METHOD OF PRODUCING REFINED OIL AND/OR FAT

Abstract

The present invention provides a method of producing a refined oil and/or fat, comprising step B: a step of steam-distilling a raw material oil and/or fat at 240° C. or more, wherein a content of saturated hydrocarbons having 20 to 35 carbon atoms in the refined oil and/or fat is 10 ppm by mass or less.

Claims

1. A method of producing a refined oil and/or fat, comprising step B: a step of steam-distilling a raw material oil and/or fat at 240° C. or more, wherein a content of saturated hydrocarbons having 20 to 35 carbon atoms in the refined oil and/or fat is 10 ppm by mass or less.

2. The method according to claim 1, wherein the steam distillation of the step B is carried out for 0.5 to 9 hours.

3. The method of producing a refined oil and/or fat according to claim 1, further comprising, after the step B, step C: a step of heat-treating the oil and/or fat obtained in the step B, wherein a content of glycidols in the refined oil and/or fat is 1 ppm by mass or less.

4. The method according to claim 3, wherein the heat treatment step of the step C is step C2: a step of steam-distilling the oil and/or fat obtained in the step B at 180 to 220° C.

5. The method according to claim 3, wherein the heat treatment step of the step C includes step C1: a step of bringing the oil and/or fat obtained in the step B into contact with an acidic substance, and step C2: a step of steam-distilling the contacted oil and/or fat at 180 to 220° C.

6. The method according to claim 4, wherein the steam distillation of the step C2 is carried out for 0.5 to 9 hours.

7. The method according to claim 1, further comprising, before the step B, step A: a step of preparing a raw material oil and/or fat containing monochloropropanols in an amount of 2 ppm by mass or less.

8. The method according to claim 7, wherein the raw material oil and/or fat of the step A is obtained by step A1: a step of dechlorinating the oil and/or fat.

9. The method according to claim 8, wherein the dechlorination step of the step A1 is step A1-1: a step of washing the oil and/or fat with dechlorinated water, and/or step A1-2: a step of bringing the oil and/or fat into contact with an alkaline substance.

10. The method according to claim 8, wherein the raw material oil and/or fat of the step A is obtained by step A2: a step of steam-distilling the oil and/or fat dechlorinated in the step A1 at 210 to 260° C., which is carried out after the dechlorination step of the step A1.

11. A refined oil and/or fat comprising: 1 to 10 ppm by mass of hydrocarbons having saturated hydrocarbons having 20 to 35 carbon atoms; 0.01 to 2 ppm by mass of glycidols; and 0.1 to 2 ppm by mass of monochloropropanols.

12. The refined oil and/or fat according to claim 11, further comprising 0 to 10 ppm by mass of hydrocarbons having aromatic rings having 20 to 35 carbon atoms.

13. The refined oil and/or fat according to claim 11, wherein the content of the hydrocarbons having saturated hydrocarbons having 20 to 35 carbon atoms is 1 to 5 ppm by mass, wherein the content of the glycidols is 0.05 to 1.0 ppm by mass, wherein the content of the monochloropropanols is 0.1 to 1.0 ppm by mass, and wherein hydrocarbons having aromatic rings having 20 to 35 carbon atoms is 0 to 4.5 ppm by mass.

14. A food or drink comprising the refined oil and/or fat according to claim 11.

15. The food or drink according to claim 14, wherein the amount of the refined oil and/or fat is 5 to 95% by mass.

Description

EXAMPLES

[0100] Hereinafter, the present invention is described in more detail using Example. However, the present invention is not limited to the content of the following Embodiment.

<Measurement of Content of Saturated Hydrocarbons (SH) and Content of Hydrocarbons having Aromatic Rings (AH)>

[0101] The content of saturated hydrocarbons (SH) and the content of hydrocarbons having aromatic rings (AH) were measured in accordance with the following method.

(1) An oil and/or fat sample in an amount of 200 mg is added with 3 ppm by mass of bicyclohexyl as an internal standard of saturated hydrocarbons and 3 ppm by mass of 1,3,5-tri-tert-butylbenzene as an internal standard of aromatic hydrocarbons, followed by dissolution with 1 mL of hexane.
(2) The sample of (1) is placed in a 2 g silica solid phase extraction column conditioned with hexane, followed by adsorption.
(3) An eluent A (hexane 100% by volume) and an eluent B (hexane 85% by volume and dichloromethane 15% by volume) are used to elute saturated hydrocarbons and aromatic hydrocarbons. The eluent A is first added and 1 mL is removed. After that, 2 mL of the eluent A and 1 mL of the eluent B are collected to form a saturated hydrocarbon fraction. Next, the eluent B is added, and 8 mL is collected to form an aromatic hydrocarbon fraction.
(4) Each of the fractions is concentrated to about 300 μL and measured by gas chromatography (on-column injection).

(5) Gas Chromatography Measurement Conditions

1. Column

[0102] Pre-column: deactivated fused silica column, length 10 m, inner diameter 0.53 mm
Analysis column: 100% dimethylpolysiloxane, length 15 m, inner diameter 0.32 mm, film thickness 0.1 μm

2. Injection

[0103] Carrier gas: helium
Injection volume: 40 μL
Inlet temperature conditions: 60° C. (retained for 4 minutes).fwdarw.20° C./min temperature rise.fwdarw.380° C. (retained for 15.5 minutes)
Pressure conditions: 60 kPa (retained for 4 minutes).fwdarw.70 kPa/min pressure rise.fwdarw.130 kPa (retained for 30.5 minutes)
Column flow rate: 3.55 mL/min

3. Oven

[0104] Temperature: 50° C. (retained for 4 minutes).fwdarw.20° C./min temperature rise.fwdarw.380° C. (retained for 15 minutes)

4. FID Detector

Temperature: 380° C.

[0105] (6) The chromatogram obtained in the above gas chromatography measurement is used to compare the areas of the internal standards with the areas of the hydrocarbons (the area of the humps which rise from the baseline), thereby calculating the saturated hydrocarbon content and the aromatic hydrocarbon content.

<Measurement of Glycidols and Monochloropropanols Contents>

[0106] Measurement was carried out in accordance with the American Oil Chemists' Society Official Method (AOCS Official Method Cd29a-13). Note that the glycidols to be detected were glycidol and glycidol fatty acid esters. The glycidol content was obtained by converting the amount of glycidol and glycidol fatty acid esters to the amount of free glycidol. Note that, regarding the monochloropropanols, the 3-monochloropropanols to be detected were 3-monochloropropanol and 3-monochloropropanol fatty acid esters, and the 3-monochloropropanol content was obtained by converting the amount of 3-monochloropropanol and 3-monochloropropanol fatty acid esters to the amount of free monochloropropanol. The 2-monochloropropanols to be detected were 2-monochloropropanol and 2-monochloropropanol fatty acid esters, and the 2-monochloropropanol content was obtained by converting the amount of 2-monochloropropanol and 2-monochloropropanol fatty acid esters to the amount of free monochloropropanol. The monochloropropanol content was obtained by converting the total amount of 3-monochloropropanols and 2-monochloropropanols to the amount of free monochloropropanol.

Test Example 1—Step A

[0107] A commercially available crude palm oil was washed with 10 parts by mass of deionized water relative to 100 parts by mass of the crude oil in accordance with a conventional method (step A1-1), and then 0.05 parts by mass of 85% phosphoric acid was added and stirred for phosphoric acid degumming. To 100 parts by mass of the obtained phosphoric acid degummed oil, 1 part by mass of bleaching earth (pH 8.2) was added and sufficiently stirred at 110° C. for 0.5 hours (bleaching: step A1-2). The bleaching earth was removed by filtration to obtain a bleached oil. Steam distillation was carried out by blowing 5 mass parts by mass of steam to 100 parts by mass of the bleached oil for 1.5 hours under the conditions of 230° C. and about 266.7 Pa (2 torrs) (deodorization treatment: step A2). The obtained palm oil was subjected to dry fractionation in two steps to obtain palm super olein having an iodine value of 63 (RBD_PL63).

Test Example 1-Step B

[0108] Batchwise steam distillation (260° C., about 266.7 Pa (2 torrs), 5 parts by mass of steam blown to 100 parts by mass of oil and/or fat, duration 1.5 hours) was repeated three batches using RBD_PL63 obtained above, and RBD3D_PL63 was obtained. The SH content and AH content were measured before steam distillation and at the end of each batch. Similarly, the monochloropropanol and glycidol contents were also measured. Table 1 presents the results. Each batch process or the continuous batch process of the above steam distillation corresponds to the step B.

Test Example 1-Step C

[0109] Activated bleaching earth (pH 6) in an amount of 2 parts by mass was added to 100 parts by mass of RBD3D_PL63 obtained by the above continuous batchwise steam distillation, followed by sufficient stirring at 110° C. for 0.5 hours (bleaching: step C1). The activated bleaching earth was removed by filtration to obtain a bleached oil. Steam distillation was carried out by blowing 5 mass parts by mass of steam to 100 parts by mass of the bleached oil for 1.5 hours under the conditions of 200° C. and about 266.7 Pa (2 torrs) (deodorization treatment: step C2), and RBD3DBD_PL63 was obtained. The SH content and AH content of the obtained RBD3DBD_PL63 were measured. Similarly, the monochloropropanol and glycidol contents were also measured. Table 1 presents the results.

TABLE-US-00001 TABLE 1 Results of Analyzing Oil in Each Step After Batch 3 of Steam Blowing in RBD3DBD_ RBD_ After Batch After Batch 2 Step B PL63 PL63 1 of Steam of Steam (RBD3D_PL63: (Resultant (Raw Material Blowing in Blowing in Resultant Product of Product of of Step B) Step B Step B Step B) Step C) Total Duration of Steam Distillation in Step B (Hour) 0 1.5 3 4.5 — Number of Carbon Atoms SH Content Less Than 20 Less Than 2 Less Than 2 Less Than 2 Less Than 2 Less Than 2 (ppm by Mass) 20 to 35 12.0 5.0 3.0 1.5 2.4 Over 35 11.9 11.7 10.6 9.7 10.2 AH Content Less Than 20 Less Than 2 Less Than 2 Less Than 2 Less Than 2 Less Than 2 (ppm by Mass) 20 to 35 14.4 5.5 4.3 2.4 2.7 Over 35 4.5 5.1 5.1 4.1 4.4 3-MCPD Content (ppm by Mass) 0.41 0.56 0.68 0.65 0.72 2-MCPD Content (ppm by Mass) 0.16 0.25 0.32 0.31 0.38 Glycidol Content (ppm by Mass) 1.41 1.7 2.34 1.47 0.08

Test Example 2—Step A

[0110] A commercially available crude palm oil was added with 0.05 parts by mass of 85% phosphoric acid and stirred in accordance with a conventional method, followed by phosphoric acid degumming. To 100 parts by mass of the obtained phosphoric acid degummed oil, 1 part by mass of bleaching earth (pH 8.7) was added and sufficiently stirred at 110° C. for 0.5 hours (bleaching (alkaline adsorbent treatment): step A1-2). The bleaching earth was removed by filtration to obtain a bleached oil. A semi-continuous deodorizing apparatus was used to carry out steam distillation by blowing 3 mass parts by mass of steam to 100 parts by mass of the bleached oil for 1.5 hours under the conditions of 230° C. and about 266.7 Pa (2 torrs) (deodorization treatment: step A2). The obtained palm oil was subjected to dry fractionation in two steps to obtain palm super olein having an iodine value of 63 (RBD_PL63).

Test Example 2—Step B

[0111] The above-obtained RBD_PL63 in an amount of 50 tons was used to carry out steam distillation (270° C., about 266.7 Pa (2 torrs), 3 parts by mass of steam blown to 100 parts by mass of oil and/or fat, duration 1.5 hours) with a semi-continuous deodorizing column, and RBDD_PL63 was obtained. The SH content and AH content were measured before and after steam distillation. Similarly, the monochloropropanol and glycidol contents were also measured. Table 2 presents the results. The above steam distillation corresponds to the step B.

Test Example 2—Step C

[0112] Activated bleaching earth (pH 5.0) in an amount of 2.5 parts by mass was added to 100 parts by mass of RBDD__PL63 obtained by the above steam distillation with a semi-continuous deodorizing apparatus, followed by sufficient stirring at 110° C. for 0.5 hours (bleaching: step C1). The activated bleaching earth was removed by filtration to obtain a bleached oil. Steam distillation was carried out by blowing 3 mass parts by mass of steam to 100 parts by mass of the bleached oil for 1.5 hours under the conditions of 200° C. and about 266.7 Pa (2 torrs) (deodorization treatment: step C2), and RBDDBD_PL63 was obtained. The SH content and AU content of the obtained RBDDBD_PL63 were measured. Similarly, the monochloropropanol and glycidol contents were also measured. Table 2 presents the results.

TABLE-US-00002 TABLE 2 Results of Analyzing Oil in Each Step RBD_PL63 RBDD_PL63 RBDDBD_PL63 (Raw Material (Resultant Product (Resultant Product of Step B) of Step B) of Step C) Number of Carbon Atoms SH Content Less Than 20 Less Than 2 Less Than 2 Less Than 2 (ppm by Mass) 20 to 35 10.9 3.3 4.3 Over 35 7.7 7.9 8.5 AH Content Less Than 20 Less Than 2 Less Than 2 Less Than 2 (ppm by Mass) 20 to 35 11.5 4.1 4.9 Over 35 4.3 4.1 4.2 3-MCPD Content (ppm by Mass) 0.48 0.69 0.68 2-MCPD Content (ppm by Mass) 0.16 0.11 0.22 Glycidol Content (ppm by Mass) 1.55 5.5 0.80

Test Example 3—Step A

[0113] A commercially available crude palm oil was added with 0.05 parts by mass of 85% phosphoric acid and stirred in accordance with a conventional method, followed by phosphoric acid degumming. To 100 parts by mass of the obtained phosphoric acid degummed oil, 1 part by mass of bleaching earth (pH 8.7) was added and sufficiently stirred at 110° C. for 0.5 hours (bleaching (alkaline adsorbent treatment): step A1-2). The bleaching earth was removed by filtration to obtain a bleached oil. A semi-continuous deodorizing apparatus was used to carry out steam distillation by blowing 3 mass parts by mass of steam to 100 parts by mass of the bleached oil for 1.5 hours under the conditions of 230° C. and about 266.7 Pa (2 torrs) (deodorization treatment: step A2). The obtained palm oil was subjected to dry fractionation in two steps to obtain palm super olein having an iodine value of 63 (RBD_PL63).

Test Example 3—Step B

[0114] The above-obtained RBD_PL63 in an amount of 500 tons was used to carry out steam distillation (265° C., about 266.7 Pa (2 torrs), 3 parts by mass of steam blown to 100 parts by mass of oil and/or fat, duration 1.5 hours) with a semi-continuous deodorizing column, and RBDD_PL63 was obtained. The SH content and AH content were measured before and after steam distillation. Similarly, the monochloropropanol and glycidol contents were also measured. Table 3 presents the results. The above steam distillation corresponds to the step B.

Test Example 3—Step C

[0115] Activated bleaching earth (pH 5.0) in an amount of 2.0 parts by mass was added to 100 parts by mass of RBDD_PL63 obtained by the above steam distillation with a semi-continuous deodorizing apparatus, followed by sufficient stirring at 110° C. for 0.5 hours (bleaching: step C1). The activated bleaching earth was removed by filtration to obtain a bleached oil. Steam distillation was carried out by blowing 3 mass parts by mass of steam to 100 parts by mass of the bleached oil for 1.5 hours under the conditions of 195° C. and about 266.7 Pa (2 torrs) (deodorization treatment: step C2), and RBDDBD_PL63 was obtained. The SH content and AH content of the obtained RBDDBD_PL63 were measured. Similarly, the monochloropropanol and glycidol contents were also measured. Table 3 presents the results.

TABLE-US-00003 TABLE 3 Results of Analyzing Oil in Each Step RBD_PL63 RBDD_PL63 RBDDBD_PL63 (Raw Material (Resultant Product (Resultant Product of Step B) of Step B) of Step C) Number of Carbon Atoms SH Less Less Less Less Content Than 20 Than 2 Than 2 Than 2 (ppm by 20 to 35 16.4 7.1 7.1 Mass) Over 35 13.8 14.1 13.8 AH Content Less Less Less Less (ppm by Than 20 Than 2 Than 2 Than 2 Mass) 20 to 35 13.5 4.3 4.5 Over 35 5.1 4.5 4.7 3-MCPD Content 0.31 0.62 0.59 (ppm by Mass) 2-MCPD Content 0.11 0.15 0.15 (ppm by Mass) Glycidol Content 1.67 5.3 0.32 (ppm by Mass)

Test Example 4—Step A

[0116] A commercially available palm olein (RBD_PL56) was chemically interesterified in accordance with a conventional method. Specifically, the palm olein was sufficiently dried, and 0.15 parts by mass of sodium methoxide was added to 100 parts by mass of the palm olein, followed by interesterification reaction with stirring at 100° C. for 20 minutes under reduced pressure (alkaline substance contact treatment: step A1-2). After that, 1 part by mass of a saturated aqueous solution of citric acid was added to 100 parts by mass of reaction oil and/or fat (interesterified oil) to stop the reaction. The interesterified oil and/or fat after reaction termination was washed with 6-time amount of warm water (ion exchanged water at 90° C.) (step A1-1) and dried under reduced pressure. To 100 parts by mass of the obtained interesterified oil and/or fat, 2 parts by mass of bleaching earth (pH 8.7) was added and sufficiently stirred at 110° C. for 0.5 hours (bleaching (alkaline adsorbent treatment): step A1-2). The bleaching earth was removed by filtration to obtain a bleached oil of the interesterified oil and/or fat (RBDIEB_PL56).

Test Example 4—Step B

[0117] Batchwise steam distillation (260° C., about 266.7 Pa (2 torrs), 5 parts by mass of steam blown to 100 parts by mass of oil and/or fat, duration 1.5 hours) was carried out using RBDIEB-PL56 obtained above, and RBDIEBD_PL56 was obtained. The SH content and AH content were measured before and after steam distillation. Similarly, the monochloropropanol and glycidol contents were also measured. Table 4 presents the results. The above steam distillation corresponds to the step B.

Test Example 4—Step C

[0118] Activated bleaching earth (pH 5.0) in an amount of 2 parts by mass was added to 100 parts by mass of RBDIEBD_PL56 obtained by the above steam distillation, followed by sufficient stirring at 110° C. for 0.5 hours (bleaching: step C1). The activated bleaching earth was removed by filtration to obtain a bleached oil. Steam distillation was carried out by blowing 5 mass parts by mass of steam to 100 parts by mass of the bleached oil for 1.5 hours under the conditions of 200° C. and about 266.7 Pa (2 torrs) (deodorization treatment: step C2), and RBDIEBDBD_PL56 was obtained. The SH content and AH content of the obtained RBDIEBDBD_PL56 were measured. Similarly, the monochloropropanol and glycidol contents were also measured. Table 4 presents the results.

TABLE-US-00004 TABLE 4 RBD_PL56 RBDIEB_PL56 RBDIEBD_PL56 RBDIEBDBD_PL56 (Raw (Raw (Resultant (Resultant Material Material Product Product of Step A) of Step B) of Step B) of Step C) Number of Carbon Atoms SH Content Less Than 20 Less Than 2 Less Than 2 Less Than 2 Less Than 2 (ppm by 20 to 35 10.6 10.7 5.5 5.5 Mass) Over 35 13.3 13.3 12.5 12.5 AH Content Less Than 20 Less Than 2 Less Than 2 Less Than 2 Less Than 2 (ppm by 20 to 35 6.8 7.2 Less Than 2 Less Than 2 Mass) Over 35 4.6 4.9 3.5 3.1 3-MCPD Content (ppm by Mass) 5.21 0.0 0.25 0.26 2-MCPD Content (ppm by Mass) 2.33 0.0 0.09 0.10 Glycidol Content (ppm by Mass) 10.31 72.31 8.20 0.09