Chemical Production Processes and Systems
Chemical production processes are provided that include reacting a metal comprising olefin to form a conjugated olefin; reacting a heterohalogenated olefin to form a conjugated olefin; reacting a halogenated alkane to form a conjugated olefin; and/or reacting a hydrohalogenated olefin to form a conjugated olefin. Chemical production systems are also provided that can include: a first reactant reservoir configured to house a perhalogenated olefin; a second reactant reservoir configured to house a catalyst mixture; a first reactor coupled to both the first and second reservoirs, the first reactor configured to house a metal-comprising mixture and receive both the perhalogenated olefin form the first reactant reservoir and the reactant mixture from the second reactant reservoir; and a product collection reservoir coupled to the first reactor and configured to house a conjugated olefin.
1 . A chemical production process comprising reacting a metal comprising olefin to form a conjugated olefin.
2 . The chemical production process of claim 1 wherein the metal comprising olefin comprises at least one element from groups 11 or 12 of the periodic table of elements.
3 . The chemical production process of claim 2 wherein the one element is Zn.
4 . The chemical production process of claim 1 wherein the metal comprising olefin comprises one or more of F, Cl, Br, and I.
5 . The chemical production process of claim 4 wherein the metal comprising olefin is heterohalogenated.
6 . The chemical production process of claim 4 wherein the metal comprising olefin is perhalogenated.
7 . The chemical production process of claim 1 wherein the metal comprising olefin is a C-2 olefin.
8 . The chemical production process of claim 7 wherein the metal comprising olefin comprises both F and Br.
9 . The chemical production process of claim 7 wherein the metal comprising olefin comprises F, Br, and Zn.
10 . The chemical production process of claim 7 wherein the metal comprising olefin is
11 . The chemical production process of claim 1 wherein the conjugated olefin comprises one or more of F, Cl, Br, and I.
12 . The chemical production process of claim 1 wherein the conjugated olefin is perhalogenated.
13 . The chemical production process of claim 1 wherein the conjugated olefin is homohalogenated.
14 . The chemical production process of claim 1 wherein the conjugated olefin is a C-4 olefin.
15 . The chemical production process of claim 14 wherein the C-4 olefin is perhalogenated with F.
16 . The chemical production process of claim 1 wherein the conjugated olefin is
17 . The chemical production process of claim 1 wherein the reacting comprises exposing the metal-comprising olefin to a reactant mixture to form the conjugated olefin.
18 . The chemical production process of claim 17 wherein the reactant mixture comprises one or more of Fe, Cu, Na, Mg, Ni, and Ag.
19 . The chemical production process of claim 17 wherein the reactant mixture comprises a metal-halide composition.
20 . The chemical production process of claim 19 wherein the metal halide composition comprises one or more of Fe, Cu, Na, Mg, Ni, Ag, F, Cl, Br, and I.
21 . The chemical production process of claim 17 wherein the reactant mixture comprises a polar aprotic solvent.
22 . The chemical production process of claim 17 wherein the reactant mixture comprises tetrahydrofuran.
23 . The chemical production process of claim 17 wherein the exposing comprises:
providing the metal comprising olefin to within a reactor; and
providing the reactant mixture to within the reactor, wherein a temperature of the contents of the reactor is maintained during the providing of the catalyst mixture.
24 . The chemical production process of claim 23 wherein:
the metal comprising olefin comprises
the reactant mixture comprises FeCl 3 ; and
the temperature is less than about 70° C.
25 . The chemical production process of claim 23 further comprising removing the conjugated olefin from the reactor.
26 . The chemical production process of claim 25 wherein the removing comprises increasing the maintained temperature of the contents of the reactor.
27 . The chemical production process of claim 26 wherein the increasing comprises at least about a 15% increase in the maintained temperature.
28 . The chemical production process of claim 27 wherein the maintained temperature is about 70° C. and the increasing comprises increasing the temperature to about 90° C.
29 . The chemical production process of claim 25 wherein:
the metal comprising olefin comprises
the reactant mixture comprises FeCl 3 ;
the temperature is less than about 70° C.;
the conjugated olefin comprises and
and
the increased temperature is greater than about 80° C.
30 . The chemical production process of claim 25 further comprising purifying the conjugated olefin.
31 . The chemical production process of claim 30 wherein the purifying comprises one or both of distilling and drying the conjugated olefin.
32 . The chemical production process of claim 31 wherein the distilling comprises:
providing a product mixture comprising the conjugated olefin and by products to a distillation apparatus;
converting at least a portion of the mixture to the gas phase, the portion of the mixture comprising at least a portion of the conjugated olefin; and
recovering a distillate comprising the portion of the conjugated olefin, the distillate comprising less by-products than the product mixture.
33 . The chemical production process of claim 31 wherein the drying comprises exposing a product mixture comprising the conjugated olefin to one or both of a 3 Å absorbent and a 13× molecular sieve.
34 . The chemical production process of claim 33 wherein the product mixture is in the liquid phase during the exposing.
35 . A chemical production process comprising reacting a heterohalogenated olefin to form a conjugated olefin.
36 . The chemical production process of claim 35 wherein the heterohalogenated olefin is a C-2 olefin.
37 . The chemical production process of claim 35 wherein the heterohalogenated olefin comprises F and one or more of Cl, Br, and I.
38 . The chemical production process of claim 35 wherein the heterohalogenated olefin is
39 . The chemical production process of claim 36 wherein the reacting comprises:
providing a reactor, the reactor being configured to expose a metal comprising mixture to the heterohalogenated olefin;
providing the metal comprising mixture to within the reactor; and
exposing the metal-comprising mixture to the heterohalogenated olefin to form a metal comprising olefin.
40 . The chemical production process of claim 39 wherein the metal comprising mixture comprises at least one or more elements from groups 1, 2, 4, 8, 11, 12, and 14 of the periodic table of elements.
41 . The chemical production process of claim 39 wherein the metal comprising mixture comprises Zn.
42 . The chemical production process of claim 39 wherein the metal comprising mixture comprises a polar aprotic solvent.
43 . The chemical production process of claim 39 wherein the metal comprising mixture comprises tetrahydrofuran.
44 . The chemical production process of claim 39 wherein the providing the metal comprising mixture to within the reactor comprises:
providing a composition comprising a polar aprotic solvent and tetrahydrofuran to the reactor;
providing a metal to the reactor, the metal and composition forming the metal comprising mixture; and
heating the mixture to a temperature of from about 17° C. to about 120° C.
45 . The chemical production process of claim 44 wherein the heating further comprises maintaining the mixture at a temperature of from about 60° C. to about 110° C.
46 . The chemical production process of claim 39 further comprising conjugating the metal comprising olefin to form the conjugated olefin.
47 . The chemical production process of claim 46 wherein:
the heterohalogenated olefin is
the reactant mixture is Fe;
the metal-comprising mixture is Zn;
the metal comprising olefin is
and
the conjugated olefin is
48 . A chemical production process comprising reacting a halogenated alkane to form a conjugated olefin.
49 . The chemical production process of claim 48 wherein the halogenated alkane comprises one or more of F, Cl, Br, and I.
50 . The chemical production process of claim 48 wherein the halogenated alkane is a C-2 alkane.
51 . The chemical production process of claim 48 wherein the halogenated alkane is heterohalogenated.
52 . The chemical production process of claim 48 wherein the halogenated alkane is C 2 HF 3 Br 2 .
53 . The chemical production process of claim 52 wherein the halogenated alkane is
54 . The chemical production process of claim 48 wherein the reacting comprises:
reacting the halogenated alkane to form a heterohalogenated olefin; and
reacting the heterohalogenated olefin to from the conjugated olefin.
55 . The chemical production process of claim 54 wherein the reacting the halogenated alkane to form the heterohalogenated olefin comprises:
providing a reactor configured to expose the halogenated olefin to a reducing reagent mixture;
providing the reducing reagent mixture to within the reactor;
exposing the halogenated olefin to the reducing regent mixture to form the heterohalogenated olefin.
56 . The chemical production process of claim 55 wherein the reactor comprises a nickel alloy.
57 . The chemical production process of claim 55 wherein the reactor is glass lined.
58 . The chemical production process of claim 55 wherein the reducing-reagent mixture comprises a base.
59 . The chemical production process of claim 55 wherein the reducing reagent mixture comprises KOH and water.
60 . The chemical production process of claim 55 wherein the reducing reagent mixture comprises 40% (wt./wt.) KOH.
61 . A chemical production process comprising reacting a hydrohalogenated olefin to form a conjugated olefin.
62 . The chemical production process of claim 61 wherein the hydrohalogenated olefin comprises one or more of F, Cl, Br, and I.
63 . The chemical production process of claim 61 wherein the hydrohalogenated olefin is a C-2 olefin.
64 . The chemical production process of claim 61 wherein the hydrohalogenated olefin is C 2 HF 3 .
65 . The chemical production process of claim 61 wherein the hydrohalogenated olefin is
66 . The chemical production process of claim 61 wherein the reacting comprises:
reacting the hydrohalogenated olefin to form a halogenated alkane; and
reacting the halogenated alkane to form the conjugated olefin.
67 . The chemical production process of claim 61 wherein the reacting the hydrohalogenated olefin to form the halogenated alkane comprises:
providing a reactor configured to expose the hydrohalogenated olefin to a halogenating reagent;
providing the hydrohalogenated olefin to within a reactor; and
exposing the hydrohalogenated olefin to the halogenating reagent to form the halogenated alkane.
68 . The chemical production process of claim 67 wherein halogenating reagent comprises one or more of F, Cl, Br, and I.
69 . The chemical production process of claim 67 wherein:
the hydrohalogenated olefin is
the halogenated reagent is Br 2 ; and
the halogenated alkane is
70 . A chemical production process comprising:
providing a heterohalogenated olefin to within a reactor;
providing a reducing agent to within the reactor; and
reacting the olefin with the reducing agent within the reactor, at least the olefin being in the liquid phase during the reacting.
71 . The chemical production process of claim 70 further comprising providing a catalyst composition to the reactor.
72 . The chemical production process of claim 71 wherein the catalyst composition comprises one or both of Pd and C.
73 . The chemical production process of claim 70 further comprising providing an organic media to the reactor.
74 . The chemical production process of claim 73 wherein the organic media comprises as solvent.
75 . The chemical production process of claim 73 wherein the organic media comprises methanol.
76 . The chemical production process of claim 70 further comprising:
providing a catalyst composition to the reactor; and
providing an organic media to the reactor.
77 . The chemical production process of claim 76 wherein:
heterohalogenated olefin is C 2 CIF 3 ;
the reducing agent comprises H;
the catalyst composition comprises one or both of Pd and C; and
the organic media comprises methanol.
78 . A production system comprising:
a first reactant reservoir configured to house a perhalogenated olefin;
a second reactant reservoir configured to house a catalyst mixture;
a first reactor coupled to both the first and second reservoirs, the first reactor configured to house a metal-comprising mixture and receive both the perhalogenated olefin from the first reactant reservoir and the reactant mixture from the second reactant reservoir; and
a product collection reservoir coupled to the first reactor and configured to house a conjugated olefin.
79 . The production system of claim 78 wherein:
the perhalogenated olefin is
the reactant mixture is Fe;
the metal comprising mixture is Zn; and
the conjugated olefin is
80 . The production system of claim 78 further comprising a second reactor coupled to both the product reservoir and the first reactant reservoir, the second reactor configured to receive at least one by-product from the product reservoir and react the by-product to form the perhalogenated olefin.
81 . The production system of claim 80 wherein second reactor comprises both a third and a fourth reactor, the third reactor being coupled to the fourth reactor, wherein:
the third reactor is configured to react a hydrohalogenated olefin to form a halogenated alkane; and
the fourth reactor is configured to react the halogenated alkane to form a heterohalogenated olefin, wherein the by-product is one or both of the hydrohalogenated olefin and the halogenated alkane.
82 . The production system of claim 81 wherein:
the hydrohalogenated olefin is
and
the halogenated alkane is