University of Technology

chemical Engineering
Department

Branch:-Refinery.
Study:-morning.
Stage:- Third
Year:-2019-2020.

Design Equipment
(Vinyl Acetylene)
By:
1-‫ﻣﺮﯾﻢ ﺟﺎﺳﻢ‬
2-‫ﻣﻨﺘﻈﺮ ﻗﺎﺳﻢ‬

 Introduction
Vinylacetylene is the organic compound with the formula C4H4. The colourless gas
was once used in the polymer industry. It is composed of both alkyne and alkene
groups and is the simplest enyne.
organic compounds are generally any chemical compounds that contain carbon-
hydrogen bonds. Due to carbon's ability to catenate (form chains with other carbon
atoms), millions of organic compounds are known. The study of the properties,
reactions, and syntheses of organic compounds comprises the discipline known as
organic chemistry. For historical reasons, a few classes of carbon-containing
compounds (e.g., carbonate anion salts and cyanide salts), along with a handful of
other exceptions (e.g., carbon dioxide), are not classified as organic compounds and
are considered inorganic.
alkyne is an unsaturated hydrocarbon containing at least one carbon—carbon triple
bond.[1] The simplest acyclic alkynes with only one triple bond and no other
functional groups form a homologous series with the general chemical formula
CnH2n−2. Alkynes are traditionally known as acetylenes, although the name
acetylene also refers specifically to C2H2, known formally as ethyne using IUPAC
nomenclature. Like other hydrocarbons, alkynes are generally hydrophobic.
alkene is a hydrocarbon that contains a carbon–carbon double bond.[1] The term is
often used as synonym of olefin, that is, any hydrocarbon containing one or more
double bonds. Alkenes are generally colorless apolar compounds, somewhat similar
to alkanes but more reactive. The first few members of the series are gases or liquids
at room temperature. The simplest alkene, ethylene (C2H4) (or "ethene" in the
IUPAC nomenclature) is the organic compound produced on the largest scale
industrially.
An enyne is an organic compound consisting of a double bond (alkene) and triple
bond (alkyne). It is called a conjugated enyne when the double and triple bonds are
conjugated. The term is a contraction of the terms alkene and alkyne.
The simplest enyne is vinylacetylene.
Vinylacetylene is extremely dangerous because in high enough concentrations
(typically > 30 mole percent, but pressure dependent) it can auto-detonate (explode
without air being present) especially at elevated pressures, such as those seen in
chemical plants processing C4 hydrocarbons. An example of such an explosion
occurred at a Union Carbide plant in Texas City in 1969
Vinylacetylene was first synthesized by Hofmann elimination of the related
quaternary ammonium salt:
I2 → 2 [(CH3)3NH]I + HC≡C-CH=CH2[3NCH2CH=CHCH2N(CH3)3(CH3)]
It is usually synthesized by dehydrohalogenation of 1,3-dichloro-2-butene.[5] It also
.arises via the dimerization of acetylene or dehydrogenation of 1,3-butadiene
2

Physical Properties

 Application
At one time, chloroprene (2-chloro-1,3-butadiene), an industrially important
monomer, was produced via the intermediacy of vinyl acetylene. In this process,
acetylene is dimerized to give vinyl acetylene, which is then combined with hydrogen
chloride to give 4-chloro-1,2-butadiene via 1,4-addition. This allene derivative which,
in the presence of cuprous chloride, rearranges to 2-chloro-1,3-butadiene
H2C=CH-C≡CH + HCl → H2ClC-CH=C=CH2
H2ClC-CH=C=CH2 → H2C=CH-CCl=CH2

 Calculation
M.wt=52.076 g/mol
Critical pressure (pc) =49.6 bar
Critical Temperature (Tc) =455 k
Heat of vapour (HVAP) =24.493 J/Mol
Gas Heat capacity (CP)
Cp = CPVAPA + (CPVAPB) *T + (CPVAPC) *T **2 +
(CPVAPD) *T **3
Cp = (0.757) + (28.704 × 10−2) * 403)
(−2.265 × 10−4)*(403)*2 + (74.609 × 10−9)*(403)*3
Cp = 99937.38 J/Mol

LOG[viscosity] = [VISA] * [(1/T) - (1/VISB)]

Tk=20+273
Tk=293 k
Log= (0)*[(1/293) -(1/0)]
Log =0

(‎

 PM
ρ=
RT
Tk = 50 + 273 = 323k
R=8.31 J/mol
M.wt= 52.06
P=5552.58 kpa
(5552.58)kpa × (52.076)g/mol
ρ=
(8.31)J/mol × (323)k
ρ = 107.7kg/m 3

1/Q Q1 : You have mercury at 60 C, check the proper

materials that are resistant to acetone corrosion.

-Material that are resistant to corrosion at 60c are

[Aluminium (a) ,Aluminium Bronze, Brass (b),Cast Iron (c)
,Copper, Gunmetal and Bronze (d), High Si Iron (14% Si)
(c) ,Lead ,Nickel (cast) ,ckel-Copper Alloys (e) ,Ni Resist
(High Ni Iron) (c) ,Platinum , Silver ,Stainless Steel 18/8
(f),Molybdenum Stainless Steel 18/8 (f) ,Austenitic Ferricr,
Stainless Steel (x) ,Tantalum ,Tin (g) ,Titanium ,Zirconium]

 Reference
1-volume 6 :- Q1/ page (918, 919)
Q2/page(937, 942 , 943)

2-https://en.m.wikipedia.org/wiki/Vinylacetylene

3-https://www.chemeo.com/cid/38-727-3/
Cyclobutadiene.pdf

4-https://www.airgas.com/msds/001116.pdf