Editing Unsymmetrical dimethylhydrazine (section)

== Synthesis ==
In 1875, UDMH was first prepared by [[Emil Fischer]], who discovered and named the class of [[hydrazines]], by reducing [[N-Nitrosodimethylamine]] with zinc in boiling [[acetic acid]].<ref name=":0">{{cite journal |author=Horst Kunz |year=2002 |title=Emil Fischer – Unequalled Classicist, Master of Organic Chemistry Research, and Inspired Trailblazer of Biological Chemistry |journal=Angewandte Chemie International Edition |volume=41 |issue=23 |pages=4439–4451 |doi=10.1002/1521-3773(20021202)41:23<4439::AID-ANIE4439>3.0.CO;2-6 |pmid=12458504}}</ref><ref>{{Cite journal |last=Fischer |first=Emil |date=July 1875 |title=Ueber die Hydrazinverbindungen der Fettreihe |url=https://books.google.com/books?id=6JdDAQAAMAAJ&pg=PA111 |journal=Berichte der deutschen chemischen Gesellschaft |language=en |volume=8 |issue=2 |pages=1587–1590 |doi=10.1002/cber.187500802203 |issn=0365-9496}}</ref> Fischer's student [[Edward Renouf (chemist)|Edward Renouf]] later studied UDMH more extensively as part of his doctoral dissertation. Other historical lab routes include [[methylation]] of [[hydrazine]], reduction of nitrodimethylamine and [[amination]] of [[dimethylamine]] with aminopersulfuric acid.<ref>{{Cite web |title=Organic Syntheses Procedure |url=https://orgsyn.org/demo.aspx?prep=CV2P0211 |access-date=2024-11-02 |website=orgsyn.org |language=en}}</ref>

UDMH is produced industrially by two routes.<ref name="Ullmann">{{Ullmann|doi=10.1002/14356007.a13_177|title= Hydrazine|year= 2001|last1= Schirmann|first1= Jean-Pierre|last2= Bourdauducq|first2= Paul|isbn= 3-527-30673-0}}</ref> Based on the [[Olin Raschig process]], one method involves reaction of [[monochloramine]] with [[dimethylamine]] giving 1,1-dimethylhydrazinium chloride:
:(CH<sub>3</sub>)<sub>2</sub>NH + NH<sub>2</sub>Cl → (CH<sub>3</sub>)<sub>2</sub>NNH<sub>2</sub> ⋅ HCl

In the presence of suitable catalysts, acetylhydrazine can be N-dimethylated using [[formaldehyde]] and hydrogen to give the N,N-dimethyl-N'-acetylhydrazine, which can subsequently be hydrolyzed:
:CH<sub>3</sub>C(O)NHNH<sub>2</sub> + 2CH<sub>2</sub>O + 2H<sub>2</sub> → CH<sub>3</sub>C(O)NHN(CH<sub>3</sub>)<sub>2</sub> + 2H<sub>2</sub>O
:CH<sub>3</sub>C(O)NHN(CH<sub>3</sub>)<sub>2</sub> + H<sub>2</sub>O → CH<sub>3</sub>COOH + H<sub>2</sub>NN(CH<sub>3</sub>)<sub>2</sub>