CN106496078A - A kind of palmitoleic acid hexahydrobenzoid acid polyethylene glycol sulfonated ester manufacture method - Google Patents
A kind of palmitoleic acid hexahydrobenzoid acid polyethylene glycol sulfonated ester manufacture method Download PDFInfo
- Publication number
- CN106496078A CN106496078A CN201610893276.6A CN201610893276A CN106496078A CN 106496078 A CN106496078 A CN 106496078A CN 201610893276 A CN201610893276 A CN 201610893276A CN 106496078 A CN106496078 A CN 106496078A
- Authority
- CN
- China
- Prior art keywords
- acid
- polyethylene glycol
- hexahydrobenzoid
- palmitoleic acid
- palmitoleic
- 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.)
- Pending
Links
- SECPZKHBENQXJG-FPLPWBNLSA-N palmitoleic acid Chemical compound CCCCCC\C=C/CCCCCCCC(O)=O SECPZKHBENQXJG-FPLPWBNLSA-N 0.000 title claims abstract description 67
- 239000002253 acid Substances 0.000 title claims abstract description 39
- 239000002202 Polyethylene glycol Substances 0.000 title claims abstract description 35
- 229920001223 polyethylene glycol Polymers 0.000 title claims abstract description 35
- 235000021319 Palmitoleic acid Nutrition 0.000 title claims abstract description 34
- SECPZKHBENQXJG-UHFFFAOYSA-N cis-palmitoleic acid Natural products CCCCCCC=CCCCCCCCC(O)=O SECPZKHBENQXJG-UHFFFAOYSA-N 0.000 title claims abstract description 33
- 238000000034 method Methods 0.000 title claims abstract description 20
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 15
- 150000002148 esters Chemical class 0.000 title claims abstract description 13
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims abstract description 26
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims abstract description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 18
- 238000006243 chemical reaction Methods 0.000 claims abstract description 18
- 230000035484 reaction time Effects 0.000 claims abstract description 12
- 238000001816 cooling Methods 0.000 claims abstract description 6
- 238000003756 stirring Methods 0.000 claims abstract description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000005886 esterification reaction Methods 0.000 claims description 15
- 230000032050 esterification Effects 0.000 claims description 10
- 239000004094 surface-active agent Substances 0.000 claims description 8
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 6
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 6
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 6
- 239000005642 Oleic acid Substances 0.000 claims description 6
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 6
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 6
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 6
- 239000003125 aqueous solvent Substances 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 5
- 230000018044 dehydration Effects 0.000 claims description 5
- 238000006297 dehydration reaction Methods 0.000 claims description 5
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 238000003786 synthesis reaction Methods 0.000 claims description 4
- 230000000694 effects Effects 0.000 claims description 2
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 claims 3
- 239000000463 material Substances 0.000 claims 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 238000005202 decontamination Methods 0.000 abstract description 3
- 230000003588 decontaminative effect Effects 0.000 abstract description 3
- 238000005406 washing Methods 0.000 abstract description 3
- 238000006386 neutralization reaction Methods 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 8
- 229910052708 sodium Inorganic materials 0.000 description 8
- 239000011734 sodium Substances 0.000 description 8
- RFVNOJDQRGSOEL-UHFFFAOYSA-N 2-hydroxyethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCO RFVNOJDQRGSOEL-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 229950007687 macrogol ester Drugs 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000002351 wastewater Substances 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 229960003511 macrogol Drugs 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000009736 wetting Methods 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 1
- 238000002144 chemical decomposition reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 239000003317 industrial substance Substances 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000009941 weaving Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/25—Sulfonic acids having sulfo groups bound to carbon atoms of rings other than six-membered aromatic rings of a carbon skeleton
- C07C309/27—Sulfonic acids having sulfo groups bound to carbon atoms of rings other than six-membered aromatic rings of a carbon skeleton containing carboxyl groups bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/32—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of salts of sulfonic acids
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention relates to palmitoleic acid hexahydrobenzoid acid polyethylene glycol sulfonated ester manufacture method and its application.Its manufacturing step is as follows：(1) hexahydrobenzoid acid sulfonate is put into retort, N with polyethylene glycol according to mole 1: 12Protection, adds 0.5% p-methyl benzenesulfonic acid of gross mass, 10 15% dimethylbenzene of gross mass；(2) 130 140 DEG C of reactions, 68 hours reaction time are heated to；(3) when reaction dehydrating amount reaches theoretical water yield 90%, according to palmitoleic acid: polyethylene glycol (mole) is that 1: 1.05 1.15 ratio adds palmitoleic acid, 130 140 DEG C of reactions, 8 10 hours reaction time；(4) theoretical water yield 90% is reached, acid number reaches 10 15mgKOH/g, improves 150 160 DEG C of reaction temperature and react 1.5 hours, steam dimethylbenzene；(5) stirring cooling, with the neutralization of 30% sodium hydroxide solution to neutrality.Wetted with product of the present invention, decontamination and washing ability are strong, and bubble is few, with significant industrial application value.
Description
Technical field
The present invention relates to a kind of surfactant palmitoleic acid hexahydrobenzoid acid polyethylene glycol sulfonated ester manufacture method.
Background technology
Caprolactam is important industrial chemicals, is widely used in chemical fibre and plastic article industry.Toluene method produces oneself
Lactams technical process can produce a large amount of technique waste waters, wherein contain a large amount of hexahydrobenzoid acid sulfonate by-products.Adopt at present
It is crude product that Chemical Decomposition method separates the hexahydrobenzoid acid sulfonate for obtaining, in order to improve the industrial valency of hexahydrobenzoid acid sulfonate
Value, obtains the chemically derived product with industrial use, with positive practical significance.
The present invention can be produced in oneself such that it is able to thoroughly solve toluene method in a large number using hexahydrobenzoid acid sulfonate product
The urgent environmental issue of acid amides technique waste water.
Content of the invention
It is an object of the invention to provide a kind of novel surfactant manufacture method, solves toluene method and produces acyl in oneself
In amine technique waste water, a large amount of hexahydrobenzoid acid sulfonate by-products crude products cannot effectively utilizes problem.
For above-mentioned of the prior art can not solve hexahydrobenzoid acid sulfonate by-products crude product application problem, this
Invention using polyethylene glycol and hexahydrobenzoid acid sulfonate special construction, using esterifying reaction method, by polyethylene glycol substep with
Hexahydrobenzoid acid sulfonate and palmitoleic acid are esterified, and prepare palmitoleic acid hexahydrobenzoid acid polyethylene glycol sulfonated ester.
It is preferred that palmitoleic acid hexahydrobenzoid acid polyethylene glycol sulfonated ester, is hexahydrobenzoid acid by the mol ratio of following raw material
Sulfonate: palmitoleic acid: polyethylene glycol (PEG400)=1: 1: 1.05-1.15 synthesis.
Or, preferred palmitoleic acid hexahydrobenzoid acid polyethylene glycol sulfonated ester is hexamethylene by the mol ratio of following raw material
Base formic acid sulfonate: palmitoleic acid: polyethylene glycol (PEG600)=1: 1: 1.05-1.15 synthesis.
Palmitoleic acid hexahydrobenzoid acid macrogol ester sodium sulfonate manufacture method, operates according to following steps：
(1) according to hexahydrobenzoid acid sulfonate: polyethylene glycol (mole)=1: 1, by hexahydrobenzoid acid sulfonate with poly-
Ethylene glycol input carries dehydrater retort, N2Protection, adds 0.5% p-methyl benzenesulfonic acid of gross mass to make catalyst, adds diformazan
Benzene is that dimethylbenzene accounts for gross mass 10-15% with aqueous solvent；
(2) it is heated to 130-140 DEG C of reaction and takes off esterification water, reaction time 6-8 hour；
(3) when reaching theoretical water yield by removing dehydration esterification reaction amount, according to palmitoleic acid: polyethylene glycol (mole
Amount)=1: 1.05-1.15 ratio addition palmitoleic acid, 130-140 DEG C of reaction is except esterification water, reaction time 8-10 hour；
(4) by theoretical water yield being reached except dereaction dehydrating amount, determine when acid number reaches 10-15mgKOH/g and improve instead
Answer temperature 150-160 DEG C to react 1.5 hours, steam dimethylbenzene；
(5) stirring cooling, adds 30% sodium hydroxide solution to neutralize, adjusts pH value 6-7, be cooled to room temperature when 70-80 DEG C.
The product palmitoleic acid hexahydrobenzoid acid macrogol ester sulphonate surfactant function admirable, HLB value 12-14,
Wetting, decontamination and washing ability are strong, and bubble is few, is a kind of high-quality surfactant kind, with significant industrial application value.
Surfactant prepared by the present invention, the table for replacing palmitoleic acid manufacture using other plant oleic acid, animal oleic acid
Face activating agent has similar effect.
Specific embodiment
With reference to embodiment, the present invention is further detailed explanation, but the scope of protection of present invention not because
This is confined to the scope represented by embodiment.
Embodiment 1：
Palmitoleic acid hexahydrobenzoid acid PEG400 ester sodium sulfonate manufacture method, operates according to following steps：
(1) 230g hexahydrobenzoid acids sodium sulfonate is carried dehydrater retort, N with 400g polyethylene glycol PEG400 inputs2
Protection, adds gross mass 3.15g p-methyl benzenesulfonic acid to make catalyst, and it is band aqueous solvent to add 65g dimethylbenzene：
(2) it is heated to 130-140 DEG C of reaction and takes off esterification water, reaction time 6-8 hour；
(3), when reaching theoretical water yield 18g by removing dehydration esterification reaction amount, palmitoleic acid 231g, 130-140 are added
DEG C reaction remove esterification water, reaction time 8-10 hour；
(4) by theoretical water yield 18g being reached except dereaction dehydrating amount, determine when acid number reaches 10-15mgKOH/g and improve
Reaction temperature 150-160 DEG C is reacted 1.5 hours, steams dimethylbenzene；
(5) stirring cooling, adds 30% sodium hydroxide solution 2g to neutralize, adjusts pH value 6-7, be cooled to room when 70-80 DEG C
Temperature.
Embodiment 2：
Palmitoleic acid hexahydrobenzoid acid Macrogol 600 ester sodium sulfonate manufacture method, operates according to following steps：
(1) 230g hexahydrobenzoid acids sodium sulfonate is carried dehydrater retort, N with 600g polyethylene glycol PEG600 inputs2
Protection, adds gross mass 3.15g p-methyl benzenesulfonic acid to make catalyst, and it is band aqueous solvent to add 70g dimethylbenzene：
(2) it is heated to 130-140 DEG C of reaction and takes off esterification water, reaction time 6-8 hour；
(3) when reaching water yield 18g by removing dehydration esterification reaction amount, palmitoleic acid 235g is added, 130-140 DEG C anti-
Esterification water, reaction time 8-10 hour should be removed；
(4) by water yield 18g being reached except dereaction dehydrating amount, determine when acid number reaches 10-15mgKOH/g and improve reaction
Temperature 150-160 DEG C is reacted 1.5 hours, steams dimethylbenzene；
(5) stirring cooling, adds 30% sodium hydroxide solution 2g to neutralize, adjusts pH value 6-7, be cooled to room when 70-80 DEG C
Temperature.
Embodiment 3：
Palmitoleic acid hexahydrobenzoid acid Macrogol 600 ester sodium sulfonate manufacture method, operates according to following steps：
(1) 230g hexahydrobenzoid acids sodium sulfonate is carried dehydrater retort, N with 600g polyethylene glycol PEG600 inputs2
Protection, adds gross mass 3.15g p-methyl benzenesulfonic acid to make catalyst, and it is band aqueous solvent to add 65g dimethylbenzene：
(2) it is heated to 130-140 DEG C of reaction and takes off esterification water, reaction time 6-8 hour；
(3), when reaching theoretical water yield 18g by removing dehydration esterification reaction amount, palmitoleic acid 221g, 130-140 are added
DEG C reaction remove esterification water, reaction time 8-10 hour；
(4) by water yield 18g being reached except dereaction dehydrating amount, determine when acid number reaches 10-15mgKOH/g and improve reaction
Temperature 150-160 DEG C is reacted 1.5 hours, steams dimethylbenzene；
(5) stirring cooling, adds 30% sodium hydroxide solution 2g to neutralize, adjusts pH value 6-7, be cooled to room when 70-80 DEG C
Temperature.
It is excellent that the present invention prepares palmitoleic acid hexahydrobenzoid acid macrogol ester sodium sulfonate some surface active property, HLB value
12.6-13.5, wetting, decontamination and washing ability are strong, and bubble is few, is a kind of high-quality surfactant kind, with significant work
Industry using value, can be widely used in the industries such as weaving, detergents and cosmetic, printing and dyeing.
Above example is one kind of the preferred embodiments of the present invention, using other oleic acid substitute palmitoleic acids or
Other generally changes should be included in the scope of the present invention.
Claims (5)
1. palmitoleic acid hexahydrobenzoid acid polyethylene glycol sulfonated ester, it is characterised in that by the Material synthesis of following mol ratio：Ring
Hexyl formic acid sulfonate: palmitoleic acid: polyethylene glycol (PEG400)=1: 1: 1.05-1.15.
2. palmitoleic acid hexahydrobenzoid acid polyethylene glycol sulfonated ester, it is characterised in that by the Material synthesis of following mol ratio：Ring
Hexyl formic acid sulfonate: palmitoleic acid: polyethylene glycol (PEG600)=1: 1: 1.05-1.15.
3. palmitoleic acid hexahydrobenzoid acid polyethylene glycol sulfonated ester manufacture method, it is characterised in that operate according to following steps：
(1) according to hexahydrobenzoid acid sulfonate: polyethylene glycol (mole)=1: 1, by hexahydrobenzoid acid sulfonate and poly- second two
Alcohol input carries dehydrater retort, N2Protection, adds 0.5% p-methyl benzenesulfonic acid of gross mass to make catalyst, and addition dimethylbenzene is
Band aqueous solvent, dimethylbenzene account for gross mass 10-15%；
(2) it is heated to 130-140 DEG C of reaction and takes off esterification water, reaction time 6-8 hour；
(3) when reaching theoretical water yield by removing dehydration esterification reaction amount, according to palmitoleic acid: polyethylene glycol (mole)=
1: 1.05-1.15 ratio adds palmitoleic acid, 130-140 DEG C of reaction to remove esterification water, reaction time 8-10 hour；
(4) by theoretical water yield being reached except dereaction dehydrating amount, determine when acid number reaches 10-15mgKOH/g and improve reaction temperature
150-160 DEG C of degree reacts 1.5 hours, steams dimethylbenzene；
(5) stirring cooling, adds 30% sodium hydroxide solution to neutralize, adjusts pH value 6-7, be cooled to room temperature when 70-80 DEG C.
4. the manufacture method as described in right 3, replaces the surfactant of palmitoleic acid manufacture to have using other oleic acid similar
Effect.
5., as described in right 4, when other oleic acid replace palmitoleic acid to manufacture such surfactant, its material molar ratio is：Ring
Hexyl formic acid sulfonate: oleic acid: polyethylene glycol=1: 1: 1.05-1.15.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610893276.6A CN106496078A (en) | 2016-10-13 | 2016-10-13 | A kind of palmitoleic acid hexahydrobenzoid acid polyethylene glycol sulfonated ester manufacture method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610893276.6A CN106496078A (en) | 2016-10-13 | 2016-10-13 | A kind of palmitoleic acid hexahydrobenzoid acid polyethylene glycol sulfonated ester manufacture method |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN106496078A true CN106496078A (en) | 2017-03-15 |
Family
ID=58294889
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201610893276.6A Pending CN106496078A (en) | 2016-10-13 | 2016-10-13 | A kind of palmitoleic acid hexahydrobenzoid acid polyethylene glycol sulfonated ester manufacture method |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN106496078A (en) |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003160534A (en) * | 2001-11-26 | 2003-06-03 | New Japan Chem Co Ltd | Method for producing polyethylene glycol dibenzoic acid ester |
| CN101747192A (en) * | 2009-12-15 | 2010-06-23 | 浙江合诚化学有限公司 | Method for synthesizing polyethylene glycol (PEG) oleate |
| CN103120911A (en) * | 2012-11-30 | 2013-05-29 | 中国林业科学研究院林产化学工业研究所 | Colophony/fatty acid sealing end non-ionic surface active agent and preparation method thereof |
| CN104045555A (en) * | 2013-03-15 | 2014-09-17 | 中国石油化工股份有限公司 | Preparation method of triethylene glycol dicarboxylate |
-
2016
- 2016-10-13 CN CN201610893276.6A patent/CN106496078A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003160534A (en) * | 2001-11-26 | 2003-06-03 | New Japan Chem Co Ltd | Method for producing polyethylene glycol dibenzoic acid ester |
| CN101747192A (en) * | 2009-12-15 | 2010-06-23 | 浙江合诚化学有限公司 | Method for synthesizing polyethylene glycol (PEG) oleate |
| CN103120911A (en) * | 2012-11-30 | 2013-05-29 | 中国林业科学研究院林产化学工业研究所 | Colophony/fatty acid sealing end non-ionic surface active agent and preparation method thereof |
| CN104045555A (en) * | 2013-03-15 | 2014-09-17 | 中国石油化工股份有限公司 | Preparation method of triethylene glycol dicarboxylate |
Non-Patent Citations (2)
| Title |
|---|
| 安红等: ""混酸PEG酯的合成及性能研究"", 《精细石油化工》 * |
| 章城亮等: ""聚乙二醇400单油酸酯的研发及生产"", 《浙江化工》 * |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0482687A1 (en) | Concentrated, liquid, pourable composition | |
| JP7042339B2 (en) | Alkoxylated secondary alcohol sulfate | |
| CN106966923A (en) | A kind of synthetic method of 3 methoxyl group N, N dimethylpropionamides | |
| CN101759559A (en) | Method for preparing lactic acid n-propyl ester with low water content, low acidity and high purity | |
| CN101462980B (en) | Industrial production method of 2,6-difluorobenzamide | |
| CN109627195A (en) | A method of heavy alkylbenzene sulfonate is prepared using microreactor | |
| CN106496078A (en) | A kind of palmitoleic acid hexahydrobenzoid acid polyethylene glycol sulfonated ester manufacture method | |
| CN110862309A (en) | Paraformaldehyde depolymerization method and depolymerization device thereof | |
| CN102311420B (en) | Method for synthesizing epsilon-caprolactone | |
| CN110963912B (en) | Method for preparing 2, 4-dibromo methyl butyrate by catalyzing bromosulfonic acid resin | |
| CN105439882B (en) | A kind of fast and efficiently N fatty acyls amino-acid salt process for synthesizing surfactant | |
| CN104496820A (en) | Preparation method of light stabilizer 2, 4-di-tert-butylphenyl 3, 5-di-tert-butyl-4-hydroxybenzoate | |
| CN101914034A (en) | Method for preparing N,N-diethyl M-Methyl Benzoyl amide | |
| CN110204452A (en) | A kind of preparation method of the Diacetone Acrylamide of low acrylamide content | |
| CN101696162B (en) | Method for preparing glutaric acid from dimethyl glutarate | |
| CN110862308A (en) | Preparation method and application of formaldehyde alcohol solution | |
| CN114163152A (en) | Method for preparing building gypsum by recycling waste nitrified sulfuric acid | |
| CN102718660A (en) | Method for producing quaternary ammonium salt without organic solvents | |
| CN110590610A (en) | Preparation method of high-quality sodium alkyl sulfate | |
| CN112898187A (en) | Method for crystallizing taurine | |
| US2413968A (en) | Process for manufacture of nu-alkyl glycines | |
| CN102633663B (en) | Clean technique for producing nitrilotriacetic acid | |
| CN110407701A (en) | The preparation method of trioctyl lemon acid | |
| CN110272329A (en) | The preparation method of one kind 1,2- hexylene glycol | |
| CN103360436A (en) | Preparation method of alkyl polyglycoside phosphates |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20170315 |
|
| WD01 | Invention patent application deemed withdrawn after publication |