CN108383692B - Composite color stabilizer for inhibiting alkylphenol discoloration and application thereof - Google Patents
Composite color stabilizer for inhibiting alkylphenol discoloration and application thereof Download PDFInfo
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- CN108383692B CN108383692B CN201810362209.0A CN201810362209A CN108383692B CN 108383692 B CN108383692 B CN 108383692B CN 201810362209 A CN201810362209 A CN 201810362209A CN 108383692 B CN108383692 B CN 108383692B
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- 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
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Abstract
The invention discloses a composite color stabilizer for inhibiting the color change of alkylphenol, which consists of a reducing agent and a synergistic antioxidant; the reducing agent is alkali metal salts of sulfurous acid and pyrosulfurous acid; the synergistic antioxidant is polybasic acid or alkali metal salt thereof. The composition and dosage ratio of the color stabilizer are screened through a large number of experiments, and the experiment result shows that the optimal alkylphenol discoloration inhibiting performance is achieved when the dosage of the composite color stabilizer (the mass ratio of the reducing agent to the synergistic antioxidant is 2: 1-4: 1) is 100-200 ppm. The invention has the advantages of easily obtained raw materials and low cost, can particularly solve the problem of the color change of the alkylphenol at high temperature, and has important application value.
Description
Technical Field
The invention relates to a color stabilizer, in particular to a composite color stabilizer for inhibiting the color change of alkylphenol, belonging to the technical field of chemistry.
Background
Alkylphenol is an important intermediate in fine chemical production, and has wide application in the fields of pesticides, perfumes, dyes, medicines, antioxidants, polymerization inhibitors, ultraviolet absorbers, rubber auxiliaries, fuel additives, coatings, feed additives, synthetic materials and the like, and in recent years, the domestic demand for alkylphenol is on the trend of rapid increase due to the rapid development of polyolefin antioxidants, rubber antioxidants and the fine chemical industry. In the storage process, the alkylphenol is easily subjected to autoxidation reaction to generate a colored substance ketone under the conditions of illumination, air oxidation, impurity induction, heating, metal ion catalysis and the like, the color and the appearance are changed, and the commercial value of a phenol product is influenced. Therefore, the research on the color stabilizing technology of alkylphenol products, including the color stabilizer and the color stabilizing process, has important significance.
Many patents report color stabilizers and stabilization techniques for alkylphenols, which mainly play a role in color stabilization by adding compounds to phenols, such as US2672485 to add polycarboxylic acids, US2752398 to add phosphoric acid, US2877273 to add abietylamine dicarboxylic acid and salts thereof, US2727928 to add hypophosphorous acid and salts or esters thereof, US3553272 to add organic phosphites, US3403186 to add salicylic acid US3629339 to add arsenic-containing compounds, US4386224, US4487987 to add N, N-diethylhydroxylamine, US4337369 to add dioxane, JP7768134 to add hydrazine hydrate, and the like. These methods have a good effect of inhibiting the discoloration of phenol caused by metal impurities, or the discoloration of phenol caused by air, light, impurity acids or strong bases.
Patent CN10131153 reports a color stabilization method, which eliminates impurity-induced factors of phenol product discoloration by adsorption, complexation, extraction and other processes, and improves product purity to increase color stability of phenol. The technology only relates to a factor for inhibiting the phenol discoloration caused by impurity induction factors, but does not relate to other induced discoloration factors which are inevitable in storage of light, temperature and the like; CN465558 reports a composite color stabilizer mixed by phosphate and polybasic acid chelating agent, and the action principle of the composite color stabilizer is mainly designed aiming at the discoloration factors induced by a metal container in the storage process.
Disclosure of Invention
The purpose of the invention is as follows: the invention aims to overcome the defects in the prior art, and provides a composite color stabilizer capable of obviously inhibiting the color change of alkylphenol by screening different raw material compositions and weight ratios through a large number of experiments. The invention has the advantages of easily obtained raw materials, low cost, easy popularization and application and important application value.
The technical scheme is as follows: in order to realize the purpose of the invention, the invention adopts the technical scheme that:
a composite color stabilizer for inhibiting the color change of alkylphenol is composed of reducer and synergistic antioxidizing agent.
Preferably, the compound color stabilizer for inhibiting the discoloration of alkylphenol is characterized in that the reducing agent is alkali metal salts of sulfurous acid and pyrosulfurous acid, and the synergistic antioxidant is polybasic acid or alkali metal salts thereof.
Preferably, the mass ratio of the reducing agent to the synergistic antioxidant in the composite color stabilizer for inhibiting the color change of the alkylphenol is 1: 0.1-1: 10.
In a particularly preferred embodiment, the mass ratio of the reducing agent to the synergistic antioxidant is 2: 1-4: 1.
Preferably, the above composite color stabilizer for inhibiting the discoloration of the alkylphenol is characterized in that the reducing agent is one or more of sodium sulfite, potassium sulfite, sodium bisulfite, potassium bisulfite, sodium metabisulfite, potassium metabisulfite and sodium hydrosulfite.
Preferably, the synergistic antioxidant of the composite color stabilizer for inhibiting the color change of the alkylphenol is one or more of citric acid, tartaric acid, lycium acid or salts thereof.
Preferably, the composite color stabilizer is applied to inhibiting the discoloration of alkylphenol, and the dosage of the composite color stabilizer is 10-1000 ppm. Preferably, the amount of the composite color stabilizer is 100-200 ppm. In a particularly preferred embodiment, the amount of the composite color stabilizer is 200 ppm.
Has the advantages that: compared with the prior art, the invention has the following advantages:
according to the invention, through a large number of experimental screening, the composite color stabilizer consisting of alkali metal salts of sulfurous acid and pyrosulfurous acid as a reducing agent and polybasic acid or alkali metal salts of the sulfurous acid and the pyrosulfurous acid as a synergistic antioxidant is preferably selected, and the dosage ratio is screened through a large number of experiments, and the experimental result shows that the optimal alkylphenol discoloration inhibiting performance is achieved when the dosage of the composite color stabilizer (the mass ratio of the reducing agent to the synergistic antioxidant is 2: 1-4: 1) is 100-200 ppm. In particular, the problem of the discoloration of the alkylphenol at high temperature can be solved.
Detailed Description
The present invention is further illustrated by the following examples, which are intended to be purely exemplary and are not intended to limit the scope of the invention, as various equivalent modifications of the invention will occur to those skilled in the art upon reading the present disclosure and fall within the scope of the appended claims.
Example 1
Carrying out reduced pressure rectification on the industrial p-cresol crude product produced by the diazotization method, collecting 110-114/(0.09-0.094) MPa p-cresol products, storing under the natural condition of sealing and shading, detecting the color of the p-cresol once a month, and comparing the color change of a sample by visual inspection, wherein the experimental result is shown in table 1.
Examples 2 to 5
Carrying out reduced pressure rectification on the industrial p-cresol crude product produced by the diazotization method, and adding a composite color stabilizer (the mass ratio of sodium pyrosulfite to citric acid is 2: 1) into a rectifying still, wherein the adding amount is 0-0.25% of the mass of the crude p-cresol. Collecting 110-114/(0.09-0.094) MPa p-cresol products, storing under a sealed and light-proof natural condition, detecting the color of the p-cresol once a month, and comparing the color change of each group of samples by visual inspection. The specific experimental results are shown in table 1.
TABLE 1 Effect of different addition amounts of color stabilizer on inhibiting discoloration of p-cresol during rectification
The experimental results shown in table 1 show that: adding a color stabilizer into a rectifying still of the crude p-cresol to delay the color change of the p-cresol product, wherein when the using amount of the composite color stabilizer is 0-0.20%, the effect of inhibiting color change is better along with the increase of the using amount of the composite color stabilizer; particularly, when the addition amount of the color stabilizer is 0.2%, the color stabilizing effect is best, the p-cresol sample produced by vacuum rectification still keeps white after being stored for half a year, and the sample control group without the color stabilizer has obvious color change after one month of the reservoir.
Examples 6 to 12
Adding 100g of freshly steamed analytically pure m-methylphenol into a beaker, adding a certain mass of a composite color stabilizer (sodium metabisulfite: citric acid is 4:1) according to the table 2, uniformly stirring, then putting the beaker into a vacuum oven at 50 ℃, regularly taking out and comparing with a standard color number, measuring the color change of a sample, measuring the chroma of alkylphenol according to GB3143-82 (liquid chemical product color measurement method), measuring the chroma of the sample by adopting a platinum-cobalt colorimetric method, and indicating that the color is darker when the numerical value is larger in terms of Hazen unit. The results of the specific measurement of the change in the color value of the sample are shown in Table 3.
TABLE 2 amount of stabilizer added
TABLE 3 color value change
As can be seen from table 3, the addition of the composite color stabilizer to m-cresol slowed the rate of m-cresol discoloration; the color stabilizing effect of the color stabilizer within the range of 100-200 ppm is good, and particularly the color stabilizing effect is optimal when the amount of the color stabilizer is 200 ppm.
The foregoing is only a preferred embodiment of the present invention, and it should be noted that, for those skilled in the art, various modifications and decorations can be made without departing from the principle of the present invention, and these modifications and decorations should also be regarded as the protection scope of the present invention.
Claims (1)
1. The composite color stabilizer for inhibiting the color change of alkylphenol is characterized by comprising sodium metabisulfite and citric acid in a mass ratio of 2: 1-4: 1; the amount of the composite color stabilizer is 200 ppm.
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| CN201810362209.0A CN108383692B (en) | 2018-04-20 | 2018-04-20 | Composite color stabilizer for inhibiting alkylphenol discoloration and application thereof |
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| CN201810362209.0A CN108383692B (en) | 2018-04-20 | 2018-04-20 | Composite color stabilizer for inhibiting alkylphenol discoloration and application thereof |
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| CN108383692B true CN108383692B (en) | 2021-04-13 |
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| CN111792979A (en) * | 2020-06-18 | 2020-10-20 | 湖南国发精细化工科技有限公司 | O-isopropylphenol anti-blushing agent and o-isopropylphenol containing anti-blushing agent |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB717634A (en) * | 1951-07-28 | 1954-10-27 | Bataafsche Petroleum | Process for the stabilisation of alkyl phenols |
| US3403186A (en) * | 1965-11-30 | 1968-09-24 | Hooker Chemical Corp | Stabilization of phenols |
| CN1107133A (en) * | 1993-10-29 | 1995-08-23 | 通用电气公司 | A process for inhibiting dihydric phenol degradation and color formation and composition thereof |
| CN101735022A (en) * | 2009-11-30 | 2010-06-16 | 中国蓝星（集团）股份有限公司 | Method for preparing stable bisphenol sodium salt solution |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102005017126A1 (en) * | 2005-04-14 | 2006-10-19 | Cognis Ip Management Gmbh | Process for the preparation of cardanol (I) |
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB717634A (en) * | 1951-07-28 | 1954-10-27 | Bataafsche Petroleum | Process for the stabilisation of alkyl phenols |
| US3403186A (en) * | 1965-11-30 | 1968-09-24 | Hooker Chemical Corp | Stabilization of phenols |
| CN1107133A (en) * | 1993-10-29 | 1995-08-23 | 通用电气公司 | A process for inhibiting dihydric phenol degradation and color formation and composition thereof |
| CN101735022A (en) * | 2009-11-30 | 2010-06-16 | 中国蓝星（集团）股份有限公司 | Method for preparing stable bisphenol sodium salt solution |
Non-Patent Citations (1)
| Title |
|---|
| 复方间苯二酚洗剂的稳定性考察;印嘉骏;《江苏药学与临床研究》;19971231;第5卷(第2期);第32-33页 * |
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