JPS6010023B2 - イミノジアセトニトリルの製法 - Google Patents

イミノジアセトニトリルの製法

Info

Publication number: JPS6010023B2
Authority: JP; Japan
Prior art keywords: formaldehyde; reaction; mixture; hcn; hmta
Prior art date: 1975-09-08
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

Application number

JP51106336A

Other languages

English (en)

Japanese (ja)

Other versions

JPS5233621A (en

Inventor

ロジヤー・ロバート・ゴーデツト

ジエームス・エドワード・フイルブルツク

ジヨン・カール・サンバーグ

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

WR Grace and Co

Original Assignee

WR Grace and Co

Priority date (The priority date 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 date listed.)

1975-09-08

Filing date

1976-09-07

Publication date

1985-03-14

1975-09-08 Priority claimed from US05/611,369 external-priority patent/US3988360A/en

1976-09-07 Application filed by WR Grace and Co filed Critical WR Grace and Co

1977-03-14 Publication of JPS5233621A publication Critical patent/JPS5233621A/ja

1985-03-14 Publication of JPS6010023B2 publication Critical patent/JPS6010023B2/ja

Status Expired legal-status Critical Current

Links

BSRDNMMLQYNQQD-UHFFFAOYSA-N iminodiacetonitrile Chemical compound N#CCNCC#N BSRDNMMLQYNQQD-UHFFFAOYSA-N 0.000 title claims description 26
238000004519 manufacturing process Methods 0.000 title description 5
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 112
VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 claims description 46
238000006243 chemical reaction Methods 0.000 claims description 45
239000000203 mixture Substances 0.000 claims description 26
239000007864 aqueous solution Substances 0.000 claims description 24
238000000034 method Methods 0.000 claims description 24
239000011541 reaction mixture Substances 0.000 claims description 11
239000002253 acid Substances 0.000 claims description 6
239000004312 hexamethylene tetramine Substances 0.000 claims description 6
235000010299 hexamethylene tetramine Nutrition 0.000 claims description 6
230000000087 stabilizing effect Effects 0.000 claims description 3
238000010924 continuous production Methods 0.000 claims description 2
LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 62
238000002156 mixing Methods 0.000 description 30
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 19
239000000243 solution Substances 0.000 description 17
238000003860 storage Methods 0.000 description 17
239000000047 product Substances 0.000 description 15
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
NBZBKCUXIYYUSX-UHFFFAOYSA-N iminodiacetic acid Chemical compound OC(=O)CNCC(O)=O NBZBKCUXIYYUSX-UHFFFAOYSA-N 0.000 description 9
239000004471 Glycine Substances 0.000 description 5
229910021529 ammonia Inorganic materials 0.000 description 5
DFNYGALUNNFWKJ-UHFFFAOYSA-N aminoacetonitrile Chemical compound NCC#N DFNYGALUNNFWKJ-UHFFFAOYSA-N 0.000 description 4
239000007788 liquid Substances 0.000 description 4
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 4
229910000069 nitrogen hydride Inorganic materials 0.000 description 4
239000000376 reactant Substances 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
150000008044 alkali metal hydroxides Chemical class 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
238000005070 sampling Methods 0.000 description 3
LJAIDEYQVIJERM-UHFFFAOYSA-N 2-[bis(cyanomethyl)amino]acetonitrile Chemical compound N#CCN(CC#N)CC#N LJAIDEYQVIJERM-UHFFFAOYSA-N 0.000 description 2
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
229910000831 Steel Inorganic materials 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
-1 alkali metal salt Chemical class 0.000 description 2
229910052921 ammonium sulfate Inorganic materials 0.000 description 2
239000012736 aqueous medium Substances 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
229910052802 copper Inorganic materials 0.000 description 2
239000010949 copper Substances 0.000 description 2
239000013078 crystal Substances 0.000 description 2
239000008098 formaldehyde solution Substances 0.000 description 2
LTYRAPJYLUPLCI-UHFFFAOYSA-N glycolonitrile Chemical compound OCC#N LTYRAPJYLUPLCI-UHFFFAOYSA-N 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
239000002609 medium Substances 0.000 description 2
150000002825 nitriles Chemical class 0.000 description 2
238000007747 plating Methods 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
239000010959 steel Substances 0.000 description 2
GFZMFCVDDFHSJK-UHFFFAOYSA-N 2-(methylideneamino)acetonitrile Chemical compound C=NCC#N GFZMFCVDDFHSJK-UHFFFAOYSA-N 0.000 description 1
229910000851 Alloy steel Inorganic materials 0.000 description 1
239000004254 Ammonium phosphate Substances 0.000 description 1
229910000881 Cu alloy Inorganic materials 0.000 description 1
244000241257 Cucumis melo Species 0.000 description 1
235000015510 Cucumis melo subsp melo Nutrition 0.000 description 1
241000252233 Cyprinus carpio Species 0.000 description 1
101100182219 Homo sapiens ALOX12 gene Proteins 0.000 description 1
240000002853 Nelumbo nucifera Species 0.000 description 1
235000006508 Nelumbo nucifera Nutrition 0.000 description 1
235000006510 Nelumbo pentapetala Nutrition 0.000 description 1
102100031949 Polyunsaturated fatty acid lipoxygenase ALOX12 Human genes 0.000 description 1
241000269851 Sarda sarda Species 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
101000988666 Xenopus laevis Histamine N-methyltransferase A Proteins 0.000 description 1
FJJCIZWZNKZHII-UHFFFAOYSA-N [4,6-bis(cyanoamino)-1,3,5-triazin-2-yl]cyanamide Chemical compound N#CNC1=NC(NC#N)=NC(NC#N)=N1 FJJCIZWZNKZHII-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
229910000148 ammonium phosphate Inorganic materials 0.000 description 1
235000019289 ammonium phosphates Nutrition 0.000 description 1
BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
235000011130 ammonium sulphate Nutrition 0.000 description 1
239000012431 aqueous reaction media Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
210000004556 brain Anatomy 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
229910052804 chromium Inorganic materials 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
238000011437 continuous method Methods 0.000 description 1
ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000010908 decantation Methods 0.000 description 1
MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000004744 fabric Substances 0.000 description 1
239000003337 fertilizer Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
238000007429 general method Methods 0.000 description 1
JMANVNJQNLATNU-UHFFFAOYSA-N glycolonitrile Natural products N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
229910010272 inorganic material Inorganic materials 0.000 description 1
239000011147 inorganic material Substances 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
229920000126 latex Polymers 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
MGFYIUFZLHCRTH-UHFFFAOYSA-N nitrilotriacetic acid Chemical compound OC(=O)CN(CC(O)=O)CC(O)=O MGFYIUFZLHCRTH-UHFFFAOYSA-N 0.000 description 1
235000015277 pork Nutrition 0.000 description 1
238000006884 silylation reaction Methods 0.000 description 1
239000002002 slurry Substances 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
229910052719 titanium Inorganic materials 0.000 description 1
229910052720 vanadium Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

JP51106336A 1975-09-08 1976-09-07 イミノジアセトニトリルの製法 Expired JPS6010023B2 (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US05/611,369 US3988360A (en)	1973-11-15	1975-09-08	Process for preparing iminodiacetonitrile
US611369		1975-09-08

Publications (2)

Publication Number	Publication Date
JPS5233621A JPS5233621A (en)	1977-03-14
JPS6010023B2 true JPS6010023B2 (ja)	1985-03-14

Family

ID=24448748

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP51106336A Expired JPS6010023B2 (ja)	1975-09-08	1976-09-07	イミノジアセトニトリルの製法

Country Status (10)

Country	Link
JP (1)	JPS6010023B2 (fr)
BE (1)	BE845867A (fr)
CA (1)	CA1061800A (fr)
DE (1)	DE2639874C2 (fr)
FR (1)	FR2322858A1 (fr)
GB (1)	GB1561144A (fr)
IE (1)	IE43417B1 (fr)
IT (1)	IT1065479B (fr)
NL (1)	NL7609714A (fr)
SE (1)	SE441266B (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2942437A1 (de)	1979-10-20	1981-04-23	Degussa Ag, 6000 Frankfurt	Verfahren zur herstellung von iminodiacetonitril
KR20090121293A (ko) *	2007-03-01	2009-11-25	바스프 에스이	아미노 니트릴의 제조 방법

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR1275593A (fr) *	1960-12-02	1961-11-10	Degussa	Procédé pour produire le nitrile imino-diacétique
US3167580A (en) *	1962-04-12	1965-01-26	American Cyanamid Co	Process for the preparation of iminodiacetonitrile
US3412137A (en) *	1965-10-14	1968-11-19	Geigy Chemical Company	Process for the preparation of nitriles
US3886198A (en) *	1973-12-13	1975-05-27	Grace W R & Co	Process for preparing iminodiacetonitrile

1976
- 1976-03-23 CA CA248,577A patent/CA1061800A/fr not_active Expired
- 1976-08-19 IE IE1846/76A patent/IE43417B1/en unknown
- 1976-09-01 NL NL7609714A patent/NL7609714A/xx not_active Application Discontinuation
- 1976-09-03 BE BE170368A patent/BE845867A/fr not_active IP Right Cessation
- 1976-09-04 DE DE2639874A patent/DE2639874C2/de not_active Expired
- 1976-09-06 SE SE7609835A patent/SE441266B/xx unknown
- 1976-09-06 IT IT26915/76A patent/IT1065479B/it active
- 1976-09-07 FR FR7626920A patent/FR2322858A1/fr active Granted
- 1976-09-07 JP JP51106336A patent/JPS6010023B2/ja not_active Expired
- 1976-09-08 GB GB37231/76A patent/GB1561144A/en not_active Expired

Also Published As

Publication number	Publication date
NL7609714A (nl)	1977-03-10
SE7609835L (sv)	1977-03-09
FR2322858A1 (fr)	1977-04-01
IE43417L (en)	1977-03-08
JPS5233621A (en)	1977-03-14
BE845867A (fr)	1976-12-31
GB1561144A (en)	1980-02-13
SE441266B (sv)	1985-09-23
DE2639874A1 (de)	1977-03-17
CA1061800A (fr)	1979-09-04
DE2639874C2 (de)	1985-06-05
IE43417B1 (en)	1981-02-25
IT1065479B (it)	1985-02-25
FR2322858B1 (fr)	1981-04-30

Publication	Publication Date	Title
US5187301A (en)	1993-02-16	Preparation of iminodiacetonitrile from glycolonitrile
US3988360A (en)	1976-10-26	Process for preparing iminodiacetonitrile
AU600932B2 (en)	1990-08-30	Process for the preparation of iminodiacetonitrile
JPS5823867B2 (ja)	1983-05-18	グアニジン塩類の製造法
CN105985251A (zh)	2016-10-05	一种亚氨基二乙酸等氨基酸类清洁生产工艺
US4704465A (en)	1987-11-03	Process for preparing ethylenediaminetetraacetonitrile
US2564647A (en)	1951-08-14	Hydantoin manufacture
CA1205493A (fr)	1986-06-03	Preparation de nitrilotriacetonitrile
CA1061800A (fr)	1979-09-04	Procede pour la preparation d'iminodiacetonitrile
US3864378A (en)	1975-02-04	Process for preparing 2-hydroxyethyliminodiacetonitrile
US3950384A (en)	1976-04-13	Process for the manufacture of nitrilotriacetonitrile
US4307037A (en)	1981-12-22	Process for the production of iminodiacetonitrile
US5008428A (en)	1991-04-16	Integrated process for the production of aminoacetonitriles
US20230008538A1 (en)	2023-01-12	Process for preparing nitrile intermediates for nitrogen-containing chelators
US3267130A (en)	1966-08-16	Process for synthesizing amino nitriles
IE43027B1 (en)	1980-12-03	Process for preparing iminodiacetonitrile
JPS5949219B2 (ja)	1984-12-01	β−クロロアラニンの製造法
JP2801781B2 (ja)	1998-09-21	グリシンの製造方法
CN1041401C (zh)	1998-12-30	中性一步法生产硫酸钾的方法
US832466A (en)	1906-10-02	Production of ferrocyanids from gas.
US3752821A (en)	1973-08-14	Method for the continuous manufacture of hydantoins especially 5,5-dimethylhydantoin
CA1134861A (fr)	1982-11-02	N-methyleneaminoacetonitrile monomerique
WO1989009766A2 (fr)	1989-10-19	Procede pour preparer de l'acide 2,4,6-triido-5-amino-n-alkylisophthalamique
JPS63208578A (ja)	1988-08-30	４−メチルイミダゾ−ル類の製造方法
USH4H (en)	1985-12-03	Processs for the preparation of iminodiacetonitrile