USRE30818E - Epichlorohydrin purification process - Google Patents
Epichlorohydrin purification process Download PDFInfo
- Publication number
- USRE30818E USRE30818E US06/152,245 US15224580A USRE30818E US RE30818 E USRE30818 E US RE30818E US 15224580 A US15224580 A US 15224580A US RE30818 E USRE30818 E US RE30818E
- Authority
- US
- United States
- Prior art keywords
- epichlorohydrin
- resin
- angstroms
- surface area
- iadd
- Prior art date
- 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.)
- Expired - Lifetime
Links
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 title claims abstract description 23
- 238000000746 purification Methods 0.000 title 1
- 239000011347 resin Substances 0.000 claims abstract description 39
- 229920005989 resin Polymers 0.000 claims abstract description 39
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical compound CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 claims abstract description 20
- -1 poly(t-butyl acrylate) Polymers 0.000 claims abstract description 16
- 239000011148 porous material Substances 0.000 claims abstract description 16
- 239000012535 impurity Substances 0.000 claims abstract description 8
- 238000000034 method Methods 0.000 claims description 8
- 239000003463 adsorbent Substances 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims 1
- 150000002924 oxiranes Chemical class 0.000 description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- CHRJZRDFSQHIFI-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;styrene Chemical compound C=CC1=CC=CC=C1.C=CC1=CC=CC=C1C=C CHRJZRDFSQHIFI-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 238000010923 batch production Methods 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/32—Separation; Purification
Definitions
- This invention relates to a method of purifying epichlorohydrin by contact with a polymeric adsorbent.
- .[.2,3-Butanedione is removed from product epichlorohydrin by contacting the epichlorohydrin with a macroreticular poly(t-butyl acrylate) adsorbent resin having a pore volume between about 0.48 and 0.57 ml/ml, an average pore diameter between about 80 and about 100 angstroms and a surface area between about 400 to about 500 square meters/gm.
- the poly(t-butyl acrylate) resin of this invention is superior to other resins such as styrene-divinylbenzene and to resins having differing surface areas and pore diameters..].
- .Iadd.2,3-Butanedione is removed from product epichlorohydrin by contacting the epichlorohydrin with an acrylic ester resin having a porosity of 0.55, a surface area of 450 m 2 /gm and an average pore diameter of 90 angstroms.
- the acrylic ester resin of this invention is superior to other resins such as styrene-divinylbenzene and to resins having differing surface areas and pore diameters. .Iaddend.
- the resins used in this invention are macroreticular poly(t-butyl acrylate) resins having a porosity (milliliter of pore/milliliter of dried resin) between about 0.48 and about 0.57 and preferably between about 0.50 to about 0.55; a surface area between about 400 to about 500 square meters per gram (of dried resin) and preferably between about 425 to about 475 square meters per gram; and an average pore diameter (of the dried resin) between about 80 to about 100 angstroms and preferably between about 85 to about 95 angstroms..].
- the resin used in this invention is an acrylic ester resin having a porosity of 0.55, a surface area of 450 m 2 /gm and an average pore diameter of 90 angstroms. .Iaddend.
- the resin is mixed with the epichlorohydrin and allowed to remain in contact therewith for about 0.01 to about 10 hours, preferably from about 0.1 to about 1 hours, and then separated by conventional means, e.g., filtration or centrifugation.
- the epichlorohydrin is preferably passed through a fixed bed of resin at liquid hourly space velocities ranging from about 0.1 to about 100 hours -1 , and preferably from about 0.5 to about 2.5 hours -1 .
- Tempertures of contact are not critical and are determined by the temperature stability of the resin and the freezing point of the epichlorohydrin. Temperatures are between about -25° C. and about 150° C.
- the resin of this invention significantly lowers the color index, removes substantially all of the 2,3-butanedione impurity without adversely affecting the epoxide value whereas other similar resins do not do so.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Epoxy Compounds (AREA)
Abstract
2,3-Butanedione impurity is removed from epichlorohydrin by contacting the impurity containing epichlorohydrin with .[.a macroreticular poly(t-butyl acrylate) resin .]. .Iadd.an acrylic ester resin .Iaddend.having a pore volume of about .[.0.5 .]. .Iadd.0.55 .Iaddend.ml/ml, an average pore diameter of about 90 angstroms and a surface area of about 450 m2 /gm.
Description
1. Field of the Invention
This invention relates to a method of purifying epichlorohydrin by contact with a polymeric adsorbent.
2. Background of the Invention
In the commercial production of epichlorohydrin, small amounts of impurities are frequently present in the product stream that will degrade the product, causing it to be off specification. One of these impurities is 2,3-butanedione which is a color body which when present in epichlorohydrin causes it to have an undesirable greenish tint. A simple and inexpensive process for removing the impurity from the epichlorohydrin product without causing a significant loss in the epoxide value of the product would be very desirable.
.[.2,3-Butanedione is removed from product epichlorohydrin by contacting the epichlorohydrin with a macroreticular poly(t-butyl acrylate) adsorbent resin having a pore volume between about 0.48 and 0.57 ml/ml, an average pore diameter between about 80 and about 100 angstroms and a surface area between about 400 to about 500 square meters/gm. The poly(t-butyl acrylate) resin of this invention is superior to other resins such as styrene-divinylbenzene and to resins having differing surface areas and pore diameters..].
.Iadd.2,3-Butanedione is removed from product epichlorohydrin by contacting the epichlorohydrin with an acrylic ester resin having a porosity of 0.55, a surface area of 450 m2 /gm and an average pore diameter of 90 angstroms. The acrylic ester resin of this invention is superior to other resins such as styrene-divinylbenzene and to resins having differing surface areas and pore diameters. .Iaddend.
.[.The resins used in this invention are macroreticular poly(t-butyl acrylate) resins having a porosity (milliliter of pore/milliliter of dried resin) between about 0.48 and about 0.57 and preferably between about 0.50 to about 0.55; a surface area between about 400 to about 500 square meters per gram (of dried resin) and preferably between about 425 to about 475 square meters per gram; and an average pore diameter (of the dried resin) between about 80 to about 100 angstroms and preferably between about 85 to about 95 angstroms..].
.Iadd.The resin used in this invention is an acrylic ester resin having a porosity of 0.55, a surface area of 450 m2 /gm and an average pore diameter of 90 angstroms. .Iaddend.
The .[.resins.]. .Iadd.resin .Iaddend.of the invention .[.are.]. .Iadd.is .Iaddend.contacted with the epichlorohydrin to be purified in either a batch process or a continuous or fixed-bed process. When a batch process is utilized, the resin is mixed with the epichlorohydrin and allowed to remain in contact therewith for about 0.01 to about 10 hours, preferably from about 0.1 to about 1 hours, and then separated by conventional means, e.g., filtration or centrifugation. In a continuous process the epichlorohydrin is preferably passed through a fixed bed of resin at liquid hourly space velocities ranging from about 0.1 to about 100 hours-1, and preferably from about 0.5 to about 2.5 hours-1. Tempertures of contact are not critical and are determined by the temperature stability of the resin and the freezing point of the epichlorohydrin. Temperatures are between about -25° C. and about 150° C.
The process of this invention will be further described by the following illustrative embodiments which are provided for illustration and are not to be construed as limiting the invention.
A series of resins (50 gram portions) shown in Table I were washed with 500 ml of deionized water, 250 ml of reagent grade methanol, 500 ml of reagent grade acetone and then dried in a vacuum at about 50° C. overnight.
TABLE I
__________________________________________________________________________
Avg
Surface Area
Pore Diameter
Source Type Porosity
m.sup.2 /gm
Angstroms
__________________________________________________________________________
Resin #1 Rohm and Haas XAD-4
Polystyrene
0.51 780 50
Resin #2 Rohm and Haas XAD-7
Acrylic ester
0.55 450 90
Resin #3 Rohm and Haas XAD-8
Acrylic ester
0.52 140 235
__________________________________________________________________________
A 29.5×7/16 inch glass column was packed (wet) with 20 cc of the appropriate resin prepared as above. Epichlorohydrin was allowed to pass through the resin by gravity at a liquid hourly space velocity of approximately 1-2 hours-1. After 20 ml of epichlorohydrin had passed through the column, the next 50 ml sample of epichlorohydrin was collected. The color index of the material was measured using ASTM D-1209-69. The concentration of 2,3-butanedione was measured with UV light absorptions in comparison with standard samples of 2,3-butanedione of known concentration. The epoxide values were measured by .[.NaI-isopropyl alcohol-acetic acid peroxide titration method.]. .Iadd.wet epoxide titrations (Anal. Chim. Acta, 31, 38 (1964).Iaddend.. The results are shown in Table II.
TABLE II
______________________________________
Color 2,3 Butanedione
Epoxide
Index ppm Value, % w
______________________________________
No resin used
40-50 25 99.0
Resin #1 25-30 20 98.9
Resin #2 15-20 0 99.1
Resin #3 25-30 15 98.9
______________________________________
Thus it can be seen that the resin of this invention (Resin #2) significantly lowers the color index, removes substantially all of the 2,3-butanedione impurity without adversely affecting the epoxide value whereas other similar resins do not do so.
Claims (1)
- between about 425 to about 475 square meters per gram..]. 3. The process of claim .[.1.]. .Iadd.4 .Iaddend.where the resin is contained in a fixed-bed and said epichlorohydrin is passed through said bed at a liquid hourly space velocity ranging between about 0.1 to about 100 hours-1. .Iadd. 4. The process of removing 2,3-butanedione impurity from epichlorohydrin which comprises contacting said epichlorohydrin with an acryclic ester resin having a porosity of 0.55, a surface area of 450 m2 /gm and an average pore diameter of 90 angstroms.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/152,245 USRE30818E (en) | 1978-01-30 | 1980-05-22 | Epichlorohydrin purification process |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/873,312 US4127593A (en) | 1978-01-30 | 1978-01-30 | Epichlorohydrin purification process |
| US06/152,245 USRE30818E (en) | 1978-01-30 | 1980-05-22 | Epichlorohydrin purification process |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US05/873,312 Reissue US4127593A (en) | 1978-01-30 | 1978-01-30 | Epichlorohydrin purification process |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| USRE30818E true USRE30818E (en) | 1981-12-08 |
Family
ID=26849379
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US06/152,245 Expired - Lifetime USRE30818E (en) | 1978-01-30 | 1980-05-22 | Epichlorohydrin purification process |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | USRE30818E (en) |
-
1980
- 1980-05-22 US US06/152,245 patent/USRE30818E/en not_active Expired - Lifetime
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