CN105859554A - Method for adsorbing and purifying n-diheptyl phthalate - Google Patents
Method for adsorbing and purifying n-diheptyl phthalate Download PDFInfo
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- CN105859554A CN105859554A CN201610359339.XA CN201610359339A CN105859554A CN 105859554 A CN105859554 A CN 105859554A CN 201610359339 A CN201610359339 A CN 201610359339A CN 105859554 A CN105859554 A CN 105859554A
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- CN
- China
- Prior art keywords
- phthalate ester
- ester
- heptyl phthalate
- heptyl
- purifying
- 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.)
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- 238000000034 method Methods 0.000 title claims abstract description 12
- JQCXWCOOWVGKMT-UHFFFAOYSA-N diheptyl phthalate Chemical compound CCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC JQCXWCOOWVGKMT-UHFFFAOYSA-N 0.000 title abstract 4
- -1 hydroxypropyl Chemical group 0.000 claims abstract description 44
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000000047 product Substances 0.000 claims abstract description 14
- 239000003463 adsorbent Substances 0.000 claims abstract description 9
- UYUXSRADSPPKRZ-SKNVOMKLSA-N D-glucurono-6,3-lactone Chemical compound O=C[C@H](O)[C@H]1OC(=O)[C@@H](O)[C@H]1O UYUXSRADSPPKRZ-SKNVOMKLSA-N 0.000 claims abstract description 8
- 229920001503 Glucan Polymers 0.000 claims abstract description 8
- 239000012043 crude product Substances 0.000 claims abstract description 8
- 229950002441 glucurolactone Drugs 0.000 claims abstract description 8
- 238000000746 purification Methods 0.000 claims description 9
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 7
- 239000011574 phosphorus Substances 0.000 claims description 7
- 229910052698 phosphorus Inorganic materials 0.000 claims description 7
- BZYYDNPTCATFHG-UHFFFAOYSA-O 2-(3-methylimidazol-3-ium-1-yl)acetic acid nitrate Chemical compound [N+](=O)([O-])[O-].C(=O)(O)C[N+]1=CN(C=C1)C BZYYDNPTCATFHG-UHFFFAOYSA-O 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 5
- 238000010792 warming Methods 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 4
- 235000009754 Vitis X bourquina Nutrition 0.000 claims 1
- 235000012333 Vitis X labruscana Nutrition 0.000 claims 1
- 240000006365 Vitis vinifera Species 0.000 claims 1
- 235000014787 Vitis vinifera Nutrition 0.000 claims 1
- 150000002596 lactones Chemical class 0.000 claims 1
- 238000003756 stirring Methods 0.000 abstract description 2
- DTGKYEKXUPSPJH-UHFFFAOYSA-O 2-(1H-imidazol-3-ium-3-yl)acetic acid nitrate Chemical compound C1=C[N+](=CN1)CC(=O)O.[N+](=O)([O-])[O-] DTGKYEKXUPSPJH-UHFFFAOYSA-O 0.000 abstract 1
- 238000001035 drying Methods 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 16
- 230000000052 comparative effect Effects 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- SLBQXWXKPNIVSQ-UHFFFAOYSA-N 4-nitrophthalic acid Chemical compound OC(=O)C1=CC=C([N+]([O-])=O)C=C1C(O)=O SLBQXWXKPNIVSQ-UHFFFAOYSA-N 0.000 description 4
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 238000010189 synthetic method 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
- OXSANYRLJHSQEP-UHFFFAOYSA-N 4-aminophthalic acid Chemical compound NC1=CC=C(C(O)=O)C(C(O)=O)=C1 OXSANYRLJHSQEP-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241001062009 Indigofera Species 0.000 description 1
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/56—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a method for adsorbing and purifying n-diheptyl phthalate. The method comprises the steps of adding hydroxypropyl glucan, d-glucurono-3, 6-lactone, trans-butylphosphine diacid, 1-carboxymethyl-3-imidazolium nitrate and methyl alcohol into a stirring tank, raising the temperature to the appropriate temperature, and after the temperature is preserved for a certain time, conducting filtration and drying, so that adsorbent is obtained; adding an obtained adsorbent product into an exchange column, adding a crude product n-diheptyl phthalate from above the exchange column, and obtaining effluent as purified n-diheptyl phthalate.
Description
Technical field
The present invention relates to a kind of process for purification, a kind of method adsorbing purification heptyl phthalate ester.
Background technology
Heptyl phthalate ester is the primary plasticizer of polyvinyl chloride, compares with dioctyl phthalate, this product
Compatibility and plasticizing efficiency are the best, and the performance such as tensile strength, percentage elongation, cold resistance is substantially the same, but volatility is bigger.This product is also
Can be used for vinyl chloride copolymer, nitrocellulose lacquer and multiple rubber.
CN102225901A discloses the synthetic method of a kind of 4-aminophthalic acid two heptyl ester, with 4-nitrophthalic acid
For raw material, with enanthol generation esterification, prepare 4-nitrophthalic acid two heptyl ester, at the phenyl ring of dibutyl phthalate (DHP)
On introduce a nitro, be then reduced to nitro to synthesize 4-amino neighbour's benzene two with the active amino of protein bound
Formic acid two heptyl ester.Synthetic route of the present invention is simple, low cost, is easy to application.
CN102225898A discloses the synthetic method of a kind of 4-nitrophthalic acid two heptyl ester, is at 4-nitro neighbour's benzene
Adding enanthol in dioctyl phthalate, add catalyst, be stirred at reflux at 115-125 DEG C under stirring condition, decompression boils off unreacted
The water that enanthol and reaction generate, pours into while hot in frozen water, under agitation drips sodium carbonate liquor, until the pH value of water layer is 6.5-
After 7.2, isolate grease through subsequent treatment, obtain yellow oily liquid 4-nitrophthalic acid two heptyl ester.The present invention closes
Become route simple, low cost, it is easy to application.
Existing patent and the used purifying technique of technical literature, all use distillation or the technique of evaporation, and energy consumption is high, and equipment is thrown
Money is big, is unfavorable for industrialized production.
Summary of the invention
In order to solve above technical problem, present invention employs following technical scheme: a kind of absorption purifies O-phthalic
The method of acid two positive heptyl esters, comprises the following steps:
Step 1. carboxylic acid reaction
By weight, stirred tank adds 100 parts of hydroxypropyl glucans, 0.01-0.1 part glucurone, 1-5 part
Anti-fourth phosphorus diacid, 0.01-0.1 part 1-carboxymethyl-3-methylimidazolium nitrate, 100-400 part methyl alcohol, it is warming up to 50-80 DEG C, protects
Temperature 30-60h, filters, and is dried, obtains adsorbent.
Step 2, the purifying of the positive heptyl ester of terephthalic acid (TPA) two
By weight, exchange column adds step 1 and obtain adsorbent product 100 parts, by positive for crude product phthalic acid two heptan
Ester adds above exchange column, flow velocity 50-150L/h, and efflux is heptyl phthalate ester after purification.
Hydroxypropyl glucan described in step 1 be commercially available prod be commercially available prod, as Xi'an indigo plant dawn science and technology new material share
The product that Co., Ltd produces；Glucurone is commercially available prod, the product produced such as Shanghai Bang Cheng Chemical Co., Ltd.；
Anti-fourth phosphorus diacid is commercially available prod, the product produced such as Nanjing Golden Bridge chemical plant.
Heptyl phthalate ester crude product in the present invention is commercially available prod, such as think of sky, the Chengdu limited public affairs of moral biotechnology
The product that department produces.
Compared with prior art, the method have the advantages that
Containing polyhydroxy in hydroxypropyl glucan skeleton, carboxyl, to acid in heptyl phthalate ester, alcohol, aldehyde etc. is main
The adsorbance of the low-molecular material of composition improves.
Detailed description of the invention
Below in conjunction with specific embodiment, it is further elucidated with the present invention, but these embodiments are only used for explaining the present invention, and not
It is for limiting the scope of the present invention.
Heptyl phthalate ester crude product in embodiment is the product that Si Tiande bio tech ltd, Chengdu produces
Product.
Embodiment 1
Step 1. carboxylic acid reaction
Addition hydroxypropyl glucan 100Kg, glucurone 0.05Kg, anti-fourth phosphorus diacid 3Kg in 1000L stirred tank,
1-carboxymethyl-3-methylimidazolium nitrate 0.05Kg, methyl alcohol 300Kg, be warming up to 60 DEG C, is incubated 50h, filters, and is dried, is inhaled
Attached dose.
Step 2, the purifying of the positive heptyl ester of terephthalic acid (TPA) two
The adsorbent product 100Kg that step 1 obtains is added, by crude product heptyl phthalate ester from exchange column in exchange column
Top adds, and flow velocity 100L/h, efflux is heptyl phthalate ester after purification.Heptyl phthalate ester is pure
Degree is shown in Table 1.
Embodiment 2
Step 1. carboxylic acid reaction
Addition hydroxypropyl glucan 100Kg, glucurone 0.01Kg, anti-fourth phosphorus diacid 1Kg in 1000L stirred tank,
1-carboxymethyl-3-methylimidazolium nitrate 0.01Kg, methyl alcohol 100Kg, be warming up to 50 DEG C, is incubated 30h, filters, and is dried, is inhaled
Attached dose.
Step 2, the purifying of the positive heptyl ester of terephthalic acid (TPA) two
The adsorbent product 100Kg that step 1 obtains is added, by crude product heptyl phthalate ester from exchange column in exchange column
Top adds, and flow velocity 50L/h, efflux is heptyl phthalate ester after purification.Heptyl phthalate ester is pure
Degree is shown in Table 1.
Embodiment 3
Step 1. carboxylic acid reaction
Hydroxypropyl glucan 100Kg, glucurone 0.1Kg, anti-fourth phosphorus diacid 5Kg, 1-is added in 1000L stirred tank
Carboxymethyl-3-methylimidazolium nitrate 0.1Kg, methyl alcohol 400Kg, be warming up to 80 DEG C, is incubated 60h, filters, and is dried, is adsorbed
Agent.
Step 2, the purifying of the positive heptyl ester of terephthalic acid (TPA) two
The adsorbent product 100Kg that step 1 obtains is added, by crude product heptyl phthalate ester from exchange column in exchange column
Top adds, and flow velocity 150L/h, efflux is heptyl phthalate ester after purification.Heptyl phthalate ester is pure
Degree is shown in Table 1.
Comparative example 1
Step 1 is added without glucurone, the other the same as in Example 1, and heptyl phthalate ester is shown in Table 1.
Comparative example 2
Step 1 is added without anti-fourth phosphorus diacid, and the other the same as in Example 1, heptyl phthalate ester is shown in Table 1.
Comparative example 3
Step 1 is added without 1-carboxymethyl-3-methylimidazolium nitrate, the other the same as in Example 1, heptyl phthalate ester purity
It is shown in Table 1.
Table 1: the heptyl phthalate ester purity table of embodiment 1-3 and comparative example 1-3.
| Embodiment | Heptyl phthalate ester purity % |
| 1 | 99.7 |
| 2 | 99.5 |
| 3 | 99.9 |
| Comparative example 1 | 99.1 |
| Comparative example 2 | 98.8 |
| Comparative example 3 | 98.9 |
Claims (2)
1. one kind adsorbs the method purifying heptyl phthalate ester, it is characterised in that comprise the following steps:
Step 1. carboxylic acid reaction
By weight, stirred tank adds 100 parts of hydroxypropyl glucans, glucurone, 1-5 part anti-fourth phosphorus two
Acid, 0.01-0.1 part 1-carboxymethyl-3-methylimidazolium nitrate, 100-400 part methyl alcohol, it is warming up to 50-80 DEG C, is incubated 30-
60h, filters, and is dried, obtains adsorbent；
Step 2, the purifying of heptyl phthalate ester
By weight, exchange column adds step 1 and obtain adsorbent product 100 parts, by positive for crude product phthalic acid two heptan
Ester adds above exchange column, flow velocity 50-150L/h, and efflux is heptyl phthalate ester after purification.
A kind of method adsorbing purification heptyl phthalate ester the most according to claim 1, it is characterised in that grape
Uronic acid lactone weight portion is 0.01-0.1 part.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610359339.XA CN105859554A (en) | 2016-05-27 | 2016-05-27 | Method for adsorbing and purifying n-diheptyl phthalate |
| CN201710279944.0A CN106986770B (en) | 2016-05-27 | 2017-04-26 | A kind of purification process of heptyl phthalate ester |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610359339.XA CN105859554A (en) | 2016-05-27 | 2016-05-27 | Method for adsorbing and purifying n-diheptyl phthalate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN105859554A true CN105859554A (en) | 2016-08-17 |
Family
ID=56641355
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201610359339.XA Withdrawn CN105859554A (en) | 2016-05-27 | 2016-05-27 | Method for adsorbing and purifying n-diheptyl phthalate |
| CN201710279944.0A Active CN106986770B (en) | 2016-05-27 | 2017-04-26 | A kind of purification process of heptyl phthalate ester |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201710279944.0A Active CN106986770B (en) | 2016-05-27 | 2017-04-26 | A kind of purification process of heptyl phthalate ester |
Country Status (1)
| Country | Link |
|---|---|
| CN (2) | CN105859554A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107233862A (en) * | 2017-08-02 | 2017-10-10 | 王艺霖 | A kind of preparation method of methyl phenyl silicone oil adsorbent |
| CN107691933A (en) * | 2017-09-15 | 2018-02-16 | 江山海维科技有限公司 | A kind of manufacture method of root of kudzu vine Normal juice |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0320206D0 (en) * | 2003-08-29 | 2003-10-01 | Exxonmobil Chem Patents Inc | Improvements in or relating to plasticiser |
-
2016
- 2016-05-27 CN CN201610359339.XA patent/CN105859554A/en not_active Withdrawn
-
2017
- 2017-04-26 CN CN201710279944.0A patent/CN106986770B/en active Active
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107233862A (en) * | 2017-08-02 | 2017-10-10 | 王艺霖 | A kind of preparation method of methyl phenyl silicone oil adsorbent |
| CN107691933A (en) * | 2017-09-15 | 2018-02-16 | 江山海维科技有限公司 | A kind of manufacture method of root of kudzu vine Normal juice |
Also Published As
| Publication number | Publication date |
|---|---|
| CN106986770A (en) | 2017-07-28 |
| CN106986770B (en) | 2019-04-05 |
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Application publication date: 20160817 |