EP0109406A1 - Verfahren zur herstellung von aminoacetonitrilen - Google Patents

Verfahren zur herstellung von aminoacetonitrilen

Info

Publication number: EP0109406A1
Authority: EP; European Patent Office
Prior art keywords: acid; catalyst; ch2ch2; preparation; cooh
Prior art date: 1982-05-18
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 Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Withdrawn

Application number

EP83901402A

Other languages

German (de)

English (en)

French (fr)

Inventor

Georg L. Busch

Hans-Peter Meier

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.)

CEMONA AG

Original Assignee

CEMONA AG

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.)

1982-05-18

Filing date

1983-05-06

Publication date

1984-05-30

1983-05-06 Application filed by CEMONA AG filed Critical CEMONA AG

1984-05-30 Publication of EP0109406A1 publication Critical patent/EP0109406A1/de

Status Withdrawn legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 13
238000002360 preparation method Methods 0.000 title claims abstract description 10
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 36
LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims abstract description 27
239000003054 catalyst Substances 0.000 claims abstract description 22
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 18
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims abstract description 14
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims abstract description 12
229910021529 ammonia Inorganic materials 0.000 claims abstract description 9
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims abstract description 7
229960002449 glycine Drugs 0.000 claims abstract description 7
235000013905 glycine and its sodium salt Nutrition 0.000 claims abstract description 7
RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims abstract description 6
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 claims description 20
FDWRKVKXYZRYOD-UHFFFAOYSA-N 2-[2-[bis(cyanomethyl)amino]ethyl-(cyanomethyl)amino]acetonitrile Chemical compound N#CCN(CC#N)CCN(CC#N)CC#N FDWRKVKXYZRYOD-UHFFFAOYSA-N 0.000 claims description 16
LJAIDEYQVIJERM-UHFFFAOYSA-N 2-[bis(cyanomethyl)amino]acetonitrile Chemical compound N#CCN(CC#N)CC#N LJAIDEYQVIJERM-UHFFFAOYSA-N 0.000 claims description 12
MGFYIUFZLHCRTH-UHFFFAOYSA-N nitrilotriacetic acid Chemical compound OC(=O)CN(CC(O)=O)CC(O)=O MGFYIUFZLHCRTH-UHFFFAOYSA-N 0.000 claims description 12
QPCDCPDFJACHGM-UHFFFAOYSA-N N,N-bis{2-[bis(carboxymethyl)amino]ethyl}glycine Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(=O)O)CCN(CC(O)=O)CC(O)=O QPCDCPDFJACHGM-UHFFFAOYSA-N 0.000 claims description 10
125000000896 monocarboxylic acid group Chemical group 0.000 claims description 10
229960003330 pentetic acid Drugs 0.000 claims description 10
238000004519 manufacturing process Methods 0.000 claims description 9
150000008361 aminoacetonitriles Chemical class 0.000 claims description 5
KKEBXNMGHUCPEZ-UHFFFAOYSA-N 4-phenyl-1-(2-sulfanylethyl)imidazolidin-2-one Chemical compound N1C(=O)N(CCS)CC1C1=CC=CC=C1 KKEBXNMGHUCPEZ-UHFFFAOYSA-N 0.000 claims description 3
BDDLHHRCDSJVKV-UHFFFAOYSA-N 7028-40-2 Chemical compound CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O BDDLHHRCDSJVKV-UHFFFAOYSA-N 0.000 claims 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
150000001875 compounds Chemical class 0.000 abstract description 2
229960001484 edetic acid Drugs 0.000 description 18
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
239000012452 mother liquor Substances 0.000 description 9
239000000047 product Substances 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 7
238000001704 evaporation Methods 0.000 description 6
230000008020 evaporation Effects 0.000 description 5
AGMNQPKGRCRYQP-UHFFFAOYSA-N 2-[2-[2-[bis(carboxymethyl)amino]ethylamino]ethyl-(carboxymethyl)amino]acetic acid Chemical compound OC(=O)CN(CC(O)=O)CCNCCN(CC(O)=O)CC(O)=O AGMNQPKGRCRYQP-UHFFFAOYSA-N 0.000 description 4
NBZBKCUXIYYUSX-UHFFFAOYSA-N iminodiacetic acid Chemical compound OC(=O)CNCC(O)=O NBZBKCUXIYYUSX-UHFFFAOYSA-N 0.000 description 4
BSRDNMMLQYNQQD-UHFFFAOYSA-N iminodiacetonitrile Chemical compound N#CCNCC#N BSRDNMMLQYNQQD-UHFFFAOYSA-N 0.000 description 4
239000002351 wastewater Substances 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
230000002378 acidificating effect Effects 0.000 description 3
239000008139 complexing agent Substances 0.000 description 3
150000007524 organic acids Chemical class 0.000 description 3
235000005985 organic acids Nutrition 0.000 description 3
ODINCKMPIJJUCX-UHFFFAOYSA-N Calcium oxide Chemical compound [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
239000008098 formaldehyde solution Substances 0.000 description 2
VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 2
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
239000000126 substance Substances 0.000 description 2
230000001502 supplementing effect Effects 0.000 description 2
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
PGEVXZQXDUWQQL-UHFFFAOYSA-N C(C)#N.C(C)#N.C(C)#N.C(C)#N.NCCNCCN Chemical compound C(C)#N.C(C)#N.C(C)#N.C(C)#N.NCCNCCN PGEVXZQXDUWQQL-UHFFFAOYSA-N 0.000 description 1
101001056794 Homo sapiens Inosine triphosphate pyrophosphatase Proteins 0.000 description 1
102100025458 Inosine triphosphate pyrophosphatase Human genes 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
DFNYGALUNNFWKJ-UHFFFAOYSA-N aminoacetonitrile Chemical compound NCC#N DFNYGALUNNFWKJ-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000000292 calcium oxide Substances 0.000 description 1
235000012255 calcium oxide Nutrition 0.000 description 1
FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000006215 cyanomethylation reaction Methods 0.000 description 1
239000003599 detergent Substances 0.000 description 1
238000002845 discoloration Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
229910001385 heavy metal Inorganic materials 0.000 description 1
125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
239000004312 hexamethylene tetramine Substances 0.000 description 1
235000010299 hexamethylene tetramine Nutrition 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
230000007257 malfunction Effects 0.000 description 1
239000000203 mixture Substances 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
239000002574 poison Substances 0.000 description 1
231100000614 poison Toxicity 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
239000010865 sewage Substances 0.000 description 1
238000010186 staining Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Classifications

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

Definitions

the invention relates to a process for the preparation of aminoacetonitriles, in particular nitrilotriacetonitrile (NTAN), iminodiacetonitrile (IDAN), ethylenediamine-tetraacetonitrile (EDTN), diethylenetriamine-pentaacetonitrile (DTPAN) and diethylenetriamine-tetraacetonitrile of the general formula (I)
NTAN nitrilotriacetonitrile
IDAN iminodiacetonitrile
EDTN ethylenediamine-tetraacetonitrile
DTPAN diethylenetriamine-pentaacetonitrile
I diethylenetriamine-tetraacetonitrile
NTA nitrilotriacetic acid
IDA iminodiacetic acid
EDTA ethylenediaminetetraacetic acid
DTPA diethylenetriaminepentaacetic acid
nitrilotriacetonitrile is obtained in the highest yields by reacting ammonia with formaldehyde and hydrocyanic acid in the presence of nitrilotriacetic acid as a catalyst.
the nitriloacetonitrile obtained contains slightly more than half of those used.
Nitrilotriacetic acid. The rest is in the mother liquor. After evaporation and replacement of the nitrilotriacetic acid (NTA) separated off with the nitriloacetonitrile by fresh NTA, this is used again as a catalyst in the subsequent batch, etc.
NTA nitrilotriacetic acid
ethylenediaminetetraacetonitrile (EDTN) is obtained in yields of 95 to 98% of theory if ethylenediamine, formaldehyde and hydrocyanic acid are reacted in the presence of about 3 mol% of ethylenediaminetetraacetic acid (EDTA).
EDTA ethylenediaminetetraacetic acid
the mother liquor can be reused after evaporating and supplementing the EDTA separated with the EDTN. The reuse can be repeated a few times.
the process for the preparation of aminoacetonitriles of the general formula (I) by reacting ammonia, ethylenediamine or diethylenetriamine with formaldehyde and hydrocyanic acid is accordingly characterized in that the catalyst comprises the aminoacetic acid of the formula I belonging to the acetonitrile of the formula I to be prepared (II)
NTAN nitrilotriacetic acid
EDTA ethylene diamine tetraacetic acid
DTPAN diethylenetriaminepentaacetonitrile
DTPA diethylenetriaminepentaacetic acid
Ammonia is "converted by reaction with formalin in hexamethylene lentetramin.
NTA nitrilotriacetic acid
the product is filtered off and dried. It contains 510 g nitrilotriacetonitrile "(NTAN), which are 95% of theory, and 8 g of nitrilotriacetic acid (NTA).
NTAN nitrilotriacetonitrile
the Mut ⁇ terlauge is evaporated, the evaporation residue with 8 g of fresh NTA added and used in subsequent approach with equal success as a catalyst .
ethylenediaminetetraacetonitrile forms.
the product is filtered off and dried. It consists of 210 g of ethylenediaminetetraacetonitrile (that is 97% of theory) and 7.2 g of ethylenediaminetetraacetic acid.
the mother liquor is evaporated.
the residue contains 1.6 g of ethylenediaminetetraacetic acid.
it is fresher after being mixed with 7.2 g
Ethylene diamine tetraacetic acid was used again as a catalyst.
the mother liquor is evaporated, 5.6 g of fresh ethylenediaminetetraacetic acid are added, and the approach is used again as a catalyst, etc.
the mother liquor After evaporation and the addition of 8.3 g of DTPA, the mother liquor can be used with practically the same success as a catalyst for the subsequent same batch.
iminodiacetonitrile which contains small amounts of EDA is obtained by reacting ammonia with a little formalin and hydrocyanic acid in the presence of iminodiacetic acid (IDA). After evaporation and replacement of lost EDA, the mother liquor can be used as a catalyst in the subsequent batch.
IDA iminodiacetic acid
the mother liquor can be used repeatedly after evaporation and addition of the lost diethylenetriamine tetraacetic acid.

Landscapes

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

EP83901402A 1982-05-18 1983-05-06 Verfahren zur herstellung von aminoacetonitrilen Withdrawn EP0109406A1 (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CH3077/82		1982-05-18
CH307782A CH646140A5 (de)	1982-05-18	1982-05-18	Verfahren zur herstellung von aminoacetonitrilen.

Publications (1)

Publication Number	Publication Date
EP0109406A1 true EP0109406A1 (de)	1984-05-30

Family

ID=4248115

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
EP83901402A Withdrawn EP0109406A1 (de)	1982-05-18	1983-05-06	Verfahren zur herstellung von aminoacetonitrilen

Country Status (5)

Country	Link
EP (1)	EP0109406A1 (it)
CH (1)	CH646140A5 (it)
ES (1)	ES522516A0 (it)
IT (1)	IT1163385B (it)
WO (1)	WO1983004020A1 (it)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN104387285A (zh) *	2014-10-27	2015-03-04	石家庄杰克化工有限公司	制备二乙烯三胺五乙酸五钠盐的工艺

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1177646B (de) *	1957-06-12	1964-09-10	Bergwerksgesellschaft Hibernia	Verfahren zur Herstellung von Aminocarbonsaeurenitrilen
FR2057682A5 (it) *	1969-08-26	1971-05-21	Grace W R Ltd
GB1342045A (en) *	1971-01-21	1973-12-25	Monsanto Co	Process for producing nitrilotriacetonitrile
CH624925A5 (en) *	1976-05-08	1981-08-31	Basf Ag	Process for the preparation of glycinenitriles
DE2942437A1 (de) *	1979-10-20	1981-04-23	Degussa Ag, 6000 Frankfurt	Verfahren zur herstellung von iminodiacetonitril

1982
- 1982-05-18 CH CH307782A patent/CH646140A5/de not_active IP Right Cessation
1983
- 1983-05-06 EP EP83901402A patent/EP0109406A1/de not_active Withdrawn
- 1983-05-06 WO PCT/EP1983/000118 patent/WO1983004020A1/de not_active Ceased
- 1983-05-18 IT IT21155/83A patent/IT1163385B/it active
- 1983-05-18 ES ES522516A patent/ES522516A0/es active Granted

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO8304020A1 *

Also Published As

Publication number	Publication date
CH646140A5 (de)	1984-11-15
ES8505513A1 (es)	1984-09-16
WO1983004020A1 (fr)	1983-11-24
IT8321155A1 (it)	1984-11-18
IT1163385B (it)	1987-04-08
ES522516A0 (es)	1984-09-16
IT8321155A0 (it)	1983-05-18

Legal Events

Date	Code	Title	Description
1984-03-31	PUAI	Public reference made under article 153(3) epc to a published international application that has entered the european phase	Free format text: ORIGINAL CODE: 0009012
1984-05-30	AK	Designated contracting states	Designated state(s): AT BE CH DE FR GB LI LU NL SE
1984-09-12	STAA	Information on the status of an ep patent application or granted ep patent	Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN
1984-11-14	18D	Application deemed to be withdrawn	Effective date: 19840425
2007-08-08	RIN1	Information on inventor provided before grant (corrected)	Inventor name: MEIER, HANS-PETER Inventor name: BUSCH, GEORG L.

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