CN1919438A - Alkylbenzene alkylalethylene polyoxyethylene and its modified product - Google Patents
Alkylbenzene alkylalethylene polyoxyethylene and its modified product Download PDFInfo
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- CN1919438A CN1919438A CN200510092891.9A CN200510092891A CN1919438A CN 1919438 A CN1919438 A CN 1919438A CN 200510092891 A CN200510092891 A CN 200510092891A CN 1919438 A CN1919438 A CN 1919438A
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- alkylalethylene
- polyoxyethylene
- alkylbenzene
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Abstract
The invention discloses an alkyl pridefine alcohol polyoxyethylene thioether and modified product, which is characterized by the following: possessing superior wet, low-temperature washing, emulsifying, hard water tolerance and easy biological decomposable property, fitting for light-industrial, weaving, agricultural, oil and metal manufacturing department.
Description
Technical field
The present invention relates to a kind of alkylbenzene alkylalethylene polyoxyethylene and modified product thereof.
Background technology
Performances such as that APES has is wetting, cold washing, emulsification, anti-hard water and easily biological-degradable are widely used in departments such as light industry, weaving, agricultural, oil, metal processing.
APES (NPE or OP) is the second largest class non-ionic surface active agent after AEO (APE).Have stability in hard water of good wetting, cold washing, emulsibility, oxidative resistance etc., belong to a fastest-rising class surfactant in the world.They have 45% to be used for washing agent approximately, 55% be used for other industry.Over nearly 20 years, have research to think that NPE or OP metabolic are poor, its metabolin has female effect.76/769/EEC number instruction of European Council proposed restriction to the use of APES.This bill is formally effective on January 17th, 2005 relevant for the qualification of nonyl phenol and NPE content.
Domestic research report is as follows: 1, nonyl phenol is in the distribution of China's some areas water environment: aquatic organism particularly aquatic animal has the effect of concentrating to nonyl phenol; The nonyl phenol that is present in water environment can enter in the human body through aquatic animal food by water with the food chain transmission.2, the toxic action of nonyl phenol: kidney, liver and reproductive system to rat all can work the mischief, but responsive order is: reproductive system---kidney---liver.3, nonyl phenol dynamic metabolism process in vivo: nonyl phenol mainly excretes through behind the liver metabolism in vivo; Food can influence nonyl phenol and absorb and the prolongation nonyl phenol holdup time in vivo through alimentary canal; 4, the plan estrogen-like action of nonyl phenol; It can make grow up removal ovary rat and underage mouse uterus weight; In utero reach and expose nonyl phenol tire mouse lactation skin infections of newborn infants effect is arranged, every birth index of sub-mouse is reduced; 5, nonyl phenol is to the illeffects mechanism of rat testicle: NP or OP can suppress androgone spermatogenesis process in conjunction with albumen by suppressing synthetic androgen.Because the extensive use of NPE in industry and family, NP or OP pollute obviously and surpass abroad in the present water system of China.
AEO is compared some performance with APES far short of what is expected, so press for a kind of chemical substance of new structure now, performance is good, do not contain hormone substitutes APES and AEO, the alkylbenzene alkylalethylene polyoxyethylene that this just performance of the present invention is good, do not contain hormone.
Summary of the invention
The object of the present invention is to provide a kind of alkylbenzene alkylalethylene polyoxyethylene and modified product thereof, can substitute APES and AEO and their remodeling product thereof.
The experiment that herbal classic is a large amount of excessively, we obtain a kind of alkylbenzene alkylalethylene polyoxyethylene of the present invention and modified product thereof, and the molecular formula of this alkylbenzene alkylalethylene polyoxyethylene and modified product thereof is:
Wherein: m is any one integer in 1～30;
N is any one integer in 0～30;
P is any one integer in 1～12;
Q is any one integer in 0～50;
R is-H ,-CH
2COOM ,-SO
3M ,-R '-SO
3M ,-PO
3M
2In any one;
R ' is C
1～C
10In any one alkyl;
M is any one in alkali metal, amine, monoethanolamine, diethanol amine, the triethanolamine.
In alkylbenzene alkylalethylene polyoxyethylene and the modified product molecular formula thereof, be preferably m and be any one integer, n in 8～16 and be any one integer, p in 0～9 and be any one integer, q in 1～6 and be any one integer in 0～25; R is-H ,-CH
2COOM ,-SO
3M ,-R '-SO
3M ,-PO
3M
2In any one; R ' is C
1～C
10In any one alkyl; M is any one in sodium, potassium, lithium, amine, monoethanolamine, diethanol amine, the triethanolamine.
More preferably m is that any one integer, n in 8～12 are that any one integer, p in 0～9 is that any one integer, q in 1～4 is any one integer in 0～25; R is-H ,-CH
2COOM ,-SO
3M ,-R '-SO
3Among the M any one; R ' is C
1～C
6In any one alkyl; M is any one in sodium, potassium, the amine.
Be preferably m at last and be any one integer, n in 8～12 and be 0, p is 1, q is any one integer in 5～25; R is for m in the alkylbenzene alkylalethylene polyoxyethylene of-H or alkylbenzene alkylalethylene polyoxyethylene and the modified product molecular formula thereof is that any one integer, n in 8～12 is 0, p is 1, q is any one integer in 2～8; R is-CH
2COOM ,-SO
3Among the M any one; M is any one alkylbenzene alkylalethylene polyoxyethylene carboxylate or the sulfuric acid in sodium, potassium, the amine.
In sum, alkylbenzene alkylalethylene polyoxyethylene and modified product thereof have performances such as good wetting, cold washing, emulsification, anti-hard water and easily biological-degradable, are widely used in departments such as light industry, weaving, agricultural, oil, metal processing.Can substitute APES and AEO and their modified product thereof.
The present invention has the following advantages:
(1) oxygen that does not contain in alkylbenzene alkylalethylene polyoxyethylene among hormone the present invention and the modified product thereof does not directly link to each other with phenyl ring, so do not contain hormone, compliance with environmental protection requirements does not have injury to human body, can reach extensive use, can substitute APES;
(2) have performances such as good wetting, cold washing, emulsification, anti-hard water and easily biological-degradable, can alternative fats alcohol APEO in some field.
The present invention is elaborated with the following examples, and these embodiment only are used for description effect, rather than limit the scope of the invention.
Embodiment
Embodiment one: nonyl benzene methyl alcohol APEO-10 synthetic
170 gram carrene and 27 gram alchlors are joined in the there-necked flask, this mixture is stirred under 40 degrees celsius, treat that alchlor dissolves fully, after the whole system clarification, the control temperature is about 40 degrees centigrade, drip nonyl benzene 204 grams under the condition of normal pressure, drip reaction in 2 hours 2.5 hours, reaction finishes the back and adds clear water the alchlor hydrolysis is fallen, again with clear water wash be neutrality to system till, last rectification under vacuum finally obtains 212 gram products.The hydrolysis under 150 degrees centigrade of alkali conditions of this product is obtained nonyl benzene methyl alcohol; with the nonyl benzene methyl alcohol decompression dehydration under 110 degrees celsius that obtains; in reactor, charge into nonyl benzene methyl alcohol after dewatering under the condition of nitrogen protection and mix with base catalyst (as NaOH) and be warming up to 160 degrees centigrade, charge into the oxirane of liquid state or gaseous state then.The dividing potential drop of retaining ring oxidative ethane is about 0.4～0.5MPa, and till required oxirane added, it was 10 moles that institute adds number of moles of ethylene oxide.Decompression is denitrogenated, in and material, finally obtain product 426 gram nonyl benzene methyl alcohol APEOs-10.
Embodiment two: nonyl benzene methyl alcohol APEO-10 carboxylic acid sodium synthetic
170 gram carrene and 27 gram alchlors are joined in the there-necked flask, this mixture is stirred under 40 degrees celsius, treat that alchlor dissolves fully, after the whole system clarification, the control temperature is about 40 degrees centigrade, drip nonyl benzene 254 grams under the condition of normal pressure, drip reaction in 2 hours 2.5 hours, reaction finishes the back and adds clear water the alchlor hydrolysis is fallen, again with clear water wash be neutrality to system till, last rectification under vacuum finally obtains 212 gram products.The hydrolysis under 150 degrees centigrade of alkali conditions of this product is obtained nonyl benzene methyl alcohol; with the nonyl benzene methyl alcohol decompression dehydration under 110 degrees celsius that obtains; in reactor, charge into nonyl benzene methyl alcohol after dewatering under the condition of nitrogen protection and mix with base catalyst (as NaOH) and be warming up to 160 degrees centigrade, charge into the oxirane of liquid state or gaseous state then.The dividing potential drop of retaining ring oxidative ethane is about 0.4～0.5MPa, and till required oxirane added, it was 10 moles that institute adds number of moles of ethylene oxide.Decompression is denitrogenated, in and material, finally obtain product 445 gram nonyl benzene methyl alcohol APEOs-10.The nonyl benzene methyl alcohol APEO and the monoxone that obtain are made nonyl benzene methyl alcohol APEO-10 carboxylic acid sodium 457 grams under the condition that highly basic (as NaOH) exists.
Claims (6)
1, a kind of alkylbenzene alkylalethylene polyoxyethylene and modified product thereof, the molecular formula of this alkylbenzene alkylalethylene polyoxyethylene and modified product thereof is:
Wherein: m is any one integer in 1～30;
N is any one integer in 0～30;
P is any one integer in 1～12;
Q is any one integer in 0～50;
R is-H ,-CH
2COOM ,-SO
3M ,-R '-SO
3M ,-PO
3M
2In any one;
R ' is C
1～C
10In any one alkyl;
M is any one in alkali metal, amine, monoethanolamine, diethanol amine, the triethanolamine.
2, alkylbenzene alkylalethylene polyoxyethylene according to claim 1 and modified product thereof, in alkylbenzene alkylalethylene polyoxyethylene and the modified product molecular formula thereof, m is that any one integer, the n in 8～16 is that any one integer, p in 0～9 is that any one integer, q in 1～6 is any one integer in 0～25; R is-H ,-CH
2COOM ,-SO
3M ,-R '-SO
3M ,-PO
3M
2In any one; R ' is C
1～C
10In any one alkyl; M is any one in sodium, potassium, amine, lithium, monoethanolamine, diethanol amine, the triethanolamine.
3, according to described alkylbenzene alkylalethylene polyoxyethylene of one of claim 1～2 and modified product thereof, in alkylbenzene alkylalethylene polyoxyethylene and the modified product molecular formula thereof, m is that any one integer, the n in 8～12 is that any one integer, p in 0～9 is that any one integer, q in 1～4 is any one integer in 0～25; R is-H ,-CH
2COOM ,-SO
3Among the M any one; R ' is C
1～C
6In any one alkyl; M is any one in sodium, potassium, the amine.
4, according to described alkylbenzene alkylalethylene polyoxyethylene of one of claim 1～3 and modified product thereof, in alkylbenzene alkylalethylene polyoxyethylene and the modified product molecular formula thereof, m is that any one integer, the n in 8～12 is 0, p is 1, q is any one integer in 5～25; R is-H.
5, according to described alkylbenzene alkylalethylene polyoxyethylene of one of claim 1～3 and modified product thereof, in alkylbenzene alkylalethylene polyoxyethylene and the modified product molecular formula thereof, m is that any one integer, the n in 8～12 is 0, p is 1, q is any one integer in 2～8; R is-CH
2COOM ,-SO
3Among the M any one; M is any one in sodium, potassium, the amine.
6, according to described alkylbenzene alkylalethylene polyoxyethylene of one of claim 1～5 and modified product thereof, it is characterized in that, alkylbenzene alkylalethylene polyoxyethylene and modified product thereof have performances such as good wetting, cold washing, emulsification, anti-hard water and easily biological-degradable, are widely used in departments such as light industry, weaving, agricultural, oil, metal processing.Can substitute APES and AEO and their modified product thereof.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN200510092891.9A CN1919438A (en) | 2005-08-25 | 2005-08-25 | Alkylbenzene alkylalethylene polyoxyethylene and its modified product |
| PCT/CN2006/002151 WO2007022718A1 (en) | 2005-08-25 | 2006-08-23 | Alkyl aryl alkyl alcohols, their derivations and preparation process thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN200510092891.9A CN1919438A (en) | 2005-08-25 | 2005-08-25 | Alkylbenzene alkylalethylene polyoxyethylene and its modified product |
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| Publication Number | Publication Date |
|---|---|
| CN1919438A true CN1919438A (en) | 2007-02-28 |
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| CN200510092891.9A Pending CN1919438A (en) | 2005-08-25 | 2005-08-25 | Alkylbenzene alkylalethylene polyoxyethylene and its modified product |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102943000A (en) * | 2012-12-17 | 2013-02-27 | 江南大学 | Active oxygen brightening laundry detergent |
| CN105968338A (en) * | 2016-07-19 | 2016-09-28 | 南通市晗泰化工有限公司 | Alpha-phenyl alkyl alcohol polyoxyethylene ether hydroxypropyl allyl ether as well as derivative and preparation method thereof |
| CN106187713A (en) * | 2016-07-19 | 2016-12-07 | 南通市晗泰化工有限公司 | Alkylbenzene methanol polyoxyethylene ether hydroxypropyl allyl ether and derivant and preparation method thereof |
| CN106187834A (en) * | 2016-07-19 | 2016-12-07 | 南京林业大学 | α phenylalkyl polyoxyethylenated alcohol disodium succinate salt and preparation method |
| CN106279670A (en) * | 2016-07-19 | 2017-01-04 | 南通市晗泰化工有限公司 | α phenylalkyl polyoxyethylenated alcohol ammonium sulfate and preparation method |
-
2005
- 2005-08-25 CN CN200510092891.9A patent/CN1919438A/en active Pending
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102943000A (en) * | 2012-12-17 | 2013-02-27 | 江南大学 | Active oxygen brightening laundry detergent |
| CN105968338A (en) * | 2016-07-19 | 2016-09-28 | 南通市晗泰化工有限公司 | Alpha-phenyl alkyl alcohol polyoxyethylene ether hydroxypropyl allyl ether as well as derivative and preparation method thereof |
| CN106187713A (en) * | 2016-07-19 | 2016-12-07 | 南通市晗泰化工有限公司 | Alkylbenzene methanol polyoxyethylene ether hydroxypropyl allyl ether and derivant and preparation method thereof |
| CN106187834A (en) * | 2016-07-19 | 2016-12-07 | 南京林业大学 | α phenylalkyl polyoxyethylenated alcohol disodium succinate salt and preparation method |
| CN106279670A (en) * | 2016-07-19 | 2017-01-04 | 南通市晗泰化工有限公司 | α phenylalkyl polyoxyethylenated alcohol ammonium sulfate and preparation method |
| CN105968338B (en) * | 2016-07-19 | 2018-08-07 | 南通市晗泰化工有限公司 | α-phenylalkyl alcohol polyoxyethylene ether hydroxypropyl allyl ether and its derivative and preparation method |
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