A1 (en) | 1984-07-02 |
PT76635A (en) | 1983-06-01 |
EP0098034A3 (en) | 1984-03-28 |
AU1350283A (en) | 1984-01-05 |
DK157683A (da) | 1983-12-26 |
EP0098034A2 (en) | 1984-01-11 |
BR8303513A (pt) | 1984-02-07 |
RO87143B (ro) | 1985-10-31 |
RO87143A (ro) | 1985-11-30 |
IL66824A0 (en) | 1982-12-31 |
DK157683D0 (da) | 1983-04-11 |
GR81421B (ko) | 1984-12-11 |
PT76635B (en) | 1985-12-20 |
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