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HRP20231004T1 - Postupak za pripremu n-alkil-nitratoetilnitramina - Google Patents

Postupak za pripremu n-alkil-nitratoetilnitramina Download PDF

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Publication number
HRP20231004T1
HRP20231004T1 HRP20231004TT HRP20231004T HRP20231004T1 HR P20231004 T1 HRP20231004 T1 HR P20231004T1 HR P20231004T T HRP20231004T T HR P20231004TT HR P20231004 T HRP20231004 T HR P20231004T HR P20231004 T1 HRP20231004 T1 HR P20231004T1
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HR
Croatia
Prior art keywords
reaction
carried out
formula
pressure
temperature
Prior art date
Application number
HRP20231004TT
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English (en)
Inventor
Anian Nieder
Tobias WUENSCHE
Anne Theresa Friedrichs
Johannes Kainz
Alexander Huber
Original Assignee
Nitrochemie Aschau Gmbh
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.)
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Publication date
Application filed by Nitrochemie Aschau Gmbh filed Critical Nitrochemie Aschau Gmbh
Publication of HRP20231004T1 publication Critical patent/HRP20231004T1/hr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C241/00—Preparation of compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
    • C07C243/04—N-nitroso compounds
    • C07C243/06—N-nitroso-amines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C241/00—Preparation of compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
    • C07C241/02—Preparation of hydrazines
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J19/0006—Controlling or regulating processes
    • B01J19/002—Avoiding undesirable reactions or side-effects, e.g. avoiding explosions, or improving the yield by suppressing side-reactions
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J19/0093—Microreactors, e.g. miniaturised or microfabricated reactors
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J3/00—Processes of utilising sub-atmospheric or super-atmospheric pressure to effect chemical or physical change of matter; Apparatus therefor
    • B01J3/04—Pressure vessels, e.g. autoclaves
    • B01J3/042—Pressure vessels, e.g. autoclaves in the form of a tube
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
    • C07C243/02—N-nitro compounds
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00002—Chemical plants
    • B01J2219/00027—Process aspects
    • B01J2219/00033—Continuous processes
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00049—Controlling or regulating processes
    • B01J2219/00051—Controlling the temperature
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00049—Controlling or regulating processes
    • B01J2219/00162—Controlling or regulating processes controlling the pressure
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00781—Aspects relating to microreactors
    • B01J2219/00788—Three-dimensional assemblies, i.e. the reactor comprising a form other than a stack of plates
    • B01J2219/00792—One or more tube-shaped elements
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00781—Aspects relating to microreactors
    • B01J2219/00851—Additional features
    • B01J2219/00867—Microreactors placed in series, on the same or on different supports
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
    • C07C201/02—Preparation of esters of nitric acid

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

Claims (15)

1. Postupak za dobivanje spoja formule (I): [image] pri čemu R je alkilna skupina koja ima od 1 do 6 ugljikovih atoma ili skupina formule -CH2-CH2-O-NO2, ili smjesa dvaju ili više takvih spojeva, koji uključuje reakciju spoja formule (II): [image] pri čemu R' je alkilna skupina koja ima od 1 do 6 ugljikovih atoma ili skupina formule -CH2-CH2-OH, ili reakcija odgovarajućih smjesa dva ili više takvih spojeva, s dušičnom kiselinom i zatim sa smjesom najmanje jednog anhidrida kiseline i katalizatora koji sadrži klorid u kontinuiranom postupku, naznačen time što se reakcije provode pri tlaku od 2 bara iznad atmosferskog tlaka do tlaka od 80 bara iznad atmosferskog tlaka.
2. Postupak prema zahtjevu 1, naznačen time što se nakon reakcija reakcijska smjesa dovodi u kontakt s vodom ili vodenom alkalnom otopinom.
3. Postupak prema zahtjevu 1 ili 2, naznačen time što R je metilna, etilna ili butilna skupina ili skupina formule -CH2-CH2-O-NO2 i R' je metilna, etilna ili butilna skupina ili skupina formule -CH2-CH2-OH.
4. Postupak prema bilo kojem od prethodnih zahtjeva, naznačen time što se reakcije provode u jednom ili više reaktora s kontinuiranim protokom.
5. Postupak prema bilo kojem od prethodnih zahtjeva 1 do 3, naznačen time što se reakcije provode u jednom ili više cjevastih reaktora.
6. Postupak prema bilo kojem od prethodnih zahtjeva 1 do 3, naznačen time što se reakcije provode u jednom ili više mikroreaktora.
7. Postupak prema bilo kojem od prethodnih zahtjeva, naznačen time što se reakcije provode pri tlaku od 2 bara iznad atmosferskog tlaka do tlaka od 18 bara iznad atmosferskog tlaka, poželjno pri tlaku od 3 do 12 bara iznad atmosferskog tlaka.
8. Postupak prema bilo kojem od prethodnih zahtjeva, naznačen time što se reakcija s dušičnom kiselinom provodi na temperaturi od -20°C do 30°C; naročito na temperaturi od -10°C do 10°C ili na temperaturi od -15°C do -5°C.
9. Postupak prema bilo kojem od prethodnih zahtjeva, naznačen time što se reakcija sa smjesom najmanje jednog anhidrida kiseline i katalizatora koji sadrži klorid provodi na temperaturi od 20°C do 60°C; naročito na temperaturi od 27°C do 36°C ili na temperaturi od 25°C do 35°C.
10. Postupak prema bilo kojem od prethodnih zahtjeva, naznačen time što se kao anhidrid kiseline koristi anhidrid octene kiseline.
11. Postupak prema bilo kojem od prethodnih zahtjeva, naznačen time što se kao katalizator koji sadrži klorid koristi klorovodik.
12. Postupak prema bilo kojem od prethodnih zahtjeva, naznačen time što se dušična kiselina korištena u reakciji koristi u koncentraciji od 75 do 96 % u vodi.
13. Postupak prema bilo kojem od prethodnih zahtjeva, naznačen time što se priprema smjesa etil-NENA (R = etil) i metil-NENA (R = metil).
14. Postupak prema bilo kojem od prethodnih zahtjeva, naznačen time što je mnoštvo identičnih ili različitih mikroreaktora povezano jedan za drugim u seriju; naročito naznačen time što su najmanje dva (naročito najmanje tri) mikroreaktora spojena u seriju.
15. Postupak prema bilo kojem od prethodnih zahtjeva, naznačen time što se reakcija između spoja formule (II) i dušične kiseline provodi u mikroreaktoru kao kontinuirani proces i produkt iz tog mikroreaktora se kontinuirano prenosi u daljnji mikroreaktor, u kojem se daljnjem mikroreaktoru dodaje najmanje jedan anhidrid kiseline i katalizator koji sadrži klorid.
HRP20231004TT 2018-03-15 2019-03-14 Postupak za pripremu n-alkil-nitratoetilnitramina HRP20231004T1 (hr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP18162059.2A EP3539943A1 (de) 2018-03-15 2018-03-15 Verfahren zur herstellung von n-alkyl-nitratoethylnitraminen
PCT/EP2019/056379 WO2019175296A1 (en) 2018-03-15 2019-03-14 Process for the preparation of n-alkyl-nitratoethylnitramines
EP19709964.1A EP3765440B1 (en) 2018-03-15 2019-03-14 Process for the preparation of n-alkyl-nitratoethylnitramines

Publications (1)

Publication Number Publication Date
HRP20231004T1 true HRP20231004T1 (hr) 2023-12-08

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Family Applications (1)

Application Number Title Priority Date Filing Date
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Country Status (15)

Country Link
US (1) US20190284131A1 (hr)
EP (2) EP3539943A1 (hr)
JP (1) JP7186792B2 (hr)
KR (1) KR102610017B1 (hr)
AU (1) AU2019233659B2 (hr)
CA (1) CA3092426C (hr)
DK (1) DK3765440T3 (hr)
ES (1) ES2960802T3 (hr)
FI (1) FI3765440T3 (hr)
HR (1) HRP20231004T1 (hr)
HU (1) HUE063118T2 (hr)
LT (1) LT3765440T (hr)
PL (1) PL3765440T3 (hr)
RS (1) RS64534B1 (hr)
WO (1) WO2019175296A1 (hr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111763154A (zh) * 2019-04-01 2020-10-13 南京理工大学 一种二乙醇硝胺二硝酸酯的合成方法
CN111559964B (zh) * 2020-05-19 2021-04-20 启东市新晨企业管理咨询有限公司 一种硝酸甘油的绿色制备方法
CN115784924A (zh) * 2022-11-29 2023-03-14 天元航材(营口)科技股份有限公司 一种连续法制备高纯度Bu-NENA的新工艺
GB202300801D0 (en) * 2023-01-19 2023-03-08 Bae Systems Plc Flow synthesis

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2678946A (en) * 1944-12-30 1954-05-18 Us Navy Process of preparing nitroxy alkyl nitramines
ES2194529T3 (es) 1999-10-14 2003-11-16 Dyno Nobel Asa Procedimiento de preparacion de un agente plastificante de alta energia.
US6262301B1 (en) 1999-10-15 2001-07-17 Dyno Asa Forsvarsprodukter Process of preparing a high-energy softening agent
ES2391601T3 (es) * 2007-12-20 2012-11-28 Dsm Fine Chemicals Austria Nfg Gmbh & Co Kg Formación de ésteres de nitrato en microreactores y milireactores usando una extracción de producto continua en un régimen de flujo turbulento
EP2172260A1 (en) 2008-09-29 2010-04-07 Corning Incorporated Multiple flow path microfluidic devices
CN101698646B (zh) * 2009-11-04 2012-10-03 西安万德能源化学股份有限公司 一种硝酸异辛酯的连续生产工艺
WO2013074326A1 (en) 2011-11-17 2013-05-23 Corning Incorporated Methods for asymmetric epoxidation using flow reactors

Also Published As

Publication number Publication date
CA3092426C (en) 2022-10-18
LT3765440T (lt) 2023-09-11
FI3765440T3 (fi) 2023-09-22
DK3765440T3 (da) 2023-10-09
RS64534B1 (sr) 2023-09-29
KR20200133759A (ko) 2020-11-30
CA3092426A1 (en) 2019-09-19
KR102610017B1 (ko) 2023-12-06
EP3765440B1 (en) 2023-07-19
JP2021515795A (ja) 2021-06-24
US20190284131A1 (en) 2019-09-19
JP7186792B2 (ja) 2022-12-09
AU2019233659B2 (en) 2021-04-29
EP3765440A1 (en) 2021-01-20
ES2960802T3 (es) 2024-03-06
PL3765440T3 (pl) 2023-12-27
EP3539943A1 (de) 2019-09-18
WO2019175296A1 (en) 2019-09-19
AU2019233659A1 (en) 2020-09-24
HUE063118T2 (hu) 2024-01-28

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