CN114436784A - Cresol antioxidant color fixing production method and system - Google Patents
Cresol antioxidant color fixing production method and system Download PDFInfo
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- CN114436784A CN114436784A CN202210100082.1A CN202210100082A CN114436784A CN 114436784 A CN114436784 A CN 114436784A CN 202210100082 A CN202210100082 A CN 202210100082A CN 114436784 A CN114436784 A CN 114436784A
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- cresol
- hydrazine hydrate
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- sodium sulfate
- anhydrous sodium
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- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 title claims abstract description 162
- 229930003836 cresol Natural products 0.000 title claims abstract description 162
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 20
- 239000003963 antioxidant agent Substances 0.000 title claims abstract description 16
- 230000003078 antioxidant effect Effects 0.000 title claims abstract description 16
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 claims abstract description 70
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims abstract description 70
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 66
- 238000010992 reflux Methods 0.000 claims abstract description 9
- 230000003647 oxidation Effects 0.000 claims abstract description 7
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 46
- 239000000126 substance Substances 0.000 abstract description 22
- 238000000034 method Methods 0.000 abstract description 17
- 230000008569 process Effects 0.000 abstract description 12
- 238000003860 storage Methods 0.000 abstract description 9
- 230000009286 beneficial effect Effects 0.000 abstract description 6
- 230000002035 prolonged effect Effects 0.000 abstract description 6
- 238000002474 experimental method Methods 0.000 abstract description 5
- 230000002401 inhibitory effect Effects 0.000 abstract description 4
- 238000000926 separation method Methods 0.000 abstract description 2
- 230000000052 comparative effect Effects 0.000 description 19
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 14
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 12
- 150000003739 xylenols Chemical class 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 5
- ZRXYTQOLAOPNQL-UHFFFAOYSA-N 2,3-dimethylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1C ZRXYTQOLAOPNQL-UHFFFAOYSA-N 0.000 description 4
- -1 alkali metal salts Chemical class 0.000 description 4
- 230000014759 maintenance of location Effects 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000004321 preservation Methods 0.000 description 4
- 230000003064 anti-oxidating effect Effects 0.000 description 3
- 239000003638 chemical reducing agent Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000002893 slag Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- 230000000087 stabilizing effect Effects 0.000 description 3
- 230000002195 synergetic effect Effects 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- XRUGBBIQLIVCSI-UHFFFAOYSA-N 2,3,4-trimethylphenol Chemical compound CC1=CC=C(O)C(C)=C1C XRUGBBIQLIVCSI-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 241001106041 Lycium Species 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical class OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000012824 chemical production Methods 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 239000011280 coal tar Substances 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 239000013068 control sample Substances 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- WBZKQQHYRPRKNJ-UHFFFAOYSA-N disulfurous acid Chemical class OS(=O)S(O)(=O)=O WBZKQQHYRPRKNJ-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011810 insulating material Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229910021655 trace metal ion Inorganic materials 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/88—Use of additives, e.g. for stabilisation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
- B01D3/14—Fractional distillation or use of a fractionation or rectification column
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
- C07C37/74—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by distillation
Abstract
The invention provides a cresol antioxidant color fixing production method and system, and belongs to the technical field of chemical separation. Adding hydrazine hydrate accounting for 0.01-0.03% of the mass of the cresol into the cresol fraction at the temperature of 50-90 ℃, on one hand, the addition of the hydrazine hydrate is beneficial to inhibiting the oxidation process of the cresol, so that the problem of darkening of the cresol in the storage process is improved, and the additional value of the cresol is improved. Experiments show that the time for changing the color of cresol from light yellow to dark brown is prolonged by 30-60 days under the normal-temperature and dark environment by adding hydrazine hydrate into cresol fraction at the temperature of 50-90 ℃. On the other hand, a small amount of hydrazine hydrate enters the mixed phenol rectifying tower in a cresol reflux mode, so that the generation of heavy components in the tower bottom of the mixed phenol rectifying tower is reduced, and the yield of light phenol is improved.
Description
Technical Field
The invention belongs to the technical field of chemical separation, and particularly relates to a cresol antioxidant color fixing production method and system.
Background
Phenol products, particularly cresol and xylenol, are important raw materials for chemical production and are widely applied to preparation of insulating materials, bactericides, spices, fuels, pesticides and the like. As cresol and xylenol are sensitive to oxygen and unstable in property, during storage, the cresol and xylenol are easy to change color due to oxidation when exposed to light or air, so that the color of the phenolic product is deepened and even blackened, and the appearance and the quality of the phenolic product are influenced.
In the prior art, much research is put into stabilizing the appearance and color of phenol products, and the phenol products separated by a coal chemical method are generally stabilized by technical methods of improving the product purity, cutting off an oxygen source, removing colloid, trace metal ions and moisture, keeping out of the sun and the like. However, the above method is not only complicated in process, but also short in color retention time of phenolic appearance.
The color stabilizer and the stabilizing technology are proved to be methods capable of effectively prolonging the retention time of the appearance color of the phenolic products, and mainly organic or inorganic compounds are added into the phenolic products so as to play a role in stabilizing the color. For example, chinese patent No. 201810362209.0 discloses a composite color stabilizer for inhibiting the discoloration of alkylphenol, which comprises a reducing agent and a synergistic antioxidant, wherein the reducing agent is alkali metal salts of sulfurous acid and pyrosulfurous acid, and the synergistic antioxidant is one or more of citric acid, tartaric acid, lycium acid or their salts. Although the composite color stabilizer disclosed in the above patent claims to prolong the retention time of the apparent color of the phenolic product (p-cresol and m-cresol), the reducing agent and the synergistic antioxidant both adopt solid substances, and solid particles settle along with the prolonging of the storage time, so that the solid particles cannot be or are difficult to be uniformly distributed in the product, and therefore, the effect of prolonging the retention time of the apparent color of the phenolic product in practical application is limited.
Disclosure of Invention
Based on the above, the invention provides a cresol antioxidant color fixing production method, which aims to solve the technical problem that the color of a phenol product is easy to deepen in the storage process in the prior art.
The invention also provides a cresol antioxidant color fixing production system.
The technical scheme for solving the technical problems is as follows:
a production method of cresol antioxidation color fixation is to add hydrazine hydrate into cresol fraction with the temperature of 50-90 ℃, wherein the addition amount of the hydrazine hydrate is 0.01-0.03 percent of the mass of the cresol.
Preferably, hydrazine hydrate is added in an amount of 0.01% by mass of cresol.
Preferably, anhydrous sodium sulfate is also added into the cresol fraction with the temperature of 50-90 ℃, and the addition amount of the anhydrous sodium sulfate is 0.8-1 time of the mass of hydrazine hydrate.
Preferably, the addition amount of anhydrous sodium sulfate is 0.8 times of the mass of hydrazine hydrate.
Preferably, the cresol is prepared by rectifying mixed phenol.
A cresol antioxidation color fixing production system comprises a mixed phenol rectifying device, wherein the mixed phenol rectifying device comprises a mixed phenol rectifying tower, a cresol condenser, a cresol fraction tank and a cresol reflux pump which are arranged at a material ejection end of the mixed phenol rectifying tower, and a tower kettle discharge pump and a heavy component tank which are arranged at a tower bottom discharge end of the mixed phenol rectifying tower;
the device comprises a cresol distillate tank, and is characterized in that a hydrazine hydrate trough is arranged on the cresol distillate tank and communicated with the cresol distillate tank, a cresol flow sensor is arranged at the feed end of the cresol distillate tank, a first flow control valve is arranged at the discharge end of the hydrazine hydrate trough, and the cresol flow sensor is electrically connected with the first flow control valve.
Preferably, the cresol distillate tank is further provided with an anhydrous sodium sulfate trough, and the anhydrous sodium sulfate trough is communicated with the cresol distillate tank.
Preferably, a cresol feeding pipe is arranged on the anhydrous sodium sulfate trough and connected with the discharge end of the cresol distillate tank; and a second flow control valve is arranged at the discharge end of the anhydrous sodium sulfate trough and is electrically connected with the first flow control valve.
Compared with the prior art, the invention has at least the following advantages:
adding hydrazine hydrate accounting for 0.01-0.03 percent of the mass of the cresol into the cresol fraction at the temperature of 50-90 ℃, on one hand, the addition of the hydrazine hydrate is beneficial to inhibiting the oxidation process of the cresol, thereby being beneficial to improving the problem of darkening of the cresol in the storage process and improving the added value of the cresol. Experiments show that the time for changing the color of cresol from light yellow to dark brown is prolonged by 30-60 days under the environment of normal temperature and dark place by adding hydrazine hydrate into cresol fraction with the temperature of 50-90 ℃. On the other hand, a small amount of hydrazine hydrate enters the mixed phenol rectifying tower in a cresol reflux mode, so that the generation of heavy components in a tower kettle of the mixed phenol rectifying tower is reduced, and the yield of light phenol is improved.
Drawings
Fig. 1 is a schematic view of an apparatus flow of a cresol antioxidant fixation production system of an embodiment.
In the figure: the system comprises a mixed phenol rectifying device 10, a mixed phenol rectifying tower 100, a cresol condenser 200, a cresol distillate tank 300, a hydrazine hydrate tank 310, a first flow control valve 311, a cresol flow sensor 320, an anhydrous sodium sulfate tank 330, a cresol feed pipe 331, a second flow control valve 332, a cresol reflux pump 400, a tower bottom discharge pump 500 and a heavy component tank 600.
Detailed Description
It should be noted that the embodiments and features of the embodiments may be combined with each other without conflict. The technical solutions of the present invention will be further described below with reference to the accompanying drawings of the embodiments of the present invention, and the present invention is not limited to the following specific embodiments.
It should be understood that the same or similar reference numerals in the drawings of the embodiments correspond to the same or similar parts. In the description of the present invention, it should be understood that if there are terms such as "upper", "lower", "front", "rear", "left", "right", "top", "bottom", etc., indicating orientations or positional relationships based on the orientations or positional relationships shown in the drawings, it is only for convenience of description and simplicity of description, but does not indicate or imply that the equipment or elements referred to must have a specific orientation, be constructed in a specific orientation, and be operated, and therefore, the terms describing the positional relationships in the drawings are only used for illustrative purposes and are not to be construed as limiting the patent, and the specific meanings of the terms will be understood by those skilled in the art according to specific situations.
In a specific embodiment, the production method of cresol antioxidation color fixation is that hydrazine hydrate is added into cresol fraction with the temperature of 50-90 ℃, and the addition amount of the hydrazine hydrate is 0.01-0.03 percent of the mass of cresol. Preferably, hydrazine hydrate is added in an amount of 0.01% by mass of cresol.
Adding hydrazine hydrate accounting for 0.01-0.03 percent of the mass of the cresol into the cresol fraction at the temperature of 50-90 ℃, on one hand, the addition of the hydrazine hydrate is beneficial to inhibiting the oxidation process of the cresol, thereby being beneficial to improving the problem of darkening of the cresol in the storage process and improving the added value of the cresol. Experiments show that the time for changing the color of cresol from light yellow to dark brown is prolonged by 30-60 days under the environment of normal temperature and dark place by adding hydrazine hydrate into cresol fraction with the temperature of 50-90 ℃.
In the above embodiment, the amount of hydrazine hydrate added is calculated as pure hydrazine hydrate. However, in order to facilitate procurement and cost reduction, it is preferable in the present invention to use a hydrazine hydrate solution having a mass concentration of 80% in order to facilitate addition of hydrazine hydrate to the cresol fraction.
In a preferred embodiment, in order to further prolong the time of the cresol color changing from light yellow to dark brown, anhydrous sodium sulfate is added into the cresol fraction with the temperature of 50-90 ℃, and the adding amount of the anhydrous sodium sulfate is 0.8-1 time of the mass of hydrazine hydrate. Preferably, the addition amount of anhydrous sodium sulfate is 0.8 times of the mass of hydrazine hydrate. Experiments show that the time for changing the color of cresol from light yellow to dark brown is prolonged by 90-120 days under the normal-temperature and dark environment by adding hydrazine hydrate and anhydrous sodium sulfate into cresol fraction at the temperature of 50-90 ℃.
In the above embodiment, the anhydrous sodium sulfate may be added to the hydrazine hydrate solution, together with the hydrazine hydrate, or may be added separately. In a preferred embodiment, anhydrous sodium sulfate is first dispersed in cresol to form a cresol-anhydrous sodium sulfate mixed suspension, which is then added to a cresol fraction at a temperature of from 50 ℃ to 90 ℃.
In one embodiment, the cresol is prepared by rectifying a mixed phenol. At the moment, in the cresol production process, a small amount of hydrazine hydrate enters the mixed phenol rectifying tower in a cresol reflux mode, so that the generation of heavy components in the tower bottom of the mixed phenol rectifying tower is reduced, and the yield of light phenol is improved.
In order to implement the above method, referring to fig. 1, in another embodiment of the present invention, a cresol antioxidant color fixing production system is provided, which includes a mixed phenol rectification apparatus 10, where the mixed phenol rectification apparatus 10 includes a mixed phenol rectification tower 100, a cresol condenser 200, a cresol fraction tank 300, and a cresol reflux pump 400, which are disposed at a discharge end of a tower top of the mixed phenol rectification tower 100, and a tower bottom discharge pump 500 and a heavy component tank 600, which are disposed at a discharge end of a tower bottom of the mixed phenol rectification tower 100. The cresol distillate tank 300 is provided with a hydrazine hydrate tank 310, the hydrazine hydrate tank 310 is communicated with the cresol distillate tank 300, a cresol flow sensor 320 is arranged at the feed end of the cresol distillate tank 300, a first flow control valve 311 is arranged at the discharge end of the hydrazine hydrate tank 310, and the cresol flow sensor 320 is electrically connected with the first flow control valve 311.
According to the feeding flow of the cresol fraction of the cresol flow sensor 320, the opening degree of the first flow control valve 311 is regulated, and the adding amount of hydrazine hydrate is controlled. Meanwhile, hydrazine hydrate is added to the cresol cut tank 300, and then returned to the mixed phenol rectifying tower 100 through the cresol reflux pump 400. A small amount of hydrazine hydrate enters the mixed phenol rectifying tower 100 in a cresol reflux mode, so that the generation of heavy components in the tower bottom of the mixed phenol rectifying tower 100 is reduced, and the yield of light phenol is improved.
In one embodiment, the cresol fraction tank 300 is further provided with an anhydrous sodium sulfate tank 330, and the anhydrous sodium sulfate tank 330 is communicated with the cresol fraction tank 300 so as to add anhydrous sodium sulfate into the cresol fraction tank 300.
Further, a cresol feeding pipe 331 is arranged on the anhydrous sodium sulfate trough 330, and the cresol feeding pipe 331 is connected with the discharge end of the cresol fraction tank 300. The discharge end of the anhydrous sodium sulfate trough 330 is provided with a second flow control valve 332, and the second flow control valve 332 is electrically connected with the first flow control valve 311. According to the flow of the first flow control valve 311, the opening degree of the second flow control valve 332 is regulated to control the addition amount of the anhydrous sodium sulfate.
The technical scheme and technical effects of the present invention are further described below by specific experimental examples.
It should be noted that, in the following experimental examples, crude phenol produced by Ningxia coal tar deep processing manufacturers was selected and subjected to distillation and weight removal to prepare mixed phenol, and the given substance content in the obtained mixed phenol is shown in Table 1.
TABLE 1 content of each substance in phenol mixture
| Substance(s) | Phenol and its preparation | Ortho-cresol | M-cresol + p-cresol | Dimethyl phenol |
| The content wt% | 24.62％ | 16.91％ | 32.23％ | 12.35％ |
Comparative example 1
And (3) the mixed phenol enters the mixed phenol rectifying tower 100, and phenol, o-cresol, m-cresol and xylenol are separated under the process condition, wherein hydrazine hydrate and anhydrous sodium sulfate are not added into the cresol fraction tank 300 in the comparative example I. In comparative example one, the yields of the respective substances isolated (mass of the respective substances isolated/total amount of the feed) are shown in table 2, and the contents of the key components in the heavy components isolated are shown in table 3.
TABLE 2 yields of the substances
| Substance(s) | Phenol and its preparation | Ortho-cresol | M-cresol + p-cresol | Dimethyl phenol |
| The content wt% | 24.57％ | 16.90％ | 32.20％ | 12.30％ |
TABLE 3 composition of the heavies
| Substance(s) | Slag | Naphthalene | Ethyl phenol | Trimethylphenol |
| The content is wt% | 85.21％ | 3.58％ | 7.15％ | 4.00％ |
Experimental example I
And (3) the mixed phenol enters the mixed phenol rectifying tower 100, phenol, o-cresol, m-cresol and xylenol are separated under the process condition, and hydrazine hydrate with the mass fraction of 80% is added into the cresol fraction tank 300 in the rectifying process, wherein the adding amount of the hydrazine hydrate is 0.03% of that of the cresol fraction. In the first experimental example, the yields of the respective substances isolated (mass of the respective substances isolated/total amount of the feed) are shown in table 4, and the contents of the key components in the heavy components isolated are shown in table 5.
TABLE 4 yields of the substances
| Substance(s) | Phenol and its preparation | Ortho-cresol | M-cresol + p-cresol | Dimethyl phenol |
| The content wt% | 24.60％ | 16.90％ | 32.21％ | 12.32％ |
TABLE 5 composition of the heavies
| Substance(s) | Slag | Naphthalene | Ethyl phenol | Trimethylphenol |
| The content wt% | 84.52％ | 3.79％ | 7.45％ | 4.18％ |
Experimental example two
And (2) the mixed phenol enters the mixed phenol rectifying tower 100, and phenol, o-cresol, m-cresol and xylenol are separated under the process condition, in the second experimental example, hydrazine hydrate and anhydrous sodium sulfate with the mass fraction of 80% are added into the cresol fraction tank 300, the adding amount of the hydrazine hydrate is 0.03% of that of the cresol fraction, and the adding amount of the anhydrous sodium sulfate is 0.8 times of that of the hydrazine hydrate. In comparative example one, the yields of the respective substances isolated (mass of the respective substances isolated/total amount of the feed) are shown in table 6, and the contents of the key components in the heavy components isolated are shown in table 7.
TABLE 6 yields of the substances
| Substance(s) | Phenol and its preparation | Ortho-cresol | M-cresol + p-cresol | Dimethyl phenol |
| The content wt% | 24.58％ | 16.91％ | 32.20％ | 12.31％ |
TABLE 7 composition of the heavies
| Substance(s) | Slag | Naphthalene | Ethyl phenol | Trimethylphenol |
| The content wt% | 84.61％ | 3.75％ | 7.41％ | 4.21％ |
By combining the comparative example I, the experimental example I and the experimental example II, the addition of the hydrazine hydrate is beneficial to reducing the generation of heavy components in the tower bottom of the mixed phenol rectifying tower and improving the yield of the light phenol.
Experimental examples storage of Trimethylphenol
The following control group samples were set up for storage experiments:
D1. cresol produced in comparative example one;
D2. in the cresol produced in comparative example one, hydrazine hydrate was added at a mass concentration of 80% at normal temperature, and the amount (absolute mass) of hydrazine hydrate added was 0.01% of the mass of cresol.
D3. In the cresol produced in comparative example one, hydrazine hydrate was added at a mass concentration of 80% at normal temperature, and the amount (absolute mass) of hydrazine hydrate added was 0.03% of the mass of cresol.
D4. The cresol produced in comparative example one was added with anhydrous sodium sulfate at room temperature in an amount of 0.008% by mass based on the cresol.
D5. The cresol produced in comparative example one was added with anhydrous sodium sulfate in an amount of 0.01% by mass of the cresol at normal temperature.
D6. In the cresol produced in comparative example one, hydrazine hydrate and anhydrous sodium sulfate were added at a mass concentration of 80% at normal temperature, the amount (absolute mass) of hydrazine hydrate was 0.01% by mass of the cresol, and the amount of anhydrous sodium sulfate was 0.008% by mass of the cresol.
D7. In the cresol produced in comparative example one, hydrazine hydrate and anhydrous sodium sulfate were added at a mass concentration of 80% at normal temperature, the amount of hydrazine hydrate added (absolute mass) was 0.03% by mass of the cresol, and the amount of anhydrous sodium sulfate added was 0.03% by mass of the cresol.
D8. The cresol produced in comparative example one was heated to 50 c, hydrazine hydrate was added at a mass concentration of 80% in an amount (absolute mass) of 0.01% of the mass of the cresol, and after heat preservation for 1 hour, it was cooled to room temperature.
D9. The cresol produced in comparative example one was heated to 90 c, hydrazine hydrate was added at a mass concentration of 80% in an amount (absolute mass) of 0.01% of the mass of the cresol, and after heat preservation for 1 hour, it was cooled to room temperature.
D10. The cresol produced in comparative example one was heated to 50 c, anhydrous sodium sulfate was added in an amount of 0.01% by mass of the cresol, and after heat preservation for 1 hour, it was cooled to room temperature.
D11. The cresol produced in comparative example I was heated to 90 deg.C, anhydrous sodium sulfate was added in an amount of 0.01% by mass of the cresol, and after heat preservation for 1 hour, it was cooled to room temperature.
D12. The cresol produced in comparative example one was heated to 50 c, hydrazine hydrate and anhydrous sodium sulfate were added at a mass concentration of 80% in an amount (absolute mass) of 0.01% by mass of the cresol, and anhydrous sodium sulfate was added in an amount of 0.01% by mass of the cresol, and after keeping the temperature for 1 hour, it was cooled to room temperature.
D13. The cresol produced in comparative example one was heated to 90 c, hydrazine hydrate and anhydrous sodium sulfate were added at a mass concentration of 80% in an amount (absolute mass) of 0.01% by mass of the cresol, and anhydrous sodium sulfate was added in an amount of 0.01% by mass of the cresol, and after keeping the temperature for 1 hour, it was cooled to room temperature.
D14. Experimental example cresol was produced.
D15. Cresol produced in comparative example two.
And (3) filling the control group sample into a transparent glass bottle, sealing, shading and storing in a cool and dry environment. The color of each control sample was observed visually at regular intervals, see table 8.
TABLE 8 color time chart of cresol samples of each control group
As can be seen from the statistics given in Table 8, at ambient temperature, when hydrazine hydrate was added alone, anhydrous sodium sulfate alone and sodium sulfate and hydrazine hydrate were added together to the cresol fraction, the cresol changed from pale yellow to dark brown in color by approximately 150 days, wherein D3 took only 120 days and was probably related to the water and other impurities carried in the hydrazine hydrate. Under the heating condition, hydrazine hydrate is added, which is favorable for prolonging the time of cresol color from light yellow to dark brown, approximately 30-60 days, and under the condition of higher heating temperature, the cresol distillate is favorable for long-time storage. The addition of anhydrous sodium sulfate has little effect on the time for which the cresol turns from light yellow to dark brown under heating.
The cresol fraction is heated to 50-90 ℃, and hydrazine hydrate and anhydrous sodium sulfate are added simultaneously, so that the time for changing the color of the cresol from light yellow to dark brown can be remarkably prolonged, and about 90-120 days are prolonged.
It should be understood that the above-described embodiments of the present invention are merely examples for clearly illustrating the present invention and are not intended to limit the embodiments of the present invention. Other variations and modifications will be apparent to persons skilled in the art in light of the above description. And are neither required nor exhaustive of all embodiments. Any modification, equivalent replacement, and improvement made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (8)
1. The production method of cresol antioxidant color fixation is characterized in that hydrazine hydrate is added into cresol fractions at the temperature of 50-90 ℃, and the addition amount of the hydrazine hydrate is 0.01-0.03 percent of the mass of cresol.
2. The cresol oxidation-resistant fixation production method as claimed in claim 1, wherein the addition amount of hydrazine hydrate is 0.01% of the mass of cresol.
3. The cresol antioxidant color fixing production method as claimed in claim 1, wherein anhydrous sodium sulfate is added into the cresol fraction at the temperature of 50-90 ℃, and the addition amount of the anhydrous sodium sulfate is 0.8-1 time of the mass of hydrazine hydrate.
4. The cresol oxidation-resistant fixation production method as claimed in claim 3, wherein the addition amount of anhydrous sodium sulfate is 0.8 times of the mass of hydrazine hydrate.
5. The oxidation-resistant color-fixing cresol production method as claimed in claim 1 or 3, wherein the cresol is prepared by rectifying mixed phenol.
6. The cresol antioxidant color fixing production system is characterized by comprising a phenol mixing rectification device, wherein the phenol mixing rectification device comprises a phenol mixing rectification tower, a cresol condenser, a cresol fraction tank and a cresol reflux pump which are arranged at the top discharge end of the phenol mixing rectification tower, and a tower kettle discharge pump and a heavy component tank which are arranged at the bottom discharge end of the phenol mixing rectification tower;
the device comprises a cresol distillate tank, and is characterized in that a hydrazine hydrate trough is arranged on the cresol distillate tank, the hydrazine hydrate trough is communicated with the cresol distillate tank, a cresol flow sensor is arranged at the feed end of the cresol distillate tank, a first flow control valve is arranged at the discharge end of the hydrazine hydrate trough, and the cresol flow sensor is electrically connected with the first flow control valve.
7. The cresol antioxidant color fixing production system as claimed in claim 6, wherein an anhydrous sodium sulfate tank is further arranged on the cresol fraction tank, and the anhydrous sodium sulfate tank is communicated with the cresol fraction tank.
8. The cresol antioxidant color fixing production system as claimed in claim 7, wherein a cresol feeding pipe is arranged on the anhydrous sodium sulfate tank and connected with the discharge end of the cresol distillate tank;
and a second flow control valve is arranged at the discharge end of the anhydrous sodium sulfate trough and is electrically connected with the first flow control valve.
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| GB820960A (en) * | 1957-01-10 | 1959-09-30 | Ici Ltd | Improvements in or relating to the stabilisation of phenols |
| JPS5268134A (en) * | 1975-12-05 | 1977-06-06 | Sanko Kagaku Kk | Method of preventing decoloration and coloration of phenols |
| JP2001261404A (en) * | 2000-03-15 | 2001-09-26 | Chem Grouting Co Ltd | Method for making iron material in structure corrosion- proof |
| US6362152B1 (en) * | 2000-04-07 | 2002-03-26 | The Dow Chemical Company | Low color and low haze formulations of sodium o-phenylphenate |
| CN1465558A (en) * | 2002-07-04 | 2004-01-07 | 中国科学院大连化学物理研究所 | Compound tinct stabilizer for inhibiting phenol and alkylphenol discoloration |
| CN106398304A (en) * | 2015-07-31 | 2017-02-15 | 魏忠 | Coal-based composite dye |
| CN210813998U (en) * | 2019-07-31 | 2020-06-23 | 浙江天成工程设计有限公司 | Rectification separation system |
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2022
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Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB820960A (en) * | 1957-01-10 | 1959-09-30 | Ici Ltd | Improvements in or relating to the stabilisation of phenols |
| JPS5268134A (en) * | 1975-12-05 | 1977-06-06 | Sanko Kagaku Kk | Method of preventing decoloration and coloration of phenols |
| JPS577612B2 (en) * | 1975-12-05 | 1982-02-12 | ||
| JP2001261404A (en) * | 2000-03-15 | 2001-09-26 | Chem Grouting Co Ltd | Method for making iron material in structure corrosion- proof |
| US6362152B1 (en) * | 2000-04-07 | 2002-03-26 | The Dow Chemical Company | Low color and low haze formulations of sodium o-phenylphenate |
| CN1465558A (en) * | 2002-07-04 | 2004-01-07 | 中国科学院大连化学物理研究所 | Compound tinct stabilizer for inhibiting phenol and alkylphenol discoloration |
| CN106398304A (en) * | 2015-07-31 | 2017-02-15 | 魏忠 | Coal-based composite dye |
| CN210813998U (en) * | 2019-07-31 | 2020-06-23 | 浙江天成工程设计有限公司 | Rectification separation system |
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