公开(公告)号：EP0107464A1

公开(公告)日：1984-05-02

申请号：EP83306278.9

申请日：1983-10-17

Applicant: STAUFFER CHEMICAL COMPANY

Inventor： Bayer, Arthur Craig ,  Bowler, Donald Joseph ,  Robbins, Jeffrey Dean

IPC: C07F9/38

CPC classification number: C07F9/65061 ,  C07D233/78 ,  C07F9/3813

Abstract: A process for the production of N-phosphonomethylglycine characterised in that it comprises:

(a) reacting a hydantoin or a 3-substituted hydantoin corresponding to the following general formula:
wherein R represents hydrogen, C 1 -C 10 alkyl, C 6 -C 12 aryl, C 1 -C 10 alkyl-carbonyl and C 6 -C 12 aryl-carbonyl with paraformaldehyde in the presence of a low molecular weight carboxylic acid to produce a mixture of intermediate products including the 1-(hydroxymethyl) derivative of the starting hydantoin;
(b) converting the 1-(hydroxymethyl) derivative to the 1-phosphonomethyl derivative by thereafter adding to the reaction mixture either:

(i) a substituted phosphorus compound selected from phosphorus trichloride and phosphorus tribromide;
(ii) phosphorus acid and an anhydride selected from acetic anhydride, propionic anhydride, butyric anhydride

or a similar asymmetrical anhydride and continuing the reaction to cause completion of the reaction to form the 1-phosphonomethyl derivative;
(c) hydrolyzing the resulting 1-phosphonomethylhydantoin product with a base selected from alkali metal or alkaline earth hydroxides to produce a salt of N-phosphonomethylglycine; and
(d) neutralizing the salt witha strong acid to produce N-phosphonomethylglycine

is disclosed.
The present process provides advantages over the prior art.

Abstract translation: 一种N-膦酰基甲基甘氨酸的制备方法，其特征在于其包括：（a）使与下列通式相应的乙内酰脲或3-取代的乙内酰脲反应：其中R表示氢，C 1 -C 10烷基，C 6 -C 12 芳基，C 1 -C 10烷基羰基和C 6 -C 12芳基 - 羰基与低聚甲醛在低分子量羧酸的存在下反应以产生包括起始乙内酰脲的1-（羟基甲基）衍生物的中间产物的混合物; （b）将1-（羟甲基）衍生物转化为1-膦酰基甲基衍生物，然后向反应混合物中加入：（i）选自三氯化磷和三溴化磷的取代的磷化合物; （ii）磷酸和选自乙酸酐，丙酸酐，丁酸酐或类似的不对称酸酐的酸酐，并继续反应以使反应完成以形成1-膦酰基甲基衍生物; （c）用选自碱金属或碱土金属氢氧化物的碱水解所得的1-膦酰基乙内酰脲产物以产生N-膦酰基甲基甘氨酸的盐; 和（d）用强酸中和盐以产生N-膦酰基甲基甘氨酸。 本方法提供了优于现有技术的优点。

公开(公告)号：EP0047562A1

公开(公告)日：1982-03-17

申请号：EP81200987.6

申请日：1981-09-03

Applicant: STAUFFER CHEMICAL COMPANY

Inventor： Robbins, Jeffrey Dean

IPC: C07C43/164 ,  C07C41/18 ,  C07C15/107

CPC classification number: C07C255/00 ,  C07C43/164 ,  C07C253/14

Abstract: Alkyl and alkoxyalkyl substituted benzenes having the formula
in which R is C 1 -C 5 alkyl, C 1 -C 4 alkoxy, methylenedioxy or hydrogen and R' is C 2 -C 20 alkyl or C 2 -C 20 alkoxyalkyl are prepared from corresponding benzyl halides by a three-step process of cyanation, alkylation, and decyanation.

Abstract translation: 具有式CHEM的烷基和烷氧基烷基取代的苯，其中R是C 1 -C 5烷基，C 1 -C 4烷氧基，亚甲二氧基或氢，R min是C 2 -C 20烷基或C 2 -C 20烷氧基烷基，由相应的苄基卤化物由三 - 氰化，烷基化和脱色的步骤。

公开(公告)号：EP0127972A1

公开(公告)日：1984-12-12

申请号：EP84303307.7

申请日：1984-05-16

Applicant: STAUFFER CHEMICAL COMPANY

Inventor： Robbins, Jeffrey Dean

IPC: C07F9/38

CPC classification number: C07F9/3813

Abstract: A method for the production of N-phosphonomethylglycine and soluble salts thereof is disclosed in which glycinemethylenephosphinic acid or its soluble salts are reacted with an excess of an alkali or alkaline earth base for a period of time and at a sufficient temperature to cause oxidation of the glycinemethylenephosphinic acid or its soluble salts thereof to N-phosphonomethylglycine salts, from which N-phosphonomethylglycine may be obtained by acidification. The N-phosphonomethyleglycine or its soluble salts, are used as herbicides.

Abstract translation: 公开了生产N-膦酰基甲基甘氨酸及其可溶性盐的方法，其中将甘氨酸亚膦酸或其可溶性盐与过量的碱金属或碱土金属碱反应一段时间并在足够的温度下引起氧化 甘氨亚乙基次膦酸或其可溶性盐与N-膦酰基甲基甘氨酸盐反应，通过酸化得到N-膦酰基甲基甘氨酸。 N-膦酰基甲基甘氨酸或其可溶性盐用作除草剂。

公开(公告)号：EP0047562B1

公开(公告)日：1983-11-23

申请号：EP81200987.6

申请日：1981-09-03

Applicant: STAUFFER CHEMICAL COMPANY

Inventor： Robbins, Jeffrey Dean

IPC: C07C43/164 ,  C07C41/18 ,  C07C15/107

CPC classification number: C07C255/00 ,  C07C43/164 ,  C07C253/14

公开(公告)号：EP0107464B1

公开(公告)日：1986-01-08

申请号：EP83306278.9

申请日：1983-10-17

Applicant: STAUFFER CHEMICAL COMPANY

Inventor： Bayer, Arthur Craig ,  Bowler, Donald Joseph ,  Robbins, Jeffrey Dean

IPC: C07F9/38

CPC classification number: C07F9/65061 ,  C07D233/78 ,  C07F9/3813

公开(公告)号：EP0149294A1

公开(公告)日：1985-07-24

申请号：EP84300320.3

申请日：1984-01-19

Applicant: STAUFFER CHEMICAL COMPANY

Inventor： Robbins, Jeffrey Dean

IPC: C07F9/38

CPC classification number: C07F9/3813

Abstract: A method for the preparation of N-phosphonomethylglycine which comprises the steps of (1) reacting 1,3,5-trislalkoxy- or aryloxy-substituted carbonylmethyl) hexahydro-s-triazine, with a substituted phosphorus compound having the formula PXYZ wherein X is a halogen, Y and Z are independently selected from the group consisting of halogen, alkoxy having from 1 to 10 carbon atoms, and aryloxy, in the presence of a protic acid and a low molecular weight carboxylic acid; (2) heating said reactants to a temperature ranging from 10 to 25°C for a sufficient period of time to cause the formation of an N-phosphonomethylglycine ester; and (3) hydrolyzing said phosphonomethylglycine ester to N-phosphonomethylglycine.

Abstract translation: 一种制备N-膦酰基甲基甘氨酸的方法，其包括以下步骤：（1）使1,3,5-三（烷氧基或芳氧基取代的羰基甲基）六氢-s-三嗪与具有式PXYZ的取代的磷化合物反应，其中 X是卤素，Y和Z独立地选自卤素，具有1至10个碳原子的烷氧基和芳氧基，在质子酸和低分子量羧酸的存在下; （2）将所述反应物加热至10至25℃的温度足够的时间以引起N-膦酰基甲基甘氨酸酯的形成; 和（3）将所述膦酰基甲基甘氨酸酯水解成N-膦酰基甲基甘氨酸。