CN1094117C - Method of maintaining color of nonyl phenol - Google Patents
Method of maintaining color of nonyl phenol Download PDFInfo
- Publication number
- CN1094117C CN1094117C CN00111723A CN00111723A CN1094117C CN 1094117 C CN1094117 C CN 1094117C CN 00111723 A CN00111723 A CN 00111723A CN 00111723 A CN00111723 A CN 00111723A CN 1094117 C CN1094117 C CN 1094117C
- Authority
- CN
- China
- Prior art keywords
- color
- nonyl phenol
- colour
- ing
- hydrazine
- 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 - Fee Related
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- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 title claims abstract description 37
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 title claims abstract description 37
- 238000000034 method Methods 0.000 title claims abstract description 17
- 239000003381 stabilizer Substances 0.000 claims abstract description 23
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 claims abstract description 22
- 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 description 15
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims description 15
- -1 hydrazine class compound Chemical class 0.000 claims description 13
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 10
- 238000012423 maintenance Methods 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 3
- 150000003349 semicarbazides Chemical class 0.000 claims description 3
- 230000006641 stabilisation Effects 0.000 abstract description 6
- 238000011105 stabilization Methods 0.000 abstract description 6
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000009776 industrial production Methods 0.000 abstract 1
- 239000002932 luster Substances 0.000 description 16
- 230000000694 effects Effects 0.000 description 8
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 239000000654 additive Substances 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 241001115903 Raphus cucullatus Species 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000003019 stabilising effect Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 229910021654 trace metal Inorganic materials 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention relates to a method of maintaining the stable color of nonyl phenol. The present invention mainly solves the problems of color stabilizing agents in the existing literature of large color stabilizing agent consumption and poor color stabilization performance under high temperature through a technical scheme of adding a color stabilizing agent composed of hydrazide compounds and triphenyl phosphite in the nonyl phenol. The present invention can be used for industrial production.
Description
The present invention relates to keep the method for color of nonyl phenol.
Nonyl phenol is a kind of important fine-chemical intermediate, has purposes widely in fields such as tensio-active agent, lubricating oil additive, textile printing and dyeing paper making additives.The main union alkene of nonyl phenol and phenol chemical combination under the effect of an acidic catalyst form, and pure product are colourless transparent liquid.Because a variety of causes, industrial nonyl phenol product is easy to oxidation stain in storage process or the production process in derived product, and this sometimes variable color process is very rapid, can directly influence the sale and the use of nonyl phenol.Cause the factor of nonyl phenol product variable color a lot, all can variable color when nonyl phenol touches light, high temperature, dissolved trace metal, alkali and water vapor.Therefore, in the building-up process of nonyl phenol, material purity, processing condition, equipment material, accumulating mode etc. all can influence the color and luster and the color stability of nonyl phenol.Although both at home and abroad the variable color to phenolic compound has more research, up to now, to the variable color mechanism of nonyl phenol, to cause the look species still not fully aware of.
By adding that suitable stablizer changes with color and luster stable and that suppress the phenol derivmives blend biology is one of major measure of taking of most of research work.Hydrazine and derivative thereof comprise that hydrazine, hydrazine hydrate, semicarbazides etc. have color and luster stabilization preferably to monohydroxy and aromatic amine compounds under room temperature and lower temperature in numerous stablizers.According to patent US1973724, hydrazine class compound can directly add in the aromatic amine or phenol behind the purifying, also can directly add and carry out distillation purifying in the impurity again.With phenol is example, adds 0.01%, 0.03% and 0.005% hydrazine hydrate respectively and place sealed glass jars together with undressed phenol sample in phenol, and carry out the color stability experiment under direct sunlight.The sample that does not add hydrazine hydrate just began variable color in 5 hours, and the sample of adding hydrazine hydrate can keep respectively 4 days, 13 days and nondiscoloration in 26 days.But under the higher temperature or under the situation of being heated for a long time, the color and luster stabilization of hydrazine and derivative thereof obviously descends.Sample color and luster even can surpass undressed nonyl phenol sample in some cases.This just might cause disadvantageous effect to the production of derived product, and particularly bigger to those production process that need react under comparatively high temps influences, the consumption of hydrazine class compound is also bigger in addition.
The objective of the invention is in order to overcome in the past colour(ing)stabiliser large usage quantity in the document, and under comparatively high temps, the shortcoming that color stability can differ from provides a kind of method of new maintenance color of nonyl phenol.It is few that this method has a colour(ing)stabiliser consumption, and not only have good color and luster stabilization under room temperature or lesser temps, and can significantly improve the characteristics of hydrazine class compound color and luster stabilising effect under comparatively high temps.
The objective of the invention is to be achieved through the following technical solutions: a kind of method that keeps color of nonyl phenol, the colour(ing)stabiliser that in nonyl phenol, adds nonyl phenol weight 0.002～0.1%, colour(ing)stabiliser comprises hydrazine class compound and triphenyl phosphite, wherein in weight ratio, hydrazine class compound: triphenyl phosphite is 5: 1～1: 5.
In the technique scheme, the preferable range of colour(ing)stabiliser add-on is 0.002～0.01%; Hydrazine class compound is selected from hydrazine, hydrazine hydrate, semicarbazides or its mixture; In weight ratio, hydrazine class compound: the triphenyl phosphite preferable range is 2: 1～1: 2.
The addition manner of colour(ing)stabiliser can be directly to add or add with the solution form, but more convenient with direct interpolation.The color stability of colour(ing)stabiliser can be estimated in lucifuge not, do not carried out under the secluding air condition, and evaluation temperature is from room temperature to 120 ℃.The color measuring method is measured with spectrophotometer method with reference to GB3143-82.
Among the present invention owing in hydrazine class compound, added triphenyl phosphite, the color stability of colour(ing)stabiliser can be improved greatly, make it not only can be useful in color of nonyl phenol under room temperature and the lesser temps, and can be under 120 ℃, make nonyl phenol still keep color stability energy preferably, and its consumption is 0.002～0.1% of a nonyl phenol weight only, has obtained effect preferably.
The invention will be further elaborated below by embodiment.[embodiment 1]
The industrial nonyl phenol product of fetching with factory is a research object, takes by weighing 50 respectively and restrains in three the 100 milliliters of wide-necked bottles that are placed in.With the sample that is untreated as standard, its color and luster is 44Hazen, add 0.005% and 0.01% colour(ing)stabiliser of nonyl phenol weight in its dodo split respectively, wherein the weight ratio of hydrazine hydrate and triphenyl phosphite is 2: 1, in lucifuge not, do not compare test under the condition of secluding air, room temperature, its color and luster changing conditions of results of regular determination, the result is as shown in table 1.
Table 1
Colour(ing)stabiliser of the present invention as can be seen from the table is at normal temperature, non-lucifuge and do not have the satisfactory stability color and luster and suppress the effect that color and luster produces under the secluding air situation, has certain decolourization for the industrial nonyl phenol product that produces certain color and luster.[embodiment 2]
According to operation steps and the condition of embodiment 1, just changing the examination temperature is 60 ℃, and the usage quantity of colour(ing)stabiliser, and its evaluation result sees the following form 2.
Table 2
Colour(ing)stabiliser of the present invention as can be seen from Table 2 still has good steady look and presses down the look ability at 60 ℃, and its effect that the industrial nonyl phenol that produced certain color and luster is faded is more obvious simultaneously.[embodiment 3]
60 ℃ of following colour(ing)stabilisers of the present invention and steady look effect of single hydrazine hydrate stablizer and contrast experiment.
Respectively claim 50 to restrain in three wide-necked bottles that are placed in the nonyl phenol that newly steams, with the sample that is untreated as standard, in other two bottles, add 0.05% colour(ing)stabiliser of the present invention (wherein the mass ratio of hydrazine hydrate and triphenyl phosphite is 1: 1) of nonyl phenol weight and 0.05% hydrazine hydrate respectively, in 60 ℃, do not carry out stable contrast experiment under the condition of secluding air, experimental result sees Table 3.
Table 3
Experiment shows that the color and luster stabilization of hydrazine hydrate obviously descends along with the prolongation of heat-up time, and when being heated to 29 days, hydrazine hydrate not only can not play steady look effect but also the nonyl phenol product color is further deepened.The steady look ability of colour(ing)stabiliser of the present invention obviously is better than single hydrazine hydrate stablizer.[embodiment 4]
120 ℃ of following colour(ing)stabilisers of the present invention and steady look effect of single hydrazine hydrate stablizer and contrast experiment.
Experimental implementation and colour(ing)stabiliser of the present invention are formed with embodiment 3, and color stability is tested at 120 ℃, does not carry out under the secluding air, and experimental result sees Table 4.
Table 4
Stablizer of the present invention as can be seen from Table 4 at high temperature still has to be stablized color and luster preferably and suppresses the ability that color and luster produces, and can obviously improve hydrazine hydrate at high temperature to the stabilization of color of nonyl phenol by adding triphenyl phosphite.
Claims (4)
1, a kind of method that keeps color of nonyl phenol, it is characterized in that in nonyl phenol, adding the colour(ing)stabiliser of nonyl phenol weight 0.002～0.1%, colour(ing)stabiliser comprises hydrazine class compound and triphenyl phosphite, wherein in weight ratio, hydrazine class compound: triphenyl phosphite is 5: 1～1: 5.
2, according to the method for the described maintenance color of nonyl phenol of claim 1, the add-on that it is characterized in that colour(ing)stabiliser is 0.002～0.01% of a nonyl phenol weight.
3,, it is characterized in that hydrazine class compound is selected from hydrazine, hydrazine hydrate, semicarbazides or its mixture according to the method for the described maintenance color of nonyl phenol of claim 1.
4, according to the method for the described maintenance color of nonyl phenol of claim 1, it is characterized in that in weight ratio hydrazine class compound: triphenyl phosphite is 2: 1～1: 2.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN00111723A CN1094117C (en) | 2000-02-24 | 2000-02-24 | Method of maintaining color of nonyl phenol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN00111723A CN1094117C (en) | 2000-02-24 | 2000-02-24 | Method of maintaining color of nonyl phenol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1310159A CN1310159A (en) | 2001-08-29 |
| CN1094117C true CN1094117C (en) | 2002-11-13 |
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ID=4581626
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN00111723A Expired - Fee Related CN1094117C (en) | 2000-02-24 | 2000-02-24 | Method of maintaining color of nonyl phenol |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1094117C (en) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3553272A (en) * | 1966-05-11 | 1971-01-05 | Nat Polychemicals Inc | Compositions for and methods of inhibiting the discoloration of alkylated phenols |
-
2000
- 2000-02-24 CN CN00111723A patent/CN1094117C/en not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3553272A (en) * | 1966-05-11 | 1971-01-05 | Nat Polychemicals Inc | Compositions for and methods of inhibiting the discoloration of alkylated phenols |
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| Publication number | Publication date |
|---|---|
| CN1310159A (en) | 2001-08-29 |
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Granted publication date: 20021113 Termination date: 20120224 |